# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
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data_MeQn_17srv201
_database_code_depnum_ccdc_archive 'CCDC 1985987'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-02-24 deposited with the CCDC. 2020-06-09 downloaded from the CCDC.
;
_audit_creation_date 2017-08-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'B F4, C21 H27 N2 O2, 0.5(H2 O)'
_chemical_formula_sum 'C21 H28 B F4 N2 O2.50'
_chemical_formula_weight 435.26
_chemical_absolute_configuration ad
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 8.0721(2)
_cell_length_b 15.6353(5)
_cell_length_c 16.4422(5)
_cell_angle_alpha 90
_cell_angle_beta 98.2832(14)
_cell_angle_gamma 90
_cell_volume 2053.52(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9656
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 74.25
_cell_measurement_theta_min 2.72
_shelx_estimated_absorpt_T_max 0.917
_shelx_estimated_absorpt_T_min 0.683
_exptl_absorpt_coefficient_mu 0.983
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8637
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0898 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8637.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.408
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plank
_exptl_crystal_F_000 916
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.09
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0308
_diffrn_reflns_av_unetI/netI 0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 23769
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 69.988
_diffrn_reflns_theta_min 2.716
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.738
_reflns_Friedel_fraction_full 0.804
_reflns_Friedel_fraction_max 0.790
_reflns_number_gt 6575
_reflns_number_total 6963
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.647
_refine_diff_density_min -0.589
_refine_diff_density_rms 0.049
_refine_ls_abs_structure_details
;
Flack x determined using 2602 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.01(6)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.068
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 575
_refine_ls_number_reflns 6963
_refine_ls_number_restraints 15
_refine_ls_R_factor_all 0.0459
_refine_ls_R_factor_gt 0.0424
_refine_ls_restrained_S_all 1.070
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.6700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0996
_refine_ls_wR_factor_ref 0.1050
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Restrained distances
C8B-C7A \\sim C8A-C7A
with sigma of 0.002
C9A-C8A \\sim C9B-C8B
with sigma of 0.002
N1A-C10B \\sim N1A-C10A
with sigma of 0.002
C8A-C7A \\sim C8B-C7B
with sigma of 0.002
C7B-C6B \\sim C7A-C6A
with sigma of 0.002
C7A-C3A \\sim C7B-C3A
with sigma of 0.002
N1A-C6A \\sim N1A-C6B
with sigma of 0.002
O1A-H1A \\sim O1W-H1WB \\sim O1W-H1WA \\sim O1-H1
with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uiso(C7B) = Uiso(C7A)
4. Others
Fixed Sof: H3A(0.6) H3AA(0.4) C6A(0.6) H6AA(0.6) H6AB(0.6) C6B(0.4) H6BA(0.4)
H6BB(0.4) C7A(0.6) H7A(0.6) C7B(0.4) H7B(0.4) C8A(0.6) H8A(0.6) C8B(0.4)
H8B(0.4) C9A(0.6) H9AA(0.6) H9AB(0.6) C9B(0.4) H9BA(0.4) H9BB(0.4) C10A(0.4)
H10A(0.4) H10B(0.4) H10C(0.4) C10B(0.6) H10D(0.6) H10E(0.6) H10F(0.6)
5.a Ternary CH refined with riding coordinates:
C1(H1B), C3(H3), C7(H7), C11(H11), C1A(H1AA), C3A(H3A), C3A(H3AA), C7A(H7A),
C7B(H7B), C11A(H11A)
5.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C2A(H2AA,H2AB), C4A(H4AA,
H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C6B(H6BA,H6BB)
5.c Aromatic/amide H refined with riding coordinates:
C8(H8), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C8A(H8A), C8B(H8B),
C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A), C19A(H19A)
5.d X=CH2 refined with riding coordinates:
C9(H9A,H9B), C9A(H9AA,H9AB), C9B(H9BA,H9BB)
5.e Idealised Me refined as rotating group:
C10(H10G,H10H,H10I), C21(H21D,H21E,H21F), C10A(H10A,H10B,H10C), C10B(H10D,
H10E,H10F), C21A(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6445(3) 0.41788(15) 0.92357(14) 0.0350(5) Uani 1 1 d . . . . .
F2 F 0.7190(4) 0.34887(19) 0.81368(16) 0.0537(8) Uani 1 1 d . . . . .
F3 F 0.7413(4) 0.28200(17) 0.93804(18) 0.0547(7) Uani 1 1 d . . . . .
F4 F 0.9186(3) 0.3888(2) 0.9181(2) 0.0624(8) Uani 1 1 d . . . . .
B1 B 0.7602(6) 0.3582(3) 0.8982(3) 0.0315(10) Uani 1 1 d . . . . .
F1A F 0.3196(3) 0.56796(15) 0.46455(15) 0.0370(6) Uani 1 1 d . . . . .
F2A F 0.2843(3) 0.70998(16) 0.44200(17) 0.0425(6) Uani 1 1 d . . . . .
F3A F 0.1693(3) 0.6449(2) 0.54502(15) 0.0469(7) Uani 1 1 d . . . . .
F4A F 0.0634(3) 0.62016(19) 0.41259(15) 0.0460(7) Uani 1 1 d . . . . .
B1A B 0.2093(5) 0.6363(3) 0.4659(3) 0.0278(9) Uani 1 1 d . . . . .
O1 O 0.3702(3) 0.42557(17) 0.79720(15) 0.0262(6) Uani 1 1 d D . . . .
O2 O 0.6831(3) 0.71299(16) 0.55845(15) 0.0232(5) Uani 1 1 d . . . . .
N1 N 0.3192(4) 0.38643(19) 0.61406(18) 0.0224(6) Uani 1 1 d . . . . .
N2 N 0.3725(4) 0.7425(2) 0.83493(18) 0.0217(6) Uani 1 1 d . . . . .
C1 C 0.2826(4) 0.4696(2) 0.6583(2) 0.0183(7) Uani 1 1 d . . . . .
H1B H 0.2964 0.5179 0.6200 0.022 Uiso 1 1 calc R . . . .
C2 C 0.0968(4) 0.4688(3) 0.6715(2) 0.0247(8) Uani 1 1 d . . . . .
H2A H 0.0892 0.4769 0.7306 0.030 Uiso 1 1 calc R . . . .
H2B H 0.0366 0.5165 0.6406 0.030 Uiso 1 1 calc R . . . .
C3 C 0.0149(5) 0.3837(3) 0.6421(2) 0.0300(9) Uani 1 1 d . . . . .
H3 H -0.1033 0.3824 0.6538 0.036 Uiso 1 1 calc R . . . .
C4 C 0.1140(6) 0.3102(3) 0.6876(3) 0.0395(11) Uani 1 1 d . . . . .
H4A H 0.1239 0.3194 0.7477 0.047 Uiso 1 1 calc R . . . .
H4B H 0.0548 0.2554 0.6742 0.047 Uiso 1 1 calc R . . . .
C5 C 0.2878(5) 0.3066(2) 0.6616(3) 0.0337(9) Uani 1 1 d . . . . .
H5A H 0.3736 0.3018 0.7109 0.040 Uiso 1 1 calc R . . . .
H5B H 0.2965 0.2556 0.6268 0.040 Uiso 1 1 calc R . . . .
C6 C 0.1991(4) 0.3850(3) 0.5338(2) 0.0234(7) Uani 1 1 d . . . . .
H6A H 0.2316 0.3385 0.4984 0.028 Uiso 1 1 calc R . . . .
H6B H 0.2067 0.4398 0.5046 0.028 Uiso 1 1 calc R . . . .
C7 C 0.0179(5) 0.3709(2) 0.5493(2) 0.0257(8) Uani 1 1 d . . . . .
H7 H -0.0129 0.3101 0.5355 0.031 Uiso 1 1 calc R . . . .
C8 C -0.0985(5) 0.4273(3) 0.4943(2) 0.0295(8) Uani 1 1 d . . . . .
H8 H -0.0745 0.4867 0.4936 0.035 Uiso 1 1 calc R . . . .
C9 C -0.2326(5) 0.3988(3) 0.4468(3) 0.0383(10) Uani 1 1 d . . . . .
H9A H -0.2594 0.3396 0.4463 0.046 Uiso 1 1 calc R . . . .
H9B H -0.3025 0.4375 0.4129 0.046 Uiso 1 1 calc R . . . .
C10 C 0.4940(5) 0.3847(3) 0.5940(3) 0.0366(10) Uani 1 1 d . . . . .
H10G H 0.5156 0.4372 0.5647 0.055 Uiso 1 1 calc GR . . . .
H10H H 0.5079 0.3350 0.5593 0.055 Uiso 1 1 calc GR . . . .
H10I H 0.5733 0.3807 0.6450 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.4042(4) 0.4857(2) 0.7372(2) 0.0219(7) Uani 1 1 d . . . . .
H11 H 0.5211 0.4766 0.7255 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3881(4) 0.5776(2) 0.7673(2) 0.0197(7) Uani 1 1 d . . . . .
C13 C 0.3137(4) 0.5922(2) 0.8354(2) 0.0236(8) Uani 1 1 d . . . . .
H13 H 0.2643 0.5462 0.8610 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3098(5) 0.6754(2) 0.8678(2) 0.0250(8) Uani 1 1 d . . . . .
H14 H 0.2594 0.6835 0.9160 0.030 Uiso 1 1 calc R . . . .
C15 C 0.4419(4) 0.7299(2) 0.7644(2) 0.0186(7) Uani 1 1 d . . . . .
C16 C 0.5033(4) 0.8029(2) 0.7274(2) 0.0213(7) Uani 1 1 d . . . . .
H16 H 0.4914 0.8579 0.7504 0.026 Uiso 1 1 calc R . . . .
C17 C 0.5796(4) 0.7948(2) 0.6589(2) 0.0214(7) Uani 1 1 d . . . . .
H17 H 0.6197 0.8440 0.6341 0.026 Uiso 1 1 calc R . . . .
C18 C 0.5985(4) 0.7132(2) 0.6251(2) 0.0188(7) Uani 1 1 d . . . . .
C19 C 0.5378(4) 0.6416(2) 0.6577(2) 0.0183(7) Uani 1 1 d . . . . .
H19 H 0.5505 0.5873 0.6334 0.022 Uiso 1 1 calc R . . . .
C20 C 0.4549(4) 0.6482(2) 0.7288(2) 0.0174(7) Uani 1 1 d . . . . .
C21 C 0.7319(5) 0.6317(3) 0.5303(2) 0.0258(8) Uani 1 1 d . . . . .
H21D H 0.8045 0.6400 0.4880 0.039 Uiso 1 1 calc GR . . . .
H21E H 0.6321 0.5995 0.5070 0.039 Uiso 1 1 calc GR . . . .
H21F H 0.7928 0.5998 0.5764 0.039 Uiso 1 1 calc GR . . . .
H1 H 0.465(4) 0.421(3) 0.829(2) 0.032(12) Uiso 1 1 d D . . . .
O1A O -0.1106(3) 0.47171(17) 0.17297(17) 0.0260(6) Uani 1 1 d D . . . .
O2A O 0.2995(3) 0.19175(17) -0.02765(16) 0.0288(6) Uani 1 1 d . . . . .
N1A N 0.1949(4) 0.5444(2) 0.10340(19) 0.0275(7) Uani 1 1 d D . . . .
N2A N 0.0497(4) 0.1730(2) 0.26851(19) 0.0257(7) Uani 1 1 d . . . . .
C1A C 0.1831(4) 0.4701(2) 0.1631(2) 0.0221(7) Uani 1 1 d . . . . .
H1AA H 0.2745 0.4288 0.1557 0.026 Uiso 1 1 calc R . . . .
C2A C 0.2218(6) 0.5061(3) 0.2508(2) 0.0338(9) Uani 1 1 d . . . . .
H2AA H 0.1278 0.4933 0.2814 0.041 Uiso 1 1 calc R . . . .
H2AB H 0.3239 0.4785 0.2799 0.041 Uiso 1 1 calc R . . . .
C3A C 0.2482(6) 0.6026(3) 0.2481(2) 0.0405(11) Uani 1 1 d D . . . .
H3A H 0.2713 0.6264 0.3051 0.049 Uiso 0.6 1 calc R . P A 1
H3AA H 0.2626 0.6247 0.3058 0.049 Uiso 0.4 1 calc R . P B 2
C4A C 0.0919(6) 0.6434(3) 0.2009(3) 0.0375(10) Uani 1 1 d . . . . .
H4AA H -0.0076 0.6267 0.2261 0.045 Uiso 1 1 calc R . . . .
H4AB H 0.1021 0.7065 0.2034 0.045 Uiso 1 1 calc R . . . .
C5A C 0.0711(5) 0.6141(3) 0.1125(2) 0.0303(9) Uani 1 1 d . . . . .
H5AA H -0.0442 0.5926 0.0959 0.036 Uiso 1 1 calc R . . . .
H5AB H 0.0895 0.6628 0.0764 0.036 Uiso 1 1 calc R . . . .
C6A C 0.3664(7) 0.5849(6) 0.1137(6) 0.030(2) Uiso 0.6 1 d D . P C 1
H6AA H 0.3698 0.6320 0.0738 0.036 Uiso 0.6 1 calc R . P C 1
H6AB H 0.4523 0.5420 0.1049 0.036 Uiso 0.6 1 calc R . P C 1
C6B C 0.3706(9) 0.5757(10) 0.1331(9) 0.041(5) Uiso 0.4 1 d D . P C 2
H6BA H 0.4124 0.6049 0.0866 0.049 Uiso 0.4 1 calc R . P C 2
H6BB H 0.4426 0.5250 0.1472 0.049 Uiso 0.4 1 calc R . P C 2
C7A C 0.3976(6) 0.6190(6) 0.2015(3) 0.0418(13) Uiso 0.6 1 d D . P C 1
H7A H 0.3973 0.6825 0.1942 0.050 Uiso 0.6 1 calc R . P C 1
C7B C 0.3940(6) 0.6360(8) 0.2064(4) 0.0418(13) Uiso 0.4 1 d D . P C 2
H7B H 0.3877 0.6982 0.1921 0.050 Uiso 0.4 1 calc R . P C 2
C8A C 0.5837(7) 0.5978(4) 0.2323(4) 0.0260(13) Uani 0.6 1 d D . P C 1
H8A H 0.6624 0.5969 0.1946 0.031 Uiso 0.6 1 calc R . P C 1
C8B C 0.5214(10) 0.6132(6) 0.2832(5) 0.032(2) Uani 0.4 1 d D . P C 2
H8B H 0.4878 0.6202 0.3359 0.038 Uiso 0.4 1 calc R . P C 2
C9A C 0.6328(10) 0.5811(5) 0.3099(4) 0.0315(15) Uiso 0.6 1 d D . P C 1
H9AA H 0.5543 0.5819 0.3477 0.038 Uiso 0.6 1 calc R . P C 1
H9AB H 0.7469 0.5681 0.3284 0.038 Uiso 0.6 1 calc R . P C 1
C9B C 0.6724(11) 0.5850(7) 0.2794(8) 0.034(2) Uiso 0.4 1 d D . P C 2
H9BA H 0.7093 0.5774 0.2276 0.041 Uiso 0.4 1 calc R . P C 2
H9BB H 0.7454 0.5720 0.3285 0.041 Uiso 0.4 1 calc R . P C 2
C10A C 0.2279(14) 0.5047(6) 0.0221(4) 0.030(2) Uiso 0.4 1 d D . P C 1
H10A H 0.3123 0.4596 0.0332 0.046 Uiso 0.4 1 calc GR . P C 1
H10B H 0.2686 0.5490 -0.0123 0.046 Uiso 0.4 1 calc GR . P C 1
H10C H 0.1238 0.4803 -0.0065 0.046 Uiso 0.4 1 calc GR . P C 1
C10B C 0.1401(8) 0.5182(4) 0.0135(3) 0.0243(13) Uiso 0.6 1 d D . P C 2
H10D H 0.2051 0.4684 0.0005 0.037 Uiso 0.6 1 calc GR . P C 2
H10E H 0.1594 0.5659 -0.0227 0.037 Uiso 0.6 1 calc GR . P C 2
H10F H 0.0207 0.5037 0.0055 0.037 Uiso 0.6 1 calc GR . P C 2
C11A C 0.0166(4) 0.4208(2) 0.1462(2) 0.0192(7) Uani 1 1 d . . . . .
H11A H -0.0115 0.4114 0.0856 0.023 Uiso 1 1 calc R . . . .
C12A C 0.0351(4) 0.3345(2) 0.1889(2) 0.0205(7) Uani 1 1 d . . . . .
C13A C -0.0236(4) 0.3223(3) 0.2630(2) 0.0243(8) Uani 1 1 d . . . . .
H13A H -0.0716 0.3687 0.2888 0.029 Uiso 1 1 calc R . . . .
C14A C -0.0120(5) 0.2409(3) 0.3001(2) 0.0274(8) Uani 1 1 d . . . . .
H14A H -0.0515 0.2347 0.3515 0.033 Uiso 1 1 calc R . . . .
C15A C 0.1088(4) 0.1838(2) 0.1950(2) 0.0222(7) Uani 1 1 d . . . . .
C16A C 0.1748(5) 0.1108(2) 0.1594(2) 0.0272(8) Uani 1 1 d . . . . .
H16A H 0.1756 0.0572 0.1867 0.033 Uiso 1 1 calc R . . . .
C17A C 0.2369(5) 0.1164(2) 0.0867(2) 0.0283(8) Uani 1 1 d . . . . .
H17A H 0.2816 0.0670 0.0641 0.034 Uiso 1 1 calc R . . . .
C18A C 0.2348(4) 0.1956(2) 0.0449(2) 0.0230(8) Uani 1 1 d . . . . .
C19A C 0.1694(4) 0.2670(2) 0.0763(2) 0.0202(7) Uani 1 1 d . . . . .
H19A H 0.1661 0.3195 0.0470 0.024 Uiso 1 1 calc R . . . .
C20A C 0.1059(4) 0.2628(2) 0.1527(2) 0.0199(7) Uani 1 1 d . . . . .
C21A C 0.2985(5) 0.2696(3) -0.0740(2) 0.0325(9) Uani 1 1 d . . . . .
H21A H 0.3435 0.2587 -0.1252 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.3678 0.3125 -0.0416 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.1834 0.2909 -0.0867 0.049 Uiso 1 1 calc GR . . . .
H1A H -0.206(4) 0.454(4) 0.148(3) 0.08(2) Uiso 1 1 d D . . . .
O1W O 0.5992(3) 0.40175(17) 0.09350(16) 0.0274(6) Uani 1 1 d D . . . .
H1WA H 0.607(7) 0.399(4) 0.0416(16) 0.065(18) Uiso 1 1 d D . . . .
H1WB H 0.607(7) 0.351(2) 0.115(3) 0.064(18) Uiso 1 1 d D . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0454(13) 0.0213(12) 0.0381(12) -0.0005(10) 0.0050(10) 0.0064(10)
F2 0.0621(18) 0.0569(19) 0.0393(14) -0.0124(13) -0.0016(13) 0.0176(14)
F3 0.076(2) 0.0226(14) 0.0674(19) 0.0060(13) 0.0152(15) 0.0116(13)
F4 0.0326(14) 0.068(2) 0.083(2) -0.0035(18) -0.0054(13) -0.0052(14)
B1 0.032(2) 0.022(2) 0.037(2) -0.0033(19) -0.0019(19) 0.0056(18)
F1A 0.0383(13) 0.0264(13) 0.0479(14) 0.0072(11) 0.0115(11) 0.0048(10)
F2A 0.0481(15) 0.0243(13) 0.0563(16) 0.0022(12) 0.0118(12) -0.0045(11)
F3A 0.0421(14) 0.070(2) 0.0301(12) 0.0026(13) 0.0106(10) 0.0108(13)
F4A 0.0317(12) 0.0644(19) 0.0395(13) 0.0071(13) -0.0026(10) -0.0077(12)
B1A 0.027(2) 0.028(2) 0.027(2) 0.0057(18) 0.0024(16) -0.0008(18)
O1 0.0283(14) 0.0221(14) 0.0271(13) 0.0080(11) 0.0006(11) -0.0026(11)
O2 0.0285(13) 0.0192(14) 0.0237(12) 0.0030(10) 0.0097(10) -0.0013(10)
N1 0.0242(14) 0.0153(15) 0.0291(15) -0.0011(13) 0.0088(12) 0.0006(12)
N2 0.0222(15) 0.0218(16) 0.0209(14) -0.0016(12) 0.0028(12) 0.0021(12)
C1 0.0227(17) 0.0094(16) 0.0235(16) -0.0009(13) 0.0059(13) -0.0013(13)
C2 0.0205(17) 0.031(2) 0.0234(17) -0.0075(16) 0.0073(14) -0.0005(15)
C3 0.0245(18) 0.040(2) 0.0268(19) -0.0041(18) 0.0084(15) -0.0111(17)
C4 0.053(3) 0.037(3) 0.028(2) 0.0051(18) 0.0017(18) -0.025(2)
C5 0.053(3) 0.0128(19) 0.034(2) 0.0027(17) 0.0021(18) -0.0014(17)
C6 0.0301(18) 0.0193(18) 0.0219(17) -0.0012(15) 0.0071(14) -0.0001(15)
C7 0.0295(19) 0.021(2) 0.0266(18) -0.0028(15) 0.0055(15) -0.0051(15)
C8 0.032(2) 0.026(2) 0.032(2) -0.0049(16) 0.0057(15) -0.0002(16)
C9 0.035(2) 0.043(3) 0.035(2) 0.000(2) 0.0003(17) -0.0007(19)
C10 0.027(2) 0.037(2) 0.048(2) -0.013(2) 0.0121(17) 0.0097(18)
C11 0.0219(17) 0.0196(19) 0.0249(18) 0.0035(15) 0.0060(14) -0.0003(14)
C12 0.0184(16) 0.0215(19) 0.0188(16) 0.0002(14) 0.0011(13) -0.0012(13)
C13 0.0259(18) 0.026(2) 0.0189(16) 0.0031(15) 0.0039(14) -0.0035(15)
C14 0.0272(19) 0.028(2) 0.0209(17) -0.0017(16) 0.0068(14) 0.0006(15)
C15 0.0185(16) 0.0193(19) 0.0174(16) -0.0009(14) 0.0001(13) 0.0005(13)
C16 0.0224(17) 0.0151(18) 0.0257(18) -0.0017(14) 0.0008(13) -0.0004(13)
C17 0.0219(17) 0.0169(19) 0.0244(17) 0.0064(14) 0.0001(13) -0.0022(13)
C18 0.0179(16) 0.0198(19) 0.0180(16) 0.0028(14) 0.0001(13) 0.0009(13)
C19 0.0190(16) 0.0164(18) 0.0195(16) -0.0026(13) 0.0026(12) 0.0013(13)
C20 0.0156(16) 0.0185(18) 0.0170(15) 0.0014(13) -0.0016(12) 0.0009(12)
C21 0.0298(19) 0.0215(19) 0.0280(19) 0.0006(16) 0.0109(15) 0.0018(15)
O1A 0.0198(13) 0.0203(14) 0.0388(14) -0.0017(11) 0.0072(11) 0.0028(10)
O2A 0.0371(15) 0.0226(14) 0.0275(13) -0.0034(11) 0.0068(11) 0.0051(11)
N1A 0.0419(19) 0.0181(17) 0.0262(16) -0.0025(13) 0.0173(14) -0.0038(13)
N2A 0.0219(15) 0.0254(18) 0.0286(16) 0.0076(14) -0.0005(12) -0.0035(13)
C1A 0.0220(17) 0.0139(18) 0.0299(18) 0.0039(15) 0.0024(14) 0.0025(13)
C2A 0.048(2) 0.024(2) 0.0245(19) 0.0083(16) -0.0110(17) -0.0113(18)
C3A 0.080(3) 0.020(2) 0.0183(18) -0.0006(16) -0.0038(19) -0.014(2)
C4A 0.052(3) 0.018(2) 0.050(3) -0.0006(18) 0.033(2) 0.0031(18)
C5A 0.030(2) 0.019(2) 0.038(2) 0.0142(17) -0.0050(16) 0.0009(15)
C8A 0.028(3) 0.024(4) 0.028(3) -0.001(3) 0.012(3) -0.001(3)
C8B 0.030(5) 0.022(5) 0.042(6) 0.011(5) 0.001(4) -0.005(4)
C11A 0.0207(16) 0.0157(17) 0.0216(16) -0.0003(14) 0.0048(13) 0.0025(13)
C12A 0.0190(17) 0.0193(19) 0.0225(17) 0.0001(14) 0.0009(13) -0.0022(13)
C13A 0.0215(17) 0.025(2) 0.0260(18) 0.0004(15) 0.0030(14) -0.0021(14)
C14A 0.0238(19) 0.034(2) 0.0249(18) 0.0072(16) 0.0044(14) -0.0039(15)
C15A 0.0192(17) 0.0183(19) 0.0262(18) 0.0038(15) -0.0063(14) -0.0027(13)
C16A 0.0288(19) 0.0164(19) 0.033(2) 0.0049(16) -0.0068(16) -0.0017(14)
C17A 0.0309(19) 0.0164(19) 0.035(2) -0.0045(16) -0.0054(16) 0.0051(15)
C18A 0.0219(18) 0.0206(19) 0.0242(17) -0.0025(15) -0.0039(14) -0.0001(14)
C19A 0.0205(17) 0.0155(18) 0.0229(17) 0.0011(14) -0.0022(13) -0.0008(13)
C20A 0.0175(16) 0.0156(18) 0.0250(17) 0.0015(14) -0.0030(13) -0.0027(13)
C21A 0.040(2) 0.028(2) 0.031(2) -0.0012(18) 0.0123(17) 0.0013(17)
O1W 0.0307(14) 0.0226(16) 0.0291(14) 0.0048(12) 0.0051(11) 0.0021(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.425(5) . ?
F2 B1 1.389(5) . ?
F3 B1 1.378(6) . ?
F4 B1 1.360(6) . ?
F1A B1A 1.393(5) . ?
F2A B1A 1.385(5) . ?
F3A B1A 1.391(5) . ?
F4A B1A 1.386(5) . ?
O1 C11 1.418(4) . ?
O1 H1 0.87(2) . ?
O2 C18 1.372(4) . ?
O2 C21 1.428(4) . ?
N1 C1 1.539(4) . ?
N1 C5 1.513(5) . ?
N1 C6 1.520(5) . ?
N1 C10 1.495(5) . ?
N2 C14 1.314(5) . ?
N2 C15 1.372(4) . ?
C1 H1B 1.0000 . ?
C1 C2 1.546(5) . ?
C1 C11 1.530(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(6) . ?
C3 H3 1.0000 . ?
C3 C4 1.532(6) . ?
C3 C7 1.544(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.536(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.494(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.318(6) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C10 H10G 0.9800 . ?
C10 H10H 0.9800 . ?
C10 H10I 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.531(5) . ?
C12 C13 1.364(5) . ?
C12 C20 1.418(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.408(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.416(5) . ?
C15 C20 1.415(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.365(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.409(5) . ?
C18 C19 1.363(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.431(5) . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
O1A C11A 1.418(4) . ?
O1A H1A 0.87(2) . ?
O2A C18A 1.371(4) . ?
O2A C21A 1.436(5) . ?
N1A C1A 1.534(5) . ?
N1A C5A 1.501(5) . ?
N1A C6A 1.509(6) . ?
N1A C6B 1.513(6) . ?
N1A C10A 1.531(6) . ?
N1A C10B 1.536(6) . ?
N2A C14A 1.311(5) . ?
N2A C15A 1.372(5) . ?
C1A H1AA 1.0000 . ?
C1A C2A 1.538(5) . ?
C1A C11A 1.539(5) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.524(6) . ?
C3A H3A 1.0000 . ?
C3A H3AA 1.0000 . ?
C3A C4A 1.523(7) . ?
C3A C7A 1.541(7) . ?
C3A C7B 1.537(7) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.510(6) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.525(8) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C7B 1.521(8) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.551(7) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.551(7) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.306(7) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.307(7) . ?
C9A H9AA 0.9500 . ?
C9A H9AB 0.9500 . ?
C9B H9BA 0.9500 . ?
C9B H9BB 0.9500 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11A H11A 1.0000 . ?
C11A C12A 1.518(5) . ?
C12A C13A 1.383(5) . ?
C12A C20A 1.428(5) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.410(5) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.420(5) . ?
C15A C20A 1.415(5) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.364(6) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.416(5) . ?
C18A C19A 1.367(5) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.425(5) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
O1W H1WA 0.87(2) . ?
O1W H1WB 0.87(2) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 B1 F1 106.8(3) . . ?
F3 B1 F1 107.8(4) . . ?
F3 B1 F2 111.0(4) . . ?
F4 B1 F1 109.4(4) . . ?
F4 B1 F2 111.0(4) . . ?
F4 B1 F3 110.8(4) . . ?
F2A B1A F1A 109.1(3) . . ?
F2A B1A F3A 110.8(4) . . ?
F2A B1A F4A 109.7(3) . . ?
F3A B1A F1A 108.9(3) . . ?
F4A B1A F1A 109.7(4) . . ?
F4A B1A F3A 108.6(3) . . ?
C11 O1 H1 103(3) . . ?
C18 O2 C21 117.0(3) . . ?
C5 N1 C1 113.3(3) . . ?
C5 N1 C6 107.6(3) . . ?
C6 N1 C1 106.3(3) . . ?
C10 N1 C1 111.8(3) . . ?
C10 N1 C5 109.4(3) . . ?
C10 N1 C6 108.2(3) . . ?
C14 N2 C15 117.5(3) . . ?
N1 C1 H1B 107.1 . . ?
N1 C1 C2 108.4(3) . . ?
C2 C1 H1B 107.1 . . ?
C11 C1 N1 113.3(3) . . ?
C11 C1 H1B 107.1 . . ?
C11 C1 C2 113.5(3) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.2(3) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3 109.7 . . ?
C2 C3 C7 110.9(3) . . ?
C4 C3 C2 109.0(3) . . ?
C4 C3 H3 109.7 . . ?
C4 C3 C7 107.7(3) . . ?
C7 C3 H3 109.7 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 109.1(3) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
N1 C5 C4 110.1(3) . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N1 C6 C7 111.2(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C3 C7 H7 108.0 . . ?
C6 C7 C3 107.2(3) . . ?
C6 C7 H7 108.0 . . ?
C8 C7 C3 115.1(3) . . ?
C8 C7 C6 110.2(3) . . ?
C8 C7 H7 108.0 . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.4(4) . . ?
C9 C8 H8 118.3 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
N1 C10 H10G 109.5 . . ?
N1 C10 H10H 109.5 . . ?
N1 C10 H10I 109.5 . . ?
H10G C10 H10H 109.5 . . ?
H10G C10 H10I 109.5 . . ?
H10H C10 H10I 109.5 . . ?
O1 C11 C1 108.4(3) . . ?
O1 C11 H11 108.8 . . ?
O1 C11 C12 111.3(3) . . ?
C1 C11 H11 108.8 . . ?
C1 C11 C12 110.8(3) . . ?
C12 C11 H11 108.8 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 C20 118.5(3) . . ?
C20 C12 C11 122.1(3) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
N2 C14 C13 123.4(3) . . ?
N2 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N2 C15 C16 117.3(3) . . ?
N2 C15 C20 122.9(3) . . ?
C20 C15 C16 119.8(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
O2 C18 C17 114.3(3) . . ?
C19 C18 O2 124.1(3) . . ?
C19 C18 C17 121.5(3) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C12 C20 C19 124.1(3) . . ?
C15 C20 C12 117.5(3) . . ?
C15 C20 C19 118.4(3) . . ?
O2 C21 H21D 109.5 . . ?
O2 C21 H21E 109.5 . . ?
O2 C21 H21F 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C11A O1A H1A 108(4) . . ?
C18A O2A C21A 116.8(3) . . ?
C1A N1A C10B 112.2(3) . . ?
C5A N1A C1A 112.5(3) . . ?
C5A N1A C6A 107.3(4) . . ?
C5A N1A C6B 109.9(6) . . ?
C5A N1A C10A 125.7(5) . . ?
C5A N1A C10B 100.7(4) . . ?
C6A N1A C1A 112.8(5) . . ?
C6A N1A C10A 89.8(5) . . ?
C6B N1A C1A 100.4(7) . . ?
C6B N1A C10B 121.6(6) . . ?
C10A N1A C1A 106.6(5) . . ?
C14A N2A C15A 116.7(3) . . ?
N1A C1A H1AA 107.2 . . ?
N1A C1A C2A 107.4(3) . . ?
N1A C1A C11A 113.4(3) . . ?
C2A C1A H1AA 107.2 . . ?
C2A C1A C11A 114.0(3) . . ?
C11A C1A H1AA 107.2 . . ?
C1A C2A H2AA 109.6 . . ?
C1A C2A H2AB 109.6 . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A C1A 110.3(3) . . ?
C3A C2A H2AA 109.6 . . ?
C3A C2A H2AB 109.6 . . ?
C2A C3A H3A 110.5 . . ?
C2A C3A H3AA 108.2 . . ?
C2A C3A C7A 107.6(5) . . ?
C2A C3A C7B 118.0(6) . . ?
C4A C3A C2A 108.7(4) . . ?
C4A C3A H3A 110.5 . . ?
C4A C3A H3AA 108.2 . . ?
C4A C3A C7A 109.1(4) . . ?
C4A C3A C7B 105.1(4) . . ?
C7A C3A H3A 110.5 . . ?
C7B C3A H3AA 108.2 . . ?
C3A C4A H4AA 109.8 . . ?
C3A C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.2 . . ?
C5A C4A C3A 109.4(3) . . ?
C5A C4A H4AA 109.8 . . ?
C5A C4A H4AB 109.8 . . ?
N1A C5A C4A 109.5(3) . . ?
N1A C5A H5AA 109.8 . . ?
N1A C5A H5AB 109.8 . . ?
C4A C5A H5AA 109.8 . . ?
C4A C5A H5AB 109.8 . . ?
H5AA C5A H5AB 108.2 . . ?
N1A C6A H6AA 110.5 . . ?
N1A C6A H6AB 110.5 . . ?
N1A C6A C7A 106.1(5) . . ?
H6AA C6A H6AB 108.7 . . ?
C7A C6A H6AA 110.5 . . ?
C7A C6A H6AB 110.5 . . ?
N1A C6B H6BA 108.0 . . ?
N1A C6B H6BB 108.0 . . ?
N1A C6B C7B 117.3(7) . . ?
H6BA C6B H6BB 107.2 . . ?
C7B C6B H6BA 108.0 . . ?
C7B C6B H6BB 108.0 . . ?
C3A C7A H7A 103.7 . . ?
C3A C7A C8A 126.3(4) . . ?
C6A C7A C3A 112.2(5) . . ?
C6A C7A H7A 103.7 . . ?
C6A C7A C8A 104.8(5) . . ?
C8A C7A H7A 103.7 . . ?
C3A C7B H7B 114.8 . . ?
C3A C7B C8B 91.1(4) . . ?
C6B C7B C3A 97.3(8) . . ?
C6B C7B H7B 114.8 . . ?
C6B C7B C8B 119.7(9) . . ?
C8B C7B H7B 114.8 . . ?
C7A C8A H8A 119.8 . . ?
C9A C8A C7A 120.3(6) . . ?
C9A C8A H8A 119.8 . . ?
C7B C8B H8B 118.2 . . ?
C9B C8B C7B 123.5(9) . . ?
C9B C8B H8B 118.2 . . ?
C8A C9A H9AA 120.0 . . ?
C8A C9A H9AB 120.0 . . ?
H9AA C9A H9AB 120.0 . . ?
C8B C9B H9BA 120.0 . . ?
C8B C9B H9BB 120.0 . . ?
H9BA C9B H9BB 120.0 . . ?
N1A C10A H10A 109.5 . . ?
N1A C10A H10B 109.5 . . ?
N1A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N1A C10B H10D 109.5 . . ?
N1A C10B H10E 109.5 . . ?
N1A C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O1A C11A C1A 108.4(3) . . ?
O1A C11A H11A 108.7 . . ?
O1A C11A C12A 112.5(3) . . ?
C1A C11A H11A 108.7 . . ?
C12A C11A C1A 109.7(3) . . ?
C12A C11A H11A 108.7 . . ?
C13A C12A C11A 120.4(3) . . ?
C13A C12A C20A 117.8(3) . . ?
C20A C12A C11A 121.7(3) . . ?
C12A C13A H13A 120.1 . . ?
C12A C13A C14A 119.8(4) . . ?
C14A C13A H13A 120.1 . . ?
N2A C14A C13A 124.4(3) . . ?
N2A C14A H14A 117.8 . . ?
C13A C14A H14A 117.8 . . ?
N2A C15A C16A 117.5(3) . . ?
N2A C15A C20A 123.9(3) . . ?
C20A C15A C16A 118.6(3) . . ?
C15A C16A H16A 119.5 . . ?
C17A C16A C15A 121.1(3) . . ?
C17A C16A H16A 119.5 . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 120.1(4) . . ?
C18A C17A H17A 120.0 . . ?
O2A C18A C17A 113.9(3) . . ?
C19A C18A O2A 125.5(3) . . ?
C19A C18A C17A 120.6(3) . . ?
C18A C19A H19A 119.9 . . ?
C18A C19A C20A 120.2(3) . . ?
C20A C19A H19A 119.9 . . ?
C15A C20A C12A 117.4(3) . . ?
C15A C20A C19A 119.4(3) . . ?
C19A C20A C12A 123.2(3) . . ?
O2A C21A H21A 109.5 . . ?
O2A C21A H21B 109.5 . . ?
O2A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
H1WA O1W H1WB 111(6) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 F1 0.87(2) 1.97(3) 2.812(3) 166(4) .
O1A H1A O1W 0.87(2) 1.88(3) 2.740(4) 173(6) 1_455
O1W H1WA F1 0.87(2) 2.03(3) 2.881(4) 168(6) 1_554
O1W H1WB N2 0.87(2) 1.88(3) 2.750(4) 179(6) 2_646
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C11 O1 -70.8(3) . . . . ?
C1 C2 C3 C4 56.7(4) . . . . ?
C1 C2 C3 C7 -61.7(4) . . . . ?
C1 C11 C12 C13 107.5(4) . . . . ?
C1 C11 C12 C20 -75.4(4) . . . . ?
C2 C1 N1 C5 -59.5(4) . . . . ?
C2 C1 N1 C6 58.4(3) . . . . ?
C2 C1 N1 C10 176.3(3) . . . . ?
C2 C1 C11 O1 53.4(4) . . . . ?
C2 C1 C11 C12 -68.9(4) . . . . ?
C2 C3 C4 C5 -66.3(4) . . . . ?
C2 C3 C7 C6 51.5(4) . . . . ?
C2 C3 C7 C8 -71.5(4) . . . . ?
C3 C2 C1 N1 4.0(4) . . . . ?
C3 C2 C1 C11 -122.9(3) . . . . ?
C3 C4 C5 N1 11.8(5) . . . . ?
C3 C7 C6 N1 12.8(4) . . . . ?
C3 C7 C8 C9 -110.8(4) . . . . ?
C4 C3 C7 C6 -67.8(4) . . . . ?
C4 C3 C7 C8 169.2(3) . . . . ?
C4 C5 N1 C1 50.7(4) . . . . ?
C4 C5 N1 C6 -66.5(4) . . . . ?
C4 C5 N1 C10 176.1(3) . . . . ?
C5 C4 C3 C7 54.1(4) . . . . ?
C6 C7 C8 C9 127.8(4) . . . . ?
C7 C6 N1 C1 -69.7(3) . . . . ?
C7 C6 N1 C5 52.0(4) . . . . ?
C7 C6 N1 C10 170.1(3) . . . . ?
C8 C7 C6 N1 138.7(3) . . . . ?
C11 C1 N1 C5 67.4(4) . . . . ?
C11 C1 N1 C6 -174.6(3) . . . . ?
C11 C1 N1 C10 -56.7(4) . . . . ?
C12 C11 C1 N1 166.9(3) . . . . ?
C13 C12 C11 O1 -13.2(4) . . . . ?
C17 C18 O2 C21 169.4(3) . . . . ?
C19 C18 O2 C21 -10.0(5) . . . . ?
C20 C12 C11 O1 163.9(3) . . . . ?
N1A C1A C11A O1A -74.2(3) . . . . ?
C1A C11A C12A C13A 100.0(4) . . . . ?
C1A C11A C12A C20A -82.8(4) . . . . ?
C2A C1A C11A O1A 49.1(4) . . . . ?
C2A C1A C11A C12A -74.0(4) . . . . ?
C3A C2A C1A N1A 3.2(5) . . . . ?
C3A C2A C1A C11A -123.3(4) . . . . ?
C12A C11A C1A N1A 162.7(3) . . . . ?
C13A C12A C11A O1A -20.8(5) . . . . ?
C20A C12A C11A O1A 156.4(3) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
TITL 17srv201 in P21 #4
REM reset to P21 #4
CELL 1.54178 8.0721 15.6353 16.4422 90 98.2832 90
ZERR 4 0.0002 0.0005 0.0005 0 0.0014 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H B F N O
UNIT 84 112 4 16 8 10
EQIV $1 -1+X,+Y,+Z
EQIV $2 +X,+Y,-1+Z
EQIV $3 1-X,-0.5+Y,1-Z
SADI 0.002 C8B C7A C8A C7A
SADI 0.002 C9A C8A C9B C8B
SADI 0.002 N1A C10B N1A C10A
SADI 0.002 C8A C7A C8B C7B
SADI 0.002 C7B C6B C7A C6A
SADI 0.002 C7A C3A C7B C3A
SADI 0.002 N1A C6A N1A C6B
SADI 0.002 O1A H1A O1W H1Wb O1W H1Wa O1 H1
EADP C7B C7A
L.S. 9
PLAN 5
SIZE 0.09 0.26 0.42
TEMP -153.15
HTAB O1 F1
HTAB O1A O1W_$1
HTAB O1W F1_$2
HTAB O1W N2_$3
CONF C2 C1 N1 C5
CONF C11 C1 N1 C5
CONF C2 C1 N1 C6
CONF C11 C1 N1 C6
CONF C2 C1 N1 C10
CONF C11 C1 N1 C10
CONF C3 C2 C1 N1
CONF C3 C2 C1 C11
CONF C1 C2 C3 C4
CONF C1 C2 C3 C7
CONF C2 C3 C7 C6
CONF C4 C3 C7 C6
CONF C2 C3 C7 C8
CONF C4 C3 C7 C8
CONF C3 C7 C6 N1
CONF C8 C7 C6 N1
CONF C7 C6 N1 C1
CONF C7 C6 N1 C5
CONF C7 C6 N1 C10
CONF C4 C5 N1 C1
CONF C4 C5 N1 C6
CONF C4 C5 N1 C10
CONF C3 C4 C5 N1
CONF C2 C3 C4 C5
CONF C5 C4 C3 C7
CONF C3 C7 C8 C9
CONF C6 C7 C8 C9
CONF N1 C1 C11 O1
CONF C2 C1 C11 O1
CONF C12 C11 C1 N1
CONF C2 C1 C11 C12
CONF C13 C12 C11 O1
CONF C1 C11 C12 C13
CONF C20 C12 C11 O1
CONF C1 C11 C12 C20
CONF C17 C18 O2 C21
CONF C19 C18 O2 C21
CONF N1A C1A C11A O1A
CONF C12A C11A C1A N1A
CONF C2A C1A C11A O1A
CONF C2A C1A C11A C12A
CONF C13A C12A C11A O1A
CONF C1A C11A C12A C13A
CONF C20A C12A C11A O1A
CONF C1A C11A C12A C20A
CONF C3A C2A C1A N1A
CONF C3A C2A C1A C11A
BOND $h
fmap 2
acta
OMIT -2 140
OMIT 0 -6 2
OMIT 4 -4 12
OMIT 0 12 11
WGHT 0.04 1.67
FVAR 0.27005
REM
REM
REM
F1 4 0.64453 0.41788 0.92357 11.00000 0.04542 0.02132 0.03808 =
-0.00054 0.00496 0.00635
F2 4 0.71900 0.34887 0.81368 11.00000 0.06215 0.05692 0.03936 =
-0.01235 -0.00161 0.01761
F3 4 0.74130 0.28200 0.93804 11.00000 0.07561 0.02255 0.06745 =
0.00604 0.01521 0.01162
F4 4 0.91856 0.38881 0.91809 11.00000 0.03260 0.06771 0.08278 =
-0.00355 -0.00541 -0.00521
B1 3 0.76021 0.35816 0.89821 11.00000 0.03245 0.02246 0.03747 =
-0.00326 -0.00195 0.00554
F1A 4 0.31961 0.56796 0.46455 11.00000 0.03836 0.02638 0.04797 =
0.00725 0.01146 0.00476
F2A 4 0.28426 0.70998 0.44200 11.00000 0.04815 0.02436 0.05634 =
0.00219 0.01179 -0.00454
F3A 4 0.16935 0.64486 0.54501 11.00000 0.04216 0.06993 0.03011 =
0.00256 0.01056 0.01076
F4A 4 0.06339 0.62016 0.41259 11.00000 0.03169 0.06444 0.03956 =
0.00710 -0.00258 -0.00765
B1A 3 0.20927 0.63627 0.46592 11.00000 0.02749 0.02813 0.02732 =
0.00571 0.00236 -0.00087
O1 6 0.37019 0.42557 0.79720 11.00000 0.02829 0.02212 0.02709 =
0.00798 0.00061 -0.00259
O2 6 0.68307 0.71299 0.55845 11.00000 0.02853 0.01921 0.02374 =
0.00302 0.00967 -0.00131
N1 5 0.31917 0.38643 0.61406 11.00000 0.02419 0.01535 0.02908 =
-0.00111 0.00875 0.00063
N2 5 0.37249 0.74248 0.83492 11.00000 0.02225 0.02176 0.02090 =
-0.00155 0.00283 0.00208
C1 1 0.28257 0.46961 0.65829 11.00000 0.02270 0.00941 0.02352 =
-0.00086 0.00590 -0.00135
AFIX 13
H1b 2 0.29642 0.51790 0.61997 11.00000 -1.20000
AFIX 0
C2 1 0.09679 0.46880 0.67152 11.00000 0.02045 0.03145 0.02336 =
-0.00751 0.00733 -0.00051
AFIX 23
H2a 2 0.08916 0.47692 0.73058 11.00000 -1.20000
H2b 2 0.03664 0.51655 0.64063 11.00000 -1.20000
AFIX 0
C3 1 0.01487 0.38371 0.64215 11.00000 0.02455 0.03991 0.02682 =
-0.00407 0.00836 -0.01112
AFIX 13
H3 2 -0.10334 0.38243 0.65377 11.00000 -1.20000
AFIX 0
C4 1 0.11398 0.31023 0.68759 11.00000 0.05267 0.03659 0.02808 =
0.00507 0.00166 -0.02497
AFIX 23
H4a 2 0.12392 0.31941 0.74767 11.00000 -1.20000
H4b 2 0.05481 0.25544 0.67425 11.00000 -1.20000
AFIX 0
C5 1 0.28780 0.30662 0.66158 11.00000 0.05305 0.01284 0.03415 =
0.00267 0.00209 -0.00141
AFIX 23
H5a 2 0.37356 0.30180 0.71087 11.00000 -1.20000
H5b 2 0.29650 0.25555 0.62684 11.00000 -1.20000
AFIX 0
C6 1 0.19910 0.38496 0.53382 11.00000 0.03015 0.01930 0.02190 =
-0.00124 0.00711 -0.00005
AFIX 23
H6a 2 0.23163 0.33853 0.49836 11.00000 -1.20000
H6b 2 0.20673 0.43984 0.50457 11.00000 -1.20000
AFIX 0
C7 1 0.01786 0.37088 0.54928 11.00000 0.02954 0.02142 0.02662 =
-0.00277 0.00550 -0.00512
AFIX 13
H7 2 -0.01289 0.31010 0.53546 11.00000 -1.20000
AFIX 0
C8 1 -0.09847 0.42728 0.49430 11.00000 0.03155 0.02557 0.03181 =
-0.00488 0.00571 -0.00022
AFIX 43
H8 2 -0.07451 0.48674 0.49355 11.00000 -1.20000
AFIX 0
C9 1 -0.23262 0.39882 0.44677 11.00000 0.03470 0.04351 0.03543 =
-0.00033 0.00026 -0.00067
AFIX 93
H9a 2 -0.25944 0.33964 0.44634 11.00000 -1.20000
H9b 2 -0.30248 0.43748 0.41293 11.00000 -1.20000
AFIX 0
C10 1 0.49404 0.38470 0.59402 11.00000 0.02697 0.03665 0.04814 =
-0.01278 0.01205 0.00974
AFIX 137
H10g 2 0.51559 0.43718 0.56469 11.00000 -1.50000
H10h 2 0.50787 0.33504 0.55926 11.00000 -1.50000
H10i 2 0.57327 0.38073 0.64497 11.00000 -1.50000
AFIX 0
C11 1 0.40415 0.48570 0.73715 11.00000 0.02188 0.01957 0.02493 =
0.00354 0.00604 -0.00030
AFIX 13
H11 2 0.52107 0.47661 0.72548 11.00000 -1.20000
AFIX 0
C12 1 0.38806 0.57759 0.76730 11.00000 0.01841 0.02148 0.01884 =
0.00018 0.00108 -0.00122
C13 1 0.31366 0.59223 0.83540 11.00000 0.02587 0.02629 0.01893 =
0.00305 0.00388 -0.00347
AFIX 43
H13 2 0.26430 0.54618 0.86099 11.00000 -1.20000
AFIX 0
C14 1 0.30984 0.67540 0.86784 11.00000 0.02726 0.02794 0.02086 =
-0.00175 0.00684 0.00060
AFIX 43
H14 2 0.25937 0.68347 0.91603 11.00000 -1.20000
AFIX 0
C15 1 0.44186 0.72992 0.76442 11.00000 0.01854 0.01927 0.01737 =
-0.00088 0.00009 0.00054
C16 1 0.50332 0.80287 0.72735 11.00000 0.02239 0.01507 0.02567 =
-0.00169 0.00082 -0.00041
AFIX 43
H16 2 0.49138 0.85788 0.75035 11.00000 -1.20000
AFIX 0
C17 1 0.57956 0.79479 0.65887 11.00000 0.02187 0.01691 0.02445 =
0.00639 0.00007 -0.00219
AFIX 43
H17 2 0.61973 0.84404 0.63407 11.00000 -1.20000
AFIX 0
C18 1 0.59852 0.71320 0.62507 11.00000 0.01795 0.01983 0.01805 =
0.00284 0.00011 0.00093
C19 1 0.53778 0.64156 0.65773 11.00000 0.01903 0.01639 0.01953 =
-0.00256 0.00265 0.00129
AFIX 43
H19 2 0.55046 0.58730 0.63336 11.00000 -1.20000
AFIX 0
C20 1 0.45491 0.64823 0.72878 11.00000 0.01565 0.01851 0.01701 =
0.00136 -0.00163 0.00095
C21 1 0.73194 0.63170 0.53026 11.00000 0.02984 0.02151 0.02799 =
0.00059 0.01093 0.00177
AFIX 137
H21d 2 0.80454 0.64003 0.48800 11.00000 -1.50000
H21e 2 0.63207 0.59955 0.50697 11.00000 -1.50000
H21f 2 0.79277 0.59974 0.57646 11.00000 -1.50000
AFIX 0
H1 2 0.46472 0.42145 0.82936 11.00000 0.03229
O1A 6 -0.11063 0.47171 0.17297 11.00000 0.01982 0.02034 0.03881 =
-0.00166 0.00721 0.00275
O2A 6 0.29953 0.19175 -0.02764 11.00000 0.03707 0.02260 0.02754 =
-0.00337 0.00684 0.00515
N1A 5 0.19493 0.54442 0.10340 11.00000 0.04190 0.01809 0.02623 =
-0.00248 0.01728 -0.00381
N2A 5 0.04972 0.17298 0.26851 11.00000 0.02189 0.02545 0.02860 =
0.00761 -0.00054 -0.00351
C1A 1 0.18311 0.47006 0.16311 11.00000 0.02199 0.01395 0.02991 =
0.00386 0.00235 0.00245
AFIX 13
H1Aa 2 0.27451 0.42884 0.15574 11.00000 -1.20000
AFIX 0
C2A 1 0.22183 0.50614 0.25078 11.00000 0.04815 0.02383 0.02455 =
0.00824 -0.01104 -0.01125
AFIX 23
H2Aa 2 0.12781 0.49331 0.28142 11.00000 -1.20000
H2Ab 2 0.32387 0.47852 0.27987 11.00000 -1.20000
AFIX 0
C3A 1 0.24820 0.60255 0.24811 11.00000 0.07990 0.02007 0.01836 =
-0.00058 -0.00382 -0.01447
PART 1
AFIX 13
H3A 2 0.27132 0.62639 0.30506 10.60000 -1.20000
AFIX 0
PART 0
PART 2
AFIX 13
H3Aa 2 0.26264 0.62468 0.30576 10.40000 -1.20000
AFIX 0
PART 0
C4A 1 0.09186 0.64340 0.20092 11.00000 0.05199 0.01771 0.05021 =
-0.00063 0.03268 0.00310
AFIX 23
H4Aa 2 -0.00760 0.62674 0.22612 11.00000 -1.20000
H4Ab 2 0.10211 0.70648 0.20339 11.00000 -1.20000
AFIX 0
C5A 1 0.07107 0.61412 0.11254 11.00000 0.03039 0.01926 0.03836 =
0.01421 -0.00499 0.00095
AFIX 23
H5Aa 2 -0.04417 0.59258 0.09593 11.00000 -1.20000
H5Ab 2 0.08954 0.66282 0.07643 11.00000 -1.20000
AFIX 0
PART 1
C6A 1 0.36635 0.58489 0.11367 10.60000 0.03021
AFIX 23
H6Aa 2 0.36976 0.63203 0.07375 10.60000 -1.20000
H6Ab 2 0.45231 0.54202 0.10491 10.60000 -1.20000
AFIX 0
PART 0
PART 2
C6B 1 0.37060 0.57569 0.13308 10.40000 0.04093
AFIX 23
H6Ba 2 0.41247 0.60488 0.08663 10.40000 -1.20000
H6Bb 2 0.44258 0.52503 0.14723 10.40000 -1.20000
AFIX 0
PART 0
PART 1
C7A 1 0.39759 0.61899 0.20147 10.60000 0.04180
AFIX 13
H7A 2 0.39733 0.68249 0.19421 10.60000 -1.20000
AFIX 0
PART 0
PART 2
C7B 1 0.39397 0.63605 0.20642 10.40000 0.04180
AFIX 13
H7B 2 0.38770 0.69824 0.19211 10.40000 -1.20000
AFIX 0
PART 0
PART 1
C8A 1 0.58370 0.59777 0.23230 10.60000 0.02842 0.02399 0.02793 =
-0.00093 0.01191 -0.00087
AFIX 43
H8A 2 0.66243 0.59692 0.19457 10.60000 -1.20000
AFIX 0
PART 0
PART 2
C8B 1 0.52138 0.61323 0.28323 10.40000 0.03018 0.02224 0.04152 =
0.01132 0.00106 -0.00460
AFIX 43
H8B 2 0.48780 0.62016 0.33589 10.40000 -1.20000
AFIX 0
PART 0
PART 1
C9A 1 0.63278 0.58106 0.30987 10.60000 0.03147
AFIX 93
H9Aa 2 0.55431 0.58186 0.34773 10.60000 -1.20000
H9Ab 2 0.74695 0.56809 0.32842 10.60000 -1.20000
AFIX 0
PART 0
PART 2
C9B 1 0.67243 0.58500 0.27942 10.40000 0.03386
AFIX 93
H9Ba 2 0.70929 0.57746 0.22756 10.40000 -1.20000
H9Bb 2 0.74538 0.57200 0.32851 10.40000 -1.20000
AFIX 0
PART 0
PART 1
C10A 1 0.22787 0.50474 0.02212 10.40000 0.03046
AFIX 137
H10a 2 0.31221 0.45954 0.03320 10.40000 -1.50000
H10b 2 0.26873 0.54895 -0.01229 10.40000 -1.50000
H10c 2 0.12375 0.48033 -0.00657 10.40000 -1.50000
AFIX 0
PART 0
PART 2
C10B 1 0.14009 0.51823 0.01354 10.60000 0.02434
AFIX 137
H10d 2 0.20505 0.46840 0.00050 10.60000 -1.50000
H10e 2 0.15948 0.56583 -0.02270 10.60000 -1.50000
H10f 2 0.02072 0.50375 0.00548 10.60000 -1.50000
AFIX 0
PART 0
C11A 1 0.01665 0.42084 0.14621 11.00000 0.02066 0.01577 0.02157 =
-0.00028 0.00484 0.00254
AFIX 13
H11A 2 -0.01150 0.41135 0.08565 11.00000 -1.20000
AFIX 0
C12A 1 0.03506 0.33454 0.18886 11.00000 0.01904 0.01932 0.02254 =
0.00011 0.00089 -0.00215
C13A 1 -0.02362 0.32232 0.26297 11.00000 0.02153 0.02527 0.02605 =
0.00042 0.00300 -0.00214
AFIX 43
H13A 2 -0.07162 0.36865 0.28878 11.00000 -1.20000
AFIX 0
C14A 1 -0.01196 0.24085 0.30009 11.00000 0.02378 0.03369 0.02490 =
0.00722 0.00438 -0.00394
AFIX 43
H14A 2 -0.05149 0.23473 0.35147 11.00000 -1.20000
AFIX 0
C15A 1 0.10878 0.18380 0.19498 11.00000 0.01924 0.01834 0.02625 =
0.00384 -0.00630 -0.00270
C16A 1 0.17476 0.11081 0.15943 11.00000 0.02883 0.01637 0.03313 =
0.00492 -0.00678 -0.00173
AFIX 43
H16A 2 0.17564 0.05723 0.18674 11.00000 -1.20000
AFIX 0
C17A 1 0.23688 0.11636 0.08674 11.00000 0.03094 0.01645 0.03454 =
-0.00451 -0.00540 0.00510
AFIX 43
H17A 2 0.28161 0.06700 0.06414 11.00000 -1.20000
AFIX 0
C18A 1 0.23477 0.19562 0.04489 11.00000 0.02191 0.02066 0.02421 =
-0.00250 -0.00389 -0.00007
C19A 1 0.16937 0.26695 0.07627 11.00000 0.02052 0.01549 0.02295 =
0.00107 -0.00225 -0.00076
AFIX 43
H19A 2 0.16616 0.31948 0.04705 11.00000 -1.20000
AFIX 0
C20A 1 0.10595 0.26276 0.15271 11.00000 0.01746 0.01555 0.02496 =
0.00150 -0.00305 -0.00272
C21A 1 0.29848 0.26963 -0.07397 11.00000 0.04013 0.02804 0.03140 =
-0.00117 0.01230 0.00130
AFIX 137
H21a 2 0.34351 0.25865 -0.12524 11.00000 -1.50000
H21b 2 0.36780 0.31254 -0.04162 11.00000 -1.50000
H21c 2 0.18343 0.29085 -0.08668 11.00000 -1.50000
AFIX 0
H1A 2 -0.20629 0.45387 0.14816 11.00000 0.07852
O1W 6 0.59920 0.40174 0.09350 11.00000 0.03068 0.02262 0.02912 =
0.00480 0.00513 0.00212
H1Wa 2 0.60649 0.39919 0.04152 11.00000 0.06545
H1Wb 2 0.60708 0.35125 0.11537 11.00000 0.06395
HKLF 4
END
;
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_Me2Qn_17srv202
_database_code_depnum_ccdc_archive 'CCDC 1985988'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-02-24 deposited with the CCDC. 2020-06-09 downloaded from the CCDC.
;
_audit_creation_date 2017-08-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(B F4), C22 H30 N2 O2'
_chemical_formula_sum 'C22 H30 B2 F8 N2 O2'
_chemical_formula_weight 528.10
_chemical_absolute_configuration ad
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 9.6961(3)
_cell_length_b 10.2407(3)
_cell_length_c 23.6533(8)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2348.65(13)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9820
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 74.48
_cell_measurement_theta_min 3.74
_shelx_estimated_absorpt_T_max 0.870
_shelx_estimated_absorpt_T_min 0.653
_exptl_absorpt_coefficient_mu 1.195
_exptl_absorpt_correction_T_max 0.7538
_exptl_absorpt_correction_T_min 0.6617
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8778.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.494
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1096
_exptl_crystal_size_max 0.39
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.12
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0314
_diffrn_reflns_av_unetI/netI 0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_number 27372
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 72.468
_diffrn_reflns_theta_min 3.737
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.731
_reflns_Friedel_fraction_full 0.979
_reflns_Friedel_fraction_max 0.964
_reflns_number_gt 4411
_reflns_number_total 4554
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 0.311
_refine_diff_density_min -0.179
_refine_diff_density_rms 0.033
_refine_ls_abs_structure_details
;
Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.00(3)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 445
_refine_ls_number_reflns 4554
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0268
_refine_ls_R_factor_gt 0.0256
_refine_ls_restrained_S_all 1.067
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0638
_refine_ls_wR_factor_ref 0.0651
_refine_special_details ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.00225(13) 0.67925(13) 0.45672(5) 0.0342(3) Uani 1 1 d . . . . .
F2 F 0.21356(12) 0.67705(12) 0.49781(5) 0.0322(3) Uani 1 1 d . . . . .
F3 F 0.02555(14) 0.73557(13) 0.54922(5) 0.0377(3) Uani 1 1 d . . . . .
F4 F 0.05660(14) 0.52419(12) 0.52173(6) 0.0378(3) Uani 1 1 d . . . . .
B1 B 0.0734(2) 0.6544(2) 0.50688(9) 0.0236(4) Uani 1 1 d . . . . .
F5 F 0.59403(13) 0.51518(12) 0.67169(5) 0.0327(3) Uani 1 1 d . . . . .
F6 F 0.81417(13) 0.44283(15) 0.67660(5) 0.0412(3) Uani 1 1 d . . . . .
F7 F 0.69877(13) 0.49848(13) 0.75681(5) 0.0362(3) Uani 1 1 d . . . . .
F8 F 0.63772(14) 0.31504(11) 0.70792(5) 0.0345(3) Uani 1 1 d . . . . .
B2 B 0.6869(2) 0.4416(2) 0.70330(9) 0.0226(4) Uani 1 1 d . . . . .
O1 O 0.35231(13) 0.54639(13) 0.40969(6) 0.0227(3) Uani 1 1 d . . . . .
O2 O -0.29723(14) 0.36533(16) 0.41068(7) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.19834(16) 0.61718(14) 0.29655(7) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.18751(19) 0.09305(15) 0.44419(7) 0.0256(4) Uani 1 1 d . . . . .
C1 C 0.22640(17) 0.48527(16) 0.32510(7) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.36107(19) 0.42932(17) 0.29997(8) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.42923(19) 0.52798(19) 0.26075(8) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.4511(2) 0.6567(2) 0.29240(10) 0.0325(5) Uani 1 1 d . . . . .
C5 C 0.3116(2) 0.71561(18) 0.30739(9) 0.0281(4) Uani 1 1 d . . . . .
C6 C 0.1911(2) 0.59092(19) 0.23312(8) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.3343(2) 0.5555(2) 0.20984(8) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.3385(2) 0.4471(2) 0.16751(9) 0.0318(5) Uani 1 1 d . . . . .
C9 C 0.2365(3) 0.3731(2) 0.14960(11) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.0623(2) 0.6727(2) 0.31445(9) 0.0267(4) Uani 1 1 d . . . . .
C11 C 0.22680(18) 0.49191(17) 0.39035(7) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.20890(19) 0.35264(17) 0.41201(7) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.3235(2) 0.28026(18) 0.42538(8) 0.0226(4) Uani 1 1 d . . . . .
C14 C 0.3101(2) 0.14966(19) 0.44081(8) 0.0262(4) Uani 1 1 d . . . . .
C15 C 0.0675(2) 0.16144(18) 0.43412(7) 0.0237(4) Uani 1 1 d . . . . .
C16 C -0.0630(2) 0.1010(2) 0.43976(8) 0.0301(5) Uani 1 1 d . . . . .
C17 C -0.1797(2) 0.1710(2) 0.43084(9) 0.0318(5) Uani 1 1 d . . . . .
C18 C -0.1736(2) 0.3049(2) 0.41539(8) 0.0263(4) Uani 1 1 d . . . . .
C19 C -0.0478(2) 0.36418(19) 0.40776(8) 0.0221(4) Uani 1 1 d . . . . .
C20 C 0.0759(2) 0.29458(17) 0.41730(7) 0.0194(4) Uani 1 1 d . . . . .
C21 C -0.2956(2) 0.5006(2) 0.39436(9) 0.0323(5) Uani 1 1 d . . . . .
C22 C 0.1816(3) -0.0485(2) 0.45752(10) 0.0362(5) Uani 1 1 d . . . . .
H1 H 0.329(3) 0.596(3) 0.4374(13) 0.046(8) Uiso 1 1 d . . . . .
H1A H 0.148(2) 0.434(2) 0.3139(9) 0.017(5) Uiso 1 1 d . . . . .
H2A H 0.337(2) 0.349(2) 0.2801(10) 0.026(6) Uiso 1 1 d . . . . .
H2B H 0.427(2) 0.411(2) 0.3303(10) 0.020(5) Uiso 1 1 d . . . . .
H3 H 0.515(2) 0.495(2) 0.2471(9) 0.022(5) Uiso 1 1 d . . . . .
H4A H 0.503(3) 0.641(3) 0.3282(13) 0.046(8) Uiso 1 1 d . . . . .
H4B H 0.501(3) 0.716(3) 0.2675(11) 0.037(7) Uiso 1 1 d . . . . .
H5A H 0.300(2) 0.740(2) 0.3476(10) 0.023(5) Uiso 1 1 d . . . . .
H5B H 0.287(3) 0.791(3) 0.2853(11) 0.031(6) Uiso 1 1 d . . . . .
H6A H 0.123(3) 0.520(3) 0.2285(10) 0.030(6) Uiso 1 1 d . . . . .
H6B H 0.158(3) 0.672(2) 0.2155(10) 0.028(6) Uiso 1 1 d . . . . .
H7 H 0.367(3) 0.635(3) 0.1895(11) 0.039(7) Uiso 1 1 d . . . . .
H8 H 0.436(3) 0.433(3) 0.1505(12) 0.047(8) Uiso 1 1 d . . . . .
H9A H 0.255(2) 0.308(2) 0.1228(10) 0.025(6) Uiso 1 1 d . . . . .
H9B H 0.142(4) 0.383(3) 0.1625(15) 0.062(9) Uiso 1 1 d . . . . .
H10A H 0.050(2) 0.752(2) 0.2924(10) 0.025(6) Uiso 1 1 d . . . . .
H10B H 0.068(3) 0.694(3) 0.3545(11) 0.034(6) Uiso 1 1 d . . . . .
H10C H -0.011(3) 0.606(3) 0.3060(10) 0.030(6) Uiso 1 1 d . . . . .
H11 H 0.152(2) 0.542(2) 0.4045(8) 0.014(5) Uiso 1 1 d . . . . .
H13 H 0.417(2) 0.319(2) 0.4240(9) 0.022(5) Uiso 1 1 d . . . . .
H14 H 0.383(3) 0.099(3) 0.4490(10) 0.029(6) Uiso 1 1 d . . . . .
H16 H -0.065(3) 0.009(3) 0.4511(11) 0.041(7) Uiso 1 1 d . . . . .
H17 H -0.268(3) 0.130(3) 0.4342(11) 0.037(7) Uiso 1 1 d . . . . .
H19 H -0.042(2) 0.456(2) 0.3986(8) 0.015(5) Uiso 1 1 d . . . . .
H21A H -0.395(3) 0.533(3) 0.3991(11) 0.037(7) Uiso 1 1 d . . . . .
H21B H -0.266(3) 0.510(3) 0.3555(12) 0.040(7) Uiso 1 1 d . . . . .
H21C H -0.234(3) 0.557(3) 0.4214(12) 0.041(7) Uiso 1 1 d . . . . .
H22A H 0.121(3) -0.062(2) 0.4904(12) 0.038(7) Uiso 1 1 d . . . . .
H22B H 0.133(3) -0.095(2) 0.4276(11) 0.030(6) Uiso 1 1 d . . . . .
H22C H 0.279(3) -0.078(3) 0.4643(13) 0.050(8) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0360(7) 0.0361(7) 0.0304(6) -0.0044(5) -0.0030(5) 0.0104(5)
F2 0.0274(6) 0.0309(6) 0.0385(6) -0.0063(5) 0.0072(5) -0.0056(5)
F3 0.0376(7) 0.0415(7) 0.0341(7) -0.0151(6) 0.0044(5) 0.0080(6)
F4 0.0438(7) 0.0238(6) 0.0458(7) 0.0053(5) 0.0015(6) -0.0094(6)
B1 0.0262(10) 0.0197(9) 0.0250(10) -0.0021(8) 0.0028(9) -0.0009(9)
F5 0.0338(6) 0.0301(6) 0.0342(6) 0.0042(5) -0.0051(5) 0.0038(5)
F6 0.0220(6) 0.0679(9) 0.0336(6) -0.0129(6) 0.0015(5) -0.0052(6)
F7 0.0467(7) 0.0400(7) 0.0221(5) -0.0067(5) 0.0001(5) -0.0106(6)
F8 0.0429(7) 0.0192(5) 0.0414(7) -0.0032(5) 0.0026(6) 0.0016(5)
B2 0.0211(10) 0.0230(10) 0.0237(10) -0.0030(8) -0.0003(8) -0.0022(9)
O1 0.0185(6) 0.0208(6) 0.0288(7) -0.0061(6) -0.0020(5) -0.0026(5)
O2 0.0189(7) 0.0455(9) 0.0358(8) -0.0042(7) 0.0043(6) -0.0066(6)
N1 0.0194(8) 0.0138(6) 0.0249(8) 0.0013(6) -0.0005(6) 0.0023(6)
N2 0.0425(10) 0.0168(7) 0.0174(7) 0.0015(6) -0.0014(7) 0.0008(7)
C1 0.0160(8) 0.0112(7) 0.0224(8) 0.0005(6) -0.0002(6) -0.0006(7)
C2 0.0191(9) 0.0169(8) 0.0225(9) 0.0018(7) 0.0025(7) 0.0029(7)
C3 0.0169(9) 0.0264(9) 0.0322(10) 0.0077(8) 0.0057(8) 0.0024(8)
C4 0.0241(10) 0.0253(10) 0.0482(13) 0.0074(9) -0.0008(10) -0.0077(9)
C5 0.0323(10) 0.0142(8) 0.0379(11) 0.0037(8) -0.0043(9) -0.0063(8)
C6 0.0241(10) 0.0237(9) 0.0223(9) 0.0030(7) 0.0000(8) 0.0048(8)
C7 0.0267(10) 0.0289(10) 0.0273(10) 0.0071(8) 0.0047(8) 0.0058(8)
C8 0.0320(11) 0.0359(11) 0.0276(10) 0.0064(9) 0.0066(9) 0.0099(9)
C9 0.0401(13) 0.0329(11) 0.0417(13) -0.0024(10) 0.0066(10) 0.0009(10)
C10 0.0260(10) 0.0238(9) 0.0304(10) 0.0004(8) 0.0022(8) 0.0124(9)
C11 0.0147(8) 0.0140(8) 0.0224(8) -0.0020(6) 0.0006(6) -0.0006(7)
C12 0.0230(9) 0.0167(8) 0.0155(8) -0.0026(6) 0.0013(7) -0.0001(7)
C13 0.0259(10) 0.0219(9) 0.0200(8) -0.0013(7) -0.0022(7) 0.0035(8)
C14 0.0357(11) 0.0228(9) 0.0202(9) -0.0007(7) -0.0041(8) 0.0070(9)
C15 0.0362(10) 0.0194(8) 0.0155(8) -0.0022(7) 0.0021(8) -0.0034(8)
C16 0.0439(13) 0.0235(9) 0.0230(10) -0.0024(8) 0.0061(9) -0.0122(9)
C17 0.0341(11) 0.0349(11) 0.0264(10) -0.0058(8) 0.0085(9) -0.0184(10)
C18 0.0234(9) 0.0336(10) 0.0219(9) -0.0060(8) 0.0031(8) -0.0077(8)
C19 0.0228(9) 0.0215(9) 0.0218(9) -0.0018(7) 0.0038(7) -0.0038(8)
C20 0.0259(9) 0.0177(8) 0.0145(8) -0.0021(6) 0.0018(7) -0.0024(7)
C21 0.0209(10) 0.0467(13) 0.0294(10) 0.0000(9) 0.0029(8) 0.0041(10)
C22 0.0620(16) 0.0168(9) 0.0299(11) 0.0054(8) -0.0041(11) -0.0013(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.396(3) . ?
F2 B1 1.395(3) . ?
F3 B1 1.382(2) . ?
F4 B1 1.388(2) . ?
F5 B2 1.392(2) . ?
F6 B2 1.387(3) . ?
F7 B2 1.398(2) . ?
F8 B2 1.385(2) . ?
O1 C11 1.415(2) . ?
O1 H1 0.86(3) . ?
O2 C18 1.354(3) . ?
O2 C21 1.439(3) . ?
N1 C1 1.535(2) . ?
N1 C5 1.513(2) . ?
N1 C6 1.526(2) . ?
N1 C10 1.498(2) . ?
N2 C14 1.325(3) . ?
N2 C15 1.379(3) . ?
N2 C22 1.485(2) . ?
C1 C2 1.545(2) . ?
C1 C11 1.545(2) . ?
C1 H1A 0.96(2) . ?
C2 C3 1.523(2) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.98(2) . ?
C3 C4 1.531(3) . ?
C3 C7 1.542(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.523(3) . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.97(3) . ?
C5 H5A 0.99(2) . ?
C5 H5B 0.97(3) . ?
C6 C7 1.537(3) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.98(3) . ?
C7 C8 1.495(3) . ?
C7 H7 1.00(3) . ?
C8 C9 1.317(3) . ?
C8 H8 1.04(3) . ?
C9 H9A 0.93(3) . ?
C9 H9B 0.97(4) . ?
C10 H10A 0.97(2) . ?
C10 H10B 0.97(3) . ?
C10 H10C 1.01(3) . ?
C11 C12 1.525(2) . ?
C11 H11 0.95(2) . ?
C12 C13 1.373(3) . ?
C12 C20 1.425(3) . ?
C13 C14 1.392(3) . ?
C13 H13 0.99(2) . ?
C14 H14 0.90(3) . ?
C15 C16 1.415(3) . ?
C15 C20 1.423(3) . ?
C16 C17 1.356(3) . ?
C16 H16 0.97(3) . ?
C17 C18 1.420(3) . ?
C17 H17 0.95(3) . ?
C18 C19 1.374(3) . ?
C19 C20 1.413(3) . ?
C19 H19 0.96(2) . ?
C21 H21A 1.03(3) . ?
C21 H21B 0.97(3) . ?
C21 H21C 1.05(3) . ?
C22 H22A 0.98(3) . ?
C22 H22B 0.97(3) . ?
C22 H22C 1.01(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 B1 F1 108.68(17) . . ?
F3 B1 F1 109.88(17) . . ?
F3 B1 F2 109.77(17) . . ?
F3 B1 F4 110.80(17) . . ?
F4 B1 F1 109.42(17) . . ?
F4 B1 F2 108.25(17) . . ?
F5 B2 F7 108.29(16) . . ?
F6 B2 F5 109.01(16) . . ?
F6 B2 F7 109.56(16) . . ?
F8 B2 F5 109.07(16) . . ?
F8 B2 F6 110.54(17) . . ?
F8 B2 F7 110.31(16) . . ?
C11 O1 H1 105(2) . . ?
C18 O2 C21 116.91(16) . . ?
C5 N1 C1 112.53(14) . . ?
C5 N1 C6 108.50(15) . . ?
C6 N1 C1 106.60(13) . . ?
C10 N1 C1 111.46(14) . . ?
C10 N1 C5 109.81(15) . . ?
C10 N1 C6 107.73(15) . . ?
C14 N2 C15 121.63(16) . . ?
C14 N2 C22 118.35(19) . . ?
C15 N2 C22 119.99(19) . . ?
N1 C1 C2 107.88(13) . . ?
N1 C1 C11 113.66(14) . . ?
N1 C1 H1A 102.6(13) . . ?
C2 C1 H1A 111.0(12) . . ?
C11 C1 C2 113.49(14) . . ?
C11 C1 H1A 107.6(12) . . ?
C1 C2 H2A 107.1(14) . . ?
C1 C2 H2B 110.0(13) . . ?
C3 C2 C1 110.81(14) . . ?
C3 C2 H2A 111.9(14) . . ?
C3 C2 H2B 107.0(13) . . ?
H2A C2 H2B 110.1(19) . . ?
C2 C3 C4 109.50(17) . . ?
C2 C3 C7 109.77(15) . . ?
C2 C3 H3 110.3(14) . . ?
C4 C3 C7 107.90(16) . . ?
C4 C3 H3 110.6(14) . . ?
C7 C3 H3 108.7(13) . . ?
C3 C4 H4A 110.2(17) . . ?
C3 C4 H4B 108.1(15) . . ?
C5 C4 C3 109.36(17) . . ?
C5 C4 H4A 108.1(17) . . ?
C5 C4 H4B 109.3(16) . . ?
H4A C4 H4B 112(2) . . ?
N1 C5 C4 109.98(15) . . ?
N1 C5 H5A 104.3(14) . . ?
N1 C5 H5B 105.3(15) . . ?
C4 C5 H5A 114.9(14) . . ?
C4 C5 H5B 114.3(15) . . ?
H5A C5 H5B 107(2) . . ?
N1 C6 C7 110.65(15) . . ?
N1 C6 H6A 105.7(14) . . ?
N1 C6 H6B 106.3(14) . . ?
C7 C6 H6A 113.1(14) . . ?
C7 C6 H6B 110.1(14) . . ?
H6A C6 H6B 111(2) . . ?
C3 C7 H7 109.6(16) . . ?
C6 C7 C3 107.60(15) . . ?
C6 C7 H7 105.5(16) . . ?
C8 C7 C3 111.79(17) . . ?
C8 C7 C6 116.08(18) . . ?
C8 C7 H7 105.9(15) . . ?
C7 C8 H8 112.9(16) . . ?
C9 C8 C7 128.5(2) . . ?
C9 C8 H8 118.6(16) . . ?
C8 C9 H9A 118.9(15) . . ?
C8 C9 H9B 123(2) . . ?
H9A C9 H9B 118(3) . . ?
N1 C10 H10A 106.0(14) . . ?
N1 C10 H10B 107.9(16) . . ?
N1 C10 H10C 107.9(14) . . ?
H10A C10 H10B 110(2) . . ?
H10A C10 H10C 111.9(19) . . ?
H10B C10 H10C 113(2) . . ?
O1 C11 C1 110.03(14) . . ?
O1 C11 C12 110.98(14) . . ?
O1 C11 H11 108.9(12) . . ?
C1 C11 H11 112.1(12) . . ?
C12 C11 C1 107.11(14) . . ?
C12 C11 H11 107.7(12) . . ?
C13 C12 C11 119.35(16) . . ?
C13 C12 C20 119.13(16) . . ?
C20 C12 C11 121.49(16) . . ?
C12 C13 C14 120.24(19) . . ?
C12 C13 H13 121.0(14) . . ?
C14 C13 H13 118.8(14) . . ?
N2 C14 C13 121.32(19) . . ?
N2 C14 H14 115.7(16) . . ?
C13 C14 H14 123.0(16) . . ?
N2 C15 C16 121.08(17) . . ?
N2 C15 C20 119.13(18) . . ?
C16 C15 C20 119.79(19) . . ?
C15 C16 H16 117.7(16) . . ?
C17 C16 C15 120.03(18) . . ?
C17 C16 H16 122.3(16) . . ?
C16 C17 C18 121.03(19) . . ?
C16 C17 H17 120.0(16) . . ?
C18 C17 H17 118.9(16) . . ?
O2 C18 C17 115.19(17) . . ?
O2 C18 C19 124.95(19) . . ?
C19 C18 C17 119.84(19) . . ?
C18 C19 C20 120.61(17) . . ?
C18 C19 H19 121.0(13) . . ?
C20 C19 H19 118.3(13) . . ?
C15 C20 C12 118.43(17) . . ?
C19 C20 C12 122.92(16) . . ?
C19 C20 C15 118.64(17) . . ?
O2 C21 H21A 105.7(15) . . ?
O2 C21 H21B 110.9(17) . . ?
O2 C21 H21C 112.0(15) . . ?
H21A C21 H21B 110(2) . . ?
H21A C21 H21C 107(2) . . ?
H21B C21 H21C 111(2) . . ?
N2 C22 H22A 108.9(15) . . ?
N2 C22 H22B 109.8(15) . . ?
N2 C22 H22C 107.0(17) . . ?
H22A C22 H22B 103(2) . . ?
H22A C22 H22C 113(2) . . ?
H22B C22 H22C 115(2) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 F2 0.86(3) 1.99(3) 2.8187(18) 160(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C11 O1 -77.26(17) . . . . ?
C1 C2 C3 C4 54.7(2) . . . . ?
C1 C2 C3 C7 -63.6(2) . . . . ?
C1 C11 C12 C13 94.42(18) . . . . ?
C1 C11 C12 C20 -83.90(19) . . . . ?
C2 C1 N1 C5 -61.53(19) . . . . ?
C2 C1 N1 C6 57.30(17) . . . . ?
C2 C1 N1 C10 174.60(15) . . . . ?
C2 C1 C11 O1 46.52(19) . . . . ?
C2 C1 C11 C12 -74.20(18) . . . . ?
C2 C3 C4 C5 -65.0(2) . . . . ?
C2 C3 C7 C6 51.7(2) . . . . ?
C2 C3 C7 C8 -76.9(2) . . . . ?
C3 C2 C1 N1 6.2(2) . . . . ?
C3 C2 C1 C11 -120.63(17) . . . . ?
C3 C4 C5 N1 10.9(2) . . . . ?
C3 C7 C6 N1 12.8(2) . . . . ?
C3 C7 C8 C9 120.0(2) . . . . ?
C4 C3 C7 C6 -67.6(2) . . . . ?
C4 C3 C7 C8 163.85(17) . . . . ?
C4 C5 N1 C1 52.0(2) . . . . ?
C4 C5 N1 C6 -65.7(2) . . . . ?
C4 C5 N1 C10 176.77(17) . . . . ?
C5 C4 C3 C7 54.4(2) . . . . ?
C6 C7 C8 C9 -3.9(3) . . . . ?
C7 C6 N1 C1 -69.71(19) . . . . ?
C7 C6 N1 C5 51.7(2) . . . . ?
C7 C6 N1 C10 170.55(16) . . . . ?
C8 C7 C6 N1 138.86(17) . . . . ?
C11 C1 N1 C5 65.25(19) . . . . ?
C11 C1 N1 C6 -175.93(14) . . . . ?
C11 C1 N1 C10 -58.63(19) . . . . ?
C12 C11 C1 N1 162.02(14) . . . . ?
C13 C12 C11 O1 -25.7(2) . . . . ?
C17 C18 O2 C21 -179.21(17) . . . . ?
C19 C18 O2 C21 2.5(3) . . . . ?
C20 C12 C11 O1 155.98(15) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instruction_details
;
TITL 17srv202
CELL 1.54178 9.6961 10.2407 23.6533 90 90 90
ZERR 4 0.0003 0.0003 0.0008 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H B F N O
UNIT 88 120 8 32 8 8
L.S. 9
PLAN 5
SIZE 0.12 0.28 0.39
TEMP -153.15
HTAB O1 F2
CONF C2 C1 N1 C5
CONF C11 C1 N1 C5
CONF C2 C1 N1 C6
CONF C11 C1 N1 C6
CONF C2 C1 N1 C10
CONF C11 C1 N1 C10
CONF C3 C2 C1 N1
CONF C3 C2 C1 C11
CONF C1 C2 C3 C4
CONF C1 C2 C3 C7
CONF C2 C3 C4 C5
CONF C5 C4 C3 C7
CONF C3 C4 C5 N1
CONF C4 C5 N1 C1
CONF C4 C5 N1 C6
CONF C4 C5 N1 C10
CONF C7 C6 N1 C1
CONF C7 C6 N1 C5
CONF C7 C6 N1 C10
CONF C3 C7 C6 N1
CONF C8 C7 C6 N1
CONF C2 C3 C7 C6
CONF C4 C3 C7 C6
CONF C2 C3 C7 C8
CONF C4 C3 C7 C8
CONF C3 C7 C8 C9
CONF C6 C7 C8 C9
CONF N1 C1 C11 O1
CONF C2 C1 C11 O1
CONF C12 C11 C1 N1
CONF C2 C1 C11 C12
CONF C13 C12 C11 O1
CONF C1 C11 C12 C13
CONF C20 C12 C11 O1
CONF C1 C11 C12 C20
CONF C17 C18 O2 C21
CONF C19 C18 O2 C21
BOND $h
fmap 2
acta
OMIT -2 145
OMIT 8 7 7
WGHT 0.033 0.5
FVAR 0.29601
REM
REM
REM
F1 4 0.00225 0.67925 0.45672 11.00000 0.03601 0.03615 0.03044 =
-0.00444 -0.00296 0.01038
F2 4 0.21355 0.67705 0.49781 11.00000 0.02736 0.03086 0.03853 =
-0.00628 0.00721 -0.00556
F3 4 0.02555 0.73557 0.54922 11.00000 0.03761 0.04147 0.03409 =
-0.01514 0.00443 0.00805
F4 4 0.05660 0.52419 0.52173 11.00000 0.04377 0.02376 0.04576 =
0.00534 0.00149 -0.00935
B1 3 0.07340 0.65436 0.50688 11.00000 0.02618 0.01972 0.02501 =
-0.00210 0.00279 -0.00093
F5 4 0.59403 0.51519 0.67169 11.00000 0.03375 0.03014 0.03417 =
0.00418 -0.00515 0.00382
F6 4 0.81417 0.44283 0.67659 11.00000 0.02205 0.06790 0.03362 =
-0.01290 0.00152 -0.00524
F7 4 0.69877 0.49848 0.75681 11.00000 0.04665 0.03997 0.02210 =
-0.00667 0.00008 -0.01061
F8 4 0.63772 0.31504 0.70792 11.00000 0.04292 0.01923 0.04136 =
-0.00319 0.00263 0.00158
B2 3 0.68685 0.44156 0.70330 11.00000 0.02108 0.02303 0.02367 =
-0.00299 -0.00030 -0.00216
O1 6 0.35231 0.54639 0.40969 11.00000 0.01845 0.02080 0.02885 =
-0.00614 -0.00197 -0.00256
O2 6 -0.29723 0.36533 0.41068 11.00000 0.01891 0.04546 0.03585 =
-0.00420 0.00431 -0.00662
N1 5 0.19834 0.61718 0.29655 11.00000 0.01942 0.01377 0.02485 =
0.00134 -0.00050 0.00234
N2 5 0.18751 0.09305 0.44419 11.00000 0.04251 0.01675 0.01744 =
0.00148 -0.00136 0.00084
C1 1 0.22640 0.48527 0.32510 11.00000 0.01602 0.01119 0.02240 =
0.00047 -0.00015 -0.00058
C2 1 0.36107 0.42932 0.29997 11.00000 0.01911 0.01694 0.02255 =
0.00184 0.00253 0.00287
C3 1 0.42923 0.52798 0.26076 11.00000 0.01692 0.02640 0.03221 =
0.00771 0.00571 0.00235
C4 1 0.45115 0.65674 0.29240 11.00000 0.02410 0.02534 0.04819 =
0.00743 -0.00077 -0.00770
C5 1 0.31162 0.71561 0.30739 11.00000 0.03231 0.01417 0.03791 =
0.00368 -0.00433 -0.00631
C6 1 0.19115 0.59092 0.23312 11.00000 0.02413 0.02368 0.02233 =
0.00305 -0.00004 0.00480
C7 1 0.33434 0.55550 0.20984 11.00000 0.02671 0.02887 0.02729 =
0.00714 0.00472 0.00580
C8 1 0.33853 0.44712 0.16751 11.00000 0.03201 0.03591 0.02760 =
0.00641 0.00664 0.00989
C9 1 0.23646 0.37307 0.14960 11.00000 0.04013 0.03288 0.04175 =
-0.00237 0.00658 0.00089
C10 1 0.06226 0.67268 0.31445 11.00000 0.02596 0.02382 0.03042 =
0.00040 0.00217 0.01244
C11 1 0.22680 0.49191 0.39035 11.00000 0.01469 0.01403 0.02238 =
-0.00198 0.00059 -0.00059
C12 1 0.20890 0.35263 0.41201 11.00000 0.02301 0.01670 0.01551 =
-0.00255 0.00133 -0.00009
C13 1 0.32349 0.28026 0.42538 11.00000 0.02592 0.02185 0.02003 =
-0.00128 -0.00224 0.00348
C14 1 0.31010 0.14966 0.44081 11.00000 0.03571 0.02281 0.02023 =
-0.00072 -0.00414 0.00703
C15 1 0.06751 0.16144 0.43412 11.00000 0.03622 0.01941 0.01551 =
-0.00221 0.00209 -0.00339
C16 1 -0.06296 0.10102 0.43976 11.00000 0.04386 0.02355 0.02297 =
-0.00244 0.00613 -0.01222
C17 1 -0.17969 0.17103 0.43084 11.00000 0.03410 0.03488 0.02644 =
-0.00576 0.00847 -0.01840
C18 1 -0.17356 0.30486 0.41539 11.00000 0.02342 0.03358 0.02186 =
-0.00603 0.00310 -0.00774
C19 1 -0.04780 0.36418 0.40776 11.00000 0.02276 0.02155 0.02184 =
-0.00179 0.00379 -0.00382
C20 1 0.07591 0.29458 0.41730 11.00000 0.02593 0.01771 0.01455 =
-0.00207 0.00175 -0.00240
C21 1 -0.29556 0.50064 0.39436 11.00000 0.02087 0.04672 0.02942 =
-0.00002 0.00285 0.00413
C22 1 0.18156 -0.04854 0.45752 11.00000 0.06195 0.01683 0.02994 =
0.00538 -0.00409 -0.00129
H1 2 0.32891 0.59639 0.43738 11.00000 0.04643
H1a 2 0.14817 0.43410 0.31385 11.00000 0.01714
H2a 2 0.33677 0.34865 0.28013 11.00000 0.02629
H2b 2 0.42699 0.41059 0.33030 11.00000 0.02011
H3 2 0.51527 0.49450 0.24708 11.00000 0.02170
H4a 2 0.50259 0.64095 0.32819 11.00000 0.04555
H4b 2 0.50061 0.71621 0.26750 11.00000 0.03724
H5a 2 0.30019 0.73953 0.34764 11.00000 0.02312
H5b 2 0.28699 0.79139 0.28528 11.00000 0.03132
H6a 2 0.12309 0.52034 0.22846 11.00000 0.02995
H6b 2 0.15789 0.67222 0.21553 11.00000 0.02801
H7 2 0.36715 0.63500 0.18953 11.00000 0.03936
H8 2 0.43632 0.43257 0.15053 11.00000 0.04709
H9a 2 0.25481 0.30841 0.12280 11.00000 0.02497
H9b 2 0.14167 0.38306 0.16251 11.00000 0.06191
H10a 2 0.04973 0.75181 0.29244 11.00000 0.02517
H10b 2 0.06836 0.69415 0.35453 11.00000 0.03359
H10c 2 -0.01111 0.60574 0.30598 11.00000 0.02976
H11 2 0.15236 0.54244 0.40455 11.00000 0.01421
H13 2 0.41660 0.31922 0.42402 11.00000 0.02231
H14 2 0.38253 0.09854 0.44899 11.00000 0.02896
H16 2 -0.06498 0.00950 0.45106 11.00000 0.04111
H17 2 -0.26769 0.13003 0.43423 11.00000 0.03688
H19 2 -0.04164 0.45559 0.39860 11.00000 0.01485
H21a 2 -0.39510 0.53293 0.39908 11.00000 0.03670
H21b 2 -0.26581 0.51033 0.35549 11.00000 0.03986
H21c 2 -0.23377 0.55739 0.42144 11.00000 0.04054
H22a 2 0.12099 -0.06158 0.49039 11.00000 0.03819
H22b 2 0.13291 -0.09471 0.42764 11.00000 0.03017
H22c 2 0.27944 -0.07825 0.46431 11.00000 0.04979
HKLF 4
END
;