N-Cyclo-hexyl-N-propyl-benzene-sulfonamide.

The title compound, C(15)H(23)NO(2)S, synthesized by N-methyl-ation of cyclo-hexyl-amine sulfonamide with propyl iodide, is of inter-est as a precursor to biologically active sulfur-containing heterocyclic compounds. The cyclo-hexyl ring exists in the chair form and the dihedral angle between the ring plane of the benzene ring and that of the cyclo-hexyl ring is 50.13 (9)°.

Related literature

For the synthesis of related mol­ecules, see: Kayser et al. (2004 ▶); Zia-ur-Rehman et al. (2006 ▶, 2009 ▶). For the biological activity of sulfonamides, see: La Roche & Co (1967 ▶); Rough et al. (1998 ▶); Gennarti et al. (1994 ▶). For related structures, see: Arshad et al. (2008 ▶); Khan et al. (2009 ▶); Gowda et al. (2007a ▶,b ▶,c ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H23NO2S

M = 281.40

Monoclinic,

a = 8.5532 (3) Å

b = 11.6877 (4) Å

c = 15.4410 (5) Å

β = 90.649 (2)°

V = 1543.50 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.42 × 0.31 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.918, T max = 0.950

17345 measured reflections

3839 independent reflections

2475 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 1.03

3839 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.21 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: 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, global. DOI: 10.1107/S1600536809046650/hg2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046650/hg2581Isup2.hkl

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

C15H23NO2S	F(000) = 608
Mr = 281.40	Dx = 1.211 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4904 reflections
a = 8.5532 (3) Å	θ = 2.2–24.1°
b = 11.6877 (4) Å	µ = 0.21 mm−1
c = 15.4410 (5) Å	T = 296 K
β = 90.649 (2)°	Needles, colourless
V = 1543.50 (9) Å3	0.42 × 0.31 × 0.25 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3839 independent reflections
Radiation source: fine-focus sealed tube	2475 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.918, Tmax = 0.950	k = −15→15
17345 measured reflections	l = −20→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.2752P] where P = (Fo2 + 2Fc2)/3
3839 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.21 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
S1	0.25538 (5)	0.86234 (4)	0.23201 (4)	0.05546 (19)
O1	0.36858 (17)	0.78724 (15)	0.26990 (10)	0.0777 (5)
O2	0.29533 (18)	0.97863 (13)	0.21357 (12)	0.0803 (5)
N1	0.10568 (17)	0.86333 (13)	0.29521 (10)	0.0483 (4)
C1	0.1958 (2)	0.80108 (17)	0.13244 (12)	0.0480 (4)
C2	0.1431 (3)	0.8704 (2)	0.06558 (16)	0.0702 (6)
H2	0.1435	0.9495	0.0718	0.084*
C3	0.0896 (3)	0.8205 (3)	−0.01092 (16)	0.0908 (9)
H3	0.0530	0.8666	−0.0559	0.109*
C4	0.0904 (3)	0.7056 (3)	−0.02042 (18)	0.0919 (9)
H4	0.0546	0.6731	−0.0719	0.110*
C5	0.1431 (3)	0.6373 (2)	0.04474 (18)	0.0800 (7)
H5	0.1438	0.5584	0.0373	0.096*
C6	0.1956 (2)	0.68386 (18)	0.12180 (14)	0.0579 (5)
H6	0.2307	0.6365	0.1664	0.070*
C7	−0.01977 (19)	0.94843 (16)	0.27965 (11)	0.0458 (4)
H7	0.0252	1.0101	0.2449	0.055*
C8	−0.0737 (2)	1.00139 (17)	0.36414 (12)	0.0535 (5)
H8A	−0.1183	0.9425	0.4006	0.064*
H8B	0.0154	1.0342	0.3947	0.064*
C9	−0.1949 (3)	1.09394 (19)	0.34699 (16)	0.0680 (6)
H9A	−0.2317	1.1236	0.4018	0.082*
H9B	−0.1467	1.1565	0.3157	0.082*
C10	−0.3316 (2)	1.0492 (2)	0.29526 (14)	0.0630 (6)
H10A	−0.4030	1.1116	0.2825	0.076*
H10B	−0.3871	0.9929	0.3293	0.076*
C11	−0.2801 (3)	0.9953 (2)	0.21182 (14)	0.0703 (6)
H11A	−0.2348	1.0533	0.1749	0.084*
H11B	−0.3702	0.9632	0.1818	0.084*
C12	−0.1603 (2)	0.9014 (2)	0.22887 (14)	0.0613 (6)
H12A	−0.1255	0.8701	0.1742	0.074*
H12B	−0.2084	0.8401	0.2615	0.074*
C13	0.0697 (2)	0.75885 (17)	0.34458 (13)	0.0545 (5)
H13A	0.1140	0.6935	0.3149	0.065*
H13B	−0.0428	0.7487	0.3456	0.065*
C14	0.1314 (3)	0.7611 (2)	0.43649 (16)	0.0804 (7)
H14A	0.2445	0.7669	0.4357	0.097*
H14B	0.0914	0.8284	0.4655	0.097*
C15	0.0861 (4)	0.6566 (2)	0.48662 (18)	0.0980 (9)
H15A	−0.0250	0.6564	0.4950	0.147*
H15B	0.1385	0.6571	0.5419	0.147*
H15C	0.1157	0.5894	0.4551	0.147*

	U11	U22	U33	U12	U13	U23
S1	0.0365 (3)	0.0626 (3)	0.0673 (4)	−0.0039 (2)	0.0035 (2)	−0.0127 (3)
O1	0.0456 (8)	0.1083 (13)	0.0789 (11)	0.0169 (8)	−0.0108 (7)	−0.0136 (9)
O2	0.0622 (9)	0.0621 (10)	0.1173 (13)	−0.0246 (7)	0.0279 (9)	−0.0219 (9)
N1	0.0423 (8)	0.0550 (9)	0.0477 (9)	0.0016 (7)	0.0022 (7)	−0.0050 (7)
C1	0.0392 (9)	0.0537 (11)	0.0514 (11)	0.0011 (8)	0.0112 (8)	0.0023 (9)
C2	0.0690 (15)	0.0709 (15)	0.0711 (16)	0.0122 (11)	0.0181 (12)	0.0127 (12)
C3	0.0806 (18)	0.140 (3)	0.0521 (15)	0.0295 (18)	0.0081 (12)	0.0178 (16)
C4	0.0700 (16)	0.142 (3)	0.0642 (17)	0.0134 (18)	0.0044 (13)	−0.0290 (18)
C5	0.0737 (17)	0.0819 (17)	0.0847 (19)	−0.0037 (13)	0.0127 (14)	−0.0285 (15)
C6	0.0567 (12)	0.0565 (12)	0.0607 (13)	0.0038 (9)	0.0086 (10)	−0.0045 (10)
C7	0.0402 (9)	0.0529 (11)	0.0444 (10)	−0.0004 (8)	0.0011 (7)	−0.0036 (8)
C8	0.0516 (11)	0.0602 (12)	0.0485 (11)	0.0030 (9)	−0.0064 (8)	−0.0130 (9)
C9	0.0713 (15)	0.0626 (13)	0.0702 (14)	0.0163 (11)	0.0034 (11)	−0.0114 (11)
C10	0.0527 (12)	0.0780 (14)	0.0584 (13)	0.0185 (10)	0.0022 (10)	0.0054 (11)
C11	0.0524 (12)	0.1059 (19)	0.0525 (12)	0.0112 (12)	−0.0068 (10)	0.0014 (12)
C12	0.0464 (11)	0.0857 (15)	0.0518 (12)	0.0056 (10)	−0.0062 (9)	−0.0209 (11)
C13	0.0507 (11)	0.0565 (12)	0.0564 (12)	0.0007 (9)	−0.0040 (9)	−0.0079 (9)
C14	0.0900 (18)	0.0855 (17)	0.0652 (15)	0.0007 (14)	−0.0233 (13)	0.0073 (13)
C15	0.119 (2)	0.095 (2)	0.0801 (18)	0.0125 (17)	0.0040 (17)	0.0243 (15)

S1—O1	1.4274 (16)	C8—H8B	0.9700
S1—O2	1.4308 (16)	C9—C10	1.502 (3)
S1—N1	1.6187 (15)	C9—H9A	0.9700
S1—C1	1.7658 (19)	C9—H9B	0.9700
N1—C13	1.474 (2)	C10—C11	1.504 (3)
N1—C7	1.481 (2)	C10—H10A	0.9700
C1—C6	1.380 (3)	C10—H10B	0.9700
C1—C2	1.384 (3)	C11—C12	1.522 (3)
C2—C3	1.390 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.351 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.357 (4)	C13—C14	1.509 (3)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.379 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C15	1.499 (3)
C6—H6	0.9300	C14—H14A	0.9700
C7—C8	1.520 (2)	C14—H14B	0.9700
C7—C12	1.530 (2)	C15—H15A	0.9600
C7—H7	0.9800	C15—H15B	0.9600
C8—C9	1.520 (3)	C15—H15C	0.9600
C8—H8A	0.9700
O1—S1—O2	120.22 (11)	C8—C9—H9A	109.3
O1—S1—N1	107.15 (9)	C10—C9—H9B	109.3
O2—S1—N1	107.79 (9)	C8—C9—H9B	109.3
O1—S1—C1	107.16 (9)	H9A—C9—H9B	107.9
O2—S1—C1	106.21 (10)	C9—C10—C11	111.57 (18)
N1—S1—C1	107.79 (8)	C9—C10—H10A	109.3
C13—N1—C7	119.02 (15)	C11—C10—H10A	109.3
C13—N1—S1	118.51 (13)	C9—C10—H10B	109.3
C7—N1—S1	118.92 (12)	C11—C10—H10B	109.3
C6—C1—C2	119.5 (2)	H10A—C10—H10B	108.0
C6—C1—S1	120.41 (15)	C10—C11—C12	110.90 (17)
C2—C1—S1	120.04 (17)	C10—C11—H11A	109.5
C1—C2—C3	119.4 (2)	C12—C11—H11A	109.5
C1—C2—H2	120.3	C10—C11—H11B	109.5
C3—C2—H2	120.3	C12—C11—H11B	109.5
C4—C3—C2	120.5 (3)	H11A—C11—H11B	108.0
C4—C3—H3	119.8	C11—C12—C7	110.64 (17)
C2—C3—H3	119.8	C11—C12—H12A	109.5
C3—C4—C5	120.4 (3)	C7—C12—H12A	109.5
C3—C4—H4	119.8	C11—C12—H12B	109.5
C5—C4—H4	119.8	C7—C12—H12B	109.5
C4—C5—C6	120.7 (3)	H12A—C12—H12B	108.1
C4—C5—H5	119.7	N1—C13—C14	113.53 (17)
C6—C5—H5	119.7	N1—C13—H13A	108.9
C5—C6—C1	119.6 (2)	C14—C13—H13A	108.9
C5—C6—H6	120.2	N1—C13—H13B	108.9
C1—C6—H6	120.2	C14—C13—H13B	108.9
N1—C7—C8	111.13 (14)	H13A—C13—H13B	107.7
N1—C7—C12	113.91 (15)	C15—C14—C13	112.4 (2)
C8—C7—C12	110.00 (15)	C15—C14—H14A	109.1
N1—C7—H7	107.2	C13—C14—H14A	109.1
C8—C7—H7	107.2	C15—C14—H14B	109.1
C12—C7—H7	107.2	C13—C14—H14B	109.1
C9—C8—C7	110.68 (16)	H14A—C14—H14B	107.8
C9—C8—H8A	109.5	C14—C15—H15A	109.5
C7—C8—H8A	109.5	C14—C15—H15B	109.5
C9—C8—H8B	109.5	H15A—C15—H15B	109.5
C7—C8—H8B	109.5	C14—C15—H15C	109.5
H8A—C8—H8B	108.1	H15A—C15—H15C	109.5
C10—C9—C8	111.73 (18)	H15B—C15—H15C	109.5
C10—C9—H9A	109.3
O1—S1—N1—C13	−31.31 (16)	C2—C1—C6—C5	0.1 (3)
O2—S1—N1—C13	−162.01 (14)	S1—C1—C6—C5	177.52 (16)
C1—S1—N1—C13	83.73 (14)	C13—N1—C7—C8	64.7 (2)
O1—S1—N1—C7	170.12 (13)	S1—N1—C7—C8	−136.84 (14)
O2—S1—N1—C7	39.42 (16)	C13—N1—C7—C12	−60.2 (2)
C1—S1—N1—C7	−74.84 (15)	S1—N1—C7—C12	98.24 (17)
O1—S1—C1—C6	30.33 (18)	N1—C7—C8—C9	176.37 (16)
O2—S1—C1—C6	160.00 (15)	C12—C7—C8—C9	−56.5 (2)
N1—S1—C1—C6	−84.70 (16)	C7—C8—C9—C10	55.9 (2)
O1—S1—C1—C2	−152.24 (16)	C8—C9—C10—C11	−55.4 (3)
O2—S1—C1—C2	−22.57 (18)	C9—C10—C11—C12	55.7 (3)
N1—S1—C1—C2	92.73 (17)	C10—C11—C12—C7	−56.7 (3)
C6—C1—C2—C3	0.5 (3)	N1—C7—C12—C11	−177.24 (17)
S1—C1—C2—C3	−176.93 (17)	C8—C7—C12—C11	57.2 (2)
C1—C2—C3—C4	−0.6 (4)	C7—N1—C13—C14	−103.9 (2)
C2—C3—C4—C5	0.1 (4)	S1—N1—C13—C14	97.55 (19)
C3—C4—C5—C6	0.5 (4)	N1—C13—C14—C15	177.0 (2)
C4—C5—C6—C1	−0.6 (3)