(<i>E</i>)-4-Iodo-2-[(phenylimino)methyl]phenol

Swetha, G.; Malarselvi, R. Ida; Raja, C. Ramachandra; Thiruvalluvar, A.; Priscilla, J.

doi:10.1107/s2414314619007880

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“…The structures of (E)-4-halogeno-2-[(phenylimino)methyl]phenol have been reported for fluoro (Swetha et al, 2017), chloro (Bregman et al, 1964;Ogawa et al, 1998), bromo (Yan et al, 2014) and iodo (Swetha et al, 2019). Herein a new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, denoted 1B, is reported together with a new low-temperature determination of the previously reported polymorph, 1A (Yan et al, 2014).…”

Section: Introductionmentioning

confidence: 73%

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

2020

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A new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, C13H10BrNO, is reported, together with a low-temperature structure determination of the previously published polymorph. Both polymorphs were found to have an intramolecular O—H...N hydrogen bond between the phenol OH group and the imine N atom, forming an S(6) ring. The crystals were observed to have different colours at room temperature, with the previously published polymorph being more orange and the new polymorph more yellow. The planarity of the molecule in the two polymorphs was found to be significantly different, with dihedral angles (Φ) between the two aromatic rings for the previously published `orange' polymorph of Φ = 1.8 (2)° at 120 K, while the new `yellow' polymorph had Φ = 45.6 (1)° at 150 K. It was also observed that both polymorphs displayed some degree of thermochromism and upon cooling the `orange' polymorph became more yellow, while the `yellow' polymorph became paler upon cooling.

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