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Volume 69 
Part 5 
Pages o752-o753  
May 2013  

Received 16 March 2013
Accepted 9 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 16.9
Details
Open access

2-Methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine (olanzapine) propan-2-ol disolvate

aStrathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland
Correspondence e-mail: alastair.florence@strath.ac.uk

In the title solvate, C17H20N4S·2C3H8O, pairs of olanzapine molecules related by a centre of inversion stack along the a axis, forming columns, which are packed parallel to each other along the b axis, forming a sheet arrangement. The columns within these sheets are hydrogen bonded to each other through the propan-2-ol solvent molecules. The diazepine ring of the olanzapine exists in a puckered conformation with the thiophene and phenyl rings making a dihedral angle of 57.66 (7)° and the piperazine ring adopts a chair conformation with the methyl group in an equatorial position.

Related literature

For literature on olanzapine and related structural studies, see: Fulton & Goa (1997[Fulton, B. & Goa, K. L. (1997). Drugs, 53, 281-298.]); Sanger et al. (2001[Sanger, T. M., Grundy, S. L., Gibson, P. J., Namjoshi, M. A., Greaney, M. G. & Tohen, M. F. (2001). J. Clin. Psychiatry, 62, 273-281.]); Tollefson et al. (1997[Tollefson, G. D., Beasley, C. M., Tran, P. V., Street, J. S., Krueger, J. A., Tamura, R. N., Graffeo, K. A. & Thieme, M. E. (1997). Am. J. Psychiatry, 154, 457-465.]); Reutzel-Edens et al. (2003[Reutzel-Edens, S. M., Bush, J. K., Magee, P. A., Stephenson, G. A. & Byrn, S. R. (2003). Cryst. Growth Des. 3, 897-907.]); Bhardwaj et al. (2013[Bhardwaj, R. M., Price, L. S., Price, S. L., Reutzel-Edens, S. M., Miller, G. J., Oswald, I. D. H., Johnston, B. & Florence, A. J. (2013). Cryst. Growth Des. 3, 1602-1617.]). For details of experimental methods used, see: Florence et al. (2003[Florence, A. J., Baumgartner, B., Weston, C., Shankland, N., Kennedy, A. R., Shankland, K. & David, W. I. F. (2003). J. Pharm. Sci. 92, 1930-1938.]). For details of XPac, see: Gelbrich & Hursthouse (2005[Gelbrich, T. & Hursthouse, M. B. (2005). CrystEngComm, 7, 324-336.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20N4S·2C3H8O

  • Mr = 432.62

  • Triclinic, [P \overline 1]

  • a = 9.9621 (5) Å

  • b = 10.8702 (6) Å

  • c = 12.2298 (7) Å

  • [alpha] = 70.421 (2)°

  • [beta] = 74.560 (2)°

  • [gamma] = 77.296 (2)°

  • V = 1190.24 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 123 K

  • 0.41 × 0.34 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.581, Tmax = 0.745

  • 16365 measured reflections

  • 4880 independent reflections

  • 4073 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.04

  • 4880 reflections

  • 289 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2Si 0.90 (2) 2.04 (2) 2.933 (2) 177 (2)
O1S-H3S...N4ii 0.86 (2) 1.94 (2) 2.778 (2) 167 (2)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: 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.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]) and 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: FJ2624 ).


Acknowledgements

RM thanks the Commonwealth Scholarship Commission for providing a scholarship.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Bhardwaj, R. M., Price, L. S., Price, S. L., Reutzel-Edens, S. M., Miller, G. J., Oswald, I. D. H., Johnston, B. & Florence, A. J. (2013). Cryst. Growth Des. 3, 1602-1617.  [CrossRef]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Florence, A. J., Baumgartner, B., Weston, C., Shankland, N., Kennedy, A. R., Shankland, K. & David, W. I. F. (2003). J. Pharm. Sci. 92, 1930-1938.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Fulton, B. & Goa, K. L. (1997). Drugs, 53, 281-298.  [CrossRef] [ChemPort] [PubMed] [ISI]
Gelbrich, T. & Hursthouse, M. B. (2005). CrystEngComm, 7, 324-336.  [ISI] [CrossRef] [ChemPort]
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]
Reutzel-Edens, S. M., Bush, J. K., Magee, P. A., Stephenson, G. A. & Byrn, S. R. (2003). Cryst. Growth Des. 3, 897-907.  [ChemPort]
Sanger, T. M., Grundy, S. L., Gibson, P. J., Namjoshi, M. A., Greaney, M. G. & Tohen, M. F. (2001). J. Clin. Psychiatry, 62, 273-281.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tollefson, G. D., Beasley, C. M., Tran, P. V., Street, J. S., Krueger, J. A., Tamura, R. N., Graffeo, K. A. & Thieme, M. E. (1997). Am. J. Psychiatry, 154, 457-465.  [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o752-o753   [ doi:10.1107/S1600536813009811 ]

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