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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o187.
Published online 2009 December 24. doi:  10.1107/S1600536809053811
PMCID: PMC2980026

N,N′-Bis(phenyl­sulfon­yl)maleamide

Abstract

Mol­ecules of the title compound, C16H14N2O6S2, show crystallographic inversion symmetry: there is one half-mol­ecule in the asymmetric unit. The structure exhibits both intramolecular and inter­molecular 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 [triangle], 2010 [triangle]), Suchetan et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o187-scheme1.jpg

Experimental

Crystal data

  • C16H14N2O6S2
  • M r = 394.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o187-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

PA. thanks the Council of Scientific and Industrial Research, India, for the award of a research fellowship.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of a study of the effect of ring and the side chain substituents on the solid state structures of N-aromatic sulfonamides (Gowda et al., 2009, 2010; Suchetan et al., 2009), in the present work, the structure of N,N-(Diphenylsulfonyl)maleamide (I) has been determined (Fig. 1).

The conformations of N—H and C=O bonds in the amide fragments are trans to each other and the amide O atoms are anti to the H atoms attached to the adjacent C atoms, similar to that observed in N,N-(diphenylsulfonyl)succinamide (II)(Gowda et al., 2010). The molecule is bent at the S atoms with the C—SO2—NH—C(O) torsion angle of 66.1 (2)° in (II), compared to the value of 65.2 (2)°. The dihedral angle between the benzene ring and the SO2—NH—C(O)—C segment in the two halves of the molecule is 76.4 (1)°, compared to the corresponding angle of 77.4 (1)° in (II). The structure exhibits both the intramolecular and intermolecular hydrogen bonds. The series of N—H···O(S) hydrogen bonds (Table 1) link the molecules into column like infinite chains parallel to a-axis (Fig. 2).

Experimental

N,N-(Diphenylsulfonyl)maleamide was prepared by refluxing a mixture of maleic anhydride (0.01 mol), benzenesulfonamide (0.02 mol) and POCl3 for 3hr on a water bath. The reaction mixture was allowed to cool. Ether was added to it. The solid product obtained was filtered off, washed thoroughly with ether and hot alcohol and recrystallized to the constant melting point of 255–259° C

Rod like single crystals used in the X-ray diffraction studies were obtained from a solution of the compound in DMF.

Refinement

The H atom of the NH group was located in difference map and later restrained to N—H = 0.86 (1) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the Ueq of the parent atom.

Figures

Fig. 1.
Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines.

Crystal data

C16H14N2O6S2F(000) = 408
Mr = 394.41Dx = 1.535 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1915 reflections
a = 8.582 (1) Åθ = 2.8–27.7°
b = 5.1464 (6) ŵ = 0.35 mm1
c = 19.691 (4) ÅT = 299 K
β = 101.17 (2)°Rod, colourless
V = 853.2 (2) Å30.48 × 0.28 × 0.22 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector1720 independent reflections
Radiation source: fine-focus sealed tube1500 reflections with I > 2σ(I)
graphiteRint = 0.009
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −9→10
Tmin = 0.850, Tmax = 0.927k = −6→6
3236 measured reflectionsl = −24→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0402P)2 + 0.3647P] where P = (Fo2 + 2Fc2)/3
1720 reflections(Δ/σ)max = 0.004
121 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = −0.32 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.81684 (18)0.2173 (3)0.31947 (8)0.0310 (3)
C20.7033 (2)0.0409 (3)0.28846 (9)0.0406 (4)
H20.6715−0.09470.31390.049*
C30.6381 (2)0.0704 (4)0.21881 (10)0.0539 (5)
H30.5618−0.04650.19710.065*
C40.6857 (3)0.2717 (4)0.18171 (10)0.0548 (5)
H40.64170.28940.13490.066*
C50.7979 (3)0.4475 (4)0.21310 (11)0.0539 (5)
H50.82870.58370.18760.065*
C60.8651 (2)0.4217 (4)0.28269 (10)0.0438 (4)
H60.94100.53930.30430.053*
C70.64152 (19)0.3130 (3)0.45450 (8)0.0351 (4)
C80.57352 (19)0.5096 (3)0.49559 (8)0.0370 (4)
H80.63600.64810.51530.044*
N10.79828 (16)0.3588 (3)0.45084 (8)0.0367 (3)
H1N0.842 (2)0.498 (3)0.4667 (10)0.044*
O11.05692 (13)0.3007 (3)0.42044 (7)0.0460 (3)
O20.88967 (16)−0.0871 (2)0.42525 (7)0.0474 (3)
O30.56818 (16)0.1304 (3)0.42616 (7)0.0559 (4)
S10.90468 (4)0.17803 (8)0.40734 (2)0.03339 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0308 (7)0.0305 (8)0.0315 (8)0.0033 (6)0.0056 (6)−0.0026 (6)
C20.0435 (9)0.0360 (9)0.0399 (9)−0.0037 (7)0.0019 (7)−0.0043 (7)
C30.0564 (11)0.0548 (12)0.0431 (10)0.0011 (10)−0.0087 (9)−0.0103 (9)
C40.0620 (12)0.0657 (13)0.0339 (10)0.0213 (11)0.0023 (9)0.0009 (9)
C50.0598 (12)0.0549 (12)0.0502 (12)0.0122 (10)0.0184 (10)0.0169 (10)
C60.0421 (9)0.0382 (9)0.0514 (11)−0.0007 (8)0.0100 (8)0.0044 (8)
C70.0379 (8)0.0382 (9)0.0295 (8)−0.0074 (7)0.0070 (6)−0.0050 (7)
C80.0398 (8)0.0395 (9)0.0315 (8)−0.0077 (7)0.0061 (7)−0.0077 (7)
N10.0354 (7)0.0335 (7)0.0412 (8)−0.0081 (6)0.0077 (6)−0.0133 (6)
O10.0306 (6)0.0568 (8)0.0481 (7)−0.0031 (6)0.0013 (5)−0.0122 (6)
O20.0653 (8)0.0329 (6)0.0403 (7)0.0037 (6)0.0008 (6)0.0023 (5)
O30.0493 (7)0.0586 (9)0.0639 (9)−0.0232 (7)0.0212 (7)−0.0315 (7)
S10.0335 (2)0.0318 (2)0.0329 (2)0.00033 (16)0.00156 (15)−0.00477 (16)

Geometric parameters (Å, °)

C1—C21.384 (2)C6—H60.9300
C1—C61.385 (2)C7—O31.206 (2)
C1—S11.7600 (16)C7—N11.381 (2)
C2—C31.386 (3)C7—C81.484 (2)
C2—H20.9300C8—C8i1.310 (3)
C3—C41.375 (3)C8—H80.9300
C3—H30.9300N1—S11.6541 (15)
C4—C51.378 (3)N1—H1N0.840 (9)
C4—H40.9300O1—S11.4288 (12)
C5—C61.386 (3)O2—S11.4215 (13)
C5—H50.9300
C2—C1—C6121.56 (16)C5—C6—H6120.6
C2—C1—S1119.29 (13)O3—C7—N1122.36 (16)
C6—C1—S1119.14 (13)O3—C7—C8123.95 (15)
C1—C2—C3118.68 (18)N1—C7—C8113.69 (14)
C1—C2—H2120.7C8i—C8—C7120.7 (2)
C3—C2—H2120.7C8i—C8—H8119.6
C4—C3—C2120.25 (19)C7—C8—H8119.6
C4—C3—H3119.9C7—N1—S1124.88 (11)
C2—C3—H3119.9C7—N1—H1N119.4 (13)
C3—C4—C5120.70 (18)S1—N1—H1N115.1 (13)
C3—C4—H4119.7O2—S1—O1120.19 (8)
C5—C4—H4119.7O2—S1—N1109.02 (8)
C4—C5—C6120.08 (19)O1—S1—N1103.61 (7)
C4—C5—H5120.0O2—S1—C1108.18 (8)
C6—C5—H5120.0O1—S1—C1109.22 (8)
C1—C6—C5118.74 (18)N1—S1—C1105.68 (7)
C1—C6—H6120.6
C6—C1—C2—C30.5 (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—C166.13 (16)
C3—C4—C5—C60.5 (3)C2—C1—S1—O223.00 (16)
C2—C1—C6—C5−0.3 (3)C6—C1—S1—O2−155.88 (14)
S1—C1—C6—C5178.50 (14)C2—C1—S1—O1155.46 (13)
C4—C5—C6—C1−0.1 (3)C6—C1—S1—O1−23.41 (16)
O3—C7—C8—C8i1.4 (3)C2—C1—S1—N1−93.64 (14)
N1—C7—C8—C8i−179.2 (2)C6—C1—S1—N187.48 (14)
O3—C7—N1—S11.0 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O2ii0.84 (1)2.35 (2)3.0254 (19)138 (2)
N1—H1N···O1iii0.84 (1)2.45 (2)3.1335 (19)139 (2)

Symmetry codes: (ii) x, y+1, z; (iii) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5141).

References

  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o181. [PMC free article] [PubMed]
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography