N,N-Bis(4-chloro-phenyl-sulfon-yl)succinamide dihydrate.

The asymmetric unit of the title compound, C(16)H(14)Cl(2)N(2)O(6)S(2)·2H(2)O, contains one half-mol-ecule of N,N-bis-(4-chloro-phenyl-sulfon-yl)succinamide, with a centre of symmetry at the mid-point of the central C-C bond, and one water mol-ecule. The succinamide mol-ecules are not directly connected via hydrogen bonds, but by hydrogen bonds via the water mol-ecules.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Rodrigues et al. (2011 ▶), of N-chloro­aryl­amides, see: Gowda & Rao (1989 ▶); Jyothi & Gowda (2004 ▶) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶).

Experimental

Crystal data

C16H14Cl2N2O6S2·2H2O

M = 501.34

Monoclinic,

a = 33.349 (2) Å

b = 4.9737 (4) Å

c = 13.171 (1) Å

β = 90.660 (7)°

V = 2184.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 293 K

0.48 × 0.40 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.784, T max = 0.939

3837 measured reflections

2233 independent reflections

1906 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.120

S = 1.06

2233 reflections

139 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812024725/bt5934sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024725/bt5934Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024725/bt5934Isup3.cml

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

C16H14Cl2N2O6S2·2H2O	F(000) = 1032
Mr = 501.34	Dx = 1.524 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1880 reflections
a = 33.349 (2) Å	θ = 2.9–27.9°
b = 4.9737 (4) Å	µ = 0.53 mm−1
c = 13.171 (1) Å	T = 293 K
β = 90.660 (7)°	Plate, colourless
V = 2184.5 (3) Å3	0.48 × 0.40 × 0.12 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2233 independent reflections
Radiation source: fine-focus sealed tube	1906 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −31→41
Tmin = 0.784, Tmax = 0.939	k = −6→2
3837 measured reflections	l = −16→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0516P)2 + 3.9644P] where P = (Fo2 + 2Fc2)/3
2233 reflections	(Δ/σ)max = 0.004
139 parameters	Δρmax = 0.55 e Å−3
7 restraints	Δρmin = −0.49 e Å−3

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

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	0.23218 (3)	0.6607 (2)	0.16525 (9)	0.0914 (4)
S1	0.104840 (19)	−0.08075 (14)	−0.04102 (5)	0.0398 (2)
O1	0.11860 (7)	−0.1623 (5)	−0.13839 (15)	0.0590 (6)
O2	0.09204 (6)	−0.2788 (4)	0.02984 (15)	0.0487 (5)
O3	0.04604 (6)	0.1896 (4)	0.09543 (13)	0.0474 (5)
N1	0.06718 (7)	0.1229 (5)	−0.06616 (16)	0.0398 (5)
H1N	0.0665 (9)	0.182 (6)	−0.1257 (16)	0.048*
C1	0.14188 (7)	0.1197 (5)	0.01713 (19)	0.0388 (6)
C2	0.14276 (8)	0.1472 (6)	0.1219 (2)	0.0480 (7)
H2	0.1245	0.0541	0.1616	0.058*
C3	0.17086 (9)	0.3135 (7)	0.1669 (2)	0.0558 (8)
H3	0.1716	0.3346	0.2370	0.067*
C4	0.19760 (9)	0.4469 (7)	0.1072 (3)	0.0565 (8)
C5	0.19727 (10)	0.4182 (8)	0.0030 (3)	0.0700 (10)
H5	0.2158	0.5097	−0.0363	0.084*
C6	0.16932 (10)	0.2536 (7)	−0.0421 (2)	0.0584 (8)
H6	0.1688	0.2322	−0.1123	0.070*
C7	0.04271 (7)	0.2394 (5)	0.00549 (19)	0.0356 (5)
C8	0.01137 (7)	0.4226 (6)	−0.03950 (19)	0.0401 (6)
H81	−0.0074	0.3163	−0.0794	0.048*
H82	0.0242	0.5487	−0.0850	0.048*
O4	0.06513 (12)	0.6735 (8)	0.2409 (2)	0.1206 (13)
H41	0.0606	0.5373	0.2014	0.145*
H42	0.0704	0.7633	0.1885	0.145*

	U11	U22	U33	U12	U13	U23
Cl1	0.0731 (6)	0.0863 (7)	0.1142 (9)	−0.0383 (6)	−0.0254 (6)	0.0188 (6)
S1	0.0432 (4)	0.0384 (4)	0.0379 (3)	0.0079 (3)	0.0027 (2)	−0.0028 (3)
O1	0.0674 (13)	0.0645 (14)	0.0451 (11)	0.0189 (11)	0.0070 (9)	−0.0130 (10)
O2	0.0542 (12)	0.0363 (10)	0.0554 (12)	−0.0005 (9)	−0.0006 (9)	0.0030 (9)
O3	0.0513 (11)	0.0546 (12)	0.0365 (10)	0.0092 (9)	0.0058 (8)	0.0037 (9)
N1	0.0432 (12)	0.0440 (13)	0.0322 (10)	0.0089 (10)	−0.0001 (9)	−0.0004 (9)
C1	0.0340 (12)	0.0399 (14)	0.0425 (13)	0.0055 (11)	0.0039 (10)	0.0063 (11)
C2	0.0418 (14)	0.0598 (18)	0.0424 (14)	−0.0101 (13)	0.0040 (11)	0.0073 (13)
C3	0.0507 (16)	0.067 (2)	0.0496 (16)	−0.0113 (15)	−0.0025 (13)	0.0042 (15)
C4	0.0418 (15)	0.0547 (18)	0.073 (2)	−0.0087 (14)	−0.0095 (14)	0.0147 (16)
C5	0.0564 (19)	0.081 (3)	0.073 (2)	−0.0213 (18)	0.0103 (16)	0.025 (2)
C6	0.0558 (17)	0.073 (2)	0.0469 (16)	−0.0075 (16)	0.0102 (13)	0.0139 (15)
C7	0.0332 (12)	0.0350 (13)	0.0388 (13)	−0.0021 (10)	0.0010 (10)	−0.0040 (10)
C8	0.0348 (12)	0.0436 (14)	0.0419 (13)	0.0021 (11)	−0.0027 (10)	−0.0035 (12)
O4	0.180 (3)	0.131 (3)	0.0514 (14)	−0.070 (2)	0.0235 (17)	−0.0267 (17)

Cl1—C4	1.739 (3)	C3—C4	1.367 (4)
S1—O2	1.426 (2)	C3—H3	0.9300
S1—O1	1.426 (2)	C4—C5	1.380 (5)
S1—N1	1.644 (2)	C5—C6	1.371 (5)
S1—C1	1.756 (3)	C5—H5	0.9300
O3—C7	1.214 (3)	C6—H6	0.9300
N1—C7	1.382 (3)	C7—C8	1.503 (3)
N1—H1N	0.837 (19)	C8—C8i	1.506 (5)
C1—C6	1.381 (4)	C8—H81	0.9700
C1—C2	1.387 (4)	C8—H82	0.9700
C2—C3	1.379 (4)	O4—H41	0.8663
C2—H2	0.9300	O4—H42	0.8435
O2—S1—O1	119.62 (13)	C3—C4—Cl1	118.5 (3)
O2—S1—N1	108.89 (12)	C5—C4—Cl1	119.9 (2)
O1—S1—N1	104.31 (12)	C6—C5—C4	119.4 (3)
O2—S1—C1	108.73 (12)	C6—C5—H5	120.3
O1—S1—C1	108.76 (13)	C4—C5—H5	120.3
N1—S1—C1	105.65 (12)	C5—C6—C1	119.7 (3)
C7—N1—S1	125.20 (18)	C5—C6—H6	120.2
C7—N1—H1N	119 (2)	C1—C6—H6	120.2
S1—N1—H1N	114 (2)	O3—C7—N1	122.2 (2)
C6—C1—C2	120.6 (3)	O3—C7—C8	124.3 (2)
C6—C1—S1	119.6 (2)	N1—C7—C8	113.5 (2)
C2—C1—S1	119.8 (2)	C7—C8—C8i	113.0 (3)
C3—C2—C1	119.5 (3)	C7—C8—H81	109.0
C3—C2—H2	120.2	C8i—C8—H81	109.0
C1—C2—H2	120.2	C7—C8—H82	109.0
C4—C3—C2	119.3 (3)	C8i—C8—H82	109.0
C4—C3—H3	120.4	H81—C8—H82	107.8
C2—C3—H3	120.4	H41—O4—H42	87.6
C3—C4—C5	121.6 (3)
O2—S1—N1—C7	46.9 (3)	C2—C3—C4—C5	−0.3 (5)
O1—S1—N1—C7	175.7 (2)	C2—C3—C4—Cl1	178.8 (3)
C1—S1—N1—C7	−69.7 (2)	C3—C4—C5—C6	0.5 (6)
O2—S1—C1—C6	155.6 (2)	Cl1—C4—C5—C6	−178.6 (3)
O1—S1—C1—C6	23.9 (3)	C4—C5—C6—C1	0.2 (6)
N1—S1—C1—C6	−87.6 (3)	C2—C1—C6—C5	−1.0 (5)
O2—S1—C1—C2	−25.8 (3)	S1—C1—C6—C5	177.5 (3)
O1—S1—C1—C2	−157.6 (2)	S1—N1—C7—O3	−3.5 (4)
N1—S1—C1—C2	90.9 (2)	S1—N1—C7—C8	178.49 (19)
C6—C1—C2—C3	1.1 (5)	O3—C7—C8—C8i	9.9 (4)
S1—C1—C2—C3	−177.4 (2)	N1—C7—C8—C8i	−172.1 (3)
C1—C2—C3—C4	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4ii	0.84 (2)	1.90 (2)	2.735 (3)	178 (3)
O4—H41···O3	0.87	2.27	3.137 (4)	177
O4—H42···O2iii	0.84	2.23	2.941 (3)	142
O4—H42···O3iii	0.84	2.58	3.262 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.84 (2)	1.90 (2)	2.735 (3)	178 (3)
O4—H41⋯O3	0.87	2.27	3.137 (4)	177
O4—H42⋯O2ii	0.84	2.23	2.941 (3)	142
O4—H42⋯O3ii	0.84	2.58	3.262 (4)	139

Symmetry codes: (i) ; (ii) .