4-Chloro-N-(4-chloro-benzo-yl)benzene-sulfonamide.

In the title compound, C(13)H(9)Cl(2)NO(3)S, the conformation of the N-H bond in the C-SO(2)-NH-C(O) segment is anti to the C=O bond. The mol-ecule is twisted at the S atom with a torsion angle of 67.5 (3)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 79.0 (1)° and that between the sulfonyl and benzoyl benzene rings is 85.6 (1)°. In the crystal, mol-ecules are linked by N-H⋯O(S) hydrogen bonds with graph-set descriptor C(4) along the [010] direction.

Related literature

For background literature and related structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2009 ▶, 2010 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9Cl2NO3S

M = 330.17

Orthorhombic,

a = 13.6405 (9) Å

b = 9.6495 (8) Å

c = 21.116 (2) Å

V = 2779.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.62 mm−1

T = 299 K

0.34 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis n class="Disease">RED; Oxford Diffraction, 2009 ▶) T min = 0.816, T max = 0.886

10651 measured reflections

2550 independent reflections

1946 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.102

S = 1.07

2550 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001559X/bx2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001559X/bx2279Isup2.hkl

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

C13H9Cl2NO3S	F(000) = 1344
Mr = 330.17	Dx = 1.578 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6170 reflections
a = 13.6405 (9) Å	θ = 2.6–27.9°
b = 9.6495 (8) Å	µ = 0.62 mm−1
c = 21.116 (2) Å	T = 299 K
V = 2779.4 (4) Å3	Prism, colourless
Z = 8	0.34 × 0.30 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2550 independent reflections
Radiation source: fine-focus sealed tube	1946 reflections with I > 2σ(I)
graphite	Rint = 0.026
Rotation method data acquisition using ω and phi scans	θmax = 25.3°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→16
Tmin = 0.816, Tmax = 0.886	k = −11→8
10651 measured reflections	l = −25→25

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0343P)2 + 2.7251P] where P = (Fo2 + 2Fc2)/3
2550 reflections	(Δ/σ)max = 0.004
184 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.43 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.99158 (19)	0.2323 (3)	0.55735 (12)	0.0379 (6)
C2	1.0488 (2)	0.3501 (3)	0.55627 (16)	0.0589 (9)
H2	1.0305	0.4251	0.5313	0.071*
C3	1.1332 (2)	0.3571 (3)	0.59208 (17)	0.0623 (9)
H3	1.1726	0.4358	0.5911	0.075*
C4	1.15804 (19)	0.2462 (3)	0.62912 (14)	0.0453 (7)
C5	1.1027 (2)	0.1281 (3)	0.63045 (15)	0.0532 (8)
H5	1.1214	0.0536	0.6556	0.064*
C6	1.0187 (2)	0.1205 (3)	0.59412 (14)	0.0478 (7)
H6	0.9806	0.0406	0.5944	0.057*
C7	0.77151 (18)	0.3738 (2)	0.58811 (13)	0.0358 (6)
C8	0.68782 (18)	0.3726 (2)	0.63338 (13)	0.0361 (6)
C9	0.6890 (2)	0.4687 (3)	0.68266 (14)	0.0450 (7)
H9	0.7406	0.5313	0.6858	0.054*
C10	0.6147 (2)	0.4719 (3)	0.72667 (14)	0.0504 (7)
H10	0.6162	0.5358	0.7596	0.061*
C11	0.5378 (2)	0.3794 (3)	0.72143 (14)	0.0464 (7)
C12	0.5335 (2)	0.2852 (3)	0.67218 (15)	0.0482 (7)
H12	0.4805	0.2252	0.6684	0.058*
C13	0.60898 (18)	0.2814 (3)	0.62879 (14)	0.0431 (7)
H13	0.6072	0.2171	0.5960	0.052*
N1	0.79169 (16)	0.2491 (2)	0.55934 (11)	0.0395 (5)
H1N	0.7586 (18)	0.1768 (19)	0.5681 (13)	0.047*
O1	0.87074 (15)	0.0780 (2)	0.49305 (11)	0.0610 (6)
O2	0.88803 (15)	0.3255 (2)	0.46352 (9)	0.0595 (6)
O3	0.82124 (13)	0.47670 (18)	0.57873 (10)	0.0485 (5)
Cl1	1.26227 (6)	0.25736 (10)	0.67639 (4)	0.0679 (3)
Cl2	0.44389 (6)	0.38508 (11)	0.77714 (4)	0.0710 (3)
S1	0.88532 (5)	0.21948 (7)	0.51034 (3)	0.0437 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0323 (13)	0.0400 (15)	0.0415 (15)	0.0010 (11)	0.0068 (12)	−0.0043 (13)
C2	0.0546 (19)	0.0498 (18)	0.072 (2)	−0.0097 (15)	−0.0159 (17)	0.0228 (16)
C3	0.0489 (18)	0.0569 (19)	0.081 (2)	−0.0157 (15)	−0.0158 (17)	0.0160 (18)
C4	0.0324 (13)	0.0561 (17)	0.0474 (16)	0.0058 (13)	0.0016 (13)	−0.0011 (14)
C5	0.0475 (17)	0.0484 (17)	0.064 (2)	0.0084 (14)	0.0035 (15)	0.0128 (15)
C6	0.0418 (16)	0.0391 (15)	0.0624 (19)	−0.0035 (13)	0.0076 (14)	0.0040 (14)
C7	0.0299 (13)	0.0294 (13)	0.0482 (16)	0.0023 (11)	−0.0065 (11)	−0.0014 (12)
C8	0.0308 (13)	0.0295 (13)	0.0480 (16)	0.0057 (10)	−0.0052 (12)	−0.0011 (12)
C9	0.0364 (15)	0.0432 (15)	0.0555 (18)	−0.0008 (13)	−0.0073 (13)	−0.0093 (14)
C10	0.0463 (17)	0.0595 (19)	0.0454 (17)	0.0041 (15)	−0.0051 (14)	−0.0129 (15)
C11	0.0368 (15)	0.0548 (18)	0.0475 (17)	0.0106 (13)	0.0015 (13)	0.0041 (15)
C12	0.0360 (15)	0.0419 (16)	0.067 (2)	−0.0017 (12)	0.0044 (14)	−0.0003 (15)
C13	0.0357 (14)	0.0327 (14)	0.0608 (18)	0.0006 (12)	0.0007 (14)	−0.0091 (13)
N1	0.0327 (12)	0.0294 (11)	0.0564 (15)	−0.0013 (9)	0.0065 (11)	−0.0053 (11)
O1	0.0491 (12)	0.0582 (13)	0.0758 (15)	0.0005 (10)	0.0050 (11)	−0.0327 (12)
O2	0.0550 (13)	0.0814 (15)	0.0421 (11)	−0.0084 (12)	−0.0030 (10)	0.0079 (11)
O3	0.0399 (10)	0.0333 (10)	0.0721 (14)	−0.0061 (9)	0.0041 (10)	−0.0047 (10)
Cl1	0.0442 (4)	0.0885 (6)	0.0709 (6)	0.0080 (4)	−0.0124 (4)	0.0004 (5)
Cl2	0.0533 (5)	0.1024 (7)	0.0574 (5)	0.0095 (5)	0.0137 (4)	0.0039 (5)
S1	0.0380 (4)	0.0479 (4)	0.0452 (4)	−0.0015 (3)	0.0034 (3)	−0.0091 (3)

C1—C2	1.379 (4)	C8—C13	1.393 (3)
C1—C6	1.380 (4)	C8—C9	1.394 (4)
C1—S1	1.761 (3)	C9—C10	1.376 (4)
C2—C3	1.379 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.381 (4)
C3—C4	1.368 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.383 (4)
C4—C5	1.367 (4)	C11—Cl2	1.740 (3)
C4—Cl1	1.740 (3)	C12—C13	1.379 (4)
C5—C6	1.380 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.668 (2)
C7—O3	1.219 (3)	N1—H1N	0.851 (10)
C7—N1	1.376 (3)	O1—S1	1.427 (2)
C7—C8	1.489 (4)	O2—S1	1.423 (2)
C2—C1—C6	120.1 (3)	C10—C9—C8	120.7 (3)
C2—C1—S1	121.0 (2)	C10—C9—H9	119.7
C6—C1—S1	118.9 (2)	C8—C9—H9	119.6
C3—C2—C1	120.3 (3)	C9—C10—C11	119.4 (3)
C3—C2—H2	119.9	C9—C10—H10	120.3
C1—C2—H2	119.9	C11—C10—H10	120.3
C4—C3—C2	118.8 (3)	C12—C11—C10	121.1 (3)
C4—C3—H3	120.6	C12—C11—Cl2	119.9 (2)
C2—C3—H3	120.6	C10—C11—Cl2	119.0 (2)
C3—C4—C5	121.8 (3)	C13—C12—C11	119.1 (3)
C3—C4—Cl1	118.8 (2)	C13—C12—H12	120.5
C5—C4—Cl1	119.4 (2)	C11—C12—H12	120.5
C4—C5—C6	119.4 (3)	C12—C13—C8	120.9 (3)
C4—C5—H5	120.3	C12—C13—H13	119.6
C6—C5—H5	120.3	C8—C13—H13	119.6
C5—C6—C1	119.6 (3)	C7—N1—S1	125.21 (18)
C5—C6—H6	120.2	C7—N1—H1N	121 (2)
C1—C6—H6	120.2	S1—N1—H1N	113.7 (19)
O3—C7—N1	122.0 (2)	O2—S1—O1	120.90 (14)
O3—C7—C8	122.5 (2)	O2—S1—N1	109.13 (12)
N1—C7—C8	115.5 (2)	O1—S1—N1	102.45 (12)
C13—C8—C9	118.8 (3)	O2—S1—C1	108.63 (12)
C13—C8—C7	123.5 (2)	O1—S1—C1	109.05 (13)
C9—C8—C7	117.7 (2)	N1—S1—C1	105.57 (12)
C6—C1—C2—C3	−0.3 (5)	C9—C10—C11—Cl2	−179.7 (2)
S1—C1—C2—C3	−178.3 (3)	C10—C11—C12—C13	1.9 (4)
C1—C2—C3—C4	−0.9 (5)	Cl2—C11—C12—C13	−179.5 (2)
C2—C3—C4—C5	1.4 (5)	C11—C12—C13—C8	−1.3 (4)
C2—C3—C4—Cl1	−177.8 (3)	C9—C8—C13—C12	−0.3 (4)
C3—C4—C5—C6	−0.8 (5)	C7—C8—C13—C12	180.0 (2)
Cl1—C4—C5—C6	178.5 (2)	O3—C7—N1—S1	1.5 (4)
C4—C5—C6—C1	−0.4 (4)	C8—C7—N1—S1	−175.99 (18)
C2—C1—C6—C5	0.9 (4)	C7—N1—S1—O2	−49.1 (3)
S1—C1—C6—C5	179.0 (2)	C7—N1—S1—O1	−178.3 (2)
O3—C7—C8—C13	154.8 (3)	C7—N1—S1—C1	67.5 (2)
N1—C7—C8—C13	−27.7 (4)	C2—C1—S1—O2	15.4 (3)
O3—C7—C8—C9	−24.9 (4)	C6—C1—S1—O2	−162.6 (2)
N1—C7—C8—C9	152.5 (2)	C2—C1—S1—O1	149.0 (3)
C13—C8—C9—C10	1.2 (4)	C6—C1—S1—O1	−29.0 (3)
C7—C8—C9—C10	−179.1 (2)	C2—C1—S1—N1	−101.5 (3)
C8—C9—C10—C11	−0.5 (4)	C6—C1—S1—N1	80.5 (2)
C9—C10—C11—C12	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (1)	2.23 (1)	3.074 (3)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (1)	2.23 (1)	3.074 (3)	172 (3)

Symmetry code: (i) .