4-Chloro-N-cyclo-hexyl-benzene-sulfonamide.

The title compound, C(12)H(16)ClNO(2)S, adopts an L-shaped conformation, with the central C-S-N-C torsion angle being -78.0 (2)°. The cyclo-hexyl ring adopts a chair conformation. In the crystal, adjacent mol-ecules are connected by pairs of N-H⋯O hydrogen bonds around an inversion centre, forming cyclic dimers [graph set R(2) (2)(8)].

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2011 ▶); Khan et al. (2010 ▶); John et al. (2010 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H16ClNO2S

M = 273.78

Monoclinic,

a = 11.1226 (5) Å

b = 6.2490 (2) Å

c = 19.8635 (9) Å

β = 96.505 (2)°

V = 1371.73 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.29 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

12714 measured reflections

3365 independent reflections

2075 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.150

S = 1.03

3365 reflections

157 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001870/hg5164sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001870/hg5164Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001870/hg5164Isup3.cml

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

C12H16ClNO2S	F(000) = 576
Mr = 273.78	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3062 reflections
a = 11.1226 (5) Å	θ = 2.6–21.6°
b = 6.2490 (2) Å	µ = 0.42 mm−1
c = 19.8635 (9) Å	T = 296 K
β = 96.505 (2)°	Needle, light brown
V = 1371.73 (10) Å3	0.29 × 0.15 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	2075 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.030
graphite	θmax = 28.3°, θmin = 3.4°
φ and ω scans	h = −14→14
12714 measured reflections	k = −6→8
3365 independent reflections	l = −26→26

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.526P] where P = (Fo2 + 2Fc2)/3
3365 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.97047 (9)	0.63719 (19)	0.09885 (6)	0.1159 (5)
S1	0.67445 (5)	0.02579 (10)	0.26455 (3)	0.0538 (2)
O1	0.57744 (18)	−0.0412 (3)	0.21563 (11)	0.0788 (8)
O2	0.75531 (17)	−0.1301 (3)	0.29647 (11)	0.0710 (7)
N1	0.61305 (18)	0.1518 (3)	0.32146 (11)	0.0527 (7)
C1	0.7127 (2)	0.3981 (4)	0.19816 (13)	0.0581 (9)
C2	0.7777 (3)	0.5312 (4)	0.16141 (14)	0.0650 (9)
C3	0.8901 (3)	0.4698 (5)	0.14686 (14)	0.0654 (10)
C4	0.9396 (2)	0.2788 (5)	0.16961 (16)	0.0733 (11)
C5	0.8750 (2)	0.1454 (4)	0.20712 (14)	0.0606 (9)
C6	0.7611 (2)	0.2037 (4)	0.22098 (12)	0.0465 (7)
C7	0.6789 (2)	0.2145 (4)	0.38711 (12)	0.0541 (8)
C8	0.7329 (3)	0.4325 (5)	0.38666 (16)	0.0829 (11)
C9	0.7924 (4)	0.4979 (7)	0.45609 (18)	0.1069 (17)
C10	0.7084 (4)	0.4802 (9)	0.5084 (2)	0.117 (2)
C11	0.6528 (5)	0.2674 (10)	0.50951 (18)	0.135 (2)
C12	0.5920 (4)	0.1970 (7)	0.44002 (17)	0.1033 (16)
H1	0.63600	0.43810	0.20780	0.0700*
H1N	0.555 (3)	0.234 (6)	0.3060 (19)	0.1390*
H2	0.74580	0.66260	0.14640	0.0780*
H4	1.01630	0.23970	0.15970	0.0880*
H5	0.90830	0.01600	0.22310	0.0730*
H7	0.74450	0.11150	0.39850	0.0650*
H8A	0.67010	0.53500	0.37150	0.0990*
H8B	0.79270	0.43550	0.35470	0.0990*
H9A	0.86230	0.40740	0.46850	0.1280*
H9B	0.82060	0.64450	0.45420	0.1280*
H10A	0.75200	0.51000	0.55240	0.1410*
H10B	0.64520	0.58700	0.49970	0.1410*
H11A	0.59300	0.26840	0.54140	0.1620*
H11B	0.71460	0.16380	0.52540	0.1620*
H12A	0.56470	0.05020	0.44260	0.1240*
H12B	0.52180	0.28630	0.42710	0.1240*

	U11	U22	U33	U12	U13	U23
Cl1	0.0867 (7)	0.1367 (9)	0.1293 (9)	−0.0197 (6)	0.0339 (6)	0.0505 (7)
S1	0.0456 (4)	0.0438 (3)	0.0725 (4)	−0.0069 (3)	0.0087 (3)	−0.0065 (3)
O1	0.0634 (12)	0.0815 (13)	0.0904 (14)	−0.0310 (10)	0.0034 (11)	−0.0211 (11)
O2	0.0691 (12)	0.0436 (9)	0.1030 (15)	0.0083 (9)	0.0210 (11)	0.0082 (9)
N1	0.0393 (11)	0.0562 (12)	0.0629 (13)	0.0041 (9)	0.0071 (10)	0.0035 (10)
C1	0.0540 (15)	0.0589 (15)	0.0637 (16)	0.0058 (13)	0.0169 (13)	0.0006 (12)
C2	0.0704 (18)	0.0594 (15)	0.0664 (16)	0.0034 (14)	0.0132 (15)	0.0056 (13)
C3	0.0553 (16)	0.0765 (18)	0.0646 (16)	−0.0132 (15)	0.0076 (13)	0.0050 (14)
C4	0.0398 (14)	0.091 (2)	0.090 (2)	−0.0036 (15)	0.0118 (15)	0.0011 (18)
C5	0.0418 (14)	0.0602 (15)	0.0793 (18)	0.0021 (12)	0.0048 (13)	0.0025 (13)
C6	0.0410 (12)	0.0461 (12)	0.0514 (13)	−0.0033 (10)	0.0015 (10)	−0.0093 (10)
C7	0.0463 (14)	0.0565 (14)	0.0597 (15)	0.0112 (12)	0.0063 (12)	0.0059 (12)
C8	0.095 (2)	0.082 (2)	0.0727 (19)	−0.0204 (19)	0.0134 (18)	−0.0077 (16)
C9	0.106 (3)	0.119 (3)	0.095 (3)	−0.014 (2)	0.009 (2)	−0.038 (2)
C10	0.092 (3)	0.178 (5)	0.082 (2)	0.019 (3)	0.009 (2)	−0.049 (3)
C11	0.132 (4)	0.216 (6)	0.059 (2)	−0.014 (4)	0.018 (2)	0.022 (3)
C12	0.100 (3)	0.141 (3)	0.072 (2)	−0.027 (2)	0.023 (2)	0.021 (2)

Cl1—C3	1.731 (4)	C10—C11	1.468 (8)
S1—O1	1.431 (2)	C11—C12	1.531 (6)
S1—O2	1.425 (2)	C1—H1	0.9300
S1—N1	1.594 (2)	C2—H2	0.9300
S1—C6	1.762 (3)	C4—H4	0.9300
N1—C7	1.475 (3)	C5—H5	0.9300
N1—H1N	0.85 (4)	C7—H7	0.9800
C1—C2	1.366 (4)	C8—H8A	0.9700
C1—C6	1.384 (4)	C8—H8B	0.9700
C2—C3	1.370 (5)	C9—H9A	0.9700
C3—C4	1.370 (4)	C9—H9B	0.9700
C4—C5	1.374 (4)	C10—H10A	0.9700
C5—C6	1.376 (3)	C10—H10B	0.9700
C7—C12	1.510 (5)	C11—H11A	0.9700
C7—C8	1.489 (4)	C11—H11B	0.9700
C8—C9	1.517 (5)	C12—H12A	0.9700
C9—C10	1.478 (6)	C12—H12B	0.9700
O1—S1—O2	119.45 (12)	C5—C4—H4	120.00
O1—S1—N1	106.00 (12)	C4—C5—H5	120.00
O1—S1—C6	105.28 (12)	C6—C5—H5	120.00
O2—S1—N1	108.77 (12)	N1—C7—H7	108.00
O2—S1—C6	107.29 (11)	C8—C7—H7	108.00
N1—S1—C6	109.82 (11)	C12—C7—H7	108.00
S1—N1—C7	123.29 (16)	C7—C8—H8A	109.00
S1—N1—H1N	114 (3)	C7—C8—H8B	109.00
C7—N1—H1N	116 (3)	C9—C8—H8A	109.00
C2—C1—C6	120.0 (2)	C9—C8—H8B	109.00
C1—C2—C3	119.6 (3)	H8A—C8—H8B	108.00
Cl1—C3—C2	119.2 (2)	C8—C9—H9A	109.00
C2—C3—C4	121.1 (3)	C8—C9—H9B	109.00
Cl1—C3—C4	119.7 (2)	C10—C9—H9A	109.00
C3—C4—C5	119.5 (2)	C10—C9—H9B	109.00
C4—C5—C6	119.9 (2)	H9A—C9—H9B	108.00
S1—C6—C1	120.05 (17)	C9—C10—H10A	109.00
S1—C6—C5	119.92 (19)	C9—C10—H10B	109.00
C1—C6—C5	120.0 (2)	C11—C10—H10A	109.00
N1—C7—C8	113.5 (2)	C11—C10—H10B	109.00
C8—C7—C12	111.2 (3)	H10A—C10—H10B	108.00
N1—C7—C12	107.7 (2)	C10—C11—H11A	109.00
C7—C8—C9	112.1 (3)	C10—C11—H11B	109.00
C8—C9—C10	111.9 (4)	C12—C11—H11A	109.00
C9—C10—C11	112.3 (4)	C12—C11—H11B	109.00
C10—C11—C12	113.0 (4)	H11A—C11—H11B	108.00
C7—C12—C11	110.8 (4)	C7—C12—H12A	110.00
C2—C1—H1	120.00	C7—C12—H12B	109.00
C6—C1—H1	120.00	C11—C12—H12A	109.00
C1—C2—H2	120.00	C11—C12—H12B	109.00
C3—C2—H2	120.00	H12A—C12—H12B	108.00
C3—C4—H4	120.00
O1—S1—N1—C7	168.78 (18)	C1—C2—C3—Cl1	178.7 (2)
O2—S1—N1—C7	39.2 (2)	Cl1—C3—C4—C5	−179.3 (2)
C6—S1—N1—C7	−78.0 (2)	C2—C3—C4—C5	0.6 (5)
N1—S1—C6—C5	135.6 (2)	C3—C4—C5—C6	0.6 (4)
O2—S1—C6—C1	−165.3 (2)	C4—C5—C6—S1	176.1 (2)
N1—S1—C6—C1	−47.2 (2)	C4—C5—C6—C1	−1.1 (4)
O1—S1—C6—C1	66.5 (2)	N1—C7—C8—C9	176.1 (3)
O2—S1—C6—C5	17.5 (2)	C12—C7—C8—C9	54.6 (4)
O1—S1—C6—C5	−110.7 (2)	N1—C7—C12—C11	−178.0 (3)
S1—N1—C7—C12	−144.8 (2)	C8—C7—C12—C11	−53.2 (4)
S1—N1—C7—C8	91.8 (2)	C7—C8—C9—C10	−54.4 (4)
C6—C1—C2—C3	0.7 (4)	C8—C9—C10—C11	53.3 (5)
C2—C1—C6—S1	−176.7 (2)	C9—C10—C11—C12	−53.2 (6)
C2—C1—C6—C5	0.5 (4)	C10—C11—C12—C7	53.0 (5)
C1—C2—C3—C4	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (4)	2.05 (4)	2.891 (4)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (4)	2.05 (4)	2.891 (4)	170 (3)

Symmetry code: (i) .