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

ABSTRACT: In the title compound, C(13)H(9)Cl(2)NO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-Cl atom in the aniline ring is positioned syn to the N-H bond. The two aromatic rings are almost coplanar, making a dihedral angle of 4.73?(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-EPMC3254408 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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

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

Acta crystallographica. Section E, Structure reports online 20111207 Pt 1

In the title compound, C(13)H(9)Cl(2)NO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-Cl atom in the aniline ring is positioned syn to the N-H bond. The two aromatic rings are almost coplanar, making a dihedral angle of 4.73 (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: 22259551

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

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

Project description:In the crystal structure of the title compound, C(13)H(9)Cl(2)NO, the N-H and C=O bonds are anti to each other in the two independent mol-ecules. In one mol-ecule, the N-H bond is syn to the meta-chloro group of the attached ring; it is anti in the other mol-ecule. This relationship is also observed between the C=O bond and the meta-chloro substituent of its attached ring. The amide -NHCO- group makes dihedral angles of 31.5?(4) and 34.7?(3)° with the aniline rings; it makes dihedral angles of 37.4?(3) and 37.2?(3)° with the benzoyl rings. The two rings are nearly coplanar, with dihedral angles of 9.1?(2) and 7.3?(3)° in the two independent mol-ecules. Adjacent mol-ecules are linked into infinite chains through N-H?O hydrogen bonds.

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Project description:In the mol-ecular structure of the title compound, C(13)H(9)Cl(2)NO, the amide N-C=O plane makes dihedral angles of 31.53?(8) and 36.23?(8)°, respectively, with the 4-chloro- and 2-chloro-phenyl rings. The dihedral angle between the two benzene rings is 6.25?(8)°. The mol-ecules are stacked in columns along the b axis through inter-molecular N-H?O hydrogen bonds. The columns are further connected by weak C-H?O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.

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

Project description:In the structure of the the title compound, C(13)H(9)Cl(2)NO, the N-H and C=O groups are mutually trans. Furthermore, the conformation of the C=O group is syn to the ortho-chloro group in the benzoyl ring, while the N-H bond is anti to the meta-chloro group in the aniline ring. The amide group forms dihedral angles of 89.11?(19) and 22.58?(37)°, respectively, with the benzoyl and aniline rings, while the benzoyl and aniline rings form a dihedral angle of 69.74?(14)°. The mol-ecules are linked into infinite chains through inter-molecular N-H?O hydrogen bonds.

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2-Chloro-N-(2,6-dichloro-phen-yl)benzamide.

Project description:In the structure of the title compound (N26DCP2CBA), C(13)H(8)Cl(3)NO, the conformations of N-H and C=O bonds in the amide group are trans to each other, similar to that observed in N-(2,6-dichloro-phen-yl)benzamide, 2-chloro-N-phenyl-benzamide, 2-chloro-N-(2-chloro-phen-yl)benzamide and 2-chloro-N-(2,3-dichloro-phen-yl)benzamide with similar bond parameters. Furthermore, the position of the amide O atom is syn to the ortho-chloro group in the benzoyl ring. The amide group makes a dihedral angle of 59.8?(1)° with the benzoyl ring, while the benzoyl and aniline rings make a dihedral angle of 8.1?(2)°. The mol-ecules are linked by N-H?O hydrogen bonds into infinite chains running along the b axis.

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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.

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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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3-Chloro-N-(2-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 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.

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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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