Crystal structure of (1 S ,3 R ,8 R ,10 S )-2,2-dichloro-10-hydroxy-3,7,7,10-tetramethyltricyclo[6.4.0.0 1,3 ]dodecan-9-one

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 72; no. 5; pp. 709 - 711
• Main Authors: Benzalim, Ahmed, Auhmani, Aziz, Ait Itto, My Youssef, Daran, Jean-Claude, Abdelwahed, Auhmani
• Format: Journal Article
• Language: English
• Published: International Union of Crystallography 01-05-2016
• Subjects: absolute configuration; asymmetric synthesis; Chemical Sciences; Coordination chemistry; crystal structure; hydrogen bonding; natural products; α-hydroxyketone
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989016006174

The asymmetric unit of the title compound, C
16
H
24
Cl
2
O
2
, contains two independent molecules (
A
and
B
) which are built from three fused rings,
viz.
a seven-membered heptane ring, a six-membered cyclohexyl ring bearing a ketone and an alcohol group, and a cyclopropane ring bearing two Cl atoms. In the crystal, the two molecules are linked
via
two O—H...O hydrogen bonds, forming an
A
–
B
dimer with an
R
2
2
(10) ring motif. The
A
molecules of these dimers are linked
via
a C—H...O hydrogen bond, forming chains propagating along the
a
-axis direction. Both molecules have the same absolute configuration,
i.e.
1
S
,3
R
,8
R
,10
S
, which is based on the synthetic pathway and further confirmed by resonant scattering [Flack parameter = 0.03 (5)].