Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 7 (July 2004)

gg1216 scheme

Acta Cryst. (2004). C60, o536-o538 [doi:10.1107/S0108270104013551]

1-Chloro-3,6-dimethoxy-2,5-dimethylbenzene and 1-chloro-3,6-dimethoxy-2,4-dimethylbenzene

D. J. Wiedenfeld, V. N. Nesterov, M. A. Minton and C. L. Montoya

Abstract: The title compounds, 1-chloro-3,6-dimethoxy-2,5-dimethylbenzene, (IIIa), and 1-chloro-3,6-dimethoxy-2,4-dimethylbenzene, (IIIb), both C₁₀H₁₃ClO₂, were obtained from 2,5- and 2,6-dimethyl-1,4-benzoquinone, respectively, and are intermediates in the synthesis of ammonium quinone derivatives. The isomers have different substituents around the methoxy groups and crystallize in different space groups. In both molecules, the methoxy groups each have different orientations with respect to the benzene ring. In both cases, one methoxy group lies in the plane of the ring and can participate in conjugation with the aromatic system, while the second is almost perpendicular to the plane of the aromatic ring. The C-O-C bond angles around these substituents are also different: 117.5 (4) and 118.2 (3)° in (IIIa) and (IIIb), respectively, when the methoxy groups lie in the plane of the ring, and 114.7 (3) and 113.6 (3)° in (IIIa) and (IIIb), respectively, when they are out of the plane of the ring.

Formula: Two isomers of C₁₀H₁₃ClO₂

Online 30 July 2004


	Structure factor file (CIF format) (74.4 kbytes) Contains datablock IIIa

	Structure factor file (CIF format) (76.8 kbytes) Contains datablock IIIb

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