N,N′-Bis(phenyl­sulfon­yl)maleamide

Gowda, B.T.; Foro, S.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536809053811

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o187

doi:10.1107/S1600536809053811

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ADDENDA AND ERRATA

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N,N′-Bis(phenylsulfonyl)maleamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 13 December 2009; accepted 14 December 2009; online 24 December 2009)

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 , 2010 ), Suchetan et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₆S₂
M_r = 394.41
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.07
1720 reflections
121 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) x, y+1, z; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053811/bt5141sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	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.

N,N'-Bis(phenylsulfonyl)maleamide top

Crystal data top

C₁₆H₁₄N₂O₆S₂	F(000) = 408
M_r = 394.41	D_x = 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

Data collection top

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 monochromator	R_int = 0.009
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→10
T_min = 0.850, T_max = 0.927	k = −6→6
3236 measured reflections	l = −24→14

Refinement top

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(F_o²) + (0.0402P)² + 0.3647P] where P = (F_o² + 2F_c²)/3
1720 reflections	(Δ/σ)_max = 0.004
121 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₆S₂	V = 853.2 (2) Å³
M_r = 394.41	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.582 (1) Å	µ = 0.35 mm⁻¹
b = 5.1464 (6) Å	T = 299 K
c = 19.691 (4) Å	0.48 × 0.28 × 0.22 mm
β = 101.17 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1720 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1500 reflections with I > 2σ(I)
T_min = 0.850, T_max = 0.927	R_int = 0.009
3236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.25 e Å⁻³
1720 reflections	Δρ_min = −0.32 e Å⁻³
121 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₆S₂
M_r	394.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	8.582 (1), 5.1464 (6), 19.691 (4)
β (°)	101.17 (2)
V (Å³)	853.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.48 × 0.28 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.850, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	3236, 1720, 1500
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.07
No. of reflections	1720
No. of parameters	121
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.840 (9)	2.350 (15)	3.0254 (19)	137.8 (17)
N1—H1N···O1ⁱⁱ	0.840 (9)	2.453 (15)	3.1335 (19)	138.7 (17)

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

Acknowledgements

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

References

Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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