2,5-Dichloro-N-(4-meth-oxy-phen-yl)benzensulfonamide.

In the title compound, C(13)H(11)Cl(2)NO(3)S, the dihedral angle between the benzene rings is 74.37 (3)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules 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 = 332.19

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.06

3456 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.31 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

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

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

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

C13H11Cl2NO3S	F(000) = 680
Mr = 332.19	Dx = 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

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

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(Fo2) + (0.045P)2 + 0.6614P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.46 e Å−3
3456 reflections	Δρmin = −0.31 e Å−3
186 parameters

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) .