2,5-Dichloro-N-(4-meth­oxy­phen­yl)benzensulfonamide

Khan, I.U.; Bibi, S.; Mariam, I.; Sharif, S.; Kang, S.K.

doi:10.1107/S1600536811000936

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o369

doi:10.1107/S1600536811000936

Open

access

2,5-Dichloro-N-(4-methoxyphenyl)benzensulfonamide

Islam Ullah Khan,^a Sajida Bibi,^a Irfana Mariam,^a Shahzad Sharif ^a and Sung Kwon Kang ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

(Received 3 January 2011; accepted 7 January 2011; online 12 January 2011)

In the title compound, C₁₃H₁₁Cl₂NO₃S, the dihedral angle between the benzene rings is 74.37 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the b axis.

Related literature

For our previous studies on sulfonamide derivatives, see: Khan et al. (2010 ); Sharif et al. (2010 ). For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ); Mandell & Sande (1992 ).

Experimental

Crystal data

C₁₃H₁₁Cl₂NO₃S
M_r = 332.19
Monoclinic, P 2₁ /c
a = 13.1599 (4) Å
b = 7.8179 (2) Å
c = 14.4830 (5) Å
β = 110.566 (1)°
V = 1395.09 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 296 K
0.25 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
13132 measured reflections
3456 independent reflections
2690 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.06
3456 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12⋯O19ⁱ	0.78 (2)	2.50 (3)	3.267 (2)	168 (2)
Symmetry code: (i) x, y+1, z.

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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000936/jh2254sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000936/jh2254Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of sulfonamides synthesis (Khan et al., 2010; Sharif et al., 2010), of interest owing to their biological properties (Korolkovas, 1988; Mandell & Sande, 1992). Herein, the crystal structure of (I) is described

In the title compound (I), (Fig. 1), the 4-methoxyphenyl moiety is almost planar with r.m.s. deviation of 0.018 Å from the corresponding least-squares plane defined by the nine constituent atoms. The dihedral angle between the benzene rings is 74.37 (3) °. In the crystal, intermolecular N—H···O hydrogen bonds link the molecules into chains along the b axis (Table 1, Fig. 2).

Related literature top

For our previous studies on sulfonamide derivatives, see: Khan et al. (2010); Sharif et al. (2010). For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992).

Experimental top

To para-anisidine (123 mg, 1 mmol) in distilled water (10 ml) was added 2,5-dichloro benzene sulfonyl chloride (0.245 mg, 1 mmol) with stirring at room temperature while maintaining the pH = 8 using 3% sodium carbonate. The progress of the reaction was monitored by TLC. The precipitate formed in this way was washed with water, 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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-numbering scheme and 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure of (I), showing chain of molecules linked by intermolecular N—H···O hydrogen bonds (dashed lines) along the b axis.

2,5-Dichloro-N-(4-methoxyphenyl)benzensulfonamide top

Crystal data top

C₁₃H₁₁Cl₂NO₃S	F(000) = 680
M_r = 332.19	D_x = 1.582 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4792 reflections
a = 13.1599 (4) Å	θ = 2.9–28.0°
b = 7.8179 (2) Å	µ = 0.62 mm⁻¹
c = 14.4830 (5) Å	T = 296 K
β = 110.566 (1)°	Block, colourless
V = 1395.09 (7) Å³	0.25 × 0.17 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.030
ϕ and ω scans	θ_max = 28.3°, θ_min = 3.0°
13132 measured reflections	h = −17→17
3456 independent reflections	k = −10→10
2690 reflections with I > 2σ(I)	l = −18→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.045P)² + 0.6614P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.108	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.46 e Å⁻³
3456 reflections	Δρ_min = −0.31 e Å⁻³
186 parameters

Crystal data top

C₁₃H₁₁Cl₂NO₃S	V = 1395.09 (7) Å³
M_r = 332.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1599 (4) Å	µ = 0.62 mm⁻¹
b = 7.8179 (2) Å	T = 296 K
c = 14.4830 (5) Å	0.25 × 0.17 × 0.12 mm
β = 110.566 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2690 reflections with I > 2σ(I)
13132 measured reflections	R_int = 0.030
3456 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.46 e Å⁻³
3456 reflections	Δρ_min = −0.31 e Å⁻³
186 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.72780 (4)	0.85926 (6)	0.82650 (3)	0.03916 (14)
O2	0.73299 (14)	1.04147 (19)	0.82443 (12)	0.0552 (4)
O3	0.69500 (12)	0.7655 (2)	0.73648 (10)	0.0493 (4)
C4	0.85981 (16)	0.7804 (2)	0.89567 (14)	0.0369 (4)
C5	0.91579 (17)	0.8160 (3)	0.99528 (15)	0.0419 (4)
C6	1.02137 (18)	0.7615 (3)	1.03996 (17)	0.0509 (5)
H6	1.0576	0.7843	1.1065	0.061*
C7	1.07387 (19)	0.6737 (3)	0.98749 (18)	0.0539 (6)
H7	1.1455	0.6385	1.0176	0.065*
C8	1.01785 (18)	0.6389 (3)	0.88887 (17)	0.0485 (5)
C9	0.91210 (17)	0.6898 (3)	0.84328 (15)	0.0427 (4)
H9	0.8756	0.6635	0.7772	0.051*
Cl10	0.85599 (5)	0.93075 (8)	1.06480 (4)	0.05536 (17)
Cl11	1.08144 (6)	0.53037 (11)	0.82003 (6)	0.0786 (2)
N12	0.64500 (14)	0.8123 (2)	0.88365 (13)	0.0398 (4)
H12	0.6441 (19)	0.888 (3)	0.9181 (17)	0.046 (7)*
C13	0.63424 (15)	0.6413 (2)	0.91467 (13)	0.0350 (4)
C14	0.65129 (17)	0.6093 (3)	1.01225 (14)	0.0412 (4)
H14	0.6706	0.6986	1.0575	0.049*
C15	0.64003 (17)	0.4456 (3)	1.04402 (15)	0.0423 (5)
H15	0.6504	0.4257	1.11	0.051*
C16	0.61338 (16)	0.3123 (3)	0.97760 (15)	0.0405 (4)
C17	0.59349 (19)	0.3448 (3)	0.87865 (15)	0.0476 (5)
H17	0.5737	0.2557	0.8333	0.057*
C18	0.60287 (18)	0.5083 (3)	0.84720 (15)	0.0448 (5)
H18	0.5881	0.5295	0.7806	0.054*
O19	0.60296 (14)	0.1448 (2)	1.00210 (12)	0.0560 (4)
C20	0.6237 (2)	0.1095 (3)	1.10353 (19)	0.0610 (6)
H20A	0.6977	0.138	1.1414	0.091*
H20B	0.6117	−0.0098	1.1116	0.091*
H20C	0.5759	0.1765	1.126	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0448 (3)	0.0397 (3)	0.0347 (2)	0.0049 (2)	0.0162 (2)	0.00713 (19)
O2	0.0669 (10)	0.0399 (8)	0.0638 (10)	0.0066 (7)	0.0292 (9)	0.0140 (7)
O3	0.0502 (8)	0.0672 (10)	0.0303 (7)	0.0043 (7)	0.0137 (6)	0.0024 (7)
C4	0.0414 (10)	0.0341 (9)	0.0361 (9)	−0.0023 (8)	0.0147 (8)	0.0044 (7)
C5	0.0504 (11)	0.0387 (10)	0.0371 (10)	−0.0093 (9)	0.0158 (9)	0.0011 (8)
C6	0.0489 (12)	0.0532 (13)	0.0423 (11)	−0.0122 (10)	0.0056 (10)	0.0042 (10)
C7	0.0414 (11)	0.0580 (14)	0.0583 (14)	−0.0021 (10)	0.0128 (10)	0.0121 (11)
C8	0.0474 (12)	0.0490 (12)	0.0533 (12)	0.0055 (9)	0.0231 (10)	0.0097 (10)
C9	0.0471 (11)	0.0426 (11)	0.0404 (10)	0.0018 (9)	0.0178 (9)	0.0049 (8)
Cl10	0.0707 (4)	0.0531 (3)	0.0446 (3)	−0.0098 (3)	0.0231 (3)	−0.0122 (2)
Cl11	0.0661 (4)	0.1040 (6)	0.0740 (5)	0.0343 (4)	0.0349 (4)	0.0095 (4)
N12	0.0480 (10)	0.0371 (9)	0.0386 (9)	0.0037 (7)	0.0205 (8)	−0.0011 (7)
C13	0.0340 (9)	0.0368 (10)	0.0363 (9)	0.0017 (7)	0.0151 (8)	−0.0002 (8)
C14	0.0475 (11)	0.0427 (11)	0.0356 (10)	−0.0059 (8)	0.0175 (9)	−0.0070 (8)
C15	0.0475 (11)	0.0487 (12)	0.0332 (10)	−0.0065 (9)	0.0172 (9)	−0.0002 (8)
C16	0.0415 (10)	0.0391 (10)	0.0427 (11)	−0.0018 (8)	0.0171 (9)	0.0011 (8)
C17	0.0629 (13)	0.0414 (11)	0.0390 (11)	−0.0044 (9)	0.0185 (10)	−0.0090 (9)
C18	0.0574 (13)	0.0449 (11)	0.0312 (9)	−0.0003 (9)	0.0146 (9)	−0.0023 (8)
O19	0.0776 (11)	0.0403 (8)	0.0550 (9)	−0.0060 (7)	0.0290 (8)	0.0021 (7)
C20	0.0800 (17)	0.0519 (14)	0.0613 (15)	0.0073 (12)	0.0377 (13)	0.0149 (12)

Geometric parameters (Å, º) top

S1—O3	1.4243 (15)	N12—H12	0.78 (2)
S1—O2	1.4269 (16)	C13—C14	1.374 (3)
S1—N12	1.6250 (17)	C13—C18	1.387 (3)
S1—C4	1.783 (2)	C14—C15	1.386 (3)
C4—C9	1.385 (3)	C14—H14	0.93
C4—C5	1.398 (3)	C15—C16	1.377 (3)
C5—C6	1.378 (3)	C15—H15	0.93
C5—Cl10	1.731 (2)	C16—O19	1.376 (2)
C6—C7	1.377 (3)	C16—C17	1.387 (3)
C6—H6	0.93	C17—C18	1.377 (3)
C7—C8	1.385 (3)	C17—H17	0.93
C7—H7	0.93	C18—H18	0.93
C8—C9	1.373 (3)	O19—C20	1.424 (3)
C8—Cl11	1.732 (2)	C20—H20A	0.96
C9—H9	0.93	C20—H20B	0.96
N12—C13	1.433 (3)	C20—H20C	0.96

O3—S1—O2	119.74 (10)	S1—N12—H12	108.5 (18)
O3—S1—N12	107.95 (10)	C14—C13—C18	119.27 (18)
O2—S1—N12	106.36 (10)	C14—C13—N12	119.59 (17)
O3—S1—C4	104.98 (9)	C18—C13—N12	121.09 (17)
O2—S1—C4	108.22 (10)	C13—C14—C15	120.78 (18)
N12—S1—C4	109.34 (9)	C13—C14—H14	119.6
C9—C4—C5	118.95 (19)	C15—C14—H14	119.6
C9—C4—S1	116.27 (15)	C16—C15—C14	119.84 (18)
C5—C4—S1	124.56 (16)	C16—C15—H15	120.1
C6—C5—C4	120.1 (2)	C14—C15—H15	120.1
C6—C5—Cl10	118.46 (17)	O19—C16—C15	124.31 (18)
C4—C5—Cl10	121.40 (16)	O19—C16—C17	116.17 (18)
C7—C6—C5	120.9 (2)	C15—C16—C17	119.51 (19)
C7—C6—H6	119.5	C18—C17—C16	120.37 (19)
C5—C6—H6	119.5	C18—C17—H17	119.8
C6—C7—C8	118.6 (2)	C16—C17—H17	119.8
C6—C7—H7	120.7	C17—C18—C13	120.14 (18)
C8—C7—H7	120.7	C17—C18—H18	119.9
C9—C8—C7	121.4 (2)	C13—C18—H18	119.9
C9—C8—Cl11	118.56 (18)	C16—O19—C20	116.76 (18)
C7—C8—Cl11	120.00 (18)	O19—C20—H20A	109.5
C8—C9—C4	120.0 (2)	O19—C20—H20B	109.5
C8—C9—H9	120	H20A—C20—H20B	109.5
C4—C9—H9	120	O19—C20—H20C	109.5
C13—N12—S1	121.87 (14)	H20A—C20—H20C	109.5
C13—N12—H12	119.1 (18)	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O19ⁱ	0.78 (2)	2.50 (3)	3.267 (2)	168 (2)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁Cl₂NO₃S
M_r	332.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.1599 (4), 7.8179 (2), 14.4830 (5)
β (°)	110.566 (1)
V (Å³)	1395.09 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.25 × 0.17 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13132, 3456, 2690
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.06
No. of reflections	3456
No. of parameters	186
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O19ⁱ	0.78 (2)	2.50 (3)	3.267 (2)	168 (2)

Symmetry code: (i) x, y+1, z.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Khan, I. U., Akkurt, M., Sharif, S. & Ahmad, W. (2010). Acta Cryst. E66, o3053. Web of Science CSD CrossRef IUCr Journals Google Scholar
Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed., pp. 699–716. New York: Wiley. Google Scholar
Mandell, G. L. & Sande, M. A. (1992). Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047–1057. Singapore: McGraw-Hill. Google Scholar
Sharif, S., Iqbal, H., Khan, I. U., John, P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1288. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o369

doi:10.1107/S1600536811000936

Open

access