Cyclohexanecarboxamide

Acta Crystallogr C. 2009 Nov;65(Pt 11):o553-4. doi: 10.1107/S0108270109036440. Epub 2009 Oct 7.

Abstract

The title compound, C(7)H(13)NO, forms R(2)(2)(8) N-H...O hydrogen-bonded dimers and C4 N-H...O-linked chains, which are further stabilized by a C-H...O interaction. The combination of these interactions results in a hydrogen-bonded network parallel to (100), with a motif that can be described by the secondary graph set R(4)(6)(16). The existence of the same hydrogen-bonding motif in 1-phenylcyclopentanecarboxamide and 1-(2-bromophenyl)cyclohexanecarboxamide [Lemmerer & Michael (2008). CrystEngComm, 10, 95-102 indicates that replacing the H atom on position 1 with a more bulky group does not necessarily disrupt the observed hydrogen-bonding pattern. The presence of a C-H...O interaction to stabilize the R(4)(6)(16) network does, however, seem to be required. In addition, the title compound is isomorphous with a previously published structure of cyclopentanecarboxamide [Winter et al. (1981). Acta Cryst. B37, 2183-2185].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cyclohexanes / chemistry*
  • Cyclopentanes / chemistry*
  • Hydrogen Bonding

Substances

  • 1-(2-bromophenyl)cyclohexanecarboxamide
  • 1-phenylcyclopentanecarboxamide
  • Cyclohexanes
  • Cyclopentanes