N-Benzyl-N-cyclo-hexyl-4-methyl-benzene-sulfonamide.

In the title compound, C(20)H(25)NO(2)S, the cyclo-hexyl ring exists in a chair form and the mean plane through all six atoms makes dihedral angles of 56.12 (9) and 55.19 (10)° with the benzene and phenyl rings, respectively. The dihedral angle between the two aromatic rings is 77.23 (7)°. A weak intra-molecular C-H⋯O interaction occurs.

Related literature

For the biological activity of sulfonamides, see: 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

C20H25NO2S

M = 343.47

Orthorhombic,

a = 9.0702 (4) Å

b = 11.1054 (5) Å

c = 18.1971 (8) Å

V = 1832.96 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.24 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.976

11619 measured reflections

4493 independent reflections

2764 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.097

S = 0.98

4493 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1915 Friedel pairs

Flack parameter: 0.04 (8)

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: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809048193/is2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048193/is2488Isup2.hkl

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

C20H25NO2S	F(000) = 736
Mr = 343.47	Dx = 1.245 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2246 reflections
a = 9.0702 (4) Å	θ = 2.9–20.7°
b = 11.1054 (5) Å	µ = 0.19 mm−1
c = 18.1971 (8) Å	T = 296 K
V = 1832.96 (14) Å3	Blocks, yellow
Z = 4	0.24 × 0.18 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	4493 independent reflections
Radiation source: fine-focus sealed tube	2764 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.956, Tmax = 0.976	k = −14→7
11619 measured reflections	l = −24→22

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0397P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
4493 reflections	Δρmax = 0.16 e Å−3
218 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 1915 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (8)

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
S1	0.13668 (7)	0.35270 (6)	0.83512 (3)	0.04431 (17)
O1	0.0611 (2)	0.45762 (15)	0.86060 (9)	0.0603 (5)
O2	0.28860 (18)	0.36124 (17)	0.81433 (9)	0.0604 (5)
N1	0.04730 (19)	0.30283 (17)	0.76418 (9)	0.0396 (5)
C1	0.1256 (3)	0.2456 (2)	0.90607 (11)	0.0386 (5)
C2	0.2185 (3)	0.1481 (2)	0.90729 (13)	0.0520 (6)
H2	0.2872	0.1375	0.8699	0.062*
C3	0.2102 (3)	0.0660 (2)	0.96364 (14)	0.0556 (7)
H3	0.2729	−0.0002	0.9632	0.067*
C4	0.1123 (3)	0.0789 (2)	1.02044 (13)	0.0492 (6)
C5	0.0189 (3)	0.1763 (3)	1.01803 (13)	0.0634 (8)
H5	−0.0498	0.1867	1.0554	0.076*
C6	0.0247 (3)	0.2591 (3)	0.96159 (13)	0.0607 (8)
H6	−0.0399	0.3241	0.9612	0.073*
C7	−0.1161 (2)	0.3031 (2)	0.76700 (11)	0.0404 (6)
H7	−0.1444	0.3559	0.8078	0.049*
C8	−0.1825 (2)	0.1808 (2)	0.78275 (15)	0.0573 (7)
H8A	−0.1451	0.1507	0.8292	0.069*
H8B	−0.1539	0.1246	0.7445	0.069*
C9	−0.3505 (3)	0.1892 (3)	0.78615 (16)	0.0700 (8)
H9A	−0.3916	0.1094	0.7933	0.084*
H9B	−0.3790	0.2385	0.8278	0.084*
C10	−0.4124 (3)	0.2434 (3)	0.71630 (16)	0.0723 (9)
H10A	−0.3913	0.1904	0.6752	0.087*
H10B	−0.5186	0.2508	0.7207	0.087*
C11	−0.3468 (3)	0.3647 (3)	0.70192 (14)	0.0630 (8)
H11A	−0.3752	0.4195	0.7409	0.076*
H11B	−0.3852	0.3961	0.6560	0.076*
C12	−0.1796 (2)	0.3582 (3)	0.69771 (13)	0.0556 (7)
H12A	−0.1509	0.3100	0.6556	0.067*
H12B	−0.1398	0.4385	0.6911	0.067*
C13	0.1222 (3)	0.2229 (2)	0.71193 (11)	0.0423 (6)
H13A	0.0613	0.1522	0.7043	0.051*
H13B	0.2143	0.1964	0.7336	0.051*
C14	0.1544 (2)	0.2793 (2)	0.63832 (12)	0.0412 (6)
C15	0.2396 (3)	0.3820 (2)	0.63277 (14)	0.0582 (8)
H15	0.2745	0.4194	0.6751	0.070*
C16	0.2731 (3)	0.4293 (3)	0.56453 (18)	0.0753 (9)
H16	0.3311	0.4981	0.5614	0.090*
C17	0.2222 (4)	0.3763 (3)	0.50164 (17)	0.0773 (10)
H17	0.2457	0.4082	0.4559	0.093*
C18	0.1365 (4)	0.2759 (3)	0.50727 (15)	0.0756 (9)
H18	0.1007	0.2393	0.4649	0.091*
C19	0.1022 (3)	0.2279 (2)	0.57493 (14)	0.0572 (7)
H19	0.0430	0.1597	0.5777	0.069*
C20	0.1098 (3)	−0.0076 (3)	1.08385 (14)	0.0736 (9)
H20A	0.0270	0.0100	1.1149	0.110*
H20B	0.1993	0.0003	1.1116	0.110*
H20C	0.1015	−0.0884	1.0656	0.110*

	U11	U22	U33	U12	U13	U23
S1	0.0498 (4)	0.0418 (3)	0.0414 (3)	−0.0050 (3)	−0.0074 (3)	−0.0030 (3)
O1	0.0852 (13)	0.0385 (10)	0.0573 (12)	0.0057 (9)	−0.0130 (9)	−0.0102 (9)
O2	0.0487 (10)	0.0769 (14)	0.0555 (11)	−0.0207 (10)	−0.0072 (8)	0.0060 (10)
N1	0.0385 (11)	0.0467 (13)	0.0337 (11)	0.0014 (9)	−0.0024 (8)	−0.0059 (9)
C1	0.0404 (13)	0.0399 (14)	0.0353 (12)	−0.0011 (12)	−0.0071 (11)	−0.0064 (10)
C2	0.0575 (15)	0.0552 (16)	0.0432 (15)	0.0053 (15)	0.0086 (11)	−0.0058 (15)
C3	0.0648 (17)	0.0481 (17)	0.0538 (17)	0.0098 (14)	−0.0022 (14)	−0.0005 (14)
C4	0.0535 (17)	0.0530 (17)	0.0413 (14)	−0.0061 (14)	−0.0065 (13)	0.0013 (12)
C5	0.0583 (17)	0.089 (3)	0.0429 (16)	0.0123 (17)	0.0101 (12)	0.0069 (16)
C6	0.0546 (17)	0.078 (2)	0.0499 (16)	0.0238 (15)	0.0055 (13)	0.0068 (15)
C7	0.0394 (14)	0.0433 (14)	0.0385 (12)	0.0043 (11)	0.0007 (11)	−0.0047 (10)
C8	0.0416 (16)	0.0557 (19)	0.0747 (19)	−0.0022 (12)	0.0023 (12)	0.0114 (15)
C9	0.0506 (16)	0.070 (2)	0.089 (2)	−0.0053 (15)	0.0082 (16)	0.0075 (17)
C10	0.0379 (16)	0.104 (3)	0.075 (2)	0.0028 (16)	−0.0055 (13)	−0.010 (2)
C11	0.0489 (16)	0.084 (2)	0.0561 (16)	0.0138 (17)	−0.0051 (12)	0.0061 (17)
C12	0.0495 (16)	0.0620 (18)	0.0552 (16)	0.0061 (14)	−0.0051 (11)	0.0098 (16)
C13	0.0404 (13)	0.0429 (15)	0.0437 (14)	0.0034 (12)	0.0023 (11)	−0.0019 (11)
C14	0.0426 (14)	0.0415 (15)	0.0396 (13)	0.0057 (12)	0.0020 (11)	−0.0025 (11)
C15	0.0599 (18)	0.062 (2)	0.0528 (16)	−0.0095 (15)	−0.0029 (13)	0.0043 (14)
C16	0.073 (2)	0.078 (2)	0.075 (2)	−0.0156 (18)	0.0113 (18)	0.022 (2)
C17	0.094 (2)	0.090 (3)	0.0482 (19)	0.011 (2)	0.0187 (16)	0.0196 (19)
C18	0.102 (2)	0.079 (2)	0.0459 (17)	0.015 (2)	0.0012 (18)	−0.0021 (16)
C19	0.0699 (19)	0.0531 (18)	0.0486 (16)	0.0012 (14)	0.0012 (13)	−0.0011 (14)
C20	0.093 (2)	0.066 (2)	0.0620 (18)	−0.0067 (18)	−0.0045 (16)	0.0123 (16)

S1—O1	1.4291 (17)	C10—C11	1.495 (4)
S1—O2	1.4321 (17)	C10—H10A	0.9700
S1—N1	1.6219 (18)	C10—H10B	0.9700
S1—C1	1.758 (2)	C11—C12	1.520 (3)
N1—C13	1.467 (3)	C11—H11A	0.9700
N1—C7	1.483 (3)	C11—H11B	0.9700
C1—C6	1.371 (3)	C12—H12A	0.9700
C1—C2	1.372 (3)	C12—H12B	0.9700
C2—C3	1.374 (3)	C13—C14	1.507 (3)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.370 (3)	C13—H13B	0.9700
C3—H3	0.9300	C14—C19	1.372 (3)
C4—C5	1.374 (3)	C14—C15	1.381 (3)
C4—C20	1.502 (3)	C15—C16	1.382 (4)
C5—C6	1.379 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.367 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.513 (3)	C17—C18	1.364 (4)
C7—C12	1.515 (3)	C17—H17	0.9300
C7—H7	0.9800	C18—C19	1.377 (4)
C8—C9	1.528 (3)	C18—H18	0.9300
C8—H8A	0.9700	C19—H19	0.9300
C8—H8B	0.9700	C20—H20A	0.9600
C9—C10	1.514 (4)	C20—H20B	0.9600
C9—H9A	0.9700	C20—H20C	0.9600
C9—H9B	0.9700
O1—S1—O2	119.55 (12)	C9—C10—H10A	109.5
O1—S1—N1	107.27 (10)	C11—C10—H10B	109.5
O2—S1—N1	107.05 (10)	C9—C10—H10B	109.5
O1—S1—C1	106.61 (10)	H10A—C10—H10B	108.0
O2—S1—C1	107.08 (11)	C10—C11—C12	111.3 (2)
N1—S1—C1	108.96 (10)	C10—C11—H11A	109.4
C13—N1—C7	119.09 (18)	C12—C11—H11A	109.4
C13—N1—S1	119.41 (15)	C10—C11—H11B	109.4
C7—N1—S1	118.11 (14)	C12—C11—H11B	109.4
C6—C1—C2	118.9 (2)	H11A—C11—H11B	108.0
C6—C1—S1	120.3 (2)	C7—C12—C11	110.9 (2)
C2—C1—S1	120.71 (18)	C7—C12—H12A	109.5
C1—C2—C3	120.1 (2)	C11—C12—H12A	109.5
C1—C2—H2	119.9	C7—C12—H12B	109.5
C3—C2—H2	119.9	C11—C12—H12B	109.5
C4—C3—C2	121.9 (2)	H12A—C12—H12B	108.1
C4—C3—H3	119.0	N1—C13—C14	114.46 (18)
C2—C3—H3	119.0	N1—C13—H13A	108.6
C3—C4—C5	117.2 (2)	C14—C13—H13A	108.6
C3—C4—C20	121.5 (3)	N1—C13—H13B	108.6
C5—C4—C20	121.3 (2)	C14—C13—H13B	108.6
C4—C5—C6	121.7 (2)	H13A—C13—H13B	107.6
C4—C5—H5	119.2	C19—C14—C15	118.4 (2)
C6—C5—H5	119.2	C19—C14—C13	120.5 (2)
C1—C6—C5	120.1 (3)	C15—C14—C13	121.1 (2)
C1—C6—H6	120.0	C14—C15—C16	120.2 (3)
C5—C6—H6	120.0	C14—C15—H15	119.9
N1—C7—C8	113.73 (19)	C16—C15—H15	119.9
N1—C7—C12	110.59 (18)	C17—C16—C15	121.0 (3)
C8—C7—C12	111.7 (2)	C17—C16—H16	119.5
N1—C7—H7	106.8	C15—C16—H16	119.5
C8—C7—H7	106.8	C18—C17—C16	118.8 (3)
C12—C7—H7	106.8	C18—C17—H17	120.6
C7—C8—C9	110.4 (2)	C16—C17—H17	120.6
C7—C8—H8A	109.6	C17—C18—C19	120.8 (3)
C9—C8—H8A	109.6	C17—C18—H18	119.6
C7—C8—H8B	109.6	C19—C18—H18	119.6
C9—C8—H8B	109.6	C14—C19—C18	120.9 (3)
H8A—C8—H8B	108.1	C14—C19—H19	119.6
C10—C9—C8	111.1 (2)	C18—C19—H19	119.6
C10—C9—H9A	109.4	C4—C20—H20A	109.5
C8—C9—H9A	109.4	C4—C20—H20B	109.5
C10—C9—H9B	109.4	H20A—C20—H20B	109.5
C8—C9—H9B	109.4	C4—C20—H20C	109.5
H9A—C9—H9B	108.0	H20A—C20—H20C	109.5
C11—C10—C9	110.9 (2)	H20B—C20—H20C	109.5
C11—C10—H10A	109.5
O1—S1—N1—C13	159.58 (16)	S1—N1—C7—C8	−101.8 (2)
O2—S1—N1—C13	30.12 (19)	C13—N1—C7—C12	−69.2 (3)
C1—S1—N1—C13	−85.37 (18)	S1—N1—C7—C12	131.65 (18)
O1—S1—N1—C7	−41.37 (19)	N1—C7—C8—C9	178.9 (2)
O2—S1—N1—C7	−170.83 (17)	C12—C7—C8—C9	−55.1 (3)
C1—S1—N1—C7	73.68 (19)	C7—C8—C9—C10	55.6 (3)
O1—S1—C1—C6	16.6 (2)	C8—C9—C10—C11	−56.8 (3)
O2—S1—C1—C6	145.7 (2)	C9—C10—C11—C12	56.8 (3)
N1—S1—C1—C6	−98.9 (2)	N1—C7—C12—C11	−177.1 (2)
O1—S1—C1—C2	−162.71 (19)	C8—C7—C12—C11	55.2 (3)
O2—S1—C1—C2	−33.6 (2)	C10—C11—C12—C7	−56.0 (3)
N1—S1—C1—C2	81.8 (2)	C7—N1—C13—C14	91.6 (2)
C6—C1—C2—C3	−0.3 (4)	S1—N1—C13—C14	−109.5 (2)
S1—C1—C2—C3	179.01 (18)	N1—C13—C14—C19	−123.0 (2)
C1—C2—C3—C4	−1.0 (4)	N1—C13—C14—C15	58.5 (3)
C2—C3—C4—C5	1.6 (4)	C19—C14—C15—C16	−1.3 (4)
C2—C3—C4—C20	−176.6 (2)	C13—C14—C15—C16	177.2 (2)
C3—C4—C5—C6	−1.0 (4)	C14—C15—C16—C17	0.4 (5)
C20—C4—C5—C6	177.2 (3)	C15—C16—C17—C18	0.4 (5)
C2—C1—C6—C5	0.9 (4)	C16—C17—C18—C19	−0.4 (5)
S1—C1—C6—C5	−178.4 (2)	C15—C14—C19—C18	1.3 (4)
C4—C5—C6—C1	−0.2 (4)	C13—C14—C19—C18	−177.2 (3)
C13—N1—C7—C8	57.3 (3)	C17—C18—C19—C14	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.38	2.903 (3)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.98	2.38	2.903 (3)	113