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Issue 1, 2008
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Hydrogen bonding patterns in a series of 1-arylcycloalkanecarboxamides

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Single-crystal structures of five 1-arylcycloalkanecarboxamides, viz.1-phenylcyclopentanecarboxamide (1), 1-phenylcyclohexanecarboxamide (2), 1-(2-fluorophenyl)cyclohexanecarboxamide (3), 1-(2-chlorophenyl)cyclohexanecarboxamide (4) and 1-(2-bromophenyl)-cyclohexanecarboxamide (5), are reported. The primary hydrogen-bonded motif consists of centrosymmetric or non-centrosymmetric R22(8) dimers between the carboxamide functional groups. In compound 1, the dimers are further linked by hydrogen bonds to form infinite two-dimensional sheets, while in 4 and 5 additional hydrogen bonding with molecules not involved in dimer formation links the dimers into infinite chains. The cycloalkane rings in the five compounds adopt noticeably different conformations. As a consequence of these various effects, none of the five compounds is isostructural.

Graphical abstract: Hydrogen bonding patterns in a series of 1-arylcycloalkanecarboxamides

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The article was received on 04 Jun 2007, accepted on 04 Sep 2007 and first published on 13 Sep 2007

Article type: Paper
DOI: 10.1039/B708333E
Citation: CrystEngComm, 2008,10, 95-102

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    Hydrogen bonding patterns in a series of 1-arylcycloalkanecarboxamides

    A. Lemmerer and J. P. Michael, CrystEngComm, 2008, 10, 95
    DOI: 10.1039/B708333E

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