(Z)-3-(4-Fluoro­phen­yl)-1-[4-(methyl­sulfon­yl)phen­yl]-2-tosyl­prop-2-en-1-one

S Murugavel; P S Kannan; A SubbiahPandi; Ramalingam Murugan; S SrimanNarayanan

doi:10.1107/S1600536808034028

. 2008 Oct 25;64(Pt 11):o2194. doi: 10.1107/S1600536808034028

(Z)-3-(4-Fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-2-tosylprop-2-en-1-one

S Murugavel ^a, P S Kannan ^b, A SubbiahPandi ^c,^*, Ramalingam Murugan ^d, S SrimanNarayanan ^d

PMCID: PMC2959516 PMID: 21581052

Abstract

In the title compound, C₂₃H₁₉FO₅S₂, two of the phenyl ring C atoms and a sulfonyl O atom of the phenyl(methylsulfonyl) group are disordered over two positions with occupancies 0.522 (17):0.478 (17). The methylphenyl and fluorophenyl rings are essentially planar, with maximum deviations of 0.0059 (8) and 0.0047 (9) Å, respectively. The crystal packing is stabilized by C—H⋯F interactions.

Related literature

For details of the pharmacological activity, see: Turner (2002 ▶); Supuran & Scozzafava (2003 ▶); Masereel et al. (2002 ▶); Pellis & West (1968 ▶); Cohen et al. (1977 ▶); Csaszar & Morvay (1983 ▶); Lakshmi et al. (1985 ▶); El-Maghraby et al. (1984 ▶); Dzhurayev et al. (1992 ▶); Gewald et al. (1966 ▶).

Experimental

Crystal data

C₂₃H₁₉FO₅S₂
M _r = 458.52
Monoclinic,
a = 9.6962 (7) Å
b = 22.8539 (16) Å
c = 10.8217 (7) Å
β = 109.672 (2)°
V = 2258.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 (2) K
0.26 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
21889 measured reflections
3994 independent reflections
2543 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.241
S = 1.01
3994 reflections
293 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034028/fl2219sup1.cif

e-64-o2194-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034028/fl2219Isup2.hkl

e-64-o2194-Isup2.hkl^{(191.8KB, 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
C19—H19⋯Fⁱ	0.93	2.37	3.274 (8)	167

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Symmetry code: (i) Inline graphic .

Acknowledgments

SM and ASP thank Dr S. Pandi, Head of the Department of Physics, Presidency College (Autonomous), Chennai, for providing the necessary facilities; they also thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with collecting the X-ray intensity data.

supplementary crystallographic information

Comment

Sulfonamides are an important class of drugs which are known for their pharmacological activities, e.g., anti-microbial and anti-HIV (Turner, 2002), insulin-releasing anti-diabetic, carbonic anhydrase inhibition (Supuran & Scozzafava, 2003), high ceiling diuretic, anti-thyroid and anti-tumor (Masereel et al., 2002). Some sulfur containing Schiff bases [Pellis & West, 1968; Cohen et al., 1977; Csaszar & Morvay,1983; Lakshmi et al., 1985], and their thiophene derivatives [El-Maghraby et al., 1984; Dzhurayev et al., 1992], exhibit anti-bacterial, anti-cancer, anti-inflammatory and anti-toxic pharmacological activity [Gewald et al., 1966]. 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 F atom deviates by -0.027 (4)Å from the least-squares of the plane of ring B. Atoms O2, C6 and C7 are disordered with a ration of 47:52 (Fig 1). The methylphenyl and fluorophenyl rings are essentially planar, with maximum deviations of 0.0059 (8) and 0.0047 (9) Å, respectively.

Atom C19 (x, y, z) donates a proton to the F atom in a neighboring molecule (3/2 - x, -1/2 + y, -1/2 + z) forming a linear chain along the a axis. In addition to Van der Waals interactions, the crystal packing is stabilized by this C–H···F interaction.

Experimental

1.0 mol of 1-(4-(methylsulfonyl)phenyl)-2-tosylethanone(0.5 g), 1.0 mol of 4-fluorobenzaldehyde(0.18 g) and the sodium hydroxide(0.06 g) was allowed to stir overnight at room temperature to get the title compound. The crude product was filtered and then recrystallized by slow evaporation from chloroform: methanol [9:1] to give the single crystals used for data collection.