(Z)-3-(4-Fluoro-phen-yl)-1-[4-(methyl-sulfon-yl)phen-yl]-2-tosyl-prop-2-en-1-one.

In the title compound, C(23)H(19)FO(5)S(2), 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 methyl-phenyl and fluoro-phenyl 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 inter-actions.

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 = 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

Δρmax = 0.57 e Å−3

Δρmin = −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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H19FO5S2	F(000) = 952
Mr = 458.52	Dx = 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

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

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(Fo2) + (0.1393P)2 + 1.1164P] where P = (Fo2 + 2Fc2)/3
3994 reflections	(Δ/σ)max = 0.015
293 parameters	Δρmax = 0.57 e Å−3
4 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) .