2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide

Grzegorz Dutkiewicz,B Narayana,Maciej Kubicki,B P Siddaraju,H S Yathirajan

doi:10.1107/s1600536810003375

Abstract

In the title compound, C15H10Cl3NO2, an intramolecular N—H⋯O hydrogen bond forms a six-membered ring and enforces an almost coplanar conformation for the acetamido group, the central benzene ring and the bridging carbonyl C—C(=O)—C group: the dihedral angles between the benzene ring and the acetamide and carbonyl C—C(=O)—C planes are 7.06 (11) and 7.17 (12)°, respectively. The dihedral angle between the two benzene rings is 67.43 (9)°. Because a strong hydrogen-bond donor is involved in the intramolecular interaction, the crystal packing is determined by weak C—H⋯O and C—H⋯Cl interactions.

Highlights

C15H10Cl3NO2, an intramolecular N— HÁ Á ÁO hydrogen bond forms a six-membered ring and enforces an almost coplanar conformation for the acetamido group, the central benzene ring and the bridging carbonyl C— C( O)—C group: the dihedral angles between the benzene ring and the acetamide and carbonyl C—C( O)—C planes are 7.06 (11) and 7.17 (12), respectively
Because a strong hydrogen-bond donor is involved in the intramolecular interaction, the crystal packing is determined by weak C— HÁ Á ÁO and C—HÁ Á ÁCl interactions
The title compound is isostructural with 2-chloroacetamido-5chloro-20-fluorobenzophenone (Prasanna & Guru Row, 2000)

Summary

Structure Reports Online

Key indicators: single-crystal X-ray study; T = 295 K; mean (C–C) = 0.004 A; R factor = 0.043; wR factor = 0.113; data-to-parameter ratio = 12.7. C15H10Cl3NO2, an intramolecular N— HÁ Á ÁO hydrogen bond forms a six-membered ring and enforces an almost coplanar conformation for the acetamido group, the central benzene ring and the bridging carbonyl C— C( O)—C group: the dihedral angles between the benzene ring and the acetamide and carbonyl C—C( O)—C planes are 7.06 (11) and 7.17 (12), respectively. The dihedral angle between the two benzene rings is 67.43 (9). Because a strong hydrogen-bond donor is involved in the intramolecular interaction, the crystal packing is determined by weak C— HÁ Á ÁO and C—HÁ Á ÁCl interactions

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