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

Murugavel, S.; Kannan, P.S.; SubbiahPandi, A.; Murugan, R.; SrimanNarayanan, S.

doi:10.1107/S1600536808034028

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2194

doi:10.1107/S1600536808034028

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(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 and S. SrimanNarayanan ^d

^aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, ^bDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^dDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 14 August 2008; accepted 17 October 2008; online 25 October 2008)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.067
wR(F²) = 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

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
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

For related literature on 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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of title compound showing 30% probability displacement ellipsoids. The disordered components are shown.

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

Crystal data top

C₂₃H₁₉FO₅S₂	F(000) = 952
M_r = 458.52	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3994 reflections
a = 9.6962 (7) Å	θ = 1.8–25.1°
b = 22.8539 (16) Å	µ = 0.28 mm⁻¹
c = 10.8217 (7) Å	T = 293 K
β = 109.672 (2)°	Block, colourless
V = 2258.1 (3) Å³	0.26 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.1°, θ_min = 1.8°
ω and ϕ scans	h = −11→10
21889 measured reflections	k = −27→27
3994 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.241	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1393P)² + 1.1164P] where P = (F_o² + 2F_c²)/3
3994 reflections	(Δ/σ)_max = 0.015
293 parameters	Δρ_max = 0.57 e Å⁻³
4 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₃H₁₉FO₅S₂	V = 2258.1 (3) Å³
M_r = 458.52	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6962 (7) Å	µ = 0.28 mm⁻¹
b = 22.8539 (16) Å	T = 293 K
c = 10.8217 (7) Å	0.26 × 0.15 × 0.15 mm
β = 109.672 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2543 reflections with I > 2σ(I)
21889 measured reflections	R_int = 0.029
3994 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	4 restraints
wR(F²) = 0.241	H-atom parameters constrained
S = 1.01	Δρ_max = 0.57 e Å⁻³
3994 reflections	Δρ_min = −0.25 e Å⁻³
293 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.3723 (4)	0.4255 (2)	−0.0871 (5)	0.0930 (14)
H1A	1.3540	0.4621	−0.1335	0.139*
H1B	1.3282	0.3943	−0.1466	0.139*
H1C	1.4760	0.4191	−0.0502	0.139*
C2	1.1672 (4)	0.3762 (2)	−0.0248 (4)	0.0890 (13)
C3	1.1626 (4)	0.33042 (19)	−0.1075 (4)	0.0806 (11)
H3	1.2361	0.3260	−0.1441	0.097*
C4	1.0497 (4)	0.29108 (18)	−0.1363 (4)	0.0769 (11)
H4	1.0475	0.2598	−0.1918	0.092*
C5	0.9391 (4)	0.29742 (17)	−0.0836 (3)	0.0679 (10)
C6A	0.932 (2)	0.3505 (5)	−0.0214 (16)	0.088 (5)	0.522 (17)
H6A	0.8507	0.3582	0.0025	0.105*	0.522 (17)
C6B	0.957 (2)	0.3373 (7)	0.0188 (16)	0.088 (5)	0.478 (17)
H6B	0.8912	0.3383	0.0641	0.105*	0.478 (17)
C7A	1.0415 (11)	0.3915 (9)	0.0058 (15)	0.089 (4)	0.522 (17)
H7A	1.0331	0.4276	0.0425	0.107*	0.522 (17)
C7B	1.0744 (16)	0.3748 (10)	0.0514 (15)	0.089 (4)	0.478 (17)
H7B	1.0927	0.3993	0.1237	0.107*	0.478 (17)
C8	0.8192 (4)	0.25372 (19)	−0.1142 (3)	0.0698 (10)
C9	0.6772 (4)	0.27111 (17)	−0.0973 (3)	0.0666 (9)
C10	0.5902 (4)	0.31364 (17)	−0.1618 (4)	0.0702 (10)
H10	0.5098	0.3228	−0.1370	0.084*
C11	0.6107 (4)	0.34758 (16)	−0.2697 (4)	0.0669 (9)
C12	0.5815 (6)	0.4061 (2)	−0.2782 (5)	0.1029 (16)
H12	0.5487	0.4239	−0.2158	0.123*
C13	0.5997 (7)	0.4391 (2)	−0.3770 (6)	0.127 (2)
H13	0.5812	0.4792	−0.3816	0.153*
C14	0.6457 (6)	0.4119 (2)	−0.4688 (4)	0.0942 (14)
C15	0.6751 (5)	0.3547 (2)	−0.4645 (4)	0.0861 (12)
H15	0.7066	0.3373	−0.5280	0.103*
C16	0.6576 (5)	0.32188 (17)	−0.3637 (4)	0.0773 (11)
H16	0.6776	0.2820	−0.3592	0.093*
C17	0.5859 (5)	0.1628 (2)	−0.0386 (4)	0.0824 (12)
C18	0.6805 (8)	0.1184 (3)	0.0090 (6)	0.132 (2)
H18	0.7669	0.1254	0.0781	0.159*
C23	0.4581 (5)	0.1538 (3)	−0.1417 (5)	0.1033 (16)
H23	0.3927	0.1842	−0.1762	0.124*
O1	1.4436 (7)	0.3984 (4)	0.1553 (7)	0.261 (4)
O2A	1.268 (4)	0.4774 (8)	0.071 (3)	0.137 (6)	0.522 (17)
O2B	1.255 (5)	0.4845 (8)	0.021 (3)	0.137 (6)	0.478 (17)
O3	0.8339 (3)	0.20504 (15)	−0.1523 (4)	0.1011 (10)
O4	0.7600 (3)	0.22936 (15)	0.1392 (3)	0.0991 (10)
O5	0.5023 (4)	0.25992 (15)	0.0377 (3)	0.1033 (10)
S1	1.31187 (15)	0.42709 (8)	0.01374 (16)	0.1220 (6)
S2	0.63094 (12)	0.23274 (5)	0.02559 (10)	0.0801 (4)
F	0.6602 (4)	0.44442 (14)	−0.5693 (3)	0.1362 (12)
C22	0.4298 (7)	0.0953 (4)	−0.1942 (6)	0.128 (2)
H22	0.3440	0.0871	−0.2630	0.154*
C20	0.5310 (10)	0.0515 (3)	−0.1415 (8)	0.135 (2)
C19	0.6521 (10)	0.0637 (3)	−0.0419 (8)	0.166 (3)
H19	0.7192	0.0339	−0.0063	0.199*
C21	0.4865 (13)	−0.0082 (4)	−0.2075 (9)	0.228 (5)
H21A	0.5557	−0.0199	−0.2486	0.342*
H21B	0.3907	−0.0054	−0.2725	0.342*
H21C	0.4852	−0.0366	−0.1426	0.342*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.067 (3)	0.122 (3)	0.112 (3)	−0.040 (2)	0.059 (2)	−0.043 (3)
C2	0.060 (2)	0.139 (4)	0.075 (3)	−0.012 (2)	0.032 (2)	−0.029 (2)
C3	0.062 (2)	0.106 (3)	0.086 (3)	0.002 (2)	0.041 (2)	−0.014 (2)
C4	0.068 (2)	0.090 (3)	0.083 (3)	0.011 (2)	0.037 (2)	−0.009 (2)
C5	0.056 (2)	0.098 (3)	0.0552 (19)	0.0054 (19)	0.0253 (16)	−0.0033 (18)
C6A	0.060 (6)	0.161 (7)	0.052 (9)	−0.017 (5)	0.031 (7)	−0.030 (7)
C6B	0.060 (6)	0.161 (7)	0.052 (9)	−0.017 (5)	0.031 (7)	−0.030 (7)
C7A	0.064 (5)	0.143 (11)	0.062 (8)	−0.010 (5)	0.024 (6)	−0.038 (7)
C7B	0.064 (5)	0.143 (11)	0.062 (8)	−0.010 (5)	0.024 (6)	−0.038 (7)
C8	0.071 (2)	0.084 (3)	0.060 (2)	0.010 (2)	0.0291 (18)	0.0063 (18)
C9	0.057 (2)	0.084 (2)	0.062 (2)	0.0006 (18)	0.0245 (16)	0.0043 (17)
C10	0.055 (2)	0.086 (2)	0.074 (2)	0.0004 (18)	0.0274 (17)	0.0023 (19)
C11	0.055 (2)	0.074 (2)	0.073 (2)	−0.0010 (17)	0.0243 (17)	0.0036 (17)
C12	0.130 (4)	0.087 (3)	0.123 (4)	0.028 (3)	0.084 (3)	0.020 (3)
C13	0.186 (6)	0.079 (3)	0.157 (5)	0.030 (3)	0.112 (5)	0.030 (3)
C14	0.112 (4)	0.091 (3)	0.088 (3)	−0.005 (3)	0.044 (3)	0.020 (2)
C15	0.105 (3)	0.090 (3)	0.070 (2)	−0.006 (2)	0.038 (2)	−0.005 (2)
C16	0.096 (3)	0.072 (2)	0.064 (2)	−0.003 (2)	0.028 (2)	−0.0008 (17)
C17	0.079 (3)	0.105 (3)	0.069 (2)	−0.008 (2)	0.032 (2)	0.019 (2)
C18	0.146 (5)	0.101 (4)	0.124 (5)	0.006 (4)	0.012 (4)	0.011 (3)
C23	0.082 (3)	0.150 (5)	0.082 (3)	−0.023 (3)	0.033 (2)	0.021 (3)
O1	0.138 (4)	0.415 (12)	0.189 (6)	−0.047 (6)	−0.001 (4)	−0.062 (7)
O2A	0.118 (7)	0.170 (5)	0.147 (18)	−0.055 (4)	0.076 (14)	−0.082 (7)
O2B	0.118 (7)	0.170 (5)	0.147 (18)	−0.055 (4)	0.076 (14)	−0.082 (7)
O3	0.095 (2)	0.092 (2)	0.133 (3)	0.0088 (17)	0.060 (2)	0.0008 (19)
O4	0.094 (2)	0.130 (3)	0.0670 (18)	0.0013 (18)	0.0190 (15)	0.0136 (16)
O5	0.101 (2)	0.131 (3)	0.102 (2)	0.0228 (19)	0.067 (2)	0.0240 (18)
S1	0.0773 (8)	0.1712 (15)	0.1302 (12)	−0.0381 (8)	0.0517 (8)	−0.0670 (10)
S2	0.0759 (7)	0.1063 (9)	0.0653 (6)	0.0055 (5)	0.0333 (5)	0.0160 (5)
F	0.190 (3)	0.118 (2)	0.125 (2)	−0.002 (2)	0.086 (2)	0.0390 (18)
C22	0.121 (5)	0.187 (7)	0.082 (3)	−0.064 (5)	0.042 (3)	−0.007 (4)
C20	0.170 (7)	0.125 (5)	0.122 (5)	−0.025 (5)	0.066 (5)	0.013 (4)
C19	0.189 (8)	0.121 (6)	0.151 (6)	0.002 (5)	0.008 (6)	0.005 (5)
C21	0.352 (15)	0.160 (7)	0.196 (9)	−0.102 (9)	0.123 (10)	−0.057 (6)

Geometric parameters (Å, º) top

C1—S1	1.402 (4)	C12—C13	1.368 (7)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.369 (7)
C1—H1C	0.9600	C13—H13	0.9300
C2—C3	1.368 (6)	C14—C15	1.336 (6)
C2—C7B	1.410 (6)	C14—F	1.363 (5)
C2—C7A	1.411 (6)	C15—C16	1.380 (5)
C2—S1	1.761 (5)	C15—H15	0.9300
C3—C4	1.369 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.350 (7)
C4—C5	1.381 (5)	C17—C23	1.375 (6)
C4—H4	0.9300	C17—S2	1.738 (5)
C5—C6B	1.399 (7)	C18—C19	1.357 (9)
C5—C6A	1.399 (7)	C18—H18	0.9300
C5—C8	1.483 (6)	C23—C22	1.443 (8)
C6A—C7A	1.370 (7)	C23—H23	0.9300
C6A—H6A	0.9300	O1—S1	1.758 (7)
C6B—C7B	1.370 (7)	O2A—S1	1.435 (6)
C6B—H6B	0.9300	O2B—S1	1.435 (6)
C7A—H7A	0.9300	O4—S2	1.431 (3)
C7B—H7B	0.9300	O5—S2	1.438 (3)
C8—O3	1.211 (5)	C22—C20	1.383 (10)
C8—C9	1.503 (5)	C22—H22	0.9300
C9—C10	1.322 (5)	C20—C19	1.329 (10)
C9—S2	1.772 (4)	C20—C21	1.532 (10)
C10—C11	1.469 (5)	C19—H19	0.9300
C10—H10	0.9300	C21—H21A	0.9600
C11—C16	1.377 (5)	C21—H21B	0.9600
C11—C12	1.364 (6)	C21—H21C	0.9600

S1—C1—H1A	109.5	C12—C13—H13	120.8
S1—C1—H1B	109.5	C14—C13—H13	120.8
H1A—C1—H1B	109.5	C15—C14—F	118.9 (4)
S1—C1—H1C	109.5	C15—C14—C13	122.5 (4)
H1A—C1—H1C	109.5	F—C14—C13	118.6 (5)
H1B—C1—H1C	109.5	C14—C15—C16	118.6 (4)
C3—C2—C7B	118.5 (10)	C14—C15—H15	120.7
C3—C2—C7A	120.2 (8)	C16—C15—H15	120.7
C3—C2—S1	120.6 (3)	C11—C16—C15	120.7 (4)
C7B—C2—S1	119.4 (9)	C11—C16—H16	119.6
C7A—C2—S1	117.6 (9)	C15—C16—H16	119.6
C2—C3—C4	119.9 (4)	C18—C17—C23	120.5 (5)
C2—C3—H3	120.0	C18—C17—S2	119.5 (4)
C4—C3—H3	120.0	C23—C17—S2	119.9 (4)
C5—C4—C3	120.6 (4)	C17—C18—C19	121.3 (6)
C5—C4—H4	119.7	C17—C18—H18	119.3
C3—C4—H4	119.7	C19—C18—H18	119.3
C4—C5—C6B	119.1 (9)	C17—C23—C22	117.3 (5)
C4—C5—C6A	117.2 (9)	C17—C23—H23	121.3
C4—C5—C8	119.8 (3)	C22—C23—H23	121.3
C6B—C5—C8	119.8 (9)	C1—S1—O2B	109.6 (12)
C6A—C5—C8	122.1 (8)	C1—S1—O2A	128.1 (12)
C7A—C6A—C5	122.7 (16)	C1—S1—O1	107.3 (3)
C7A—C6A—H6A	118.6	O2B—S1—O1	118.3 (14)
C5—C6A—H6A	118.6	O2A—S1—O1	99.0 (12)
C7B—C6B—C5	119.0 (17)	C1—S1—C2	107.9 (2)
C7B—C6B—H6B	120.5	O2B—S1—C2	109.0 (18)
C5—C6B—H6B	120.5	O2A—S1—C2	107.7 (16)
C6A—C7A—C2	116.4 (17)	O1—S1—C2	104.3 (3)
C6A—C7A—H7A	121.8	O5—S2—O4	118.6 (2)
C2—C7A—H7A	121.8	O5—S2—C17	108.9 (2)
C6B—C7B—C2	120.0 (17)	O4—S2—C17	108.9 (2)
C6B—C7B—H7B	120.0	O5—S2—C9	107.52 (18)
C2—C7B—H7B	120.0	O4—S2—C9	107.61 (18)
O3—C8—C5	121.4 (4)	C17—S2—C9	104.35 (18)
O3—C8—C9	120.1 (4)	C20—C22—C23	119.6 (6)
C5—C8—C9	118.4 (3)	C20—C22—H22	120.2
C10—C9—C8	125.3 (3)	C23—C22—H22	120.2
C10—C9—S2	118.9 (3)	C19—C20—C22	119.6 (7)
C8—C9—S2	115.8 (3)	C19—C20—C21	126.6 (9)
C9—C10—C11	125.1 (3)	C22—C20—C21	113.7 (8)
C9—C10—H10	117.4	C20—C19—C18	121.7 (8)
C11—C10—H10	117.4	C20—C19—H19	119.2
C16—C11—C12	118.7 (4)	C18—C19—H19	119.2
C16—C11—C10	121.9 (3)	C20—C21—H21A	109.5
C12—C11—C10	119.4 (4)	C20—C21—H21B	109.5
C13—C12—C11	121.0 (4)	H21A—C21—H21B	109.5
C13—C12—H12	119.5	C20—C21—H21C	109.5
C11—C12—H12	119.5	H21A—C21—H21C	109.5
C12—C13—C14	118.5 (5)	H21B—C21—H21C	109.5

C7B—C2—C3—C4	13.9 (11)	F—C14—C15—C16	−178.9 (4)
C7A—C2—C3—C4	−15.3 (11)	C13—C14—C15—C16	0.3 (8)
S1—C2—C3—C4	179.8 (4)	C12—C11—C16—C15	0.2 (6)
C2—C3—C4—C5	0.6 (7)	C10—C11—C16—C15	179.6 (4)
C3—C4—C5—C6B	−12.5 (12)	C14—C15—C16—C11	0.1 (7)
C3—C4—C5—C6A	11.7 (10)	C23—C17—C18—C19	−0.7 (10)
C3—C4—C5—C8	−178.9 (4)	S2—C17—C18—C19	−177.4 (6)
C4—C5—C6A—C7A	−9.9 (17)	C18—C17—C23—C22	0.9 (7)
C6B—C5—C6A—C7A	91 (5)	S2—C17—C23—C22	177.5 (3)
C8—C5—C6A—C7A	−179.1 (10)	C3—C2—S1—C1	23.0 (5)
C4—C5—C6B—C7B	9 (2)	C7B—C2—S1—C1	−171.3 (10)
C6A—C5—C6B—C7B	−82 (4)	C7A—C2—S1—C1	−142.3 (9)
C8—C5—C6B—C7B	175.7 (12)	C3—C2—S1—O2B	141.9 (12)
C5—C6A—C7A—C2	−3.9 (18)	C7B—C2—S1—O2B	−52.4 (17)
C3—C2—C7A—C6A	16.6 (15)	C7A—C2—S1—O2B	−23.4 (16)
C7B—C2—C7A—C6A	−77 (4)	C3—C2—S1—O2A	164.5 (12)
S1—C2—C7A—C6A	−178.0 (9)	C7B—C2—S1—O2A	−29.7 (17)
C5—C6B—C7B—C2	5 (2)	C7A—C2—S1—O2A	−0.8 (16)
C3—C2—C7B—C6B	−17.0 (19)	C3—C2—S1—O1	−90.9 (5)
C7A—C2—C7B—C6B	84 (3)	C7B—C2—S1—O1	74.9 (11)
S1—C2—C7B—C6B	177.0 (12)	C7A—C2—S1—O1	103.8 (9)
C4—C5—C8—O3	20.9 (6)	C18—C17—S2—O5	−139.9 (4)
C6B—C5—C8—O3	−145.5 (11)	C23—C17—S2—O5	43.5 (4)
C6A—C5—C8—O3	−170.3 (10)	C18—C17—S2—O4	−9.1 (5)
C4—C5—C8—C9	−159.0 (3)	C23—C17—S2—O4	174.2 (3)
C6B—C5—C8—C9	34.6 (12)	C18—C17—S2—C9	105.5 (4)
C6A—C5—C8—C9	9.9 (10)	C23—C17—S2—C9	−71.1 (4)
O3—C8—C9—C10	−118.1 (5)	C10—C9—S2—O5	−3.8 (4)
C5—C8—C9—C10	61.7 (5)	C8—C9—S2—O5	173.3 (3)
O3—C8—C9—S2	65.0 (4)	C10—C9—S2—O4	−132.6 (3)
C5—C8—C9—S2	−115.1 (3)	C8—C9—S2—O4	44.4 (3)
C8—C9—C10—C11	6.0 (6)	C10—C9—S2—C17	111.8 (3)
S2—C9—C10—C11	−177.3 (3)	C8—C9—S2—C17	−71.1 (3)
C9—C10—C11—C16	39.3 (6)	C17—C23—C22—C20	−1.0 (7)
C9—C10—C11—C12	−141.2 (5)	C23—C22—C20—C19	1.0 (10)
C16—C11—C12—C13	−0.7 (8)	C23—C22—C20—C21	−179.7 (5)
C10—C11—C12—C13	179.8 (5)	C22—C20—C19—C18	−0.8 (12)
C11—C12—C13—C14	1.1 (10)	C21—C20—C19—C18	180.0 (8)
C12—C13—C14—C15	−0.8 (9)	C17—C18—C19—C20	0.6 (13)
C12—C13—C14—F	178.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Fⁱ	0.93	2.37	3.274 (8)	167

Symmetry code: (i) −x+3/2, y−1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉FO₅S₂
M_r	458.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.6962 (7), 22.8539 (16), 10.8217 (7)
β (°)	109.672 (2)
V (Å³)	2258.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.26 × 0.15 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21889, 3994, 2543
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.241, 1.01
No. of reflections	3994
No. of parameters	293
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Fⁱ	0.93	2.37	3.274 (8)	167.4

Symmetry code: (i) −x+3/2, y−1/2, −z−1/2.

Acknowledgements

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.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cohen, V. I., Rist, N. & Duponchel, C. (1977). J. Pharm. Sci. 66, 1322–1334. PubMed Web of Science Google Scholar
Csaszar, J. & Morvay, J. (1983). Acta Pharm. Hung. 53, 121–128. CAS PubMed Google Scholar
Dzhurayev, A. D., Karimkulov, K. M., Makhsumov, A. G. & Amanov, N. (1992). Khim. Farm. Zh. 26, 73–75. CAS Google Scholar
El-Maghraby, A. A., Haroun, B. & Mohammed, N. A. (1984). Egypt. J. Pharm. Sci. 23, 327–336. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gewald, K., Schinke, E. & Botcher, H. (1966). Chem. Ber. 99, 99–100. Google Scholar
Lakshmi, V. V., Sridhar, P. & Polasa, H. (1985). Indian J. Pharm. Sci. 47, 202–204. CAS Google Scholar
Masereel, S., Abbate, R. F., Scozzafava, A. & Supuran, C. T. (2002). J. Med. Chem. 45, 312–320. Web of Science CrossRef PubMed CAS Google Scholar
Pellis, G. & West, G. B. (1968). Progress in Medicinal Chemistry, Vol. 5, pp. 320–324. London: Butterworth & Co. Ltd. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Supuran, C. T. & Scozzafava, A. (2003). Med. Res. Rev. 15, 146–149. Web of Science CrossRef Google Scholar
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Volume 64| Part 11| November 2008| Page o2194

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

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