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3-Chloro-N-(2-methyl-phen-yl)benzamide.

ABSTRACT: In the mol-ecular structure of the title compound, C(14)H(12)ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N-H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48?(5)°]. The crystal structure is stabilized by N-H?O hydrogen bonds, which link the mol-ecules into chains along the b axis.

SUBMITTER: Rodrigues VZ

PROVIDER: S-EPMC3239024 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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3-Chloro-N-(2-methyl-phen-yl)benzamide.

Rodrigues Vinola Z VZ Herich Peter P Gowda B Thimme BT Kožíšek Jozef J

Acta crystallographica. Section E, Structure reports online 20111119 Pt 12

In the mol-ecular structure of the title compound, C(14)H(12)ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N-H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48 (5)°]. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which link the mol-ecules into chains along the b axis. ...[more]

PMID: 22199872

Similar Datasets

N-(3-Chloro-phen-yl)-2-methyl-benzamide.

Project description:The conformation of the N-H bond in the structure of the title compound, C(14)H(12)ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N-H and C=O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methyl-phen-yl)benzamide (N3MP2MBA). The -NHC(=O)- group makes a dihedral angle of 55.8?(7)° with the benzoyl ring, while the angle between the benzoyl and aniline rings is 37.5?(1)°; the respective values for N3MP2MBA are 55.2?(7) and 36.2?(1)°. N-H?O hydrogen bonds link the mol-ecules into infinite chains running along the c axis.

| S-EPMC2961145 | biostudies-literature

N-(4-Chloro-phen-yl)-2-methyl-benzamide.

Project description:In the structure of the title compound, C(14)H(12)ClNO, the N-H and C=O bonds are trans to each other. Furthermore, the C=O bond is syn to the ortho-methyl group in the benzoyl ring, similar to what is observed in 2-methyl-N-(4-methyl-phen-yl)benzamide and 2-methyl-N-phenyl-benzamide. The amide linkage (-NHCO-) makes dihedral angles of 36.9?(7) and 46.4?(5)° with the aniline and benzoyl rings, respectively, while the dihedral angle between the benzoyl and aniline rings is 83.1?(1)°. In the crystal structure, mol-ecules form chains running along the b axis through N-H?O hydrogen bonds.

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4-Chloro-N-(3-methyl-phen-yl)benzamide.

Project description:In the title compound, C(14)H(12)ClNO, the meta-methyl substituent in the aniline ring is positioned anti to the N-H bond. The dihedral angle between the rings is 12.4?(1)°. The crystal structure is stabilized by inter-molecular N-H?O hydrogen bonds, which link the mol-ecules into C(4) chains running along the c-axis direction.

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N-(2-Chloro-phen-yl)-4-methyl-benzamide.

Project description:The asymmetric unit of the title compound, C(14)H(12)ClNO, contains two independent mol-ecules in which the dihedral angles between the two aromatic rings are 51.76?(6) and 51.48?(7)°. The crystal structure is stabilized by inter-molecular N-H?O hydrogen bonds, which link the mol-ecules into chains running along the c axis.

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N-(4-Chloro-phen-yl)-4-methyl-benzamide.

Project description:In the title compound, C(14)H(12)ClNO, the aromatic rings make a dihedral angle of 59.25?(5)°. The methyl group is disordered over two equally occupied positions. In the crystal, N-H?O hydrogen bonds link the mol-ecules into infinite C(4) chains running along the a axis.

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2-Chloro-N-(2-methyl-phen-yl)benzamide.

Project description:In the title compound, C(14)H(12)ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08?(18)°. In the crystal, N-H?O hydrogen bonds link the mol-ecules into infinite chains running along the a axis.

| S-EPMC3379489 | biostudies-literature

N-(2-Chloro-phen-yl)-2-methyl-benzamide.

Project description:In the structure of the title compound (N2CP2MBA), C(14)H(12)ClNO, the conformations of the N-H and C=O bonds are trans to each other. Furthermore, the conformation of the N-H bond is syn to the ortho-chloro group in the aniline ring and the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, similar to what is observed in 2-chloro-N-(2-chloro-phen-yl)benzamide and 2-methyl-N-phenyl-benzamide. The amide group makes almost the same dihedral angles of 41.2?(14) and 42.2?(13)° with the aniline and benzoyl rings, respectively, while the dihedral angle between the benzoyl and aniline rings is only 7.4?(3)°. The mol-ecules in N2CP2MBA are packed into chains through N-H?O hydrogen bonds.

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N-(4-Chloro-phen-yl)-3-methyl-benzamide.

Project description:In the structure of the title compound, C(14)H(12)ClNO, the conformations of the N-H and C=O bonds are anti to each other. Furthermore, the conformation of the C=O bond is syn to the meta-methyl group in the benzoyl ring. The central -NH-C(=O)- amido group makes a dihedral angle of 32.4?(1)° with the benzoyl ring and 36.1?(1)° with the anilino ring. The dihedral angle between the two benzene rings is 68.4?(1)°. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into chains running along the a axis.

| S-EPMC2971070 | biostudies-literature

3-Chloro-N-(3-methyl-phen-yl)benzamide.

Project description:In the mol-ecular structure of the title compound, C(14)H(12)ClNO, the meta-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N-H bond. The two aromatic rings make a dihedral angle of 77.4 (1)°. In the crystal, the molecules are linked by N-H⋯O hydrogen bonds, forming C(4) chains propagating in [010].

| S-EPMC3238934 | biostudies-literature

N-(3-Chloro-phen-yl)-3-methyl-benzamide hemihydrate.

Project description:In the title compound, C(14)H(12)ClNO·0.5H(2)O, the N-H bond is in an anti conformation to the C=O bond. The two aromatic rings make a dihedral angle of 49.5?(1)°. The water mol-ecule lies on a twofold rotation axis. In the crystal, inter-molecular N-H?O and O-H?O hydrogen bonds connect the mol-ecules into a three-dimensional network.

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