4,6-Dimethyl­benzene-1,3-disulfonamide

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.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.099
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.5U_eq(C) for methyl and U_iso(H) = 1.2U_eq(C,N) for benzene and amide H atoms. No restraints were applied to non-hydrogen atoms.

Computing details

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

	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.
	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

Crystal data

C8H12N2O4S2	F(000) = 1104
Mr = 264.32	Dx = 1.569 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14260 reflections
a = 14.4793 (2) Å	θ = 3.0–29.5°
b = 8.0520 (1) Å	µ = 0.48 mm^−1
c = 19.1935 (4) Å	T = 297 K
V = 2237.72 (6) Å^3	Block, colourless
Z = 8	0.31 × 0.18 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	1693 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ scans, and ω scans with κ offsets	θmax = 26.0°, θmin = 5.1°
Absorption correction: analytical (Clark & Reid, 1995)	h = −17→17
Tmin = 0.868, Tmax = 0.942	k = −9→9
33751 measured reflections	l = −23→23
2183 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 0.0106P] where P = (Fo^2 + 2Fc^2)/3
2183 reflections	(Δ/σ)max = 0.003
159 parameters	Δρmax = 0.27 e Å^−3
4 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.23215 (12)	0.4353 (2)	0.44644 (10)	0.0325 (4)
C2	0.32502 (12)	0.4435 (2)	0.42955 (10)	0.0320 (4)
H2	0.3683	0.4692	0.4637	0.038*
C3	0.35327 (13)	0.4134 (2)	0.36175 (10)	0.0337 (4)
C4	0.28991 (14)	0.3696 (2)	0.30997 (11)	0.0421 (5)
C5	0.19745 (14)	0.3675 (3)	0.32909 (12)	0.0470 (5)
H5	0.1541	0.342	0.295	0.056*
C6	0.16569 (12)	0.4010 (2)	0.39580 (11)	0.0376 (5)
C7	0.31541 (17)	0.3244 (3)	0.23612 (12)	0.0656 (7)
H7A	0.3575	0.2323	0.2366	0.098*
H7B	0.3443	0.4179	0.214	0.098*
H7C	0.2607	0.2943	0.2109	0.098*
C8	0.06333 (14)	0.3980 (3)	0.41059 (13)	0.0535 (6)
H8A	0.0466	0.4947	0.437	0.08*
H8B	0.0484	0.3001	0.4368	0.08*
H8C	0.0299	0.3972	0.3674	0.08*
N1	0.28772 (11)	0.4730 (2)	0.58211 (9)	0.0397 (4)
H1A	0.3209 (14)	0.556 (2)	0.5760 (12)	0.048*
H1B	0.3178 (13)	0.387 (2)	0.5829 (12)	0.048*
N2	0.51984 (14)	0.2642 (3)	0.33063 (11)	0.0569 (5)
H2A	0.5078 (17)	0.213 (3)	0.2941 (11)	0.068*
H2B	0.5402 (18)	0.217 (3)	0.3656 (11)	0.068*
O1	0.14493 (9)	0.32605 (15)	0.55488 (7)	0.0451 (4)
O2	0.15455 (9)	0.62787 (16)	0.53936 (7)	0.0440 (4)
O3	0.51437 (10)	0.50240 (18)	0.40649 (8)	0.0507 (4)
O4	0.48035 (12)	0.5335 (2)	0.28186 (9)	0.0664 (5)
S1	0.19779 (3)	0.46871 (5)	0.53417 (2)	0.03266 (18)
S2	0.47313 (3)	0.43915 (6)	0.34460 (3)	0.03907 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0319 (10)	0.0292 (10)	0.0362 (11)	−0.0005 (7)	0.0009 (8)	0.0020 (8)
C2	0.0296 (10)	0.0330 (9)	0.0335 (11)	−0.0026 (7)	−0.0023 (8)	0.0013 (8)
C3	0.0324 (10)	0.0358 (10)	0.0329 (11)	0.0002 (8)	0.0003 (8)	0.0036 (8)
C4	0.0436 (11)	0.0496 (11)	0.0332 (11)	0.0054 (9)	−0.0055 (9)	0.0021 (9)
C5	0.0418 (12)	0.0534 (12)	0.0456 (13)	−0.0028 (9)	−0.0150 (10)	−0.0040 (10)
C6	0.0307 (10)	0.0364 (10)	0.0457 (13)	−0.0004 (8)	−0.0048 (9)	−0.0003 (9)
C7	0.0620 (15)	0.0968 (19)	0.0379 (13)	0.0059 (14)	−0.0054 (11)	−0.0141 (13)
C8	0.0317 (11)	0.0664 (14)	0.0623 (15)	−0.0024 (10)	−0.0058 (10)	−0.0029 (12)
N1	0.0381 (10)	0.0435 (10)	0.0376 (10)	−0.0002 (7)	0.0025 (8)	−0.0004 (8)
N2	0.0646 (13)	0.0638 (13)	0.0422 (12)	0.0225 (10)	−0.0098 (10)	−0.0131 (10)
O1	0.0397 (8)	0.0394 (8)	0.0562 (9)	−0.0069 (6)	0.0116 (7)	0.0065 (6)
O2	0.0384 (8)	0.0340 (7)	0.0595 (9)	0.0050 (6)	0.0051 (6)	−0.0057 (6)
O3	0.0345 (8)	0.0660 (9)	0.0516 (10)	−0.0064 (7)	0.0038 (7)	−0.0163 (8)
O4	0.0598 (10)	0.0812 (12)	0.0581 (11)	−0.0013 (8)	0.0130 (8)	0.0347 (9)
S1	0.0287 (3)	0.0316 (3)	0.0376 (3)	−0.00196 (18)	0.00553 (19)	−0.00020 (19)
S2	0.0347 (3)	0.0463 (3)	0.0362 (3)	0.0016 (2)	0.0054 (2)	0.0042 (2)

Geometric parameters (Å, º)

C1—C2	1.385 (2)	C7—H7C	0.96
C1—C6	1.395 (3)	C8—H8A	0.96
C1—S1	1.776 (2)	C8—H8B	0.96
C2—C3	1.386 (3)	C8—H8C	0.96
C2—H2	0.93	N1—S1	1.5949 (18)
C3—C4	1.398 (3)	N1—H1A	0.829 (15)
C3—S2	1.7785 (19)	N1—H1B	0.821 (15)
C4—C5	1.388 (3)	N2—S2	1.586 (2)
C4—C7	1.509 (3)	N2—H2A	0.830 (17)
C5—C6	1.387 (3)	N2—H2B	0.825 (17)
C5—H5	0.93	O1—S1	1.4364 (13)
C6—C8	1.509 (3)	O2—S1	1.4297 (13)
C7—H7A	0.96	O3—S2	1.4236 (15)
C7—H7B	0.96	O4—S2	1.4275 (16)
C2—C1—C6	121.07 (18)	C6—C8—H8A	109.5
C2—C1—S1	119.12 (15)	C6—C8—H8B	109.5
C6—C1—S1	119.81 (14)	H8A—C8—H8B	109.5
C1—C2—C3	119.88 (18)	C6—C8—H8C	109.5
C1—C2—H2	120.1	H8A—C8—H8C	109.5
C3—C2—H2	120.1	H8B—C8—H8C	109.5
C2—C3—C4	121.20 (18)	S1—N1—H1A	114.1 (16)
C2—C3—S2	116.20 (14)	S1—N1—H1B	115.1 (16)
C4—C3—S2	122.58 (15)	H1A—N1—H1B	112 (2)
C5—C4—C3	116.63 (19)	S2—N2—H2A	119.5 (18)
C5—C4—C7	118.76 (19)	S2—N2—H2B	114.9 (19)
C3—C4—C7	124.61 (19)	H2A—N2—H2B	122 (3)
C6—C5—C4	124.15 (18)	O2—S1—O1	117.66 (8)
C6—C5—H5	117.9	O2—S1—N1	107.33 (9)
C4—C5—H5	117.9	O1—S1—N1	107.02 (9)
C5—C6—C1	116.93 (17)	O2—S1—C1	108.94 (8)
C5—C6—C8	119.74 (18)	O1—S1—C1	106.88 (8)
C1—C6—C8	123.33 (18)	N1—S1—C1	108.76 (9)
C4—C7—H7A	109.5	O3—S2—O4	118.87 (10)
C4—C7—H7B	109.5	O3—S2—N2	106.27 (10)
H7A—C7—H7B	109.5	O4—S2—N2	107.38 (11)
C4—C7—H7C	109.5	O3—S2—C3	107.26 (9)
H7A—C7—H7C	109.5	O4—S2—C3	106.83 (9)
H7B—C7—H7C	109.5	N2—S2—C3	110.12 (10)
C6—C1—C2—C3	−1.6 (3)	C2—C1—C6—C8	−177.22 (18)
S1—C1—C2—C3	178.28 (12)	S1—C1—C6—C8	2.9 (3)
C1—C2—C3—C4	−1.9 (3)	C2—C1—S1—O2	106.92 (14)
C1—C2—C3—S2	176.44 (12)	C6—C1—S1—O2	−73.16 (15)
C2—C3—C4—C5	3.6 (3)	C2—C1—S1—O1	−124.98 (14)
S2—C3—C4—C5	−174.66 (15)	C6—C1—S1—O1	54.94 (16)
C2—C3—C4—C7	−176.00 (19)	C2—C1—S1—N1	−9.76 (16)
S2—C3—C4—C7	5.7 (3)	C6—C1—S1—N1	170.16 (15)
C3—C4—C5—C6	−1.9 (3)	C2—C3—S2—O3	−5.20 (16)
C7—C4—C5—C6	177.7 (2)	C4—C3—S2—O3	173.16 (16)
C4—C5—C6—C1	−1.4 (3)	C2—C3—S2—O4	−133.67 (15)
C4—C5—C6—C8	179.01 (19)	C4—C3—S2—O4	44.69 (19)
C2—C1—C6—C5	3.2 (3)	C2—C3—S2—N2	110.03 (16)
S1—C1—C6—C5	−176.68 (14)	C4—C3—S2—N2	−71.62 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.83 (2)	2.27 (2)	3.050 (2)	157 (2)
N1—H1B···O2^ii	0.82 (2)	2.28 (2)	3.016 (2)	149 (2)
N2—H2A···O4^iii	0.83 (2)	2.06 (2)	2.848 (3)	158 (2)
N2—H2B···O1^iv	0.83 (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.