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ISSN: 2056-9890

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

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[Turner, S. R. (2002). Curr. Med. Chem. Anti-Infective Agent, 1, 141-162.]); Supuran & Scozzafava (2003[Supuran, C. T. & Scozzafava, A. (2003). Med. Res. Rev. 15, 146-149.]); Masereel et al. (2002[Masereel, S., Abbate, R. F., Scozzafava, A. & Supuran, C. T. (2002). J. Med. Chem. 45, 312-320.]); Pellis & West (1968[Pellis, G. & West, G. B. (1968). Progress in Medicinal Chemistry, Vol. 5, pp. 320-324. London: Butterworth & Co. Ltd.]); Cohen et al. (1977[Cohen, V. I., Rist, N. & Duponchel, C. (1977). J. Pharm. Sci. 66, 1322-1334.]); Csaszar & Morvay (1983[Csaszar, J. & Morvay, J. (1983). Acta Pharm. Hung. 53, 121-128.]); Lakshmi et al. (1985[Lakshmi, V. V., Sridhar, P. & Polasa, H. (1985). Indian J. Pharm. Sci. 47, 202-204.]); El-Maghraby et al. (1984[El-Maghraby, A. A., Haroun, B. & Mohammed, N. A. (1984). Egypt. J. Pharm. Sci. 23, 327-336.]); Dzhurayev et al. (1992[Dzhurayev, A. D., Karimkulov, K. M., Makhsumov, A. G. & Amanov, N. (1992). Khim. Farm. Zh. 26, 73-75.]); Gewald et al. (1966[Gewald, K., Schinke, E. & Botcher, H. (1966). Chem. Ber. 99, 99-100.]).

[Scheme 1]

Experimental

Crystal data
  • C23H19FO5S2

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


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.

Refinement top

The corresponding bond distances involving the disordered atoms were restrained to be equal, and also the same Uij parameters were used for atoms O2A and O2B, C6A and C6B, and C7A and C7B. H atoms were positioned geomentrically (C–H = 0.93Å or 0.97 Å) and were treated as riding on their parent atoms, with Uiso(H)=1.2Ueq(C).

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
[Figure 1] 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
C23H19FO5S2F(000) = 952
Mr = 458.52Dx = 1.349 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3994 reflections
a = 9.6962 (7) Åθ = 1.8–25.1°
b = 22.8539 (16) ŵ = 0.28 mm1
c = 10.8217 (7) ÅT = 293 K
β = 109.672 (2)°Block, colourless
V = 2258.1 (3) Å30.26 × 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 tubeRint = 0.029
Graphite monochromatorθmax = 25.1°, θmin = 1.8°
ω and ϕ scansh = 1110
21889 measured reflectionsk = 2727
3994 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1393P)2 + 1.1164P]
where P = (Fo2 + 2Fc2)/3
3994 reflections(Δ/σ)max = 0.015
293 parametersΔρmax = 0.57 e Å3
4 restraintsΔρmin = 0.25 e Å3
Crystal data top
C23H19FO5S2V = 2258.1 (3) Å3
Mr = 458.52Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6962 (7) ŵ = 0.28 mm1
b = 22.8539 (16) ÅT = 293 K
c = 10.8217 (7) Å0.26 × 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 reflectionsRint = 0.029
3994 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0674 restraints
wR(F2) = 0.241H-atom parameters constrained
S = 1.01Δρmax = 0.57 e Å3
3994 reflectionsΔρmin = 0.25 e Å3
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
xyzUiso*/UeqOcc. (<1)
C11.3723 (4)0.4255 (2)0.0871 (5)0.0930 (14)
H1A1.35400.46210.13350.139*
H1B1.32820.39430.14660.139*
H1C1.47600.41910.05020.139*
C21.1672 (4)0.3762 (2)0.0248 (4)0.0890 (13)
C31.1626 (4)0.33042 (19)0.1075 (4)0.0806 (11)
H31.23610.32600.14410.097*
C41.0497 (4)0.29108 (18)0.1363 (4)0.0769 (11)
H41.04750.25980.19180.092*
C50.9391 (4)0.29742 (17)0.0836 (3)0.0679 (10)
C6A0.932 (2)0.3505 (5)0.0214 (16)0.088 (5)0.522 (17)
H6A0.85070.35820.00250.105*0.522 (17)
C6B0.957 (2)0.3373 (7)0.0188 (16)0.088 (5)0.478 (17)
H6B0.89120.33830.06410.105*0.478 (17)
C7A1.0415 (11)0.3915 (9)0.0058 (15)0.089 (4)0.522 (17)
H7A1.03310.42760.04250.107*0.522 (17)
C7B1.0744 (16)0.3748 (10)0.0514 (15)0.089 (4)0.478 (17)
H7B1.09270.39930.12370.107*0.478 (17)
C80.8192 (4)0.25372 (19)0.1142 (3)0.0698 (10)
C90.6772 (4)0.27111 (17)0.0973 (3)0.0666 (9)
C100.5902 (4)0.31364 (17)0.1618 (4)0.0702 (10)
H100.50980.32280.13700.084*
C110.6107 (4)0.34758 (16)0.2697 (4)0.0669 (9)
C120.5815 (6)0.4061 (2)0.2782 (5)0.1029 (16)
H120.54870.42390.21580.123*
C130.5997 (7)0.4391 (2)0.3770 (6)0.127 (2)
H130.58120.47920.38160.153*
C140.6457 (6)0.4119 (2)0.4688 (4)0.0942 (14)
C150.6751 (5)0.3547 (2)0.4645 (4)0.0861 (12)
H150.70660.33730.52800.103*
C160.6576 (5)0.32188 (17)0.3637 (4)0.0773 (11)
H160.67760.28200.35920.093*
C170.5859 (5)0.1628 (2)0.0386 (4)0.0824 (12)
C180.6805 (8)0.1184 (3)0.0090 (6)0.132 (2)
H180.76690.12540.07810.159*
C230.4581 (5)0.1538 (3)0.1417 (5)0.1033 (16)
H230.39270.18420.17620.124*
O11.4436 (7)0.3984 (4)0.1553 (7)0.261 (4)
O2A1.268 (4)0.4774 (8)0.071 (3)0.137 (6)0.522 (17)
O2B1.255 (5)0.4845 (8)0.021 (3)0.137 (6)0.478 (17)
O30.8339 (3)0.20504 (15)0.1523 (4)0.1011 (10)
O40.7600 (3)0.22936 (15)0.1392 (3)0.0991 (10)
O50.5023 (4)0.25992 (15)0.0377 (3)0.1033 (10)
S11.31187 (15)0.42709 (8)0.01374 (16)0.1220 (6)
S20.63094 (12)0.23274 (5)0.02559 (10)0.0801 (4)
F0.6602 (4)0.44442 (14)0.5693 (3)0.1362 (12)
C220.4298 (7)0.0953 (4)0.1942 (6)0.128 (2)
H220.34400.08710.26300.154*
C200.5310 (10)0.0515 (3)0.1415 (8)0.135 (2)
C190.6521 (10)0.0637 (3)0.0419 (8)0.166 (3)
H190.71920.03390.00630.199*
C210.4865 (13)0.0082 (4)0.2075 (9)0.228 (5)
H21A0.55570.01990.24860.342*
H21B0.39070.00540.27250.342*
H21C0.48520.03660.14260.342*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.067 (3)0.122 (3)0.112 (3)0.040 (2)0.059 (2)0.043 (3)
C20.060 (2)0.139 (4)0.075 (3)0.012 (2)0.032 (2)0.029 (2)
C30.062 (2)0.106 (3)0.086 (3)0.002 (2)0.041 (2)0.014 (2)
C40.068 (2)0.090 (3)0.083 (3)0.011 (2)0.037 (2)0.009 (2)
C50.056 (2)0.098 (3)0.0552 (19)0.0054 (19)0.0253 (16)0.0033 (18)
C6A0.060 (6)0.161 (7)0.052 (9)0.017 (5)0.031 (7)0.030 (7)
C6B0.060 (6)0.161 (7)0.052 (9)0.017 (5)0.031 (7)0.030 (7)
C7A0.064 (5)0.143 (11)0.062 (8)0.010 (5)0.024 (6)0.038 (7)
C7B0.064 (5)0.143 (11)0.062 (8)0.010 (5)0.024 (6)0.038 (7)
C80.071 (2)0.084 (3)0.060 (2)0.010 (2)0.0291 (18)0.0063 (18)
C90.057 (2)0.084 (2)0.062 (2)0.0006 (18)0.0245 (16)0.0043 (17)
C100.055 (2)0.086 (2)0.074 (2)0.0004 (18)0.0274 (17)0.0023 (19)
C110.055 (2)0.074 (2)0.073 (2)0.0010 (17)0.0243 (17)0.0036 (17)
C120.130 (4)0.087 (3)0.123 (4)0.028 (3)0.084 (3)0.020 (3)
C130.186 (6)0.079 (3)0.157 (5)0.030 (3)0.112 (5)0.030 (3)
C140.112 (4)0.091 (3)0.088 (3)0.005 (3)0.044 (3)0.020 (2)
C150.105 (3)0.090 (3)0.070 (2)0.006 (2)0.038 (2)0.005 (2)
C160.096 (3)0.072 (2)0.064 (2)0.003 (2)0.028 (2)0.0008 (17)
C170.079 (3)0.105 (3)0.069 (2)0.008 (2)0.032 (2)0.019 (2)
C180.146 (5)0.101 (4)0.124 (5)0.006 (4)0.012 (4)0.011 (3)
C230.082 (3)0.150 (5)0.082 (3)0.023 (3)0.033 (2)0.021 (3)
O10.138 (4)0.415 (12)0.189 (6)0.047 (6)0.001 (4)0.062 (7)
O2A0.118 (7)0.170 (5)0.147 (18)0.055 (4)0.076 (14)0.082 (7)
O2B0.118 (7)0.170 (5)0.147 (18)0.055 (4)0.076 (14)0.082 (7)
O30.095 (2)0.092 (2)0.133 (3)0.0088 (17)0.060 (2)0.0008 (19)
O40.094 (2)0.130 (3)0.0670 (18)0.0013 (18)0.0190 (15)0.0136 (16)
O50.101 (2)0.131 (3)0.102 (2)0.0228 (19)0.067 (2)0.0240 (18)
S10.0773 (8)0.1712 (15)0.1302 (12)0.0381 (8)0.0517 (8)0.0670 (10)
S20.0759 (7)0.1063 (9)0.0653 (6)0.0055 (5)0.0333 (5)0.0160 (5)
F0.190 (3)0.118 (2)0.125 (2)0.002 (2)0.086 (2)0.0390 (18)
C220.121 (5)0.187 (7)0.082 (3)0.064 (5)0.042 (3)0.007 (4)
C200.170 (7)0.125 (5)0.122 (5)0.025 (5)0.066 (5)0.013 (4)
C190.189 (8)0.121 (6)0.151 (6)0.002 (5)0.008 (6)0.005 (5)
C210.352 (15)0.160 (7)0.196 (9)0.102 (9)0.123 (10)0.057 (6)
Geometric parameters (Å, º) top
C1—S11.402 (4)C12—C131.368 (7)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600C13—C141.369 (7)
C1—H1C0.9600C13—H130.9300
C2—C31.368 (6)C14—C151.336 (6)
C2—C7B1.410 (6)C14—F1.363 (5)
C2—C7A1.411 (6)C15—C161.380 (5)
C2—S11.761 (5)C15—H150.9300
C3—C41.369 (6)C16—H160.9300
C3—H30.9300C17—C181.350 (7)
C4—C51.381 (5)C17—C231.375 (6)
C4—H40.9300C17—S21.738 (5)
C5—C6B1.399 (7)C18—C191.357 (9)
C5—C6A1.399 (7)C18—H180.9300
C5—C81.483 (6)C23—C221.443 (8)
C6A—C7A1.370 (7)C23—H230.9300
C6A—H6A0.9300O1—S11.758 (7)
C6B—C7B1.370 (7)O2A—S11.435 (6)
C6B—H6B0.9300O2B—S11.435 (6)
C7A—H7A0.9300O4—S21.431 (3)
C7B—H7B0.9300O5—S21.438 (3)
C8—O31.211 (5)C22—C201.383 (10)
C8—C91.503 (5)C22—H220.9300
C9—C101.322 (5)C20—C191.329 (10)
C9—S21.772 (4)C20—C211.532 (10)
C10—C111.469 (5)C19—H190.9300
C10—H100.9300C21—H21A0.9600
C11—C161.377 (5)C21—H21B0.9600
C11—C121.364 (6)C21—H21C0.9600
S1—C1—H1A109.5C12—C13—H13120.8
S1—C1—H1B109.5C14—C13—H13120.8
H1A—C1—H1B109.5C15—C14—F118.9 (4)
S1—C1—H1C109.5C15—C14—C13122.5 (4)
H1A—C1—H1C109.5F—C14—C13118.6 (5)
H1B—C1—H1C109.5C14—C15—C16118.6 (4)
C3—C2—C7B118.5 (10)C14—C15—H15120.7
C3—C2—C7A120.2 (8)C16—C15—H15120.7
C3—C2—S1120.6 (3)C11—C16—C15120.7 (4)
C7B—C2—S1119.4 (9)C11—C16—H16119.6
C7A—C2—S1117.6 (9)C15—C16—H16119.6
C2—C3—C4119.9 (4)C18—C17—C23120.5 (5)
C2—C3—H3120.0C18—C17—S2119.5 (4)
C4—C3—H3120.0C23—C17—S2119.9 (4)
C5—C4—C3120.6 (4)C17—C18—C19121.3 (6)
C5—C4—H4119.7C17—C18—H18119.3
C3—C4—H4119.7C19—C18—H18119.3
C4—C5—C6B119.1 (9)C17—C23—C22117.3 (5)
C4—C5—C6A117.2 (9)C17—C23—H23121.3
C4—C5—C8119.8 (3)C22—C23—H23121.3
C6B—C5—C8119.8 (9)C1—S1—O2B109.6 (12)
C6A—C5—C8122.1 (8)C1—S1—O2A128.1 (12)
C7A—C6A—C5122.7 (16)C1—S1—O1107.3 (3)
C7A—C6A—H6A118.6O2B—S1—O1118.3 (14)
C5—C6A—H6A118.6O2A—S1—O199.0 (12)
C7B—C6B—C5119.0 (17)C1—S1—C2107.9 (2)
C7B—C6B—H6B120.5O2B—S1—C2109.0 (18)
C5—C6B—H6B120.5O2A—S1—C2107.7 (16)
C6A—C7A—C2116.4 (17)O1—S1—C2104.3 (3)
C6A—C7A—H7A121.8O5—S2—O4118.6 (2)
C2—C7A—H7A121.8O5—S2—C17108.9 (2)
C6B—C7B—C2120.0 (17)O4—S2—C17108.9 (2)
C6B—C7B—H7B120.0O5—S2—C9107.52 (18)
C2—C7B—H7B120.0O4—S2—C9107.61 (18)
O3—C8—C5121.4 (4)C17—S2—C9104.35 (18)
O3—C8—C9120.1 (4)C20—C22—C23119.6 (6)
C5—C8—C9118.4 (3)C20—C22—H22120.2
C10—C9—C8125.3 (3)C23—C22—H22120.2
C10—C9—S2118.9 (3)C19—C20—C22119.6 (7)
C8—C9—S2115.8 (3)C19—C20—C21126.6 (9)
C9—C10—C11125.1 (3)C22—C20—C21113.7 (8)
C9—C10—H10117.4C20—C19—C18121.7 (8)
C11—C10—H10117.4C20—C19—H19119.2
C16—C11—C12118.7 (4)C18—C19—H19119.2
C16—C11—C10121.9 (3)C20—C21—H21A109.5
C12—C11—C10119.4 (4)C20—C21—H21B109.5
C13—C12—C11121.0 (4)H21A—C21—H21B109.5
C13—C12—H12119.5C20—C21—H21C109.5
C11—C12—H12119.5H21A—C21—H21C109.5
C12—C13—C14118.5 (5)H21B—C21—H21C109.5
C7B—C2—C3—C413.9 (11)F—C14—C15—C16178.9 (4)
C7A—C2—C3—C415.3 (11)C13—C14—C15—C160.3 (8)
S1—C2—C3—C4179.8 (4)C12—C11—C16—C150.2 (6)
C2—C3—C4—C50.6 (7)C10—C11—C16—C15179.6 (4)
C3—C4—C5—C6B12.5 (12)C14—C15—C16—C110.1 (7)
C3—C4—C5—C6A11.7 (10)C23—C17—C18—C190.7 (10)
C3—C4—C5—C8178.9 (4)S2—C17—C18—C19177.4 (6)
C4—C5—C6A—C7A9.9 (17)C18—C17—C23—C220.9 (7)
C6B—C5—C6A—C7A91 (5)S2—C17—C23—C22177.5 (3)
C8—C5—C6A—C7A179.1 (10)C3—C2—S1—C123.0 (5)
C4—C5—C6B—C7B9 (2)C7B—C2—S1—C1171.3 (10)
C6A—C5—C6B—C7B82 (4)C7A—C2—S1—C1142.3 (9)
C8—C5—C6B—C7B175.7 (12)C3—C2—S1—O2B141.9 (12)
C5—C6A—C7A—C23.9 (18)C7B—C2—S1—O2B52.4 (17)
C3—C2—C7A—C6A16.6 (15)C7A—C2—S1—O2B23.4 (16)
C7B—C2—C7A—C6A77 (4)C3—C2—S1—O2A164.5 (12)
S1—C2—C7A—C6A178.0 (9)C7B—C2—S1—O2A29.7 (17)
C5—C6B—C7B—C25 (2)C7A—C2—S1—O2A0.8 (16)
C3—C2—C7B—C6B17.0 (19)C3—C2—S1—O190.9 (5)
C7A—C2—C7B—C6B84 (3)C7B—C2—S1—O174.9 (11)
S1—C2—C7B—C6B177.0 (12)C7A—C2—S1—O1103.8 (9)
C4—C5—C8—O320.9 (6)C18—C17—S2—O5139.9 (4)
C6B—C5—C8—O3145.5 (11)C23—C17—S2—O543.5 (4)
C6A—C5—C8—O3170.3 (10)C18—C17—S2—O49.1 (5)
C4—C5—C8—C9159.0 (3)C23—C17—S2—O4174.2 (3)
C6B—C5—C8—C934.6 (12)C18—C17—S2—C9105.5 (4)
C6A—C5—C8—C99.9 (10)C23—C17—S2—C971.1 (4)
O3—C8—C9—C10118.1 (5)C10—C9—S2—O53.8 (4)
C5—C8—C9—C1061.7 (5)C8—C9—S2—O5173.3 (3)
O3—C8—C9—S265.0 (4)C10—C9—S2—O4132.6 (3)
C5—C8—C9—S2115.1 (3)C8—C9—S2—O444.4 (3)
C8—C9—C10—C116.0 (6)C10—C9—S2—C17111.8 (3)
S2—C9—C10—C11177.3 (3)C8—C9—S2—C1771.1 (3)
C9—C10—C11—C1639.3 (6)C17—C23—C22—C201.0 (7)
C9—C10—C11—C12141.2 (5)C23—C22—C20—C191.0 (10)
C16—C11—C12—C130.7 (8)C23—C22—C20—C21179.7 (5)
C10—C11—C12—C13179.8 (5)C22—C20—C19—C180.8 (12)
C11—C12—C13—C141.1 (10)C21—C20—C19—C18180.0 (8)
C12—C13—C14—C150.8 (9)C17—C18—C19—C200.6 (13)
C12—C13—C14—F178.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···Fi0.932.373.274 (8)167
Symmetry code: (i) x+3/2, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC23H19FO5S2
Mr458.52
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)9.6962 (7), 22.8539 (16), 10.8217 (7)
β (°) 109.672 (2)
V3)2258.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.26 × 0.15 × 0.15
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21889, 3994, 2543
Rint0.029
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.241, 1.01
No. of reflections3994
No. of parameters293
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C19—H19···Fi0.932.373.274 (8)167.4
Symmetry code: (i) x+3/2, y1/2, z1/2.
 

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

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