N,N'-(Ethane-1,2-di-yl)bis-(methane-sulfon-amide).

The mol-ecular structure of the title compound, C4H12N2O4S2, has crystallographic inversion symmetry. The central N-C-C-N moiety was refined as disordered over two sets of sites with an approximate occupancy ratio of 3:1 [0.742 (15):0.258 (15). In the crystal, N-H⋯O hydrogen bonds link adjacent mol-ecules into a thick sheet structure parallel to the b-axis direction.

Related literature

For analogous disulfonamide compounds, see: Al-Dajani et al. (2011a ▶,b ▶). For other analyses and properties of n class="Chemical">disulfonamide compounds, see: Alyar et al. (2011 ▶, 2012 ▶). For their biological and pharmaceutical activity, see: Sahu et al. (2007 ▶); Innocenti et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C4H12N2O4S2

M = 216.28

Monoclinic,

a = 10.5668 (11) Å

b = 5.6092 (6) Å

c = 8.5141 (9) Å

β = 109.790 (6)°

V = 474.84 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.54 mm−1

T = 296 K

0.30 × 0.28 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.854, T max = 0.948

10251 measured reflections

1115 independent reflections

1033 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.099

S = 1.10

1115 reflections

76 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814000622/nk2217sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000622/nk2217Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000622/nk2217Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000622/nk2217Isup4.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000622/nk2217Isup5.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C4H12N2O4S2	F(000) = 228
Mr = 216.28	Dx = 1.513 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5668 (11) Å	Cell parameters from 5915 reflections
b = 5.6092 (6) Å	θ = 2.7–27.7°
c = 8.5141 (9) Å	µ = 0.54 mm−1
β = 109.790 (6)°	T = 296 K
V = 474.84 (9) Å3	Plate, colourless
Z = 2	0.30 × 0.28 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	1033 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 27.7°, θmin = 2.1°
Tmin = 0.854, Tmax = 0.948	h = −13→13
10251 measured reflections	k = −7→7
1115 independent reflections	l = −11→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.1493P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.31 e Å−3
1115 reflections	Δρmin = −0.32 e Å−3
76 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.060 (8)

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.A disorder of the N—C—C—N chain in the molecule is observed. The occupancies were allowed to be refined freely. SADI restrains were used on the bond lengths of the S-N bond and the N—C bond. Furthermore, the hard constrain RIGU was placed on the displacement parameters of C2'. ISOR did not significantly improve the refinement.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.27263 (4)	0.10237 (7)	0.80849 (5)	0.0399 (2)
O1	0.22112 (17)	−0.0101 (3)	0.92544 (17)	0.0616 (4)
O2	0.34539 (14)	0.3196 (2)	0.85836 (18)	0.0564 (4)
C1	0.3769 (2)	−0.1041 (4)	0.7557 (3)	0.0599 (5)
H1A	0.4547	−0.1357	0.8519	0.090*
H1B	0.4046	−0.0397	0.6681	0.090*
H1C	0.3282	−0.2497	0.7184	0.090*
N1	0.1439 (6)	0.1585 (10)	0.6441 (5)	0.0419 (11)	0.742 (15)
H1	0.1218	0.3021	0.6106	0.050*	0.742 (15)
C2	0.0667 (4)	−0.0467 (5)	0.5549 (6)	0.0531 (12)	0.742 (15)
H2A	0.0546	−0.1622	0.6334	0.064*	0.742 (15)
H2B	0.1134	−0.1235	0.4882	0.064*	0.742 (15)
N1'	0.162 (2)	0.170 (3)	0.637 (2)	0.063 (5)	0.258 (15)
H1'	0.1771	0.2772	0.5731	0.076*	0.258 (15)
C2'	0.0165 (18)	0.026 (4)	0.5855 (12)	0.069 (5)	0.258 (15)
H2'A	0.0255	−0.1192	0.6502	0.082*	0.258 (15)
H2'B	−0.0520	0.1255	0.6046	0.082*	0.258 (15)

	U11	U22	U33	U12	U13	U23
S1	0.0482 (3)	0.0379 (3)	0.0328 (3)	−0.00469 (15)	0.01254 (19)	−0.00383 (13)
O1	0.0881 (10)	0.0592 (9)	0.0456 (8)	−0.0079 (8)	0.0331 (7)	0.0037 (6)
O2	0.0614 (8)	0.0464 (8)	0.0533 (8)	−0.0136 (6)	0.0088 (6)	−0.0113 (6)
C1	0.0590 (12)	0.0546 (12)	0.0642 (13)	0.0071 (9)	0.0185 (10)	−0.0093 (9)
N1	0.0397 (18)	0.0455 (19)	0.0334 (14)	−0.0088 (13)	0.0030 (11)	0.0088 (13)
C2	0.0401 (18)	0.0432 (13)	0.063 (2)	0.0043 (11)	0.0005 (15)	−0.0143 (12)
N1'	0.043 (6)	0.051 (7)	0.090 (11)	−0.003 (5)	0.015 (5)	−0.035 (7)
C2'	0.064 (7)	0.092 (11)	0.051 (5)	−0.034 (8)	0.021 (5)	−0.006 (5)

S1—O2	1.4267 (13)	N1—H1	0.8600
S1—O1	1.4327 (14)	C2—C2i	1.498 (6)
S1—N1'	1.574 (13)	C2—H2A	0.9700
S1—N1	1.619 (4)	C2—H2B	0.9700
S1—C1	1.758 (2)	N1'—C2'	1.66 (3)
C1—H1A	0.9600	N1'—H1'	0.8600
C1—H1B	0.9600	C2'—C2'i	1.41 (2)
C1—H1C	0.9600	C2'—H2'A	0.9700
N1—C2	1.465 (6)	C2'—H2'B	0.9700
O2—S1—O1	117.55 (9)	S1—N1—H1	121.5
O2—S1—N1'	103.0 (7)	N1—C2—C2i	106.8 (3)
O1—S1—N1'	114.5 (10)	N1—C2—H2A	110.4
O2—S1—N1	107.6 (2)	C2i—C2—H2A	110.4
O1—S1—N1	106.3 (2)	N1—C2—H2B	110.4
O2—S1—C1	108.52 (10)	C2i—C2—H2B	110.4
O1—S1—C1	107.80 (11)	H2A—C2—H2B	108.6
N1'—S1—C1	104.7 (7)	S1—N1'—C2'	117.2 (14)
N1—S1—C1	108.8 (2)	S1—N1'—H1'	121.4
S1—C1—H1A	109.5	C2'—N1'—H1'	121.4
S1—C1—H1B	109.5	C2'i—C2'—N1'	104.9 (14)
H1A—C1—H1B	109.5	C2'i—C2'—H2'A	110.8
S1—C1—H1C	109.5	N1'—C2'—H2'A	110.8
H1A—C1—H1C	109.5	C2'i—C2'—H2'B	110.8
H1B—C1—H1C	109.5	N1'—C2'—H2'B	110.8
C2—N1—S1	116.9 (3)	H2'A—C2'—H2'B	108.8
C2—N1—H1	121.5
O2—S1—N1—C2	170.3 (5)	O2—S1—N1'—C2'	−149.8 (15)
O1—S1—N1—C2	−63.0 (6)	O1—S1—N1'—C2'	−21.0 (18)
N1'—S1—N1—C2	113 (6)	N1—S1—N1'—C2'	−25 (5)
C1—S1—N1—C2	52.9 (6)	C1—S1—N1'—C2'	96.8 (17)
S1—N1—C2—C2i	162.7 (5)	S1—N1'—C2'—C2'i	−138 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.86	2.46	3.009 (6)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.46	3.009 (6)	122

Symmetry code: (i) .