4-Chloro-N-(3-chloro-benzo-yl)benzene-sulfonamide monohydrate.

In the title compound, C(13)H(9)Cl(2)NO(3)S·H(2)O, the conformation of the C=O bond is syn to the meta-Cl group in the benzoyl ring. The mol-ecules are twisted at the S-N bond with a C-S-N-C torsion angle of 72.9 (2)°. The dihedral angle between the sulfonyl benzene ring and the S-NH-C-O segment is 77.8 (1)° and that between the sulfonyl and benzoyl benzene rings is 80.5 (1)°. In the crystal, mol-ecules are linked into a two-dimensional network parallel to (100) by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For background to 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. (2009 ▶, 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C13H9Cl2NO3S·H2O

M = 348.19

Monoclinic,

a = 46.909 (3) Å

b = 4.9469 (5) Å

c = 12.919 (1) Å

β = 95.938 (9)°

V = 2981.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.59 mm−1

T = 299 K

0.30 × 0.14 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.843, T max = 0.944

7848 measured reflections

2511 independent reflections

2027 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.184

S = 1.01

2511 reflections

199 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.48 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/S1600536810023962/ci5109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023962/ci5109Isup2.hkl

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

C13H9Cl2NO3S·H2O	F(000) = 1424
Mr = 348.19	Dx = 1.551 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3786 reflections
a = 46.909 (3) Å	θ = 27.9–2.6°
b = 4.9469 (5) Å	µ = 0.59 mm−1
c = 12.919 (1) Å	T = 299 K
β = 95.938 (9)°	Long needle, colourless
V = 2981.8 (4) Å3	0.30 × 0.14 × 0.10 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2511 independent reflections
Radiation source: fine-focus sealed tube	2027 reflections with I > 2σ(I)
graphite	Rint = 0.094
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −56→55
Tmin = 0.843, Tmax = 0.944	k = −5→5
7848 measured reflections	l = −15→15

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.1432P)2] where P = (Fo2 + 2Fc2)/3
2511 reflections	(Δ/σ)max = 0.008
199 parameters	Δρmax = 0.49 e Å−3
3 restraints	Δρmin = −0.48 e Å−3

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
Cl1	0.23824 (2)	−0.1411 (2)	0.15914 (10)	0.0751 (4)
Cl2	0.030813 (19)	−0.4014 (2)	0.16022 (8)	0.0636 (4)
S1	0.145674 (14)	0.62369 (12)	−0.02750 (5)	0.0330 (3)
O1	0.13859 (4)	0.8302 (4)	0.04597 (17)	0.0413 (5)
O2	0.15376 (5)	0.6968 (4)	−0.13059 (16)	0.0478 (6)
O3	0.10727 (4)	0.3795 (4)	0.12809 (15)	0.0433 (6)
N1	0.11762 (5)	0.4252 (5)	−0.04251 (18)	0.0348 (6)
H1N	0.1192 (7)	0.357 (6)	−0.1005 (17)	0.042*
C1	0.17257 (6)	0.4165 (5)	0.0259 (2)	0.0332 (6)
C2	0.17479 (6)	0.3855 (6)	0.1325 (2)	0.0398 (7)
H2	0.1630	0.4779	0.1740	0.048*
C3	0.19519 (7)	0.2122 (7)	0.1723 (2)	0.0456 (7)
H3	0.1976	0.1796	0.2436	0.055*
C4	0.21297 (6)	0.0798 (6)	0.1065 (3)	0.0453 (8)
C5	0.21165 (7)	0.1130 (7)	0.0002 (3)	0.0544 (9)
H5	0.2240	0.0242	−0.0404	0.065*
C6	0.19104 (7)	0.2844 (7)	−0.0406 (2)	0.0476 (8)
H6	0.1888	0.3170	−0.1119	0.057*
C7	0.10191 (6)	0.3242 (5)	0.0382 (2)	0.0340 (6)
C8	0.07754 (6)	0.1437 (5)	0.0091 (2)	0.0363 (7)
C9	0.06672 (5)	−0.0221 (6)	0.0866 (2)	0.0375 (6)
H9	0.0754	−0.0138	0.1546	0.045*
C10	0.04422 (6)	−0.1911 (6)	0.0642 (3)	0.0428 (7)
C11	0.03190 (7)	−0.1960 (8)	−0.0333 (3)	0.0600 (10)
H11	0.0163	−0.3092	−0.0514	0.072*
C12	0.04251 (8)	−0.0290 (9)	−0.1094 (3)	0.0681 (11)
H12	0.0335	−0.0357	−0.1770	0.082*
C13	0.06525 (7)	0.1418 (7)	−0.0887 (3)	0.0516 (9)
H13	0.0718	0.2507	−0.1399	0.062*
O4	0.12309 (7)	0.8386 (5)	0.26833 (19)	0.0640 (7)
H41	0.1273 (10)	0.997 (5)	0.287 (4)	0.096*
H42	0.1245 (11)	0.760 (10)	0.211 (2)	0.096*

	U11	U22	U33	U12	U13	U23
Cl1	0.0623 (6)	0.0664 (7)	0.0913 (9)	0.0265 (4)	−0.0185 (6)	−0.0069 (5)
Cl2	0.0642 (6)	0.0712 (6)	0.0563 (6)	−0.0273 (4)	0.0111 (5)	0.0027 (4)
S1	0.0396 (4)	0.0302 (4)	0.0291 (4)	−0.0026 (2)	0.0029 (3)	0.0016 (2)
O1	0.0499 (11)	0.0297 (10)	0.0434 (11)	−0.0007 (8)	0.0003 (9)	−0.0043 (9)
O2	0.0608 (13)	0.0483 (12)	0.0340 (11)	−0.0061 (10)	0.0041 (10)	0.0097 (10)
O3	0.0485 (11)	0.0524 (13)	0.0282 (11)	−0.0123 (9)	0.0004 (9)	−0.0059 (8)
N1	0.0377 (12)	0.0387 (12)	0.0269 (12)	−0.0045 (10)	−0.0023 (10)	−0.0021 (10)
C1	0.0328 (13)	0.0335 (13)	0.0335 (15)	−0.0047 (11)	0.0042 (11)	−0.0027 (11)
C2	0.0350 (14)	0.0480 (16)	0.0357 (16)	0.0033 (12)	0.0011 (12)	−0.0058 (12)
C3	0.0426 (15)	0.0536 (17)	0.0388 (15)	0.0045 (14)	−0.0035 (13)	−0.0015 (15)
C4	0.0371 (15)	0.0411 (15)	0.055 (2)	0.0041 (12)	−0.0075 (14)	−0.0033 (14)
C5	0.0468 (17)	0.060 (2)	0.057 (2)	0.0109 (15)	0.0100 (16)	−0.0134 (16)
C6	0.0504 (17)	0.0571 (18)	0.0363 (15)	0.0051 (15)	0.0089 (13)	−0.0062 (15)
C7	0.0363 (13)	0.0347 (13)	0.0301 (14)	0.0027 (11)	−0.0017 (11)	−0.0032 (11)
C8	0.0324 (13)	0.0362 (14)	0.0388 (15)	0.0003 (11)	−0.0035 (12)	−0.0020 (11)
C9	0.0337 (14)	0.0455 (16)	0.0326 (14)	−0.0021 (12)	−0.0003 (12)	−0.0046 (12)
C10	0.0372 (15)	0.0464 (16)	0.0450 (17)	−0.0074 (12)	0.0051 (13)	−0.0039 (14)
C11	0.0472 (18)	0.075 (2)	0.054 (2)	−0.0219 (17)	−0.0127 (16)	−0.0065 (19)
C12	0.061 (2)	0.090 (3)	0.047 (2)	−0.023 (2)	−0.0225 (18)	0.005 (2)
C13	0.0528 (18)	0.062 (2)	0.0375 (17)	−0.0116 (15)	−0.0075 (15)	0.0068 (14)
O4	0.111 (2)	0.0504 (14)	0.0298 (12)	0.0019 (14)	0.0024 (13)	0.0003 (11)

Cl1—C4	1.701 (3)	C5—C6	1.351 (4)
Cl2—C10	1.782 (3)	C5—H5	0.93
S1—O1	1.456 (2)	C6—H6	0.93
S1—O2	1.467 (2)	C7—C8	1.468 (4)
S1—N1	1.637 (2)	C8—C13	1.333 (4)
S1—C1	1.714 (3)	C8—C9	1.427 (4)
O3—C7	1.195 (3)	C9—C10	1.354 (4)
N1—C7	1.428 (4)	C9—H9	0.93
N1—H1N	0.833 (18)	C10—C11	1.331 (5)
C1—C2	1.379 (4)	C11—C12	1.413 (6)
C1—C6	1.438 (4)	C11—H11	0.93
C2—C3	1.347 (4)	C12—C13	1.365 (5)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.412 (5)	C13—H13	0.93
C3—H3	0.93	O4—H41	0.83 (2)
C4—C5	1.379 (5)	O4—H42	0.85 (2)
O1—S1—O2	121.10 (13)	C5—C6—H6	119.9
O1—S1—N1	105.25 (13)	C1—C6—H6	119.9
O2—S1—N1	108.69 (12)	O3—C7—N1	123.9 (2)
O1—S1—C1	111.44 (13)	O3—C7—C8	117.9 (3)
O2—S1—C1	105.30 (14)	N1—C7—C8	118.2 (2)
N1—S1—C1	103.79 (12)	C13—C8—C9	120.7 (3)
C7—N1—S1	126.36 (17)	C13—C8—C7	119.7 (3)
C7—N1—H1N	128 (2)	C9—C8—C7	119.6 (2)
S1—N1—H1N	102 (2)	C10—C9—C8	122.1 (3)
C2—C1—C6	123.9 (3)	C10—C9—H9	119.0
C2—C1—S1	116.4 (2)	C8—C9—H9	119.0
C6—C1—S1	119.7 (2)	C11—C10—C9	117.8 (3)
C3—C2—C1	115.5 (3)	C11—C10—Cl2	119.9 (2)
C3—C2—H2	122.3	C9—C10—Cl2	122.4 (2)
C1—C2—H2	122.3	C10—C11—C12	119.9 (3)
C2—C3—C4	120.4 (3)	C10—C11—H11	120.1
C2—C3—H3	119.8	C12—C11—H11	120.1
C4—C3—H3	119.8	C13—C12—C11	123.3 (3)
C5—C4—C3	125.2 (3)	C13—C12—H12	118.3
C5—C4—Cl1	115.6 (3)	C11—C12—H12	118.3
C3—C4—Cl1	119.2 (3)	C8—C13—C12	116.3 (3)
C6—C5—C4	114.8 (3)	C8—C13—H13	121.9
C6—C5—H5	122.6	C12—C13—H13	121.9
C4—C5—H5	122.6	H41—O4—H42	130 (5)
C5—C6—C1	120.2 (3)
O1—S1—N1—C7	−44.3 (2)	S1—C1—C6—C5	−177.6 (3)
O2—S1—N1—C7	−175.4 (2)	S1—N1—C7—O3	1.7 (4)
C1—S1—N1—C7	72.9 (2)	S1—N1—C7—C8	−178.91 (19)
O1—S1—C1—C2	27.9 (3)	O3—C7—C8—C13	159.3 (3)
O2—S1—C1—C2	161.0 (2)	N1—C7—C8—C13	−20.1 (4)
N1—S1—C1—C2	−84.9 (2)	O3—C7—C8—C9	−18.9 (4)
O1—S1—C1—C6	−152.8 (2)	N1—C7—C8—C9	161.7 (2)
O2—S1—C1—C6	−19.7 (3)	C13—C8—C9—C10	1.5 (5)
N1—S1—C1—C6	94.4 (2)	C7—C8—C9—C10	179.7 (3)
C6—C1—C2—C3	−2.2 (4)	C8—C9—C10—C11	−1.0 (5)
S1—C1—C2—C3	177.0 (2)	C8—C9—C10—Cl2	179.3 (2)
C1—C2—C3—C4	1.1 (4)	C9—C10—C11—C12	0.3 (6)
C2—C3—C4—C5	0.5 (5)	Cl2—C10—C11—C12	179.9 (3)
C2—C3—C4—Cl1	−179.2 (2)	C10—C11—C12—C13	0.1 (7)
C3—C4—C5—C6	−1.1 (5)	C9—C8—C13—C12	−1.1 (5)
Cl1—C4—C5—C6	178.6 (2)	C7—C8—C13—C12	−179.3 (3)
C4—C5—C6—C1	0.1 (5)	C11—C12—C13—C8	0.4 (6)
C2—C1—C6—C5	1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.83 (2)	1.98 (2)	2.805 (4)	175 (3)
O4—H41···O2ii	0.83 (2)	2.17 (3)	2.944 (3)	154 (4)
O4—H42···O1	0.85 (2)	2.32 (4)	3.035 (4)	142 (5)
O4—H42···O3	0.85 (2)	2.27 (4)	2.952 (3)	137 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.83 (2)	1.98 (2)	2.805 (4)	175 (3)
O4—H41⋯O2ii	0.83 (2)	2.17 (3)	2.944 (3)	154 (4)
O4—H42⋯O1	0.85 (2)	2.32 (4)	3.035 (4)	142 (5)
O4—H42⋯O3	0.85 (2)	2.27 (4)	2.952 (3)	137 (5)

Symmetry codes: (i) ; (ii) .