4-Chloro-N-cyclo­hexyl­benzene­sulfonamide

Sharif, S.; Mughal, S.Y.; Khan, I.U.; Akkurt, M.; Khan, M.H.

doi:10.1107/S1600536812001870

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o468

doi:10.1107/S1600536812001870

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4-Chloro-N-cyclohexylbenzenesulfonamide

Shahzad Sharif,^a Shumaila Younas Mughal,^a Islam Ullah Khan,^a Mehmet Akkurt ^b ^* and Muneeb Hayat Khan ^c

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and, Pakistan and Punjab Forensic Science Agency, Thokar Niaz Baig, Lahore, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr, iukhan@gcu.edu.pk

(Received 13 January 2012; accepted 16 January 2012; online 21 January 2012)

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 R₂²(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, P 2₁ /c
a = 11.1226 (5) Å
b = 6.2490 (2) Å
c = 19.8635 (9) Å
β = 96.505 (2)°
V = 1371.73 (10) Å³
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[F² > 2σ(F²)] = 0.053
wR(F²) = 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

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001870/hg5164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001870/hg5164Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001870/hg5164Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	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.

4-Chloro-N-cyclohexylbenzenesulfonamide top

Crystal data top

C₁₂H₁₆ClNO₂S	F(000) = 576
M_r = 273.78	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0613P)² + 0.526P] where P = (F_o² + 2F_c²)/3
3365 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₂H₁₆ClNO₂S	V = 1371.73 (10) Å³
M_r = 273.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1226 (5) Å	µ = 0.42 mm⁻¹
b = 6.2490 (2) Å	T = 296 K
c = 19.8635 (9) Å	0.29 × 0.15 × 0.11 mm
β = 96.505 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2075 reflections with I > 2σ(I)
12714 measured reflections	R_int = 0.030
3365 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.39 e Å⁻³
3365 reflections	Δρ_min = −0.25 e Å⁻³
157 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆ClNO₂S
M_r	273.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.1226 (5), 6.2490 (2), 19.8635 (9)
β (°)	96.505 (2)
V (Å³)	1371.73 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.29 × 0.15 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12714, 3365, 2075
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.03
No. of reflections	3365
No. of parameters	157
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University Lahore.

References

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