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Volume 68 
Part 1 
Page o86  
January 2012  

Received 2 December 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.110
Data-to-parameter ratio = 19.2
Details
Open access

2-{1-[(2-Nitrobenzenesulfonamido)methyl]cyclohexyl}acetic acid

aDepartment of Chemistry, Lahore College for Women University, Lahore 54000, Pakistan, and bDepartment of Physics, Ondokuz Mayis University, TR-55139 Samsun, Turkey
Correspondence e-mail: nosheen.chem.lcwu@gmail.com

In the title compound, C15H20N2O6S, the C-SO2-NH-C torsion angle is 64.54 (14)°. In the molecule, there is a bifurcated N-H...(O,O) hydrogen bond, forming S(7) rings. In the crystal, inversion dimers are formed via O-H...O hydrogen bonds involving the carboxyl group, so forming R22(8) rings. These dimers are further linked via pairs of C-H...O hydrogen bonds, forming a C(6) chain propagating along the c-axis direction.

Related literature

For commercial uses of gabapentin {systematic name: 2-[1-(aminomethyl)cyclohexyl]acetic acid}, see: Taylor et al. (1998[Taylor, C. P., Gee, N. S., Su, T.-Z., Kocsis, J. D., Welty, D. F., Brown, J. P., Dooley, D. J., Boden, P. & Singh, L. (1998). Epilepsy Res. 29, 233-249.]); Cesena & Calcutt (1999[Cesena, R. M. & Calcutt, N. A. (1999). Neurosci. Lett. 262, 101-104.]); Field et al. (2000[Field, M. J., Hughes, J. & Singh, L. (2000). Br. J. Pharmacol. 131, 282-286.]). For the ability of gabapentin to inhibit voltage-dependent Ca2+ channel currents, see: Stefani et al. (1998[Stefani, A., Spadoni, F. & Bernarrdi, G. (1998). Neuropharmacology, 37, 83-91.]); Walker & De Waard (1998[Walker, D. & De Waard, M. (1998). TINS, 21, 148-154.]); Martin et al. (2000[Martin, D. J., Ibbotson, T. & Scott, R. H. (2000). J. Physiol. 528P, C45.]); Sutton et al. (2002[Sutton, K. G., Martin, D. J., Pinnock, R. D., Lee, K. & Scott, R. H. (2002). Br. J. Pharmacol. 135, 257-265.]). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C15H20N2O6S

  • Mr = 356.39

  • Monoclinic, P 21 /c

  • a = 7.7383 (2) Å

  • b = 20.7319 (5) Å

  • c = 11.9460 (3) Å

  • [beta] = 116.869 (1)°

  • V = 1709.59 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 296 K

  • 0.37 × 0.33 × 0.32 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 17069 measured reflections

  • 4247 independent reflections

  • 3202 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.110

  • S = 1.02

  • 4247 reflections

  • 221 parameters

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3 0.790 (19) 2.362 (19) 2.978 (2) 135.6 (18)
N1-H1...O6 0.790 (19) 2.455 (19) 3.050 (2) 133.0 (18)
O5-H5...O6i 0.82 1.85 2.6595 (18) 168
C12-H12...O2ii 0.93 2.50 3.339 (2) 151
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2343 ).


Acknowledgements

The authors are grateful to the Department of Chemistry, GC University Lahore, Pakistan, for providing the diffractometer facility.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cesena, R. M. & Calcutt, N. A. (1999). Neurosci. Lett. 262, 101-104.  [ISI] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Field, M. J., Hughes, J. & Singh, L. (2000). Br. J. Pharmacol. 131, 282-286.  [ISI] [CrossRef] [PubMed] [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]
Martin, D. J., Ibbotson, T. & Scott, R. H. (2000). J. Physiol. 528P, C45.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stefani, A., Spadoni, F. & Bernarrdi, G. (1998). Neuropharmacology, 37, 83-91.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sutton, K. G., Martin, D. J., Pinnock, R. D., Lee, K. & Scott, R. H. (2002). Br. J. Pharmacol. 135, 257-265.  [ISI] [CrossRef] [PubMed] [ChemPort]
Taylor, C. P., Gee, N. S., Su, T.-Z., Kocsis, J. D., Welty, D. F., Brown, J. P., Dooley, D. J., Boden, P. & Singh, L. (1998). Epilepsy Res. 29, 233-249.  [CrossRef] [ChemPort] [PubMed]
Walker, D. & De Waard, M. (1998). TINS, 21, 148-154.  [ChemPort] [PubMed]


Acta Cryst (2012). E68, o86  [ doi:10.1107/S160053681105224X ]

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