[Journal logo]

Volume 69 
Part 2 
Pages o232-o233  
February 2013  

Received 2 December 2012
Accepted 7 January 2013
Online 12 January 2013

[bv2217sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.038
wR = 0.107
Data-to-parameter ratio = 12.9
Details
Open access

Olanzapinium dipicrate

C. N. Kavitha,a Jerry P. Jasinski,b* Amanda C. Keeley,b H. S. Yathirajana and A. S. Dayanandaa

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

The asymmetric unit of the title salt [systematic name: 2-methyl-4-(4-methylpiperazin-4-ium-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepinium bis(2,4,6-trinitrophenolate)], C17H22N4S2+·2C6H2N3O7-, consists of a diprotonated olanzapinium cation and two independent picrate anions. In the cation, the piperazine ring adopts a distorted chair conformation and contains a positively charged N atom with quaternary character and the N atom in the seven-membered 1,5-diazepine ring, which adopts a boat configuration, is also protonated. The dihedral angle between the benzene and thiene rings flanking the diazepine ring is 58.8 (1)°. In one of the picrate anions, a nitro group is disordered over two sets of sites in a 0.748 (5):0.252 (5) ratio, and the benzene ring has a flat envelope conformation with the O- C atom displaced from the mean plane of the other five C atoms [maximum deviation 0.0151 (14) Å] by 0.1449 (14) Å. In the crystal, N-H...O hydrogen bonds and weak intermolecular C-H...S and C-H...O interactions link the components, forming a three-dimensional network.

Related literature

For the use of olanzapine in the management of bipolar disorder, see: Narasimhan et al. (2007[Narasimhan, M., Bruce, T. O. & Masand, P. (2007). Neuropsychiatr. Dis. Treat. 3, 579-587.]) and for toxicity and fatality associated with its overdose, see: Chue & Singer (2003[Chue, P. & Singer, P. (2003). J. Psychiatr. Neurosci. 28, 253-261.]). For related structures, see: Capuano et al. (2003[Capuano, B., Crosby, I. T., Fallon, G. D., Lloyd, E. J., Yuriev, E. & Egan, S. J. (2003). Acta Cryst. E59, o1367-o1369.]); Wawrzycka-Gorczyca et al. (2004a[Wawrzycka-Gorczyca, I., Koziol, A. E., Glice, M. & Cybulski, J. (2004a). Acta Cryst. E60, o66-o68.],b[Wawrzycka-Gorczyca, I., Mazur, L. & Koziol, A. E. (2004b). Acta Cryst. E60, o69-o71.], 2006[Wawrzycka-Gorczyca, I., Borowski, P., Osypiuk-Tomasik, J., Mazur, L. & Koziol, A. E. (2006). J. Mol. Struct. 830, 188-197.]); Ravikumar et al. (2005[Ravikumar, K., Swamy, G. Y. S. K., Sridhar, B. & Roopa, S. (2005). Acta Cryst. E61, o2720-o2723.]); Thakuria & Nangia (2011a[Thakuria, R. & Nangia, A. (2011a). CrystEngComm, 13, 1759-1764.],b[Thakuria, R. & Nangia, A. (2011b). Acta Cryst. C67, o461-o463.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C17H22N4S2+·2C6H2N3O7-

  • Mr = 770.66

  • Orthorhombic, P b c a

  • a = 22.1660 (4) Å

  • b = 12.7349 (2) Å

  • c = 23.3951 (4) Å

  • V = 6604.04 (19) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 1.65 mm-1

  • T = 173 K

  • 0.28 × 0.22 × 0.12 mm
Data collection

  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.702, Tmax = 1.000

  • 44193 measured reflections

  • 6524 independent reflections

  • 5508 reflections with I > 2[sigma](I)

  • Rint = 0.041
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.03

  • 6524 reflections

  • 506 parameters

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1A 0.872 (17) 1.848 (17) 2.7086 (17) 168.5 (16)
N4-H4...O1B 0.926 (19) 1.859 (19) 2.6612 (17) 143.6 (17)
N4-H4...O7B 0.926 (19) 2.449 (19) 3.1714 (19) 135.0 (15)
N1-H1...O5Bi 0.852 (19) 2.40 (2) 3.1395 (18) 145.9 (17)
C5B-H5B...S1ii 0.93 2.87 3.6225 (15) 139
C8-H8...O3Aiii 0.93 2.48 3.349 (2) 156
C12-H12A...O5Aiv 0.97 2.23 3.0970 (19) 149
C17-H17B...O6Aiv 0.96 2.43 3.207 (2) 138
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iv) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2217 ).

Acknowledgements

CNK thanks the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Capuano, B., Crosby, I. T., Fallon, G. D., Lloyd, E. J., Yuriev, E. & Egan, S. J. (2003). Acta Cryst. E59, o1367-o1369.  [CSD] [CrossRef] [details]
Chue, P. & Singer, P. (2003). J. Psychiatr. Neurosci. 28, 253-261.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Narasimhan, M., Bruce, T. O. & Masand, P. (2007). Neuropsychiatr. Dis. Treat. 3, 579-587.  [PubMed] [ChemPort]
Ravikumar, K., Swamy, G. Y. S. K., Sridhar, B. & Roopa, S. (2005). Acta Cryst. E61, o2720-o2723.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Thakuria, R. & Nangia, A. (2011a). CrystEngComm, 13, 1759-1764.  [ISI] [CSD] [CrossRef] [ChemPort]
Thakuria, R. & Nangia, A. (2011b). Acta Cryst. C67, o461-o463.  [CSD] [CrossRef] [details]
Wawrzycka-Gorczyca, I., Borowski, P., Osypiuk-Tomasik, J., Mazur, L. & Koziol, A. E. (2006). J. Mol. Struct. 830, 188-197.
Wawrzycka-Gorczyca, I., Koziol, A. E., Glice, M. & Cybulski, J. (2004a). Acta Cryst. E60, o66-o68.  [CSD] [CrossRef] [details]
Wawrzycka-Gorczyca, I., Mazur, L. & Koziol, A. E. (2004b). Acta Cryst. E60, o69-o71.  [CSD] [CrossRef] [details]

Acta Cryst (2013). E69, o232-o233   [ doi:10.1107/S1600536813000640 ]

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.