Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid

William T. A. Harrison; M. John Plater; Lee J. Yin

doi:10.1107/S2056989016002942

Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid

William T. A. Harrison, M. John Plater, Lee J. Yin

Chemistry

University of Malaya

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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 orthorhombic 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), molecules are linked by O-H...[pi] interactions 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 molecules with similar conformations (weighted r.m.s. overlay fit = 0.183 Å). In the crystal of (II), both molecules form carboxylate inversion dimers linked by pairs of O-H...O hydrogen bonds, generating R22(8) loops in each case. The dimers are linked by pairs of C-H...O hydrogen bonds to form [010] chains.

Original language	English
Pages (from-to)	407-411
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
Issue number	3
DOIs	https://doi.org/10.1107/S2056989016002942
Publication status	Published - 1 Mar 2016

Bibliographical note

Acknowledgements

We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections and the National Mass Spectrometry Service (University of Swansea) for the high-resolution mass-spectroscopic data.

Keywords

crystal structure
stillbene
cinnamic acid
photo-acid generator
O—H⋯π interactions

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Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid
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Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid. / Harrison, William T. A.; Plater, M. John; Yin, Lee J.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 72, No. 3, 01.03.2016, p. 407-411.

Research output: Contribution to journal › Article › peer-review

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title = "Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid",

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 orthorhombic 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), molecules are linked by O-H...[pi] interactions 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 molecules with similar conformations (weighted r.m.s. overlay fit = 0.183 {\AA}). In the crystal of (II), both molecules form carboxylate inversion dimers linked by pairs of O-H...O hydrogen bonds, generating R22(8) loops in each case. The dimers are linked by pairs of C-H...O hydrogen bonds to form [010] chains.",

keywords = "crystal structure, stillbene, cinnamic acid, photo-acid generator, O—H⋯π interactions",

author = "Harrison, {William T. A.} and Plater, {M. John} and Yin, {Lee J.}",

note = "Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections and the National Mass Spectrometry Service (University of Swansea) for the high-resolution mass-spectroscopic data.",

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AU - Harrison, William T. A.

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AU - Yin, Lee J.

N1 - Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections and the National Mass Spectrometry Service (University of Swansea) for the high-resolution mass-spectroscopic data.

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N2 - 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 orthorhombic 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), molecules are linked by O-H...[pi] interactions 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 molecules with similar conformations (weighted r.m.s. overlay fit = 0.183 Å). In the crystal of (II), both molecules form carboxylate inversion dimers linked by pairs of O-H...O hydrogen bonds, generating R22(8) loops in each case. The dimers are linked by pairs of C-H...O hydrogen bonds to form [010] chains.

AB - 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 orthorhombic 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), molecules are linked by O-H...[pi] interactions 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 molecules with similar conformations (weighted r.m.s. overlay fit = 0.183 Å). In the crystal of (II), both molecules form carboxylate inversion dimers linked by pairs of O-H...O hydrogen bonds, generating R22(8) loops in each case. The dimers are linked by pairs of C-H...O hydrogen bonds to form [010] chains.

KW - crystal structure

KW - stillbene

KW - cinnamic acid

KW - photo-acid generator

KW - O—H⋯π interactions

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Investigations of new potential photo-acid generators: crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid

Abstract

Bibliographical note

Keywords

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