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Volume 69 
Part 8 
Page o1314  
August 2013  

Received 10 July 2013
Accepted 19 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.106
Data-to-parameter ratio = 7.3
Details
Open access

1,10,10-Trimethyl-5-phenyl-3-oxa-4-azatricyclo[5.2.1.02,6]dec-4-en-2-ol

aLaboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia, BP 2390, 40001 Marrakech, Morocco,bLaboratoire des Matériaux Inorganiques, UMR CNRS 6002, Université Blaise Pascal, 24 Avenue des Landais, 63177 Aubière, France, and cLaboratoire de Chimie des Substances Naturelles, Unité Associé au CNRST (URAC16), Faculté des Sciences-Semlalia, BP 2390, Boulevard My Abdellah, 40000 Marrakech, Morocco
Correspondence e-mail: berraho@uca.ma

The title compound, C17H21NO2, was synthesized by the reaction of (1R)-(+)-3-benzylcamphor and hydroxylamine. The oxazole ring makes a dihedral angle of 23.42 (16)° with the phenyl ring. The six-membered ring of the norboryl group adopts a boat conformation, whereas each of the five-membered rings of the norboryl group displays a flattened envelope conformation, with the C atom carrying the methyl groups representing the flap for both rings. In the crystal, molecules are linked into zigzag chains propagating along the b axis by O-H...N hydrogen bonds.

Related literature

For the functionalization of camphor, see: Jennings & Herschbach (1965[Jennings, B. H. & Herschbach, G. B. (1965). J. Org. Chem. 30, 3902-3909.]); Pastrán et al., (2011[Pastrán, J., Ineichen, E., Agrifoglio, G., Linden, A. & Dorta, R. (2011). Acta Cryst. E67, o188-o189.]). For transition metal complexes of camphor, see: Spannenberg et al. (2002[Spannenberg, A., Fdil, N., El Firdoussi, L. & Karim, A. (2002). Z. Kristallogr. New Cryst. Struct. 217, 549-550.]); Harrad et al. (2010[Harrad, M. A., Valerga, P., Puerta, M. C., Ali, M. A., El Firdoussi, L. & Karim, A. (2010). Acta Cryst. E66, m281.]); Ait Ali et al. (2006[Ait Ali, M., Karim, A., Castanet, Y., Mortreux, A. & Mentré, O. (2006). Acta Cryst. E62, m3160-m3162.]); Gaudo et al. (2011[Gaudo, T., Bleifu, S. M., Müller, A. L., Roth, T., Hoffmann, S., Heinemann, W. F. & Burzlaff, N. (2011). Dalton Trans. 40, 6547-6554.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21NO2

  • Mr = 271.35

  • Monoclinic, C 2

  • a = 22.1681 (18) Å

  • b = 6.6134 (5) Å

  • c = 10.7358 (8) Å

  • [beta] = 108.277 (3)°

  • V = 1494.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.58 × 0.34 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.627, Tmax = 0.745

  • 4379 measured reflections

  • 1350 independent reflections

  • 1220 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.106

  • S = 1.08

  • 1350 reflections

  • 186 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N2i 0.82 2.06 2.877 (3) 174
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.])and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6921 ).


Acknowledgements

The authors thank Professor Daniel Avignant for the X-ray measurements.

References

Ait Ali, M., Karim, A., Castanet, Y., Mortreux, A. & Mentré, O. (2006). Acta Cryst. E62, m3160-m3162.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Gaudo, T., Bleifu, S. M., Müller, A. L., Roth, T., Hoffmann, S., Heinemann, W. F. & Burzlaff, N. (2011). Dalton Trans. 40, 6547-6554.  [PubMed]
Harrad, M. A., Valerga, P., Puerta, M. C., Ali, M. A., El Firdoussi, L. & Karim, A. (2010). Acta Cryst. E66, m281.  [CrossRef] [IUCr Journals]
Jennings, B. H. & Herschbach, G. B. (1965). J. Org. Chem. 30, 3902-3909.  [CrossRef] [ChemPort]
Pastrán, J., Ineichen, E., Agrifoglio, G., Linden, A. & Dorta, R. (2011). Acta Cryst. E67, o188-o189.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spannenberg, A., Fdil, N., El Firdoussi, L. & Karim, A. (2002). Z. Kristallogr. New Cryst. Struct. 217, 549-550.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1314  [ doi:10.1107/S160053681302000X ]

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