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

R Madhanraj; S Murugavel; D Kannan; M Bakthadoss

doi:10.1107/S160053681105241X

. 2011 Dec 14;68(Pt 1):o56–o57. doi: 10.1107/S160053681105241X

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

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

PMCID: PMC3254413 PMID: 22259557

Abstract

In the title compound, C₂₄H₁₉ClN₂O₃S, the sulfonyl-bound benzene ring forms dihedral angles of 38.1 (2) and 81.2 (1)°, respectively, with the formyl benzene and benzene rings. The molecular conformation is stabilized by a weak 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(7) zigzag chains along [010] and R ₃ ³(19) ring motifs along [010]. The crystal packing is further stabilized by C—Cl⋯π interactions [Cl⋯centroid = 3.456 (2) Å and C—Cl⋯centroid = 173.4 (2)°].

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 ▶).

Experimental

Crystal data

C₂₄H₁₉ClN₂O₃S
M _r = 450.92
Orthorhombic,
a = 8.9795 (5) Å
b = 10.1590 (5) Å
c = 25.1050 (13) Å
V = 2290.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 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 = 0.931, T _max = 0.953
12721 measured reflections
4850 independent reflections
3396 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.111
S = 1.03
4850 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 2049 Friedel pairs
Flack parameter: 0.06 (8)

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/S160053681105241X/bt5740sup1.cif

e-68-00o56-sup1.cif^{(22KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105241X/bt5740Isup2.hkl

e-68-00o56-Isup2.hkl^{(232.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681105241X/bt5740Isup3.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	2.43	2.890 (3)	109
C3—H3⋯O2ⁱ	0.93	2.57	3.345 (3)	141
C15—H15A⋯O2ⁱⁱ	0.97	2.57	3.385 (3)	142
C23—H23⋯O1ⁱⁱⁱ	0.93	2.45	3.114 (4)	128

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

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[119.8 (1)°] and N1—S1—C8[107.5 (1)°] angles deviating from ideal tetrahedral values. The sum of bond angles around N1 (352°) indicates that N1 is in sp² hybridization. The sulfonyl bound phenyl (C8–C13) ring forms dihedral angles of 38.1 (2)° and 81.2 (2)°, respectively, with the formyl phenyl (C1–C6) and phenyl (C18—C23) rings. The dihedral angle between formyl phenyl and phenyl rings is 87.3 (1)°. The Cl1 atom deviates from the plane of attached ring by -0.031 (2) Å. The carbonitrile side chain (C16–C24–N2) is almost linear, with the angle around central carbon atom being 176.9 (3)°. 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).

Ihe molecular structure is stabilized by C15—H15A···O3 intramolecular hydrogen bond, forming S(5) ring motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. The formation of the framework can be explained in terms of two-one substructures. In the first substructure, atom C3 in the molecule at (x, y, z) acts as a hydrogen bond donor to atom O2 in the molecule at (2-x,1/2+y,1/2-z) generating C(7) zig zag chains which are running along [010] (Fig. 2). In the second substructure, three molecules are linked by the combination of C15—H15A···O2 and C23—H23···O1 intermolecular hydrogen bonds generating R₃³(19) ring motifs along [010] (Fig. 3). The crystal structure is further stabilized by C—Cl···.π interactions involving chlorine Cl1 and benzene ring (C1–C6), with Cl1···centroid(Cgⁱ) distance of 3.456 (2) Å and C21—Cl1···Cgⁱ angle of 173.4 (2)° (Symmetry code as in Fig. 4). The crystal packing also exhibts π—π interactions with centroid—centroid distances: Cg2—Cg3ⁱⁱ = 3.884 (2) Å and Cg3—Cg2ⁱⁱⁱ = 3.884 (2) Å (Fig. 4; Cg2 and Cg3 are the centroids of C18–C23 benzene ring and C8–C13 benzene ring, respectively, symmetry code as in Fig. 4).

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, (E)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enenitrile (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. 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 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, 90 % yield). Recrystallization was carried out using ethylacetate as solvent.