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Volume 69 
Part 12 
Pages o1737-o1738  
December 2013  

Received 20 September 2013
Accepted 8 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.163
Data-to-parameter ratio = 18.4
Details
Open access

Venlafaxine besylate monohydrate

aGerencia Materiales, GAEN - CAC - CNEA, Av. Gral. Paz 1499, (1650) San Martín, Buenos Aires, Argentina,bDepartamento Física de la Materia Condensada, Gerencia Investigación y Aplicaciones, GAIyANN - CAC - CNEA, Av. Gral. Paz 1499, (1650) San Martín, Buenos Aires, Argentina, and cEscuela de Ciencia y Tecnología, Campus Miguelete, Edificio Tornavías, UNSAM, Martín de Irigoyen N 3100, (1650) San Martín - Buenos Aires, Argentina
Correspondence e-mail: carolinacorvalan@gmail.com

The title compound {systematic name: [2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]dimethylazanium benzene­sulfonate monohydrate}, C17H28NO2+·C6H5O3S-·H2O, is a besylate salt hydrate of the anti­depressant drug venlafaxine. In the crystal, besylate anions and water mol­ecules self-assemble, forming hydrogen-bonded dimers linked around inversion centers, with graph set R44(6). The crystal packing features a chain of alternate dimers and venlafaxine cations in the b-axis direction with the components linked by O-H...O hydrogen bonds and C-H...O and C-H...[pi] inter­actions. This is the first example of a venlafaxine cation with a closed conformation, as it features an intra­molecular N-H...O inter­action involving the protonated N atom.

Related literature

For background information, see: Venu et al. (2008[Venu, N., Sreekanth, B. R., Ram, T. & Devarakonda, S. (2008). Acta Cryst. C64, o290-o292.]); Tessler & Goldberg (2004[Tessler, L. & Goldberg, I. (2004). Acta Cryst. E60, o1868-o1869.]); Van Eupen et al. (2008[Van Eupen, J. Th. H., Elffrink, W. W. J., Keltjens, R., Bennema, P., de Gelder, R., Smits, J. M. M., van Eck, E. R. H., Kentgens, A. P. M., Deij, M. A., Meekes, H. & Vlieg, E. (2008). Cryst. Growth Des. 8, 71-79.]); Yardley et al. (1990[Yardley, J. P., Husbands, G. E. M., Stack, G., Butch, J., Bicksler, J., Moyer, J. A., Muth, E. A., Andree, T., Fletcher, H. III, James, M. N. G. & Sielecki, A. R. (1990). J. Med. Chem. 33, 2899-2905.]); Banjeree et al. (2005[Banjeree, R., Bhatt, P. M., Ravindra, N. V. & Desiraju, G. R. (2005). Cryst. Growth Des. 5, 2299-2309.]); Vega et al. (2000[Vega, D., Fernández, D. & Echeverría, G. (2000). Acta Cryst. C56, 1009-1010.]); Sivalakshmidevi et al. (2002[Sivalakshmidevi, A., Vyas, K., Mahender Rao, S. & Om Reddy, G. (2002). Acta Cryst. E58, o1072-o1074.]); Roy et al. (2007[Roy, S., Bhatt, P. M., Nangia, A. & Kruger, G. J. (2007). Cryst. Growth Des. 7, 476-480.]). For ring-puckering calculations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 35, 1555-1573.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C17H28NO2+·C6H5O3S-·H2O

  • Mr = 453.58

  • Triclinic, [P \overline 1]

  • a = 10.1163 (5) Å

  • b = 10.2176 (4) Å

  • c = 13.8162 (6) Å

  • [alpha] = 72.074 (4)°

  • [beta] = 70.108 (4)°

  • [gamma] = 63.889 (5)°

  • V = 1184.53 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 293 K

  • 0.70 × 0.30 × 0.10 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.842, Tmax = 1.000

  • 10063 measured reflections

  • 5366 independent reflections

  • 3072 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.163

  • S = 1.02

  • 5366 reflections

  • 292 parameters

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

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O2-H2A...O1W 0.81 (3) 1.87 (3) 2.673 (3) 173 (3)
O1W-H1WB...O3B 0.83 (3) 1.92 (3) 2.711 (4) 159 (3)
O1W-H1WA...O2Bi 0.88 (3) 1.91 (3) 2.785 (4) 175 (3)
N1-H1...O2 0.78 (3) 2.05 (3) 2.719 (2) 143 (3)
C15-H15C...O2B 0.96 2.68 3.468 (4) 140
C16-H16A...O1Bii 0.96 2.44 3.395 (4) 172
C2-H2...Cg1 0.93 3.17 3.928 140
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2130 ).


Acknowledgements

We are grateful to Gador S.A. for providing the raw material. We also acknowledge PIP-11220090100889 and ANPCyT (project No. PME 2006-01113) for the purchase of the Oxford Gemini CCD diffractometer.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Banjeree, R., Bhatt, P. M., Ravindra, N. V. & Desiraju, G. R. (2005). Cryst. Growth Des. 5, 2299-2309.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 35, 1555-1573.  [CrossRef] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Roy, S., Bhatt, P. M., Nangia, A. & Kruger, G. J. (2007). Cryst. Growth Des. 7, 476-480.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sivalakshmidevi, A., Vyas, K., Mahender Rao, S. & Om Reddy, G. (2002). Acta Cryst. E58, o1072-o1074.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tessler, L. & Goldberg, I. (2004). Acta Cryst. E60, o1868-o1869.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Van Eupen, J. Th. H., Elffrink, W. W. J., Keltjens, R., Bennema, P., de Gelder, R., Smits, J. M. M., van Eck, E. R. H., Kentgens, A. P. M., Deij, M. A., Meekes, H. & Vlieg, E. (2008). Cryst. Growth Des. 8, 71-79.  [CSD] [CrossRef] [ChemPort]
Vega, D., Fernández, D. & Echeverría, G. (2000). Acta Cryst. C56, 1009-1010.  [CSD] [CrossRef] [IUCr Journals]
Venu, N., Sreekanth, B. R., Ram, T. & Devarakonda, S. (2008). Acta Cryst. C64, o290-o292.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Yardley, J. P., Husbands, G. E. M., Stack, G., Butch, J., Bicksler, J., Moyer, J. A., Muth, E. A., Andree, T., Fletcher, H. III, James, M. N. G. & Sielecki, A. R. (1990). J. Med. Chem. 33, 2899-2905.  [CSD] [CrossRef] [PubMed] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1737-o1738   [ doi:10.1107/S1600536813027542 ]

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