[Journal logo]

Volume 69 
Part 7 
Page o1107  
July 2013  

Received 17 April 2013
Accepted 9 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.067
wR = 0.180
Data-to-parameter ratio = 13.6
Details
Open access

O-Benzoylnaltrexone

aDepartment of Pharmacology, Technical Center, Jiangsu Nhwa Pharma Corporation, Zhongshan Road No. 289, Xuzhou 221009, People's Republic of China, and bKey Laboratory of Coal Processing and Efficient Utilization, (Ministry of Education), China University of Mining & Technology, Xuzhou 221116, Jiangsu, People's Republic of China
Correspondence e-mail: lix911@126.com

In the title compound, C27H27NO5 (systematic name: 17-cyclopropylmethyl-14-hydroxy-6-oxo-4,5-epoxymorphinan-6-yl benzoate), which is the benzoate ester of the opioid receptor antagonist naltrexone, the dihedral angle between the two phenyl rings is 77.1 (1)°. In the crystal, a weak aromatic C-H...Ocarboxyl hydrogen bond involving the benzoate groups of adjacent molecules gives rise to a chain extending along the a-axis direction. The known absolute configuration for the molecule was inferred from a previous naltrexone structure.

Related literature

For chemical properties of naltrexone, see: Fernando et al. (2008[Fernando, S.-D., Fernando, L., Francesc, L., Miguel, J. & Catalina, R.-P. (2008). Cryst. Growth Des. 8, 3219-3232.]); Beznischenko et al. (2007[Beznischenko, A. O., Makhankova, V. G., Kokozay, V. N., Zubatyuk, R. I. & Shishkin, O. V. (2007). Inorg. Chim. Acta, 10, 1325-1329.]). For related structures, see: Ledain et al. (1992[Ledain, A. C., Madsen, B. W., Skelton, B. W. & White, A. H. (1992). Aust. J. Chem. 45, 835-840.]); Li et al. (2012[Li, G., Cai, X., Zheng, Z., Zhou, X. & Li, S. (2012). Acta Cryst. E68, o827.]).

[Scheme 1]

Experimental

Crystal data
  • C27H27NO5

  • Mr = 445.50

  • Monoclinic, P 21

  • a = 7.8890 (16) Å

  • b = 8.6620 (17) Å

  • c = 16.629 (3) Å

  • [beta] = 102.24 (3)°

  • V = 1110.5 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (CAD-4 EXPRESS; Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]) Tmin = 0.973, Tmax = 0.991

  • 4421 measured reflections

  • 4083 independent reflections

  • 2611 reflections with I > 2[sigma](I)

  • Rint = 0.030

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.180

  • S = 1.00

  • 4083 reflections

  • 301 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1886 Friedel pairs

  • Flack parameter: 0.04 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C24-H24A...O5i 0.93 2.54 3.453 (7) 168
Symmetry code: (i) x+1, y, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2258 ).


References

Beznischenko, A. O., Makhankova, V. G., Kokozay, V. N., Zubatyuk, R. I. & Shishkin, O. V. (2007). Inorg. Chim. Acta, 10, 1325-1329.  [ChemPort]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Fernando, S.-D., Fernando, L., Francesc, L., Miguel, J. & Catalina, R.-P. (2008). Cryst. Growth Des. 8, 3219-3232.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Ledain, A. C., Madsen, B. W., Skelton, B. W. & White, A. H. (1992). Aust. J. Chem. 45, 835-840.  [CrossRef]
Li, G., Cai, X., Zheng, Z., Zhou, X. & Li, S. (2012). Acta Cryst. E68, o827.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1107  [ doi:10.1107/S1600536813016036 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.