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The diastereoisomeric title compounds,  5  and  6 , were obtained as a result of intramolecular electrohydrocyclisation of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate. The common feature of the molecular structures is the presence of a central, eight-membered, –C(H)–C(H)–C  C–(CH 2 ) 2 –C  C, ring appended to a cyclopentenyl and two phenyl rings. This study represents an unprecedented structural characterisation of such an atomic/bonding arrangement. The distinctive feature of the structures relates to the conformation of the central rings, i.e. approximating a boat in  5  and a chair in  6 . This difference in molecular conformations arises from the different configurations at the methine-C atoms of the cyclopentenyl ring, i.e.  R - and  S - (or  S - and  R -) in  5  as opposed to  R - and  R - (or  S - and  S -) in  6 . In each case, the hydroxyl-OH forms an intramolecular hydrogen-bond to the adjacent carbonyl-O atom so the molecular packing in each of  5  and  6  is sustained by non-conventional interactions. A three-dimensional architecture in  5  arises from a combination of phenyl-C–H…O(carbonyl) and methyl- and methylene-C–H…π contacts. In the crystal of  6 , supramolecular chains with a zig-zag topology along the  c -axis are formed via methyl-C–H…O(hydroxyl); the chains pack with no directional interactions between them.

zeitschrift für kristallographie - crystalline materials

Novel diastereoisomers of C 21 H 20 O 3  obtained from the cathodic reduction of methyl (2E)-3-[2-(2-{2-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}ethyl)phenyl]prop-2-enoate