N-(2,3-Dimethyl­phen­yl)-4-fluoro-N-[(4-fluoro­phen­yl)sulfon­yl]benzene­sulfonamide

Shumaila Younas Mughal; Islam Ullah Khan; William T A Harrison; Muneeb Hayat Khan; Muhammad Nawaz Tahir

doi:10.1107/S1600536812039402

. 2012 Sep 22;68(Pt 10):o2973. doi: 10.1107/S1600536812039402

N-(2,3-Dimethylphenyl)-4-fluoro-N-[(4-fluorophenyl)sulfonyl]benzenesulfonamide

Shumaila Younas Mughal ^a, Islam Ullah Khan ^a,^*, William T A Harrison ^b, Muneeb Hayat Khan ^c, Muhammad Nawaz Tahir ^d

PMCID: PMC3470340 PMID: 23125753

Abstract

In the title compound, C₂₀H₁₇F₂NO₄S₂, the dihedral angles between the o-xylene ring and the fluorobenzene rings are 31.7 (1) and 32.8 (1)°, and the dihedral angle between the fluorobenzene rings is 50.9 (1)°. The C—N—S—C torsion angles are 76.7 (2) and 101.8 (2)°. In the crystal, molecules are connected by C—H⋯O interactions into sheets in the ab plane.

Related literature

For related crystal structures, see: Hanson & Hitchcock (2004 ▶); Low et al. (2006 ▶); Mughal et al. (2012 ▶).

Experimental

Crystal data

C₂₀H₁₇F₂NO₄S₂
M _r = 437.47
Orthorhombic,
a = 9.9493 (5) Å
b = 14.7107 (8) Å
c = 26.6871 (17) Å
V = 3906.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.916, T _max = 0.930
31734 measured reflections
4352 independent reflections
2943 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.133
S = 1.02
4352 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039402/ld2072sup1.cif

e-68-o2973-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039402/ld2072Isup2.hkl

e-68-o2973-Isup2.hkl^{(213.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039402/ld2072Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2ⁱ	0.96	2.57	3.517 (5)	170
C19—H19⋯O1ⁱⁱ	0.93	2.39	3.260 (4)	157

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for providing a grant under a project strengthening the Materials Chemistry Laboratory at GC University, Lahore.

supplementary crystallographic information

Comment

Rather than the intended 4-fluoro-N-(2,3-dimethylphenyl)benzenesulfonamide, the title `double' sulfonamide (I), (Fig. 1) was unexpectedly obtained in our ongoing studies (Mughal et al., 2012). The related structures of 4-chloroaniline-N,N-ditoluene-p-sulfonamide, (II) (Hanson & Hitchcock, 2004) and 4-iodo-N,N-bis-(2-nitrophenylsulfonyl)aniline, (III) (Low et al., 2006) have been described previously.

The molecule of (I) cannot possess any local symmetry due to the two methyl groups of the xylene ring. Without them, the rest of the moleucle possesses approximate local twofold symmetry about the C1—N1 axis.

The sulfonamide C—N—S—C torsion angles in (I) [76.7 (2) and 101.8 (2)°] compare well to the corresponding value of 80.2° reported in (II), where the molecule posesses a crystallographic twofold symmetry. The respective values in (III) are 98.9 (2) and 94.3 (2)°. The bond-angle sum for the N atom in (I) of 359.7° implies sp² hybridization for the N atom.

In the crystal of (I), there are weak C—H···O hydrogen bonds between the molecules (Table 1). The C8 bond results in translational chains along [100] and the C19 bond results in helices along [010]. Together these generate (001) sheets.

Experimental

0.10 g of 2,3-dimethyl aniline was dissolved in 15 ml dichloromethane, and 0.16 g of 4-fluoro benzene sulfonyl chloride was added. The mixture was stirred at room temperature overnight and its pH was maintained at 8–9 with triethylamine. On completion of the reaction (after TLC), 1M HCl solution was added, the organic fraction was separated, and the solvent was evaporated at room temperature to generate dark brown crystals in 94% yield. Yellow blocks were recrystallized from ethanol solution.