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A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid

Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydro­thermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)meth­yl]isophthalic acid with manganese chloride tetra­hydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this...

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Autor principal: Kuai, Hai-Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515175/
https://www.ncbi.nlm.nih.gov/pubmed/23284402
http://dx.doi.org/10.1107/S1600536812041025
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author Kuai, Hai-Wei
author_facet Kuai, Hai-Wei
author_sort Kuai, Hai-Wei
collection PubMed
description Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydro­thermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)meth­yl]isophthalic acid with manganese chloride tetra­hydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011 ▶). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers. O—H⋯N contacts connect these dimers into zigzag chains along [010].
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spelling pubmed-35151752013-01-02 A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid Kuai, Hai-Wei Acta Crystallogr Sect E Struct Rep Online Organic Papers Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydro­thermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)meth­yl]isophthalic acid with manganese chloride tetra­hydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011 ▶). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers. O—H⋯N contacts connect these dimers into zigzag chains along [010]. International Union of Crystallography 2012-10-06 /pmc/articles/PMC3515175/ /pubmed/23284402 http://dx.doi.org/10.1107/S1600536812041025 Text en © Hai-Wei Kuai 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Kuai, Hai-Wei
A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
title A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
title_full A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
title_fullStr A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
title_full_unstemmed A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
title_short A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
title_sort monoclinic polymorph of 5-[(1h-benzimidazol-1-yl)meth­yl]benzene-1,3-dicarb­oxy­lic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515175/
https://www.ncbi.nlm.nih.gov/pubmed/23284402
http://dx.doi.org/10.1107/S1600536812041025
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