Ethyl 3-[2-(p-toluene­sulfonamido)phen­yl]acrylate

Mei-Fang Jin; Bao-Yong Zhu

doi:10.1107/S1600536809034163

. 2009 Sep 5;65(Pt 10):o2312. doi: 10.1107/S1600536809034163

Ethyl 3-[2-(p-toluenesulfonamido)phenyl]acrylate

Mei-Fang Jin ^a,^*, Bao-Yong Zhu ^b

PMCID: PMC2970429 PMID: 21577783

Abstract

In the title compound, C₁₈H₁₉NO₄S, the two benzene rings form a dihedral angle of 52.2 (7)°. The crystal struture is stabilized by N—H⋯O hydrogen bonds, which link the molecules into dimers.

Related literature

For functionalized carbon frameworks, see: Mukherjee et al. (2007 ▶). For sulfonamido compounds and their use in pharmaceuticals, see: Patchett et al. (1995 ▶). For a related structure, see: Senthil Kumaret al. (2006 ▶).

Experimental

Crystal data

C₁₈H₁₉NO₄S
M _r = 345.40
Triclinic,
a = 8.001 (4) Å
b = 10.245 (5) Å
c = 11.402 (5) Å
α = 81.182 (5)°
β = 70.895 (4)°
γ = 86.604 (5)°
V = 872.7 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 291 K
0.46 × 0.43 × 0.38 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.91, T _max = 0.93
15343 measured reflections
3553 independent reflections
2784 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.147
S = 1.18
3553 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrysAlis Pro (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Pearce & Watkin, 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034163/bg2295sup1.cif

e-65-o2312-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034163/bg2295Isup2.hkl

e-65-o2312-Isup2.hkl^{(174.2KB, 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—H1⋯O3ⁱ	0.92	2.01	2.920 (2)	172

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authours thank the Anyang Institute of Technology, the Natural Science Foundation of Shandong (project code: Y 2007F 68), the Scientific Research Developmental Project of Shandong Provincial Education Department (project code: J07WC09) and the Scientific Developmental Project of Dezhou City (project code 050702) for support.

supplementary crystallographic information

Comment

Electron-deficient olefin, particularly α,β-unsaturated carbonyl compound, was used as a fundamental material to construct functionalized carbon frameworks (Mukherjee et al., 2007). Sulfonamido is an important group in natural compounds and many pharmaceuticals (Patchett et al., 1995). We selected N-(2-formylphenyl)(4-methylbenzene)sulfonamide and (ethoxycarbonylmethylene)triphenylphosphorane to synthesize a new compound formulated as C₁₈H₁₉N₁O₄S₁ (I) with dimeric structures via hydrogen bonds.

The molecular structure of (I) is illustrated in Fig. 1. The geometry of the molecule is close to the related compound Ethyl 2-([N-(2- iodophenyl)phenylsulfonamido]methyl)-1-phenylsulfonyl-1H-indole-3- carboxylate (Senthil Kumar, et al., 2006). Bond lengths and angles (S1—O1 =1.427 (1) Å, S1—O2 = 1.431 (1) Å, O1-S1-O2 = 121.3 (1) °, O1-S1-N1 = 107.3 (9) °, O2S1N1 = 104.7 (1) °) involving the S atom of the phenylsufonyl group present in the molecule is similar to the distances (S1—O1 = 1.425 Å, S1—O2 = 1.429 Å) and angles (O1-S1-O2 = 120.4 (8) °, O1-S1-N1 = 106.9 (7) °, O2-S1-N1 = 106.7 (7) °)) that reported in the literature (Senthil Kumar, et al., 2006); the O—S—O, N—S—C and N—S—O angles deviate significantly from the ideal tetrahedral value (Table 1), which is consistent to the reported data in the literature (Senthil Kumar, et al., 2006). The phenyl rings (C2—>C7) and (C8—>C13) are planar to within 0.01 Å. The dihedral angle between the two phenyl rings is 52.3 (1) °.

The crystal struture is further stabilized by hydrogen bonding. As shown in Fig.2, a dimeric structure is formed via intermolecular hydrogen bonds N1—H2···O3ⁱ (i = 1 - x, 1 - y, -z) (Table 2).

Experimental

The mixture of N-(2-formylphenyl)(4-methylbenzene)sulfonamide (0.500 g, 1.82 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (0.700 g, 2.00 mmol) in dichloromethane (10 ml) was stirred at room temperature for 2 h (Scheme 2). After evaporation of the solvent, the title compound was obtained from the residue by chromatography. Single crystals suitable for X-ray analysis were obtained from ethyl acetate by slow evaporation.