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Acta Cryst. (2007). E63, o3361    [ doi:10.1107/S1600536807031297 ]

4,6-Dimethylbenzene-1,3-disulfonamide

B. T. Gowda, K. S. Babitha, M. Tokarcík, J. Kozísek and H. Fuess

Abstract top

The structure of the title compound, C8H12N2O4S2, resembles those of other arylsulfonamides. The molecules in the title compound are packed into an infinite three-dimensional molecular network stabilized by hydrogen bonds.

Comment top

Arylsulfonamides and their N-halo compounds are of interest in synthetic, mechanistic, analytical and biological chemistry. In the present work, the structure of 4,6-dimethyl-benzene-1,3-disulfonamide has been determined to explore the effect of substituents on the solid state structures of sulfonamides and N-halo-arylsulfonamides (Gowda et al., 2007a, b, c). The structure of the title compound (Fig. 1) resembles those of other arylsulfonamides (Gowda et al., 2007a, b, c, d; Kumar et al., 1992). It crystallizes in the orthorhombic space group Pbca, in contrast to the monoclinic space group P21/c observed for both 3,4-dimethylbenzenesulfonamide (Gowda et al., 2007b) and 3,4-dichlorobenzenesulfonamide (Gowda et al., 2007c), and the triclinic space group P1 with 2-methyl-4-chloro-benzenesulfonamide (Gowda et al., 2007d), and monoclinic space group Pc with the parent benzenesulfonamide (Gowda et al., 2007a) and 4-methyl-benzenesulfonamide (Kumar et al., 1992). The bond parameters are similar to those in other arylsulfonamides. The molecules in the title compound are packed into infinite 3-D molecular network stabilized by hydrogen bonding (Table 1 and Fig. 2).

Related literature top

For related literature, see: Gowda et al. (2002, 2007a,b,c,d); Kumar et al. (1992).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2002). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution.

Refinement top

H atoms of methyl groups and benzene ring were placed geometrically and refined using a riding model with C—H distances 0.96Å (methyl) and 0.93Å (ring). H atoms of amide groups were visible in the difference map and have been subsequently treated as riding with N—H bond length restrained to 0.83 (2) Å. All H atoms have isotropic thermal displacements with Uiso(H) = 1.5Ueq(C) for methyl and Uiso(H) = 1.2Ueq(C,N) for benzene and amide H atoms. No restraints were applied to non-hydrogen atoms.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Crystal structure of the title compound stabilized by hydrogen bonds N1—H1A···O1(i), N1—H1B···O2(ii), N2—H2A···O4(iii), N2—H2B···O1(iv). Symmetry codes: (i) −x + 1/2,y + 1/2,z; (ii) −x + 1/2,y − 1/2,z; (iii) −x + 1,y − 1/2,-z + 1/2; (iv) x + 1/2,-y + 1/2,-z + 1. H atoms not involved in hydrogen bonds have been omitted.
4,6-Dimethylbenzene-1,3-disulfonamide top
Crystal data top
C8H12N2O4S2F(000) = 1104
Mr = 264.32Dx = 1.569 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 14260 reflections
a = 14.4793 (2) Åθ = 3.0–29.5°
b = 8.0520 (1) ŵ = 0.48 mm−1
c = 19.1935 (4) ÅT = 297 K
V = 2237.72 (6) Å3Block, colourless
Z = 80.31 × 0.18 × 0.14 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer		1693 reflections with I > 2σ(I)
graphiteRint = 0.034
φ scans, and ω scans with κ offsetsθmax = 26.0°, θmin = 5.1°
Absorption correction: analytical
(Clark & Reid, 1995)		h = −17→17
Tmin = 0.868, Tmax = 0.942k = −9→9
33751 measured reflectionsl = −23→23
2183 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0661P)2 + 0.0106P]
where P = (Fo2 + 2Fc2)/3
2183 reflections(Δ/σ)max = 0.003
159 parametersΔρmax = 0.27 e Å−3
4 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C8H12N2O4S2V = 2237.72 (6) Å3
Mr = 264.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.4793 (2) ŵ = 0.48 mm−1
b = 8.0520 (1) ÅT = 297 K
c = 19.1935 (4) Å0.31 × 0.18 × 0.14 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer		1693 reflections with I > 2σ(I)
Absorption correction: analytical
(Clark & Reid, 1995)		Rint = 0.034
Tmin = 0.868, Tmax = 0.942θmax = 26.0°
33751 measured reflectionsStandard reflections: 0
2183 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099Δρmax = 0.27 e Å−3
S = 1.07Δρmin = −0.28 e Å−3
2183 reflectionsAbsolute structure: ?
159 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
Special details top

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
xyzUiso*/Ueq
C10.23215 (12)0.4353 (2)0.44644 (10)0.0325 (4)
C20.32502 (12)0.4435 (2)0.42955 (10)0.0320 (4)
H20.36830.46920.46370.038*
C30.35327 (13)0.4134 (2)0.36175 (10)0.0337 (4)
C40.28991 (14)0.3696 (2)0.30997 (11)0.0421 (5)
C50.19745 (14)0.3675 (3)0.32909 (12)0.0470 (5)
H50.15410.3420.2950.056*
C60.16569 (12)0.4010 (2)0.39580 (11)0.0376 (5)
C70.31541 (17)0.3244 (3)0.23612 (12)0.0656 (7)
H7A0.35750.23230.23660.098*
H7B0.34430.41790.2140.098*
H7C0.26070.29430.21090.098*
C80.06333 (14)0.3980 (3)0.41059 (13)0.0535 (6)
H8A0.04660.49470.4370.08*
H8B0.04840.30010.43680.08*
H8C0.02990.39720.36740.08*
N10.28772 (11)0.4730 (2)0.58211 (9)0.0397 (4)
H1A0.3209 (14)0.556 (2)0.5760 (12)0.048*
H1B0.3178 (13)0.387 (2)0.5829 (12)0.048*
N20.51984 (14)0.2642 (3)0.33063 (11)0.0569 (5)
H2A0.5078 (17)0.213 (3)0.2941 (11)0.068*
H2B0.5402 (18)0.217 (3)0.3656 (11)0.068*
O10.14493 (9)0.32605 (15)0.55488 (7)0.0451 (4)
O20.15455 (9)0.62787 (16)0.53936 (7)0.0440 (4)
O30.51437 (10)0.50240 (18)0.40649 (8)0.0507 (4)
O40.48035 (12)0.5335 (2)0.28186 (9)0.0664 (5)
S10.19779 (3)0.46871 (5)0.53417 (2)0.03266 (18)
S20.47313 (3)0.43915 (6)0.34460 (3)0.03907 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0319 (10)0.0292 (10)0.0362 (11)−0.0005 (7)0.0009 (8)0.0020 (8)
C20.0296 (10)0.0330 (9)0.0335 (11)−0.0026 (7)−0.0023 (8)0.0013 (8)
C30.0324 (10)0.0358 (10)0.0329 (11)0.0002 (8)0.0003 (8)0.0036 (8)
C40.0436 (11)0.0496 (11)0.0332 (11)0.0054 (9)−0.0055 (9)0.0021 (9)
C50.0418 (12)0.0534 (12)0.0456 (13)−0.0028 (9)−0.0150 (10)−0.0040 (10)
C60.0307 (10)0.0364 (10)0.0457 (13)−0.0004 (8)−0.0048 (9)−0.0003 (9)
C70.0620 (15)0.0968 (19)0.0379 (13)0.0059 (14)−0.0054 (11)−0.0141 (13)
C80.0317 (11)0.0664 (14)0.0623 (15)−0.0024 (10)−0.0058 (10)−0.0029 (12)
N10.0381 (10)0.0435 (10)0.0376 (10)−0.0002 (7)0.0025 (8)−0.0004 (8)
N20.0646 (13)0.0638 (13)0.0422 (12)0.0225 (10)−0.0098 (10)−0.0131 (10)
O10.0397 (8)0.0394 (8)0.0562 (9)−0.0069 (6)0.0116 (7)0.0065 (6)
O20.0384 (8)0.0340 (7)0.0595 (9)0.0050 (6)0.0051 (6)−0.0057 (6)
O30.0345 (8)0.0660 (9)0.0516 (10)−0.0064 (7)0.0038 (7)−0.0163 (8)
O40.0598 (10)0.0812 (12)0.0581 (11)−0.0013 (8)0.0130 (8)0.0347 (9)
S10.0287 (3)0.0316 (3)0.0376 (3)−0.00196 (18)0.00553 (19)−0.00020 (19)
S20.0347 (3)0.0463 (3)0.0362 (3)0.0016 (2)0.0054 (2)0.0042 (2)
Geometric parameters (Å, °) top
C1—C21.385 (2)C7—H7C0.96
C1—C61.395 (3)C8—H8A0.96
C1—S11.776 (2)C8—H8B0.96
C2—C31.386 (3)C8—H8C0.96
C2—H20.93N1—S11.5949 (18)
C3—C41.398 (3)N1—H1A0.829 (15)
C3—S21.7785 (19)N1—H1B0.821 (15)
C4—C51.388 (3)N2—S21.586 (2)
C4—C71.509 (3)N2—H2A0.830 (17)
C5—C61.387 (3)N2—H2B0.825 (17)
C5—H50.93O1—S11.4364 (13)
C6—C81.509 (3)O2—S11.4297 (13)
C7—H7A0.96O3—S21.4236 (15)
C7—H7B0.96O4—S21.4275 (16)
C2—C1—C6121.07 (18)C6—C8—H8A109.5
C2—C1—S1119.12 (15)C6—C8—H8B109.5
C6—C1—S1119.81 (14)H8A—C8—H8B109.5
C1—C2—C3119.88 (18)C6—C8—H8C109.5
C1—C2—H2120.1H8A—C8—H8C109.5
C3—C2—H2120.1H8B—C8—H8C109.5
C2—C3—C4121.20 (18)S1—N1—H1A114.1 (16)
C2—C3—S2116.20 (14)S1—N1—H1B115.1 (16)
C4—C3—S2122.58 (15)H1A—N1—H1B112 (2)
C5—C4—C3116.63 (19)S2—N2—H2A119.5 (18)
C5—C4—C7118.76 (19)S2—N2—H2B114.9 (19)
C3—C4—C7124.61 (19)H2A—N2—H2B122 (3)
C6—C5—C4124.15 (18)O2—S1—O1117.66 (8)
C6—C5—H5117.9O2—S1—N1107.33 (9)
C4—C5—H5117.9O1—S1—N1107.02 (9)
C5—C6—C1116.93 (17)O2—S1—C1108.94 (8)
C5—C6—C8119.74 (18)O1—S1—C1106.88 (8)
C1—C6—C8123.33 (18)N1—S1—C1108.76 (9)
C4—C7—H7A109.5O3—S2—O4118.87 (10)
C4—C7—H7B109.5O3—S2—N2106.27 (10)
H7A—C7—H7B109.5O4—S2—N2107.38 (11)
C4—C7—H7C109.5O3—S2—C3107.26 (9)
H7A—C7—H7C109.5O4—S2—C3106.83 (9)
H7B—C7—H7C109.5N2—S2—C3110.12 (10)
C6—C1—C2—C3−1.6 (3)C2—C1—C6—C8−177.22 (18)
S1—C1—C2—C3178.28 (12)S1—C1—C6—C82.9 (3)
C1—C2—C3—C4−1.9 (3)C2—C1—S1—O2106.92 (14)
C1—C2—C3—S2176.44 (12)C6—C1—S1—O2−73.16 (15)
C2—C3—C4—C53.6 (3)C2—C1—S1—O1−124.98 (14)
S2—C3—C4—C5−174.66 (15)C6—C1—S1—O154.94 (16)
C2—C3—C4—C7−176.00 (19)C2—C1—S1—N1−9.76 (16)
S2—C3—C4—C75.7 (3)C6—C1—S1—N1170.16 (15)
C3—C4—C5—C6−1.9 (3)C2—C3—S2—O3−5.20 (16)
C7—C4—C5—C6177.7 (2)C4—C3—S2—O3173.16 (16)
C4—C5—C6—C1−1.4 (3)C2—C3—S2—O4−133.67 (15)
C4—C5—C6—C8179.01 (19)C4—C3—S2—O444.69 (19)
C2—C1—C6—C53.2 (3)C2—C3—S2—N2110.03 (16)
S1—C1—C6—C5−176.68 (14)C4—C3—S2—N2−71.62 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.83 (2)2.27 (2)3.050 (2)157 (2)
N1—H1B···O2ii0.82 (2)2.28 (2)3.016 (2)149 (2)
N2—H2A···O4iii0.83 (2)2.06 (2)2.848 (3)158 (2)
N2—H2B···O1iv0.83 (2)2.18 (2)2.939 (2)153 (2)
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.83 (2)2.27 (2)3.050 (2)157 (2)
N1—H1B···O2ii0.82 (2)2.28 (2)3.016 (2)149 (2)
N2—H2A···O4iii0.83 (2)2.06 (2)2.848 (3)158 (2)
N2—H2B···O1iv0.83 (2)2.18 (2)2.939 (2)153 (2)
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.
Acknowledgements top

BTG gratefully thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship. MT and JK thank the Grant Agency of the Slovak Republic (grant No. 1/2449/05).

references
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