2-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 N-H bond is anti to the C=O bond and the dihedral angle between the two aromatic rings is 76.9 (1)°. In the crystal structure, mol-ecules are linked by N-H⋯O(S) hydrogen bonds to form inversion dimers.

Related literature

For background literature and similar structures, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C13H9Cl2NO3S

M = 330.17

Monoclinic,

a = 6.5943 (6) Å

b = 10.9167 (9) Å

c = 20.167 (2) Å

β = 95.83 (1)°

V = 1444.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.60 mm−1

T = 299 K

0.36 × 0.20 × 0.06 mm

Data collection

Oxford Xcalibur with a Sapphire CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.813, T max = 0.965

5854 measured reflections

2942 independent reflections

1919 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.098

S = 1.01

2942 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.31 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/S1600536810012808/bt5238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012808/bt5238Isup2.hkl

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

C13H9Cl2NO3S	F(000) = 672
Mr = 330.17	Dx = 1.518 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1539 reflections
a = 6.5943 (6) Å	θ = 2.8–27.8°
b = 10.9167 (9) Å	µ = 0.60 mm−1
c = 20.167 (2) Å	T = 299 K
β = 95.83 (1)°	Prism, colourless
V = 1444.3 (2) Å3	0.36 × 0.20 × 0.06 mm
Z = 4

Oxford Xcalibur with a Sapphire CCD detector diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	1919 reflections with I > 2σ(I)
graphite	Rint = 0.025
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.813, Tmax = 0.965	k = −10→13
5854 measured reflections	l = −10→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.4268P] where P = (Fo2 + 2Fc2)/3
2942 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.31 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	0.2149 (4)	0.2794 (2)	−0.04754 (11)	0.0395 (6)
C2	0.3515 (4)	0.2090 (3)	−0.07907 (13)	0.0489 (7)
C3	0.5018 (5)	0.2657 (3)	−0.11112 (15)	0.0676 (9)
H3	0.5918	0.2194	−0.1334	0.081*
C4	0.5167 (5)	0.3920 (4)	−0.10965 (16)	0.0733 (10)
H4	0.6193	0.4300	−0.1305	0.088*
C5	0.3847 (5)	0.4618 (3)	−0.07844 (15)	0.0654 (9)
H5	0.3963	0.5467	−0.0781	0.078*
C6	0.2350 (4)	0.4058 (2)	−0.04755 (13)	0.0520 (7)
H6	0.1447	0.4534	−0.0261	0.062*
C7	0.2465 (4)	0.2022 (2)	0.11091 (12)	0.0419 (6)
C8	0.3158 (4)	0.1217 (2)	0.16858 (11)	0.0397 (6)
C9	0.5063 (4)	0.1350 (2)	0.20376 (13)	0.0508 (7)
C10	0.5629 (5)	0.0641 (3)	0.25910 (15)	0.0685 (9)
H10	0.6914	0.0736	0.2821	0.082*
C11	0.4305 (5)	−0.0199 (3)	0.28004 (16)	0.0708 (9)
H11	0.4685	−0.0668	0.3178	0.085*
C12	0.2422 (5)	−0.0358 (3)	0.24604 (14)	0.0629 (8)
H12	0.1530	−0.0937	0.2604	0.076*
C13	0.1849 (4)	0.0343 (2)	0.19040 (12)	0.0492 (7)
H13	0.0570	0.0229	0.1672	0.059*
N1	0.1344 (3)	0.14241 (17)	0.05872 (10)	0.0417 (5)
H1N	0.122 (4)	0.0648 (9)	0.0568 (12)	0.050*
O1	−0.0977 (3)	0.31318 (15)	0.01764 (9)	0.0565 (5)
O2	−0.0841 (3)	0.12191 (15)	−0.04562 (8)	0.0492 (5)
O3	0.2790 (3)	0.31054 (16)	0.10914 (9)	0.0573 (5)
Cl1	0.34230 (13)	0.05007 (7)	−0.07821 (5)	0.0774 (3)
Cl2	0.68560 (13)	0.23576 (8)	0.17804 (5)	0.0878 (3)
S1	0.01817 (10)	0.21602 (5)	−0.00569 (3)	0.04066 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0459 (14)	0.0355 (14)	0.0351 (13)	0.0001 (11)	−0.0054 (11)	−0.0001 (11)
C2	0.0469 (15)	0.0522 (17)	0.0458 (14)	0.0054 (13)	−0.0033 (13)	−0.0018 (13)
C3	0.0485 (18)	0.100 (3)	0.0544 (18)	0.0085 (18)	0.0058 (15)	0.0070 (18)
C4	0.061 (2)	0.098 (3)	0.059 (2)	−0.025 (2)	−0.0009 (17)	0.032 (2)
C5	0.074 (2)	0.059 (2)	0.0605 (19)	−0.0170 (17)	−0.0039 (18)	0.0159 (16)
C6	0.0678 (18)	0.0376 (15)	0.0497 (16)	−0.0071 (13)	0.0023 (14)	0.0059 (12)
C7	0.0524 (15)	0.0349 (15)	0.0394 (13)	−0.0018 (12)	0.0102 (12)	−0.0042 (12)
C8	0.0510 (15)	0.0342 (14)	0.0346 (13)	0.0022 (12)	0.0071 (12)	−0.0039 (11)
C9	0.0538 (17)	0.0483 (16)	0.0498 (16)	−0.0002 (13)	0.0034 (14)	−0.0035 (13)
C10	0.061 (2)	0.080 (2)	0.062 (2)	0.0072 (18)	−0.0071 (16)	0.0039 (18)
C11	0.080 (2)	0.079 (2)	0.0535 (18)	0.0169 (19)	0.0040 (18)	0.0201 (17)
C12	0.080 (2)	0.0596 (19)	0.0517 (17)	−0.0006 (16)	0.0184 (17)	0.0157 (14)
C13	0.0564 (17)	0.0485 (16)	0.0431 (15)	−0.0011 (13)	0.0069 (13)	0.0024 (13)
N1	0.0602 (14)	0.0242 (10)	0.0394 (11)	−0.0032 (10)	−0.0020 (10)	−0.0021 (9)
O1	0.0614 (12)	0.0370 (10)	0.0730 (13)	0.0118 (9)	0.0154 (10)	0.0003 (9)
O2	0.0528 (11)	0.0335 (9)	0.0577 (11)	−0.0052 (8)	−0.0111 (9)	−0.0007 (8)
O3	0.0882 (15)	0.0323 (10)	0.0499 (11)	−0.0107 (10)	−0.0011 (10)	−0.0042 (9)
Cl1	0.0773 (6)	0.0542 (5)	0.1022 (7)	0.0199 (4)	0.0158 (5)	−0.0171 (4)
Cl2	0.0611 (5)	0.0780 (6)	0.1224 (8)	−0.0201 (4)	0.0001 (5)	0.0151 (5)
S1	0.0464 (4)	0.0281 (3)	0.0469 (4)	0.0016 (3)	0.0015 (3)	0.0005 (3)

C1—C2	1.387 (3)	C8—C9	1.386 (3)
C1—C6	1.387 (3)	C8—C13	1.388 (3)
C1—S1	1.760 (2)	C9—C10	1.378 (4)
C2—C3	1.383 (4)	C9—Cl2	1.733 (3)
C2—Cl1	1.736 (3)	C10—C11	1.362 (4)
C3—C4	1.383 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.367 (4)
C4—C5	1.358 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.379 (4)
C5—C6	1.364 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.649 (2)
C7—O3	1.203 (3)	N1—H1N	0.852 (10)
C7—N1	1.387 (3)	O1—S1	1.4153 (17)
C7—C8	1.492 (3)	O2—S1	1.4312 (17)
C2—C1—C6	119.0 (2)	C10—C9—C8	120.8 (3)
C2—C1—S1	123.2 (2)	C10—C9—Cl2	117.5 (2)
C6—C1—S1	117.8 (2)	C8—C9—Cl2	121.6 (2)
C3—C2—C1	119.7 (3)	C11—C10—C9	120.0 (3)
C3—C2—Cl1	118.7 (2)	C11—C10—H10	120.0
C1—C2—Cl1	121.6 (2)	C9—C10—H10	120.0
C4—C3—C2	119.3 (3)	C10—C11—C12	120.5 (3)
C4—C3—H3	120.3	C10—C11—H11	119.7
C2—C3—H3	120.3	C12—C11—H11	119.7
C5—C4—C3	121.5 (3)	C11—C12—C13	119.8 (3)
C5—C4—H4	119.3	C11—C12—H12	120.1
C3—C4—H4	119.3	C13—C12—H12	120.1
C4—C5—C6	119.2 (3)	C12—C13—C8	120.8 (3)
C4—C5—H5	120.4	C12—C13—H13	119.6
C6—C5—H5	120.4	C8—C13—H13	119.6
C5—C6—C1	121.3 (3)	C7—N1—S1	122.53 (17)
C5—C6—H6	119.3	C7—N1—H1N	123.0 (17)
C1—C6—H6	119.3	S1—N1—H1N	114.4 (17)
O3—C7—N1	121.6 (2)	O1—S1—O2	119.05 (11)
O3—C7—C8	124.1 (2)	O1—S1—N1	109.06 (11)
N1—C7—C8	114.3 (2)	O2—S1—N1	104.36 (10)
C9—C8—C13	118.0 (2)	O1—S1—C1	108.31 (11)
C9—C8—C7	121.8 (2)	O2—S1—C1	109.92 (11)
C13—C8—C7	120.1 (2)	N1—S1—C1	105.26 (11)
C6—C1—C2—C3	−1.5 (4)	C8—C9—C10—C11	−0.3 (4)
S1—C1—C2—C3	179.8 (2)	Cl2—C9—C10—C11	−177.6 (2)
C6—C1—C2—Cl1	177.34 (19)	C9—C10—C11—C12	0.9 (5)
S1—C1—C2—Cl1	−1.4 (3)	C10—C11—C12—C13	−0.5 (5)
C1—C2—C3—C4	1.7 (4)	C11—C12—C13—C8	−0.4 (4)
Cl1—C2—C3—C4	−177.1 (2)	C9—C8—C13—C12	0.9 (4)
C2—C3—C4—C5	−1.2 (5)	C7—C8—C13—C12	−176.1 (2)
C3—C4—C5—C6	0.4 (5)	O3—C7—N1—S1	−6.3 (3)
C4—C5—C6—C1	−0.1 (4)	C8—C7—N1—S1	172.07 (17)
C2—C1—C6—C5	0.7 (4)	C7—N1—S1—O1	−49.6 (2)
S1—C1—C6—C5	179.5 (2)	C7—N1—S1—O2	−177.81 (19)
O3—C7—C8—C9	−40.1 (4)	C7—N1—S1—C1	66.4 (2)
N1—C7—C8—C9	141.5 (2)	C2—C1—S1—O1	−177.1 (2)
O3—C7—C8—C13	136.8 (3)	C6—C1—S1—O1	4.1 (2)
N1—C7—C8—C13	−41.5 (3)	C2—C1—S1—O2	−45.5 (2)
C13—C8—C9—C10	−0.6 (4)	C6—C1—S1—O2	135.70 (19)
C7—C8—C9—C10	176.4 (2)	C2—C1—S1—N1	66.3 (2)
C13—C8—C9—Cl2	176.57 (19)	C6—C1—S1—N1	−112.4 (2)
C7—C8—C9—Cl2	−6.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (1)	2.06 (1)	2.913 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (1)	2.06 (1)	2.913 (2)	176 (2)

Symmetry code: (i) .