N-Cyclo-hexyl-4-meth-oxy-benzene-sulfonamide.

In the title mol-ecule, C(13)H(19)NO(3)S, the S atom has a distorted tetra-hedral geometry with an O-S-O bond angle of 120.39 (18)°. The cyclo-hexane ring has a chair conformation. In the crystal, mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds, forming zigzag hydrogen-bonded chains directed along the c axis.

Related literature

For background to the biological activity of sulfonamides, see: Gennarti et al. (1994 ▶); Hanson et al. (1999 ▶); Moree et al. (1991 ▶); Ozbek et al. (2007 ▶); Rough et al. (1998 ▶); Siddiqui et al. (2007 ▶). For literature on sulfonamide derivatives, see: Akkurt et al. (2011 ▶); Aziz-ur-Rehman, Rafique et al. (2010 ▶); Aziz-ur-Rehman, Sajjad et al. (2010 ▶); Aziz-ur-Rehman, Siddiqa et al. (2010 ▶); Khan, Akkurt et al. (2010 ▶); Khan, Sharif et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H19NO3S

M = 269.36

Orthorhombic,

a = 17.2644 (12) Å

b = 20.4707 (16) Å

c = 7.9139 (5) Å

V = 2796.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.29 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

10601 measured reflections

2704 independent reflections

1945 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.02

2704 reflections

167 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 829 Freidel pairs

Flack parameter: −0.05 (12)

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 datablocks global, I. DOI: 10.1107/S1600536811009172/xu5173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009172/xu5173Isup2.hkl

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

C13H19NO3S	F(000) = 1152
Mr = 269.36	Dx = 1.279 Mg m−3
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 3418 reflections
a = 17.2644 (12) Å	θ = 2.3–24.7°
b = 20.4707 (16) Å	µ = 0.23 mm−1
c = 7.9139 (5) Å	T = 296 K
V = 2796.9 (3) Å3	Prism, light brown
Z = 8	0.29 × 0.12 × 0.09 mm

Bruker APEXII CCD diffractometer	1945 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.047
graphite	θmax = 28.3°, θmin = 3.0°
φ and ω scans	h = −23→23
10601 measured reflections	k = −23→27
2704 independent reflections	l = −10→6

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0633P)2 + 1.387P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2704 reflections	Δρmax = 0.17 e Å−3
167 parameters	Δρmin = −0.27 e Å−3
2 restraints	Absolute structure: Flack (1983), 829 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (12)

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
S1	0.16185 (4)	0.09694 (5)	0.20157 (12)	0.0614 (3)
O1	0.09659 (16)	0.11080 (14)	0.3056 (4)	0.0832 (11)
O2	0.23822 (17)	0.11611 (14)	0.2537 (4)	0.0901 (11)
O3	0.16806 (14)	−0.18793 (14)	0.1087 (4)	0.0822 (11)
N1	0.14869 (13)	0.13120 (14)	0.0241 (4)	0.0556 (10)
C1	0.0682 (2)	0.20104 (16)	−0.1482 (5)	0.0697 (15)
C2	−0.0103 (3)	0.21102 (18)	−0.2295 (6)	0.0850 (16)
C3	−0.0294 (2)	0.15634 (19)	−0.3505 (5)	0.0710 (16)
C4	−0.0226 (2)	0.09157 (18)	−0.2642 (6)	0.0783 (16)
C5	0.0557 (2)	0.08162 (16)	−0.1777 (6)	0.0724 (13)
C6	0.07253 (15)	0.13658 (15)	−0.0581 (4)	0.0501 (10)
C7	0.16495 (15)	0.01229 (17)	0.1741 (4)	0.0515 (10)
C8	0.10900 (15)	−0.0285 (2)	0.2421 (4)	0.0613 (13)
C9	0.11159 (16)	−0.09474 (19)	0.2187 (5)	0.0621 (11)
C10	0.17072 (17)	−0.12166 (19)	0.1247 (5)	0.0576 (11)
C11	0.22723 (18)	−0.08270 (18)	0.0575 (6)	0.0693 (16)
C12	0.22479 (17)	−0.01640 (19)	0.0830 (5)	0.0694 (15)
C13	0.2233 (3)	−0.2198 (2)	0.0041 (8)	0.111 (2)
HN1	0.1894 (15)	0.1299 (18)	−0.037 (4)	0.0740*
H1A	0.10810	0.20280	−0.23440	0.0840*
H1B	0.07780	0.23610	−0.06840	0.0840*
H2A	−0.04970	0.21310	−0.14230	0.1020*
H2B	−0.01050	0.25220	−0.29000	0.1020*
H3A	−0.08170	0.16190	−0.39270	0.0860*
H3B	0.00570	0.15780	−0.44610	0.0860*
H4A	−0.03020	0.05720	−0.34680	0.0940*
H4B	−0.06340	0.08780	−0.18040	0.0940*
H5A	0.05530	0.04060	−0.11610	0.0870*
H5B	0.09620	0.07930	−0.26240	0.0870*
H6	0.03280	0.13630	0.03040	0.0600*
H8	0.06880	−0.01050	0.30500	0.0740*
H9	0.07370	−0.12140	0.26590	0.0750*
H11	0.26720	−0.10110	−0.00540	0.0830*
H12	0.26380	0.00980	0.03860	0.0830*
H13A	0.22010	−0.20250	−0.10840	0.1670*
H13B	0.21260	−0.26580	0.00190	0.1670*
H13C	0.27430	−0.21260	0.04830	0.1670*

	U11	U22	U33	U12	U13	U23
S1	0.0628 (4)	0.0785 (6)	0.0429 (4)	0.0052 (4)	−0.0071 (4)	−0.0091 (5)
O1	0.0961 (19)	0.106 (2)	0.0476 (16)	0.0250 (15)	0.0154 (14)	−0.0076 (15)
O2	0.0793 (17)	0.107 (2)	0.084 (2)	−0.0051 (15)	−0.0333 (15)	−0.0189 (17)
O3	0.0877 (18)	0.0690 (18)	0.090 (2)	−0.0011 (13)	0.0110 (15)	0.0140 (15)
N1	0.0457 (13)	0.0707 (19)	0.0503 (17)	−0.0032 (12)	0.0027 (11)	−0.0033 (14)
C1	0.096 (3)	0.0442 (18)	0.069 (3)	−0.0004 (17)	−0.0043 (19)	−0.0053 (19)
C2	0.110 (3)	0.066 (2)	0.079 (3)	0.024 (2)	−0.020 (2)	0.002 (2)
C3	0.082 (2)	0.074 (3)	0.057 (3)	0.0093 (19)	−0.0133 (18)	0.0056 (19)
C4	0.082 (2)	0.064 (2)	0.089 (4)	−0.0068 (18)	−0.033 (2)	0.000 (2)
C5	0.086 (2)	0.0413 (18)	0.090 (3)	0.0029 (17)	−0.028 (2)	−0.0018 (19)
C6	0.0466 (14)	0.057 (2)	0.0467 (18)	0.0002 (12)	0.0011 (13)	0.0052 (14)
C7	0.0403 (13)	0.075 (2)	0.0391 (19)	0.0071 (13)	−0.0031 (12)	0.0041 (15)
C8	0.0380 (14)	0.098 (3)	0.048 (2)	0.0078 (15)	0.0035 (13)	0.0058 (18)
C9	0.0442 (14)	0.084 (2)	0.058 (2)	−0.0074 (15)	0.0043 (16)	0.016 (2)
C10	0.0542 (18)	0.070 (2)	0.0487 (19)	0.0028 (16)	−0.0023 (15)	0.0097 (17)
C11	0.064 (2)	0.074 (3)	0.070 (3)	0.0076 (17)	0.0265 (19)	0.007 (2)
C12	0.0581 (19)	0.082 (3)	0.068 (3)	−0.0029 (16)	0.0222 (17)	0.009 (2)
C13	0.122 (4)	0.091 (3)	0.121 (5)	0.019 (3)	0.035 (3)	−0.009 (3)

S1—O1	1.424 (3)	C11—C12	1.373 (5)
S1—O2	1.436 (3)	C1—H1A	0.9700
S1—N1	1.586 (3)	C1—H1B	0.9700
S1—C7	1.747 (4)	C2—H2A	0.9700
O3—C10	1.363 (5)	C2—H2B	0.9700
O3—C13	1.421 (6)	C3—H3A	0.9700
N1—C6	1.471 (4)	C3—H3B	0.9700
N1—HN1	0.85 (3)	C4—H4A	0.9700
C1—C2	1.514 (6)	C4—H4B	0.9700
C1—C6	1.502 (5)	C5—H5A	0.9700
C2—C3	1.510 (6)	C5—H5B	0.9700
C3—C4	1.496 (6)	C6—H6	0.9800
C4—C5	1.529 (5)	C8—H8	0.9300
C5—C6	1.499 (5)	C9—H9	0.9300
C7—C12	1.390 (4)	C11—H11	0.9300
C7—C8	1.386 (4)	C12—H12	0.9300
C8—C9	1.369 (6)	C13—H13A	0.9600
C9—C10	1.378 (5)	C13—H13B	0.9600
C10—C11	1.368 (5)	C13—H13C	0.9600
O1—S1—O2	120.39 (18)	C3—C2—H2A	109.00
O1—S1—N1	108.09 (16)	C3—C2—H2B	109.00
O1—S1—C7	107.08 (16)	H2A—C2—H2B	108.00
O2—S1—N1	105.37 (16)	C2—C3—H3A	110.00
O2—S1—C7	106.18 (15)	C2—C3—H3B	110.00
N1—S1—C7	109.43 (16)	C4—C3—H3A	110.00
C10—O3—C13	119.2 (3)	C4—C3—H3B	110.00
S1—N1—C6	123.6 (2)	H3A—C3—H3B	108.00
S1—N1—HN1	112 (2)	C3—C4—H4A	109.00
C6—N1—HN1	119 (2)	C3—C4—H4B	109.00
C2—C1—C6	111.4 (3)	C5—C4—H4A	109.00
C1—C2—C3	111.4 (3)	C5—C4—H4B	109.00
C2—C3—C4	110.5 (3)	H4A—C4—H4B	108.00
C3—C4—C5	113.1 (3)	C4—C5—H5A	109.00
C4—C5—C6	110.7 (3)	C4—C5—H5B	110.00
N1—C6—C5	113.4 (3)	C6—C5—H5A	109.00
C1—C6—C5	110.5 (3)	C6—C5—H5B	109.00
N1—C6—C1	108.7 (2)	H5A—C5—H5B	108.00
C8—C7—C12	117.7 (3)	N1—C6—H6	108.00
S1—C7—C8	121.9 (2)	C1—C6—H6	108.00
S1—C7—C12	120.4 (3)	C5—C6—H6	108.00
C7—C8—C9	121.4 (3)	C7—C8—H8	119.00
C8—C9—C10	119.6 (3)	C9—C8—H8	119.00
O3—C10—C11	124.6 (3)	C8—C9—H9	120.00
O3—C10—C9	115.0 (3)	C10—C9—H9	120.00
C9—C10—C11	120.3 (4)	C10—C11—H11	120.00
C10—C11—C12	119.8 (3)	C12—C11—H11	120.00
C7—C12—C11	121.1 (3)	C7—C12—H12	119.00
C2—C1—H1A	109.00	C11—C12—H12	120.00
C2—C1—H1B	109.00	O3—C13—H13A	109.00
C6—C1—H1A	109.00	O3—C13—H13B	109.00
C6—C1—H1B	109.00	O3—C13—H13C	109.00
H1A—C1—H1B	108.00	H13A—C13—H13B	110.00
C1—C2—H2A	109.00	H13A—C13—H13C	110.00
C1—C2—H2B	109.00	H13B—C13—H13C	110.00
O1—S1—N1—C6	−36.4 (3)	C1—C2—C3—C4	54.1 (4)
O2—S1—N1—C6	−166.3 (3)	C2—C3—C4—C5	−53.2 (5)
C7—S1—N1—C6	79.9 (3)	C3—C4—C5—C6	54.4 (5)
N1—S1—C7—C12	65.7 (3)	C4—C5—C6—N1	−177.6 (3)
O2—S1—C7—C8	132.0 (3)	C4—C5—C6—C1	−55.4 (4)
N1—S1—C7—C8	−114.7 (3)	S1—C7—C12—C11	−178.7 (3)
O1—S1—C7—C8	2.2 (3)	C8—C7—C12—C11	1.7 (5)
O2—S1—C7—C12	−47.6 (3)	S1—C7—C8—C9	179.5 (3)
O1—S1—C7—C12	−177.4 (3)	C12—C7—C8—C9	−1.0 (5)
C13—O3—C10—C11	−5.6 (6)	C7—C8—C9—C10	−0.4 (5)
C13—O3—C10—C9	175.5 (4)	C8—C9—C10—C11	1.1 (6)
S1—N1—C6—C1	144.0 (3)	C8—C9—C10—O3	−179.9 (3)
S1—N1—C6—C5	−92.7 (3)	O3—C10—C11—C12	−179.2 (4)
C2—C1—C6—N1	−177.5 (3)	C9—C10—C11—C12	−0.4 (6)
C6—C1—C2—C3	−57.0 (4)	C10—C11—C12—C7	−1.1 (6)
C2—C1—C6—C5	57.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2i	0.85 (3)	2.09 (3)	2.913 (4)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O2i	0.85 (3)	2.09 (3)	2.913 (4)	161 (3)

Symmetry code: (i) .