Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 2 (February 2005)

organic compounds

fg1803 scheme

Acta Cryst. (2005). C61, o114-o117 [doi:10.1107/S0108270104034146]

Two isomeric 2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]hexahydroisoindole-1,3-dione compounds

B. Li, H.-B. Song, C.-T. Hsu, K.-L. Zhang, C. Wu and H.-Z. Yang

Abstract: The molecular structures of 2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]-1,3,4,5,6,7-hexahydroisoindole-1,3-dione, C₁₇H₁₃ClFNO₃, (I), and the isomeric compound 2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]-cis-1,3,3a,4,7,7a-hexahydroisoindole-1,3-dione, (II), are, as anticipated, significantly different in their conformations and in the distances between the farthest two atoms. The six-membered ring of the 1,3,4,5,6,7-hexahydroisoindole-1,3-dione moiety in (I) adopts a half-chair conformation. The dihedral angle between the five-membered dione ring of (I) and the benzene ring is 50.96 (7)°. The six-membered ring of the cis-1,3,3a,4,7,7a-hexahydroisoindole-1,3-dione moiety in (II) adopts a boat conformation. The dihedral angle in (II) between the five-membered dione ring and the benzene ring is 61.03 (13)°. In the crystal structures, the molecules are linked by C-HO hydrogen bonds and weak [bold pi] - interactions. Compound (I) is a much more potent herbicide than (II). The ClH distances between the farthest two atoms in (I) and (II) are 11.37 and 9.97 Å, respectively.

Formula: Two isomers of C₁₇H₁₃ClFNO₃


	Structure factor file (CIF format) (157.4 kbytes) Contains datablock II

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