4-Chloro-N-(2-chloro-benzo-yl)benzene-sulfonamide.

In the structure of 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 65.7 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 88.5 (1)°, and that between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for related structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C13H9Cl2NO3S

M = 330.17

Triclinic,

a = 6.3882 (9) Å

b = 10.311 (1) Å

c = 11.171 (1) Å

α = 79.01 (1)°

β = 74.47 (1)°

γ = 84.76 (1)°

V = 695.32 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.62 mm−1

T = 299 K

0.24 × 0.20 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.865, T max = 0.918

4417 measured reflections

2825 independent reflections

2378 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.06

2825 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data 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/S1600536810019057/xu2765sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019057/xu2765Isup2.hkl

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

C13H9Cl2NO3S	Z = 2
Mr = 330.17	F(000) = 336
Triclinic, P1	Dx = 1.577 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3882 (9) Å	Cell parameters from 2339 reflections
b = 10.311 (1) Å	θ = 2.5–27.8°
c = 11.171 (1) Å	µ = 0.62 mm−1
α = 79.01 (1)°	T = 299 K
β = 74.47 (1)°	Prism, colourless
γ = 84.76 (1)°	0.24 × 0.20 × 0.14 mm
V = 695.32 (13) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2825 independent reflections
Radiation source: fine-focus sealed tube	2378 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.865, Tmax = 0.918	k = −12→11
4417 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1863P] where P = (Fo2 + 2Fc2)/3
2825 reflections	(Δ/σ)max = 0.022
184 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.52 e Å−3

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	0.3004 (3)	0.27841 (17)	0.07988 (17)	0.0364 (4)
C2	0.1714 (3)	0.39202 (19)	0.0968 (2)	0.0464 (5)
H2	0.0437	0.4059	0.0703	0.056*
C3	0.2338 (4)	0.4844 (2)	0.1532 (2)	0.0561 (6)
H3	0.1510	0.5624	0.1634	0.067*
C4	0.4198 (4)	0.4596 (2)	0.1942 (2)	0.0520 (5)
C5	0.5482 (4)	0.3465 (2)	0.1791 (2)	0.0543 (5)
H5	0.6730	0.3317	0.2085	0.065*
C6	0.4895 (3)	0.2553 (2)	0.1198 (2)	0.0478 (5)
H6	0.5760	0.1791	0.1068	0.057*
C7	0.0089 (3)	0.02215 (18)	0.22952 (18)	0.0384 (4)
C8	0.0163 (3)	−0.09961 (18)	0.32606 (17)	0.0396 (4)
C9	0.1632 (3)	−0.1155 (2)	0.39978 (18)	0.0451 (4)
C10	0.1579 (5)	−0.2246 (3)	0.4941 (2)	0.0641 (7)
H10	0.2565	−0.2347	0.5436	0.077*
C11	0.0073 (6)	−0.3171 (3)	0.5141 (2)	0.0757 (8)
H11	0.0043	−0.3908	0.5771	0.091*
C12	−0.1402 (5)	−0.3025 (3)	0.4422 (3)	0.0730 (7)
H12	−0.2424	−0.3663	0.4568	0.088*
C13	−0.1370 (4)	−0.1940 (2)	0.3487 (2)	0.0554 (5)
H13	−0.2378	−0.1840	0.3007	0.066*
Cl1	0.34983 (10)	0.00381 (7)	0.37663 (6)	0.0664 (2)
Cl2	0.49683 (16)	0.57327 (7)	0.26873 (8)	0.0938 (3)
N1	0.1748 (3)	0.02815 (15)	0.12059 (15)	0.0398 (4)
H1N	0.276 (3)	−0.0255 (19)	0.114 (2)	0.048*
O1	0.0294 (3)	0.20637 (15)	−0.02823 (14)	0.0550 (4)
O2	0.4074 (3)	0.11865 (14)	−0.08329 (13)	0.0537 (4)
O3	−0.1307 (2)	0.10807 (16)	0.24443 (16)	0.0602 (4)
S1	0.22277 (8)	0.15972 (4)	0.00846 (4)	0.04047 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0364 (9)	0.0325 (8)	0.0360 (9)	−0.0001 (7)	−0.0058 (7)	−0.0008 (7)
C2	0.0448 (11)	0.0390 (10)	0.0503 (11)	0.0069 (8)	−0.0122 (9)	0.0006 (8)
C3	0.0695 (14)	0.0344 (10)	0.0568 (13)	0.0062 (9)	−0.0075 (11)	−0.0055 (9)
C4	0.0665 (14)	0.0424 (11)	0.0432 (11)	−0.0177 (9)	−0.0044 (10)	−0.0045 (8)
C5	0.0468 (11)	0.0561 (13)	0.0610 (13)	−0.0108 (9)	−0.0159 (10)	−0.0051 (10)
C6	0.0382 (10)	0.0431 (10)	0.0617 (13)	0.0040 (8)	−0.0140 (9)	−0.0091 (9)
C7	0.0365 (9)	0.0413 (9)	0.0406 (9)	−0.0023 (7)	−0.0146 (7)	−0.0076 (7)
C8	0.0430 (10)	0.0399 (9)	0.0342 (9)	0.0004 (7)	−0.0076 (7)	−0.0064 (7)
C9	0.0464 (10)	0.0529 (11)	0.0364 (10)	0.0068 (8)	−0.0111 (8)	−0.0120 (8)
C10	0.0786 (16)	0.0707 (15)	0.0399 (11)	0.0199 (13)	−0.0188 (11)	−0.0076 (10)
C11	0.112 (2)	0.0556 (14)	0.0457 (13)	0.0047 (14)	−0.0087 (14)	0.0059 (11)
C12	0.095 (2)	0.0539 (14)	0.0628 (16)	−0.0230 (13)	−0.0095 (14)	0.0015 (12)
C13	0.0615 (13)	0.0548 (12)	0.0500 (12)	−0.0148 (10)	−0.0127 (10)	−0.0059 (10)
Cl1	0.0571 (4)	0.0895 (4)	0.0633 (4)	−0.0126 (3)	−0.0273 (3)	−0.0178 (3)
Cl2	0.1363 (7)	0.0706 (5)	0.0834 (5)	−0.0386 (4)	−0.0236 (5)	−0.0259 (4)
N1	0.0441 (9)	0.0340 (8)	0.0394 (8)	0.0013 (6)	−0.0095 (7)	−0.0049 (6)
O1	0.0577 (9)	0.0586 (9)	0.0546 (9)	0.0005 (7)	−0.0303 (7)	−0.0030 (7)
O2	0.0656 (9)	0.0503 (8)	0.0367 (7)	0.0079 (7)	−0.0037 (6)	−0.0050 (6)
O3	0.0483 (8)	0.0617 (9)	0.0603 (10)	0.0152 (7)	−0.0092 (7)	−0.0008 (7)
S1	0.0464 (3)	0.0387 (3)	0.0356 (3)	0.00192 (18)	−0.01273 (19)	−0.00320 (18)

C1—C6	1.382 (3)	C8—C13	1.385 (3)
C1—C2	1.383 (3)	C8—C9	1.386 (3)
C1—S1	1.7537 (19)	C9—C10	1.382 (3)
C2—C3	1.377 (3)	C9—Cl1	1.727 (2)
C2—H2	0.9300	C10—C11	1.363 (4)
C3—C4	1.370 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.375 (4)
C4—C5	1.374 (3)	C11—H11	0.9300
C4—Cl2	1.733 (2)	C12—C13	1.375 (3)
C5—C6	1.379 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.6510 (16)
C7—O3	1.200 (2)	N1—H1N	0.810 (15)
C7—N1	1.379 (3)	O1—S1	1.4185 (15)
C7—C8	1.497 (3)	O2—S1	1.4311 (15)
C6—C1—C2	121.20 (18)	C10—C9—C8	120.5 (2)
C6—C1—S1	118.92 (14)	C10—C9—Cl1	119.64 (18)
C2—C1—S1	119.87 (15)	C8—C9—Cl1	119.82 (16)
C3—C2—C1	119.35 (19)	C11—C10—C9	119.6 (2)
C3—C2—H2	120.3	C11—C10—H10	120.2
C1—C2—H2	120.3	C9—C10—H10	120.2
C4—C3—C2	119.03 (19)	C10—C11—C12	120.7 (2)
C4—C3—H3	120.5	C10—C11—H11	119.7
C2—C3—H3	120.5	C12—C11—H11	119.7
C3—C4—C5	122.2 (2)	C13—C12—C11	120.2 (2)
C3—C4—Cl2	119.51 (17)	C13—C12—H12	119.9
C5—C4—Cl2	118.31 (18)	C11—C12—H12	119.9
C4—C5—C6	119.0 (2)	C12—C13—C8	120.0 (2)
C4—C5—H5	120.5	C12—C13—H13	120.0
C6—C5—H5	120.5	C8—C13—H13	120.0
C5—C6—C1	119.17 (18)	C7—N1—S1	124.25 (13)
C5—C6—H6	120.4	C7—N1—H1N	121.9 (16)
C1—C6—H6	120.4	S1—N1—H1N	112.1 (16)
O3—C7—N1	122.05 (18)	O1—S1—O2	119.26 (9)
O3—C7—C8	123.12 (18)	O1—S1—N1	110.18 (9)
N1—C7—C8	114.82 (15)	O2—S1—N1	103.74 (8)
C13—C8—C9	119.07 (19)	O1—S1—C1	108.96 (9)
C13—C8—C7	119.35 (17)	O2—S1—C1	109.21 (9)
C9—C8—C7	121.40 (17)	N1—S1—C1	104.43 (8)
C6—C1—C2—C3	0.7 (3)	C8—C9—C10—C11	0.2 (3)
S1—C1—C2—C3	179.87 (16)	Cl1—C9—C10—C11	178.50 (19)
C1—C2—C3—C4	−1.7 (3)	C9—C10—C11—C12	−0.5 (4)
C2—C3—C4—C5	1.0 (3)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—Cl2	−178.50 (16)	C11—C12—C13—C8	0.6 (4)
C3—C4—C5—C6	0.6 (3)	C9—C8—C13—C12	−0.9 (3)
Cl2—C4—C5—C6	−179.85 (17)	C7—C8—C13—C12	−176.2 (2)
C4—C5—C6—C1	−1.6 (3)	O3—C7—N1—S1	9.1 (3)
C2—C1—C6—C5	0.9 (3)	C8—C7—N1—S1	−171.37 (13)
S1—C1—C6—C5	−178.23 (16)	C7—N1—S1—O1	−51.19 (18)
O3—C7—C8—C13	70.4 (3)	C7—N1—S1—O2	−179.94 (15)
N1—C7—C8—C13	−109.1 (2)	C7—N1—S1—C1	65.68 (17)
O3—C7—C8—C9	−104.8 (2)	C6—C1—S1—O1	−178.06 (15)
N1—C7—C8—C9	75.7 (2)	C2—C1—S1—O1	2.78 (18)
C13—C8—C9—C10	0.4 (3)	C6—C1—S1—O2	−46.22 (18)
C7—C8—C9—C10	175.66 (18)	C2—C1—S1—O2	134.61 (15)
C13—C8—C9—Cl1	−177.81 (16)	C6—C1—S1—N1	64.23 (17)
C7—C8—C9—Cl1	−2.6 (3)	C2—C1—S1—N1	−114.93 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.81 (2)	2.13 (2)	2.914 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.81 (2)	2.13 (2)	2.914 (2)	164 (2)

Symmetry code: (i) .