N-Cyclo-hexyl-N-ethyl-4-methyl-benzene-sulfonamide.

The title compound, C(15)H(23)NO(2)S, contains cyclo-hexyl and ethyl substituents on the sulfonamide N atom and the cyclo-hexyl ring adopts a classic chair conformation. The dihedral angle between the benzene ring plane and the mean plane through the six atoms of the cyclo-hexyl ring is 59.92 (6)°. In the crystal structure, C-H⋯O hydrogen bonds link mol-ecules into sheets extending in the bc plane.

Related literature

For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Arshad et al. (2008 ▶, 2009 ▶); Khan et al. (2009 ▶); Gowda et al. (2007a ▶,b ▶,c ▶).

Experimental

Crystal data

C15H23NO2S

M = 281.40

Monoclinic,

a = 12.2269 (5) Å

b = 7.5818 (3) Å

c = 16.3045 (6) Å

β = 92.495 (2)°

V = 1510.03 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.43 × 0.32 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.914, T max = 0.969

16676 measured reflections

3714 independent reflections

2251 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 0.99

3713 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

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: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶)), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052593/bt5132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052593/bt5132Isup2.hkl

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

C15H23NO2S	F(000) = 608
Mr = 281.40	Dx = 1.238 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3495 reflections
a = 12.2269 (5) Å	θ = 2.5–25.6°
b = 7.5818 (3) Å	µ = 0.21 mm−1
c = 16.3045 (6) Å	T = 296 K
β = 92.495 (2)°	Needle, white
V = 1510.03 (10) Å3	0.43 × 0.32 × 0.15 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2251 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→15
Tmin = 0.914, Tmax = 0.969	k = −10→9
16676 measured reflections	l = −19→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.048P)2 + 0.3506P] where P = (Fo2 + 2Fc2)/3
3713 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.22960 (5)	1.10442 (7)	0.56680 (3)	0.05930 (19)
O1	0.14930 (14)	1.1507 (2)	0.50392 (9)	0.0866 (5)
O2	0.32184 (13)	1.21640 (19)	0.58303 (10)	0.0784 (5)
N1	0.27372 (13)	0.9101 (2)	0.54440 (9)	0.0549 (4)
C1	0.16215 (14)	1.0870 (2)	0.66002 (11)	0.0451 (4)
C2	0.21516 (14)	1.1373 (2)	0.73271 (11)	0.0511 (5)
H2	0.2856	1.1835	0.7326	0.061*
C3	0.16309 (15)	1.1186 (3)	0.80559 (12)	0.0528 (5)
H3	0.1994	1.1519	0.8544	0.063*
C4	0.05847 (15)	1.0517 (2)	0.80760 (11)	0.0491 (5)
C5	0.00638 (16)	1.0042 (3)	0.73394 (13)	0.0571 (5)
H5	−0.0645	0.9598	0.7341	0.069*
C6	0.05660 (16)	1.0209 (3)	0.66051 (12)	0.0555 (5)
H6	0.0201	0.9881	0.6117	0.067*
C7	0.36213 (15)	0.8297 (2)	0.59696 (11)	0.0494 (5)
H7	0.3938	0.9237	0.6317	0.059*
C8	0.45338 (16)	0.7582 (3)	0.54568 (12)	0.0576 (5)
H8A	0.4245	0.6660	0.5096	0.069*
H8B	0.4808	0.8521	0.5118	0.069*
C9	0.54647 (16)	0.6847 (3)	0.59987 (14)	0.0671 (6)
H9A	0.6019	0.6358	0.5657	0.081*
H9B	0.5797	0.7793	0.6323	0.081*
C10	0.50692 (17)	0.5438 (3)	0.65621 (13)	0.0642 (6)
H10A	0.5673	0.5044	0.6922	0.077*
H10B	0.4811	0.4435	0.6239	0.077*
C11	0.4154 (2)	0.6108 (3)	0.70741 (13)	0.0697 (6)
H11A	0.4437	0.7014	0.7446	0.084*
H11B	0.3883	0.5148	0.7402	0.084*
C12	0.32174 (16)	0.6864 (3)	0.65394 (12)	0.0606 (5)
H12A	0.2670	0.7355	0.6887	0.073*
H12B	0.2876	0.5926	0.6214	0.073*
C13	0.00216 (18)	1.0322 (3)	0.88731 (13)	0.0723 (6)
H13A	0.0434	1.0933	0.9300	0.108*
H13B	−0.0027	0.9095	0.9011	0.108*
H13C	−0.0701	1.0815	0.8817	0.108*
C14	0.21331 (17)	0.8024 (3)	0.48246 (12)	0.0608 (5)
H14A	0.1357	0.8263	0.4855	0.073*
H14B	0.2249	0.6787	0.4953	0.073*
C15	0.2469 (2)	0.8363 (3)	0.39659 (13)	0.0820 (7)
H15A	0.2338	0.9578	0.3828	0.123*
H15B	0.2050	0.7624	0.3592	0.123*
H15C	0.3233	0.8104	0.3927	0.123*

	U11	U22	U33	U12	U13	U23
S1	0.0778 (4)	0.0485 (3)	0.0529 (3)	0.0114 (3)	0.0175 (2)	0.0068 (2)
O1	0.1182 (13)	0.0855 (12)	0.0565 (9)	0.0423 (10)	0.0071 (9)	0.0196 (8)
O2	0.0959 (11)	0.0491 (9)	0.0935 (11)	−0.0132 (8)	0.0419 (9)	−0.0031 (8)
N1	0.0682 (10)	0.0513 (10)	0.0455 (9)	0.0081 (8)	0.0054 (7)	−0.0054 (8)
C1	0.0487 (10)	0.0398 (10)	0.0470 (10)	0.0075 (8)	0.0052 (8)	0.0001 (8)
C2	0.0410 (10)	0.0532 (12)	0.0591 (12)	−0.0008 (8)	0.0027 (9)	−0.0036 (9)
C3	0.0498 (11)	0.0590 (12)	0.0493 (11)	0.0003 (9)	−0.0015 (8)	−0.0077 (9)
C4	0.0537 (11)	0.0404 (10)	0.0537 (11)	0.0041 (8)	0.0078 (9)	−0.0022 (9)
C5	0.0451 (11)	0.0574 (13)	0.0692 (14)	−0.0064 (9)	0.0069 (9)	−0.0074 (10)
C6	0.0544 (12)	0.0569 (12)	0.0545 (12)	−0.0010 (10)	−0.0049 (9)	−0.0104 (10)
C7	0.0611 (11)	0.0441 (10)	0.0433 (10)	0.0015 (9)	0.0046 (8)	−0.0062 (8)
C8	0.0590 (12)	0.0559 (12)	0.0593 (12)	−0.0029 (10)	0.0164 (9)	0.0029 (10)
C9	0.0551 (12)	0.0620 (14)	0.0845 (16)	−0.0010 (11)	0.0058 (11)	−0.0003 (12)
C10	0.0640 (13)	0.0517 (12)	0.0760 (15)	0.0047 (10)	−0.0062 (11)	−0.0023 (11)
C11	0.0958 (16)	0.0593 (14)	0.0543 (12)	0.0046 (12)	0.0053 (11)	0.0072 (11)
C12	0.0674 (13)	0.0616 (13)	0.0543 (12)	0.0078 (11)	0.0207 (10)	0.0053 (10)
C13	0.0765 (15)	0.0772 (16)	0.0649 (14)	−0.0025 (12)	0.0229 (11)	−0.0008 (12)
C14	0.0638 (12)	0.0607 (13)	0.0576 (12)	−0.0026 (10)	−0.0001 (10)	−0.0015 (10)
C15	0.0992 (18)	0.0938 (19)	0.0525 (13)	−0.0011 (15)	−0.0013 (12)	−0.0099 (13)

S1—O2	1.4272 (16)	C8—H8B	0.9700
S1—O1	1.4320 (16)	C9—C10	1.502 (3)
S1—N1	1.6160 (17)	C9—H9A	0.9700
S1—C1	1.7654 (18)	C9—H9B	0.9700
N1—C14	1.472 (2)	C10—C11	1.513 (3)
N1—C7	1.481 (2)	C10—H10A	0.9700
C1—C2	1.380 (2)	C10—H10B	0.9700
C1—C6	1.385 (3)	C11—C12	1.521 (3)
C2—C3	1.380 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.378 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.383 (3)	C13—H13A	0.9600
C4—C13	1.504 (3)	C13—H13B	0.9600
C5—C6	1.375 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—C15	1.498 (3)
C6—H6	0.9300	C14—H14A	0.9700
C7—C8	1.523 (3)	C14—H14B	0.9700
C7—C12	1.525 (3)	C15—H15A	0.9600
C7—H7	0.9800	C15—H15B	0.9600
C8—C9	1.517 (3)	C15—H15C	0.9600
C8—H8A	0.9700
O2—S1—O1	119.90 (11)	C8—C9—H9A	109.4
O2—S1—N1	108.38 (9)	C10—C9—H9B	109.4
O1—S1—N1	106.68 (9)	C8—C9—H9B	109.4
O2—S1—C1	106.25 (9)	H9A—C9—H9B	108.0
O1—S1—C1	107.65 (9)	C9—C10—C11	111.34 (18)
N1—S1—C1	107.42 (8)	C9—C10—H10A	109.4
C14—N1—C7	120.00 (16)	C11—C10—H10A	109.4
C14—N1—S1	119.89 (13)	C9—C10—H10B	109.4
C7—N1—S1	119.14 (12)	C11—C10—H10B	109.4
C2—C1—C6	119.88 (17)	H10A—C10—H10B	108.0
C2—C1—S1	119.95 (14)	C10—C11—C12	111.52 (17)
C6—C1—S1	120.16 (15)	C10—C11—H11A	109.3
C3—C2—C1	119.63 (17)	C12—C11—H11A	109.3
C3—C2—H2	120.2	C10—C11—H11B	109.3
C1—C2—H2	120.2	C12—C11—H11B	109.3
C2—C3—C4	121.47 (17)	H11A—C11—H11B	108.0
C2—C3—H3	119.3	C11—C12—C7	111.20 (17)
C4—C3—H3	119.3	C11—C12—H12A	109.4
C3—C4—C5	117.93 (17)	C7—C12—H12A	109.4
C3—C4—C13	121.15 (18)	C11—C12—H12B	109.4
C5—C4—C13	120.93 (18)	C7—C12—H12B	109.4
C6—C5—C4	121.74 (18)	H12A—C12—H12B	108.0
C6—C5—H5	119.1	C4—C13—H13A	109.5
C4—C5—H5	119.1	C4—C13—H13B	109.5
C5—C6—C1	119.34 (18)	H13A—C13—H13B	109.5
C5—C6—H6	120.3	C4—C13—H13C	109.5
C1—C6—H6	120.3	H13A—C13—H13C	109.5
N1—C7—C8	111.26 (15)	H13B—C13—H13C	109.5
N1—C7—C12	113.46 (16)	N1—C14—C15	113.33 (17)
C8—C7—C12	110.21 (16)	N1—C14—H14A	108.9
N1—C7—H7	107.2	C15—C14—H14A	108.9
C8—C7—H7	107.2	N1—C14—H14B	108.9
C12—C7—H7	107.2	C15—C14—H14B	108.9
C9—C8—C7	111.12 (16)	H14A—C14—H14B	107.7
C9—C8—H8A	109.4	C14—C15—H15A	109.5
C7—C8—H8A	109.4	C14—C15—H15B	109.5
C9—C8—H8B	109.4	H15A—C15—H15B	109.5
C7—C8—H8B	109.4	C14—C15—H15C	109.5
H8A—C8—H8B	108.0	H15A—C15—H15C	109.5
C10—C9—C8	111.37 (17)	H15B—C15—H15C	109.5
C10—C9—H9A	109.4
O2—S1—N1—C14	−144.40 (15)	C13—C4—C5—C6	−179.92 (19)
O1—S1—N1—C14	−14.01 (17)	C4—C5—C6—C1	0.0 (3)
C1—S1—N1—C14	101.19 (15)	C2—C1—C6—C5	−0.8 (3)
O2—S1—N1—C7	46.86 (16)	S1—C1—C6—C5	178.40 (15)
O1—S1—N1—C7	177.24 (14)	C14—N1—C7—C8	60.5 (2)
C1—S1—N1—C7	−67.56 (15)	S1—N1—C7—C8	−130.77 (15)
O2—S1—C1—C2	−15.54 (18)	C14—N1—C7—C12	−64.5 (2)
O1—S1—C1—C2	−145.16 (16)	S1—N1—C7—C12	104.27 (17)
N1—S1—C1—C2	100.29 (16)	N1—C7—C8—C9	177.02 (16)
O2—S1—C1—C6	165.26 (15)	C12—C7—C8—C9	−56.2 (2)
O1—S1—C1—C6	35.64 (18)	C7—C8—C9—C10	56.7 (2)
N1—S1—C1—C6	−78.91 (16)	C8—C9—C10—C11	−55.7 (2)
C6—C1—C2—C3	1.0 (3)	C9—C10—C11—C12	55.0 (2)
S1—C1—C2—C3	−178.17 (14)	C10—C11—C12—C7	−55.1 (2)
C1—C2—C3—C4	−0.5 (3)	N1—C7—C12—C11	−179.00 (15)
C2—C3—C4—C5	−0.3 (3)	C8—C7—C12—C11	55.5 (2)
C2—C3—C4—C13	−179.85 (19)	C7—N1—C14—C15	−103.9 (2)
C3—C4—C5—C6	0.6 (3)	S1—N1—C14—C15	87.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2i	0.97	2.66	3.530 (3)	150
C13—H13A···O1ii	0.96	2.60	3.512 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2i	0.97	2.66	3.530 (3)	150
C13—H13A⋯O1ii	0.96	2.60	3.512 (3)	159

Symmetry codes: (i) ; (ii) .