# Electronic Supplementary Material (ESI) for Nanoscale. # 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). # # 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_OPE3-Ph_19s088 _database_code_depnum_ccdc_archive 'CCDC 1996615' loop_ _audit_author_name _audit_author_address 'Andrei S. Batsanov' ;Durham University United Kingdom ; _audit_update_record ; 2020-04-13 deposited with the CCDC. 2020-09-01 downloaded from the CCDC. ; _audit_creation_date 2019-03-03 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C26 H18 S2' _chemical_formula_sum 'C26 H18 S2' _chemical_formula_weight 394.52 _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 0.0033 0.0016 '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' S S 0.1246 0.1234 '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 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3046(10) _cell_length_b 8.9443(8) _cell_length_c 9.1320(7) _cell_angle_alpha 90 _cell_angle_beta 98.241(7) _cell_angle_gamma 90 _cell_volume 994.65(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2573 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.7910 _cell_measurement_theta_min 3.1930 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_T_max 0.768 _exptl_absorpt_correction_T_min 0.308 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour off-white _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description pyramid _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.4856 _exptl_crystal_size_mid 0.2155 _exptl_crystal_size_min 0.0938 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_unetI/netI 0.0365 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9448 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.498 _diffrn_reflns_theta_min 2.826 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 35.00 94.00 0.5000 11.1000 omega____ theta____ kappa____ phi______ frames - 20.3282 178.0000 -30.0000 118 #__ type_ start__ end____ width___ exp.time_ 2 omega -52.00 58.00 0.5000 11.1000 omega____ theta____ kappa____ phi______ frames - 20.3282 -19.0000 90.0000 220 #__ type_ start__ end____ width___ exp.time_ 3 omega -52.00 58.00 0.5000 11.1000 omega____ theta____ kappa____ phi______ frames - 20.3282 -19.0000 0.0000 220 #__ type_ start__ end____ width___ exp.time_ 4 omega -24.00 21.00 0.5000 11.1000 omega____ theta____ kappa____ phi______ frames - -19.7032 -100.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 5 omega -89.00 9.00 0.5000 11.1000 omega____ theta____ kappa____ phi______ frames - -19.7032 -77.0000 120.0000 196 #__ type_ start__ end____ width___ exp.time_ 6 omega 35.00 81.00 0.5000 11.1000 omega____ theta____ kappa____ phi______ frames - 20.3282 178.0000 30.0000 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0275130000 _diffrn_orient_matrix_UB_12 -0.0304865000 _diffrn_orient_matrix_UB_13 0.0563699000 _diffrn_orient_matrix_UB_21 -0.0328471000 _diffrn_orient_matrix_UB_22 -0.0443891000 _diffrn_orient_matrix_UB_23 -0.0535333000 _diffrn_orient_matrix_UB_31 0.0394222000 _diffrn_orient_matrix_UB_32 -0.0581451000 _diffrn_orient_matrix_UB_33 0.0113410000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1848 _reflns_number_total 2287 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2018/3 multi-CPU version (Sheldrick, 2015a)' _computing_structure_solution 'ShelXT 2018/2 (Sheldrick, 2015)' _refine_diff_density_max 0.508 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.074 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0479 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.3972P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1246 _refine_ls_wR_factor_ref 0.1376 _refine_special_details ? _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _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 S S 0.95088(4) 0.50607(6) 0.17067(5) 0.0278(2) Uani 1 1 d . . . . . C1 C 0.83568(17) 0.4170(3) 0.0541(2) 0.0307(5) Uani 1 1 d . . . . . H1A H 0.799(2) 0.496(3) -0.006(3) 0.046(7) Uiso 1 1 d . . . . . H1B H 0.8660(19) 0.344(3) -0.012(3) 0.045(7) Uiso 1 1 d . . . . . C2 C 0.76612(18) 0.3431(2) 0.1609(2) 0.0289(5) Uani 1 1 d . . . . . H2A H 0.6874(18) 0.329(3) 0.112(2) 0.032(6) Uiso 1 1 d . . . . . H2B H 0.7971(17) 0.243(3) 0.192(2) 0.036(6) Uiso 1 1 d . . . . . C3 C 0.77624(15) 0.4402(2) 0.2972(2) 0.0221(4) Uani 1 1 d . . . . . C4 C 0.70718(16) 0.4417(2) 0.4045(2) 0.0232(4) Uani 1 1 d . . . . . H4 H 0.6379(18) 0.384(3) 0.389(2) 0.033(6) Uiso 1 1 d . . . . . C5 C 0.73210(16) 0.5317(2) 0.5315(2) 0.0219(4) Uani 1 1 d . . . . . C6 C 0.82646(16) 0.6226(2) 0.5459(2) 0.0262(4) Uani 1 1 d . . . . . H6 H 0.8433(17) 0.686(2) 0.635(2) 0.030(6) Uiso 1 1 d . . . . . C7 C 0.89563(16) 0.6224(2) 0.4378(2) 0.0267(4) Uani 1 1 d . . . . . H7 H 0.9630(19) 0.684(3) 0.453(3) 0.042(7) Uiso 1 1 d . . . . . C8 C 0.87069(16) 0.5294(2) 0.3149(2) 0.0225(4) Uani 1 1 d . . . . . C9 C 0.66389(16) 0.5281(2) 0.6477(2) 0.0238(4) Uani 1 1 d . . . . . C10 C 0.61158(17) 0.5211(2) 0.7470(2) 0.0238(4) Uani 1 1 d . . . . . C11 C 0.55339(15) 0.51149(19) 0.8740(2) 0.0210(4) Uani 1 1 d . . . . . C12 C 0.48229(16) 0.3915(2) 0.8889(2) 0.0242(4) Uani 1 1 d . . . . . H12 H 0.4696(16) 0.315(3) 0.811(2) 0.028(5) Uiso 1 1 d . . . . . C13 C 0.43003(16) 0.3800(2) 1.0134(2) 0.0239(4) Uani 1 1 d . . . . . H13 H 0.3802(17) 0.301(2) 1.026(2) 0.028(6) 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 S 0.0281(3) 0.0317(3) 0.0257(3) 0.00056(18) 0.0108(2) 0.0006(2) C1 0.0334(11) 0.0359(12) 0.0240(10) -0.0011(9) 0.0086(8) 0.0016(9) C2 0.0355(11) 0.0277(11) 0.0245(10) -0.0044(8) 0.0075(8) -0.0036(9) C3 0.0281(10) 0.0169(9) 0.0216(9) 0.0009(7) 0.0043(7) 0.0011(7) C4 0.0284(10) 0.0189(9) 0.0233(9) 0.0021(7) 0.0066(7) -0.0021(8) C5 0.0292(10) 0.0170(9) 0.0207(9) 0.0032(7) 0.0072(7) 0.0039(7) C6 0.0328(10) 0.0206(9) 0.0256(10) -0.0018(8) 0.0057(8) 0.0000(8) C7 0.0281(10) 0.0225(10) 0.0298(10) -0.0026(8) 0.0054(8) -0.0031(8) C8 0.0261(9) 0.0208(9) 0.0215(9) 0.0024(7) 0.0068(7) 0.0029(8) C9 0.0318(11) 0.0153(9) 0.0242(10) -0.0006(7) 0.0036(8) 0.0052(7) C10 0.0279(10) 0.0161(9) 0.0274(10) 0.0033(7) 0.0045(8) 0.0016(7) C11 0.0251(10) 0.0179(9) 0.0208(9) 0.0012(7) 0.0060(7) 0.0023(7) C12 0.0319(10) 0.0170(9) 0.0242(9) -0.0029(7) 0.0056(7) -0.0008(8) C13 0.0282(10) 0.0171(9) 0.0273(10) -0.0022(7) 0.0073(8) -0.0025(8) _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 S C1 1.829(2) . ? S C8 1.7675(19) . ? C1 C2 1.536(3) . ? C2 C3 1.508(3) . ? C3 C4 1.386(3) . ? C3 C8 1.400(3) . ? C4 C5 1.409(3) . ? C5 C6 1.408(3) . ? C5 C9 1.444(3) . ? C6 C7 1.393(3) . ? C7 C8 1.396(3) . ? C9 C10 1.186(3) . ? C10 C11 1.450(3) . ? C11 C12 1.403(3) . ? C11 C13 1.407(3) 3_667 ? C12 C13 1.388(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 C8 S C1 90.93(9) . . ? C2 C1 S 105.90(13) . . ? C3 C2 C1 106.77(17) . . ? C4 C3 C2 127.07(17) . . ? C4 C3 C8 119.71(17) . . ? C8 C3 C2 113.11(17) . . ? C3 C4 C5 120.31(17) . . ? C4 C5 C9 120.74(17) . . ? C6 C5 C4 119.05(17) . . ? C6 C5 C9 120.19(17) . . ? C7 C6 C5 120.87(17) . . ? C6 C7 C8 118.96(18) . . ? C3 C8 S 112.93(14) . . ? C7 C8 S 125.98(16) . . ? C7 C8 C3 121.07(18) . . ? C10 C9 C5 176.89(19) . . ? C9 C10 C11 176.8(2) . . ? C12 C11 C10 120.62(17) . . ? C12 C11 C13 118.89(18) . 3_667 ? C13 C11 C10 120.46(16) 3_667 . ? C13 C12 C11 120.33(17) . . ? C12 C13 C11 120.78(18) . 3_667 ? _shelx_res_file ; TITL 19srv088_a.res in P2(1)/c 19srv088.res created by SHELXL-2018/3 at 18:12:15 on 03-Mar-2019 REM Old TITL 19srv088 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.118, Rweak 0.075, Alpha 0.011 REM 0.439 for 144 systematic absences, Orientation as input REM Formula found by SHELXT: C13 S CELL 0.71073 12.3046 8.9443 9.132 90 98.241 90 ZERR 2 0.001 0.0008 0.0007 0 0.007 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H S UNIT 52 36 4 L.S. 7 PLAN 10 BOND list 4 fmap 2 53 acta OMIT -3 55 REM REM REM WGHT 0.072600 0.397200 FVAR 0.51927 S 3 0.950878 0.506068 0.170672 11.00000 0.02809 0.03172 = 0.02566 0.00056 0.01076 0.00058 C1 1 0.835681 0.416958 0.054106 11.00000 0.03343 0.03588 = 0.02396 -0.00108 0.00859 0.00161 H1A 2 0.798645 0.495918 -0.005509 11.00000 0.04621 H1B 2 0.865954 0.344493 -0.012394 11.00000 0.04529 C2 1 0.766120 0.343081 0.160852 11.00000 0.03548 0.02772 = 0.02447 -0.00440 0.00747 -0.00364 H2A 2 0.687423 0.329145 0.112163 11.00000 0.03165 H2B 2 0.797072 0.243190 0.191643 11.00000 0.03644 C3 1 0.776240 0.440195 0.297181 11.00000 0.02809 0.01687 = 0.02161 0.00092 0.00431 0.00106 C4 1 0.707182 0.441745 0.404515 11.00000 0.02838 0.01892 = 0.02326 0.00213 0.00656 -0.00209 H4 2 0.637901 0.384177 0.389080 11.00000 0.03310 C5 1 0.732096 0.531715 0.531537 11.00000 0.02919 0.01696 = 0.02071 0.00324 0.00717 0.00389 C6 1 0.826464 0.622574 0.545892 11.00000 0.03277 0.02058 = 0.02559 -0.00179 0.00574 0.00003 H6 2 0.843264 0.686013 0.635182 11.00000 0.02970 C7 1 0.895634 0.622445 0.437769 11.00000 0.02807 0.02245 = 0.02984 -0.00256 0.00536 -0.00312 H7 2 0.962976 0.684282 0.453209 11.00000 0.04151 C8 1 0.870685 0.529386 0.314880 11.00000 0.02614 0.02082 = 0.02147 0.00243 0.00678 0.00288 C9 1 0.663888 0.528086 0.647718 11.00000 0.03185 0.01532 = 0.02419 -0.00063 0.00361 0.00525 C10 1 0.611579 0.521114 0.746994 11.00000 0.02795 0.01609 = 0.02741 0.00332 0.00446 0.00165 C11 1 0.553388 0.511488 0.873954 11.00000 0.02513 0.01786 = 0.02082 0.00123 0.00600 0.00233 C12 1 0.482289 0.391543 0.888905 11.00000 0.03187 0.01702 = 0.02422 -0.00286 0.00556 -0.00075 H12 2 0.469555 0.314754 0.811393 11.00000 0.02823 C13 1 0.430032 0.380017 1.013429 11.00000 0.02820 0.01712 = 0.02729 -0.00219 0.00732 -0.00254 H13 2 0.380155 0.301207 1.026160 11.00000 0.02845 HKLF 4 REM 19srv088_a.res in P2(1)/c REM wR2 = 0.1376, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0479 for 1848 Fo > 4sig(Fo) and 0.0608 for all 2287 data REM 163 parameters refined using 0 restraints END WGHT 0.0735 0.3228 REM Highest difference peak 0.508, deepest hole -0.303, 1-sigma level 0.074 Q1 1 0.6068 0.4997 0.6635 11.00000 0.05 0.51 Q2 1 0.8845 0.4835 0.1032 11.00000 0.05 0.49 Q3 1 0.6374 0.5042 0.7582 11.00000 0.05 0.43 Q4 1 0.9009 0.5184 0.2449 11.00000 0.05 0.43 Q5 1 1.0246 0.5019 0.2487 11.00000 0.05 0.38 Q6 1 0.7676 0.5922 0.5107 11.00000 0.05 0.33 Q7 1 0.8057 0.5083 0.2915 11.00000 0.05 0.33 Q8 1 0.8398 0.4656 0.3295 11.00000 0.05 0.32 Q9 1 0.7073 0.5173 0.4409 11.00000 0.05 0.30 Q10 1 0.5644 0.5176 0.7783 11.00000 0.05 0.29 ; _shelx_res_checksum 42550 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 0 0 0.0469 -1.0021 -0.0108 -0.0013 0.0278 0.0335 -0.0389 1 0 0 0.0469 1.0021 0.0108 0.0013 -0.0278 -0.0335 0.0389 0 -1 0 0.2427 0.0212 -1.0022 0.0023 0.0301 0.0437 0.0591 0 1 0 0.2427 -0.0212 1.0022 -0.0023 -0.0301 -0.0437 -0.0591 -1 0 1 0.0679 -1.0051 -0.0050 1.0006 0.0842 -0.0203 -0.0280 1 0 -1 0.0679 1.0051 0.0050 -1.0006 -0.0842 0.0203 0.0280 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_submission_special_instructions 'No special instructions were received' _exptl_crystal_recrystallization_method 'slow exchange of methanol into DCM solution' _exptl_crystal_preparation 'single-molecule junction' ####################################################################### # # 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_OPE3-An_19s370 _database_code_depnum_ccdc_archive 'CCDC 1996616' loop_ _audit_author_name _audit_author_address 'Andrei S. Batsanov' ;Durham University United Kingdom ; _audit_update_record ; 2020-04-13 deposited with the CCDC. 2020-09-01 downloaded from the CCDC. ; _audit_creation_date 2019-12-15 _audit_creation_method ; Olex2 1.3-alpha (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C34 H22 S2' _chemical_formula_sum 'C34 H22 S2' _chemical_formula_weight 494.63 _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 0.0033 0.0016 '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' S S 0.1246 0.1234 '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 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7811(4) _cell_length_b 23.2361(11) _cell_length_c 11.2452(5) _cell_angle_alpha 90 _cell_angle_beta 108.171(2) _cell_angle_gamma 90 _cell_volume 2428.29(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9977 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.55 _cell_measurement_theta_min 2.19 _shelx_estimated_absorpt_T_max 0.960 _shelx_estimated_absorpt_T_min 0.875 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.1280 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.9513. The \l/2 correction factor is Not present. ; _exptl_absorpt_special_details ? _exptl_crystal_colour brown _exptl_crystal_colour_primary brown _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description rhomb _exptl_crystal_F_000 1032 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 0.00 0.0850 1.00 0.00 0.00 0.0380 -1.00 -1.00 1.00 0.1690 0.00 1.00 -1.00 0.1960 0.00 0.00 1.00 0.1320 0.00 1.00 0.00 0.1660 0.00 -2.00 -1.00 0.2010 0.00 -1.00 0.00 0.3010 _exptl_crystal_size_max 0.567 _exptl_crystal_size_mid 0.454 _exptl_crystal_size_min 0.17 _exptl_special_details ; Data were collected in shutterless mode. Full sphere of reciprocal space was nominally covered by 4 runs of 340 narrow-frame \w-scans (scan width 0.5\%, 5s exposure) and 1 run of 115 \w-scans (scan width 0.5\%, 7.5s exposure), every run at a different \f angle. Two runs of 358 \f-scans (scan width 1\%, 1.5s exposure) were used for scaling overflowing intensities. Crystal to detector distance 3.49 cm. ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_unetI/netI 0.0390 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 57742 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.034 _diffrn_reflns_theta_min 2.098 _diffrn_ambient_temperature 120 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_area_resol_mean 10.4 _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '3-circle area detector 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 MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_type 'Incoatec I\mS microsource' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 5256 _reflns_number_total 7116 _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_cell_refinement 'SAINT v8.38A (Bruker, 2017)' _computing_data_collection 'APEX3 v.2016.1-0 (Bruker, 2016)' _computing_data_reduction 'SAINT v8.38A (Bruker, 2017)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015a)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2015)' _refine_diff_density_max 0.496 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.060 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 333 _refine_ls_number_reflns 7116 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0465 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.9731P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1140 _refine_ls_wR_factor_ref 0.1245 _refine_special_details ; C(24) with corresponding H atoms is disordered between positions A and B with occupancies 0.802(7) and 0.198(7), C(34) between positions A and B with occupancies 0.908(4) and 0.092(4). ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups 2. Restrained distances C34A-C33 \\sim C34B-C33 with sigma of 0.02 S2-C34B \\sim S2-C34A with sigma of 0.02 S1-C24B \\sim S1-C24A with sigma of 0.02 C24B-C23 \\sim C24A-C23 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C24B) = Uanis(C24A) Uanis(C34B) = Uanis(C34A) 4. Others Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=1-FVAR(1) Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(H24B)=FVAR(1) Sof(H33C)=Sof(H33D)=Sof(C34B)=Sof(H34C)=Sof(H34D)=1-FVAR(2) Sof(H33A)=Sof(H33B)=Sof(C34A)=Sof(H34A)=Sof(H34B)=FVAR(2) 5.a Secondary CH2 refined with riding coordinates: C23(H23A,H23B), C23(H23C,H23D), C33(H33A,H33B), C33(H33C,H33D), C24A(H24A, H24B), C34A(H34A,H34B), C24B(H24C,H24D), C34B(H34C,H34D) 5.b Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C18(H18), C19(H19), C22(H22), C28(H28), C29(H29), C32(H32) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _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 S1 S 1.33869(5) 0.74238(2) 0.88726(5) 0.03117(12) Uani 1 1 d D . . . . S2 S 0.06809(5) 0.06791(2) 0.35110(4) 0.03058(12) Uani 1 1 d D . . . . C1 C 0.69398(15) 0.48073(6) 0.63762(13) 0.0152(3) Uani 1 1 d . . . . . C2 C 0.63009(15) 0.45877(6) 0.72504(13) 0.0153(3) Uani 1 1 d . . . . . C3 C 0.66701(17) 0.48055(6) 0.84939(14) 0.0190(3) Uani 1 1 d . . . . . H3 H 0.737390 0.510021 0.875181 0.023 Uiso 1 1 calc R U . . . C4 C 0.60263(18) 0.45963(7) 0.93192(15) 0.0232(3) Uani 1 1 d . . . . . H4 H 0.628451 0.474667 1.014524 0.028 Uiso 1 1 calc R U . . . C5 C 0.49774(18) 0.41573(7) 0.89552(15) 0.0244(3) Uani 1 1 d . . . . . H5 H 0.451995 0.402071 0.953187 0.029 Uiso 1 1 calc R U . . . C6 C 0.46190(17) 0.39291(7) 0.77816(15) 0.0205(3) Uani 1 1 d . . . . . H6 H 0.393102 0.362726 0.755653 0.025 Uiso 1 1 calc R U . . . C7 C 0.52613(15) 0.41366(6) 0.68847(14) 0.0156(3) Uani 1 1 d . . . . . C8 C 0.49036(15) 0.39043(6) 0.56635(14) 0.0165(3) Uani 1 1 d . . . . . C9 C 0.55444(16) 0.41244(6) 0.47885(14) 0.0163(3) Uani 1 1 d . . . . . C10 C 0.52099(17) 0.38972(7) 0.35544(15) 0.0219(3) Uani 1 1 d . . . . . H10 H 0.451952 0.359754 0.329888 0.026 Uiso 1 1 calc R U . . . C11 C 0.58648(19) 0.41031(7) 0.27336(15) 0.0259(4) Uani 1 1 d . . . . . H11 H 0.562856 0.394548 0.191482 0.031 Uiso 1 1 calc R U . . . C12 C 0.68929(18) 0.45495(7) 0.30937(15) 0.0247(3) Uani 1 1 d . . . . . H12 H 0.735063 0.468744 0.251831 0.030 Uiso 1 1 calc R U . . . C13 C 0.72321(17) 0.47835(7) 0.42614(14) 0.0205(3) Uani 1 1 d . . . . . H13 H 0.791563 0.508681 0.448775 0.025 Uiso 1 1 calc R U . . . C14 C 0.65734(15) 0.45785(6) 0.51484(13) 0.0158(3) Uani 1 1 d . . . . . C15 C 0.79812(16) 0.52571(6) 0.67435(14) 0.0178(3) Uani 1 1 d . . . . . C16 C 0.88771(16) 0.56258(6) 0.70720(14) 0.0186(3) Uani 1 1 d . . . . . C17 C 0.99613(16) 0.60573(6) 0.75329(14) 0.0178(3) Uani 1 1 d . . . . . C18 C 1.07222(17) 0.60813(7) 0.88093(15) 0.0211(3) Uani 1 1 d . . . . . H18 H 1.051773 0.581012 0.936303 0.025 Uiso 1 1 calc R U . . . C19 C 1.17689(17) 0.64946(7) 0.92774(15) 0.0229(3) Uani 1 1 d . . . . . H19 H 1.227548 0.651211 1.014766 0.027 Uiso 1 1 calc R U . . . C20 C 1.20674(17) 0.68838(7) 0.84540(16) 0.0218(3) Uani 1 1 d . . . . . C21 C 1.13272(17) 0.68659(6) 0.71712(15) 0.0209(3) Uani 1 1 d . . . . . C22 C 1.02744(17) 0.64537(7) 0.67131(15) 0.0203(3) Uani 1 1 d . . . . . H22 H 0.976319 0.643905 0.584350 0.024 Uiso 1 1 calc R U . . . C23 C 1.1794(2) 0.73240(8) 0.64353(18) 0.0315(4) Uani 1 1 d D . . . . H23A H 1.108763 0.764287 0.623031 0.038 Uiso 0.802(7) 1 calc R U P A 1 H23B H 1.187343 0.716259 0.564474 0.038 Uiso 0.802(7) 1 calc R U P A 1 H23C H 1.227572 0.714135 0.587739 0.038 Uiso 0.198(7) 1 calc R U P A 2 H23D H 1.093684 0.753200 0.590523 0.038 Uiso 0.198(7) 1 calc R U P A 2 C25 C 0.39445(16) 0.34266(7) 0.53282(15) 0.0201(3) Uani 1 1 d . . . . . C26 C 0.32625(16) 0.29934(7) 0.50533(15) 0.0207(3) Uani 1 1 d . . . . . C27 C 0.25763(16) 0.24432(6) 0.47340(15) 0.0188(3) Uani 1 1 d . . . . . C28 C 0.27281(17) 0.20220(7) 0.56530(15) 0.0205(3) Uani 1 1 d . . . . . H28 H 0.322183 0.211314 0.650235 0.025 Uiso 1 1 calc R U . . . C29 C 0.21703(18) 0.14728(7) 0.53474(16) 0.0232(3) Uani 1 1 d . . . . . H29 H 0.228069 0.118859 0.597764 0.028 Uiso 1 1 calc R U . . . C30 C 0.14466(17) 0.13470(6) 0.40999(15) 0.0208(3) Uani 1 1 d . . . . . C31 C 0.12586(16) 0.17643(7) 0.31725(14) 0.0201(3) Uani 1 1 d . . . . . C32 C 0.18229(17) 0.23102(7) 0.34863(15) 0.0207(3) Uani 1 1 d . . . . . H32 H 0.169899 0.259478 0.285496 0.025 Uiso 1 1 calc R U . . . C33 C 0.0399(2) 0.15558(8) 0.18917(17) 0.0317(4) Uani 1 1 d D . . . . H33A H 0.078572 0.171825 0.124842 0.038 Uiso 0.908(4) 1 calc R U P B 1 H33B H -0.062129 0.167270 0.169447 0.038 Uiso 0.908(4) 1 calc R U P B 1 H33C H -0.034670 0.184312 0.148183 0.038 Uiso 0.092(4) 1 calc R U P B 2 H33D H 0.103765 0.150495 0.136857 0.038 Uiso 0.092(4) 1 calc R U P B 2 C24A C 1.3271(3) 0.75429(14) 0.7266(2) 0.0313(7) Uani 0.802(7) 1 d D . P A 1 H24A H 1.337163 0.795827 0.711630 0.038 Uiso 0.802(7) 1 calc R U P A 1 H24B H 1.405157 0.733324 0.706459 0.038 Uiso 0.802(7) 1 calc R U P A 1 C34A C 0.0529(2) 0.09020(9) 0.19244(19) 0.0314(5) Uani 0.908(4) 1 d D . P B 1 H34A H 0.139032 0.078102 0.170482 0.038 Uiso 0.908(4) 1 calc R U P B 1 H34B H -0.033153 0.072615 0.131985 0.038 Uiso 0.908(4) 1 calc R U P B 1 C24B C 1.2772(14) 0.7730(5) 0.7254(9) 0.0313(7) Uani 0.198(7) 1 d D . P A 2 H24C H 1.227648 0.810190 0.725305 0.038 Uiso 0.198(7) 1 calc R U P A 2 H24D H 1.360910 0.779905 0.695586 0.038 Uiso 0.198(7) 1 calc R U P A 2 C34B C -0.029(2) 0.1004(7) 0.2009(15) 0.0314(5) Uani 0.092(4) 1 d D . P B 2 H34C H -0.026359 0.074378 0.131906 0.038 Uiso 0.092(4) 1 calc R U P B 2 H34D H -0.130437 0.106909 0.195613 0.038 Uiso 0.092(4) 1 calc R U P B 2 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 S1 0.0244(2) 0.0282(2) 0.0397(3) -0.00794(18) 0.00831(18) -0.01299(17) S2 0.0373(3) 0.0197(2) 0.0351(2) -0.01008(17) 0.01193(19) -0.01295(17) C1 0.0147(6) 0.0117(6) 0.0178(7) 0.0003(5) 0.0031(5) 0.0006(5) C2 0.0150(7) 0.0127(6) 0.0174(7) -0.0004(5) 0.0039(5) 0.0015(5) C3 0.0214(7) 0.0167(7) 0.0165(7) -0.0015(5) 0.0025(6) 0.0005(6) C4 0.0274(8) 0.0252(8) 0.0169(7) -0.0006(6) 0.0065(6) 0.0036(6) C5 0.0254(8) 0.0291(9) 0.0211(8) 0.0063(6) 0.0107(6) 0.0020(6) C6 0.0181(7) 0.0183(7) 0.0254(8) 0.0032(6) 0.0074(6) -0.0003(6) C7 0.0151(7) 0.0121(6) 0.0190(7) 0.0014(5) 0.0043(5) 0.0016(5) C8 0.0155(7) 0.0120(6) 0.0204(7) -0.0011(5) 0.0034(6) 0.0007(5) C9 0.0172(7) 0.0132(7) 0.0172(7) -0.0008(5) 0.0037(6) 0.0026(5) C10 0.0244(8) 0.0182(7) 0.0201(8) -0.0055(6) 0.0026(6) 0.0015(6) C11 0.0312(9) 0.0294(9) 0.0157(7) -0.0038(6) 0.0052(7) 0.0076(7) C12 0.0269(8) 0.0297(9) 0.0197(8) 0.0041(6) 0.0105(7) 0.0068(7) C13 0.0203(7) 0.0209(7) 0.0204(7) 0.0034(6) 0.0067(6) 0.0012(6) C14 0.0159(7) 0.0141(7) 0.0165(7) 0.0016(5) 0.0037(5) 0.0027(5) C15 0.0182(7) 0.0155(7) 0.0187(7) 0.0024(5) 0.0042(6) 0.0013(5) C16 0.0187(7) 0.0160(7) 0.0203(7) 0.0024(6) 0.0051(6) 0.0008(6) C17 0.0159(7) 0.0151(7) 0.0219(7) -0.0007(6) 0.0053(6) -0.0013(5) C18 0.0208(7) 0.0195(7) 0.0225(8) 0.0016(6) 0.0062(6) -0.0024(6) C19 0.0201(8) 0.0230(8) 0.0228(8) -0.0030(6) 0.0027(6) -0.0019(6) C20 0.0171(7) 0.0176(7) 0.0302(9) -0.0043(6) 0.0065(6) -0.0027(6) C21 0.0188(7) 0.0173(7) 0.0274(8) 0.0009(6) 0.0082(6) -0.0013(6) C22 0.0198(7) 0.0198(7) 0.0200(8) 0.0000(6) 0.0043(6) -0.0020(6) C23 0.0279(9) 0.0293(9) 0.0371(10) 0.0080(7) 0.0099(8) -0.0090(7) C25 0.0187(7) 0.0167(7) 0.0233(8) -0.0001(6) 0.0040(6) 0.0015(6) C26 0.0171(7) 0.0204(8) 0.0227(8) -0.0028(6) 0.0034(6) -0.0005(6) C27 0.0155(7) 0.0147(7) 0.0260(8) -0.0041(6) 0.0061(6) -0.0023(5) C28 0.0201(7) 0.0199(7) 0.0192(7) -0.0032(6) 0.0031(6) -0.0037(6) C29 0.0254(8) 0.0190(8) 0.0242(8) 0.0002(6) 0.0063(6) -0.0047(6) C30 0.0196(7) 0.0164(7) 0.0274(8) -0.0051(6) 0.0088(6) -0.0039(6) C31 0.0183(7) 0.0214(8) 0.0203(7) -0.0050(6) 0.0055(6) -0.0016(6) C32 0.0206(8) 0.0179(7) 0.0229(8) -0.0003(6) 0.0059(6) -0.0014(6) C33 0.0350(10) 0.0321(9) 0.0242(9) -0.0087(7) 0.0038(7) -0.0064(8) C24A 0.0274(15) 0.0260(14) 0.0433(12) -0.0003(10) 0.0150(11) -0.0096(11) C34A 0.0342(12) 0.0316(11) 0.0292(10) -0.0170(8) 0.0109(9) -0.0123(9) C24B 0.0274(15) 0.0260(14) 0.0433(12) -0.0003(10) 0.0150(11) -0.0096(11) C34B 0.0342(12) 0.0316(11) 0.0292(10) -0.0170(8) 0.0109(9) -0.0123(9) _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 S1 C20 1.7556(16) . ? S1 C24A 1.796(3) . ? S1 C24B 1.871(10) . ? S2 C30 1.7603(15) . ? S2 C34A 1.819(2) . ? S2 C34B 1.823(15) . ? C1 C2 1.414(2) . ? C1 C14 1.417(2) . ? C1 C15 1.428(2) . ? C2 C3 1.424(2) . ? C2 C7 1.429(2) . ? C3 H3 0.9500 . ? C3 C4 1.363(2) . ? C4 H4 0.9500 . ? C4 C5 1.414(2) . ? C5 H5 0.9500 . ? C5 C6 1.363(2) . ? C6 H6 0.9500 . ? C6 C7 1.428(2) . ? C7 C8 1.414(2) . ? C8 C9 1.417(2) . ? C8 C25 1.426(2) . ? C9 C10 1.424(2) . ? C9 C14 1.427(2) . ? C10 H10 0.9500 . ? C10 C11 1.364(2) . ? C11 H11 0.9500 . ? C11 C12 1.413(2) . ? C12 H12 0.9500 . ? C12 C13 1.363(2) . ? C13 H13 0.9500 . ? C13 C14 1.427(2) . ? C15 C16 1.198(2) . ? C16 C17 1.434(2) . ? C17 C18 1.397(2) . ? C17 C22 1.403(2) . ? C18 H18 0.9500 . ? C18 C19 1.383(2) . ? C19 H19 0.9500 . ? C19 C20 1.389(2) . ? C20 C21 1.398(2) . ? C21 C22 1.383(2) . ? C21 C23 1.504(2) . ? C22 H22 0.9500 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 H23C 0.9900 . ? C23 H23D 0.9900 . ? C23 C24A 1.541(3) . ? C23 C24B 1.450(10) . ? C25 C26 1.194(2) . ? C26 C27 1.437(2) . ? C27 C28 1.397(2) . ? C27 C32 1.401(2) . ? C28 H28 0.9500 . ? C28 C29 1.388(2) . ? C29 H29 0.9500 . ? C29 C30 1.391(2) . ? C30 C31 1.394(2) . ? C31 C32 1.384(2) . ? C31 C33 1.504(2) . ? C32 H32 0.9500 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C33 H33C 0.9900 . ? C33 H33D 0.9900 . ? C33 C34A 1.524(3) . ? C33 C34B 1.471(14) . ? C24A H24A 0.9900 . ? C24A H24B 0.9900 . ? C34A H34A 0.9900 . ? C34A H34B 0.9900 . ? C24B H24C 0.9900 . ? C24B H24D 0.9900 . ? C34B H34C 0.9900 . ? C34B H34D 0.9900 . ? 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 C20 S1 C24A 91.71(9) . . ? C20 S1 C24B 91.4(3) . . ? C30 S2 C34A 90.75(8) . . ? C30 S2 C34B 91.1(5) . . ? C2 C1 C14 120.64(13) . . ? C2 C1 C15 119.54(13) . . ? C14 C1 C15 119.82(13) . . ? C1 C2 C3 121.52(13) . . ? C1 C2 C7 119.58(13) . . ? C3 C2 C7 118.90(13) . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.82(14) . . ? C4 C3 H3 119.6 . . ? C3 C4 H4 119.7 . . ? C3 C4 C5 120.51(15) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 119.8 . . ? C6 C5 C4 120.36(15) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 119.5 . . ? C5 C6 C7 121.03(15) . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 118.35(13) . . ? C8 C7 C2 119.85(13) . . ? C8 C7 C6 121.80(14) . . ? C7 C8 C9 120.51(13) . . ? C7 C8 C25 119.79(13) . . ? C9 C8 C25 119.63(13) . . ? C8 C9 C10 121.74(14) . . ? C8 C9 C14 119.71(13) . . ? C10 C9 C14 118.54(13) . . ? C9 C10 H10 119.5 . . ? C11 C10 C9 121.05(15) . . ? C11 C10 H10 119.5 . . ? C10 C11 H11 119.8 . . ? C10 C11 C12 120.39(15) . . ? C12 C11 H11 119.8 . . ? C11 C12 H12 119.8 . . ? C13 C12 C11 120.43(15) . . ? C13 C12 H12 119.8 . . ? C12 C13 H13 119.6 . . ? C12 C13 C14 120.85(15) . . ? C14 C13 H13 119.6 . . ? C1 C14 C9 119.69(13) . . ? C1 C14 C13 121.57(14) . . ? C9 C14 C13 118.72(13) . . ? C16 C15 C1 178.41(17) . . ? C15 C16 C17 176.94(16) . . ? C18 C17 C16 119.76(14) . . ? C18 C17 C22 119.57(14) . . ? C22 C17 C16 120.67(14) . . ? C17 C18 H18 119.6 . . ? C19 C18 C17 120.86(14) . . ? C19 C18 H18 119.6 . . ? C18 C19 H19 120.6 . . ? C18 C19 C20 118.89(15) . . ? C20 C19 H19 120.6 . . ? C19 C20 S1 125.19(13) . . ? C19 C20 C21 121.29(14) . . ? C21 C20 S1 113.50(12) . . ? C20 C21 C23 113.46(14) . . ? C22 C21 C20 119.40(14) . . ? C22 C21 C23 127.14(15) . . ? C17 C22 H22 120.0 . . ? C21 C22 C17 119.98(15) . . ? C21 C22 H22 120.0 . . ? C21 C23 H23A 110.4 . . ? C21 C23 H23B 110.4 . . ? C21 C23 H23C 109.4 . . ? C21 C23 H23D 109.4 . . ? C21 C23 C24A 106.73(16) . . ? H23A C23 H23B 108.6 . . ? H23C C23 H23D 108.0 . . ? C24A C23 H23A 110.4 . . ? C24A C23 H23B 110.4 . . ? C24B C23 C21 111.4(4) . . ? C24B C23 H23C 109.4 . . ? C24B C23 H23D 109.4 . . ? C26 C25 C8 173.30(16) . . ? C25 C26 C27 174.22(16) . . ? C28 C27 C26 120.32(14) . . ? C28 C27 C32 119.18(14) . . ? C32 C27 C26 120.38(14) . . ? C27 C28 H28 119.4 . . ? C29 C28 C27 121.18(14) . . ? C29 C28 H28 119.4 . . ? C28 C29 H29 120.7 . . ? C28 C29 C30 118.69(15) . . ? C30 C29 H29 120.7 . . ? C29 C30 S2 125.99(12) . . ? C29 C30 C31 121.01(14) . . ? C31 C30 S2 112.99(12) . . ? C30 C31 C33 113.35(14) . . ? C32 C31 C30 119.84(14) . . ? C32 C31 C33 126.80(15) . . ? C27 C32 H32 120.0 . . ? C31 C32 C27 120.07(15) . . ? C31 C32 H32 120.0 . . ? C31 C33 H33A 110.5 . . ? C31 C33 H33B 110.5 . . ? C31 C33 H33C 109.8 . . ? C31 C33 H33D 109.8 . . ? C31 C33 C34A 106.30(15) . . ? H33A C33 H33B 108.7 . . ? H33C C33 H33D 108.3 . . ? C34A C33 H33A 110.5 . . ? C34A C33 H33B 110.5 . . ? C34B C33 C31 109.2(6) . . ? C34B C33 H33C 109.8 . . ? C34B C33 H33D 109.8 . . ? S1 C24A H24A 110.1 . . ? S1 C24A H24B 110.1 . . ? C23 C24A S1 108.20(15) . . ? C23 C24A H24A 110.1 . . ? C23 C24A H24B 110.1 . . ? H24A C24A H24B 108.4 . . ? S2 C34A H34A 110.4 . . ? S2 C34A H34B 110.4 . . ? C33 C34A S2 106.75(13) . . ? C33 C34A H34A 110.4 . . ? C33 C34A H34B 110.4 . . ? H34A C34A H34B 108.6 . . ? S1 C24B H24C 110.0 . . ? S1 C24B H24D 110.0 . . ? C23 C24B S1 108.6(6) . . ? C23 C24B H24C 110.0 . . ? C23 C24B H24D 110.0 . . ? H24C C24B H24D 108.4 . . ? S2 C34B H34C 109.9 . . ? S2 C34B H34D 109.9 . . ? C33 C34B S2 109.0(9) . . ? C33 C34B H34C 109.9 . . ? C33 C34B H34D 109.9 . . ? H34C C34B H34D 108.3 . . ? 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 S1 C20 C21 C22 178.93(12) . . . . ? S1 C20 C21 C23 -1.66(18) . . . . ? S2 C30 C31 C32 -178.91(12) . . . . ? S2 C30 C31 C33 2.18(18) . . . . ? C1 C2 C3 C4 178.85(14) . . . . ? C1 C2 C7 C6 -179.12(13) . . . . ? C1 C2 C7 C8 1.4(2) . . . . ? C2 C1 C14 C9 0.3(2) . . . . ? C2 C1 C14 C13 -178.37(13) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 C7 C8 C9 -1.4(2) . . . . ? C2 C7 C8 C25 175.49(13) . . . . ? C3 C2 C7 C6 1.0(2) . . . . ? C3 C2 C7 C8 -178.49(13) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C4 C5 C6 C7 -1.7(2) . . . . ? C5 C6 C7 C2 0.5(2) . . . . ? C5 C6 C7 C8 179.91(15) . . . . ? C6 C7 C8 C9 179.14(13) . . . . ? C6 C7 C8 C25 -3.9(2) . . . . ? C7 C2 C3 C4 -1.2(2) . . . . ? C7 C8 C9 C10 179.70(14) . . . . ? C7 C8 C9 C14 0.9(2) . . . . ? C8 C9 C10 C11 -178.20(15) . . . . ? C8 C9 C14 C1 -0.3(2) . . . . ? C8 C9 C14 C13 178.42(13) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C10 C9 C14 C1 -179.18(13) . . . . ? C10 C9 C14 C13 -0.4(2) . . . . ? C10 C11 C12 C13 -0.6(2) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C13 C14 C1 178.42(14) . . . . ? C12 C13 C14 C9 -0.3(2) . . . . ? C14 C1 C2 C3 179.04(13) . . . . ? C14 C1 C2 C7 -0.9(2) . . . . ? C14 C9 C10 C11 0.6(2) . . . . ? C15 C1 C2 C3 0.1(2) . . . . ? C15 C1 C2 C7 -179.85(13) . . . . ? C15 C1 C14 C9 179.28(13) . . . . ? C15 C1 C14 C13 0.6(2) . . . . ? C16 C17 C18 C19 -179.76(15) . . . . ? C16 C17 C22 C21 -179.73(14) . . . . ? C17 C18 C19 C20 -0.8(2) . . . . ? C18 C17 C22 C21 -0.2(2) . . . . ? C18 C19 C20 S1 -178.28(12) . . . . ? C18 C19 C20 C21 0.3(2) . . . . ? C19 C20 C21 C22 0.2(2) . . . . ? C19 C20 C21 C23 179.60(16) . . . . ? C20 S1 C24A C23 22.2(2) . . . . ? C20 S1 C24B C23 -12.0(8) . . . . ? C20 C21 C22 C17 -0.2(2) . . . . ? C20 C21 C23 C24A 18.0(2) . . . . ? C20 C21 C23 C24B -7.9(7) . . . . ? C21 C23 C24A S1 -26.0(3) . . . . ? C21 C23 C24B S1 13.0(10) . . . . ? C22 C17 C18 C19 0.7(2) . . . . ? C22 C21 C23 C24A -162.7(2) . . . . ? C22 C21 C23 C24B 171.4(7) . . . . ? C23 C21 C22 C17 -179.56(16) . . . . ? C25 C8 C9 C10 2.8(2) . . . . ? C25 C8 C9 C14 -176.06(13) . . . . ? C26 C27 C28 C29 -174.82(15) . . . . ? C26 C27 C32 C31 175.05(14) . . . . ? C27 C28 C29 C30 -0.2(2) . . . . ? C28 C27 C32 C31 -1.0(2) . . . . ? C28 C29 C30 S2 179.16(12) . . . . ? C28 C29 C30 C31 -1.1(2) . . . . ? C29 C30 C31 C32 1.3(2) . . . . ? C29 C30 C31 C33 -177.58(15) . . . . ? C30 S2 C34A C33 -27.28(15) . . . . ? C30 S2 C34B C33 19.2(13) . . . . ? C30 C31 C32 C27 -0.2(2) . . . . ? C30 C31 C33 C34A -22.6(2) . . . . ? C30 C31 C33 C34B 12.5(10) . . . . ? C31 C33 C34A S2 32.06(18) . . . . ? C31 C33 C34B S2 -20.9(14) . . . . ? C32 C27 C28 C29 1.2(2) . . . . ? C32 C31 C33 C34A 158.56(17) . . . . ? C32 C31 C33 C34B -166.3(10) . . . . ? C33 C31 C32 C27 178.51(15) . . . . ? C24A S1 C20 C19 166.21(19) . . . . ? C24A S1 C20 C21 -12.48(17) . . . . ? C34A S2 C30 C29 -165.14(16) . . . . ? C34A S2 C30 C31 15.11(14) . . . . ? C24B S1 C20 C19 -173.5(5) . . . . ? C24B S1 C20 C21 7.8(5) . . . . ? C34B S2 C30 C29 167.4(8) . . . . ? C34B S2 C30 C31 -12.4(8) . . . . ? _shelx_res_file ; TITL 19srv370_a.res in P2(1)/c 19srv370.res created by SHELXL-2018/3 at 23:30:52 on 15-Dec-2019 REM Old TITL 19srv370 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.137, Rweak 0.009, Alpha 0.019 REM 0.438 for 143 systematic absences, Orientation as input REM Formula found by SHELXT: C34 S2 CELL 0.71073 9.7811 23.2361 11.2452 90 108.171 90 ZERR 4 0.0004 0.0011 0.0005 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H S UNIT 136 88 8 SADI C34A C33 C34B C33 SADI S2 C34B S2 C34A SADI S1 C24B S1 C24A SADI C24B C23 C24A C23 EADP C24B C24A EADP C34B C34A L.S. 7 PLAN 5 SIZE 0.17 0.454 0.567 TEMP -153.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.064000 0.973100 FVAR 0.47371 0.80166 0.90790 S1 3 1.338688 0.742376 0.887259 11.00000 0.02444 0.02825 = 0.03967 -0.00794 0.00831 -0.01299 S2 3 0.068088 0.067905 0.351103 11.00000 0.03732 0.01970 = 0.03515 -0.01008 0.01193 -0.01295 C1 1 0.693979 0.480726 0.637616 11.00000 0.01473 0.01173 = 0.01780 0.00025 0.00314 0.00060 C2 1 0.630087 0.458772 0.725037 11.00000 0.01504 0.01265 = 0.01737 -0.00041 0.00393 0.00148 C3 1 0.667010 0.480547 0.849390 11.00000 0.02144 0.01674 = 0.01647 -0.00152 0.00247 0.00055 AFIX 43 H3 2 0.737390 0.510021 0.875181 11.00000 -1.20000 AFIX 0 C4 1 0.602629 0.459629 0.931915 11.00000 0.02741 0.02515 = 0.01686 -0.00055 0.00651 0.00361 AFIX 43 H4 2 0.628451 0.474667 1.014524 11.00000 -1.20000 AFIX 0 C5 1 0.497743 0.415735 0.895521 11.00000 0.02539 0.02910 = 0.02108 0.00635 0.01072 0.00195 AFIX 43 H5 2 0.451995 0.402071 0.953187 11.00000 -1.20000 AFIX 0 C6 1 0.461895 0.392910 0.778155 11.00000 0.01808 0.01827 = 0.02541 0.00318 0.00736 -0.00035 AFIX 43 H6 2 0.393102 0.362726 0.755653 11.00000 -1.20000 AFIX 0 C7 1 0.526127 0.413658 0.688472 11.00000 0.01513 0.01214 = 0.01898 0.00139 0.00430 0.00156 C8 1 0.490364 0.390433 0.566348 11.00000 0.01554 0.01203 = 0.02043 -0.00105 0.00337 0.00075 C9 1 0.554438 0.412441 0.478845 11.00000 0.01725 0.01319 = 0.01717 -0.00081 0.00369 0.00259 C10 1 0.520989 0.389725 0.355438 11.00000 0.02442 0.01819 = 0.02009 -0.00552 0.00258 0.00151 AFIX 43 H10 2 0.451952 0.359754 0.329888 11.00000 -1.20000 AFIX 0 C11 1 0.586485 0.410311 0.273356 11.00000 0.03119 0.02937 = 0.01570 -0.00379 0.00517 0.00764 AFIX 43 H11 2 0.562856 0.394548 0.191482 11.00000 -1.20000 AFIX 0 C12 1 0.689293 0.454951 0.309372 11.00000 0.02693 0.02968 = 0.01975 0.00408 0.01048 0.00677 AFIX 43 H12 2 0.735063 0.468744 0.251831 11.00000 -1.20000 AFIX 0 C13 1 0.723208 0.478346 0.426138 11.00000 0.02032 0.02090 = 0.02044 0.00342 0.00666 0.00118 AFIX 43 H13 2 0.791563 0.508681 0.448775 11.00000 -1.20000 AFIX 0 C14 1 0.657344 0.457855 0.514842 11.00000 0.01586 0.01409 = 0.01646 0.00159 0.00372 0.00275 C15 1 0.798120 0.525712 0.674353 11.00000 0.01825 0.01555 = 0.01868 0.00237 0.00424 0.00133 C16 1 0.887708 0.562575 0.707203 11.00000 0.01873 0.01599 = 0.02030 0.00245 0.00513 0.00078 C17 1 0.996135 0.605732 0.753290 11.00000 0.01592 0.01514 = 0.02191 -0.00074 0.00530 -0.00129 C18 1 1.072216 0.608133 0.880930 11.00000 0.02083 0.01948 = 0.02247 0.00164 0.00618 -0.00242 AFIX 43 H18 2 1.051773 0.581012 0.936303 11.00000 -1.20000 AFIX 0 C19 1 1.176888 0.649462 0.927737 11.00000 0.02015 0.02302 = 0.02276 -0.00304 0.00269 -0.00193 AFIX 43 H19 2 1.227548 0.651211 1.014766 11.00000 -1.20000 AFIX 0 C20 1 1.206740 0.688383 0.845399 11.00000 0.01711 0.01757 = 0.03024 -0.00425 0.00648 -0.00267 C21 1 1.132718 0.686587 0.717122 11.00000 0.01883 0.01733 = 0.02738 0.00090 0.00822 -0.00129 C22 1 1.027439 0.645375 0.671312 11.00000 0.01976 0.01975 = 0.01996 -0.00003 0.00433 -0.00198 AFIX 43 H22 2 0.976319 0.643905 0.584350 11.00000 -1.20000 AFIX 0 C23 1 1.179403 0.732402 0.643530 11.00000 0.02791 0.02931 = 0.03705 0.00801 0.00994 -0.00904 PART 1 AFIX 23 H23A 2 1.108763 0.764287 0.623031 21.00000 -1.20000 H23B 2 1.187343 0.716259 0.564474 21.00000 -1.20000 AFIX 23 PART 0 PART 2 H23C 2 1.227572 0.714135 0.587739 -21.00000 -1.20000 H23D 2 1.093684 0.753200 0.590523 -21.00000 -1.20000 AFIX 0 PART 0 C25 1 0.394453 0.342658 0.532822 11.00000 0.01871 0.01665 = 0.02327 -0.00010 0.00399 0.00145 C26 1 0.326247 0.299342 0.505335 11.00000 0.01706 0.02044 = 0.02273 -0.00280 0.00339 -0.00050 C27 1 0.257635 0.244321 0.473396 11.00000 0.01553 0.01467 = 0.02602 -0.00413 0.00609 -0.00228 C28 1 0.272811 0.202204 0.565304 11.00000 0.02015 0.01994 = 0.01917 -0.00320 0.00305 -0.00368 AFIX 43 H28 2 0.322183 0.211314 0.650235 11.00000 -1.20000 AFIX 0 C29 1 0.217032 0.147283 0.534736 11.00000 0.02544 0.01899 = 0.02419 0.00019 0.00627 -0.00469 AFIX 43 H29 2 0.228069 0.118859 0.597764 11.00000 -1.20000 AFIX 0 C30 1 0.144662 0.134697 0.409988 11.00000 0.01959 0.01640 = 0.02738 -0.00506 0.00879 -0.00394 C31 1 0.125857 0.176433 0.317246 11.00000 0.01830 0.02138 = 0.02026 -0.00501 0.00553 -0.00159 C32 1 0.182286 0.231015 0.348632 11.00000 0.02062 0.01792 = 0.02292 -0.00032 0.00587 -0.00142 AFIX 43 H32 2 0.169899 0.259478 0.285496 11.00000 -1.20000 AFIX 0 C33 1 0.039856 0.155575 0.189170 11.00000 0.03499 0.03206 = 0.02418 -0.00866 0.00385 -0.00640 PART 1 AFIX 23 H33A 2 0.078572 0.171825 0.124842 31.00000 -1.20000 H33B 2 -0.062129 0.167270 0.169447 31.00000 -1.20000 AFIX 23 PART 0 PART 2 H33C 2 -0.034670 0.184312 0.148183 -31.00000 -1.20000 H33D 2 0.103765 0.150495 0.136857 -31.00000 -1.20000 AFIX 0 PART 0 PART 1 C24A 1 1.327056 0.754289 0.726603 21.00000 0.02745 0.02600 = 0.04332 -0.00033 0.01500 -0.00959 AFIX 23 H24A 2 1.337163 0.795827 0.711630 21.00000 -1.20000 H24B 2 1.405157 0.733324 0.706459 21.00000 -1.20000 AFIX 0 C34A 1 0.052861 0.090197 0.192435 31.00000 0.03420 0.03158 = 0.02916 -0.01704 0.01094 -0.01226 AFIX 23 H34A 2 0.139032 0.078102 0.170482 31.00000 -1.20000 H34B 2 -0.033153 0.072615 0.131985 31.00000 -1.20000 AFIX 0 PART 0 PART 2 C24B 1 1.277155 0.773022 0.725378 -21.00000 0.02745 0.02600 = 0.04332 -0.00033 0.01500 -0.00959 AFIX 23 H24C 2 1.227648 0.810190 0.725305 -21.00000 -1.20000 H24D 2 1.360910 0.779905 0.695586 -21.00000 -1.20000 AFIX 0 C34B 1 -0.028667 0.100444 0.200894 -31.00000 0.03420 0.03158 = 0.02916 -0.01704 0.01094 -0.01226 AFIX 23 H34C 2 -0.026359 0.074378 0.131906 -31.00000 -1.20000 H34D 2 -0.130437 0.106909 0.195613 -31.00000 -1.20000 AFIX 0 HKLF 4 REM 19srv370_a.res in P2(1)/c REM wR2 = 0.1245, GooF = S = 1.029, Restrained GooF = 1.032 for all data REM R1 = 0.0465 for 5256 Fo > 4sig(Fo) and 0.0720 for all 7116 data REM 333 parameters refined using 4 restraints END WGHT 0.0637 0.9861 REM Highest difference peak 0.496, deepest hole -0.449, 1-sigma level 0.060 Q1 1 1.3459 0.7457 0.8143 11.00000 0.05 0.50 Q2 1 1.3131 0.7538 0.8092 11.00000 0.05 0.49 Q3 1 0.3300 0.3223 0.4729 11.00000 0.05 0.40 Q4 1 0.5323 0.3999 0.5274 11.00000 0.05 0.40 Q5 1 -0.0191 0.0824 0.3365 11.00000 0.05 0.39 ; _shelx_res_checksum 70443 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_submission_special_instructions 'No special instructions were received' #===END _exptl_crystal_recrystallization_method 'slow exchange of hexane into DCM solution' _exptl_crystal_preparation 'single-molecule junction'