N-Cyclo-hexyl-N-(prop-2-en-1-yl)benzene-sulfonamide.

The title compound, C(15)H(21)NO(2)S, synthesized by N-alkyl-ation of cyclo-hexyl-amine benzene-sulfonamide with allyl iodide, is of inter-est as a precursor to biologically active sulfur-containing heterocyclic compounds. The cyclo-hexane ring is in a chair form and its mean plane makes a dihedral angle of 53.84 (12)° with the phenyl ring.

Related literature

For the synthesis of related mol­ecules, see: Arshad et al. (2009 ▶); Zia-ur-Rehman et al. (2009 ▶). For biological applications of sulfonamides, see: Connor (1998 ▶); Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Xiao & Timberlake (2000 ▶). For a related structure, see: Khan et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H21NO2S

M = 279.39

Monoclinic,

a = 8.4911 (5) Å

b = 11.4176 (6) Å

c = 15.6274 (10) Å

β = 94.188 (3)°

V = 1511.00 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.38 × 0.18 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.924, T max = 0.975

16559 measured reflections

3746 independent reflections

2179 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.144

S = 1.02

3746 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.34 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/S1600536809048077/is2487sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048077/is2487Isup2.hkl

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

C15H21NO2S	F(000) = 600
Mr = 279.39	Dx = 1.228 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3312 reflections
a = 8.4911 (5) Å	θ = 2.2–21.3°
b = 11.4176 (6) Å	µ = 0.21 mm−1
c = 15.6274 (10) Å	T = 296 K
β = 94.188 (3)°	Needles, light yellow
V = 1511.00 (15) Å3	0.38 × 0.18 × 0.12 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3746 independent reflections
Radiation source: fine-focus sealed tube	2179 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.924, Tmax = 0.975	k = −15→15
16559 measured reflections	l = −19→20

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.3938P] where P = (Fo2 + 2Fc2)/3
3746 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.34 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	0.27668 (7)	0.31209 (5)	0.25071 (4)	0.0519 (2)
O1	0.3713 (2)	0.21435 (17)	0.27943 (11)	0.0744 (6)
O2	0.3425 (2)	0.42730 (16)	0.25495 (14)	0.0776 (6)
N1	0.1228 (2)	0.31154 (15)	0.30554 (12)	0.0460 (5)
C1	0.2123 (2)	0.28696 (18)	0.14300 (14)	0.0438 (5)
C2	0.1843 (3)	0.3808 (2)	0.08789 (19)	0.0714 (8)
H2	0.2024	0.4570	0.1073	0.086*
C3	0.1297 (4)	0.3605 (3)	0.0047 (2)	0.0942 (11)
H3	0.1097	0.4233	−0.0324	0.113*
C4	0.1044 (4)	0.2497 (4)	−0.02421 (19)	0.0881 (10)
H4	0.0692	0.2370	−0.0812	0.106*
C5	0.1303 (3)	0.1558 (3)	0.03010 (18)	0.0744 (8)
H5	0.1110	0.0801	0.0101	0.089*
C6	0.1849 (3)	0.1740 (2)	0.11428 (16)	0.0534 (6)
H6	0.2032	0.1108	0.1513	0.064*
C7	0.0098 (2)	0.41024 (18)	0.29605 (14)	0.0416 (5)
H7	0.0635	0.4740	0.2679	0.050*
C8	−0.0307 (3)	0.45575 (19)	0.38291 (14)	0.0485 (6)
H8A	0.0654	0.4776	0.4164	0.058*
H8B	−0.0819	0.3943	0.4136	0.058*
C9	−0.1402 (3)	0.5618 (2)	0.37271 (16)	0.0584 (7)
H9A	−0.1702	0.5861	0.4287	0.070*
H9B	−0.0841	0.6263	0.3482	0.070*
C10	−0.2872 (3)	0.5350 (2)	0.31574 (16)	0.0573 (6)
H10A	−0.3497	0.4769	0.3433	0.069*
H10B	−0.3503	0.6055	0.3078	0.069*
C11	−0.2460 (3)	0.4895 (2)	0.22941 (16)	0.0621 (7)
H11A	−0.1928	0.5504	0.1993	0.074*
H11B	−0.3421	0.4689	0.1953	0.074*
C12	−0.1393 (3)	0.3822 (2)	0.23980 (15)	0.0539 (6)
H12A	−0.1959	0.3190	0.2655	0.065*
H12B	−0.1109	0.3563	0.1838	0.065*
C13	0.0737 (3)	0.20179 (19)	0.34549 (16)	0.0566 (6)
H13A	0.1046	0.1358	0.3114	0.068*
H13B	−0.0404	0.2007	0.3464	0.068*
C14	0.1475 (4)	0.1896 (2)	0.4359 (2)	0.0795 (9)
H14	0.2546	0.2069	0.4439	0.095*
C15	0.0842 (6)	0.1601 (3)	0.4985 (3)	0.1242 (14)
H15A	−0.0228	0.1417	0.4943	0.149*
H15B	0.1420	0.1557	0.5513	0.149*

	U11	U22	U33	U12	U13	U23
S1	0.0389 (3)	0.0632 (4)	0.0529 (4)	0.0041 (3)	−0.0012 (3)	−0.0167 (3)
O1	0.0604 (11)	0.1025 (14)	0.0580 (12)	0.0354 (10)	−0.0124 (9)	−0.0179 (10)
O2	0.0527 (10)	0.0808 (13)	0.1011 (15)	−0.0240 (9)	0.0184 (10)	−0.0401 (11)
N1	0.0466 (11)	0.0490 (10)	0.0423 (11)	0.0079 (8)	0.0035 (9)	−0.0034 (8)
C1	0.0376 (11)	0.0515 (12)	0.0429 (13)	0.0029 (9)	0.0074 (10)	−0.0026 (10)
C2	0.090 (2)	0.0625 (16)	0.0642 (19)	0.0097 (14)	0.0200 (16)	0.0112 (14)
C3	0.114 (3)	0.112 (3)	0.058 (2)	0.044 (2)	0.0161 (19)	0.026 (2)
C4	0.072 (2)	0.149 (3)	0.0426 (17)	0.027 (2)	−0.0041 (14)	−0.005 (2)
C5	0.0732 (19)	0.093 (2)	0.0562 (18)	−0.0054 (16)	0.0002 (15)	−0.0247 (16)
C6	0.0576 (15)	0.0552 (14)	0.0473 (14)	0.0014 (11)	0.0037 (12)	−0.0037 (11)
C7	0.0413 (12)	0.0455 (11)	0.0380 (12)	0.0012 (9)	0.0026 (10)	−0.0027 (9)
C8	0.0505 (13)	0.0538 (13)	0.0409 (13)	0.0021 (10)	0.0010 (11)	−0.0096 (10)
C9	0.0706 (17)	0.0520 (13)	0.0534 (15)	0.0092 (12)	0.0098 (13)	−0.0102 (11)
C10	0.0553 (15)	0.0609 (14)	0.0561 (16)	0.0170 (12)	0.0065 (12)	0.0024 (12)
C11	0.0565 (15)	0.0786 (17)	0.0496 (16)	0.0154 (13)	−0.0053 (12)	−0.0003 (13)
C12	0.0515 (14)	0.0666 (15)	0.0424 (14)	0.0077 (11)	−0.0056 (11)	−0.0133 (11)
C13	0.0663 (16)	0.0484 (13)	0.0549 (16)	0.0073 (11)	0.0034 (13)	−0.0028 (11)
C14	0.097 (2)	0.0728 (18)	0.070 (2)	0.0197 (16)	0.0169 (18)	0.0238 (16)
C15	0.164 (4)	0.111 (3)	0.097 (3)	0.014 (3)	0.009 (3)	0.025 (2)

S1—O1	1.4283 (18)	C8—H8A	0.9700
S1—O2	1.4289 (17)	C8—H8B	0.9700
S1—N1	1.6136 (19)	C9—C10	1.511 (4)
S1—C1	1.755 (2)	C9—H9A	0.9700
N1—C13	1.474 (3)	C9—H9B	0.9700
N1—C7	1.481 (2)	C10—C11	1.510 (3)
C1—C6	1.380 (3)	C10—H10A	0.9700
C1—C2	1.385 (3)	C10—H10B	0.9700
C2—C3	1.368 (4)	C11—C12	1.525 (3)
C2—H2	0.9300	C11—H11A	0.9700
C3—C4	1.355 (5)	C11—H11B	0.9700
C3—H3	0.9300	C12—H12A	0.9700
C4—C5	1.375 (4)	C12—H12B	0.9700
C4—H4	0.9300	C13—C14	1.509 (4)
C5—C6	1.378 (4)	C13—H13A	0.9700
C5—H5	0.9300	C13—H13B	0.9700
C6—H6	0.9300	C14—C15	1.198 (4)
C7—C8	1.516 (3)	C14—H14	0.9300
C7—C12	1.522 (3)	C15—H15A	0.9300
C7—H7	0.9800	C15—H15B	0.9300
C8—C9	1.528 (3)
O1—S1—O2	119.70 (12)	H8A—C8—H8B	108.1
O1—S1—N1	106.79 (11)	C10—C9—C8	111.75 (18)
O2—S1—N1	107.95 (10)	C10—C9—H9A	109.3
O1—S1—C1	107.60 (10)	C8—C9—H9A	109.3
O2—S1—C1	106.76 (12)	C10—C9—H9B	109.3
N1—S1—C1	107.52 (10)	C8—C9—H9B	109.3
C13—N1—C7	119.21 (17)	H9A—C9—H9B	107.9
C13—N1—S1	119.58 (14)	C11—C10—C9	111.2 (2)
C7—N1—S1	119.19 (14)	C11—C10—H10A	109.4
C6—C1—C2	120.3 (2)	C9—C10—H10A	109.4
C6—C1—S1	119.87 (17)	C11—C10—H10B	109.4
C2—C1—S1	119.82 (19)	C9—C10—H10B	109.4
C3—C2—C1	119.4 (3)	H10A—C10—H10B	108.0
C3—C2—H2	120.3	C10—C11—C12	110.8 (2)
C1—C2—H2	120.3	C10—C11—H11A	109.5
C4—C3—C2	120.7 (3)	C12—C11—H11A	109.5
C4—C3—H3	119.7	C10—C11—H11B	109.5
C2—C3—H3	119.7	C12—C11—H11B	109.5
C3—C4—C5	120.5 (3)	H11A—C11—H11B	108.1
C3—C4—H4	119.8	C7—C12—C11	110.82 (19)
C5—C4—H4	119.8	C7—C12—H12A	109.5
C4—C5—C6	120.0 (3)	C11—C12—H12A	109.5
C4—C5—H5	120.0	C7—C12—H12B	109.5
C6—C5—H5	120.0	C11—C12—H12B	109.5
C5—C6—C1	119.2 (2)	H12A—C12—H12B	108.1
C5—C6—H6	120.4	N1—C13—C14	111.3 (2)
C1—C6—H6	120.4	N1—C13—H13A	109.4
N1—C7—C8	111.04 (17)	C14—C13—H13A	109.4
N1—C7—C12	113.81 (17)	N1—C13—H13B	109.4
C8—C7—C12	110.80 (18)	C14—C13—H13B	109.4
N1—C7—H7	106.9	H13A—C13—H13B	108.0
C8—C7—H7	106.9	C15—C14—C13	127.5 (4)
C12—C7—H7	106.9	C15—C14—H14	116.2
C7—C8—C9	110.76 (19)	C13—C14—H14	116.2
C7—C8—H8A	109.5	C14—C15—H15A	120.0
C9—C8—H8A	109.5	C14—C15—H15B	120.0
C7—C8—H8B	109.5	H15A—C15—H15B	120.0
C9—C8—H8B	109.5
O1—S1—N1—C13	−22.4 (2)	C2—C1—C6—C5	0.3 (4)
O2—S1—N1—C13	−152.36 (18)	S1—C1—C6—C5	178.25 (19)
C1—S1—N1—C13	92.80 (18)	C13—N1—C7—C8	64.3 (2)
O1—S1—N1—C7	173.87 (15)	S1—N1—C7—C8	−131.93 (17)
O2—S1—N1—C7	43.96 (19)	C13—N1—C7—C12	−61.5 (3)
C1—S1—N1—C7	−70.88 (17)	S1—N1—C7—C12	102.2 (2)
O1—S1—C1—C6	32.0 (2)	N1—C7—C8—C9	176.87 (18)
O2—S1—C1—C6	161.62 (18)	C12—C7—C8—C9	−55.6 (2)
N1—S1—C1—C6	−82.75 (19)	C7—C8—C9—C10	55.1 (3)
O1—S1—C1—C2	−150.1 (2)	C8—C9—C10—C11	−55.4 (3)
O2—S1—C1—C2	−20.4 (2)	C9—C10—C11—C12	56.1 (3)
N1—S1—C1—C2	95.2 (2)	N1—C7—C12—C11	−177.19 (19)
C6—C1—C2—C3	−0.2 (4)	C8—C7—C12—C11	56.8 (3)
S1—C1—C2—C3	−178.1 (2)	C10—C11—C12—C7	−56.9 (3)
C1—C2—C3—C4	−0.6 (5)	C7—N1—C13—C14	−104.9 (2)
C2—C3—C4—C5	1.3 (5)	S1—N1—C13—C14	91.5 (2)
C3—C4—C5—C6	−1.1 (5)	N1—C13—C14—C15	134.8 (4)
C4—C5—C6—C1	0.3 (4)