N-Cyclohexyl-N-methylbenzene-sulfonamide.

The title compound, C(13)H(19)NO(2)S, was synthesized by the reaction of N-cyclo-hexyl-amine-benzene-sulfonamide and methyl iodide. The crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

Compounds containing cyclo­hexyl­amine have been reported to be activators of dopamine receptors in the central nervous system, see: Hacksell et al. (1981 ▶). For related structures, see: Arshad et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C13H19NO2S

M = 253.35

Monoclinic,

a = 9.2729 (5) Å

b = 12.1182 (7) Å

c = 12.5801 (7) Å

β = 109.103 (2)°

V = 1335.79 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.28 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.938, T max = 0.979

12741 measured reflections

2489 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.08

2489 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041762/bt5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041762/bt5092Isup2.hkl

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

C13H19NO2S	F(000) = 544
Mr = 253.35	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3617 reflections
a = 9.2729 (5) Å	θ = 2.3–25.5°
b = 12.1182 (7) Å	µ = 0.23 mm−1
c = 12.5801 (7) Å	T = 296 K
β = 109.103 (2)°	Block, colourless
V = 1335.79 (13) Å3	0.28 × 0.12 × 0.09 mm
Z = 4

Bruker APEXII CCD detector diffractometer	2489 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
Tmin = 0.938, Tmax = 0.979	k = −14→14
12741 measured reflections	l = −13→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2086P] where P = (Fo2 + 2Fc2)/3
2489 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.25 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	0.67239 (19)	0.36402 (15)	0.21562 (15)	0.0443 (5)
C2	0.6576 (2)	0.33212 (18)	0.31729 (17)	0.0556 (5)
H2	0.7103	0.2710	0.3556	0.067*
C3	0.5644 (2)	0.3918 (2)	0.3605 (2)	0.0694 (7)
H3	0.5552	0.3717	0.4294	0.083*
C4	0.4849 (3)	0.4804 (2)	0.3038 (2)	0.0738 (7)
H4	0.4200	0.5192	0.3332	0.089*
C5	0.5005 (3)	0.51236 (19)	0.2034 (2)	0.0732 (7)
H5	0.4467	0.5731	0.1652	0.088*
C6	0.5951 (2)	0.45494 (17)	0.15921 (18)	0.0568 (5)
H6	0.6070	0.4772	0.0918	0.068*
C7	1.0474 (2)	0.29629 (15)	0.33830 (14)	0.0424 (4)
H7	0.9836	0.2401	0.3570	0.051*
C8	1.0716 (2)	0.38752 (18)	0.42469 (16)	0.0568 (5)
H8A	0.9739	0.4194	0.4203	0.068*
H8B	1.1338	0.4452	0.4084	0.068*
C9	1.1495 (2)	0.3434 (2)	0.54232 (16)	0.0632 (6)
H9A	1.1678	0.4037	0.5958	0.076*
H9B	1.0829	0.2907	0.5610	0.076*
C10	1.2988 (2)	0.2885 (2)	0.55192 (17)	0.0651 (6)
H10A	1.3416	0.2563	0.6262	0.078*
H10B	1.3701	0.3434	0.5430	0.078*
C11	1.2786 (3)	0.1995 (2)	0.46425 (18)	0.0679 (7)
H11A	1.2203	0.1392	0.4805	0.082*
H11B	1.3780	0.1710	0.4682	0.082*
C12	1.1976 (2)	0.24159 (18)	0.34615 (16)	0.0546 (5)
H12A	1.1787	0.1805	0.2936	0.065*
H12B	1.2625	0.2943	0.3255	0.065*
C13	1.0145 (3)	0.4353 (2)	0.18252 (19)	0.0719 (7)
H13A	0.9857	0.4965	0.2197	0.108*
H13B	0.9659	0.4421	0.1027	0.108*
H13C	1.1233	0.4350	0.1996	0.108*
N1	0.96659 (17)	0.33232 (13)	0.22141 (13)	0.0485 (4)
O1	0.78750 (17)	0.17730 (12)	0.18902 (14)	0.0710 (5)
O2	0.75416 (18)	0.32058 (15)	0.04381 (11)	0.0769 (5)
S1	0.79429 (6)	0.29004 (4)	0.15969 (4)	0.0523 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0369 (9)	0.0421 (11)	0.0442 (10)	−0.0061 (8)	0.0002 (7)	−0.0009 (8)
C2	0.0458 (11)	0.0601 (14)	0.0563 (12)	−0.0031 (10)	0.0104 (9)	0.0119 (10)
C3	0.0505 (12)	0.0910 (19)	0.0690 (15)	−0.0087 (13)	0.0227 (11)	−0.0028 (13)
C4	0.0447 (12)	0.0776 (18)	0.098 (2)	−0.0046 (12)	0.0213 (13)	−0.0252 (15)
C5	0.0569 (14)	0.0515 (14)	0.098 (2)	0.0069 (11)	0.0078 (13)	0.0027 (13)
C6	0.0513 (12)	0.0506 (13)	0.0579 (12)	0.0002 (10)	0.0033 (10)	0.0078 (10)
C7	0.0397 (10)	0.0442 (11)	0.0410 (10)	−0.0014 (8)	0.0101 (8)	0.0003 (8)
C8	0.0558 (12)	0.0591 (13)	0.0535 (12)	0.0128 (10)	0.0151 (9)	−0.0100 (10)
C9	0.0655 (14)	0.0758 (16)	0.0468 (12)	0.0075 (11)	0.0163 (10)	−0.0124 (10)
C10	0.0573 (13)	0.0805 (17)	0.0477 (12)	0.0090 (11)	0.0039 (10)	−0.0097 (11)
C11	0.0618 (14)	0.0700 (16)	0.0583 (13)	0.0212 (11)	0.0009 (10)	−0.0093 (11)
C12	0.0519 (12)	0.0567 (13)	0.0507 (12)	0.0091 (9)	0.0108 (9)	−0.0131 (9)
C13	0.0738 (15)	0.0693 (16)	0.0675 (15)	−0.0071 (12)	0.0162 (12)	0.0176 (12)
N1	0.0454 (9)	0.0507 (10)	0.0462 (9)	−0.0010 (7)	0.0108 (7)	0.0024 (7)
O1	0.0658 (10)	0.0425 (9)	0.0905 (11)	−0.0052 (7)	0.0064 (8)	−0.0131 (8)
O2	0.0797 (11)	0.1027 (13)	0.0379 (8)	0.0063 (9)	0.0050 (7)	−0.0119 (8)
S1	0.0513 (3)	0.0512 (3)	0.0449 (3)	−0.0004 (2)	0.0027 (2)	−0.0090 (2)

C1—C6	1.378 (3)	C9—C10	1.505 (3)
C1—C2	1.385 (3)	C9—H9A	0.9700
C1—S1	1.760 (2)	C9—H9B	0.9700
C2—C3	1.369 (3)	C10—C11	1.509 (3)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.364 (3)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.517 (3)
C4—C5	1.374 (4)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.372 (3)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—H6	0.9300	C13—N1	1.462 (3)
C7—N1	1.481 (2)	C13—H13A	0.9600
C7—C8	1.515 (3)	C13—H13B	0.9600
C7—C12	1.516 (3)	C13—H13C	0.9600
C7—H7	0.9800	N1—S1	1.6144 (16)
C8—C9	1.516 (3)	O1—S1	1.4218 (16)
C8—H8A	0.9700	O2—S1	1.4302 (15)
C8—H8B	0.9700
C6—C1—C2	120.5 (2)	H9A—C9—H9B	108.0
C6—C1—S1	119.68 (16)	C9—C10—C11	111.51 (18)
C2—C1—S1	119.84 (15)	C9—C10—H10A	109.3
C3—C2—C1	119.1 (2)	C11—C10—H10A	109.3
C3—C2—H2	120.5	C9—C10—H10B	109.3
C1—C2—H2	120.5	C11—C10—H10B	109.3
C4—C3—C2	120.8 (2)	H10A—C10—H10B	108.0
C4—C3—H3	119.6	C10—C11—C12	112.27 (18)
C2—C3—H3	119.6	C10—C11—H11A	109.2
C3—C4—C5	120.1 (2)	C12—C11—H11A	109.1
C3—C4—H4	120.0	C10—C11—H11B	109.1
C5—C4—H4	120.0	C12—C11—H11B	109.1
C6—C5—C4	120.2 (2)	H11A—C11—H11B	107.9
C6—C5—H5	119.9	C11—C12—C7	111.14 (17)
C4—C5—H5	119.9	C11—C12—H12A	109.4
C5—C6—C1	119.4 (2)	C7—C12—H12A	109.4
C5—C6—H6	120.3	C11—C12—H12B	109.4
C1—C6—H6	120.3	C7—C12—H12B	109.4
N1—C7—C8	113.90 (15)	H12A—C12—H12B	108.0
N1—C7—C12	110.43 (15)	N1—C13—H13A	109.5
C8—C7—C12	110.80 (15)	N1—C13—H13B	109.5
N1—C7—H7	107.1	H13A—C13—H13B	109.5
C8—C7—H7	107.1	N1—C13—H13C	109.5
C12—C7—H7	107.1	H13A—C13—H13C	109.5
C7—C8—C9	110.76 (17)	H13B—C13—H13C	109.5
C7—C8—H8A	109.5	C13—N1—C7	118.27 (15)
C9—C8—H8A	109.5	C13—N1—S1	118.12 (13)
C7—C8—H8B	109.5	C7—N1—S1	118.92 (12)
C9—C8—H8B	109.5	O1—S1—O2	119.63 (10)
H8A—C8—H8B	108.1	O1—S1—N1	107.52 (9)
C10—C9—C8	111.50 (17)	O2—S1—N1	107.13 (10)
C10—C9—H9A	109.3	O1—S1—C1	107.27 (10)
C8—C9—H9A	109.3	O2—S1—C1	106.79 (9)
C10—C9—H9B	109.3	N1—S1—C1	108.06 (8)
C8—C9—H9B	109.3

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.52	3.268 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.52	3.268 (3)	137

Symmetry code: (i) .