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

In the crystal of the title compound, C(20)H(22)Cl(2)N(2)O(6)S(2), the asymmetric unit comprises half of a mol-ecule, the remaining portion is generated via an inversion centre. The conformation of the N-H and C=O bonds in the SO(2)-NH-C(O)-C segment is anti. The mol-ecule is bent at the S atom with the C-SO(2)-NH-C(O) torsion angle being 68.16 (19)°. The dihedral angle between the plane of the benzene ring and the SO(2)-NH-C(O)-C segment is 77.5 (1)°. Hydrogen bonds of the type N-H⋯O(C) link mol-ecules into supra-molecular chains along the b axis.

Related literature

For the study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶). For the effect of substituents in N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶). For the effect of substituents on the structures of N-(aryl­sulfon­yl)-amides, see: Rodrigues et al. (2011 ▶).

Experimental

Crystal data

C20H22Cl2N2O6S2

M = 521.42

Monoclinic,

a = 7.8737 (9) Å

b = 9.717 (1) Å

c = 14.616 (2) Å

β = 94.575 (9)°

V = 1114.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.52 mm−1

T = 293 K

0.36 × 0.22 × 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 = 0.835, T max = 0.950

4126 measured reflections

2276 independent reflections

1744 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.05

2276 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.33 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/S1600536811009196/tk2727sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009196/tk2727Isup2.hkl

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

C20H22Cl2N2O6S2	F(000) = 540
Mr = 521.42	Dx = 1.553 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1476 reflections
a = 7.8737 (9) Å	θ = 2.6–27.7°
b = 9.717 (1) Å	µ = 0.52 mm−1
c = 14.616 (2) Å	T = 293 K
β = 94.575 (9)°	Prism, colourless
V = 1114.7 (2) Å3	0.36 × 0.22 × 0.10 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2276 independent reflections
Radiation source: fine-focus sealed tube	1744 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.835, Tmax = 0.950	k = −11→12
4126 measured reflections	l = −18→8

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1117P] where P = (Fo2 + 2Fc2)/3
2276 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.33 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
C1	0.3294 (3)	−0.0856 (2)	0.61075 (13)	0.0301 (5)
C2	0.2763 (3)	−0.0520 (2)	0.52035 (14)	0.0329 (5)
C3	0.3042 (3)	−0.1437 (3)	0.45110 (15)	0.0449 (6)
H3	0.2664	−0.1228	0.3908	0.054*
C4	0.3873 (4)	−0.2654 (3)	0.47050 (17)	0.0499 (7)
H4	0.4073	−0.3258	0.4232	0.060*
C5	0.4412 (3)	−0.2986 (3)	0.55920 (18)	0.0479 (6)
H5	0.4977	−0.3813	0.5719	0.057*
C6	0.4118 (3)	−0.2096 (2)	0.62958 (16)	0.0381 (5)
H6	0.4473	−0.2327	0.6898	0.046*
C7	0.0104 (3)	−0.0734 (2)	0.75061 (14)	0.0306 (5)
C8	−0.1521 (3)	−0.0352 (2)	0.79001 (14)	0.0347 (5)
H8A	−0.2460	−0.0863	0.7594	0.042*
H8B	−0.1743	0.0622	0.7808	0.042*
C9	−0.1371 (3)	−0.0685 (2)	0.89303 (14)	0.0385 (6)
H9A	−0.2477	−0.0554	0.9167	0.046*
H9B	−0.1066	−0.1647	0.9011	0.046*
C10	−0.0071 (3)	0.0185 (3)	0.94906 (14)	0.0394 (6)
H10A	−0.0384	0.1147	0.9422	0.047*
H10B	0.1034	0.0065	0.9252	0.047*
N1	0.1046 (2)	0.03505 (19)	0.72033 (12)	0.0316 (4)
H1N	0.066 (3)	0.1134 (18)	0.7259 (16)	0.038*
O1	0.3959 (2)	−0.03761 (18)	0.78343 (10)	0.0456 (4)
O2	0.3555 (2)	0.16371 (17)	0.68236 (10)	0.0415 (4)
O3	0.0630 (2)	−0.19135 (16)	0.74794 (11)	0.0437 (4)
Cl1	0.17624 (9)	0.10214 (7)	0.49044 (4)	0.0505 (2)
S1	0.31012 (7)	0.02626 (6)	0.70503 (3)	0.03155 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0299 (11)	0.0338 (12)	0.0268 (10)	−0.0019 (9)	0.0051 (8)	−0.0017 (9)
C2	0.0336 (12)	0.0347 (12)	0.0305 (11)	−0.0013 (10)	0.0026 (9)	0.0015 (9)
C3	0.0513 (15)	0.0557 (16)	0.0275 (11)	−0.0037 (13)	0.0025 (11)	−0.0034 (11)
C4	0.0576 (17)	0.0482 (16)	0.0459 (14)	−0.0019 (13)	0.0167 (12)	−0.0152 (12)
C5	0.0488 (16)	0.0374 (14)	0.0586 (16)	0.0075 (11)	0.0113 (13)	−0.0039 (12)
C6	0.0377 (13)	0.0377 (13)	0.0390 (12)	0.0018 (10)	0.0038 (10)	0.0024 (10)
C7	0.0389 (12)	0.0300 (12)	0.0232 (9)	−0.0026 (10)	0.0040 (9)	−0.0009 (9)
C8	0.0356 (12)	0.0334 (12)	0.0353 (12)	−0.0025 (10)	0.0045 (9)	0.0021 (10)
C9	0.0441 (14)	0.0399 (14)	0.0329 (12)	−0.0059 (11)	0.0123 (10)	−0.0002 (10)
C10	0.0453 (14)	0.0409 (14)	0.0335 (12)	−0.0062 (11)	0.0125 (10)	−0.0010 (10)
N1	0.0384 (11)	0.0264 (10)	0.0310 (9)	0.0014 (8)	0.0092 (8)	0.0012 (8)
O1	0.0493 (11)	0.0561 (11)	0.0298 (8)	0.0067 (8)	−0.0074 (7)	−0.0001 (8)
O2	0.0447 (10)	0.0362 (9)	0.0440 (9)	−0.0111 (7)	0.0068 (7)	−0.0030 (7)
O3	0.0529 (11)	0.0277 (9)	0.0527 (10)	0.0006 (8)	0.0187 (8)	−0.0006 (7)
Cl1	0.0632 (4)	0.0445 (4)	0.0418 (3)	0.0062 (3)	−0.0077 (3)	0.0065 (3)
S1	0.0340 (3)	0.0352 (3)	0.0253 (3)	−0.0016 (2)	0.0016 (2)	−0.0017 (2)

C1—C6	1.385 (3)	C7—C8	1.492 (3)
C1—C2	1.393 (3)	C8—C9	1.535 (3)
C1—S1	1.771 (2)	C8—H8A	0.9700
C2—C3	1.379 (3)	C8—H8B	0.9700
C2—Cl1	1.732 (2)	C9—C10	1.516 (3)
C3—C4	1.370 (4)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.370 (4)	C10—C10i	1.527 (4)
C4—H4	0.9300	C10—H10A	0.9700
C5—C6	1.378 (3)	C10—H10B	0.9700
C5—H5	0.9300	N1—S1	1.6532 (19)
C6—H6	0.9300	N1—H1N	0.826 (16)
C7—O3	1.221 (3)	O1—S1	1.4250 (16)
C7—N1	1.381 (3)	O2—S1	1.4282 (17)
C6—C1—C2	119.5 (2)	C7—C8—H8B	109.9
C6—C1—S1	116.55 (16)	C9—C8—H8B	109.9
C2—C1—S1	123.79 (17)	H8A—C8—H8B	108.3
C3—C2—C1	119.4 (2)	C10—C9—C8	114.08 (18)
C3—C2—Cl1	118.01 (18)	C10—C9—H9A	108.7
C1—C2—Cl1	122.59 (17)	C8—C9—H9A	108.7
C4—C3—C2	120.5 (2)	C10—C9—H9B	108.7
C4—C3—H3	119.8	C8—C9—H9B	108.7
C2—C3—H3	119.8	H9A—C9—H9B	107.6
C5—C4—C3	120.4 (2)	C9—C10—C10i	112.9 (2)
C5—C4—H4	119.8	C9—C10—H10A	109.0
C3—C4—H4	119.8	C10i—C10—H10A	109.0
C4—C5—C6	120.1 (2)	C9—C10—H10B	109.0
C4—C5—H5	120.0	C10i—C10—H10B	109.0
C6—C5—H5	120.0	H10A—C10—H10B	107.8
C5—C6—C1	120.1 (2)	C7—N1—S1	124.07 (16)
C5—C6—H6	119.9	C7—N1—H1N	117.4 (17)
C1—C6—H6	119.9	S1—N1—H1N	115.6 (17)
O3—C7—N1	120.9 (2)	O1—S1—O2	118.86 (10)
O3—C7—C8	123.3 (2)	O1—S1—N1	108.65 (10)
N1—C7—C8	115.66 (19)	O2—S1—N1	104.39 (10)
C7—C8—C9	108.97 (18)	O1—S1—C1	107.08 (11)
C7—C8—H8A	109.9	O2—S1—C1	110.79 (10)
C9—C8—H8A	109.9	N1—S1—C1	106.41 (10)
C6—C1—C2—C3	1.0 (3)	C7—C8—C9—C10	66.2 (3)
S1—C1—C2—C3	176.93 (18)	C8—C9—C10—C10i	−179.1 (2)
C6—C1—C2—Cl1	−178.69 (17)	O3—C7—N1—S1	−17.2 (3)
S1—C1—C2—Cl1	−2.8 (3)	C8—C7—N1—S1	160.00 (15)
C1—C2—C3—C4	−1.7 (4)	C7—N1—S1—O1	−46.8 (2)
Cl1—C2—C3—C4	178.1 (2)	C7—N1—S1—O2	−174.61 (16)
C2—C3—C4—C5	1.1 (4)	C7—N1—S1—C1	68.16 (19)
C3—C4—C5—C6	0.1 (4)	C6—C1—S1—O1	2.7 (2)
C4—C5—C6—C1	−0.7 (4)	C2—C1—S1—O1	−173.29 (18)
C2—C1—C6—C5	0.2 (3)	C6—C1—S1—O2	133.79 (17)
S1—C1—C6—C5	−176.03 (19)	C2—C1—S1—O2	−42.2 (2)
O3—C7—C8—C9	64.1 (3)	C6—C1—S1—N1	−113.32 (17)
N1—C7—C8—C9	−113.0 (2)	C2—C1—S1—N1	70.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ii	0.83 (2)	2.20 (2)	3.020 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.83 (2)	2.20 (2)	3.020 (2)	172 (2)

Symmetry code: (i) .