Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 1 (January 2004)



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Acta Cryst. (2004). C60, o9-o11    [doi:10.1107/S0108270103026520]

Two isomers of 2,4-dibenzyl-8-azabicyclo[3.2.1]octan-3-ol

G.-R. Zheng, S. Parkin, L. P. Dwoskin and P. A. Crooks

Abstract: The crystal structures of the title compounds, 2[alpha],4[alpha]-dibenzyl-3[alpha]-tropanol (2[alpha],4[alpha]-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octan-3[alpha]-ol), C22H27NO, (I), and 2[alpha],4[alpha]-dibenzyl-3[beta]-tropanol (2[alpha],4[alpha]-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octan-3[beta]-ol), C22H27NO, (II), show that both compounds have a piperidine ring in a chair conformation and a pyrrolidine ring in an envelope conformation. Isomer (I) is asymmetric, the benzyl groups having different orientations, whereas isomer (II) is mirror symmetric, and the N and O atoms, the C atom attached to the hydroxy group, and the methyl C atom attached to the N atom lie on the mirror plane. In the crystal structures of both (I) and (II), the molecules are linked together by intermolecular O-H...N hydrogen bonds to form chains that run parallel to the a direction in (I) and parallel to b in (II).

Formula: C22H27NO and C22H27NO

Online 6 December 2003


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Structure factor file (CIF format) (204.4 kbytes)
Contains datablock I


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Structure factor file (CIF format) (53.8 kbytes)
Contains datablock II


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