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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.

Project description:The conformation of the N-H bond in the structure of the title compound (N3CPBA), C(13)H(10)ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2-chloro-phen-yl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichloro-phen-yl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3-dichloro-phen-yl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenyl-benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group -NHCO- makes a dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1)°. The mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds.

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

Project description:The structure of the title compound, C(13)H(10)ClNO, resembles those of N-phen-ylbenzamide, N-(2-chloro-phenyl)-benzamide and other benzanilides, with similar bond parameters. The amide group -NHCO- makes a dihedral angle of 29.95 (9)° with the benzoyl ring, while the benzoyl and aniline rings form a dihedral angle of 60.76 (3)°. The structure shows both intra- and inter-molecular hydrogen bonding. The mol-ecules are linked by N-H⋯O hydrogen bonds into chains running along the [100] direction.

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

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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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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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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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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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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2-Chloro-N-(2,3-dimethyl-phen-yl)benzamide.

Project description:In the title compound, C(15)H(14)ClNO, the N-H and C=O bonds in the amide group are anti to each other. The amide group is inclined at 60.3?(1)° to the chloro-substituted benzoyl ring and at 59.2?(1)° to the dimethyl-substituted aniline ring. The mean planes through the two benzene rings make a dihedral angle of 7.7?(1)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H?O hydrogen bonds, forming chains along [010].

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2-Chloro-N-(3,4-dimethyl-phen-yl)benzamide.

Project description:In the title compound, C(15)H(14)ClNO, the conformation of the N-H bond is anti to the meta-methyl group in the aniline ring, while that of the C=O bond is anti to the ortho-chloro group in the benzoyl ring. The mean planes through the two benzene rings make a dihedral angle of 80.8?(2)°. In the crystal, mol-ecules are linked by inter-molecular N-H?O hydrogen bonds, forming column-like chains along the b 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.

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