(E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism

Mason, Helen E.; Howard, Judith A.K.; Sparkes, Hazel A.

Abstract

A new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, C13H10Br-NO, is reported, together with a low-temperature structure determination of thepreviously published polymorph. Both polymorphs were found to have anintramolecular O—HN hydrogen bond between the phenol OH group andthe imine N atom, forming an S (6) ring. The crystals were observed to havedifferent colours at room temperature, with the previously published polymorphbeing more orange and the new polymorph more yellow. The planarity of themolecule in the two polymorphs was found to be significantly different, withdihedral angles () between the two aromatic rings for the previously published‘orange’ polymorph of  = 1.8 (2)at 120 K, while the new ‘yellow’ polymorphhad  = 45.6 (1)at 150 K. It was also observed that both polymorphs displayedsome degree of thermochromism and upon cooling the ‘orange’ polymorphbecame more yellow, while the ‘yellow’ polymorph became paler upon cooling.

Citation

Mason, H. E., Howard, J. A., & Sparkes, H. A. (2020). (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism. Acta Crystallographica Section C: Structural Chemistry, 76(11), Article C76. https://doi.org/10.1107/s2053229620011560

• Journal Article Type: Article
• Acceptance Date: Aug 24, 2020
• Online Publication Date: Oct 8, 2020
• Publication Date: 2020
• Deposit Date: Oct 12, 2020
• Publicly Available Date: Oct 13, 2020
• Journal: Acta Crystallographica Section C: Structural Chemistry
• Electronic ISSN: 2053-2296
• Publisher: International Union of Crystallography
• Peer Reviewed: Peer Reviewed
• Volume: 76
• Issue: 11
• Article Number: C76
• DOI: https://doi.org/10.1107/s2053229620011560
• Public URL: https://durham-repository.worktribe.com/output/1254236