Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 7 (July 2012)

organic compounds

fg3250 scheme

Acta Cryst. (2012). C68, o253-o256 [ doi:10.1107/S010827011202447X ]

Cyclic imides and an open-chain amide carboxylic acid from the facile reaction of cis-cyclohexane-1,2-carboxylic anhydride with the isomeric monofluoroanilines

G. Smith and U. D. Wermuth

Abstract: The structures of the cyclic imides cis-2-(2-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione, C₁₄H₁₄FNO₂, (I), and cis-2-(4-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindoline-1,3-dione, C₁₄H₁₄FNO₂, (III), and the open-chain amide acid rac-cis-2-[(3-fluorophenyl)carbamoyl]cyclohexane-1-carboxylic acid, C₁₄H₁₆FNO₃, (II), are reported. Cyclic imides (I) and (III) are conformationally similar, with comparable ring rotations about the imide N-C_ar bond [the dihedral angles between the benzene ring and the five-membered isoindole ring are 55.40 (8)° for (I) and 51.83 (7)° for (III)]. There are no formal intermolecular hydrogen bonds involved in the crystal packing of either (I) or (III). With the acid (II), in which the meta-related F-atom substituent is rotationally disordered (0.784:0.216), the amide group lies slightly out of the benzene plane [the interplanar dihedral angle is 39.7 (1)°]. Intermolecular amide-carboxyl N-HO hydrogen-bonding interactions between centrosymmetrically related molecules form stacks extending down b, and these are linked across c by carboxyl-amide O-HO hydrogen bonds, giving two-dimensional layered structures which lie in the (011) plane. The structures reported here represent examples of compounds analogous to the phthalimides or phthalanilic acids and have little precedence in the crystallographic literature.

Formula: C₁₄H₁₄FNO₂, C₁₄H₁₆FNO₃ and C₁₄H₁₄FNO₂


	Chemical Markup Language (CML) file (4.9 kbytes) [ doi:10.1107/S010827011202447X/fg3250Isup5.cml ] Supplementary material

	Chemical Markup Language (CML) file (5.2 kbytes) [ doi:10.1107/S010827011202447X/fg3250IIsup6.cml ] Supplementary material

	Chemical Markup Language (CML) file (4.9 kbytes) [ doi:10.1107/S010827011202447X/fg3250IIIsup7.cml ] Supplementary material

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