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

In the crystal structure of the title compound, C(16)H(16)N(2)O(6)S(2), the conformation of the N-C bonds in the C-SO(2)-NH-C(O)-C segments have gauche torsions with respect to the S=O bonds, while the conformations of the N-H and C=O bonds in the amide fragments are trans to each other and the amide O atom is anti to the H atoms attached to the adjacent C atom. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C(O) torsion angle of 65.2 (2)°. The molecule lies about a centre of inversion. The dihedral angle between the benzene ring and the SO(2)-NH-C(O)-C(2) segment in the two halves of the mol-ecule is 77.4 (1)°. The structure exhibits both intra-molecular and inter-molecular hydrogen bonds. A series of N-H⋯O(S) hydrogen bonds links the mol-ecules into infinite chains.

Related literature

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

Experimental

Crystal data

C16H16N2O6S2

M = 396.43

Monoclinic,

a = 8.7800 (5) Å

b = 5.1590 (3) Å

c = 19.622 (1) Å

β = 101.255 (5)°

V = 871.71 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 299 K

0.32 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.898, T max = 0.973

3275 measured reflections

1751 independent reflections

1427 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.080

S = 1.05

1751 reflections

121 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.29 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/S1600536809053537/bq2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053537/bq2185Isup2.hkl

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

C16H16N2O6S2	F(000) = 412
Mr = 396.43	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2246 reflections
a = 8.7800 (5) Å	θ = 2.8–27.8°
b = 5.1590 (3) Å	µ = 0.34 mm−1
c = 19.622 (1) Å	T = 299 K
β = 101.255 (5)°	Rod, colourless
V = 871.71 (8) Å3	0.32 × 0.20 × 0.08 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1751 independent reflections
Radiation source: fine-focus sealed tube	1427 reflections with I > 2σ(I)
graphite	Rint = 0.015
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 = −10→9
Tmin = 0.898, Tmax = 0.973	k = −4→6
3275 measured reflections	l = −19→24

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0347P)2 + 0.3671P] where P = (Fo2 + 2Fc2)/3
1751 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.29 e Å−3
1 restraint	Δρmin = −0.29 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	0.31653 (19)	0.7383 (3)	0.31933 (9)	0.0331 (4)
C2	0.3666 (2)	0.9450 (4)	0.28431 (11)	0.0470 (5)
H2	0.4429	1.0571	0.3070	0.056*
C3	0.3010 (3)	0.9812 (5)	0.21518 (12)	0.0578 (6)
H3	0.3334	1.1185	0.1908	0.069*
C4	0.1877 (3)	0.8148 (5)	0.18224 (11)	0.0604 (6)
H4	0.1440	0.8401	0.1356	0.072*
C5	0.1385 (3)	0.6118 (5)	0.21760 (11)	0.0588 (6)
H5	0.0613	0.5013	0.1949	0.071*
C6	0.2028 (2)	0.5703 (4)	0.28671 (10)	0.0437 (5)
H6	0.1703	0.4323	0.3108	0.052*
C7	0.1467 (2)	0.8280 (3)	0.45506 (8)	0.0336 (4)
C8	0.0833 (2)	1.0277 (4)	0.49737 (9)	0.0381 (4)
H8A	0.0889	1.1968	0.4764	0.046*
H8B	0.1470	1.0324	0.5437	0.046*
O1	0.55295 (14)	0.8013 (3)	0.42093 (7)	0.0479 (4)
O2	0.38326 (17)	0.4210 (2)	0.42254 (7)	0.0486 (4)
O3	0.07266 (16)	0.6510 (3)	0.42511 (7)	0.0526 (4)
S1	0.40186 (5)	0.68656 (9)	0.40706 (2)	0.03488 (15)
N1	0.30125 (18)	0.8647 (3)	0.45214 (8)	0.0380 (4)
H1N	0.343 (2)	0.998 (3)	0.4659 (11)	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.0342 (9)	0.0330 (9)	0.0317 (8)	0.0039 (7)	0.0057 (7)	−0.0025 (7)
C2	0.0467 (11)	0.0420 (11)	0.0524 (12)	−0.0011 (9)	0.0102 (9)	0.0036 (9)
C3	0.0679 (14)	0.0579 (14)	0.0506 (12)	0.0151 (12)	0.0187 (11)	0.0188 (11)
C4	0.0701 (15)	0.0726 (16)	0.0348 (10)	0.0272 (13)	0.0015 (10)	0.0049 (11)
C5	0.0599 (13)	0.0637 (14)	0.0441 (11)	0.0025 (11)	−0.0112 (10)	−0.0104 (11)
C6	0.0460 (11)	0.0411 (11)	0.0413 (10)	−0.0029 (9)	0.0019 (8)	−0.0039 (8)
C7	0.0380 (9)	0.0341 (9)	0.0287 (8)	−0.0058 (8)	0.0061 (7)	−0.0016 (7)
C8	0.0380 (10)	0.0381 (10)	0.0383 (9)	−0.0070 (8)	0.0076 (8)	−0.0082 (8)
O1	0.0324 (7)	0.0617 (9)	0.0473 (8)	−0.0024 (6)	0.0023 (6)	−0.0128 (7)
O2	0.0680 (9)	0.0346 (7)	0.0405 (7)	0.0043 (7)	0.0036 (6)	0.0010 (6)
O3	0.0482 (8)	0.0533 (9)	0.0593 (9)	−0.0200 (7)	0.0177 (7)	−0.0259 (7)
S1	0.0359 (2)	0.0342 (3)	0.0328 (2)	0.00061 (19)	0.00258 (17)	−0.00498 (18)
N1	0.0367 (8)	0.0361 (9)	0.0413 (8)	−0.0091 (7)	0.0084 (6)	−0.0141 (7)

C1—C6	1.381 (3)	C6—H6	0.9300
C1—C2	1.386 (3)	C7—O3	1.205 (2)
C1—S1	1.7586 (17)	C7—N1	1.382 (2)
C2—C3	1.379 (3)	C7—C8	1.497 (2)
C2—H2	0.9300	C8—C8i	1.514 (3)
C3—C4	1.376 (3)	C8—H8A	0.9700
C3—H3	0.9300	C8—H8B	0.9700
C4—C5	1.372 (3)	O1—S1	1.4294 (13)
C4—H4	0.9300	O2—S1	1.4196 (14)
C5—C6	1.380 (3)	S1—N1	1.6471 (16)
C5—H5	0.9300	N1—H1N	0.800 (15)
C6—C1—C2	121.56 (17)	O3—C7—N1	121.63 (16)
C6—C1—S1	119.32 (14)	O3—C7—C8	124.62 (16)
C2—C1—S1	119.11 (14)	N1—C7—C8	113.75 (14)
C3—C2—C1	118.7 (2)	C7—C8—C8i	112.14 (18)
C3—C2—H2	120.6	C7—C8—H8A	109.2
C1—C2—H2	120.6	C8i—C8—H8A	109.2
C4—C3—C2	120.1 (2)	C7—C8—H8B	109.2
C4—C3—H3	119.9	C8i—C8—H8B	109.2
C2—C3—H3	119.9	H8A—C8—H8B	107.9
C5—C4—C3	120.6 (2)	O2—S1—O1	120.02 (9)
C5—C4—H4	119.7	O2—S1—N1	109.12 (8)
C3—C4—H4	119.7	O1—S1—N1	103.98 (8)
C4—C5—C6	120.4 (2)	O2—S1—C1	108.12 (8)
C4—C5—H5	119.8	O1—S1—C1	109.01 (8)
C6—C5—H5	119.8	N1—S1—C1	105.68 (8)
C5—C6—C1	118.57 (19)	C7—N1—S1	125.40 (12)
C5—C6—H6	120.7	C7—N1—H1N	119.9 (15)
C1—C6—H6	120.7	S1—N1—H1N	113.4 (15)
C6—C1—C2—C3	−0.3 (3)	C2—C1—S1—O2	−155.96 (15)
S1—C1—C2—C3	178.83 (16)	C6—C1—S1—O1	155.23 (15)
C1—C2—C3—C4	0.3 (3)	C2—C1—S1—O1	−23.93 (17)
C2—C3—C4—C5	0.1 (4)	C6—C1—S1—N1	−93.53 (16)
C3—C4—C5—C6	−0.5 (4)	C2—C1—S1—N1	87.30 (16)
C4—C5—C6—C1	0.4 (3)	O3—C7—N1—S1	2.2 (3)
C2—C1—C6—C5	0.0 (3)	C8—C7—N1—S1	−177.07 (13)
S1—C1—C6—C5	−179.17 (16)	O2—S1—N1—C7	−50.87 (18)
O3—C7—C8—C8i	3.9 (3)	O1—S1—N1—C7	179.93 (15)
N1—C7—C8—C8i	−176.81 (19)	C1—S1—N1—C7	65.19 (17)
C6—C1—S1—O2	23.21 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.80 (2)	2.39 (2)	3.042 (2)	139 (2)
N1—H1N···O1iii	0.80 (2)	2.46 (2)	3.093 (2)	137 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.80 (2)	2.39 (2)	3.042 (2)	139 (2)
N1—H1N⋯O1ii	0.80 (2)	2.46 (2)	3.093 (2)	137 (2)

Symmetry codes: (i) ; (ii) .