N,N'-Bis(2-chloro-phenyl-sulfon-yl)adipamide.

In the centrosymmetric title compound, C(18)H(18)Cl(2)N(2)O(6)S(2), the conformation of the N-H and C=O bonds in the C-SO(2)-NH-C(O)-C-C segment is anti to each other. The dihedral angle between the planes of the benzene ring and the central part of the molecule is 89.6 (2)°. In the crystal, inter-molecular N-H⋯O(S) hydrogen bonds link the mol-ecules into sheets along the b axis.

Related literature

For the effect of substituents on the structures of amides and sulfonamides, see: Gowda et al. (2000 ▶, 2005 ▶); Rodrigues et al. (2011 ▶).

Experimental

Crystal data

C18H18Cl2N2O6S2

M = 493.36

Monoclinic,

a = 11.899 (2) Å

b = 5.564 (1) Å

c = 16.333 (3) Å

β = 96.56 (2)°

V = 1074.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.54 mm−1

T = 293 K

0.44 × 0.08 × 0.01 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.799, T max = 0.995

3439 measured reflections

1971 independent reflections

1120 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.089

wR(F 2) = 0.143

S = 1.26

1971 reflections

139 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.30 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/S1600536811008464/bq2284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008464/bq2284Isup2.hkl

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

C18H18Cl2N2O6S2	F(000) = 508
Mr = 493.36	Dx = 1.525 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 660 reflections
a = 11.899 (2) Å	θ = 2.9–27.9°
b = 5.564 (1) Å	µ = 0.54 mm−1
c = 16.333 (3) Å	T = 293 K
β = 96.56 (2)°	Needle, colourless
V = 1074.3 (3) Å3	0.44 × 0.08 × 0.01 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1971 independent reflections
Radiation source: fine-focus sealed tube	1120 reflections with I > 2σ(I)
graphite	Rint = 0.049
Rotation method data acquisition using ω scans.	θmax = 25.7°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→14
Tmin = 0.799, Tmax = 0.995	k = −6→6
3439 measured reflections	l = −19→17

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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ2(Fo2) + (0.0112P)2 + 2.7686P] where P = (Fo2 + 2Fc2)/3
1971 reflections	(Δ/σ)max = 0.004
139 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.30 e Å−3

Experimental. 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	−0.14610 (17)	0.2330 (4)	0.10849 (12)	0.0762 (7)
S1	−0.08046 (13)	−0.2093 (3)	0.23869 (9)	0.0378 (4)
O1	−0.1884 (3)	−0.2383 (8)	0.1916 (2)	0.0465 (12)
O2	−0.0261 (4)	−0.4127 (8)	0.2782 (3)	0.0538 (13)
O3	0.0751 (3)	0.0106 (9)	0.3729 (2)	0.0498 (13)
N1	−0.1028 (4)	−0.0070 (10)	0.3079 (3)	0.0365 (13)
H1N	−0.166 (3)	0.059 (10)	0.302 (3)	0.044*
C1	0.0147 (5)	−0.0762 (12)	0.1772 (3)	0.0361 (15)
C2	−0.0119 (6)	0.1105 (12)	0.1239 (4)	0.0470 (18)
C3	0.0707 (8)	0.2089 (17)	0.0807 (5)	0.081 (3)
H3	0.0530	0.3363	0.0447	0.098*
C4	0.1783 (9)	0.119 (2)	0.0912 (6)	0.098 (3)
H4	0.2336	0.1867	0.0627	0.118*
C5	0.2053 (7)	−0.069 (2)	0.1429 (6)	0.087 (3)
H5	0.2783	−0.1315	0.1486	0.105*
C6	0.1249 (6)	−0.1668 (15)	0.1864 (4)	0.060 (2)
H6	0.1437	−0.2941	0.2222	0.072*
C7	−0.0219 (5)	0.0781 (11)	0.3683 (4)	0.0349 (15)
C8	−0.0660 (4)	0.2510 (12)	0.4273 (3)	0.0375 (15)
H8A	−0.1021	0.1608	0.4679	0.045*
H8B	−0.1233	0.3515	0.3973	0.045*
C9	0.0245 (5)	0.4113 (11)	0.4718 (3)	0.0389 (16)
H9A	0.0803	0.3122	0.5039	0.047*
H9B	0.0625	0.4984	0.4315	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0866 (15)	0.0669 (15)	0.0744 (14)	0.0315 (13)	0.0064 (11)	0.0128 (12)
S1	0.0402 (9)	0.0383 (10)	0.0347 (9)	−0.0033 (8)	0.0034 (7)	−0.0051 (9)
O1	0.033 (2)	0.056 (3)	0.048 (3)	−0.014 (2)	−0.0038 (19)	−0.013 (2)
O2	0.076 (3)	0.035 (3)	0.049 (3)	0.002 (3)	0.001 (2)	0.003 (2)
O3	0.036 (2)	0.061 (3)	0.051 (3)	0.008 (2)	−0.005 (2)	−0.016 (2)
N1	0.028 (3)	0.047 (4)	0.035 (3)	0.002 (3)	0.002 (2)	−0.008 (3)
C1	0.038 (4)	0.039 (4)	0.031 (4)	−0.005 (3)	0.006 (3)	−0.005 (3)
C2	0.059 (4)	0.035 (4)	0.048 (4)	0.006 (3)	0.011 (4)	−0.003 (4)
C3	0.108 (8)	0.072 (6)	0.070 (6)	−0.004 (6)	0.036 (5)	0.022 (5)
C4	0.084 (7)	0.120 (10)	0.101 (8)	−0.021 (7)	0.054 (6)	0.008 (7)
C5	0.052 (5)	0.124 (9)	0.091 (7)	0.005 (6)	0.030 (5)	−0.006 (7)
C6	0.050 (4)	0.080 (6)	0.051 (5)	0.005 (4)	0.014 (4)	0.004 (4)
C7	0.030 (3)	0.039 (4)	0.036 (4)	−0.002 (3)	0.003 (3)	0.009 (3)
C8	0.039 (3)	0.045 (4)	0.028 (3)	0.002 (3)	0.005 (3)	−0.006 (3)
C9	0.041 (4)	0.038 (4)	0.036 (4)	0.006 (3)	−0.004 (3)	−0.006 (3)

Cl1—C2	1.728 (7)	C4—C5	1.359 (12)
S1—O2	1.421 (4)	C4—H4	0.9300
S1—O1	1.429 (4)	C5—C6	1.367 (10)
S1—N1	1.638 (5)	C5—H5	0.9300
S1—C1	1.760 (6)	C6—H6	0.9300
O3—C7	1.208 (6)	C7—C8	1.499 (8)
N1—C7	1.381 (7)	C8—C9	1.518 (7)
N1—H1N	0.84 (3)	C8—H8A	0.9700
C1—C2	1.370 (8)	C8—H8B	0.9700
C1—C6	1.397 (8)	C9—C9i	1.511 (11)
C2—C3	1.386 (9)	C9—H9A	0.9700
C3—C4	1.367 (11)	C9—H9B	0.9700
C3—H3	0.9300
O2—S1—O1	119.3 (3)	C4—C5—C6	119.9 (9)
O2—S1—N1	109.6 (3)	C4—C5—H5	120.1
O1—S1—N1	104.0 (2)	C6—C5—H5	120.1
O2—S1—C1	107.7 (3)	C5—C6—C1	120.4 (8)
O1—S1—C1	109.7 (3)	C5—C6—H6	119.8
N1—S1—C1	105.7 (3)	C1—C6—H6	119.8
C7—N1—S1	125.0 (4)	O3—C7—N1	121.4 (6)
C7—N1—H1N	119 (4)	O3—C7—C8	124.2 (5)
S1—N1—H1N	116 (4)	N1—C7—C8	114.4 (5)
C2—C1—C6	119.2 (6)	C7—C8—C9	113.8 (4)
C2—C1—S1	124.4 (5)	C7—C8—H8A	108.8
C6—C1—S1	116.4 (5)	C9—C8—H8A	108.8
C1—C2—C3	119.8 (7)	C7—C8—H8B	108.8
C1—C2—Cl1	122.3 (5)	C9—C8—H8B	108.8
C3—C2—Cl1	117.9 (6)	H8A—C8—H8B	107.7
C4—C3—C2	119.9 (8)	C9i—C9—C8	112.0 (6)
C4—C3—H3	120.0	C9i—C9—H9A	109.2
C2—C3—H3	120.0	C8—C9—H9A	109.2
C5—C4—C3	120.8 (8)	C9i—C9—H9B	109.2
C5—C4—H4	119.6	C8—C9—H9B	109.2
C3—C4—H4	119.6	H9A—C9—H9B	107.9
O2—S1—N1—C7	50.8 (6)	C1—C2—C3—C4	0.3 (12)
O1—S1—N1—C7	179.4 (5)	Cl1—C2—C3—C4	179.7 (7)
C1—S1—N1—C7	−65.1 (6)	C2—C3—C4—C5	0.8 (15)
O2—S1—C1—C2	173.5 (5)	C3—C4—C5—C6	−1.4 (16)
O1—S1—C1—C2	42.1 (6)	C4—C5—C6—C1	0.8 (13)
N1—S1—C1—C2	−69.5 (6)	C2—C1—C6—C5	0.3 (11)
O2—S1—C1—C6	−8.2 (6)	S1—C1—C6—C5	−178.1 (6)
O1—S1—C1—C6	−139.6 (5)	S1—N1—C7—O3	2.1 (9)
N1—S1—C1—C6	108.8 (5)	S1—N1—C7—C8	−176.2 (5)
C6—C1—C2—C3	−0.9 (10)	O3—C7—C8—C9	23.4 (9)
S1—C1—C2—C3	177.3 (6)	N1—C7—C8—C9	−158.5 (5)
C6—C1—C2—Cl1	179.8 (5)	C7—C8—C9—C9i	177.9 (6)
S1—C1—C2—Cl1	−1.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.84 (3)	2.08 (3)	2.901 (6)	168 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (3)	2.08 (3)	2.901 (6)	168 (6)

Symmetry code: (i) .