N-(2,5-Dimethoxy­phen­yl)-4-nitro­benzene­sulfonamide

Guo-Yao Zhang; Shan Qian; Xiao-Cen Li; Yong Wu

doi:10.1107/S1600536809027962

. 2009 Jul 22;65(Pt 8):o1939. doi: 10.1107/S1600536809027962

N-(2,5-Dimethoxyphenyl)-4-nitrobenzenesulfonamide

Guo-Yao Zhang ^a, Shan Qian ^a, Xiao-Cen Li ^a, Yong Wu ^a,^*

PMCID: PMC2977360 PMID: 21583621

Abstract

The title compound, C₁₄H₁₄N₂O₆S, is an intermediate for the synthesis of β-3-adrenergic receptor agonists. The two methoxy groups are approximately coplanar with the attached benzene ring [C—O—C—C = −2.7 (4) and 9.4 (4)°]. The dihedral angle between the two aromatic rings is 67.16 (12)°. An intramolecular N—H⋯O hydrogen bond is observed. In the crystal, molecules are linked into chains along the c axis by C—H⋯O hydrogen bonds.

Related literature

For biological activity of β-3-adrenergic receptors, see: Bardou et al. (1998 ▶); Hu et al. (2001 ▶); Klaus et al. (2001 ▶); Margareto et al. (2001 ▶); Ok et al. (2000 ▶); Parmee et al. (1998 ▶, 2000 ▶); Tonello et al. (1998 ▶); Weber et al. (1998 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O₆S
M _r = 338.33
Orthorhombic,
a = 14.532 (4) Å
b = 12.375 (4) Å
c = 17.311 (4) Å
V = 3113.2 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 292 K
0.48 × 0.44 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: for a sphere (WinGX; Farrugia, 1999 ▶) T _min = 0.893, T _max = 0.906
4003 measured reflections
2877 independent reflections
1790 reflections with I > 2σ(I)
R _int = 0.004
3 standard reflections every 200 reflections intensity decay: 0.9%

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.121
S = 1.06
2877 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809027962/ci2846sup1.cif

e-65-o1939-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027962/ci2846Isup2.hkl

e-65-o1939-Isup2.hkl^{(141.3KB, hkl)}

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—H1N⋯O2	0.78 (3)	2.20 (3)	2.607 (3)	113 (2)
C8—H8C⋯O4ⁱ	0.96	2.55	3.414 (4)	150

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The beta 3-adrenergic receptor has been shown to mediate various pharmacological and physiological effects such as lipolysis in white adipocyte tissue, thermogenesis in brown adipocyte tissue (Tonello et al., 1998; Ok et al., 2000; Parmee et al., 1998, 2000) and relaxation of urinary bladder detrusor tissue (Hu et al., 2001; Parmee et al., 1998; Weber et al., 1998). Consequently, several pharmaceutical firms, including ourselves, are engaged in developing potent and selective beta 3-adrenergic receptor agonists for the treatment of obesity, type II diabetes, and frequent urination (Margareto et al., 2001; Bardou et al., 1998; Klaus et al., 2001). In our synthetic work of beta 3-adrenergic receptor agonists, we obtained the title compound. Its crystal structure is reported here.

The two methoxy groups are approximately coplanar with the attached benzene ring [C7—O1—C3—C4 = -2.7 (4)° and C8—O2—C6—C5 9.4 (4)°]. The nitro group is coplanar with the C9-C14 benzene ring. The dihedral angle between the two aromatic rings is 67.16 (12)°. An intramolecular N—H···O hydrogen bond is observed.

The crystal packing of the title compound shows that the molecules are linked by C—H···.O hydrogen bonds (Table 1) to form chains along the c axis.

Experimental

2,5-Dimethoxybenzenamine (10 mmol) and excess pyridine were dissolved in dichloromethane (20 ml) and a solution of 4-nitrobenzene-1-sulfonyl chloride (13 mmol) in dichloromethane (20 ml) was added dropwise with vigorous stirring at 273 K. After 1 h, the reaction was quenched by addition of water and the oil was washed with diluted HCl. The organic layer separated was evaporated to give the crude product, which was recrystallized from n-hexane -dichloromethane (5:1). Colourless crystals suitable for X-ray analysis were obtained by slow evaporation in n-hexane-dichloromethane at room temperature.