A second monoclinic polymorph of N-cyclo-hexyl-N-ethyl-benzene-sulfonamide.

The crystal structure of the title compound, C(14)H(21)NO(2)S, is a polymorph of the structure reported by Khan et al. [Acta Cryst. (2009), E65, o2867] which is also monoclinic (space group P2(1)/c). The unit cell in the title structure is approximately half the volume of the previously reported polymorph and the asymmetric unit of the title compound contains one mol-ecule rather than two independent mol-ecules in the other polymorph. In the title mol-ecule, the cyclo-hexane ring is in the typical chair form. In the crystal structure, mol-ecules are linked via weak inter-molecular C-H⋯O inter-actions, forming a chain along the b-axis direction.

Related literature

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

Experimental

Crystal data

C14H21NO2S

M = 267.38

Monoclinic,

a = 8.3837 (4) Å

b = 11.4467 (5) Å

c = 15.1488 (7) Å

β = 92.541 (2)°

V = 1452.34 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.41 × 0.28 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.916, T max = 0.976

15910 measured reflections

3651 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.02

3651 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.36 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/S160053680904762X/lh2950sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904762X/lh2950Isup2.hkl

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

C14H21NO2S	F(000) = 576
Mr = 267.38	Dx = 1.223 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4610 reflections
a = 8.3837 (4) Å	θ = 2.8–27.6°
b = 11.4467 (5) Å	µ = 0.22 mm−1
c = 15.1488 (7) Å	T = 296 K
β = 92.541 (2)°	Needle, colourless
V = 1452.34 (12) Å3	0.41 × 0.28 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	3651 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 28.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −11→10
Tmin = 0.916, Tmax = 0.976	k = −15→14
15910 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.3342P] where P = (Fo2 + 2Fc2)/3
3651 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.36 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	0.22296 (5)	0.78592 (4)	0.73395 (3)	0.04988 (15)
O1	0.14310 (16)	0.68075 (13)	0.70635 (9)	0.0702 (4)
O2	0.14198 (15)	0.89484 (12)	0.72376 (10)	0.0720 (4)
N1	0.38527 (16)	0.79318 (12)	0.68134 (9)	0.0455 (3)
C1	0.27998 (18)	0.77256 (14)	0.84693 (10)	0.0427 (4)
C2	0.2929 (3)	0.87099 (18)	0.89914 (13)	0.0658 (5)
H2	0.2641	0.9436	0.8760	0.079*
C3	0.3483 (3)	0.8612 (2)	0.98515 (15)	0.0841 (7)
H3	0.3569	0.9276	1.0205	0.101*
C4	0.3908 (3)	0.7554 (3)	1.01939 (14)	0.0809 (7)
H4	0.4296	0.7497	1.0777	0.097*
C5	0.3767 (2)	0.6566 (2)	0.96771 (14)	0.0710 (6)
H5	0.4048	0.5843	0.9916	0.085*
C6	0.3209 (2)	0.66398 (16)	0.88051 (12)	0.0528 (4)
H6	0.3113	0.5975	0.8454	0.063*
C7	0.49240 (18)	0.89465 (14)	0.69898 (10)	0.0410 (4)
H7	0.4309	0.9530	0.7304	0.049*
C8	0.6390 (2)	0.86509 (15)	0.75812 (11)	0.0507 (4)
H8A	0.6055	0.8330	0.8136	0.061*
H8B	0.7026	0.8065	0.7296	0.061*
C9	0.7397 (2)	0.97408 (17)	0.77604 (11)	0.0579 (5)
H9A	0.6786	1.0303	0.8085	0.069*
H9B	0.8340	0.9536	0.8121	0.069*
C10	0.7892 (2)	1.02824 (16)	0.69050 (12)	0.0547 (5)
H10A	0.8578	0.9744	0.6605	0.066*
H10B	0.8495	1.0990	0.7033	0.066*
C11	0.6449 (2)	1.05710 (15)	0.63070 (12)	0.0550 (4)
H11A	0.6803	1.0871	0.5750	0.066*
H11B	0.5828	1.1177	0.6580	0.066*
C12	0.53986 (19)	0.95047 (14)	0.61323 (10)	0.0457 (4)
H12A	0.4446	0.9735	0.5789	0.055*
H12B	0.5971	0.8939	0.5790	0.055*
C13	0.4471 (2)	0.68754 (15)	0.63861 (12)	0.0542 (5)
H13A	0.4181	0.6195	0.6726	0.065*
H13B	0.5627	0.6916	0.6396	0.065*
C14	0.3849 (3)	0.67214 (18)	0.54449 (13)	0.0760 (6)
H14A	0.2704	0.6677	0.5429	0.114*
H14B	0.4273	0.6014	0.5208	0.114*
H14C	0.4172	0.7374	0.5098	0.114*

	U11	U22	U33	U12	U13	U23
S1	0.0385 (2)	0.0606 (3)	0.0500 (3)	−0.0046 (2)	−0.00434 (17)	0.0147 (2)
O1	0.0615 (8)	0.0877 (10)	0.0603 (8)	−0.0332 (7)	−0.0110 (6)	0.0087 (7)
O2	0.0469 (7)	0.0815 (10)	0.0880 (10)	0.0182 (7)	0.0050 (7)	0.0353 (8)
N1	0.0459 (8)	0.0483 (8)	0.0421 (7)	−0.0072 (6)	0.0015 (6)	0.0003 (6)
C1	0.0378 (8)	0.0476 (9)	0.0431 (9)	−0.0015 (7)	0.0050 (7)	0.0043 (7)
C2	0.0839 (14)	0.0548 (12)	0.0599 (12)	0.0012 (10)	0.0160 (10)	−0.0002 (9)
C3	0.1083 (19)	0.0908 (18)	0.0541 (13)	−0.0248 (15)	0.0138 (12)	−0.0155 (12)
C4	0.0689 (14)	0.131 (2)	0.0427 (11)	−0.0152 (14)	−0.0031 (10)	0.0049 (13)
C5	0.0665 (13)	0.0872 (16)	0.0594 (12)	0.0133 (12)	0.0045 (10)	0.0285 (12)
C6	0.0543 (10)	0.0529 (11)	0.0513 (10)	0.0005 (9)	0.0064 (8)	0.0090 (8)
C7	0.0408 (8)	0.0433 (9)	0.0387 (8)	−0.0020 (7)	0.0010 (6)	0.0009 (7)
C8	0.0509 (10)	0.0581 (11)	0.0422 (9)	−0.0051 (8)	−0.0066 (7)	0.0079 (8)
C9	0.0556 (11)	0.0678 (13)	0.0494 (10)	−0.0100 (9)	−0.0087 (8)	−0.0030 (9)
C10	0.0516 (10)	0.0528 (11)	0.0599 (11)	−0.0123 (8)	0.0033 (8)	−0.0052 (8)
C11	0.0592 (11)	0.0480 (10)	0.0580 (11)	−0.0046 (8)	0.0052 (9)	0.0101 (8)
C12	0.0456 (9)	0.0512 (10)	0.0399 (9)	−0.0009 (8)	−0.0014 (7)	0.0087 (7)
C13	0.0606 (11)	0.0449 (10)	0.0567 (11)	−0.0022 (8)	−0.0024 (9)	0.0017 (8)
C14	0.1067 (18)	0.0615 (13)	0.0591 (12)	−0.0003 (12)	−0.0042 (12)	−0.0115 (10)

S1—O2	1.4247 (13)	C8—C9	1.524 (2)
S1—O1	1.4309 (14)	C8—H8A	0.9700
S1—N1	1.6093 (14)	C8—H8B	0.9700
S1—C1	1.7632 (16)	C9—C10	1.511 (2)
N1—C13	1.476 (2)	C9—H9A	0.9700
N1—C7	1.485 (2)	C9—H9B	0.9700
C1—C2	1.378 (2)	C10—C11	1.515 (2)
C1—C6	1.381 (2)	C10—H10A	0.9700
C2—C3	1.368 (3)	C10—H10B	0.9700
C2—H2	0.9300	C11—C12	1.521 (2)
C3—C4	1.359 (3)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.377 (3)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.384 (3)	C13—C14	1.507 (3)
C5—H5	0.9300	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700
C7—C12	1.516 (2)	C14—H14A	0.9600
C7—C8	1.527 (2)	C14—H14B	0.9600
C7—H7	0.9800	C14—H14C	0.9600
O2—S1—O1	119.34 (9)	H8A—C8—H8B	108.1
O2—S1—N1	108.08 (8)	C10—C9—C8	110.74 (14)
O1—S1—N1	107.08 (8)	C10—C9—H9A	109.5
O2—S1—C1	106.77 (9)	C8—C9—H9A	109.5
O1—S1—C1	108.29 (8)	C10—C9—H9B	109.5
N1—S1—C1	106.64 (7)	C8—C9—H9B	109.5
C13—N1—C7	119.89 (13)	H9A—C9—H9B	108.1
C13—N1—S1	119.71 (11)	C9—C10—C11	111.09 (15)
C7—N1—S1	117.98 (11)	C9—C10—H10A	109.4
C2—C1—C6	120.85 (16)	C11—C10—H10A	109.4
C2—C1—S1	119.81 (14)	C9—C10—H10B	109.4
C6—C1—S1	119.21 (13)	C11—C10—H10B	109.4
C3—C2—C1	119.6 (2)	H10A—C10—H10B	108.0
C3—C2—H2	120.2	C10—C11—C12	111.69 (14)
C1—C2—H2	120.2	C10—C11—H11A	109.3
C4—C3—C2	120.6 (2)	C12—C11—H11A	109.3
C4—C3—H3	119.7	C10—C11—H11B	109.3
C2—C3—H3	119.7	C12—C11—H11B	109.3
C3—C4—C5	120.01 (19)	H11A—C11—H11B	107.9
C3—C4—H4	120.0	C7—C12—C11	111.15 (13)
C5—C4—H4	120.0	C7—C12—H12A	109.4
C4—C5—C6	120.6 (2)	C11—C12—H12A	109.4
C4—C5—H5	119.7	C7—C12—H12B	109.4
C6—C5—H5	119.7	C11—C12—H12B	109.4
C1—C6—C5	118.32 (18)	H12A—C12—H12B	108.0
C1—C6—H6	120.8	N1—C13—C14	113.41 (15)
C5—C6—H6	120.8	N1—C13—H13A	108.9
N1—C7—C12	110.79 (12)	C14—C13—H13A	108.9
N1—C7—C8	113.40 (13)	N1—C13—H13B	108.9
C12—C7—C8	111.16 (13)	C14—C13—H13B	108.9
N1—C7—H7	107.0	H13A—C13—H13B	107.7
C12—C7—H7	107.0	C13—C14—H14A	109.5
C8—C7—H7	107.0	C13—C14—H14B	109.5
C9—C8—C7	110.38 (14)	H14A—C14—H14B	109.5
C9—C8—H8A	109.6	C13—C14—H14C	109.5
C7—C8—H8A	109.6	H14A—C14—H14C	109.5
C9—C8—H8B	109.6	H14B—C14—H14C	109.5
C7—C8—H8B	109.6
O2—S1—N1—C13	−146.72 (13)	C2—C1—C6—C5	−0.6 (3)
O1—S1—N1—C13	−16.96 (14)	S1—C1—C6—C5	175.29 (14)
C1—S1—N1—C13	98.80 (13)	C4—C5—C6—C1	−0.1 (3)
O2—S1—N1—C7	50.94 (13)	C13—N1—C7—C12	66.92 (17)
O1—S1—N1—C7	−179.30 (11)	S1—N1—C7—C12	−130.77 (12)
C1—S1—N1—C7	−63.54 (13)	C13—N1—C7—C8	−58.89 (19)
O2—S1—C1—C2	−21.71 (17)	S1—N1—C7—C8	103.43 (15)
O1—S1—C1—C2	−151.40 (15)	N1—C7—C8—C9	−177.88 (13)
N1—S1—C1—C2	93.66 (16)	C12—C7—C8—C9	56.52 (19)
O2—S1—C1—C6	162.38 (13)	C7—C8—C9—C10	−57.4 (2)
O1—S1—C1—C6	32.69 (16)	C8—C9—C10—C11	56.9 (2)
N1—S1—C1—C6	−82.25 (15)	C9—C10—C11—C12	−55.4 (2)
C6—C1—C2—C3	0.6 (3)	N1—C7—C12—C11	178.00 (13)
S1—C1—C2—C3	−175.27 (16)	C8—C7—C12—C11	−54.96 (19)
C1—C2—C3—C4	0.1 (3)	C10—C11—C12—C7	54.4 (2)
C2—C3—C4—C5	−0.7 (4)	C7—N1—C13—C14	−107.93 (18)
C3—C4—C5—C6	0.7 (3)	S1—N1—C13—C14	90.06 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.58	3.482 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.58	3.482 (2)	163

Symmetry code: (i) .