N-(3,5-Dichloro-phen-yl)benzene-sulfonamide.

In the crystal structure of the title compound, C(12)H(9)Cl(2)NO(2)S, the aromatic rings are aligned at 57.0 (1)°. The mol-ecules form chains via inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the structural systematics of 4,4′-disubstituted aryl benzene­sulfonamides, see: Gelbrich et al. (2007 ▶). For mono- and di-substituted-aryl benzene­sulfonamides, see: Gowda et al. (2008a ▶,b ▶); Tkachev et al. (2006 ▶). For the spectroscopic analysis of the title compound, see: Shetty & Gowda (2005 ▶).

Experimental

Crystal data

C12H9Cl2NO2S

M = 302.16

Monoclinic,

a = 8.299 (2) Å

b = 7.215 (1) Å

c = 21.954 (3) Å

β = 99.49 (1)°

V = 1296.6 (4) Å3

Z = 4

Cu Kα radiation

μ = 5.96 mm−1

T = 299 (2) K

0.50 × 0.50 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.129, T max = 0.229

2518 measured reflections

2311 independent reflections

2153 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.156

S = 1.10

2311 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034351/ng2501sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034351/ng2501Isup2.hkl

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

C12H9Cl2NO2S	F(000) = 616
Mr = 302.16	Dx = 1.548 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.299 (2) Å	θ = 5.4–19.4°
b = 7.215 (1) Å	µ = 5.96 mm−1
c = 21.954 (3) Å	T = 299 K
β = 99.49 (1)°	Prism, colourless
V = 1296.6 (4) Å3	0.50 × 0.50 × 0.25 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2153 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 67.0°, θmin = 4.1°
ω/2θ scans	h = −9→1
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.129, Tmax = 0.229	l = −26→26
2518 measured reflections	3 standard reflections every 120 min
2311 independent reflections	intensity decay: 1.0%

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0987P)2 + 0.7373P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2311 reflections	Δρmax = 0.59 e Å−3
167 parameters	Δρmin = −0.38 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0105 (11)

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.

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 > σ(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.

	x	y	z	Uiso*/Ueq
C1	0.3043 (3)	0.1779 (4)	0.79280 (13)	0.0445 (6)
C2	0.4358 (4)	0.1697 (5)	0.84058 (17)	0.0604 (8)
H2	0.4201	0.1476	0.8809	0.072*
C3	0.5911 (4)	0.1953 (6)	0.8269 (2)	0.0783 (12)
H3	0.6811	0.1914	0.8584	0.094*
C4	0.6130 (4)	0.2267 (6)	0.7670 (2)	0.0773 (11)
H4	0.7180	0.2427	0.7582	0.093*
C5	0.4818 (5)	0.2344 (5)	0.7202 (2)	0.0746 (10)
H5	0.4980	0.2547	0.6798	0.090*
C6	0.3257 (4)	0.2121 (4)	0.73293 (15)	0.0562 (7)
H6	0.2360	0.2200	0.7015	0.067*
C7	0.1252 (3)	0.3838 (4)	0.90059 (11)	0.0400 (6)
C8	0.2051 (4)	0.5522 (4)	0.90920 (13)	0.0484 (6)
H8	0.2132	0.6288	0.8758	0.058*
C9	0.2725 (4)	0.6041 (4)	0.96827 (15)	0.0558 (7)
C10	0.2645 (4)	0.4935 (4)	1.01861 (14)	0.0590 (8)
H10	0.3122	0.5293	1.0582	0.071*
C11	0.1830 (4)	0.3278 (4)	1.00819 (13)	0.0534 (7)
C12	0.1118 (3)	0.2699 (4)	0.95062 (12)	0.0480 (6)
H12	0.0561	0.1577	0.9451	0.058*
N1	0.0494 (3)	0.3297 (3)	0.84009 (10)	0.0441 (5)
H1N	0.038 (4)	0.418 (3)	0.8138 (12)	0.053*
O1	−0.0021 (3)	0.1298 (3)	0.74998 (9)	0.0527 (5)
O2	0.1112 (3)	−0.0066 (3)	0.85135 (10)	0.0574 (6)
Cl1	0.37237 (16)	0.81541 (13)	0.97944 (5)	0.0927 (4)
Cl2	0.16462 (15)	0.18752 (15)	1.07089 (4)	0.0834 (4)
S1	0.10584 (7)	0.14095 (9)	0.80800 (3)	0.0412 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0475 (14)	0.0400 (13)	0.0467 (15)	0.0019 (11)	0.0101 (11)	0.0007 (11)
C2	0.0571 (17)	0.0615 (19)	0.0589 (19)	0.0079 (14)	−0.0009 (14)	−0.0049 (15)
C3	0.0517 (18)	0.065 (2)	0.111 (3)	0.0057 (15)	−0.0071 (19)	−0.014 (2)
C4	0.0560 (19)	0.063 (2)	0.117 (4)	0.0031 (16)	0.029 (2)	0.001 (2)
C5	0.079 (2)	0.064 (2)	0.091 (3)	−0.0014 (18)	0.044 (2)	0.0114 (19)
C6	0.0619 (17)	0.0556 (17)	0.0535 (17)	0.0004 (14)	0.0161 (13)	0.0070 (13)
C7	0.0447 (13)	0.0413 (13)	0.0349 (12)	0.0025 (10)	0.0088 (10)	−0.0039 (10)
C8	0.0581 (15)	0.0404 (14)	0.0465 (14)	0.0000 (12)	0.0079 (12)	0.0033 (12)
C9	0.0631 (17)	0.0424 (15)	0.0585 (17)	−0.0015 (13)	0.0001 (13)	−0.0043 (13)
C10	0.078 (2)	0.0531 (17)	0.0426 (15)	0.0025 (15)	0.0004 (14)	−0.0087 (13)
C11	0.0701 (18)	0.0540 (16)	0.0379 (14)	0.0049 (14)	0.0141 (13)	0.0020 (12)
C12	0.0593 (16)	0.0466 (15)	0.0405 (14)	−0.0057 (12)	0.0157 (12)	−0.0028 (11)
N1	0.0547 (13)	0.0423 (12)	0.0350 (12)	0.0020 (10)	0.0064 (9)	−0.0004 (9)
O1	0.0548 (11)	0.0586 (12)	0.0427 (11)	−0.0059 (9)	0.0021 (8)	−0.0107 (9)
O2	0.0838 (15)	0.0415 (11)	0.0499 (11)	−0.0053 (10)	0.0199 (10)	0.0058 (8)
Cl1	0.1209 (9)	0.0518 (5)	0.0915 (8)	−0.0250 (5)	−0.0236 (6)	−0.0022 (4)
Cl2	0.1333 (9)	0.0798 (7)	0.0393 (5)	−0.0122 (6)	0.0204 (5)	0.0085 (4)
S1	0.0495 (4)	0.0384 (4)	0.0359 (4)	−0.0042 (2)	0.0076 (3)	−0.0018 (2)

C1—C6	1.377 (4)	C7—N1	1.427 (3)
C1—C2	1.385 (4)	C8—C9	1.377 (4)
C1—S1	1.754 (3)	C8—H8	0.9300
C2—C3	1.383 (5)	C9—C10	1.374 (5)
C2—H2	0.9300	C9—Cl1	1.734 (3)
C3—C4	1.376 (6)	C10—C11	1.374 (5)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.370 (6)	C11—C12	1.369 (4)
C4—H4	0.9300	C11—Cl2	1.736 (3)
C5—C6	1.379 (5)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.637 (2)
C6—H6	0.9300	N1—H1N	0.856 (10)
C7—C8	1.382 (4)	O1—S1	1.433 (2)
C7—C12	1.391 (4)	O2—S1	1.424 (2)
C6—C1—C2	121.4 (3)	C7—C8—H8	120.7
C6—C1—S1	118.8 (2)	C10—C9—C8	122.3 (3)
C2—C1—S1	119.8 (2)	C10—C9—Cl1	118.9 (2)
C3—C2—C1	118.5 (4)	C8—C9—Cl1	118.9 (2)
C3—C2—H2	120.8	C11—C10—C9	117.3 (3)
C1—C2—H2	120.8	C11—C10—H10	121.3
C4—C3—C2	120.3 (4)	C9—C10—H10	121.3
C4—C3—H3	119.9	C12—C11—C10	123.0 (3)
C2—C3—H3	119.9	C12—C11—Cl2	118.2 (2)
C5—C4—C3	120.6 (3)	C10—C11—Cl2	118.7 (2)
C5—C4—H4	119.7	C11—C12—C7	118.0 (3)
C3—C4—H4	119.7	C11—C12—H12	121.0
C4—C5—C6	120.0 (4)	C7—C12—H12	121.0
C4—C5—H5	120.0	C7—N1—S1	120.98 (18)
C6—C5—H5	120.0	C7—N1—H1N	114 (2)
C1—C6—C5	119.2 (3)	S1—N1—H1N	110 (2)
C1—C6—H6	120.4	O2—S1—O1	119.87 (14)
C5—C6—H6	120.4	O2—S1—N1	108.29 (12)
C8—C7—C12	120.7 (2)	O1—S1—N1	104.34 (12)
C8—C7—N1	119.7 (2)	O2—S1—C1	108.30 (14)
C12—C7—N1	119.5 (2)	O1—S1—C1	107.97 (13)
C9—C8—C7	118.6 (3)	N1—S1—C1	107.45 (13)
C9—C8—H8	120.7
C6—C1—C2—C3	−0.5 (5)	C10—C11—C12—C7	1.0 (5)
S1—C1—C2—C3	178.6 (3)	Cl2—C11—C12—C7	179.2 (2)
C1—C2—C3—C4	−0.5 (5)	C8—C7—C12—C11	−1.4 (4)
C2—C3—C4—C5	0.5 (6)	N1—C7—C12—C11	−178.6 (3)
C3—C4—C5—C6	0.5 (6)	C8—C7—N1—S1	119.8 (2)
C2—C1—C6—C5	1.5 (5)	C12—C7—N1—S1	−62.9 (3)
S1—C1—C6—C5	−177.6 (3)	C7—N1—S1—O2	48.5 (2)
C4—C5—C6—C1	−1.5 (5)	C7—N1—S1—O1	177.3 (2)
C12—C7—C8—C9	0.6 (4)	C7—N1—S1—C1	−68.3 (2)
N1—C7—C8—C9	177.8 (3)	C6—C1—S1—O2	138.8 (2)
C7—C8—C9—C10	0.7 (5)	C2—C1—S1—O2	−40.3 (3)
C7—C8—C9—Cl1	−179.8 (2)	C6—C1—S1—O1	7.6 (3)
C8—C9—C10—C11	−1.2 (5)	C2—C1—S1—O1	−171.5 (2)
Cl1—C9—C10—C11	179.4 (3)	C6—C1—S1—N1	−104.5 (2)
C9—C10—C11—C12	0.3 (5)	C2—C1—S1—N1	76.5 (3)
C9—C10—C11—Cl2	−178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (1)	2.06 (1)	2.915 (3)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.856 (10)	2.059 (11)	2.915 (3)	178 (3)

Symmetry code: (i) .