4-Bromo-3-{N-[2-(3,4-dimethoxy­phen­yl)eth­yl]-N-methyl­sulfamo­yl}-5-methyl­benzoic acid monohydrate

C Suneel Manohar Babu; Helen P Kavitha; Jasmine P Vennila; G Chakkaravarthi; V Manivannan

doi:10.1107/S1600536809022041

. 2009 Jun 13;65(Pt 7):o1568. doi: 10.1107/S1600536809022041

4-Bromo-3-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylsulfamoyl}-5-methylbenzoic acid monohydrate

C Suneel Manohar Babu ^a, Helen P Kavitha ^b, Jasmine P Vennila ^c, G Chakkaravarthi ^d, V Manivannan ^e,^*

PMCID: PMC2969419 PMID: 21582848

Abstract

In the title compound, C₁₉H₂₂BrNO₆S·H₂O, the dihedral angle between the planes of the two benzene rings is 3.1 (1)°. These rings are stacked over one another with their centroids separated by 3.769 (2) Å, indicating weak π–π interactions. In the crystal structure, molecules are linked by O—H⋯O and O—H⋯(O,O) hydrogen bonds involving the water molecule, forming a two-dimensional network parallel to (001).

Related literature

For the biological activity of sulfonamides, see: Cates (1986 ▶); Steele & Beran (1984 ▶); Benedetti (1987 ▶); Mengelers et al. (1997 ▶). For related structures, see: Babu et al. (2009a ▶,b ▶); Shad et al. (2009 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C₁₉H₂₂BrNO₆S·H₂O
M _r = 490.36
Orthorhombic,
a = 7.7938 (2) Å
b = 7.8280 (2) Å
c = 34.6549 (8) Å
V = 2114.29 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.08 mm⁻¹
T = 295 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.745, T _max = 0.819
12583 measured reflections
4619 independent reflections
3427 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.107
S = 1.05
4619 reflections
275 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ▶), 1915 Friedel pairs
Flack parameter: −0.004 (10)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022041/ci2818sup1.cif

e-65-o1568-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022041/ci2818Isup2.hkl

e-65-o1568-Isup2.hkl^{(221.7KB, 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
O2—H2A⋯O1W	0.82	1.73	2.535 (4)	169
O1W—H1W⋯O1ⁱ	0.79 (3)	1.97 (4)	2.732 (5)	162 (6)
O1W—H2W⋯O5ⁱⁱ	0.75 (3)	2.46 (4)	3.066 (5)	139 (5)
O1W—H2W⋯O6ⁱⁱ	0.75 (3)	2.14 (4)	2.828 (5)	154 (5)

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

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology-Madras, Chennai, for the data collection.

supplementary crystallographic information

Comment

Sulfonamides are a class of anti-microbial agents that have seen extensive use in medicine. They are the first agents to be used for the treatment of bacterial infection (Cates, 1986). Sulfonamides are used to treat atrophic rhinitis in swine and heart water in cattle and many other diseases in a variety of animals (Steele & Beran, 1984). In adition sulfonamides have a variety of biological activities such as antibacterial, antimalarial and antileprotic agents (Benedetti, 1987; Mengelers et al., 1997).

The geometric parameters of the title molecule agree well with those reported for similar structures (Babu et al., 2009a,b; Shad et al., 2009). In the molecular structure, the two benzene rings are stacked over one another with their centroids separated by 3.769 (2) Å, indicating a weak π-π interaction. The dihedral angle between the two benzene rings is 3.1 (1)°. A distorted tetrahedral geometry [O3—S1—O4 = 118.7 (2)° and O3—S1—N1 = 108.8 (2) °] is observed around S1 atom.

In the crystal structure, O—H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network parallel to the (0 0 1). The O1W—H2W···O5 and O1W—H2W···O6 bifurcated donar bonds generate an R₁²(5) ring motif (Bernstein et al., 1995).

Experimental

A solution of 2-(3,4-dimethoxyphenyl)-N-methyl ethanamine (1 g, 0.0051 mol) in ethyl acetate (20 ml) was charged into a round bottom flask equipped with thermometer pocket, condenser and guard tube. Then, pyridine (0.81 g, 0.0102 mol) was added at 25–30°C. After 5 min stirring, 2-bromo-5-(chlorosulfonyl)-3-methylbenzoic acid (0.96 g, 0.00307 mol) was charged into the reaction mass and heated to 45-50°C and maintained for 5-6 h. The completion of the reaction was checked by thin layer chromatography (1:1 hexane-ethyl acetate) and the reaction mass was cooled to 25–30 °C and quenched with 20 ml of water. Then, the aqueous layer was separated and the ethyl acetate layer was washed twice with 10% sodium chloride solution and dried over 2 g of anhydrous sodium sulfate. The solvent was distilled under vacuum at 35-40°C and the crude compound isolated. The crude compound was purified through column chromatography using hexane and ethyl acetate as eluents.