4-Chloro-N-cyclo­hexyl­benzene­sulfonamide

Abstract

The title compound, C₁₂H₁₆ClNO₂S, adopts an L-shaped conformation, with the central C—S—N—C torsion angle being −78.0 (2)°. The cyclo­hexyl ring adopts a chair conformation. In the crystal, adjacent mol­ecules are connected by pairs of N—H⋯O hydrogen bonds around an inversion centre, forming cyclic dimers [graph set R ₂ ²(8)].

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2011 ▶); Khan et al. (2010 ▶); John et al. (2010 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

• C₁₂H₁₆ClNO₂S

• M _r = 273.78

• Monoclinic,

• a = 11.1226 (5) Å

• b = 6.2490 (2) Å

• c = 19.8635 (9) Å

• β = 96.505 (2)°

• V = 1371.73 (10) ų

• Z = 4

• Mo Kα radiation

• μ = 0.42 mm⁻¹

• T = 296 K

• 0.29 × 0.15 × 0.11 mm

Data collection

• Bruker APEXII CCD diffractometer

• 12714 measured reflections

• 3365 independent reflections

• 2075 reflections with I > 2σ(I)

• R _int = 0.030

Refinement

• R[F ² > 2σ(F ²)] = 0.053

• wR(F ²) = 0.150

• S = 1.03

• 3365 reflections

• 157 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.39 e Å⁻³

• Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812001870/hg5164Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (4)	2.05 (4)	2.891 (4)	170 (3)

Symmetry code: (i) .

supplementary crystallographic information

Comment

Sulfonamide group containing drugs are extensively used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms (Korolkovas, 1988; Mandell & Sande, 1992). In continuation of our on going structural studies of cyclohexylamine and sulfonamides synthesis (John et al., 2010; Khan et al., 2010; Sharif et al., 2011), herein the crystal structure of title compound (I) is described.

In (I), (Fig. 1), the S atom has a distorted tetrahedral geometry within a CNO₂ donor set [maximum deviation: O—S—O = 119.45 (12)°]. The central C6–S1–N1–C7 torsion angle is -78.0 (2)°. The C7–C12 cyclohexyl ring adopts a chair conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.536 (4) Å, θ = 180.0 (4) °, φ = 196 (16) °.

In the crystal, two adjacent molecules are linked by a pair of N—H···O hydrogen bonds, forming an inversion dimer with an R₂²(8) ring motif (Table 1, Fig. 2).

Experimental

To 115 µl (1 mmol) of cyclohexylamine in 10 ml distilled water, was added 211 mg (1 mmol) of 4-chlorobenzenesulfonyl chloride while maintaining the pH of reaction mixture at 8 by using 3% sodium carbonate solution. Consumption of the reactants was confirmed by TLC. The pH of reaction mixture was adjusted by 3 N HCl at 3. Precipitates formed, washed with water and crystallized from methanol.

Refinement

The NH H–atom was located in a difference Fourier map and isotropically refined with a distance restraint: N—H = 0.86 (2) Å. C-bound H atoms were placed in calculated positions with C—H distances in the range 0.93–0.98 Å and and were refined using a riding model with U_iso(H) = 1.2U_eq(C). In the final refinement two low angle reflections evidently effected by the beam stop were omitted, i.e. 0 0 2 and 1 0 0.

Figures

Fig. 1.

The title molecule, showing the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Fig. 2.

The crystal packing of (I) down b axis, showing the molecules are linked into dimers by pairs of N—H ··· O hydrogen bonds, forming R22(8) graph-set motif. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C12H16ClNO2S	F(000) = 576
Mr = 273.78	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3062 reflections
a = 11.1226 (5) Å	θ = 2.6–21.6°
b = 6.2490 (2) Å	µ = 0.42 mm−1
c = 19.8635 (9) Å	T = 296 K
β = 96.505 (2)°	Needle, light brown
V = 1371.73 (10) Å3	0.29 × 0.15 × 0.11 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	2075 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.030
graphite	θmax = 28.3°, θmin = 3.4°
φ and ω scans	h = −14→14
12714 measured reflections	k = −6→8
3365 independent reflections	l = −26→26

Refinement

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.526P] where P = (Fo2 + 2Fc2)/3
3365 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.97047 (9)	0.63719 (19)	0.09885 (6)	0.1159 (5)
S1	0.67445 (5)	0.02579 (10)	0.26455 (3)	0.0538 (2)
O1	0.57744 (18)	−0.0412 (3)	0.21563 (11)	0.0788 (8)
O2	0.75531 (17)	−0.1301 (3)	0.29647 (11)	0.0710 (7)
N1	0.61305 (18)	0.1518 (3)	0.32146 (11)	0.0527 (7)
C1	0.7127 (2)	0.3981 (4)	0.19816 (13)	0.0581 (9)
C2	0.7777 (3)	0.5312 (4)	0.16141 (14)	0.0650 (9)
C3	0.8901 (3)	0.4698 (5)	0.14686 (14)	0.0654 (10)
C4	0.9396 (2)	0.2788 (5)	0.16961 (16)	0.0733 (11)
C5	0.8750 (2)	0.1454 (4)	0.20712 (14)	0.0606 (9)
C6	0.7611 (2)	0.2037 (4)	0.22098 (12)	0.0465 (7)
C7	0.6789 (2)	0.2145 (4)	0.38711 (12)	0.0541 (8)
C8	0.7329 (3)	0.4325 (5)	0.38666 (16)	0.0829 (11)
C9	0.7924 (4)	0.4979 (7)	0.45609 (18)	0.1069 (17)
C10	0.7084 (4)	0.4802 (9)	0.5084 (2)	0.117 (2)
C11	0.6528 (5)	0.2674 (10)	0.50951 (18)	0.135 (2)
C12	0.5920 (4)	0.1970 (7)	0.44002 (17)	0.1033 (16)
H1	0.63600	0.43810	0.20780	0.0700*
H1N	0.555 (3)	0.234 (6)	0.3060 (19)	0.1390*
H2	0.74580	0.66260	0.14640	0.0780*
H4	1.01630	0.23970	0.15970	0.0880*
H5	0.90830	0.01600	0.22310	0.0730*
H7	0.74450	0.11150	0.39850	0.0650*
H8A	0.67010	0.53500	0.37150	0.0990*
H8B	0.79270	0.43550	0.35470	0.0990*
H9A	0.86230	0.40740	0.46850	0.1280*
H9B	0.82060	0.64450	0.45420	0.1280*
H10A	0.75200	0.51000	0.55240	0.1410*
H10B	0.64520	0.58700	0.49970	0.1410*
H11A	0.59300	0.26840	0.54140	0.1620*
H11B	0.71460	0.16380	0.52540	0.1620*
H12A	0.56470	0.05020	0.44260	0.1240*
H12B	0.52180	0.28630	0.42710	0.1240*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0867 (7)	0.1367 (9)	0.1293 (9)	−0.0197 (6)	0.0339 (6)	0.0505 (7)
S1	0.0456 (4)	0.0438 (3)	0.0725 (4)	−0.0069 (3)	0.0087 (3)	−0.0065 (3)
O1	0.0634 (12)	0.0815 (13)	0.0904 (14)	−0.0310 (10)	0.0034 (11)	−0.0211 (11)
O2	0.0691 (12)	0.0436 (9)	0.1030 (15)	0.0083 (9)	0.0210 (11)	0.0082 (9)
N1	0.0393 (11)	0.0562 (12)	0.0629 (13)	0.0041 (9)	0.0071 (10)	0.0035 (10)
C1	0.0540 (15)	0.0589 (15)	0.0637 (16)	0.0058 (13)	0.0169 (13)	0.0006 (12)
C2	0.0704 (18)	0.0594 (15)	0.0664 (16)	0.0034 (14)	0.0132 (15)	0.0056 (13)
C3	0.0553 (16)	0.0765 (18)	0.0646 (16)	−0.0132 (15)	0.0076 (13)	0.0050 (14)
C4	0.0398 (14)	0.091 (2)	0.090 (2)	−0.0036 (15)	0.0118 (15)	0.0011 (18)
C5	0.0418 (14)	0.0602 (15)	0.0793 (18)	0.0021 (12)	0.0048 (13)	0.0025 (13)
C6	0.0410 (12)	0.0461 (12)	0.0514 (13)	−0.0033 (10)	0.0015 (10)	−0.0093 (10)
C7	0.0463 (14)	0.0565 (14)	0.0597 (15)	0.0112 (12)	0.0063 (12)	0.0059 (12)
C8	0.095 (2)	0.082 (2)	0.0727 (19)	−0.0204 (19)	0.0134 (18)	−0.0077 (16)
C9	0.106 (3)	0.119 (3)	0.095 (3)	−0.014 (2)	0.009 (2)	−0.038 (2)
C10	0.092 (3)	0.178 (5)	0.082 (2)	0.019 (3)	0.009 (2)	−0.049 (3)
C11	0.132 (4)	0.216 (6)	0.059 (2)	−0.014 (4)	0.018 (2)	0.022 (3)
C12	0.100 (3)	0.141 (3)	0.072 (2)	−0.027 (2)	0.023 (2)	0.021 (2)

Geometric parameters (Å, °)

Cl1—C3	1.731 (4)	C10—C11	1.468 (8)
S1—O1	1.431 (2)	C11—C12	1.531 (6)
S1—O2	1.425 (2)	C1—H1	0.9300
S1—N1	1.594 (2)	C2—H2	0.9300
S1—C6	1.762 (3)	C4—H4	0.9300
N1—C7	1.475 (3)	C5—H5	0.9300
N1—H1N	0.85 (4)	C7—H7	0.9800
C1—C2	1.366 (4)	C8—H8A	0.9700
C1—C6	1.384 (4)	C8—H8B	0.9700
C2—C3	1.370 (5)	C9—H9A	0.9700
C3—C4	1.370 (4)	C9—H9B	0.9700
C4—C5	1.374 (4)	C10—H10A	0.9700
C5—C6	1.376 (3)	C10—H10B	0.9700
C7—C12	1.510 (5)	C11—H11A	0.9700
C7—C8	1.489 (4)	C11—H11B	0.9700
C8—C9	1.517 (5)	C12—H12A	0.9700
C9—C10	1.478 (6)	C12—H12B	0.9700
O1—S1—O2	119.45 (12)	C5—C4—H4	120.00
O1—S1—N1	106.00 (12)	C4—C5—H5	120.00
O1—S1—C6	105.28 (12)	C6—C5—H5	120.00
O2—S1—N1	108.77 (12)	N1—C7—H7	108.00
O2—S1—C6	107.29 (11)	C8—C7—H7	108.00
N1—S1—C6	109.82 (11)	C12—C7—H7	108.00
S1—N1—C7	123.29 (16)	C7—C8—H8A	109.00
S1—N1—H1N	114 (3)	C7—C8—H8B	109.00
C7—N1—H1N	116 (3)	C9—C8—H8A	109.00
C2—C1—C6	120.0 (2)	C9—C8—H8B	109.00
C1—C2—C3	119.6 (3)	H8A—C8—H8B	108.00
Cl1—C3—C2	119.2 (2)	C8—C9—H9A	109.00
C2—C3—C4	121.1 (3)	C8—C9—H9B	109.00
Cl1—C3—C4	119.7 (2)	C10—C9—H9A	109.00
C3—C4—C5	119.5 (2)	C10—C9—H9B	109.00
C4—C5—C6	119.9 (2)	H9A—C9—H9B	108.00
S1—C6—C1	120.05 (17)	C9—C10—H10A	109.00
S1—C6—C5	119.92 (19)	C9—C10—H10B	109.00
C1—C6—C5	120.0 (2)	C11—C10—H10A	109.00
N1—C7—C8	113.5 (2)	C11—C10—H10B	109.00
C8—C7—C12	111.2 (3)	H10A—C10—H10B	108.00
N1—C7—C12	107.7 (2)	C10—C11—H11A	109.00
C7—C8—C9	112.1 (3)	C10—C11—H11B	109.00
C8—C9—C10	111.9 (4)	C12—C11—H11A	109.00
C9—C10—C11	112.3 (4)	C12—C11—H11B	109.00
C10—C11—C12	113.0 (4)	H11A—C11—H11B	108.00
C7—C12—C11	110.8 (4)	C7—C12—H12A	110.00
C2—C1—H1	120.00	C7—C12—H12B	109.00
C6—C1—H1	120.00	C11—C12—H12A	109.00
C1—C2—H2	120.00	C11—C12—H12B	109.00
C3—C2—H2	120.00	H12A—C12—H12B	108.00
C3—C4—H4	120.00
O1—S1—N1—C7	168.78 (18)	C1—C2—C3—Cl1	178.7 (2)
O2—S1—N1—C7	39.2 (2)	Cl1—C3—C4—C5	−179.3 (2)
C6—S1—N1—C7	−78.0 (2)	C2—C3—C4—C5	0.6 (5)
N1—S1—C6—C5	135.6 (2)	C3—C4—C5—C6	0.6 (4)
O2—S1—C6—C1	−165.3 (2)	C4—C5—C6—S1	176.1 (2)
N1—S1—C6—C1	−47.2 (2)	C4—C5—C6—C1	−1.1 (4)
O1—S1—C6—C1	66.5 (2)	N1—C7—C8—C9	176.1 (3)
O2—S1—C6—C5	17.5 (2)	C12—C7—C8—C9	54.6 (4)
O1—S1—C6—C5	−110.7 (2)	N1—C7—C12—C11	−178.0 (3)
S1—N1—C7—C12	−144.8 (2)	C8—C7—C12—C11	−53.2 (4)
S1—N1—C7—C8	91.8 (2)	C7—C8—C9—C10	−54.4 (4)
C6—C1—C2—C3	0.7 (4)	C8—C9—C10—C11	53.3 (5)
C2—C1—C6—S1	−176.7 (2)	C9—C10—C11—C12	−53.2 (6)
C2—C1—C6—C5	0.5 (4)	C10—C11—C12—C7	53.0 (5)
C1—C2—C3—C4	−1.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (4)	2.05 (4)	2.891 (4)	170 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2.