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

ABSTRACT: The N-H bond in the title compound, C(8)H(7)Cl(2)NO, is anti to the meta-chloro substituent in the aromatic ring in both independent mol-ecules comprising the asymmetric unit. The C=O bond is anti to the N-H bond and is also anti to the methyl-ene H atoms. Inter-molecular N-H?O hydrogen bonds link the mol-ecules into supra-molecular chains.

SUBMITTER: Gowda BT

PROVIDER: S-EPMC2977650 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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

Gowda B Thimme BT Foro Sabine S Terao Hiromitsu H Fuess Hartmut H

Acta crystallographica. Section E, Structure reports online 20090402 Pt 5

The N-H bond in the title compound, C(8)H(7)Cl(2)NO, is anti to the meta-chloro substituent in the aromatic ring in both independent mol-ecules comprising the asymmetric unit. The C=O bond is anti to the N-H bond and is also anti to the methyl-ene H atoms. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains. ...[more]

PMID: 21583993

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

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N-(4-Bromo-phen-yl)-2-(4-chloro-phen-yl)acetamide.

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2-(4-Chloro-phen-yl)-N-(3,4-di-fluoro-phen-yl)acetamide.

Project description:In the title compound, C14H10ClF2NO, the dihedral angle between the mean planes of the 4-chloro-phenyl and 3,4-di-fluoro-phenyl rings is 65.2 (1)°. These two planes are twisted by 83.5 (5) and 38.9 (9)°, respectively, from that of the acetamide group. In the crystal, N-H⋯O hydrogen bonds form infinite chains along [100]. Weak C-H⋯O and C-H⋯F inter-actions are also observed and stack mol-ecules 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(8)H(7)BrClNO, is syn to the 2-chloro substituent in the aniline ring and anti to both the C=O and C-Br bonds in the side chain, similar to that observed in 2-chloro-N-(2-chloro-phen-yl)acetamide. In the crystal, mol-ecules are linked into chains along the a axis by N-H?O hydrogen bonds. These chains are in turn linked into pairs, in the form of columns, through much weaker C-H?Cl and Br?Br [4.3027?(3)?Å] inter-actions.

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

Project description:The conformation of the N-H bond in the structure of the title compound, C(10)H(12)ClNO, is syn to the ortho methyl group, similar to that observed with respect to the meta methyl group in 2-chloro-N-(3-methyl-phen-yl)acetamide and the ortho-chloro group in 2-chloro-N-(2-chloro-phen-yl)acetamide. The geometric parameters are similar to those of other acetanilides. The mol-ecules are linked into chains through inter-molecular N-H?O hydrogen bonds.

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2-Chloro-N-(2,5-dichloro-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the structure of the title compound, C(8)H(6)Cl(3)NO, is anti to the C=O bond. The N-H H atom shows close intra-molecular N-H?Cl hydrogen bonds with both the ring Cl atom in the ortho position and the side-chain Cl atom. The mol-ecules crystallize in planes parallel to (221).

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N-(4-Chloro-phen-yl)-2,2-diphenyl-acetamide.

Project description:In the title compound, C(20)H(16)ClNO, an S(6) ring motif is formed via an intra-molecular C-H⋯O hydrogen bond. The chloro-substituted benzene ring is almost perpendicular to the benzene rings, forming dihedral angles of 87.33 (9) and 88.69 (9)°. The dihedral angle between the benzene rings is 87.17 (9)°. In the crystal, mol-ecules are linked into chains parallel to the c axis by inter-molecular N-H⋯O hydrogen bonds. The crystal packing also features weak C-H⋯π inter-actions involving the chloro-substituted ring.

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