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Volume 69 
Part 11 
Pages o1692-o1693  
November 2013  

Received 24 September 2013
Accepted 14 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 17.8
Details
Open access

Absolute configuration of (1S,3R,8R)-10-bromo­methyl-2,2-di­chloro-3,7,7-tri­methyl­tri­cyclo­[6.4.0.01,3]dodec-9-ene

aLaboratoire de Physico-Chimie Moléculaire et Synthése Organique, Département de Chimie Faculté des Sciences, Semlalia BP 2390, Marrakech 40001, Morocco, and bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
Correspondence e-mail: itto35@hotmail.com

The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The mol­ecular packing within the crystal is stabilized only by van der Waals inter­actions.

Related literature

For the synthesis of the title compound, see: El Jamili et al. (2002[El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645-6648.]). For further synthetic details, see: Qu et al. (2009[Qu, J.-P., Deng, C., Zhou, J., Sun, X.-L. & Tang, Y. (2009). J. Org. Chem. 74, 7684-7689.]). For biological properties of cyclo­propane-containing products, see: Ajay Kumar et al. (2012[Ajay Kumar, K., Lokanatha Rai, K. M., Vasanth Kumar, G. & Mylarappa, B. N. (2012). Int. J. Pharm. Pharm. Sci. 4, Suppl. 4, 564-568.]); Sow et al. (2007[Sow, G. J., Ndams, I. S., Kogi, E., Tukur, Z. & Adamu, H. (2007). Sci. World J. 2, 5-8.]); Symon et al. (2005[Symon, A. V., Veselova, N. N., Kaplun, A. P., Vlasenkova, N. K., Fedorova, G. A., Liutik, A. I., Gerasimova, G. K. & Shvets, V. I. (2005). Russ. J. Bioorg. Chem. 31, 320-325.]). For related structures, see: Benharref et al. (2010[Benharref, A., El Ammari, L., Berraho, M. & Lassaba, E. (2010). Acta Cryst. E66, o2463.]); Gassman & Gorman (1990[Gassman, P. G. & Gorman, D. B. (1990). J. Am. Chem. Soc. 112, 8624-8626.]); Lassaba et al. (1997[Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.]). For conformations of rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Boessenkool & Boyens (1980[Boessenkool, I. K. & Boyens, J. C. A. (1980). J. Cryst. Mol. Struct. 10, 11-18.]); For absolute structure, see: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]); Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]); Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C16H23BrCl2

  • Mr = 366.15

  • Orthorhombic, P 21 21 21

  • a = 9.1000 (2) Å

  • b = 12.5490 (4) Å

  • c = 14.4070 (5) Å

  • V = 1645.22 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 6.26 mm-1

  • T = 173 K

  • 0.45 × 0.25 × 0.10 mm

Data collection
  • Agilent Xcalibur Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.397, Tmax = 1.000

  • 9248 measured reflections

  • 3127 independent reflections

  • 3012 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.070

  • S = 1.04

  • 3127 reflections

  • 176 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1307 Friedel pairs

  • Absolute structure parameter: -0.015 (17)

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2099 ).


References

Agilent (2012). CrysAlis PRO Agilent Technologies Ltd, Yarnton, England.
Ajay Kumar, K., Lokanatha Rai, K. M., Vasanth Kumar, G. & Mylarappa, B. N. (2012). Int. J. Pharm. Pharm. Sci. 4, Suppl. 4, 564-568.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Benharref, A., El Ammari, L., Berraho, M. & Lassaba, E. (2010). Acta Cryst. E66, o2463.  [CSD] [CrossRef] [IUCr Journals]
Boessenkool, I. K. & Boyens, J. C. A. (1980). J. Cryst. Mol. Struct. 10, 11-18.  [CrossRef] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645-6648.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gassman, P. G. & Gorman, D. B. (1990). J. Am. Chem. Soc. 112, 8624-8626.  [CrossRef] [ChemPort] [Web of Science]
Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943-1945.  [CSD] [CrossRef] [IUCr Journals]
Qu, J.-P., Deng, C., Zhou, J., Sun, X.-L. & Tang, Y. (2009). J. Org. Chem. 74, 7684-7689.  [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sow, G. J., Ndams, I. S., Kogi, E., Tukur, Z. & Adamu, H. (2007). Sci. World J. 2, 5-8.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Symon, A. V., Veselova, N. N., Kaplun, A. P., Vlasenkova, N. K., Fedorova, G. A., Liutik, A. I., Gerasimova, G. K. & Shvets, V. I. (2005). Russ. J. Bioorg. Chem. 31, 320-325.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1692-o1693   [ doi:10.1107/S1600536813028183 ]

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