N,N'-Bis(phenyl-sulfon-yl)maleamide.

Mol-ecules of the title compound, C(16)H(14)N(2)O(6)S(2), show crystallographic inversion symmetry: there is one half-mol-ecule in the asymmetric unit. The structure exhibits both intramolecular and inter-molecular N-H⋯O hydrogen bonds.

Related literature

For our studies of the effect of ring and the side-chain substituents on the solid-state structures of N-aromatic sulfonamides, see: Gowda et al. (2009 ▶, 2010 ▶), Suchetan et al. (2009 ▶).

Experimental

Crystal data

C16H14N2O6S2

M = 394.41

Monoclinic,

a = 8.582 (1) Å

b = 5.1464 (6) Å

c = 19.691 (4) Å

β = 101.17 (2)°

V = 853.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 299 K

0.48 × 0.28 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.850, T max = 0.927

3236 measured reflections

1720 independent reflections

1500 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.07

1720 reflections

121 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 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 datablocks I, global. DOI: 10.1107/S1600536809053811/bt5141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053811/bt5141Isup2.hkl

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

C16H14N2O6S2	F(000) = 408
Mr = 394.41	Dx = 1.535 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1915 reflections
a = 8.582 (1) Å	θ = 2.8–27.7°
b = 5.1464 (6) Å	µ = 0.35 mm−1
c = 19.691 (4) Å	T = 299 K
β = 101.17 (2)°	Rod, colourless
V = 853.2 (2) Å3	0.48 × 0.28 × 0.22 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1720 independent reflections
Radiation source: fine-focus sealed tube	1500 reflections with I > 2σ(I)
graphite	Rint = 0.009
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→10
Tmin = 0.850, Tmax = 0.927	k = −6→6
3236 measured reflections	l = −24→14

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.3647P] where P = (Fo2 + 2Fc2)/3
1720 reflections	(Δ/σ)max = 0.004
121 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.32 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	0.81684 (18)	0.2173 (3)	0.31947 (8)	0.0310 (3)
C2	0.7033 (2)	0.0409 (3)	0.28846 (9)	0.0406 (4)
H2	0.6715	−0.0947	0.3139	0.049*
C3	0.6381 (2)	0.0704 (4)	0.21881 (10)	0.0539 (5)
H3	0.5618	−0.0465	0.1971	0.065*
C4	0.6857 (3)	0.2717 (4)	0.18171 (10)	0.0548 (5)
H4	0.6417	0.2894	0.1349	0.066*
C5	0.7979 (3)	0.4475 (4)	0.21310 (11)	0.0539 (5)
H5	0.8287	0.5837	0.1876	0.065*
C6	0.8651 (2)	0.4217 (4)	0.28269 (10)	0.0438 (4)
H6	0.9410	0.5393	0.3043	0.053*
C7	0.64152 (19)	0.3130 (3)	0.45450 (8)	0.0351 (4)
C8	0.57352 (19)	0.5096 (3)	0.49559 (8)	0.0370 (4)
H8	0.6360	0.6481	0.5153	0.044*
N1	0.79828 (16)	0.3588 (3)	0.45084 (8)	0.0367 (3)
H1N	0.842 (2)	0.498 (3)	0.4667 (10)	0.044*
O1	1.05692 (13)	0.3007 (3)	0.42044 (7)	0.0460 (3)
O2	0.88967 (16)	−0.0871 (2)	0.42525 (7)	0.0474 (3)
O3	0.56818 (16)	0.1304 (3)	0.42616 (7)	0.0559 (4)
S1	0.90468 (4)	0.17803 (8)	0.40734 (2)	0.03339 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0308 (7)	0.0305 (8)	0.0315 (8)	0.0033 (6)	0.0056 (6)	−0.0026 (6)
C2	0.0435 (9)	0.0360 (9)	0.0399 (9)	−0.0037 (7)	0.0019 (7)	−0.0043 (7)
C3	0.0564 (11)	0.0548 (12)	0.0431 (10)	0.0011 (10)	−0.0087 (9)	−0.0103 (9)
C4	0.0620 (12)	0.0657 (13)	0.0339 (10)	0.0213 (11)	0.0023 (9)	0.0009 (9)
C5	0.0598 (12)	0.0549 (12)	0.0502 (12)	0.0122 (10)	0.0184 (10)	0.0169 (10)
C6	0.0421 (9)	0.0382 (9)	0.0514 (11)	−0.0007 (8)	0.0100 (8)	0.0044 (8)
C7	0.0379 (8)	0.0382 (9)	0.0295 (8)	−0.0074 (7)	0.0070 (6)	−0.0050 (7)
C8	0.0398 (8)	0.0395 (9)	0.0315 (8)	−0.0077 (7)	0.0061 (7)	−0.0077 (7)
N1	0.0354 (7)	0.0335 (7)	0.0412 (8)	−0.0081 (6)	0.0077 (6)	−0.0133 (6)
O1	0.0306 (6)	0.0568 (8)	0.0481 (7)	−0.0031 (6)	0.0013 (5)	−0.0122 (6)
O2	0.0653 (8)	0.0329 (6)	0.0403 (7)	0.0037 (6)	0.0008 (6)	0.0023 (5)
O3	0.0493 (7)	0.0586 (9)	0.0639 (9)	−0.0232 (7)	0.0212 (7)	−0.0315 (7)
S1	0.0335 (2)	0.0318 (2)	0.0329 (2)	0.00033 (16)	0.00156 (15)	−0.00477 (16)

C1—C2	1.384 (2)	C6—H6	0.9300
C1—C6	1.385 (2)	C7—O3	1.206 (2)
C1—S1	1.7600 (16)	C7—N1	1.381 (2)
C2—C3	1.386 (3)	C7—C8	1.484 (2)
C2—H2	0.9300	C8—C8i	1.310 (3)
C3—C4	1.375 (3)	C8—H8	0.9300
C3—H3	0.9300	N1—S1	1.6541 (15)
C4—C5	1.378 (3)	N1—H1N	0.840 (9)
C4—H4	0.9300	O1—S1	1.4288 (12)
C5—C6	1.386 (3)	O2—S1	1.4215 (13)
C5—H5	0.9300
C2—C1—C6	121.56 (16)	C5—C6—H6	120.6
C2—C1—S1	119.29 (13)	O3—C7—N1	122.36 (16)
C6—C1—S1	119.14 (13)	O3—C7—C8	123.95 (15)
C1—C2—C3	118.68 (18)	N1—C7—C8	113.69 (14)
C1—C2—H2	120.7	C8i—C8—C7	120.7 (2)
C3—C2—H2	120.7	C8i—C8—H8	119.6
C4—C3—C2	120.25 (19)	C7—C8—H8	119.6
C4—C3—H3	119.9	C7—N1—S1	124.88 (11)
C2—C3—H3	119.9	C7—N1—H1N	119.4 (13)
C3—C4—C5	120.70 (18)	S1—N1—H1N	115.1 (13)
C3—C4—H4	119.7	O2—S1—O1	120.19 (8)
C5—C4—H4	119.7	O2—S1—N1	109.02 (8)
C4—C5—C6	120.08 (19)	O1—S1—N1	103.61 (7)
C4—C5—H5	120.0	O2—S1—C1	108.18 (8)
C6—C5—H5	120.0	O1—S1—C1	109.22 (8)
C1—C6—C5	118.74 (18)	N1—S1—C1	105.68 (7)
C1—C6—H6	120.6
C6—C1—C2—C3	0.5 (3)	C8—C7—N1—S1	−178.46 (12)
S1—C1—C2—C3	−178.39 (14)	C7—N1—S1—O2	−49.95 (17)
C1—C2—C3—C4	−0.1 (3)	C7—N1—S1—O1	−179.05 (14)
C2—C3—C4—C5	−0.4 (3)	C7—N1—S1—C1	66.13 (16)
C3—C4—C5—C6	0.5 (3)	C2—C1—S1—O2	23.00 (16)
C2—C1—C6—C5	−0.3 (3)	C6—C1—S1—O2	−155.88 (14)
S1—C1—C6—C5	178.50 (14)	C2—C1—S1—O1	155.46 (13)
C4—C5—C6—C1	−0.1 (3)	C6—C1—S1—O1	−23.41 (16)
O3—C7—C8—C8i	1.4 (3)	C2—C1—S1—N1	−93.64 (14)
N1—C7—C8—C8i	−179.2 (2)	C6—C1—S1—N1	87.48 (14)
O3—C7—N1—S1	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.84 (1)	2.35 (2)	3.0254 (19)	138 (2)
N1—H1N···O1iii	0.84 (1)	2.45 (2)	3.1335 (19)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (1)	2.35 (2)	3.0254 (19)	138 (2)
N1—H1N⋯O1ii	0.84 (1)	2.45 (2)	3.1335 (19)	139 (2)

Symmetry codes: (i) ; (ii) .