Cyclohexanecarboxamide.
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].
Zipp
Caitlin F
CF
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa.
Fernandes
Manuel A
MA
Michael
Joseph P
JP
Winks
Susan
S
D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D006860:Hydrogen Bonding
C545466:1-(2-bromophenyl)cyclohexanecarboxamide; C545465:1-phenylcyclopentanecarboxamide; D003510:Cyclohexanes; D003517:Cyclopentanes