N-Benzyl-N-cyclo-hexyl-benzene-sulfonamide.

In the title compound, C(19)H(23)NO(2)S, the cyclo-hexyl ring exists in a chair form. The dihedral angle between the two terminal phenyl rings is 86.70 (6)°. No significant inter-actions are observed except for a weak intra-molecular C-H⋯O hydrogen bond.

Related literature

For the biological activity of sulfonamides, see: Innocenti et al. (2004 ▶); Ozbek et al. (2007 ▶); Parari et al. (2008 ▶); Ratish et al. (2009 ▶); Selnam et al. (2001 ▶); For related structures, see: Khan et al. (2009 ▶); Zia-ur-Rehman et al. (2009 ▶) Gowda et al. (2007a ▶,b ▶,c ▶). For bond length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H23NO2S

M = 329.44

Orthorhombic,

a = 9.1996 (5) Å

b = 11.0406 (5) Å

c = 17.1897 (9) Å

V = 1745.94 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.39 × 0.34 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.928, T max = 0.948

10897 measured reflections

4306 independent reflections

3507 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.03

4306 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1853 Friedel pairs

Flack parameter: 0.03 (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: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046960/is2484sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046960/is2484Isup2.hkl

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

C19H23NO2S	F(000) = 704
Mr = 329.44	Dx = 1.253 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3979 reflections
a = 9.1996 (5) Å	θ = 2.3–21.8°
b = 11.0406 (5) Å	µ = 0.20 mm−1
c = 17.1897 (9) Å	T = 296 K
V = 1745.94 (15) Å3	Blocks, colourless
Z = 4	0.39 × 0.34 × 0.28 mm

Bruker APEXII CCD area-detector diffractometer	4306 independent reflections
Radiation source: fine-focus sealed tube	3507 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.928, Tmax = 0.948	k = −11→14
10897 measured reflections	l = −22→17

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-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.049P)2 + 0.1094P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4306 reflections	Δρmax = 0.24 e Å−3
208 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 1853 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (7)

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	0.3444 (2)	0.27298 (15)	0.91369 (9)	0.0423 (4)
C2	0.4528 (2)	0.2866 (2)	0.96899 (11)	0.0596 (5)
H2	0.5302	0.2325	0.9709	0.072*
C3	0.4447 (3)	0.3813 (2)	1.02106 (13)	0.0737 (7)
H3	0.5170	0.3910	1.0583	0.088*
C4	0.3305 (3)	0.4615 (2)	1.01838 (13)	0.0720 (7)
H4	0.3252	0.5250	1.0539	0.086*
C5	0.2244 (3)	0.4475 (2)	0.96314 (14)	0.0676 (6)
H5	0.1478	0.5023	0.9611	0.081*
C6	0.2295 (2)	0.3532 (2)	0.91061 (11)	0.0542 (5)
H6	0.1566	0.3438	0.8736	0.065*
C7	0.61067 (18)	0.20568 (15)	0.77713 (10)	0.0396 (4)
H7	0.6361	0.1620	0.8249	0.048*
C8	0.6733 (2)	0.33204 (18)	0.78485 (14)	0.0587 (5)
H8A	0.6285	0.3732	0.8286	0.070*
H8B	0.6528	0.3782	0.7381	0.070*
C9	0.8375 (2)	0.3243 (2)	0.79731 (14)	0.0647 (6)
H9A	0.8777	0.4054	0.8002	0.078*
H9B	0.8572	0.2838	0.8463	0.078*
C10	0.9099 (2)	0.2560 (2)	0.73209 (13)	0.0653 (6)
H10A	0.8985	0.3008	0.6839	0.078*
H10B	1.0131	0.2489	0.7428	0.078*
C11	0.8458 (2)	0.1321 (2)	0.72278 (14)	0.0717 (6)
H11A	0.8666	0.0845	0.7689	0.086*
H11B	0.8908	0.0922	0.6787	0.086*
C12	0.6807 (2)	0.13740 (19)	0.71029 (12)	0.0574 (5)
H12A	0.6593	0.1780	0.6616	0.069*
H12B	0.6416	0.0559	0.7077	0.069*
C13	0.3750 (2)	0.28365 (15)	0.71472 (9)	0.0407 (4)
H13A	0.4319	0.3571	0.7088	0.049*
H13B	0.2811	0.3064	0.7358	0.049*
C14	0.35265 (19)	0.22767 (13)	0.63549 (9)	0.0385 (3)
C15	0.2610 (2)	0.12964 (17)	0.62532 (12)	0.0556 (5)
H15	0.2141	0.0962	0.6681	0.067*
C16	0.2385 (3)	0.0808 (2)	0.55228 (14)	0.0647 (6)
H16	0.1760	0.0153	0.5463	0.078*
C17	0.3074 (3)	0.1283 (2)	0.48873 (12)	0.0646 (6)
H17	0.2917	0.0955	0.4396	0.077*
C18	0.4001 (3)	0.2249 (2)	0.49795 (12)	0.0668 (6)
H18	0.4484	0.2568	0.4551	0.080*
C19	0.4216 (2)	0.27463 (17)	0.57071 (11)	0.0535 (5)
H19	0.4833	0.3407	0.5762	0.064*
N1	0.44909 (16)	0.20318 (12)	0.77103 (8)	0.0402 (3)
O1	0.21214 (15)	0.12969 (13)	0.81853 (8)	0.0590 (4)
O2	0.43915 (17)	0.05891 (11)	0.88027 (8)	0.0592 (4)
S1	0.35656 (5)	0.15399 (4)	0.84502 (2)	0.04355 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0453 (9)	0.0462 (9)	0.0352 (8)	−0.0024 (8)	0.0063 (8)	0.0056 (7)
C2	0.0564 (12)	0.0720 (13)	0.0504 (11)	0.0075 (11)	−0.0061 (10)	0.0019 (10)
C3	0.0780 (16)	0.0892 (17)	0.0539 (12)	−0.0098 (14)	−0.0089 (12)	−0.0100 (12)
C4	0.0928 (19)	0.0669 (13)	0.0564 (12)	−0.0073 (14)	0.0093 (14)	−0.0126 (11)
C5	0.0761 (15)	0.0617 (13)	0.0651 (14)	0.0124 (12)	0.0139 (12)	−0.0008 (11)
C6	0.0508 (11)	0.0621 (11)	0.0495 (10)	0.0073 (10)	0.0009 (8)	0.0008 (10)
C7	0.0378 (9)	0.0447 (9)	0.0364 (8)	0.0043 (7)	−0.0017 (7)	0.0039 (7)
C8	0.0437 (11)	0.0513 (10)	0.0812 (14)	0.0000 (9)	0.0033 (10)	−0.0147 (10)
C9	0.0432 (11)	0.0695 (13)	0.0815 (14)	−0.0033 (10)	−0.0042 (10)	−0.0146 (12)
C10	0.0351 (10)	0.0957 (17)	0.0651 (13)	0.0074 (11)	−0.0003 (9)	−0.0016 (13)
C11	0.0513 (12)	0.0869 (16)	0.0768 (14)	0.0229 (13)	0.0006 (11)	−0.0247 (13)
C12	0.0501 (11)	0.0611 (11)	0.0610 (12)	0.0101 (9)	−0.0006 (9)	−0.0166 (10)
C13	0.0418 (9)	0.0388 (8)	0.0416 (9)	0.0036 (7)	−0.0034 (7)	0.0009 (7)
C14	0.0357 (8)	0.0376 (7)	0.0423 (8)	0.0045 (7)	−0.0080 (7)	0.0032 (6)
C15	0.0549 (11)	0.0551 (11)	0.0570 (11)	−0.0136 (10)	−0.0014 (9)	0.0008 (9)
C16	0.0671 (14)	0.0558 (11)	0.0712 (14)	−0.0153 (11)	−0.0111 (11)	−0.0097 (11)
C17	0.0855 (16)	0.0613 (12)	0.0469 (11)	0.0000 (11)	−0.0204 (11)	−0.0056 (10)
C18	0.0957 (18)	0.0657 (14)	0.0390 (10)	−0.0094 (13)	−0.0041 (10)	0.0078 (10)
C19	0.0662 (13)	0.0471 (10)	0.0472 (11)	−0.0115 (10)	−0.0069 (9)	0.0067 (9)
N1	0.0387 (8)	0.0455 (8)	0.0365 (7)	0.0043 (6)	−0.0002 (6)	0.0043 (6)
O1	0.0469 (7)	0.0690 (9)	0.0610 (8)	−0.0151 (7)	0.0052 (6)	−0.0039 (7)
O2	0.0711 (9)	0.0436 (7)	0.0629 (8)	0.0059 (7)	0.0071 (7)	0.0168 (6)
S1	0.0449 (2)	0.0415 (2)	0.0442 (2)	−0.0025 (2)	0.0035 (2)	0.00529 (19)

C1—C6	1.380 (3)	C10—H10B	0.9700
C1—C2	1.386 (3)	C11—C12	1.535 (3)
C1—S1	1.7696 (18)	C11—H11A	0.9700
C2—C3	1.378 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.375 (3)	C12—H12B	0.9700
C3—H3	0.9300	C13—N1	1.480 (2)
C4—C5	1.370 (3)	C13—C14	1.510 (2)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.379 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C19	1.382 (2)
C6—H6	0.9300	C14—C15	1.383 (2)
C7—N1	1.490 (2)	C15—C16	1.382 (3)
C7—C8	1.515 (3)	C15—H15	0.9300
C7—C12	1.518 (2)	C16—C17	1.368 (3)
C7—H7	0.9800	C16—H16	0.9300
C8—C9	1.528 (3)	C17—C18	1.374 (3)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.380 (3)
C9—C10	1.506 (3)	C18—H18	0.9300
C9—H9A	0.9700	C19—H19	0.9300
C9—H9B	0.9700	N1—S1	1.6240 (14)
C10—C11	1.498 (3)	O1—S1	1.4299 (14)
C10—H10A	0.9700	O2—S1	1.4305 (14)
C6—C1—C2	120.51 (18)	C12—C11—H11A	109.3
C6—C1—S1	119.94 (14)	C10—C11—H11B	109.3
C2—C1—S1	119.54 (15)	C12—C11—H11B	109.3
C3—C2—C1	119.3 (2)	H11A—C11—H11B	107.9
C3—C2—H2	120.4	C7—C12—C11	109.44 (16)
C1—C2—H2	120.4	C7—C12—H12A	109.8
C4—C3—C2	120.6 (2)	C11—C12—H12A	109.8
C4—C3—H3	119.7	C7—C12—H12B	109.8
C2—C3—H3	119.7	C11—C12—H12B	109.8
C5—C4—C3	119.6 (2)	H12A—C12—H12B	108.2
C5—C4—H4	120.2	N1—C13—C14	114.01 (13)
C3—C4—H4	120.2	N1—C13—H13A	108.7
C4—C5—C6	121.0 (2)	C14—C13—H13A	108.7
C4—C5—H5	119.5	N1—C13—H13B	108.7
C6—C5—H5	119.5	C14—C13—H13B	108.7
C5—C6—C1	119.05 (19)	H13A—C13—H13B	107.6
C5—C6—H6	120.5	C19—C14—C15	118.11 (16)
C1—C6—H6	120.5	C19—C14—C13	120.72 (15)
N1—C7—C8	113.74 (14)	C15—C14—C13	121.17 (16)
N1—C7—C12	111.15 (15)	C16—C15—C14	120.77 (19)
C8—C7—C12	111.24 (15)	C16—C15—H15	119.6
N1—C7—H7	106.8	C14—C15—H15	119.6
C8—C7—H7	106.8	C17—C16—C15	120.4 (2)
C12—C7—H7	106.8	C17—C16—H16	119.8
C7—C8—C9	109.69 (17)	C15—C16—H16	119.8
C7—C8—H8A	109.7	C16—C17—C18	119.5 (2)
C9—C8—H8A	109.7	C16—C17—H17	120.2
C7—C8—H8B	109.7	C18—C17—H17	120.2
C9—C8—H8B	109.7	C17—C18—C19	120.1 (2)
H8A—C8—H8B	108.2	C17—C18—H18	119.9
C10—C9—C8	111.14 (18)	C19—C18—H18	119.9
C10—C9—H9A	109.4	C18—C19—C14	121.02 (18)
C8—C9—H9A	109.4	C18—C19—H19	119.5
C10—C9—H9B	109.4	C14—C19—H19	119.5
C8—C9—H9B	109.4	C13—N1—C7	119.61 (14)
H9A—C9—H9B	108.0	C13—N1—S1	118.13 (12)
C11—C10—C9	111.26 (19)	C7—N1—S1	118.29 (11)
C11—C10—H10A	109.4	O1—S1—O2	119.39 (9)
C9—C10—H10A	109.4	O1—S1—N1	107.48 (8)
C11—C10—H10B	109.4	O2—S1—N1	107.38 (8)
C9—C10—H10B	109.4	O1—S1—C1	107.04 (9)
H10A—C10—H10B	108.0	O2—S1—C1	107.20 (8)
C10—C11—C12	111.71 (18)	N1—S1—C1	107.90 (7)
C10—C11—H11A	109.3
C6—C1—C2—C3	0.1 (3)	C16—C17—C18—C19	−1.0 (4)
S1—C1—C2—C3	178.36 (17)	C17—C18—C19—C14	1.0 (3)
C1—C2—C3—C4	0.0 (3)	C15—C14—C19—C18	−0.2 (3)
C2—C3—C4—C5	−0.4 (4)	C13—C14—C19—C18	−179.12 (19)
C3—C4—C5—C6	0.7 (4)	C14—C13—N1—C7	90.42 (18)
C4—C5—C6—C1	−0.6 (3)	C14—C13—N1—S1	−112.35 (15)
C2—C1—C6—C5	0.3 (3)	C8—C7—N1—C13	49.3 (2)
S1—C1—C6—C5	−178.03 (16)	C12—C7—N1—C13	−77.18 (18)
N1—C7—C8—C9	175.43 (16)	C8—C7—N1—S1	−107.91 (16)
C12—C7—C8—C9	−58.1 (2)	C12—C7—N1—S1	125.63 (14)
C7—C8—C9—C10	56.9 (2)	C13—N1—S1—O1	37.74 (14)
C8—C9—C10—C11	−56.2 (3)	C7—N1—S1—O1	−164.73 (12)
C9—C10—C11—C12	55.8 (3)	C13—N1—S1—O2	167.36 (12)
N1—C7—C12—C11	−174.82 (17)	C7—N1—S1—O2	−35.11 (15)
C8—C7—C12—C11	57.3 (2)	C13—N1—S1—C1	−77.38 (14)
C10—C11—C12—C7	−56.0 (3)	C7—N1—S1—C1	80.15 (14)
N1—C13—C14—C19	−115.08 (18)	C6—C1—S1—O1	−25.17 (17)
N1—C13—C14—C15	66.1 (2)	C2—C1—S1—O1	156.51 (15)
C19—C14—C15—C16	−0.5 (3)	C6—C1—S1—O2	−154.38 (14)
C13—C14—C15—C16	178.40 (19)	C2—C1—S1—O2	27.30 (17)
C14—C15—C16—C17	0.5 (3)	C6—C1—S1—N1	90.25 (16)
C15—C16—C17—C18	0.3 (4)	C2—C1—S1—N1	−88.07 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.98	2.34	2.874 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2	0.98	2.34	2.874 (2)	113