Methyl (Z)-2-{[N-(2-formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}-3-phenyl­prop-2-enoate

R Madhanraj; S Murugavel; D Kannan; M Bakthadoss

doi:10.1107/S1600536811050756

. 2011 Nov 30;67(Pt 12):o3511. doi: 10.1107/S1600536811050756

Methyl (Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-phenylprop-2-enoate

R Madhanraj ^a, S Murugavel ^b,^*, D Kannan ^c, M Bakthadoss ^c,^‡

PMCID: PMC3239132 PMID: 22199980

Abstract

In the title compound, C₂₅H₂₃NO₅S, the sulfonyl-bound benzene ring forms dihedral angles of 37.2 (1) and 67.0 (1)°, respectively, with the formylphenyl and phenyl rings. The molecular conformation is stabilized by an intramolecular C—H⋯π interaction. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a two-dimensional network in the (110) plane in which R ₄ ⁴(38) ring motifs are generated.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Ranjith et al. (2009 ▶); Aziz-ur-Rehman et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the Thrope–Ingold effect, see: Bassindale (1984 ▶).

Experimental

Crystal data

C₂₅H₂₃NO₅S
M _r = 449.50
Monoclinic,
a = 9.7475 (5) Å
b = 21.7053 (12) Å
c = 11.2643 (6) Å
β = 109.987 (2)°
V = 2239.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.971
28975 measured reflections
6991 independent reflections
4593 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.153
S = 0.99
6991 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050756/bt5721sup1.cif

e-67-o3511-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050756/bt5721Isup2.hkl

e-67-o3511-Isup2.hkl^{(335.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050756/bt5721Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg	0.93	2.64	3.470 (2)	149
C25—H25B⋯O2ⁱ	0.96	2.56	3.342 (3)	139
C10—H10⋯O1ⁱⁱ	0.93	2.51	3.309 (3)	145

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

Acknowledgments

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988, Mandell & Sande, 1992). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The S1 atom shows a distorted tetrahedral geometry, with O2—S1—O3 [119.6 (1)°] and N1—S1—C8 [107.5 (1)°] angles deviating from ideal tetrahedral values, are attributed to the Thrope-Ingold effect (Bassindale, 1984). The sum of bond angles around N1 (351.5°) indicates that N1 is in sp² hybridization. The sulfonyl bound phenyl (C8–C13) ring forms dihedral angles of 37.2 (1)° and 67.0 (1)°, respectively, with the formyl phenyl (C1–C6) and phenyl (C18—C23) rings. The dihedral angle between formyl phenyl and phenyl rings is 45.9 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Ranjith et al., 2009; Aziz-ur-Rehman et al., 2010).

The molecular structure is stabilized by intramolecular C-H···π interaction between a sulfonyl bound phenyl H9 atom and a phenyl (C18–C23) ring with a C9—H9···Cg seperation of 2.64 Å.(Fig. 1 and Table 1; Cg is the centroid of the C18–C23 phenyl ring). In the crystal four molecules are linked by intermolecular C—H···O hydrogen bonds (Fig. 2, Table 1; Symmetry codes as given in Fig. 2), generating R₄⁴(38) ring motifs (Bernstein et al., 1995) to form a two dimensional network along [110]] directions.

Experimental

A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.28 g) and potassium carbonate (1.5 mmol, 0.21 g) in acetonitrile solvent was stirred for 15 minutes at room temperature. To this solution, (z)-methyl-2-(bromomethyl)-3-phenylprop-2-enoate (1.2 mmol, 0.30 g) was added dropwise till the addition is complete. After the completion of the reaction, as indicated by TLC, acetonitile was evaporated. ETOAc (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100-200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.40 g, 88 % yield). Recrystallization was carried out using ethylacetate as solvent.