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

The asymmetric unit of the title compound, C(20)H(22)Cl(2)N(2)O(6)S(2), contains one half-mol-ecule with a center of symmetry at the mid-point of the central C-C bond. The conformations of all the N-H, C=O and C-H bonds in the central amide and aliphatic segments are anti to their adjacent bonds. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C(O) torsion angle of -80.6 (4)°. The dihedral angle between the benzene ring and the SO(2)-NH-C(O)-CH(2)-CH(2)-CH(2) segment is 79.5 (2)°. In the crystal, inter-molecular N-H⋯O(C) and N-H⋯O(S) hydrogen bonds link the mol-ecules into chains along the b axis.

Related literature

For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶, 2007 ▶), on N-(aryl­sulfon­yl)-amides, see: Rodrigues et al. (2011 ▶) and on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C20H22Cl2N2O6S2

M = 521.42

Monoclinic,

a = 21.925 (4) Å

b = 5.5855 (8) Å

c = 9.381 (1) Å

β = 93.91 (1)°

V = 1146.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 293 K

0.48 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.793, T max = 0.970

3854 measured reflections

2081 independent reflections

1522 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.115

S = 1.18

2081 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.32 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/S1600536811028662/sj6195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028662/sj6195Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028662/sj6195Isup3.cml

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

C20H22Cl2N2O6S2	F(000) = 540
Mr = 521.42	Dx = 1.511 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1226 reflections
a = 21.925 (4) Å	θ = 2.8–27.9°
b = 5.5855 (8) Å	µ = 0.51 mm−1
c = 9.381 (1) Å	T = 293 K
β = 93.91 (1)°	Needle, colourless
V = 1146.1 (3) Å3	0.48 × 0.14 × 0.06 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2081 independent reflections
Radiation source: fine-focus sealed tube	1522 reflections with I > 2σ(I)
graphite	Rint = 0.029
Rotation method data acquisition using ω scans.	θmax = 25.3°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −24→26
Tmin = 0.793, Tmax = 0.970	k = −6→5
3854 measured reflections	l = −11→9

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ2(Fo2) + (0.P)2 + 2.6128P] where P = (Fo2 + 2Fc2)/3
2081 reflections	(Δ/σ)max = 0.009
148 parameters	Δρmax = 0.29 e Å−3
1 restraint	Δρmin = −0.32 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	0.04045 (6)	0.7957 (3)	0.3395 (2)	0.1014 (6)
S1	0.26694 (5)	0.1182 (2)	0.39060 (10)	0.0397 (3)
O1	0.25535 (13)	−0.0692 (5)	0.4882 (3)	0.0482 (8)
O2	0.28271 (13)	0.0610 (5)	0.2497 (3)	0.0486 (8)
O3	0.35809 (14)	0.4648 (6)	0.2761 (3)	0.0608 (10)
N1	0.32305 (15)	0.2771 (6)	0.4690 (3)	0.0397 (8)
H1N	0.3190 (18)	0.284 (7)	0.559 (2)	0.048*
C1	0.20287 (18)	0.3113 (8)	0.3787 (4)	0.0405 (10)
C2	0.1531 (2)	0.2614 (9)	0.4551 (5)	0.0573 (13)
H2	0.1534	0.1285	0.5148	0.069*
C3	0.1026 (2)	0.4101 (10)	0.4425 (6)	0.0694 (15)
H3	0.0686	0.3776	0.4932	0.083*
C4	0.1034 (2)	0.6059 (9)	0.3547 (6)	0.0596 (13)
C5	0.1531 (2)	0.6559 (9)	0.2780 (5)	0.0551 (12)
H5	0.1527	0.7886	0.2181	0.066*
C6	0.2034 (2)	0.5079 (8)	0.2906 (4)	0.0470 (11)
H6	0.2374	0.5407	0.2399	0.056*
C7	0.35867 (17)	0.4445 (8)	0.4041 (4)	0.0378 (10)
C8	0.39757 (17)	0.5930 (8)	0.5078 (4)	0.0389 (10)
H8A	0.4223	0.4876	0.5703	0.047*
H8B	0.3713	0.6846	0.5665	0.047*
C9	0.43924 (18)	0.7634 (8)	0.4345 (4)	0.0409 (10)
H9A	0.4651	0.6715	0.3749	0.049*
H9B	0.4144	0.8693	0.3726	0.049*
C10	0.47944 (17)	0.9135 (8)	0.5373 (4)	0.0394 (10)
H10A	0.5048	0.8079	0.5984	0.047*
H10B	0.4537	1.0041	0.5978	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0516 (8)	0.0761 (11)	0.1751 (18)	0.0094 (8)	−0.0036 (9)	−0.0021 (11)
S1	0.0432 (6)	0.0422 (6)	0.0343 (5)	−0.0088 (5)	0.0065 (4)	−0.0047 (5)
O1	0.0551 (18)	0.0452 (19)	0.0447 (16)	−0.0108 (15)	0.0069 (14)	0.0030 (14)
O2	0.0577 (19)	0.054 (2)	0.0353 (15)	−0.0070 (15)	0.0085 (13)	−0.0108 (14)
O3	0.063 (2)	0.086 (3)	0.0328 (16)	−0.0361 (19)	0.0026 (14)	0.0065 (16)
N1	0.0386 (18)	0.052 (2)	0.0298 (16)	−0.0161 (17)	0.0076 (15)	−0.0034 (17)
C1	0.042 (2)	0.043 (3)	0.036 (2)	−0.010 (2)	0.0002 (18)	−0.005 (2)
C2	0.044 (3)	0.064 (3)	0.065 (3)	−0.009 (3)	0.013 (2)	0.011 (3)
C3	0.041 (3)	0.078 (4)	0.091 (4)	−0.008 (3)	0.018 (3)	0.006 (3)
C4	0.040 (3)	0.054 (3)	0.083 (3)	−0.007 (2)	−0.009 (2)	−0.010 (3)
C5	0.063 (3)	0.044 (3)	0.057 (3)	−0.010 (2)	−0.004 (2)	0.004 (2)
C6	0.044 (3)	0.050 (3)	0.047 (2)	−0.008 (2)	0.007 (2)	−0.006 (2)
C7	0.028 (2)	0.050 (3)	0.036 (2)	−0.0030 (19)	0.0049 (17)	−0.0005 (19)
C8	0.035 (2)	0.049 (3)	0.034 (2)	−0.005 (2)	0.0056 (17)	−0.004 (2)
C9	0.040 (2)	0.044 (3)	0.038 (2)	−0.010 (2)	0.0075 (17)	−0.0012 (19)
C10	0.035 (2)	0.047 (3)	0.036 (2)	−0.005 (2)	0.0071 (17)	−0.0043 (19)

Cl1—C4	1.738 (5)	C4—C5	1.375 (6)
S1—O1	1.425 (3)	C5—C6	1.377 (6)
S1—O2	1.425 (3)	C5—H5	0.9300
S1—N1	1.649 (3)	C6—H6	0.9300
S1—C1	1.769 (4)	C7—C8	1.499 (5)
O3—C7	1.205 (4)	C8—C9	1.516 (5)
N1—C7	1.386 (5)	C8—H8A	0.9700
N1—H1N	0.852 (18)	C8—H8B	0.9700
C1—C2	1.374 (5)	C9—C10	1.515 (5)
C1—C6	1.375 (6)	C9—H9A	0.9700
C2—C3	1.382 (7)	C9—H9B	0.9700
C2—H2	0.9300	C10—C10i	1.525 (7)
C3—C4	1.370 (7)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
O1—S1—O2	119.75 (18)	C5—C6—C1	119.4 (4)
O1—S1—N1	105.61 (17)	C5—C6—H6	120.3
O2—S1—N1	108.29 (17)	C1—C6—H6	120.3
O1—S1—C1	108.25 (18)	O3—C7—N1	122.2 (4)
O2—S1—C1	108.65 (18)	O3—C7—C8	124.1 (4)
N1—S1—C1	105.37 (19)	N1—C7—C8	113.6 (3)
C7—N1—S1	126.4 (3)	C7—C8—C9	112.8 (3)
C7—N1—H1N	120 (3)	C7—C8—H8A	109.0
S1—N1—H1N	110 (3)	C9—C8—H8A	109.0
C2—C1—C6	121.0 (4)	C7—C8—H8B	109.0
C2—C1—S1	119.9 (4)	C9—C8—H8B	109.0
C6—C1—S1	119.1 (3)	H8A—C8—H8B	107.8
C1—C2—C3	119.6 (5)	C10—C9—C8	113.6 (3)
C1—C2—H2	120.2	C10—C9—H9A	108.8
C3—C2—H2	120.2	C8—C9—H9A	108.8
C4—C3—C2	119.3 (4)	C10—C9—H9B	108.8
C4—C3—H3	120.4	C8—C9—H9B	108.8
C2—C3—H3	120.4	H9A—C9—H9B	107.7
C3—C4—C5	121.2 (5)	C9—C10—C10i	113.2 (4)
C3—C4—Cl1	119.7 (4)	C9—C10—H10A	108.9
C5—C4—Cl1	119.1 (4)	C10i—C10—H10A	108.9
C6—C5—C4	119.5 (4)	C9—C10—H10B	108.9
C6—C5—H5	120.3	C10i—C10—H10B	108.9
C4—C5—H5	120.3	H10A—C10—H10B	107.7
O1—S1—N1—C7	165.0 (3)	C2—C3—C4—Cl1	−179.4 (4)
O2—S1—N1—C7	35.6 (4)	C3—C4—C5—C6	−0.7 (7)
C1—S1—N1—C7	−80.6 (4)	Cl1—C4—C5—C6	179.3 (3)
O1—S1—C1—C2	−1.3 (4)	C4—C5—C6—C1	0.6 (7)
O2—S1—C1—C2	130.2 (3)	C2—C1—C6—C5	−0.5 (6)
N1—S1—C1—C2	−113.9 (4)	S1—C1—C6—C5	178.4 (3)
O1—S1—C1—C6	179.8 (3)	S1—N1—C7—O3	−11.8 (6)
O2—S1—C1—C6	−48.7 (4)	S1—N1—C7—C8	168.7 (3)
N1—S1—C1—C6	67.1 (3)	O3—C7—C8—C9	−3.3 (6)
C6—C1—C2—C3	0.5 (7)	N1—C7—C8—C9	176.2 (3)
S1—C1—C2—C3	−178.5 (4)	C7—C8—C9—C10	−179.4 (3)
C1—C2—C3—C4	−0.5 (8)	C8—C9—C10—C10i	−179.2 (4)
C2—C3—C4—C5	0.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.85 (2)	2.19 (3)	2.975 (4)	153 (4)
N1—H1N···O3ii	0.85 (2)	2.57 (3)	3.227 (4)	135 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.19 (3)	2.975 (4)	153 (4)
N1—H1N⋯O3i	0.85 (2)	2.57 (3)	3.227 (4)	135 (3)

Symmetry code: (i) .