N-[4-(N-Cyclo-hexyl-sulfamo-yl)phen-yl]acetamide.

In the title compound, C(14)H(20)N(2)O(3)S, the cyclo-hexyl ring adopts a chair conformation: the four coplanar C atoms of this ring make a dihedral angle of 64.8 (2)° with the benzene ring. In the mol-ecule, an intra-molecular C-H⋯O contact generates an S(6) ring motif. In the crystal structure, mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds into two-dimensional layers propagating in (100).

Related literature

For related structures, see: Sharif et al. (2010 ▶); Mariam et al. (2009a ▶,b ▶); Asiri et al. (2009 ▶); Khan et al. (2009 ▶); Arshad et al. (2008 ▶, 2009 ▶); Gowda et al. (2007a ▶,b ▶,c ▶); Haider et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C14H20N2O3S

M = 296.39

Monoclinic,

a = 14.6929 (19) Å

b = 13.3486 (19) Å

c = 7.9769 (12) Å

β = 102.387 (7)°

V = 1528.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.32 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

11442 measured reflections

3628 independent reflections

1358 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.218

S = 0.94

3628 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.38 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 datablocks global, I. DOI: 10.1107/S160053681000961X/hb5359sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000961X/hb5359Isup2.hkl

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

C14H20N2O3S	F(000) = 632
Mr = 296.39	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1027 reflections
a = 14.6929 (19) Å	θ = 3.0–18.7°
b = 13.3486 (19) Å	µ = 0.22 mm−1
c = 7.9769 (12) Å	T = 296 K
β = 102.387 (7)°	Needle, colourless
V = 1528.1 (4) Å3	0.32 × 0.09 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	1358 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.110
graphite	θmax = 28.0°, θmin = 1.4°
φ and ω scans	h = −19→16
11442 measured reflections	k = −17→16
3628 independent reflections	l = −10→9

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0926P)2] where P = (Fo2 + 2Fc2)/3
3628 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.38 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 esds 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	0.68133 (8)	0.41022 (7)	0.21719 (15)	0.0554 (4)
O1	0.7323 (2)	0.3332 (2)	0.1552 (4)	0.0645 (11)
O2	0.6417 (2)	0.4904 (2)	0.1059 (4)	0.0679 (11)
O3	0.2838 (2)	0.3369 (2)	0.5231 (4)	0.0801 (15)
N1	0.7470 (2)	0.4618 (2)	0.3789 (5)	0.0619 (13)
N2	0.3647 (2)	0.2116 (2)	0.4351 (4)	0.0515 (11)
C1	0.9600 (4)	0.3914 (5)	0.8177 (8)	0.098 (3)
C2	0.9654 (3)	0.3437 (5)	0.6484 (8)	0.101 (3)
C3	0.9037 (3)	0.3989 (4)	0.4997 (7)	0.078 (2)
C4	0.8045 (3)	0.4037 (3)	0.5194 (6)	0.0537 (16)
C5	0.7987 (3)	0.4482 (4)	0.6899 (6)	0.0732 (19)
C6	0.8608 (4)	0.3946 (4)	0.8377 (7)	0.085 (2)
C7	0.5888 (3)	0.3520 (3)	0.2880 (5)	0.0468 (16)
C8	0.5176 (3)	0.4092 (3)	0.3263 (6)	0.0585 (16)
C9	0.4436 (3)	0.3657 (3)	0.3762 (6)	0.0553 (16)
C10	0.4389 (3)	0.2626 (3)	0.3903 (5)	0.0437 (12)
C11	0.5109 (3)	0.2061 (3)	0.3535 (5)	0.0488 (16)
C12	0.5852 (3)	0.2493 (3)	0.3041 (5)	0.0483 (16)
C13	0.2927 (3)	0.2488 (3)	0.4952 (5)	0.0533 (17)
C14	0.2223 (3)	0.1742 (4)	0.5213 (7)	0.0773 (19)
H1	0.74890	0.52610	0.38430	0.0750*
H1A	0.99740	0.35330	0.91120	0.1180*
H1B	0.98490	0.45900	0.82250	0.1180*
H2	0.36500	0.14760	0.42250	0.0620*
H2A	0.94580	0.27430	0.64800	0.1210*
H2B	1.02940	0.34490	0.63450	0.1210*
H3A	0.92720	0.46630	0.49340	0.0940*
H3B	0.90600	0.36490	0.39320	0.0940*
H4	0.77990	0.33530	0.51440	0.0650*
H5A	0.73470	0.44490	0.70360	0.0870*
H5B	0.81650	0.51820	0.69190	0.0870*
H6A	0.85800	0.42850	0.94400	0.1010*
H6B	0.83830	0.32670	0.84440	0.1010*
H8	0.52010	0.47860	0.31800	0.0700*
H9	0.39620	0.40550	0.40070	0.0660*
H11	0.50880	0.13670	0.36270	0.0580*
H12	0.63320	0.20960	0.28140	0.0580*
H14A	0.17610	0.20640	0.57140	0.1160*
H14B	0.25220	0.12230	0.59670	0.1160*
H14C	0.19300	0.14550	0.41280	0.1160*

	U11	U22	U33	U12	U13	U23
S1	0.0707 (8)	0.0406 (6)	0.0528 (8)	−0.0034 (6)	0.0085 (6)	0.0005 (6)
O1	0.083 (2)	0.0502 (16)	0.065 (2)	0.0036 (15)	0.0264 (17)	−0.0055 (15)
O2	0.089 (2)	0.0530 (17)	0.060 (2)	−0.0026 (16)	0.0121 (17)	0.0160 (16)
O3	0.111 (3)	0.0498 (19)	0.088 (3)	0.0200 (18)	0.040 (2)	−0.0019 (18)
N1	0.077 (2)	0.0364 (18)	0.064 (3)	−0.0082 (17)	−0.003 (2)	−0.0040 (18)
N2	0.064 (2)	0.0383 (18)	0.051 (2)	−0.0023 (18)	0.0095 (18)	−0.0030 (16)
C1	0.078 (4)	0.114 (5)	0.089 (5)	−0.001 (3)	−0.013 (3)	0.001 (4)
C2	0.059 (3)	0.135 (5)	0.104 (6)	0.014 (3)	0.009 (3)	−0.004 (4)
C3	0.064 (3)	0.103 (4)	0.068 (4)	−0.003 (3)	0.017 (3)	−0.006 (3)
C4	0.056 (3)	0.040 (2)	0.062 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C5	0.083 (3)	0.070 (3)	0.069 (4)	0.005 (3)	0.022 (3)	−0.003 (3)
C6	0.102 (4)	0.095 (4)	0.055 (4)	0.015 (3)	0.012 (3)	0.005 (3)
C7	0.062 (3)	0.040 (2)	0.033 (3)	0.001 (2)	−0.002 (2)	−0.0018 (18)
C8	0.079 (3)	0.030 (2)	0.065 (3)	0.000 (2)	0.012 (3)	−0.002 (2)
C9	0.071 (3)	0.038 (2)	0.060 (3)	0.006 (2)	0.021 (2)	0.001 (2)
C10	0.058 (2)	0.038 (2)	0.029 (2)	0.002 (2)	−0.0040 (19)	−0.0041 (18)
C11	0.068 (3)	0.031 (2)	0.043 (3)	0.000 (2)	0.002 (2)	−0.0018 (19)
C12	0.063 (3)	0.036 (2)	0.044 (3)	0.003 (2)	0.007 (2)	−0.0042 (18)
C13	0.071 (3)	0.051 (3)	0.036 (3)	0.007 (2)	0.007 (2)	0.001 (2)
C14	0.077 (3)	0.079 (3)	0.081 (4)	−0.001 (3)	0.028 (3)	−0.002 (3)

S1—O1	1.422 (3)	C11—C12	1.365 (6)
S1—O2	1.432 (3)	C13—C14	1.482 (7)
S1—N1	1.592 (4)	C1—H1A	0.9700
S1—C7	1.761 (4)	C1—H1B	0.9700
O3—C13	1.209 (5)	C2—H2A	0.9700
N1—C4	1.471 (6)	C2—H2B	0.9700
N2—C10	1.395 (5)	C3—H3A	0.9700
N2—C13	1.347 (5)	C3—H3B	0.9700
N1—H1	0.8600	C4—H4	0.9800
N2—H2	0.8600	C5—H5A	0.9700
C1—C6	1.501 (9)	C5—H5B	0.9700
C1—C2	1.511 (9)	C6—H6A	0.9700
C2—C3	1.520 (8)	C6—H6B	0.9700
C3—C4	1.501 (6)	C8—H8	0.9300
C4—C5	1.503 (7)	C9—H9	0.9300
C5—C6	1.508 (7)	C11—H11	0.9300
C7—C12	1.379 (6)	C12—H12	0.9300
C7—C8	1.381 (6)	C14—H14A	0.9600
C8—C9	1.365 (6)	C14—H14B	0.9600
C9—C10	1.384 (6)	C14—H14C	0.9600
C10—C11	1.381 (6)
O1—S1—O2	119.96 (19)	C1—C2—H2A	109.00
O1—S1—N1	108.76 (18)	C1—C2—H2B	109.00
O1—S1—C7	107.04 (18)	C3—C2—H2A	109.00
O2—S1—N1	105.91 (17)	C3—C2—H2B	109.00
O2—S1—C7	106.83 (19)	H2A—C2—H2B	108.00
N1—S1—C7	107.84 (19)	C2—C3—H3A	109.00
S1—N1—C4	122.6 (2)	C2—C3—H3B	109.00
C10—N2—C13	128.9 (3)	C4—C3—H3A	109.00
C4—N1—H1	119.00	C4—C3—H3B	109.00
S1—N1—H1	119.00	H3A—C3—H3B	108.00
C10—N2—H2	116.00	N1—C4—H4	108.00
C13—N2—H2	116.00	C3—C4—H4	108.00
C2—C1—C6	110.2 (5)	C5—C4—H4	108.00
C1—C2—C3	110.9 (5)	C4—C5—H5A	109.00
C2—C3—C4	111.7 (4)	C4—C5—H5B	109.00
N1—C4—C5	110.3 (4)	C6—C5—H5A	109.00
C3—C4—C5	110.9 (4)	C6—C5—H5B	109.00
N1—C4—C3	110.8 (4)	H5A—C5—H5B	108.00
C4—C5—C6	112.2 (4)	C1—C6—H6A	109.00
C1—C6—C5	111.7 (5)	C1—C6—H6B	109.00
C8—C7—C12	118.9 (4)	C5—C6—H6A	109.00
S1—C7—C8	120.0 (3)	C5—C6—H6B	109.00
S1—C7—C12	121.1 (3)	H6A—C6—H6B	108.00
C7—C8—C9	121.2 (4)	C7—C8—H8	119.00
C8—C9—C10	120.2 (4)	C9—C8—H8	119.00
N2—C10—C9	124.2 (4)	C8—C9—H9	120.00
N2—C10—C11	117.7 (3)	C10—C9—H9	120.00
C9—C10—C11	118.2 (4)	C10—C11—H11	119.00
C10—C11—C12	121.8 (4)	C12—C11—H11	119.00
C7—C12—C11	119.7 (4)	C7—C12—H12	120.00
O3—C13—C14	121.4 (4)	C11—C12—H12	120.00
N2—C13—C14	115.3 (4)	C13—C14—H14A	110.00
O3—C13—N2	123.3 (4)	C13—C14—H14B	109.00
C2—C1—H1A	110.00	C13—C14—H14C	109.00
C2—C1—H1B	110.00	H14A—C14—H14B	109.00
C6—C1—H1A	110.00	H14A—C14—H14C	109.00
C6—C1—H1B	110.00	H14B—C14—H14C	109.00
H1A—C1—H1B	108.00
O1—S1—N1—C4	−46.6 (4)	C1—C2—C3—C4	−56.3 (6)
O2—S1—N1—C4	−176.8 (3)	C2—C3—C4—N1	177.1 (4)
C7—S1—N1—C4	69.2 (4)	C2—C3—C4—C5	54.4 (6)
O1—S1—C7—C8	−168.3 (3)	N1—C4—C5—C6	−176.8 (4)
O1—S1—C7—C12	10.9 (4)	C3—C4—C5—C6	−53.8 (5)
O2—S1—C7—C8	−38.6 (4)	C4—C5—C6—C1	55.2 (6)
O2—S1—C7—C12	140.5 (3)	S1—C7—C8—C9	177.9 (4)
N1—S1—C7—C8	74.8 (4)	C12—C7—C8—C9	−1.3 (7)
N1—S1—C7—C12	−106.0 (3)	S1—C7—C12—C11	−177.7 (3)
S1—N1—C4—C3	100.2 (4)	C8—C7—C12—C11	1.5 (6)
S1—N1—C4—C5	−136.7 (3)	C7—C8—C9—C10	0.4 (7)
C13—N2—C10—C9	−10.3 (6)	C8—C9—C10—N2	−177.9 (4)
C13—N2—C10—C11	171.5 (4)	C8—C9—C10—C11	0.3 (6)
C10—N2—C13—O3	−1.7 (7)	N2—C10—C11—C12	178.3 (4)
C10—N2—C13—C14	176.7 (4)	C9—C10—C11—C12	−0.1 (6)
C6—C1—C2—C3	56.5 (6)	C10—C11—C12—C7	−0.8 (6)
C2—C1—C6—C5	−56.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.07	2.862 (4)	153
N2—H2···O2ii	0.86	2.11	2.970 (4)	177
C9—H9···O3	0.93	2.28	2.866 (5)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.07	2.862 (4)	153
N2—H2⋯O2ii	0.86	2.11	2.970 (4)	177
C9—H9⋯O3	0.93	2.28	2.866 (5)	120

Symmetry codes: (i) ; (ii) .