4-Chloro-N-(2,6-dichlorophenyl)benzamide

Miroslav Tokarčík,Hartmut Fuess,Jozef Kožíšek,B P Sowmya,B Thimme Gowda

doi:10.1107/s160053680902265x

Abstract

The title compound, C13H8Cl3NO, crystallizes with four molecules in the asymmetric unit. In the molecular structure, the conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2)° in the four molecules. The amide group is twisted out of the plane of the anilino ring, as shown by the dihedral angles of 85.4 (1), 74.3 (1), 88.1 (1) and 77.6 (1)° in the four molecules. The aromatic rings are oriented at dihedral angles of 86.6 (1), 78.0 (1), 60.3 (1) and 69.8 (1)° in the four molecules. The crystal structure is stabilized via intermolecular N—H⋯O hydrogen bonds, aromatic aromatic interactions, short Cl⋯Cl contacts and C—H⋯Cl hydrogen bonds. Intermolecular hydrogen bonds connect the molecules into two distinct chains running along the c axis of the crystal. One molecule forms an inversion dimer in which the main interactions are π–π stacking [centroid–centroid distances = 3.749 (1) and 3.760 (1) Å] and a short Cl⋯Cl contact of 3.408 (1) Å.

Highlights

The title compound, C13H8Cl3NO, crystallizes with four molecules in the asymmetric unit
The conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings
The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2) in the four molecules

Summary

Structure Reports

Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, bDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287. The conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2) in the four molecules. The amide group is twisted out of the plane of the anilino ring, as shown by the dihedral angles of 85.4 (1), 74.3 (1), 88.1 (1) and. The crystal structure is stabilized via intermolecular N—H O hydrogen bonds, aromatic aromatic interactions, short Cl Cl contacts and. Intermolecular hydrogen bonds connect the molecules into two distinct chains running along the c axis of the crystal.

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