Koetjapic acid chloroform hemisolvate

Z D Nassar,Chin Sing Yeap,Hoong-Kun Fun,A M S Abdul Majid,A F A Aisha

doi:10.1107/s1600536810016430

Z D Nassar, Chin Sing Yeap + Show 3 more

Open Access

https://doi.org/10.1107/s1600536810016430

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Abstract

The asymmetric unit of the title compound, C30H46O4·0.5CHCl3, consists of one koetjapic acid [systematic name: (3R,4aR,4bS,7S,8S,10bS,12aS)-7-(2-carboxyethyl)-3,4b,7,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,7,8,9,10,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid] molecule and one half-molecule of chloroform solvent, which is disordered about a twofold rotation axis. The symmetry-independent component is further disordered over two sites, with occupancies of 0.30 and 0.20. The koetjapic acid contains a fused four-ring system, A/B/C/D. The A/B, B/C and C/D junctions adopt E/trans/cis configurations, respectively. The conformation of ring A is intermediate between envelope and half-chair and ring B adopts an envelope conformation whereas rings C and D adopt chair conformations. A weak intramolecular C—H⋯O hydrogen bond is observed. The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O—H⋯O hydrogen bonds. The dimers are stacked along the c axis.

Highlights

The asymmetric unit of the title compound, C30H46O40.5CHCl3, consists of one koetjapic acid [systematic name: (3R,4aR,4bS,7S,8S,10bS,12aS)-7-(2-carboxyethyl)-3,4b,7,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,7,8,9,10,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid] molecule and one half-molecule of chloroform solvent, which is disordered about a twofold rotation axis
The conformation of ring A is intermediate between envelope and half-chair and ring B adopts an envelope conformation whereas rings C and D adopt chair conformations
The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O—H O hydrogen bonds

Summary

Crystal data

Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.005 Å; disorder in solvent or counterion; R factor = 0.060; wR factor = 0.169; data-toparameter ratio = 13.0. The asymmetric unit of the title compound, C30H46O40.5CHCl3, consists of one koetjapic acid [systematic name:. (3R,4aR,4bS,7S,8S,10bS,12aS)-7-(2-carboxyethyl)-3,4b,7,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,7,8,9,10,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid] molecule and one half-molecule of chloroform solvent, which is disordered about a twofold rotation axis. The symmetryindependent component is further disordered over two sites, with occupancies of 0.30 and 0.20. The koetjapic acid contains a fused four-ring system, A/B/C/D. A weak intramolecular C—H O hydrogen bond is observed. The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O—H O hydrogen bonds. The dimers are stacked along the c axis

Bruker APEXII DUO CCD areadetector diffractometer

Graphite monochromator φ and ω scans

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