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N-(4-Chloro-3-nitro-phen-yl)maleamic acid.

ABSTRACT: In the mol-ecule of the title compound, C(10)H(7)ClN(2)O(5), the acyclic C=C double bond is cis configured. The C=O and O-H bonds of the acid group are in a relatively rare anti position to each other, due to the donation of intramolecular hydrogen bond to the amide by the carboxyl group. The nitro group is significantly twisted [dihedral angle = 66.9 (3)°] out of the plane of the remaining atoms, which are almost coplanar (r.m.s. deviation for non-H atoms except the nitro group = 0.202 Å). In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the b axis.

SUBMITTER: Chaithanya U

PROVIDER: S-EPMC3297923 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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N-(4-Chloro-3-nitro-phen-yl)maleamic acid.

Chaithanya U U Foro Sabine S Gowda B Thimme BT

Acta crystallographica. Section E, Structure reports online 20120229 Pt 3

In the mol-ecule of the title compound, C(10)H(7)ClN(2)O(5), the acyclic C=C double bond is cis configured. The C=O and O-H bonds of the acid group are in a relatively rare anti position to each other, due to the donation of intramolecular hydrogen bond to the amide by the carboxyl group. The nitro group is significantly twisted [dihedral angle = 66.9 (3)°] out of the plane of the remaining atoms, which are almost coplanar (r.m.s. deviation for non-H atoms except the nitro group = 0.202 Å). In t ...[more]

PMID: 22412726

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N-(2-Chloro-4-nitro-phen-yl)maleamic acid monohydrate.

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N-(2,4,5-Trichloro-phen-yl)maleamic acid.

Project description:The title compound, C(10)H(6)Cl(3)NO(3), crystallizes with two independent mol-ecules in the asymmetric unit. The mol-ecular structure is stabilized by a short intra-molecular O-H⋯O hydrogen bond within the maleamic unit. In the crystal, each mol-ecule self-associates via N-H⋯O hydrogen bonds into chains, each running along the b axis. Two short inter-molecular Cl⋯O contacts [3.1267 (15) and 3.0523 (12) Å] and C-H⋯O inter-actions inter-connect these chains into a three-dimensional network.

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