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Volume 69 
Part 7 
Pages o1162-o1163  
July 2013  

Received 26 April 2013
Accepted 19 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.080
Data-to-parameter ratio = 16.2
Details
Open access

(3R*,6R*,4'S*,8'R*,3''R*,6''R*)-3,3''-Diisopropyl-6,6''-dimethyl-2',6'-diphenyldispiro[cyclohexane-1,4'-(3,7-dioxa-2,6-diazabicyclo[3.3.0]octane)-8',1''-cyclohexane]-2,2''-dione

aLaboratoire des Substances Naturelles et Synthèse et Dynamique Moléculaire, Faculté des Sciences et Techniques, Errachidia, Morocco,bLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205 route de Narbonne, 31077 Toulouse cedex, France, and cLaboratoire de Chimie Physique des Matériaux, Faculté des Sciences et Techniques, BP 509, Errachidia, Morocco
Correspondence e-mail: med.azrour@gmail.com

The two oxazolidine rings (A and B) of the title compound, C34H44N2O4, display roughly half-chair conformations, which could be described as twisted on the C-O bond. Together, the fused oxazolidine rings have a butterfly shape, with the H atoms attached to the ring junction C atoms in a cis orientation. The cyclohexane rings of both p-menthone fragments display chair conformations. The absolute configuration could not be determined from the X-ray diffraction data, but the relative configuration of the stereocentres could be deduced.

Related literature

For a related synthesis, see: Brüning et al. (1973[Brüning, I., Grashey, R., Hauck, R. & Seidel, H. (1973). Org. Synth. Coll. Vol. 5, 1124-1129.]); Tanka et al. (1972[Tanka, A., Tanka, R., Uda, H. & Yosikoshi, A. (1972). J. Chem. Soc. Perkin Trans. 1, pp. 1721-1727.]). For the properties of p-menthane derivatives, see: Ito et al. (2009[Ito, F., Kumamoto, T., Yamagachi, K. & Ishikawa, T. (2009). Tetrahedron, 65, 771-785.]); Kharchouf et al. (2011[Kharchouf, S., Majidi, L., Bouklah, M., Hammouti, B., Bouyanzer, A. & Aouniti, A. (2011). Arabian J. Chem. doi:10.1016/j.arabjc.2010.12.002.], 2012[Kharchouf, S., Majidi, L., Znini, M., Costa, J., Hammouti, B. & Paolini, J. (2012). Int. J. Electrochem. Sci. 7, 10325-10337.]); Majidi et al. (2010[Majidi, L., Faska, Z., Znini, M., Kharchouf, S., Bouyanzer, A. & Hammouti, B. (2010). J. Mater. Environ. Sci. 1, 219-226.]); Clark (1990[Clark, G. S. (1990). Perfum. Flavor. 15, 42-44.]); Umemoko (1998[Umemoko, K. (1998). Nat. Prod. Lett. 11, 161-165.]); Boelens (1993[Boelens, M. H. (1993). Perfum. Flavor. 18, 27-30.]); Wagner et al. (2004[Wagner, E., Becan, L. & Nowakowska, E. (2004). Bioorg. Med. Chem. 12, 265-269.]). For related structures, see: Iball et al. (1968[Iball, J., Motherwell, W. D. S., Pollock, J. J. S. & Tedder, J. M. (1968). Chem. Commun. pp. 365-366.], 1986[Iball, J., Motherwell, W. D. S., Barnes, J. C. & Golnazarians, W. (1986). Acta Cryst. C42, 239-241.]); Aurich et al. (1989[Aurich, H. G., Baum, G., Massa, W. & Mogendorf, K.-D. (1989). Acta Cryst. C45, 760-763.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C34H44N2O4

  • Mr = 544.71

  • Orthorhombic, P 21 21 21

  • a = 9.5037 (6) Å

  • b = 12.4162 (10) Å

  • c = 24.8982 (18) Å

  • V = 2938.0 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 180 K

  • 0.37 × 0.13 × 0.06 mm

Data collection
  • Agilent Xcalibur diffractometer

  • Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.908, Tmax = 1.000

  • 24309 measured reflections

  • 5963 independent reflections

  • 3751 reflections with I > 2[sigma](I)

  • Rint = 0.098

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.080

  • S = 0.87

  • 5963 reflections

  • 367 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and 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: FY2097 ).


References

Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
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]
Aurich, H. G., Baum, G., Massa, W. & Mogendorf, K.-D. (1989). Acta Cryst. C45, 760-763.  [CrossRef] [IUCr Journals]
Boelens, M. H. (1993). Perfum. Flavor. 18, 27-30.  [ChemPort]
Brüning, I., Grashey, R., Hauck, R. & Seidel, H. (1973). Org. Synth. Coll. Vol. 5, 1124-1129.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Clark, G. S. (1990). Perfum. Flavor. 15, 42-44.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Iball, J., Motherwell, W. D. S., Barnes, J. C. & Golnazarians, W. (1986). Acta Cryst. C42, 239-241.  [CrossRef] [IUCr Journals]
Iball, J., Motherwell, W. D. S., Pollock, J. J. S. & Tedder, J. M. (1968). Chem. Commun. pp. 365-366.
Ito, F., Kumamoto, T., Yamagachi, K. & Ishikawa, T. (2009). Tetrahedron, 65, 771-785.  [Web of Science] [CrossRef] [ChemPort]
Kharchouf, S., Majidi, L., Bouklah, M., Hammouti, B., Bouyanzer, A. & Aouniti, A. (2011). Arabian J. Chem. doi:10.1016/j.arabjc.2010.12.002.
Kharchouf, S., Majidi, L., Znini, M., Costa, J., Hammouti, B. & Paolini, J. (2012). Int. J. Electrochem. Sci. 7, 10325-10337.  [ChemPort]
Majidi, L., Faska, Z., Znini, M., Kharchouf, S., Bouyanzer, A. & Hammouti, B. (2010). J. Mater. Environ. Sci. 1, 219-226.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tanka, A., Tanka, R., Uda, H. & Yosikoshi, A. (1972). J. Chem. Soc. Perkin Trans. 1, pp. 1721-1727.
Umemoko, K. (1998). Nat. Prod. Lett. 11, 161-165.
Wagner, E., Becan, L. & Nowakowska, E. (2004). Bioorg. Med. Chem. 12, 265-269.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1162-o1163   [ doi:10.1107/S1600536813017054 ]

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