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Volume 69 
Part 10 
Pages o1556-o1557  
October 2013  

Received 10 September 2013
Accepted 12 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.057
wR = 0.158
Data-to-parameter ratio = 24.7
Details
Open access

Desvenlafaxinium chloranilate ethyl acetate solvate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and dMaterials Science Center, University of Mysore, NCHS Building, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

In the cation of the title compound, C16H26NO2+·C6HCl2O4-·C4H8O2, the 1-hydroxy-cyclohexyl ring adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the 1-hydroxycyclohexyl and 4-hydroxyphenyl rings is 84.0 (8)°. In the anion, the hydroxyl H atom is twisted slightly out of the ring plane with a C-C-O-H torsion angle of -171.9°. Disorder was modeled for the methyl group of the acetate group in the solvate with an occupancy ratio of 0.583 (15): 0.417 (15). In the crystal, O-H...O hydrogen bonds are observed between cations and between cations and anions, while bifuricated N-H...(O,O) cation-anion hydrogen bonds are also present, forming chains along [010] and [100]. In addition weak cation-anion and cation-solvate C-H...O interactions occur.

Related literature

For the pharmacological importance of Desvenlafaxine {systematic name: 4-[2-dimethylamino-1-(1-hydroxycyclohexyl)ethyl]phenol}, see: Deecher et al. (2006[Deecher, D. C., Beyer, C. E., Johnston, G., Bray, J., Shah, S., Abou-Gharbia, M. & Andree, T. H. (2006). J. Pharmacol. Exp. Ther. 318, 657-665.]). For related structures, see: Dayananda et al. (2012[Dayananda, A. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o1037-o1038.]); Duggirala et al. (2009[Duggirala, N. K., Kanniah, S. L., Muppidi, V. K., Thaimattam, R. & Devarakonda, S. (2009). CrystEngComm, 11, 989-992.]); Hadfield et al. (2004[Hadfield, A. F., Shah, S. M., Winkley, M. W., Sutherland, K. W., Provost, J. A., Park, A., Shipplett, R. A., Russel, B. W. & Weber, B. T. (2004). US Patent No. 6 673 838 B2.]); Mungkornasawakul et al. (2009[Mungkornasawakul, P., Pyne, S. G., Ung, A. T., Jatisatienr, A. & Willis, A. C. (2009). Acta Cryst. E65, o1878-o1879.]); Sivalakshmidevi et al. (2002[Sivalakshmidevi, A., Vyas, K., Mahender Rao, S. & Om Reddy, G. (2002). Acta Cryst. E58, o1072-o1074.]); Sun et al. (2006[Sun, F.-X., Yu, Y.-F., Guo, X.-N. & Guo, J.-Y. (2006). Acta Cryst. E62, o83-o84.]); Tessler & Goldberg (2004[Tessler, L. & Goldberg, I. (2004). Acta Cryst. E60, o1868-o1869.]); Vega et al. (2000[Vega, D., Fernández, D. & Echeverría, G. (2000). Acta Cryst. C56, 1009-1010.]); Venu et al. (2008[Venu, N., Sreekanth, B. R., Ram, T. & Devarakonda, S. (2008). Acta Cryst. C64, o290-o292.]); Zhang et al. (2006[Zhang, G.-Y., Wang, X.-B., Zhao, J.-Y., Wang, W.-H. & Yang, X.-F. (2006). Acta Cryst. E62, o2239-o2241.]). 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
  • C16H26NO2+·C6HCl2O4-·C4H8O2

  • Mr = 560.45

  • Monoclinic, P n

  • a = 11.1738 (2) Å

  • b = 9.39846 (16) Å

  • c = 13.6046 (2) Å

  • [beta] = 105.109 (2)°

  • V = 1379.33 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 123 K

  • 0.44 × 0.29 × 0.12 mm

Data collection
  • Agilent Xcalibur, Ruby, 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 = 0.991, Tmax = 1.000

  • 16094 measured reflections

  • 8667 independent reflections

  • 7926 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.158

  • S = 1.05

  • 8667 reflections

  • 351 parameters

  • 16 restraints

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

  • [Delta][rho]max = 1.16 e Å-3

  • [Delta][rho]min = -0.75 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3959 Friedel pairs

  • Absolute structure parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.85 2.669 (2) 166
O2-H2...O4A 0.84 1.89 2.694 (3) 160
N1-H1N...O4A 0.89 (3) 1.95 (3) 2.775 (3) 153 (3)
N1-H1N...O3A 0.89 (3) 2.43 (3) 3.099 (3) 132 (2)
O2A-H2A1...O1ii 0.84 2.03 2.768 (3) 147
C3-H3A...O1Aiii 0.95 2.59 3.371 (3) 140
C9-H9B...O1S 0.98 2.29 3.224 (4) 159
Symmetry codes: (i) x, y+1, z; (ii) x+1, y-1, z; (iii) x-1, y+1, z.

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: HG5346 ).


Acknowledgements

MK thanks the UOM for research facilities and is also grateful to CPEPA, UGC, for the award of a JRF. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) 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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dayananda, A. S., Butcher, R. J., Akkurt, M., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o1037-o1038.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Deecher, D. C., Beyer, C. E., Johnston, G., Bray, J., Shah, S., Abou-Gharbia, M. & Andree, T. H. (2006). J. Pharmacol. Exp. Ther. 318, 657-665.  [CrossRef] [PubMed] [ChemPort]
Duggirala, N. K., Kanniah, S. L., Muppidi, V. K., Thaimattam, R. & Devarakonda, S. (2009). CrystEngComm, 11, 989-992.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Hadfield, A. F., Shah, S. M., Winkley, M. W., Sutherland, K. W., Provost, J. A., Park, A., Shipplett, R. A., Russel, B. W. & Weber, B. T. (2004). US Patent No. 6 673 838 B2.
Mungkornasawakul, P., Pyne, S. G., Ung, A. T., Jatisatienr, A. & Willis, A. C. (2009). Acta Cryst. E65, o1878-o1879.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Sun, F.-X., Yu, Y.-F., Guo, X.-N. & Guo, J.-Y. (2006). Acta Cryst. E62, o83-o84.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Tessler, L. & Goldberg, I. (2004). Acta Cryst. E60, o1868-o1869.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Zhang, G.-Y., Wang, X.-B., Zhao, J.-Y., Wang, W.-H. & Yang, X.-F. (2006). Acta Cryst. E62, o2239-o2241.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1556-o1557   [ doi:10.1107/S1600536813025312 ]

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