N,N'-Bis(4-chloro-phenyl-sulfon-yl)-adipamide.

In the title compound, C(18)H(18)Cl(2)N(2)O(6)S(2), the asymmetric unit contains half a mol-ecule with a center of symmetry at the mid-point of the central C-C bond. The dihedral angle between the benzene ring and the SO(2)-NH-C(O) segment in the two halves of the mol-ecule is 83.5 (2)°. In the crystal, N-H⋯O(S) inter-molecular hydrogen bonds link the mol-ecules into infinite chains running along the c axis. The O atom involved in the hydrogen bond has a longer S-O bond than the other O atom bonded to S [1.403 (4) versus 1.361 (4) Å].

Related literature

For hydrogen-bonding preferences of sulfonamides, see; Adsmond & Grant (2001 ▶). For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2000 ▶, 2007 ▶). For those on N-(aryl­sulfon­yl)-amides, see: Rodrigues et al. (2011 ▶). For those on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C18H18Cl2N2O6S2

M = 493.36

Triclinic,

a = 5.593 (1) Å

b = 8.827 (2) Å

c = 9.908 (2) Å

α = 89.28 (2)°

β = 87.75 (2)°

γ = 81.16 (1)°

V = 482.96 (17) Å3

Z = 1

Mo Kα radiation

μ = 0.60 mm−1

T = 293 K

0.12 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.932, T max = 0.977

2942 measured reflections

1757 independent reflections

775 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.104

S = 0.99

1757 reflections

139 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.36 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 datablock(s) I, global. DOI: 10.1107/S1600536811030029/zj2018sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030029/zj2018Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030029/zj2018Isup3.cml

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

C18H18Cl2N2O6S2	Z = 1
Mr = 493.36	F(000) = 254
Triclinic, P1	Dx = 1.696 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.593 (1) Å	Cell parameters from 528 reflections
b = 8.827 (2) Å	θ = 3.1–28.0°
c = 9.908 (2) Å	µ = 0.60 mm−1
α = 89.28 (2)°	T = 293 K
β = 87.75 (2)°	Needle, colourless
γ = 81.16 (1)°	0.12 × 0.08 × 0.04 mm
V = 482.96 (17) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1757 independent reflections
Radiation source: fine-focus sealed tube	775 reflections with I > 2σ(I)
graphite	Rint = 0.063
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→6
Tmin = 0.932, Tmax = 0.977	k = −10→10
2942 measured reflections	l = −11→11

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
1757 reflections	(Δ/σ)max = 0.007
139 parameters	Δρmax = 0.41 e Å−3
2 restraints	Δρmin = −0.36 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
C1	0.1041 (11)	0.6193 (7)	0.8224 (6)	0.0293 (17)
C2	0.2221 (12)	0.6416 (7)	0.9348 (6)	0.042 (2)
H2	0.3810	0.5932	0.9421	0.051*
C3	0.1175 (13)	0.7325 (8)	1.0388 (7)	0.047 (2)
H3	0.2030	0.7448	1.1155	0.057*
C4	−0.1031 (13)	0.8010 (8)	1.0280 (7)	0.042 (2)
C5	−0.2239 (12)	0.7794 (8)	0.9163 (7)	0.045 (2)
H5	−0.3822	0.8291	0.9100	0.054*
C6	−0.1242 (11)	0.6877 (7)	0.8116 (7)	0.0433 (19)
H6	−0.2120	0.6738	0.7361	0.052*
C7	0.3253 (12)	0.7659 (8)	0.5567 (7)	0.0357 (18)
C8	0.2725 (11)	0.8657 (7)	0.4335 (6)	0.0394 (18)
H8A	0.4234	0.8879	0.3921	0.047*
H8B	0.1936	0.8111	0.3683	0.047*
C9	0.1140 (10)	1.0122 (8)	0.4692 (6)	0.054 (2)
H9A	0.1970	1.0689	0.5309	0.065*
H9B	0.0846	1.0738	0.3881	0.065*
N1	0.2328 (10)	0.6336 (6)	0.5582 (5)	0.0371 (15)
H1N	0.149 (9)	0.600 (6)	0.499 (4)	0.044*
O1	0.4677 (8)	0.4551 (5)	0.7221 (4)	0.0501 (14)
O2	0.0961 (8)	0.4035 (5)	0.6456 (4)	0.0508 (14)
O3	0.4340 (7)	0.8007 (5)	0.6492 (5)	0.0491 (14)
Cl1	−0.2314 (4)	0.9221 (2)	1.15456 (19)	0.0695 (7)
S1	0.2378 (4)	0.5111 (2)	0.68742 (19)	0.0419 (5)

	U11	U22	U33	U12	U13	U23
C1	0.032 (4)	0.030 (4)	0.026 (4)	−0.004 (4)	−0.006 (3)	0.003 (3)
C2	0.035 (5)	0.049 (5)	0.039 (5)	0.004 (4)	−0.001 (4)	0.002 (4)
C3	0.047 (5)	0.060 (6)	0.031 (5)	0.005 (5)	−0.011 (4)	−0.001 (4)
C4	0.049 (5)	0.042 (5)	0.031 (5)	0.002 (4)	0.004 (4)	0.009 (4)
C5	0.026 (4)	0.056 (5)	0.049 (5)	0.005 (4)	0.000 (4)	0.005 (4)
C6	0.032 (4)	0.050 (5)	0.048 (5)	−0.004 (4)	−0.012 (4)	0.001 (4)
C7	0.024 (4)	0.040 (5)	0.041 (5)	−0.001 (4)	0.004 (4)	−0.013 (4)
C8	0.035 (4)	0.045 (5)	0.036 (5)	0.000 (4)	0.000 (3)	0.005 (4)
C9	0.042 (5)	0.064 (6)	0.053 (5)	0.001 (5)	−0.001 (4)	0.017 (4)
N1	0.041 (4)	0.037 (4)	0.035 (4)	−0.008 (3)	−0.010 (3)	−0.005 (3)
O1	0.036 (3)	0.058 (3)	0.050 (3)	0.013 (3)	−0.006 (2)	−0.003 (3)
O2	0.067 (4)	0.042 (3)	0.047 (3)	−0.017 (3)	−0.018 (3)	0.000 (3)
O3	0.031 (3)	0.062 (4)	0.055 (4)	−0.008 (3)	−0.012 (3)	−0.005 (3)
Cl1	0.0784 (16)	0.0701 (16)	0.0514 (14)	0.0107 (12)	0.0185 (12)	−0.0023 (12)
S1	0.0447 (13)	0.0403 (13)	0.0394 (12)	−0.0009 (11)	−0.0076 (10)	−0.0022 (11)

C1—C6	1.333 (6)	C7—N1	1.348 (7)
C1—C2	1.348 (8)	C7—C8	1.508 (8)
C1—S1	1.731 (6)	C8—C9	1.489 (7)
C2—C3	1.370 (7)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.295 (8)	C9—C9i	1.437 (10)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.350 (8)	C9—H9B	0.9700
C4—Cl1	1.719 (7)	N1—S1	1.664 (6)
C5—C6	1.371 (7)	N1—H1N	0.85 (2)
C5—H5	0.9300	O1—S1	1.361 (4)
C6—H6	0.9300	O2—S1	1.403 (4)
C7—O3	1.188 (7)
C6—C1—C2	119.0 (6)	C9—C8—C7	111.2 (5)
C6—C1—S1	117.8 (5)	C9—C8—H8A	109.4
C2—C1—S1	123.2 (5)	C7—C8—H8A	109.4
C1—C2—C3	122.7 (7)	C9—C8—H8B	109.4
C1—C2—H2	118.7	C7—C8—H8B	109.4
C3—C2—H2	118.7	H8A—C8—H8B	108.0
C4—C3—C2	118.6 (7)	C9i—C9—C8	112.4 (7)
C4—C3—H3	120.7	C9i—C9—H9A	109.1
C2—C3—H3	120.7	C8—C9—H9A	109.1
C3—C4—C5	119.4 (7)	C9i—C9—H9B	109.1
C3—C4—Cl1	119.0 (6)	C8—C9—H9B	109.1
C5—C4—Cl1	121.6 (6)	H9A—C9—H9B	107.9
C4—C5—C6	123.1 (7)	C7—N1—S1	125.5 (5)
C4—C5—H5	118.4	C7—N1—H1N	128 (4)
C6—C5—H5	118.4	S1—N1—H1N	106 (4)
C1—C6—C5	117.2 (6)	O1—S1—O2	116.6 (3)
C1—C6—H6	121.4	O1—S1—N1	112.0 (3)
C5—C6—H6	121.4	O2—S1—N1	103.7 (3)
O3—C7—N1	121.0 (7)	O1—S1—C1	106.7 (3)
O3—C7—C8	123.7 (7)	O2—S1—C1	112.4 (3)
N1—C7—C8	115.3 (6)	N1—S1—C1	105.0 (3)
C6—C1—C2—C3	−0.3 (10)	C7—C8—C9—C9i	−59.2 (9)
S1—C1—C2—C3	177.3 (5)	O3—C7—N1—S1	4.7 (9)
C1—C2—C3—C4	−0.6 (11)	C8—C7—N1—S1	−173.2 (4)
C2—C3—C4—C5	0.8 (11)	C7—N1—S1—O1	−60.3 (6)
C2—C3—C4—Cl1	−177.1 (5)	C7—N1—S1—O2	173.2 (5)
C3—C4—C5—C6	−0.2 (11)	C7—N1—S1—C1	55.0 (6)
Cl1—C4—C5—C6	177.8 (5)	C6—C1—S1—O1	179.5 (5)
C2—C1—C6—C5	1.0 (10)	C2—C1—S1—O1	1.8 (6)
S1—C1—C6—C5	−176.8 (4)	C6—C1—S1—O2	−51.6 (6)
C4—C5—C6—C1	−0.8 (10)	C2—C1—S1—O2	130.8 (5)
O3—C7—C8—C9	−63.7 (9)	C6—C1—S1—N1	60.5 (6)
N1—C7—C8—C9	114.2 (6)	C2—C1—S1—N1	−117.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.85 (2)	2.03 (3)	2.839 (7)	160 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.03 (3)	2.839 (7)	160 (6)

Symmetry code: (i) .