(1S,3R,8R,9S,11R)-2,2,10,10-Tetra­chloro-3,7,7,11-tetra­methyl­tetra­cyclo­[6.5.0.01,3.09,11]trideca­ne

Ourhriss, N.; Benharref, A.; Saadi, M.; El Ammari, L.; Berraho, M.

doi:10.1107/S1600536813001700

Volume 69
Part 2
Page o275
February 2013

Received 14 January 2013
Accepted 16 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.085
Data-to-parameter ratio = 28.5
Details

(1S,3R,8R,9S,11R)-2,2,10,10-Tetrachloro-3,7,7,11-tetramethyltetracyclo[6.5.0.0^1,3.0^9,11]tridecane

Najia Ourhriss,^a ^* Ahmed Benharref,^a Mohamed Saadi,^b Lahcen El Ammari ^b and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité "Unité Associée au CNRST(URAC16)", Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C₁₇H₂₄Cl₄, was synthesized from [beta] -himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The molecule is built up from fused six- and seven-membered rings and two three-membered rings from the reaction of [beta] -himachalene with dichlorocarbene. The six-membered ring shows a chair conformation, whereas the seven-membered ring displays a boat conformation.

Related literature

For the isolation of [beta] -himachalene, see: Joseph & Dev (1968); Plattier & Teisseire (1974). For the reactivity of this sesquiterpene, see: Lassaba et al. (1998); Chekroun et al. (2000); El Jamili et al. (2002); Sbai et al. (2002); Dakir et al. (2004). For its biological activity, see: Daoubi et al. (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₂₄Cl₄
M_r = 370.16
Monoclinic, P 2₁
a = 8.8807 (6) Å
b = 11.6280 (8) Å
c = 9.0596 (6) Å
= 107.665 (2)°
V = 891.42 (10) Å³
Z = 2
Mo K radiation
= 0.66 mm^-1
T = 296 K
0.41 × 0.35 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer
15112 measured reflections
5419 independent reflections
4910 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.085
S = 1.03
5419 reflections
190 parameters
1 restraint
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.19 e Å^-3
Absolute structure: Flack (1983)
Flack parameter: 0.04 (4)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6883 ).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chekroun, A., Jarid, A., Benharref, A. & Boutalib, A. (2000). J. Org. Chem. 65, 4431-4434.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dakir, M., Auhmani, A., Ait Itto, M. Y., Mazoir, N., Akssira, M., Pierrot, M. & Benharref, A. (2004). Synth. Commun. 34, 2001-2008.
Daoubi, M., Duran -Patron, R., Hmamouchi, M., Hernandez -Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927-932.
El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645-6648.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Joseph, T. C. & Dev, S. (1968). Tetrahedron, 24, 3841-3859.
Lassaba, E., Eljamili, H., Chekroun, A., Benharref, A., Chiaroni, A., Riche, C. & Lavergne, J.-P. (1998). Synth. Commun. 28, 2641-2651.
Plattier, M. & Teisseire, P. (1974). Recherche, 19, 131-144.
Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.