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-HO 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-C_ar 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-HO_imide hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong intermolecular carboxylic acid O-HO 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


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

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

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

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

Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

Search: From to Advanced search