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Volume 69 
Part 1 
Page o2  
January 2013  

Received 19 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.009 Å
R = 0.068
wR = 0.141
Data-to-parameter ratio = 7.3
Details
Open access

Stable polymorph of morphine1

aInstitute of Pharmacy, University of Innsbruck, Innrain 52c, 6020 Innsbruck, Austria
Correspondence e-mail: thomas.gelbrich@uibk.ac.at

In the stable polymorph of the title compound, C17H19NO3 [systematic name: (5[alpha],6[alpha])-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol], the molecular conformation is in agreement with the characteristics of previously reported morphine forms. The molecule displays the typical T-shape and its piperidine ring adopts a slightly distorted chair conformation. Intermolecular O-H...O hydrogen bonds link the molecules into helical chains parallel to the b axis. Intramolecular O-H...O hydrogen bonds are also observed.

Related literature

For related structures, see: Guguta et al. (2008[Guguta, C., Peters, T. P. J. & de Gelder, R. (2008). Cryst. Growth Des. 8, 4150-4158.]); Gylbert (1973[Gylbert, L. (1973). Acta Cryst. B29, 1630-1635.]); Mackay & Hodgkin (1955[Mackay, M. & Hodgkin, D. C. (1955). J. Chem. Soc. 3261-3267.]); Bye (1976[Bye, E. (1976). Acta Chem. Scand. Ser. B, 30, 549-554.]); Wongweichintana et al. (1984[Wongweichintana, C., Holt, E. M. & Purdie, N. (1984). Acta Cryst. C40, 1486-1490.]); Lutz & Spek (1998[Lutz, M. & Spek, A. L. (1998). Acta Cryst. C54, 1477-1479.]); Scheins et al. (2005[Scheins, S., Messerschmidt, M. & Luger, P. (2005). Acta Cryst. B61, 443-448.]); Gelbrich et al. (2012[Gelbrich, T., Braun, D. E. & Griesser, U. J. (2012). Acta Cryst. E68, o3358-o3359.]). For decriptions of morphine polymorphs, see: Kofler (1933[Kofler, L. (1933). Pharm. Monatsh. 14, 220-222.]); Kuhnert-Brandstätter et al. (1975[Kuhnert-Brandstätter, M., Kofler, A. & Heindl, W. (1975). Pharm. Acta Helv. 50, 360-372.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the program XPac, see: Gelbrich & Hursthouse (2005[Gelbrich, T. & Hursthouse, M. B. (2005). CrystEngComm, 7, 324-336.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19NO3

  • Mr = 285.33

  • Orthorhombic, P 21 21 21

  • a = 7.6989 (10) Å

  • b = 12.737 (4) Å

  • c = 13.740 (4) Å

  • V = 1347.4 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.78 mm-1

  • T = 173 K

  • 0.15 × 0.10 × 0.03 mm

Data collection
  • Oxford Diffraction Xcalibur (Ruby, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.]) Tmin = 0.624, Tmax = 1.000

  • 13009 measured reflections

  • 1408 independent reflections

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

  • Rint = 0.118

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.141

  • S = 1.01

  • 1408 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.84 1.96 2.757 (6) 159
O3-H3...O2 0.84 2.17 2.629 (6) 114
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Bruker, 1998[Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA]) and Mercury (Bruno et al., 2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2413 ).


Acknowledgements

We thank Volker Kahlenberg for access to the X-ray instrument used in this study. DEB acknowledges financial support from the Hertha Firnberg Programme of the Austrian Science Fund (FWF, project No. T593-N19).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.  [ISI] [CrossRef] [details]
Bye, E. (1976). Acta Chem. Scand. Ser. B, 30, 549-554.  [CrossRef]
Gelbrich, T., Braun, D. E. & Griesser, U. J. (2012). Acta Cryst. E68, o3358-o3359.  [CSD] [CrossRef] [details]
Gelbrich, T. & Hursthouse, M. B. (2005). CrystEngComm, 7, 324-336.  [ISI] [CrossRef] [ChemPort]
Guguta, C., Peters, T. P. J. & de Gelder, R. (2008). Cryst. Growth Des. 8, 4150-4158.  [CrossRef] [ChemPort]
Gylbert, L. (1973). Acta Cryst. B29, 1630-1635.  [CrossRef] [ChemPort] [details] [ISI]
Kofler, L. (1933). Pharm. Monatsh. 14, 220-222.  [ChemPort]
Kuhnert-Brandstätter, M., Kofler, A. & Heindl, W. (1975). Pharm. Acta Helv. 50, 360-372.  [PubMed] [ISI]
Lutz, M. & Spek, A. L. (1998). Acta Cryst. C54, 1477-1479.  [CSD] [CrossRef] [details]
Mackay, M. & Hodgkin, D. C. (1955). J. Chem. Soc. 3261-3267.
Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, England.
Scheins, S., Messerschmidt, M. & Luger, P. (2005). Acta Cryst. B61, 443-448.  [ISI] [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Wongweichintana, C., Holt, E. M. & Purdie, N. (1984). Acta Cryst. C40, 1486-1490.  [CrossRef] [details]


Acta Cryst (2013). E69, o2  [ doi:10.1107/S1600536812048945 ]

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