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N-(2-Methyl-phen-yl)maleamic acid.

ABSTRACT: In the title compound, C(11)H(11)NO(3), the conformation of the N-H bond is anti to the C=O bond in the amide segment, while it is syn to the ortho-methyl group in the phenyl ring. In the maleamic acid unit, the amide C=O bond is anti to the adjacent C-H bond, while the carboxyl C=O bond is syn to the adjacent C-H bond. The C=O and O-H bonds of the acid group are in the relatively rare anti position to each other. This is an obvious consequence of the intra-molecular O-H⋯O hydrogen bond donated to the amide carbonyl group. The ortho-substituted phenyl ring makes a dihedral angle of 12.7 (1)° with the mean plane of the maleamic acid unit. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains parallel to [001]. These chains are further linked into sheet by weak π-π inter-actions [centroid-centroid distance = 3.425 (2) Å].

SUBMITTER: Gowda BT

PROVIDER: S-EPMC3006921 | biostudies-literature |

REPOSITORIES: biostudies-literature

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

Project description:In the title compound, C(11)H(10)ClNO(3), the dihedral angle between the benzene ring and the amide group is 6.6 (10)° and an intramolecular O-H⋯O hydrogen bond occurs. In the crystal, molecules are linked by N-H⋯O hydrogen bonds, generating C(7) zigzag chains.

| S-EPMC3297936 | biostudies-literature

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

Project description:In the mol-ecular structure of the title compound, C(11)H(10)ClNO(3), the conformation of the N-H bond in the amide segment is syn to the ortho-methyl group in the phenyl ring. The C=O and O-H bonds of the acid group are in the relatively rare anti position with respect to each other. This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)-C=C-C-OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methyl-phenyl ring. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into infinite chains running along the a axis.

| S-EPMC3238967 | biostudies-literature

N-(2,6-Dimethyl-phen-yl)maleamic acid.

Project description:The asymmetric unit of the title compound, C(12)H(13)NO(3), contains two independent mol-ecules. The conformation of the N-H bond and the C=O bond in the amide segment are anti to each other. The mol-ecular conformation of each mol-ecule is stabilized by an intra-molecular O-H?O hydrogen bond. In the crystal, mol-ecules are connected through intermolecular N-H?O hydrogen bonds. In addition, there is a carbon-yl-carbonyl dipolar inter-action with an O?C contact of 2.926?(3)?Å.

| S-EPMC2971056 | biostudies-literature

N-(2,4,6-Trimethyl-phen-yl)maleamic acid.

Project description:The mol-ecular structure of the title compound, C(13)H(15)NO(3), is stabilized by a short intra-molecular O-H?O hydrogen bond within the maleamic unit. In the crystal, inter-molecular N-H?O hydrogen bonds link mol-ecules into zigzag chains propagating in [010].

| S-EPMC2971101 | biostudies-literature

N-(3,5-Dichloro-phen-yl)maleamic acid.

Project description:In the title compound, C(10)H(7)Cl(2)NO(3), the asymmetric unit contains four independent mol-ecules, which are linked to each other by N-H?O hydrogen bonds. The mol-ecular structure is stabilized by a short intra-molecular O-H?O hydrogen bond within each maleamic acid unit. In the crystal, the mol-ecules are linked into networks through N-H?O hydrogen bonds and inter-molecular C-Cl?O=C contacts [Cl?O = 3.0897?(12) and 3.0797?(13)?Å].

| S-EPMC2980102 | biostudies-literature

N-(3,4-Dimethyl-phen-yl)maleamic acid.

Project description:The title compound, C(12)H(13)NO(3), crystallizes with four independent mol-ecules in the asymmetric unit. The N-H bond and the C=O bond in the amide segment are anti to each other. The C=C double bond is cis configured and an intra-molecular O-H?O hydrogen bond is formed in each molecule. The mean planes through the aromatic ring and the amide group -NHCO- are inclined at angles of 17.4?(3), 20.8?(2), 16.2?(2) and 11.2?(3)° in the four mol-ecules. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into ribbons along the b axis.

| S-EPMC2971237 | biostudies-literature

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

Project description:The asymmetric unit of the title compound, C(10)H(7)Cl(2)NO(3), contains two independent mol-ecules. The mol-ecular conformation of each maleamic unit is stabilized by an intra-molecular O-H?O(carbon-yl) hydrogen bond owing to the anti disposition of the participating entities. The mean planes through the benzene ring and the amido group are inclined at angles of 45.7?(1) and 40.8?(1)° in the two mol-ecules. In the crystal, the independent mol-ecules self-associate via N-H?O hydrogen bonds into zigzag ribbons propagating along the a axis. The ribbons are weakly coupled by C-H?? and C-H?O inter-actions.

| S-EPMC2972031 | biostudies-literature

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.

| S-EPMC2980077 | biostudies-literature

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

Project description:In the title compound, C(10)H(8)ClNO(3), the molecular conformation is stabilized by two intra-molecular hydrogen bonds. The first is a short O-H⋯O hydrogen bond within the maleamic acid unit and the second is a C-H⋯O hydrogen bond which connects the amide group with the phenyl ring. The maleamic acid unit is essentially planar, with an r.m.s. deviation of 0.044 Å, and makes a dihedral angle of 15.2 (1)° with the phenyl ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into C(7) chains running [010].

| S-EPMC3006958 | biostudies-literature

N-(3-Nitro-phen-yl)maleamic acid.

Project description:In the title compound, C(10)H(8)N(2)O(5), the mol-ecule is slightly distorted from planarity. The mol-ecular structure is stabilized by two intra-molecular hydrogen bonds. The first is a short O-H⋯O hydrogen bond (H⋯O distance = 1.57 Å) within the maleamic acid unit and the second is a C-H⋯O hydrogen bond (H⋯O distance = 2.24 Å) which connects the amide group with the benzene ring. The nitro group is twisted by 6.2 (2)° out of the plane of the benzene ring. The crystal structure manifests a variety of hydrogen bonding. The packing is dominated by a strong inter-molecular N-H⋯O inter-action which links the mol-ecules into chains running along the b axis. The chains within a plane are further assembled by three additional types of inter-molecular C-H⋯O hydrogen bonds to form a sheet parallel to the (01) plane.

| S-EPMC3007040 | biostudies-literature

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