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

Kanwal, N.; Akbar Hussain, E.; Şahin, O.; Büyükgüngör, O.

doi:10.1107/S160053681105224X

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 (C-C) = 0.003 Å
R = 0.040
wR = 0.110
Data-to-parameter ratio = 19.2
Details

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

Nosheen Kanwal,^a ^* Erum Akbar Hussain,^a Onur Sahin ^b and Orhan Büyükgüngör ^b

^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-HO hydrogen bonds involving the carboxyl group, so forming R₂²(8) rings. These dimers are further linked via pairs of C-HO 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); Cesena & Calcutt (1999); Field et al. (2000). For the ability of gabapentin to inhibit voltage-dependent Ca²⁺ channel currents, see: Stefani et al. (1998); Walker & De Waard (1998); Martin et al. (2000); Sutton et al. (2002). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₅H₂₀N₂O₆S
M_r = 356.39
Monoclinic, P 2₁ /c
a = 7.7383 (2) Å
b = 20.7319 (5) Å
c = 11.9460 (3) Å
= 116.869 (1)°
V = 1709.59 (7) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.022

Refinement

R[F² > 2(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
_max = 0.29 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3	0.790 (19)	2.362 (19)	2.978 (2)	135.6 (18)
N1-H1O6	0.790 (19)	2.455 (19)	3.050 (2)	133.0 (18)
O5-H5O6ⁱ	0.82	1.85	2.6595 (18)	168
C12-H12O2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

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organic compounds