N-(2-Formyl­phen­yl)-4-meth­oxy-N-(4-meth­oxy­phenyl­sulfon­yl)benzene­sulfonamide

Najat Abbassi; El Mostapha Rakib; Abdellah Hannioui; Hafid Zouihri

doi:10.1107/S1600536811047192

. 2011 Nov 12;67(Pt 12):o3304. doi: 10.1107/S1600536811047192

N-(2-Formylphenyl)-4-methoxy-N-(4-methoxyphenylsulfonyl)benzenesulfonamide

Najat Abbassi ^a, El Mostapha Rakib ^a,^*, Abdellah Hannioui ^a, Hafid Zouihri ^b

PMCID: PMC3238957 PMID: 22199806

Abstract

In the title compound, C₂₁H₁₉NO₇S₂, the dihedral angles between the formylphenyl ring and the two methoxyphenyl rings are 33.87 (9) and 41.00 (10)°. The S atoms have a distorted tetrahedral geometry and the N atom shows a trigonally planar [r.m.s. deviation = 0.0437 (13) Å] coordination. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Abbassi et al. (2011a ▶,b ▶). For the biological activity of sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee (2002 ▶); Lopez et al. (2010 ▶); Zuercher et al. (2010 ▶). For the synthesis of 7-ethoxy-N-alkylindazole derivatives, see: Abbassi et al. (2011c ▶).

Experimental

Crystal data

C₂₁H₁₉NO₇S₂
M _r = 461.49
Monoclinic,
a = 9.0559 (3) Å
b = 25.8904 (10) Å
c = 9.3844 (3) Å
β = 103.423 (2)°
V = 2140.17 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.24 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD detector diffractometer
37297 measured reflections
7971 independent reflections
4874 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.139
S = 1.01
7971 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047192/bt5702sup1.cif

e-67-o3304-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047192/bt5702Isup2.hkl

e-67-o3304-Isup2.hkl^{(390KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047192/bt5702Isup3.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
C14—H14⋯O4ⁱ	0.93	2.54	3.346 (2)	145
C16—H16⋯O2ⁱⁱ	0.93	2.45	3.237 (3)	143
C19—H19B⋯O6ⁱⁱⁱ	0.96	2.59	3.455 (3)	151

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

Sulfonamides constitute an important class of drugs (Lopez et al., 2010; Zuercher et al., 2010). They possess various types of pharmacological activities such as antibacterial, hypoglycemic, anti-inflammatory, and antitumor agents (Soledade et al., 2006; Lee & Lee, 2002).

In former papers, we reported the crystal structures of N-(7-ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide (Abbassi et al., 2011a) and N-[7-ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide (Abbassi et al., 2011b). In this communication, the crystal structure of N-(2-formylphenyl)-4-methoxy-N-[(4-methoxyphenyl)sulfonyl]benzenesulfonamide is reported.

In the title compound, C₂₁H₁₉NO₇S₂, the C—S—N—S torsion angles are 83.22 (11)° and 110.03 (10)°, respectively. The dihedral angles between the two methoxyphenyl rings and the formylphenyl ring are 33.87 (9)° and 41.00 (10)°, respectively. The S atoms have a distorted tetrahedral geometry [maximum deviation: O—S—O = 119.93 (11)° and 120.36 (9)°, respectively].

In the crystal, molecules are connected by intermolecular C—H···O hydrogen contacts.

Experimental

A mixture of 2-nitrobenzaldehyde (1.22 mmol) and anhydrous SnCl₂(1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was stirred for 1 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was made slightly basic (pH 7–8) by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methoxybenzenesulfonylchloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with Ethyl acetate: Hexane 3:7).