(2Z)-2-{[N-(2-Formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}-3-(4-methyl­phen­yl)prop-2-ene­nitrile

D Kannan; M Bakthadoss; R Madhanraj; S Murugavel

doi:10.1107/S1600536812010628

. 2012 Mar 17;68(Pt 4):o1084. doi: 10.1107/S1600536812010628

(2Z)-2-{[N-(2-Formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(4-methylphenyl)prop-2-enenitrile

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

PMCID: PMC3344039 PMID: 22589948

Abstract

In the title compound, C₂₅H₂₂N₂O₃S, the sulfonyl-bound benzene ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formylbenzene and methylbenzene rings. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(5) ring motif. The crystal packing is stabilized by C—H⋯O hydrogen bonds, which generate C(11) chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.927 (2) Å].

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Madhanraj et al. (2012 ▶); Aziz-ur-Rehman et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₅H₂₂N₂O₃S
M _r = 430.51
Orthorhombic,
a = 8.9432 (5) Å
b = 10.3004 (6) Å
c = 24.9240 (15) Å
V = 2296.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.972
12317 measured reflections
4663 independent reflections
3385 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.117
S = 1.02
4663 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 1990 Friedel pairs
Flack parameter: 0.19 (9)

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/S1600536812010628/tk5066sup1.cif

e-68-o1084-sup1.cif^{(29.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010628/tk5066Isup2.hkl

e-68-o1084-Isup2.hkl^{(223.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010628/tk5066Isup3.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
C15—H15A⋯O3	0.97	2.45	2.904 (3)	109
C23—H23⋯O1ⁱ	0.93	2.50	3.142 (4)	127

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Symmetry code: (i) Inline graphic .

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 (I) 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 the O2—S1—O3 [119.9 (1)°] and N1—S1—C8[107.5 (1)°] angles deviating from ideal tetrahedral values. The sum of bond angles around N1 (351.9°) indicates that N1 has sp² hybridization. The sulfonyl bound benzene (C8–C13) ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formyl benzene (C1–C6) and methylbenzene (C18—C23) rings. The dihedral angle between formyl benzene and methylbenzene rings is 87.4 (1)°. The carbonitrile side chain (C16–C24–N2) is almost linear, with the angle around the C24 atom being 177.1 (3)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Madhanraj et al., 2012, Aziz-ur-Rehman et al., 2010).

The molecular structure is stabilized by a C15—H15A···O3 intramolecular hydrogen bond, forming a S(5) ring motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. Atom C23 in the molecule at (x, y, z) donates one proton to atom O1 at (x, -1 + y, z), forming a C(11) chain along the b axis (Fig. 2). The crystal packing is further stabilized by π—π interactions with centroid—centroid distances: Cg1—Cg2^iv = 3.927 (2) Å and Cg2—Cg1^v = 3.927 (2) Å (Fig. 3; Cg1 and Cg2 are the centroids of C8–C13 benzene ring and C18–C23 benzene rings, respectively, symmetry code as in Fig. 3).

Experimental

A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.275 g) and potassium carbonate (1.5 mmol, 0.207 g) in acetonitrile was stirred for 15 minutes at room temperature. To this solution, (E)-2-(bromomethyl)-3-(4-methylphenyl)prop-2-enenitrile (1.2 mmol, 0.283 g) was added drop wise until the addition was completed. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated off. Ethylacetate (15 ml) and water (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 a 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 (0.41 g, 95% yield). Recrystallization was carried out using ethylacetate as solvent.