2,5-Dichloro-N-cyclo­hexyl­benzene­sulfonamide

Khan, I.U.; Sharif, S.; Batool, S.; Mumtaz, A.M.; Tiekink, E.R.T.

doi:10.1107/S160053681003789X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2641

doi:10.1107/S160053681003789X

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2,5-Dichloro-N-cyclohexylbenzenesulfonamide

Islam Ullah Khan,^a ‡ Shahzad Sharif,^a Shumaila Batool,^a Ahmad Mahmood Mumtaz ^b and Edward R. T. Tiekink ^c ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College, University, Lahore 54000, Pakistan, ^bResearch & Development Drugs Wing, Ministry of Health, Islamabad 44000, Pakistan, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 21 September 2010; accepted 22 September 2010; online 25 September 2010)

The structure of the title sulfonamide, C₁₂H₁₅Cl₂NO₂S, features a distorted tetrahedral geometry for the S atom [maximum deviation: O—S—O = 120.23 (14)°]. One of the sulfonamide O atoms is coplanar with the benzene ring [C—C—S—O torsion angle = −174.5 (2)°], whereas the other lies well above the plane [C—C—S—O = 57.0 (3)°]. A chair conformation is found for the cyclohexyl ring. In the crystal, supramolecular chains aligned along the c axis are formed via N—H⋯O hydrogen bonds; these are consolidated in the three-dimensional packing by C—H⋯O contacts involving the second sulfonamide O atom.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ); Mandell & Sande (1992 ). For related structures, see: Khan et al. (2010 ); Sharif et al. (2010 ).

Experimental

Crystal data

C₁₂H₁₅Cl₂NO₂S
M_r = 308.21
Monoclinic, C c
a = 17.4471 (12) Å
b = 10.7574 (8) Å
c = 8.2845 (6) Å
β = 111.956 (4)°
V = 1442.11 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 293 K
0.28 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.692, T_max = 0.895
6491 measured reflections
2983 independent reflections
2492 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.092
S = 1.01
2983 reflections
166 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1327 Friedel pairs
Flack parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2ⁱ	0.88 (2)	2.08 (2)	2.914 (3)	157 (2)
C4—H4⋯O1ⁱⁱ	0.93	2.60	3.246 (4)	127
Symmetry codes: (i) $[x, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003789X/hg2717sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681003789X/hg2717Isup2.hkl

checkCIF report

Comment top

Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988; Mandell & Sande, 1992). In continuation of on-going structural studies of sulfonamide derivatives (Khan et al., 2010, Sharif et al., 2010), the crystal structure of title sulfonamide, (I), is described herein.

In (I), the S atom is tetrahedrally coordinated within a CNO₂ donor set with the greatest deviation manifested in the O1—S1—O2 angle of 120.23 (14) °. Whereas the sulfonamide-O1 atom is co-planar with the benzene ring [the O1—S1—C1—C2 torsion angle = -174.5 (2) °], the O2 atom lies well above the plane [O2—S1—C1—C2 = 57.0 (3) °]. The amide-H lies to the same side of the molecule as does the ortho-substituted Cl atom and approaches this atom at 2.85 (3) Å. The cyclohexyl ring adopts a chair conformation.

The presence of N1—H···O2 hydrogen bonding, Table 1, leads to the formation of supramolecular chains along the c axis, Fig. 2. Chains are consolidated in the 3-D packing by C4—H···O1 interactions, Fig. 3 and Table 1.

Related literature top

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992). For related structures, see: Khan et al. (2010); Sharif et al. (2010).

Experimental top

To 2,5-dichlorobenzenesulfonyl chloride (491 mg, 2 mmol) in 10 ml distilled water, was added cyclohexylamine (229 µl, 2 mmol) with stirring at room temperature while maintaining the pH of reaction mixture at 8 by using 3% sodium carbonate solution. The progress of reaction was monitored by TLC. After consumption of reactants, the precipitates were filtered, dried 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular chain formation along c in (I) mediated by N—H···O hydrogen bonding (orange dashed lines).
	Fig. 3. Unit-cell contents shown in projection down the c axis in (I). N—H···O hydrogen bonds (orange dashed lines) down the c axis are largely obscured. The C–H···O contacts are shown as blue dashed lines.

2,5-Dichloro-N-cyclohexylbenzenesulfonamide top

Crystal data top

C₁₂H₁₅Cl₂NO₂S	F(000) = 640
M_r = 308.21	D_x = 1.420 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2154 reflections
a = 17.4471 (12) Å	θ = 2.3–25.8°
b = 10.7574 (8) Å	µ = 0.59 mm⁻¹
c = 8.2845 (6) Å	T = 293 K
β = 111.956 (4)°	Block, colourless
V = 1442.11 (18) Å³	0.28 × 0.14 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.692, T_max = 0.895	k = −13→10
6491 measured reflections	l = −10→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0499P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2983 reflections	Δρ_max = 0.24 e Å⁻³
166 parameters	Δρ_min = −0.19 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1327 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (7)

Crystal data top

C₁₂H₁₅Cl₂NO₂S	V = 1442.11 (18) Å³
M_r = 308.21	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 17.4471 (12) Å	µ = 0.59 mm⁻¹
b = 10.7574 (8) Å	T = 293 K
c = 8.2845 (6) Å	0.28 × 0.14 × 0.08 mm
β = 111.956 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2983 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2492 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.895	R_int = 0.029
6491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	Δρ_max = 0.24 e Å⁻³
S = 1.01	Δρ_min = −0.19 e Å⁻³
2983 reflections	Absolute structure: Flack (1983), 1327 Friedel pairs
166 parameters	Absolute structure parameter: 0.06 (7)
3 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.74062 (5)	0.95016 (10)	0.40157 (10)	0.0731 (3)
Cl2	0.71411 (6)	0.53058 (11)	0.89049 (15)	0.0905 (4)
S1	0.90528 (4)	0.86294 (6)	0.72894 (8)	0.04118 (17)
O1	0.96062 (11)	0.7885 (2)	0.8655 (3)	0.0571 (6)
O2	0.89603 (14)	0.99251 (19)	0.7564 (3)	0.0608 (6)
N1	0.93057 (15)	0.8530 (2)	0.5645 (3)	0.0457 (6)
H1n	0.9127 (18)	0.912 (2)	0.486 (3)	0.055*
C1	0.80608 (14)	0.7947 (2)	0.6796 (3)	0.0373 (6)
C2	0.73570 (17)	0.8342 (3)	0.5422 (4)	0.0448 (7)
C3	0.66045 (17)	0.7810 (3)	0.5144 (4)	0.0540 (8)
H3	0.6137	0.8089	0.4232	0.065*
C4	0.65355 (18)	0.6871 (3)	0.6199 (4)	0.0533 (7)
H4	0.6027	0.6499	0.5995	0.064*
C5	0.72223 (19)	0.6489 (3)	0.7549 (4)	0.0510 (7)
C6	0.79885 (17)	0.7007 (3)	0.7871 (3)	0.0436 (6)
H6	0.8450	0.6729	0.8798	0.052*
C7	0.96379 (16)	0.7403 (2)	0.5145 (4)	0.0392 (6)
H7	0.9751	0.6793	0.6085	0.047*
C8	0.90286 (18)	0.6836 (3)	0.3500 (4)	0.0550 (8)
H8A	0.8874	0.7450	0.2575	0.066*
H8B	0.8533	0.6593	0.3689	0.066*
C9	0.9399 (2)	0.5697 (3)	0.2951 (5)	0.0608 (9)
H9A	0.9499	0.5050	0.3821	0.073*
H9B	0.9008	0.5379	0.1858	0.073*
C10	1.0206 (2)	0.6020 (3)	0.2741 (4)	0.0624 (9)
H10A	1.0442	0.5274	0.2457	0.075*
H10B	1.0099	0.6605	0.1791	0.075*
C11	1.0810 (2)	0.6580 (3)	0.4394 (4)	0.0564 (8)
H11A	1.1308	0.6823	0.4216	0.068*
H11B	1.0961	0.5961	0.5313	0.068*
C12	1.04439 (17)	0.7717 (3)	0.4958 (4)	0.0471 (7)
H12A	1.0834	0.8022	0.6061	0.056*
H12B	1.0352	0.8372	0.4101	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0545 (5)	0.0915 (7)	0.0708 (6)	0.0203 (4)	0.0206 (4)	0.0393 (5)
Cl2	0.0742 (6)	0.0882 (7)	0.1198 (9)	0.0010 (5)	0.0486 (6)	0.0425 (6)
S1	0.0346 (3)	0.0513 (4)	0.0368 (3)	−0.0019 (3)	0.0124 (2)	−0.0063 (3)
O1	0.0349 (10)	0.0900 (16)	0.0400 (11)	−0.0033 (10)	0.0066 (9)	0.0081 (10)
O2	0.0674 (14)	0.0549 (12)	0.0639 (14)	−0.0091 (11)	0.0290 (11)	−0.0221 (11)
N1	0.0516 (14)	0.0457 (14)	0.0473 (14)	0.0123 (10)	0.0273 (12)	0.0108 (10)
C1	0.0318 (12)	0.0465 (15)	0.0337 (13)	0.0026 (11)	0.0122 (10)	−0.0074 (11)
C2	0.0385 (14)	0.0551 (17)	0.0391 (15)	0.0093 (12)	0.0127 (12)	0.0014 (13)
C3	0.0327 (13)	0.076 (2)	0.0446 (18)	0.0084 (15)	0.0045 (13)	−0.0017 (15)
C4	0.0370 (15)	0.0645 (19)	0.0588 (18)	−0.0071 (14)	0.0183 (14)	−0.0115 (16)
C5	0.0482 (17)	0.0492 (18)	0.0612 (18)	0.0026 (13)	0.0267 (15)	0.0045 (15)
C6	0.0366 (14)	0.0536 (17)	0.0415 (15)	0.0052 (12)	0.0155 (12)	0.0037 (13)
C7	0.0409 (13)	0.0369 (14)	0.0438 (15)	0.0050 (11)	0.0204 (12)	0.0045 (11)
C8	0.0445 (16)	0.0543 (18)	0.0625 (19)	−0.0063 (13)	0.0159 (14)	−0.0042 (15)
C9	0.070 (2)	0.0468 (18)	0.0565 (19)	−0.0033 (15)	0.0132 (17)	−0.0089 (14)
C10	0.084 (2)	0.0563 (18)	0.0522 (19)	0.0169 (17)	0.0323 (18)	−0.0001 (15)
C11	0.0528 (17)	0.066 (2)	0.061 (2)	0.0148 (15)	0.0330 (16)	0.0026 (16)
C12	0.0381 (14)	0.0541 (17)	0.0512 (16)	0.0005 (12)	0.0192 (13)	−0.0029 (13)

Geometric parameters (Å, º) top

Cl1—C2	1.731 (3)	C7—C8	1.508 (4)
Cl2—C5	1.738 (3)	C7—C12	1.510 (4)
S1—O1	1.427 (2)	C7—H7	0.9800
S1—O2	1.431 (2)	C8—C9	1.532 (5)
S1—N1	1.585 (2)	C8—H8A	0.9700
S1—C1	1.781 (3)	C8—H8B	0.9700
N1—C7	1.469 (3)	C9—C10	1.521 (5)
N1—H1n	0.88 (2)	C9—H9A	0.9700
C1—C6	1.384 (4)	C9—H9B	0.9700
C1—C2	1.392 (3)	C10—C11	1.507 (5)
C2—C3	1.370 (4)	C10—H10A	0.9700
C3—C4	1.371 (5)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.531 (4)
C4—C5	1.362 (4)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.379 (4)	C12—H12A	0.9700
C6—H6	0.9300	C12—H12B	0.9700

O1—S1—O2	120.23 (14)	C12—C7—H7	108.2
O1—S1—N1	108.69 (13)	C7—C8—C9	111.0 (2)
O2—S1—N1	106.64 (13)	C7—C8—H8A	109.4
O1—S1—C1	105.20 (13)	C9—C8—H8A	109.4
O2—S1—C1	106.27 (13)	C7—C8—H8B	109.4
N1—S1—C1	109.51 (13)	C9—C8—H8B	109.4
C7—N1—S1	124.32 (19)	H8A—C8—H8B	108.0
C7—N1—H1N	117 (2)	C10—C9—C8	111.3 (3)
S1—N1—H1N	117 (2)	C10—C9—H9A	109.4
C6—C1—C2	119.0 (2)	C8—C9—H9A	109.4
C6—C1—S1	117.89 (19)	C10—C9—H9B	109.4
C2—C1—S1	123.1 (2)	C8—C9—H9B	109.4
C3—C2—C1	120.4 (3)	H9A—C9—H9B	108.0
C3—C2—Cl1	118.2 (2)	C11—C10—C9	110.5 (3)
C1—C2—Cl1	121.3 (2)	C11—C10—H10A	109.6
C2—C3—C4	120.5 (3)	C9—C10—H10A	109.6
C2—C3—H3	119.7	C11—C10—H10B	109.6
C4—C3—H3	119.7	C9—C10—H10B	109.6
C5—C4—C3	119.1 (3)	H10A—C10—H10B	108.1
C5—C4—H4	120.4	C10—C11—C12	111.5 (3)
C3—C4—H4	120.4	C10—C11—H11A	109.3
C4—C5—C6	121.9 (3)	C12—C11—H11A	109.3
C4—C5—Cl2	119.5 (2)	C10—C11—H11B	109.3
C6—C5—Cl2	118.6 (2)	C12—C11—H11B	109.3
C5—C6—C1	119.1 (3)	H11A—C11—H11B	108.0
C5—C6—H6	120.5	C7—C12—C11	111.3 (3)
C1—C6—H6	120.5	C7—C12—H12A	109.4
N1—C7—C8	111.7 (2)	C11—C12—H12A	109.4
N1—C7—C12	109.0 (2)	C7—C12—H12B	109.4
C8—C7—C12	111.5 (2)	C11—C12—H12B	109.4
N1—C7—H7	108.2	H12A—C12—H12B	108.0
C8—C7—H7	108.2

O1—S1—N1—C7	34.9 (3)	C3—C4—C5—C6	−1.0 (5)
O2—S1—N1—C7	165.9 (2)	C3—C4—C5—Cl2	179.6 (2)
C1—S1—N1—C7	−79.5 (2)	C4—C5—C6—C1	0.4 (4)
O1—S1—C1—C6	7.6 (2)	Cl2—C5—C6—C1	179.8 (2)
O2—S1—C1—C6	−120.9 (2)	C2—C1—C6—C5	0.1 (4)
N1—S1—C1—C6	124.3 (2)	S1—C1—C6—C5	178.1 (2)
O1—S1—C1—C2	−174.5 (2)	S1—N1—C7—C8	110.4 (3)
O2—S1—C1—C2	57.0 (3)	S1—N1—C7—C12	−126.0 (2)
N1—S1—C1—C2	−57.8 (2)	N1—C7—C8—C9	177.4 (3)
C6—C1—C2—C3	0.2 (4)	C12—C7—C8—C9	55.2 (4)
S1—C1—C2—C3	−177.7 (2)	C7—C8—C9—C10	−55.8 (4)
C6—C1—C2—Cl1	−179.3 (2)	C8—C9—C10—C11	56.1 (4)
S1—C1—C2—Cl1	2.8 (3)	C9—C10—C11—C12	−55.8 (4)
C1—C2—C3—C4	−0.9 (4)	N1—C7—C12—C11	−178.7 (2)
Cl1—C2—C3—C4	178.6 (2)	C8—C7—C12—C11	−55.0 (3)
C2—C3—C4—C5	1.3 (5)	C10—C11—C12—C7	55.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2ⁱ	0.88 (2)	2.08 (2)	2.914 (3)	157 (2)
C4—H4···O1ⁱⁱ	0.93	2.60	3.246 (4)	127

Symmetry codes: (i) x, −y+2, z−1/2; (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅Cl₂NO₂S
M_r	308.21
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	17.4471 (12), 10.7574 (8), 8.2845 (6)
β (°)	111.956 (4)
V (Å³)	1442.11 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.28 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.692, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	6491, 2983, 2492
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.092, 1.01
No. of reflections	2983
No. of parameters	166
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19
Absolute structure	Flack (1983), 1327 Friedel pairs
Absolute structure parameter	0.06 (7)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2ⁱ	0.88 (2)	2.08 (2)	2.914 (3)	157 (2)
C4—H4···O1ⁱⁱ	0.93	2.60	3.246 (4)	127

Symmetry codes: (i) x, −y+2, z−1/2; (ii) x−1/2, −y+3/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: iuklodhi@yahoo.com.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

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