N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-fluoro­benzene­sulfonamide

Shumaila Younas Mughal; Islam Ullah Khan; William T A Harrison; Muneeb Hayat Khan; Muhammad Nadeem Arshad

doi:10.1107/S1600536812030863

. 2012 Jul 10;68(Pt 8):o2433. doi: 10.1107/S1600536812030863

N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-fluorobenzenesulfonamide

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

PMCID: PMC3414348 PMID: 22904881

Abstract

In the title compound, C₁₄H₁₂FNO₄S, the dihedral angle between the aromatic rings is 50.26 (9)° and the C—S—N—C bond adopts a gauche conformation [torsion angle = −68.12 (15)°]. The dihydrodioxine ring is disordered over two orientations, which both approximate to half-chairs, in a 0.880 (7):0.120 (7) ratio. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [100]. Weak C—H⋯O and C—H⋯F interactions consolidate the packing.

Related literature

For related structures, see: Khan et al. (2011 ▶); Gelbrich et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₂FNO₄S
M _r = 309.31
Monoclinic,
a = 5.1542 (5) Å
b = 22.237 (3) Å
c = 12.0706 (13) Å
β = 94.422 (3)°
V = 1379.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.39 × 0.34 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
11762 measured reflections
3156 independent reflections
2336 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.101
S = 1.02
3156 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 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/S1600536812030863/bt5970sup1.cif

e-68-o2433-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030863/bt5970Isup2.hkl

e-68-o2433-Isup2.hkl^{(154.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030863/bt5970Isup3.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
N1—H1⋯O2ⁱ	0.81 (2)	2.22 (2)	3.009 (2)	164 (2)
C3—H3⋯O1ⁱⁱ	0.93	2.53	3.368 (3)	150
C5—H5⋯O4ⁱⁱⁱ	0.93	2.56	3.391 (2)	149
C8—H8⋯O3^iv	0.93	2.52	3.446 (2)	172
C13—H13B⋯F1^v	0.97	2.48	3.129 (3)	125

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound, (I), (Fig. 1) was examined as part of our ongoing interest in the structural chemistry of sulfonamides (Khan et al., 2011). A number of related structures have been reported by Gelbrich et al. (2007).

The dihedral angle between the C1—C6 and C7—C12 benzene rings in (I) is 50.26 (9)°. The C1—S1—N1—C7 linkage adopts a gauche conformation [torsion angle = -68.12 (15)°] and the bond-angle sum about N1 (H atom coordinates freely refined) is 347.2°, possibly suggesting a hybridization state intermediate between sp² and sp³. The largest bond angle at the distorted tetrahedral S atom is O1—S1—O2 [120.26 (9)°], which is typical for this class of compound (Khan et al., 2011).

Atoms C13 and C14 and their attached H atoms of the dihydro-dioxin ring are disordered over two sets of sites in a 0.880 (7):0.120 (7) ratio. Both major and minor conformations approximate to a half-chair. In the major conformation, C13 and C14 are displaced from the plane defined by C7—C12/O3/O4 (r.m.s. deviation = 0.037 Å) by 0.212 (3) and -0.556 (3) Å, respectively. The equivalent atoms in the minor component are displaced by -0.44 (3) and 0.41 (2) Å, respectively.

In the crystal, the molecules are linked by N—H···O hydrogen bonds (Table 1) to generate C(4) chains propagating in [100] (Figure 2). Weak C—H···O and C—H···F interactions also occur but there is no aromatic π-π stacking in the structure of (I).

Experimental

0.2 g of 6-amino 1,4-benzodioxan was dissolved in 15 ml dichloromethane and 0.25 g of 4-fluorobenzene sulfonyl chloride was added to the mixture, which was stirred at room temperature overnight. The pH was maintained at 8–9 with triethyamine. On completion of reaction (after TLC) the pH was adjusted to 1–2 with 1 M HCl solution. The organic fraction was collected and the solvent was allowed to evaporate at room temperature. Colourless prisms of (I) were obtained in 95% yield.