Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenyl-ethen-yl]phenol (ortho-rhom-bic polymorph) and (2E)-3-(2-bromo-phen-yl)-2-phenyl-prop-2-enoic acid

Acta Crystallogr E Crystallogr Commun. 2016 Feb 24;72(Pt 3):407-11. doi: 10.1107/S2056989016002942. eCollection 2016 Mar 1.

Abstract

The title compounds, C14H12O, (I), and C15H11BrO2, (II), were prepared and characterized as part of our studies of potential new photo-acid generators. In (I), which crystallizes in the ortho-rhom-bic space group Pca21, compared to P21/n for the previously known monoclinic polymorph [Cornella & Martin (2013 ▸). Org. Lett. 15, 6298-6301], the dihedral angle between the aromatic rings is 4.35 (6)° and the OH group is disordered over two sites in a 0.795 (3):0.205 (3) ratio. In the crystal of (I), mol-ecules are linked by O-H⋯π inter-actions involving both the major and minor -OH disorder components, generating [001] chains as part of the herringbone packing motif. The asymmetric unit of (II) contains two mol-ecules with similar conformations (weighted r.m.s. overlay fit = 0.183 Å). In the crystal of (II), both mol-ecules form carboxyl-ate inversion dimers linked by pairs of O-H⋯O hydrogen bonds, generating R 2 (2)(8) loops in each case. The dimers are linked by pairs of C-H⋯O hydrogen bonds to form [010] chains.

Keywords: O—H⋯π inter­actions; cinnamic acid; crystal structure; photo-acid generator; stilbene.