N-(4-Meth­oxy-2-nitro­phen­yl)-N-(methyl­sulfon­yl)methane­sulfonamide

Sammer Yousuf; Hina Siddiqui; Rabia Farooq; M Iqbal Choudhary

doi:10.1107/S160053681202483X

. 2012 Jun 13;68(Pt 7):o2090. doi: 10.1107/S160053681202483X

N-(4-Methoxy-2-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide

Sammer Yousuf ^a,^*, Hina Siddiqui ^a, Rabia Farooq ^a, M Iqbal Choudhary ^a,^b

PMCID: PMC3393905 PMID: 22798770

Abstract

In the title compound, C₉H₁₂N₂O₇S₂, the nitro substituent is slightly twisted from the benzene ring [dihedral angle = 14.69 (10)°]. The molecular geometry is stabilized by intramolecular C—H⋯O hydrogen bonds, forming S(6) ring motifs. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into layers parallel to (10-2).

Related literature

For the biological activities of sulfonamides, see: Alsughayer et al. (2011 ▶); Joshi & Khosla (2003 ▶); Scozzafava et al. (2003 ▶); Drews (2000 ▶); Peixoto & Beverley (1987 ▶). For crystal structures of closely related compounds, see: Boechat et al. (2010 ▶); Zia-ur-Rehman et al. (2009 ▶).

Experimental

Crystal data

C₉H₁₂N₂O₇S₂
M _r = 324.33
Monoclinic,
a = 9.4976 (7) Å
b = 7.5987 (6) Å
c = 19.2434 (15) Å
β = 103.672 (2)°
V = 1349.43 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 273 K
0.55 × 0.47 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.799, T _max = 0.955
9504 measured reflections
3362 independent reflections
2711 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.113
S = 1.05
3362 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202483X/is5148sup1.cif

e-68-o2090-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202483X/is5148Isup2.hkl

e-68-o2090-Isup2.hkl^{(164.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202483X/is5148Isup3.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
C1—H1B⋯O2ⁱ	0.93	2.46	3.368 (2)	165
C8—H8B⋯O4	0.96	2.58	3.225 (3)	125
C8—H8C⋯O5ⁱⁱ	0.96	2.58	3.250 (3)	127
C9—H9B⋯O1	0.96	2.59	3.226 (3)	124
C9—H9B⋯O1ⁱⁱⁱ	0.96	2.47	3.173 (3)	130

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

supplementary crystallographic information

Comment

Compounds containing the sulfonamide moiety have attracted a wide interest due to their interesting chemical and biological properties, which makes them promising candidates in drug discovery. Sulfonamides posses wide variety of biological activities including anti-bacterial, anti-leishmanial, anti-inflammatory, anti-cancer, and carbonic anhydrase inhibitory activities (Alsughayer et al., 2011; Joshi & Khosla, 2003; Scozzafava et al., 2003; Drews, 2000; Peixoto & Beverley, 1987). The title compound was prepared as a part of our ongoing research to synthesize different sulfonamide derivatives to study their bioactive potential and structure activity relationship (SAR). In the title compound (Fig. 1), the nitro group was found to be slightly twisted with the dihedral angle of 14.69 (10)° between the NO₂ group and the benzene ring. The S1—N2—C3—C4 and S2—N2—C3—C4 torsion angles are 82.83 (19) and -92.42 (17)°, respectively. The molecule is stabilized by two intramolecular C8—H8B···O4 and C9—H9B···O1 interactions to form two S(6) ring motifs. In the crystal structure, the molecules are linked to form a two-dimensional network through C1—H1B···O2ⁱ, C8—H8C···O5ⁱⁱ and C9—H9B···O1ⁱⁱⁱ intermolecular hydrogen bonds (Fig. 2 and Table 1). The bond lengths and angles are within the normal range and similar to other closley related structures (Boechat et al., 2010; Zia-ur-Rehman et al., 2009).

Experimental

To a stirring solution of methanesulfonyl chloride (1.0 g, 8.7 mmol) in CH₂Cl₂ (20 ml) at 0 °C, 3 ml Et₃N and 4-methoxy-2-nitroaniline (1.1 eq., 1.61 g m, 9.6 mmol) were added along with catalytic amount of dimethylamino pyridine (DMAP). Progress of the reaction was monitored by thin layer chromatography in 7:3 hexanes: ethyl acetate solvent system. After complete consumption of starting material (2 hrs), workup was performed with H₂O (10 ml), organic layer was separated and aqueous layer was extracted with CH₂Cl₂ (2 × 10 ml). Organic layers were further washed with brine (10 ml), and dried over MgSO₄, filtered, and concentrated in vacuum to obtain the crude product (0.9 g, 90% yield). Flash chromatography was performed hexanes: ethyl acetate (7:3), to obtain crystalline compound I, in 55% yield. Crystals were found suitable for single-crystal X-ray diffraction studies. All the starting materials and solvents were purchased from commercial suppliers and used for reaction without purification.