2-{1-[(2-Nitro-benzene-sulfonamido)-meth-yl]cyclo-hexyl}acetic acid.

In the title compound, C(15)H(20)N(2)O(6)S, the C-SO(2)-NH-C torsion angle is 64.54 (14)°. In the mol-ecule, 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 R(2) (2)(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 ▶); 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 = 356.39

Monoclinic,

a = 7.7383 (2) Å

b = 20.7319 (5) Å

c = 11.9460 (3) Å

β = 116.869 (1)°

V = 1709.59 (7) Å3

Z = 4

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.02

4247 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.32 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105224X/su2343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105224X/su2343Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105224X/su2343Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H20N2O6S	F(000) = 752
Mr = 356.39	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5311 reflections
a = 7.7383 (2) Å	θ = 2.9–27.2°
b = 20.7319 (5) Å	µ = 0.22 mm−1
c = 11.9460 (3) Å	T = 296 K
β = 116.869 (1)°	Block, colourless
V = 1709.59 (7) Å3	0.37 × 0.33 × 0.32 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 28.3°, θmin = 2.0°
phi and ω scans	h = −10→10
17069 measured reflections	k = −27→27
4247 independent reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.4452P] where P = (Fo2 + 2Fc2)/3
4247 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.2548 (2)	0.54510 (7)	0.24581 (13)	0.0348 (3)
C2	0.1197 (2)	0.59198 (8)	0.14519 (15)	0.0438 (4)
H2A	0.1787	0.6344	0.1619	0.053*
H2B	0.1059	0.5781	0.0640	0.053*
C3	−0.0799 (3)	0.59682 (9)	0.13939 (18)	0.0553 (4)
H3A	−0.1568	0.6283	0.0765	0.066*
H3B	−0.1449	0.5554	0.1153	0.066*
C4	−0.0631 (3)	0.61664 (10)	0.2658 (2)	0.0656 (5)
H4A	−0.0060	0.6593	0.2871	0.079*
H4B	−0.1912	0.6185	0.2615	0.079*
C5	0.0607 (3)	0.56932 (10)	0.36644 (19)	0.0638 (5)
H5A	−0.0033	0.5277	0.3493	0.077*
H5B	0.0743	0.5841	0.4471	0.077*
C6	0.2613 (3)	0.56180 (9)	0.37290 (15)	0.0498 (4)
H6A	0.3309	0.5281	0.4327	0.060*
H6B	0.3327	0.6017	0.4036	0.060*
C7	0.4633 (2)	0.55220 (8)	0.26081 (15)	0.0441 (4)
H7A	0.5016	0.5971	0.2766	0.053*
H7B	0.5509	0.5275	0.3333	0.053*
C8	0.4837 (2)	0.52997 (8)	0.14850 (17)	0.0453 (4)
C9	0.1812 (2)	0.47606 (7)	0.20560 (14)	0.0371 (3)
H9A	0.0581	0.4708	0.2075	0.045*
H9B	0.1595	0.4694	0.1199	0.045*
C10	0.0958 (2)	0.31795 (7)	0.19092 (14)	0.0377 (3)
C11	0.1750 (2)	0.27787 (7)	0.13323 (14)	0.0408 (3)
C12	0.0613 (3)	0.23949 (8)	0.03334 (17)	0.0548 (4)
H12	0.1174	0.2125	−0.0034	0.066*
C13	−0.1371 (3)	0.24136 (10)	−0.01188 (19)	0.0648 (5)
H13	−0.2155	0.2159	−0.0802	0.078*
C14	−0.2189 (3)	0.28022 (10)	0.0429 (2)	0.0632 (5)
H14	−0.3528	0.2813	0.0116	0.076*
C15	−0.1039 (2)	0.31806 (8)	0.14452 (18)	0.0510 (4)
H15	−0.1610	0.3439	0.1823	0.061*
N1	0.3172 (2)	0.42711 (6)	0.28645 (14)	0.0441 (3)
H1	0.398 (3)	0.4174 (9)	0.2660 (18)	0.054 (6)*
N2	0.3849 (2)	0.27452 (7)	0.17499 (14)	0.0516 (4)
O1	0.4004 (2)	0.32564 (6)	0.40392 (11)	0.0645 (4)
O2	0.1074 (2)	0.38599 (6)	0.37366 (13)	0.0643 (4)
O3	0.47073 (19)	0.32459 (7)	0.18100 (16)	0.0724 (4)
O4	0.4618 (2)	0.22220 (7)	0.19748 (17)	0.0839 (5)
O5	0.4434 (2)	0.56977 (6)	0.05920 (13)	0.0641 (4)
H5	0.4596	0.5525	0.0030	0.096*
O6	0.5377 (2)	0.47314 (6)	0.14477 (13)	0.0626 (4)
S1	0.23737 (6)	0.364280 (19)	0.32720 (4)	0.04464 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0359 (7)	0.0320 (7)	0.0359 (7)	−0.0062 (6)	0.0158 (6)	−0.0050 (6)
C2	0.0451 (9)	0.0381 (8)	0.0469 (9)	−0.0023 (7)	0.0198 (7)	0.0030 (7)
C3	0.0440 (9)	0.0509 (10)	0.0682 (12)	0.0051 (8)	0.0230 (9)	0.0021 (9)
C4	0.0558 (11)	0.0621 (12)	0.0900 (15)	−0.0012 (9)	0.0428 (11)	−0.0182 (11)
C5	0.0784 (13)	0.0681 (13)	0.0635 (12)	−0.0116 (11)	0.0485 (11)	−0.0197 (10)
C6	0.0591 (10)	0.0487 (9)	0.0400 (8)	−0.0074 (8)	0.0210 (8)	−0.0110 (7)
C7	0.0372 (8)	0.0401 (8)	0.0523 (9)	−0.0092 (6)	0.0177 (7)	−0.0065 (7)
C8	0.0384 (8)	0.0411 (9)	0.0626 (10)	−0.0053 (7)	0.0283 (8)	0.0014 (7)
C9	0.0385 (7)	0.0343 (7)	0.0366 (7)	−0.0066 (6)	0.0152 (6)	−0.0046 (6)
C10	0.0450 (8)	0.0285 (7)	0.0408 (8)	−0.0020 (6)	0.0206 (7)	0.0038 (6)
C11	0.0466 (8)	0.0328 (7)	0.0427 (8)	0.0001 (6)	0.0200 (7)	0.0026 (6)
C12	0.0744 (12)	0.0411 (9)	0.0476 (9)	−0.0029 (8)	0.0265 (9)	−0.0061 (7)
C13	0.0679 (13)	0.0529 (11)	0.0524 (11)	−0.0158 (10)	0.0084 (10)	−0.0034 (9)
C14	0.0453 (10)	0.0577 (12)	0.0723 (13)	−0.0093 (9)	0.0140 (9)	0.0066 (10)
C15	0.0471 (9)	0.0443 (9)	0.0654 (11)	−0.0011 (7)	0.0287 (8)	0.0048 (8)
N1	0.0445 (8)	0.0330 (7)	0.0547 (8)	−0.0023 (6)	0.0223 (7)	0.0002 (6)
N2	0.0531 (8)	0.0444 (8)	0.0598 (9)	0.0074 (7)	0.0277 (7)	−0.0005 (7)
O1	0.0750 (9)	0.0464 (7)	0.0474 (7)	0.0032 (6)	0.0059 (6)	0.0072 (6)
O2	0.1011 (11)	0.0500 (7)	0.0670 (8)	−0.0077 (7)	0.0603 (8)	−0.0054 (6)
O3	0.0548 (8)	0.0564 (8)	0.1159 (13)	−0.0022 (6)	0.0474 (8)	−0.0012 (8)
O4	0.0726 (10)	0.0507 (8)	0.1188 (14)	0.0237 (7)	0.0347 (9)	0.0021 (8)
O5	0.0783 (9)	0.0592 (8)	0.0755 (9)	0.0146 (7)	0.0530 (8)	0.0136 (7)
O6	0.0811 (9)	0.0444 (7)	0.0816 (9)	0.0067 (6)	0.0537 (8)	0.0045 (6)
S1	0.0601 (3)	0.0345 (2)	0.0397 (2)	−0.00341 (17)	0.02283 (19)	0.00003 (15)

C1—C2	1.532 (2)	C9—N1	1.467 (2)
C1—C9	1.5350 (19)	C9—H9A	0.9700
C1—C6	1.536 (2)	C9—H9B	0.9700
C1—C7	1.548 (2)	C10—C15	1.386 (2)
C2—C3	1.518 (2)	C10—C11	1.387 (2)
C2—H2A	0.9700	C10—S1	1.7779 (15)
C2—H2B	0.9700	C11—C12	1.372 (2)
C3—C4	1.513 (3)	C11—N2	1.470 (2)
C3—H3A	0.9700	C12—C13	1.379 (3)
C3—H3B	0.9700	C12—H12	0.9300
C4—C5	1.512 (3)	C13—C14	1.360 (3)
C4—H4A	0.9700	C13—H13	0.9300
C4—H4B	0.9700	C14—C15	1.380 (3)
C5—C6	1.527 (3)	C14—H14	0.9300
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	N1—S1	1.6084 (14)
C6—H6A	0.9700	N1—H1	0.790 (19)
C6—H6B	0.9700	N2—O4	1.2077 (19)
C7—C8	1.493 (2)	N2—O3	1.2167 (19)
C7—H7A	0.9700	O1—S1	1.4244 (13)
C7—H7B	0.9700	O2—S1	1.4240 (13)
C8—O6	1.258 (2)	O5—H5	0.8200
C8—O5	1.271 (2)
C2—C1—C9	108.72 (12)	H7A—C7—H7B	107.7
C2—C1—C6	109.79 (13)	O6—C8—O5	122.54 (16)
C9—C1—C6	111.18 (12)	O6—C8—C7	119.54 (15)
C2—C1—C7	109.67 (12)	O5—C8—C7	117.92 (15)
C9—C1—C7	110.16 (12)	N1—C9—C1	112.64 (12)
C6—C1—C7	107.29 (12)	N1—C9—H9A	109.1
C3—C2—C1	113.41 (13)	C1—C9—H9A	109.1
C3—C2—H2A	108.9	N1—C9—H9B	109.1
C1—C2—H2A	108.9	C1—C9—H9B	109.1
C3—C2—H2B	108.9	H9A—C9—H9B	107.8
C1—C2—H2B	108.9	C15—C10—C11	117.76 (15)
H2A—C2—H2B	107.7	C15—C10—S1	118.65 (13)
C4—C3—C2	110.23 (15)	C11—C10—S1	123.43 (12)
C4—C3—H3A	109.6	C12—C11—C10	121.73 (16)
C2—C3—H3A	109.6	C12—C11—N2	116.35 (15)
C4—C3—H3B	109.6	C10—C11—N2	121.92 (14)
C2—C3—H3B	109.6	C11—C12—C13	119.16 (18)
H3A—C3—H3B	108.1	C11—C12—H12	120.4
C5—C4—C3	110.83 (15)	C13—C12—H12	120.4
C5—C4—H4A	109.5	C14—C13—C12	120.38 (18)
C3—C4—H4A	109.5	C14—C13—H13	119.8
C5—C4—H4B	109.5	C12—C13—H13	119.8
C3—C4—H4B	109.5	C13—C14—C15	120.32 (18)
H4A—C4—H4B	108.1	C13—C14—H14	119.8
C4—C5—C6	111.75 (16)	C15—C14—H14	119.8
C4—C5—H5A	109.3	C14—C15—C10	120.63 (17)
C6—C5—H5A	109.3	C14—C15—H15	119.7
C4—C5—H5B	109.3	C10—C15—H15	119.7
C6—C5—H5B	109.3	C9—N1—S1	120.04 (11)
H5A—C5—H5B	107.9	C9—N1—H1	113.8 (14)
C5—C6—C1	113.24 (14)	S1—N1—H1	110.6 (14)
C5—C6—H6A	108.9	O4—N2—O3	123.53 (16)
C1—C6—H6A	108.9	O4—N2—C11	118.41 (15)
C5—C6—H6B	108.9	O3—N2—C11	118.01 (14)
C1—C6—H6B	108.9	C8—O5—H5	109.5
H6A—C6—H6B	107.7	O2—S1—O1	120.24 (9)
C8—C7—C1	113.23 (12)	O2—S1—N1	107.30 (8)
C8—C7—H7A	108.9	O1—S1—N1	107.49 (8)
C1—C7—H7A	108.9	O2—S1—C10	106.03 (8)
C8—C7—H7B	108.9	O1—S1—C10	106.58 (7)
C1—C7—H7B	108.9	N1—S1—C10	108.81 (7)
C9—C1—C2—C3	69.39 (17)	C10—C11—C12—C13	0.8 (3)
C6—C1—C2—C3	−52.45 (18)	N2—C11—C12—C13	−178.76 (16)
C7—C1—C2—C3	−170.10 (13)	C11—C12—C13—C14	−0.8 (3)
C1—C2—C3—C4	57.0 (2)	C12—C13—C14—C15	−0.2 (3)
C2—C3—C4—C5	−57.7 (2)	C13—C14—C15—C10	1.2 (3)
C3—C4—C5—C6	56.3 (2)	C11—C10—C15—C14	−1.1 (2)
C4—C5—C6—C1	−53.1 (2)	S1—C10—C15—C14	−176.65 (14)
C2—C1—C6—C5	50.00 (18)	C1—C9—N1—S1	139.40 (12)
C9—C1—C6—C5	−70.36 (18)	C12—C11—N2—O4	−52.4 (2)
C7—C1—C6—C5	169.12 (15)	C10—C11—N2—O4	128.05 (18)
C2—C1—C7—C8	−67.57 (17)	C12—C11—N2—O3	125.20 (18)
C9—C1—C7—C8	52.07 (17)	C10—C11—N2—O3	−54.3 (2)
C6—C1—C7—C8	173.23 (14)	C9—N1—S1—O2	−49.77 (14)
C1—C7—C8—O6	−94.18 (18)	C9—N1—S1—O1	179.59 (12)
C1—C7—C8—O5	85.21 (18)	C9—N1—S1—C10	64.54 (14)
C2—C1—C9—N1	171.39 (13)	C15—C10—S1—O2	8.75 (15)
C6—C1—C9—N1	−67.63 (17)	C11—C10—S1—O2	−166.48 (13)
C7—C1—C9—N1	51.19 (17)	C15—C10—S1—O1	137.98 (13)
C15—C10—C11—C12	0.2 (2)	C11—C10—S1—O1	−37.26 (15)
S1—C10—C11—C12	175.44 (13)	C15—C10—S1—N1	−106.38 (13)
C15—C10—C11—N2	179.68 (14)	C11—C10—S1—N1	78.38 (14)
S1—C10—C11—N2	−5.0 (2)

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

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) ; (ii) .