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Studies in crystal engineering: topochemical photodimerization and structure of p-chlorobenzylidene-DL-piperitone

Venugopalan, P and Venkatesan, K (1990) Studies in crystal engineering: topochemical photodimerization and structure of p-chlorobenzylidene-DL-piperitone. In: Acta Crystallographica, Section B: Structural Science, 46 (6). pp. 826-830.

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3-(p-Chlorophenylvinyl)-6-isopropyl-2-cyclohexen- 1 -one, $C_{17}H_{19}CIO$, $M_r$=274"7, triclinic, P1, a =6.636(1), b=10.537(2), c=10.811(3) A, $\alpha$=95.31 (2), $\beta$ = 92"60 (2), $\gamma$ = 100.66$(2)^°$, V = 738.2 (2) $\AA^3$, Z = 2, O m = 1.23, $D_x$ = 1.236 Mg $m^{-3}$, Cu K$\alpha$, $\lambda$ = 1.5418 $\AA$,$\mu$ = 2.09 $mm^{-l}$, F(000) = 292, T = 298 K, R = 0-050 for 2220 observed reflections. The title compound undergoes a topochemical photodimerization giving an anti head-to-tail dimmer instead of the syn head-to-head dimer expected on the basis of the ability of the chloro group to steer $\beta$-type packing. There are no significant C1...C1 intermolecular interactions. Possible reasons for the observed a-type packing of benzylidenepiperitones are advanced. The low dimer yield is also rationalized.

Item Type: Journal Article
Publication: Acta Crystallographica, Section B: Structural Science
Publisher: International Union of Crystallography
Additional Information: Copyright of this article belongs to International Union of Crystallography
Keywords: Crystal Engineering;Topochemical Photodimerization;p-Chlorobenzylidene-nL-piperitone
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 13 Nov 2007
Last Modified: 19 Sep 2010 04:41
URI: http://eprints.iisc.ac.in/id/eprint/12454

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