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13-cis-Retinoic acid, [(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-2,4,6,8-nonatetraenoic acid, C20H28O2] was found to adopt the 6-s-trans conformation, with the ring double bond and all the C atoms of the polyene chain coplanar. The plane of the double-bond system is coincident with a crystallographic mirror plane. The crystal displays crystallographic symmetry arising from disorder; indeed the cyclohexene ring, in a half-chair conformation, is present in two equally occupied conformations related to each other by the mirror plane. The carboxylic group is also disordered, lying on opposite sides of the plane of the double-bond system. In the crystal the molecules form dimers connected by hydrogen bonds involving the carboxylic groups and the dimers pack in parallel layers.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks 55aceo, global

fcf

Structure factor file (CIF format)
Contains datablock 55aceo

CCDC reference: 128605

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