2,5-Dichloro-N-cyclo-hexyl-benzene-sulfonamide.

The structure of the title sulfonamide, C(12)H(15)Cl(2)NO(2)S, features a distorted tetra-hedral geometry for the S atom [maximum deviation: O-S-O = 120.23 (14)°]. One of the sulfonamide O atoms is coplanar with the benzene ring [C-C-S-O torsion angle = -174.5 (2)°], whereas the other lies well above the plane [C-C-S-O = 57.0 (3)°]. A chair conformation is found for the cyclo-hexyl ring. In the crystal, supra-molecular chains aligned along the c axis are formed via N-H⋯O hydrogen bonds; these are consolidated in the three-dimensional packing by C-H⋯O contacts involving the second sulfonamide O atom.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C12H15Cl2NO2S

M = 308.21

Monoclinic,

a = 17.4471 (12) Å

b = 10.7574 (8) Å

c = 8.2845 (6) Å

β = 111.956 (4)°

V = 1442.11 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 293 K

0.28 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.692, T max = 0.895

6491 measured reflections

2983 independent reflections

2492 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 1.01

2983 reflections

166 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1327 Friedel pairs

Flack parameter: 0.06 (7)

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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003789X/hg2717sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003789X/hg2717Isup2.hkl

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

C12H15Cl2NO2S	F(000) = 640
Mr = 308.21	Dx = 1.420 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2154 reflections
a = 17.4471 (12) Å	θ = 2.3–25.8°
b = 10.7574 (8) Å	µ = 0.59 mm−1
c = 8.2845 (6) Å	T = 293 K
β = 111.956 (4)°	Block, colourless
V = 1442.11 (18) Å3	0.28 × 0.14 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2492 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.692, Tmax = 0.895	k = −13→10
6491 measured reflections	l = −10→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0499P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2983 reflections	Δρmax = 0.24 e Å−3
166 parameters	Δρmin = −0.19 e Å−3
3 restraints	Absolute structure: Flack (1983), 1327 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (7)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.74062 (5)	0.95016 (10)	0.40157 (10)	0.0731 (3)
Cl2	0.71411 (6)	0.53058 (11)	0.89049 (15)	0.0905 (4)
S1	0.90528 (4)	0.86294 (6)	0.72894 (8)	0.04118 (17)
O1	0.96062 (11)	0.7885 (2)	0.8655 (3)	0.0571 (6)
O2	0.89603 (14)	0.99251 (19)	0.7564 (3)	0.0608 (6)
N1	0.93057 (15)	0.8530 (2)	0.5645 (3)	0.0457 (6)
H1n	0.9127 (18)	0.912 (2)	0.486 (3)	0.055*
C1	0.80608 (14)	0.7947 (2)	0.6796 (3)	0.0373 (6)
C2	0.73570 (17)	0.8342 (3)	0.5422 (4)	0.0448 (7)
C3	0.66045 (17)	0.7810 (3)	0.5144 (4)	0.0540 (8)
H3	0.6137	0.8089	0.4232	0.065*
C4	0.65355 (18)	0.6871 (3)	0.6199 (4)	0.0533 (7)
H4	0.6027	0.6499	0.5995	0.064*
C5	0.72223 (19)	0.6489 (3)	0.7549 (4)	0.0510 (7)
C6	0.79885 (17)	0.7007 (3)	0.7871 (3)	0.0436 (6)
H6	0.8450	0.6729	0.8798	0.052*
C7	0.96379 (16)	0.7403 (2)	0.5145 (4)	0.0392 (6)
H7	0.9751	0.6793	0.6085	0.047*
C8	0.90286 (18)	0.6836 (3)	0.3500 (4)	0.0550 (8)
H8A	0.8874	0.7450	0.2575	0.066*
H8B	0.8533	0.6593	0.3689	0.066*
C9	0.9399 (2)	0.5697 (3)	0.2951 (5)	0.0608 (9)
H9A	0.9499	0.5050	0.3821	0.073*
H9B	0.9008	0.5379	0.1858	0.073*
C10	1.0206 (2)	0.6020 (3)	0.2741 (4)	0.0624 (9)
H10A	1.0442	0.5274	0.2457	0.075*
H10B	1.0099	0.6605	0.1791	0.075*
C11	1.0810 (2)	0.6580 (3)	0.4394 (4)	0.0564 (8)
H11A	1.1308	0.6823	0.4216	0.068*
H11B	1.0961	0.5961	0.5313	0.068*
C12	1.04439 (17)	0.7717 (3)	0.4958 (4)	0.0471 (7)
H12A	1.0834	0.8022	0.6061	0.056*
H12B	1.0352	0.8372	0.4101	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0545 (5)	0.0915 (7)	0.0708 (6)	0.0203 (4)	0.0206 (4)	0.0393 (5)
Cl2	0.0742 (6)	0.0882 (7)	0.1198 (9)	0.0010 (5)	0.0486 (6)	0.0425 (6)
S1	0.0346 (3)	0.0513 (4)	0.0368 (3)	−0.0019 (3)	0.0124 (2)	−0.0063 (3)
O1	0.0349 (10)	0.0900 (16)	0.0400 (11)	−0.0033 (10)	0.0066 (9)	0.0081 (10)
O2	0.0674 (14)	0.0549 (12)	0.0639 (14)	−0.0091 (11)	0.0290 (11)	−0.0221 (11)
N1	0.0516 (14)	0.0457 (14)	0.0473 (14)	0.0123 (10)	0.0273 (12)	0.0108 (10)
C1	0.0318 (12)	0.0465 (15)	0.0337 (13)	0.0026 (11)	0.0122 (10)	−0.0074 (11)
C2	0.0385 (14)	0.0551 (17)	0.0391 (15)	0.0093 (12)	0.0127 (12)	0.0014 (13)
C3	0.0327 (13)	0.076 (2)	0.0446 (18)	0.0084 (15)	0.0045 (13)	−0.0017 (15)
C4	0.0370 (15)	0.0645 (19)	0.0588 (18)	−0.0071 (14)	0.0183 (14)	−0.0115 (16)
C5	0.0482 (17)	0.0492 (18)	0.0612 (18)	0.0026 (13)	0.0267 (15)	0.0045 (15)
C6	0.0366 (14)	0.0536 (17)	0.0415 (15)	0.0052 (12)	0.0155 (12)	0.0037 (13)
C7	0.0409 (13)	0.0369 (14)	0.0438 (15)	0.0050 (11)	0.0204 (12)	0.0045 (11)
C8	0.0445 (16)	0.0543 (18)	0.0625 (19)	−0.0063 (13)	0.0159 (14)	−0.0042 (15)
C9	0.070 (2)	0.0468 (18)	0.0565 (19)	−0.0033 (15)	0.0132 (17)	−0.0089 (14)
C10	0.084 (2)	0.0563 (18)	0.0522 (19)	0.0169 (17)	0.0323 (18)	−0.0001 (15)
C11	0.0528 (17)	0.066 (2)	0.061 (2)	0.0148 (15)	0.0330 (16)	0.0026 (16)
C12	0.0381 (14)	0.0541 (17)	0.0512 (16)	0.0005 (12)	0.0192 (13)	−0.0029 (13)

Cl1—C2	1.731 (3)	C7—C8	1.508 (4)
Cl2—C5	1.738 (3)	C7—C12	1.510 (4)
S1—O1	1.427 (2)	C7—H7	0.9800
S1—O2	1.431 (2)	C8—C9	1.532 (5)
S1—N1	1.585 (2)	C8—H8A	0.9700
S1—C1	1.781 (3)	C8—H8B	0.9700
N1—C7	1.469 (3)	C9—C10	1.521 (5)
N1—H1n	0.88 (2)	C9—H9A	0.9700
C1—C6	1.384 (4)	C9—H9B	0.9700
C1—C2	1.392 (3)	C10—C11	1.507 (5)
C2—C3	1.370 (4)	C10—H10A	0.9700
C3—C4	1.371 (5)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.531 (4)
C4—C5	1.362 (4)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.379 (4)	C12—H12A	0.9700
C6—H6	0.9300	C12—H12B	0.9700
O1—S1—O2	120.23 (14)	C12—C7—H7	108.2
O1—S1—N1	108.69 (13)	C7—C8—C9	111.0 (2)
O2—S1—N1	106.64 (13)	C7—C8—H8A	109.4
O1—S1—C1	105.20 (13)	C9—C8—H8A	109.4
O2—S1—C1	106.27 (13)	C7—C8—H8B	109.4
N1—S1—C1	109.51 (13)	C9—C8—H8B	109.4
C7—N1—S1	124.32 (19)	H8A—C8—H8B	108.0
C7—N1—H1N	117 (2)	C10—C9—C8	111.3 (3)
S1—N1—H1N	117 (2)	C10—C9—H9A	109.4
C6—C1—C2	119.0 (2)	C8—C9—H9A	109.4
C6—C1—S1	117.89 (19)	C10—C9—H9B	109.4
C2—C1—S1	123.1 (2)	C8—C9—H9B	109.4
C3—C2—C1	120.4 (3)	H9A—C9—H9B	108.0
C3—C2—Cl1	118.2 (2)	C11—C10—C9	110.5 (3)
C1—C2—Cl1	121.3 (2)	C11—C10—H10A	109.6
C2—C3—C4	120.5 (3)	C9—C10—H10A	109.6
C2—C3—H3	119.7	C11—C10—H10B	109.6
C4—C3—H3	119.7	C9—C10—H10B	109.6
C5—C4—C3	119.1 (3)	H10A—C10—H10B	108.1
C5—C4—H4	120.4	C10—C11—C12	111.5 (3)
C3—C4—H4	120.4	C10—C11—H11A	109.3
C4—C5—C6	121.9 (3)	C12—C11—H11A	109.3
C4—C5—Cl2	119.5 (2)	C10—C11—H11B	109.3
C6—C5—Cl2	118.6 (2)	C12—C11—H11B	109.3
C5—C6—C1	119.1 (3)	H11A—C11—H11B	108.0
C5—C6—H6	120.5	C7—C12—C11	111.3 (3)
C1—C6—H6	120.5	C7—C12—H12A	109.4
N1—C7—C8	111.7 (2)	C11—C12—H12A	109.4
N1—C7—C12	109.0 (2)	C7—C12—H12B	109.4
C8—C7—C12	111.5 (2)	C11—C12—H12B	109.4
N1—C7—H7	108.2	H12A—C12—H12B	108.0
C8—C7—H7	108.2
O1—S1—N1—C7	34.9 (3)	C3—C4—C5—C6	−1.0 (5)
O2—S1—N1—C7	165.9 (2)	C3—C4—C5—Cl2	179.6 (2)
C1—S1—N1—C7	−79.5 (2)	C4—C5—C6—C1	0.4 (4)
O1—S1—C1—C6	7.6 (2)	Cl2—C5—C6—C1	179.8 (2)
O2—S1—C1—C6	−120.9 (2)	C2—C1—C6—C5	0.1 (4)
N1—S1—C1—C6	124.3 (2)	S1—C1—C6—C5	178.1 (2)
O1—S1—C1—C2	−174.5 (2)	S1—N1—C7—C8	110.4 (3)
O2—S1—C1—C2	57.0 (3)	S1—N1—C7—C12	−126.0 (2)
N1—S1—C1—C2	−57.8 (2)	N1—C7—C8—C9	177.4 (3)
C6—C1—C2—C3	0.2 (4)	C12—C7—C8—C9	55.2 (4)
S1—C1—C2—C3	−177.7 (2)	C7—C8—C9—C10	−55.8 (4)
C6—C1—C2—Cl1	−179.3 (2)	C8—C9—C10—C11	56.1 (4)
S1—C1—C2—Cl1	2.8 (3)	C9—C10—C11—C12	−55.8 (4)
C1—C2—C3—C4	−0.9 (4)	N1—C7—C12—C11	−178.7 (2)
Cl1—C2—C3—C4	178.6 (2)	C8—C7—C12—C11	−55.0 (3)
C2—C3—C4—C5	1.3 (5)	C10—C11—C12—C7	55.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2i	0.88 (2)	2.08 (2)	2.914 (3)	157 (2)
C4—H4···O1ii	0.93	2.60	3.246 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2i	0.88 (2)	2.08 (2)	2.914 (3)	157 (2)
C4—H4⋯O1ii	0.93	2.60	3.246 (4)	127

Symmetry codes: (i) ; (ii) .