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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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 languageEnglish
Pages (from-to)407-411
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
Issue number3
DOIs
Publication statusPublished - 1 Mar 2016

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Phenol
Polymorphism
phenols
Phenols
generators
Crystal structure
Dimers
acids
crystal structure
Molecules
Acids
Hydrogen bonds
dimers
hydrogen bonds
molecules
Crystals
Dihedral angle
carboxylates
crystals
Conformations

Keywords

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

Cite this

@article{53018708a3a749778bcfe4c8ddd644ac,
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.",
year = "2016",
month = "3",
day = "1",
doi = "10.1107/S2056989016002942",
language = "English",
volume = "72",
pages = "407--411",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "3",

}

TY - JOUR

T1 - Investigations of new potential photo-acid generators

T2 - crystal structures of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid

AU - Harrison, William T. A.

AU - Plater, M. John

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.

PY - 2016/3/1

Y1 - 2016/3/1

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

U2 - 10.1107/S2056989016002942

DO - 10.1107/S2056989016002942

M3 - Article

VL - 72

SP - 407

EP - 411

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 3

ER -