N-[2-(3,4-Dimeth­oxy­phen­yl)eth­yl]-N,4-dimethyl­benzene­sulfonamide

Jasmine P Vennila; D John Thiruvadigal; Helen P Kavitha; G Chakkaravarthi; V Manivannan

doi:10.1107/S1600536811029746

. 2011 Jul 30;67(Pt 8):o2186. doi: 10.1107/S1600536811029746

N-[2-(3,4-Dimethoxyphenyl)ethyl]-N,4-dimethylbenzenesulfonamide

Jasmine P Vennila ^a, D John Thiruvadigal ^b, Helen P Kavitha ^c, G Chakkaravarthi ^d,^*, V Manivannan ^e

PMCID: PMC3213618 PMID: 22091195

Abstract

In the title compound, C₁₈H₂₃NO₄S, the dihedral angle between the two aromatic rings is 29.14 (7)°. The S atom has a distorted tetrahedral geometry [106.15 (9)–119.54 (10)°]. The crystal structure exhibits weak C—H⋯O and π–π interactions.

Related literature

For the biological activity of sulfonamide derivatives, see: Chumakov et al. (2006 ▶); Kremer et al. (2006 ▶). For related structures, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C₁₈H₂₃NO₄S
M _r = 349.43
Monoclinic,
a = 5.7814 (4) Å
b = 13.9861 (12) Å
c = 21.9791 (18) Å
β = 92.949 (4)°
V = 1774.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.942, T _max = 0.960
18724 measured reflections
3343 independent reflections
2614 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.04
3343 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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 datablock(s) global, I. DOI: 10.1107/S1600536811029746/bt5588sup1.cif

e-67-o2186-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029746/bt5588Isup2.hkl

e-67-o2186-Isup2.hkl^{(160.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029746/bt5588Isup3.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
C12—H12⋯O1ⁱ	0.93	2.54	3.452 (2)	166
C18—H18B⋯O2ⁱⁱ	0.96	2.38	3.302 (3)	160

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

Acknowledgments

The authors wish to acknowledge SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

Sulfonamide derivatives are extensively used in medicine as they possess a wide range of medicinal, pharmacological and antimicrobial properties (Chumakov et al., 2006, Kremer et al., 2006). We report the crystal structure of the titled compound (I) (Fig. 1).

In the title compound (I), the geometric pararameters are similar with the reported similar structures (Khan et al., 2010; Sharif et al., 2010). The S atom of the title molecule has a distorted tetrahedral geometry, with S1—O1 = 1.4210 (15), S1—O2 = 1.4195 (15), S1—N1 = 1.6391 (17), S1—C1 = 1.7538 (19) Å, O1—S1—O2 = 119.54 (10), O1—S1—N1 = 106.83 (9), O1—S1—C7 = 108.64 (9), O2—S1—N1 = 106.32 (9), O2—S1—C7 = 108.57 (9) and N1—S1—C7 = 106.15 (9)°.

The dihedral angle between the two rings C1—C6 and C11—C16 is 29.14 (7)°. The crystal structure exhibits weak C—H···O (Fig.2 and Table 1) and π–π [Cg1···Cg2 (-x,2 - y,-z) distance of 5.2909 (13)Å and Cg2···Cg2 (-x,1 - y,-z) distance of 4.7146 (12) Å; Cg1 and Cg2 are the centroids of the rings C1—C6 and C11—C16, respectively] interactions.

Experimental

2-(3,4-dimethoxyphenyl)-N-methyl ethanamine (51 mmol) was dissolved in dichloromethane (20 ml) in a round bottom flask. To this, added triethylamine (10.2 mmol) with stirring for 5 minutes. Then 4-methylbenzene-1-sulfonyl chloride (51 mmol) was added into the reaction mass and heated to 50 °C for 6 hrs. After cooling the reaction mixture to the normal temperature, it was added to water (20 ml). The aqueous layer was separated. The ethyl acetate layer was washed twice with 10% sodium chloride solution. The organic layer was dried over 2 g of anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to isolate the crude compound. Recrystallization of the compound using ethyl acetate and hexane mixture yielded the diffraction quality crystals.