Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 9 (September 2012)

organic compounds

bm3120 scheme

Acta Cryst. (2012). C68, o327-o331    [ doi:10.1107/S0108270112030168 ]

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction of cis-cyclohexane-1,2-carboxylic anhydride with o- and p-anisidine and m- and p-aminobenzoic acids

G. Smith and U. D. Wermuth

Abstract: The structures of the open-chain amide carboxylic acid rac-cis-2-[(2-methoxyphenyl)carbamoyl]cyclohexane-1-carboxylic acid, C15H19NO4, (I), and the cyclic imides rac-cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione, C15H17NO3, (II), chiral cis-3-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, C15H15NO4, (III), and rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid monohydrate, C15H15NO4·H2O, (IV), are reported. In the amide acid (I), the phenylcarbamoyl group is essentially planar [maximum deviation from the least-squares plane = 0.060 (1) Å for the amide O atom] and the molecules form discrete centrosymmetric dimers through intermolecular cyclic carboxy-carboxy O-H...O hydrogen-bonding interactions [graph-set notation R22(8)]. The cyclic imides (II)-(IV) are conformationally similar, with comparable benzene ring rotations about the imide N-Car bond [dihedral angles between the benzene and isoindole rings = 51.55 (7)° in (II), 59.22 (12)° in (III) and 51.99 (14)° in (IV)]. Unlike (II), in which only weak intermolecular C-H...Oimide hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong intermolecular carboxylic acid O-H...O hydrogen-bonding associations. With (III), these involve imide O-atom acceptors, giving one-dimensional zigzag chains [graph-set C(9)], while with the monohydrate (IV), the hydrogen bond involves the partially disordered water molecule which also bridges molecules through both imide and carboxy O-atom acceptors in a cyclic R44(12) association, giving a two-dimensional sheet structure. The structures reported here expand the structural database for compounds of this series formed from the facile reaction of cis-cyclohexane-1,2-dicarboxylic anhydride with substituted anilines, in which there is a much larger incidence of cyclic imides compared to amide carboxylic acids.

Formula: C15H19NO4, C15H17NO3, C15H15NO4 and C15H15NO4·H2O

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Chemical Markup Language (CML) file (5.6 kbytes)
[ doi:10.1107/S0108270112030168/bm3120Isup6.cml ]
Supplementary material

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Chemical Markup Language (CML) file (5.4 kbytes)
[ doi:10.1107/S0108270112030168/bm3120IIsup7.cml ]
Supplementary material

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Chemical Markup Language (CML) file (5.4 kbytes)
[ doi:10.1107/S0108270112030168/bm3120IIIsup8.cml ]
Supplementary material

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Chemical Markup Language (CML) file (5.7 kbytes)
[ doi:10.1107/S0108270112030168/bm3120IVsup9.cml ]
Supplementary material


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