N,N'-(Ethane-1,2-di-yl)bis-(4-chloro-benzene-sulfonamide).

The title mol-ecule, C(14)H(14)Cl(2)N(2)O(4)S(2), lies on an inversion center. The mol-ecule is twisted in the region of the sulfonamide group with a C-S-N-C torsion angle of -67.49 (16)°. In the crystal, mol-ecules are connected via inter-molecular N-H⋯O and weak C-H⋯O hydrogen bonds, forming layers parallel to (100).

Related literature

For details of the chemistry of sulfonamides, see: Gowda et al. (2003 ▶, 2007 ▶). For related structures, see: O’Connor & Maslen (1965 ▶); Kumar et al. (1992 ▶); Shakuntala et al. (2011 ▶).

Experimental

Crystal data

C14H14Cl2N2O4S2

M = 409.29

Monoclinic,

a = 13.2640 (5) Å

b = 5.3390 (2) Å

c = 13.1792 (5) Å

β = 110.270 (1)°

V = 875.51 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.63 mm−1

T = 296 K

0.86 × 0.42 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.613, T max = 0.925

25142 measured reflections

3689 independent reflections

2869 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.175

S = 1.03

3689 reflections

114 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.84 e Å−3

Δρmin = −0.71 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028443/lh5285sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028443/lh5285Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028443/lh5285Isup3.cml

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

C14H14Cl2N2O4S2	F(000) = 420
Mr = 409.29	Dx = 1.553 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9471 reflections
a = 13.2640 (5) Å	θ = 3.3–33.5°
b = 5.3390 (2) Å	µ = 0.63 mm−1
c = 13.1792 (5) Å	T = 296 K
β = 110.270 (1)°	Plate, colourless
V = 875.51 (6) Å3	0.86 × 0.42 × 0.13 mm
Z = 2

Bruker APEXII DUO CCD area-detector diffractometer	3689 independent reflections
Radiation source: fine-focus sealed tube	2869 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 34.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.613, Tmax = 0.925	k = −8→8
25142 measured reflections	l = −19→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.0979P)2 + 0.221P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3689 reflections	Δρmax = 0.84 e Å−3
114 parameters	Δρmin = −0.71 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (6)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.05348 (6)	1.46054 (14)	0.19657 (6)	0.0881 (2)
S1	0.35715 (3)	0.67863 (7)	0.09928 (3)	0.04701 (14)
O1	0.30882 (14)	0.5925 (3)	−0.00946 (11)	0.0722 (4)
O2	0.39055 (12)	0.5017 (2)	0.18611 (12)	0.0615 (3)
N1	0.46306 (13)	0.8326 (3)	0.10557 (14)	0.0537 (3)
C1	0.18737 (14)	1.0017 (4)	0.04025 (13)	0.0572 (4)
H1A	0.1784	0.9592	−0.0308	0.069*
C2	0.12110 (16)	1.1788 (4)	0.06200 (16)	0.0648 (5)
H2A	0.0680	1.2581	0.0056	0.078*
C3	0.13465 (14)	1.2362 (4)	0.16811 (17)	0.0564 (4)
C4	0.21201 (17)	1.1220 (4)	0.25315 (15)	0.0602 (4)
H4A	0.2191	1.1612	0.3240	0.072*
C5	0.27916 (15)	0.9482 (4)	0.23194 (12)	0.0543 (4)
H5A	0.3325	0.8707	0.2888	0.065*
C6	0.26714 (11)	0.8888 (3)	0.12547 (11)	0.0428 (3)
C7	0.45903 (17)	1.0240 (4)	0.02466 (18)	0.0635 (5)
H7A	0.4710	1.1877	0.0587	0.076*
H7B	0.3884	1.0241	−0.0311	0.076*
H1N1	0.496 (2)	0.868 (6)	0.166 (2)	0.076 (8)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0889 (4)	0.0823 (4)	0.1081 (5)	0.0331 (3)	0.0532 (4)	0.0217 (3)
S1	0.0555 (2)	0.0437 (2)	0.03914 (19)	−0.00060 (14)	0.01292 (15)	−0.00090 (12)
O1	0.0873 (10)	0.0712 (9)	0.0468 (6)	0.0035 (8)	0.0090 (6)	−0.0168 (6)
O2	0.0717 (8)	0.0495 (7)	0.0620 (7)	0.0049 (6)	0.0214 (6)	0.0146 (5)
N1	0.0538 (7)	0.0590 (8)	0.0516 (7)	0.0028 (6)	0.0226 (6)	0.0065 (6)
C1	0.0508 (8)	0.0756 (12)	0.0390 (7)	0.0038 (7)	0.0079 (6)	0.0079 (7)
C2	0.0524 (9)	0.0799 (13)	0.0563 (9)	0.0152 (8)	0.0113 (7)	0.0193 (9)
C3	0.0522 (8)	0.0566 (9)	0.0653 (10)	0.0068 (7)	0.0265 (7)	0.0122 (8)
C4	0.0711 (11)	0.0637 (10)	0.0484 (8)	0.0112 (9)	0.0241 (8)	0.0060 (7)
C5	0.0620 (9)	0.0605 (9)	0.0374 (6)	0.0110 (7)	0.0135 (6)	0.0078 (6)
C6	0.0431 (6)	0.0460 (7)	0.0366 (5)	−0.0031 (5)	0.0104 (5)	0.0047 (5)
C7	0.0724 (11)	0.0577 (10)	0.0775 (12)	0.0207 (8)	0.0477 (10)	0.0202 (9)

Cl1—C3	1.7359 (19)	C2—C3	1.381 (3)
S1—O1	1.4282 (14)	C2—H2A	0.9300
S1—O2	1.4308 (13)	C3—C4	1.373 (3)
S1—N1	1.6048 (16)	C4—C5	1.380 (3)
S1—C6	1.7574 (16)	C4—H4A	0.9300
N1—C7	1.465 (2)	C5—C6	1.393 (2)
N1—H1N1	0.78 (3)	C5—H5A	0.9300
C1—C6	1.386 (2)	C7—C7i	1.469 (3)
C1—C2	1.387 (3)	C7—H7A	0.9700
C1—H1A	0.9300	C7—H7B	0.9700
O1—S1—O2	119.79 (10)	C2—C3—Cl1	119.94 (14)
O1—S1—N1	107.30 (10)	C3—C4—C5	119.05 (17)
O2—S1—N1	105.90 (9)	C3—C4—H4A	120.5
O1—S1—C6	107.66 (8)	C5—C4—H4A	120.5
O2—S1—C6	107.92 (8)	C4—C5—C6	120.03 (15)
N1—S1—C6	107.76 (8)	C4—C5—H5A	120.0
C7—N1—S1	120.62 (14)	C6—C5—H5A	120.0
C7—N1—H1N1	116 (2)	C1—C6—C5	120.40 (16)
S1—N1—H1N1	110 (2)	C1—C6—S1	119.90 (12)
C6—C1—C2	119.32 (16)	C5—C6—S1	119.66 (11)
C6—C1—H1A	120.3	N1—C7—C7i	110.75 (19)
C2—C1—H1A	120.3	N1—C7—H7A	109.5
C3—C2—C1	119.42 (16)	C7i—C7—H7A	109.5
C3—C2—H2A	120.3	N1—C7—H7B	109.5
C1—C2—H2A	120.3	C7i—C7—H7B	109.5
C4—C3—C2	121.75 (18)	H7A—C7—H7B	108.1
C4—C3—Cl1	118.31 (16)
O1—S1—N1—C7	48.19 (17)	C2—C1—C6—S1	−176.04 (15)
O2—S1—N1—C7	177.22 (15)	C4—C5—C6—C1	−0.5 (3)
C6—S1—N1—C7	−67.49 (16)	C4—C5—C6—S1	176.93 (15)
C6—C1—C2—C3	−1.0 (3)	O1—S1—C6—C1	−20.18 (17)
C1—C2—C3—C4	−0.2 (3)	O2—S1—C6—C1	−150.79 (14)
C1—C2—C3—Cl1	179.13 (16)	N1—S1—C6—C1	95.26 (15)
C2—C3—C4—C5	1.1 (3)	O1—S1—C6—C5	162.35 (16)
Cl1—C3—C4—C5	−178.26 (16)	O2—S1—C6—C5	31.74 (16)
C3—C4—C5—C6	−0.7 (3)	N1—S1—C6—C5	−82.21 (15)
C2—C1—C6—C5	1.4 (3)	S1—N1—C7—C7i	−126.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ii	0.79 (3)	2.13 (3)	2.903 (2)	167 (3)
C4—H4A···O1iii	0.93	2.50	3.157 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.79 (3)	2.13 (3)	2.903 (2)	167 (3)
C4—H4A⋯O1ii	0.93	2.50	3.157 (2)	127

Symmetry codes: (i) ; (ii) .