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Volume 68 
Part 12 
Pages o3358-o3359  
December 2012  

Received 15 October 2012
Accepted 9 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.069
Data-to-parameter ratio = 13.0
Details
Open access

Morphine hydrochloride anhydrate1

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

In the title molecular salt [systematic name: (5[alpha],6[alpha])-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol hydrochloride], C17H20NO3+·Cl-, the conformation of the morphinium ion is in agreement with the characteristics of the previously reported morphine forms [for example, Gylbert (1973[Gylbert, L. (1973). Acta Cryst. B29, 1630-1635.]). Acta Cryst. B29, 1630-1635]. In the crystal, the cations and chloride anions are linked into a helical chain propagating parallel to the b-axis direction by N-H...Cl and O-H...Cl hydrogen bonds. The title salt and the morphine monohydrate [Bye (1976[Bye, E. (1976). Acta Chem. Scand. Ser. B, 30, 549-554.]) Acta Chem. Scand. 30, 549-554] display very similar one-dimensional packing modes of their morphine components.

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. pp. 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.]). For hysdrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). 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.]) and for the corresponding XPac dissimilarity index, see: Gelbrich et al. (2012[Gelbrich, T., Threlfall, T. L. & Hursthouse, M. B. (2012). CrystEngComm, 14, 5454-5464.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20NO3+·Cl-

  • Mr = 321.79

  • Orthorhombic, P 21 21 21

  • a = 7.3504 (2) Å

  • b = 12.8524 (5) Å

  • c = 16.0372 (5) Å

  • V = 1515.04 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 173 K

  • 0.20 × 0.20 × 0.20 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, England.]) Tmin = 0.982, Tmax = 1.000

  • 7406 measured reflections

  • 2971 independent reflections

  • 2803 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

  • wR(F2) = 0.069

  • S = 1.04

  • 2971 reflections

  • 229 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1245 Friedel pairs

  • Flack parameter: 0.02 (5)

Table 1
Hydrogen-bond and short-contact geometry (Å, °)

Cg1 is the centroid of the C1-C4/C12/C11 benzene ring.

D-H...A D-H H...A D...A D-H...A
O1-H1O...Cl1 0.82 (1) 2.35 (1) 3.1585 (14) 173 (2)
O3-H3O...Cl1 0.83 (1) 2.32 (1) 3.1416 (13) 168 (2)
N1-H1N...Cl1i 0.93 (1) 2.15 (1) 3.0626 (15) 169 (2)
C17-H17C...O3ii 0.98 2.38 3.278 (2) 153
C14-H14...O2i 1.00 2.60 3.2149 (19) 120
C2-H2...Cg1iii 0.95 2.71 3.638 (2) 165
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: CrysAlis PRO (Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXL97 (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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: LX2271 ).


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 T593-N19).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bye, E. (1976). Acta Chem. Scand. Ser. B, 30, 549-554.  [CrossRef]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gelbrich, T. & Hursthouse, M. B. (2005). CrystEngComm, 7, 324-336.  [ISI] [CrossRef] [ChemPort]
Gelbrich, T., Threlfall, T. L. & Hursthouse, M. B. (2012). CrystEngComm, 14, 5454-5464.  [ISI] [CSD] [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]
Lutz, M. & Spek, A. L. (1998). Acta Cryst. C54, 1477-1479.  [CSD] [CrossRef] [details]
Mackay, M. & Hodgkin, D. C. (1955). J. Chem. Soc. pp. 3261-3267.  [CrossRef]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, 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 (2012). E68, o3358-o3359   [ doi:10.1107/S1600536812046405 ]

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