2-(4-Fluoro-phen-yl)-5,6-methyl-enedi-oxy-3-phenyl-sulfinyl-1-benzofuran monohydrate.

In the title compound, C(21)H(13)FO(4)S·H(2)O, the dihedral angles between the mean plane of the benzofuran fragment (r.m.s. deviation = 0.005 Å) and the pendant 4-fluoro-phenyl and phenyl rings are 6.24 (7) and 83.39 (6)°, respectively. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al.(2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structure of related compound, see: Choi et al. (2009 ▶).

Experimental

Crystal data

C21H13FO4S·H2O

M = 398.39

Monoclinic,

a = 8.2485 (2) Å

b = 33.5624 (9) Å

c = 6.1854 (2) Å

β = 93.001 (2)°

V = 1710.01 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.39 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.915, T max = 0.975

16270 measured reflections

3947 independent reflections

3235 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.120

S = 1.02

3947 reflections

261 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.94 e Å−3

Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681105553X/lr2043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105553X/lr2043Isup2.hkl

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

C21H13FO4S·H2O	F(000) = 824
Mr = 398.39	Dx = 1.547 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4953 reflections
a = 8.2485 (2) Å	θ = 2.4–28.3°
b = 33.5624 (9) Å	µ = 0.23 mm−1
c = 6.1854 (2) Å	T = 173 K
β = 93.001 (2)°	Block, colourless
V = 1710.01 (8) Å3	0.39 × 0.16 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3947 independent reflections
Radiation source: rotating anode	3235 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.036
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.2°
φ and ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −43→35
Tmin = 0.915, Tmax = 0.975	l = −8→7
16270 measured reflections

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0512P)2 + 1.6272P] where P = (Fo2 + 2Fc2)/3
3947 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.61 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
S1	0.50867 (6)	0.170330 (15)	0.88006 (8)	0.02163 (14)
F1	0.92782 (18)	0.04232 (4)	1.5856 (2)	0.0415 (4)
O1	0.49612 (16)	0.05550 (4)	0.7261 (2)	0.0205 (3)
O2	0.14035 (19)	0.12607 (5)	0.0740 (3)	0.0318 (4)
O3	0.1737 (2)	0.05788 (5)	0.0443 (3)	0.0330 (4)
O4	0.36252 (17)	0.19343 (4)	0.8043 (3)	0.0283 (3)
C1	0.4801 (2)	0.12171 (6)	0.7748 (3)	0.0181 (4)
C2	0.3882 (2)	0.11212 (6)	0.5762 (3)	0.0191 (4)
C3	0.2973 (2)	0.13442 (6)	0.4188 (3)	0.0210 (4)
H3	0.2838	0.1625	0.4280	0.025*
C4	0.2305 (2)	0.11216 (6)	0.2522 (3)	0.0222 (4)
C5	0.0887 (3)	0.09168 (7)	−0.0456 (4)	0.0271 (5)
H5A	0.1125	0.0949	−0.1998	0.033*
H5B	−0.0298	0.0879	−0.0365	0.033*
C6	0.2492 (2)	0.07098 (6)	0.2341 (3)	0.0230 (4)
C7	0.3353 (2)	0.04845 (6)	0.3848 (3)	0.0230 (4)
H7	0.3475	0.0204	0.3741	0.028*
C8	0.4031 (2)	0.07100 (6)	0.5549 (3)	0.0201 (4)
C9	0.5414 (2)	0.08705 (6)	0.8597 (3)	0.0186 (4)
C10	0.6438 (2)	0.07586 (6)	1.0502 (3)	0.0191 (4)
C11	0.6993 (3)	0.03679 (6)	1.0741 (3)	0.0255 (5)
H11	0.6700	0.0177	0.9659	0.031*
C12	0.7964 (3)	0.02540 (7)	1.2529 (4)	0.0294 (5)
H12	0.8349	−0.0012	1.2681	0.035*
C13	0.8354 (3)	0.05361 (7)	1.4074 (3)	0.0270 (5)
C14	0.7845 (3)	0.09240 (7)	1.3922 (3)	0.0260 (5)
H14	0.8147	0.1112	1.5020	0.031*
C15	0.6878 (2)	0.10357 (6)	1.2123 (3)	0.0228 (4)
H15	0.6510	0.1303	1.1987	0.027*
C16	0.6720 (2)	0.18499 (6)	0.7173 (3)	0.0197 (4)
C17	0.8292 (2)	0.17949 (6)	0.8061 (4)	0.0255 (4)
H17	0.8473	0.1685	0.9469	0.031*
C18	0.9588 (3)	0.19039 (7)	0.6845 (4)	0.0329 (5)
H18	1.0670	0.1865	0.7411	0.039*
C19	0.9309 (3)	0.20687 (7)	0.4815 (4)	0.0348 (5)
H19	1.0201	0.2141	0.3987	0.042*
C20	0.7737 (3)	0.21292 (7)	0.3973 (4)	0.0305 (5)
H20	0.7559	0.2246	0.2584	0.037*
C21	0.6421 (3)	0.20191 (6)	0.5153 (3)	0.0242 (4)
H21	0.5341	0.2059	0.4585	0.029*
O5W	0.2797 (2)	0.22591 (6)	0.2201 (3)	0.0421 (4)
H5WA	0.307 (5)	0.2545 (13)	0.220 (6)	0.084 (12)*
H5WB	0.292 (4)	0.2198 (12)	0.069 (7)	0.083 (12)*

	U11	U22	U33	U12	U13	U23
S1	0.0222 (2)	0.0171 (3)	0.0259 (3)	0.00014 (18)	0.00387 (19)	−0.0036 (2)
F1	0.0526 (9)	0.0387 (8)	0.0310 (8)	0.0113 (7)	−0.0197 (7)	−0.0006 (6)
O1	0.0263 (7)	0.0156 (7)	0.0192 (7)	0.0000 (5)	−0.0028 (6)	−0.0017 (5)
O2	0.0371 (9)	0.0290 (9)	0.0277 (8)	0.0027 (7)	−0.0124 (7)	0.0002 (7)
O3	0.0407 (9)	0.0296 (9)	0.0272 (8)	0.0021 (7)	−0.0123 (7)	−0.0066 (7)
O4	0.0244 (7)	0.0239 (8)	0.0367 (9)	0.0046 (6)	0.0012 (6)	0.0001 (7)
C1	0.0187 (9)	0.0165 (9)	0.0193 (9)	−0.0003 (7)	0.0024 (7)	−0.0018 (8)
C2	0.0176 (8)	0.0182 (10)	0.0217 (10)	−0.0013 (7)	0.0021 (7)	−0.0008 (8)
C3	0.0203 (9)	0.0175 (10)	0.0251 (10)	0.0010 (7)	0.0019 (8)	0.0008 (8)
C4	0.0190 (9)	0.0252 (11)	0.0222 (10)	0.0010 (8)	−0.0012 (8)	0.0030 (8)
C5	0.0244 (10)	0.0320 (12)	0.0245 (11)	−0.0010 (9)	−0.0024 (8)	−0.0011 (9)
C6	0.0229 (9)	0.0244 (11)	0.0215 (10)	−0.0031 (8)	−0.0005 (8)	−0.0029 (8)
C7	0.0258 (10)	0.0187 (10)	0.0243 (10)	0.0000 (8)	−0.0008 (8)	−0.0032 (8)
C8	0.0193 (9)	0.0192 (10)	0.0220 (10)	−0.0003 (7)	0.0010 (7)	0.0008 (8)
C9	0.0187 (9)	0.0173 (10)	0.0201 (9)	−0.0017 (7)	0.0022 (7)	−0.0020 (8)
C10	0.0181 (9)	0.0205 (10)	0.0188 (9)	−0.0006 (7)	0.0021 (7)	−0.0001 (8)
C11	0.0313 (11)	0.0204 (11)	0.0243 (11)	0.0020 (8)	−0.0028 (9)	−0.0033 (8)
C12	0.0356 (11)	0.0217 (11)	0.0302 (12)	0.0049 (9)	−0.0043 (9)	0.0009 (9)
C13	0.0275 (10)	0.0314 (12)	0.0215 (10)	0.0036 (9)	−0.0044 (8)	0.0025 (9)
C14	0.0296 (11)	0.0265 (11)	0.0216 (10)	0.0001 (9)	−0.0025 (8)	−0.0049 (9)
C15	0.0265 (10)	0.0191 (10)	0.0228 (10)	0.0024 (8)	0.0016 (8)	−0.0015 (8)
C16	0.0187 (9)	0.0159 (9)	0.0245 (10)	−0.0013 (7)	0.0018 (8)	−0.0034 (8)
C17	0.0235 (10)	0.0229 (11)	0.0298 (11)	−0.0006 (8)	−0.0021 (9)	−0.0006 (9)
C18	0.0188 (9)	0.0330 (13)	0.0467 (14)	−0.0010 (9)	0.0008 (9)	−0.0024 (11)
C19	0.0313 (11)	0.0295 (13)	0.0449 (14)	−0.0048 (10)	0.0140 (10)	−0.0007 (11)
C20	0.0391 (12)	0.0264 (12)	0.0262 (11)	−0.0021 (10)	0.0044 (9)	0.0013 (9)
C21	0.0245 (10)	0.0212 (11)	0.0263 (11)	−0.0003 (8)	−0.0032 (8)	−0.0019 (8)
O5W	0.0574 (12)	0.0293 (10)	0.0406 (11)	−0.0024 (8)	0.0123 (9)	−0.0008 (8)

S1—O4	1.4883 (15)	C10—C11	1.394 (3)
S1—C1	1.768 (2)	C10—C15	1.401 (3)
S1—C16	1.792 (2)	C11—C12	1.385 (3)
F1—C13	1.361 (2)	C11—H11	0.9500
O1—C8	1.377 (2)	C12—C13	1.372 (3)
O1—C9	1.382 (2)	C12—H12	0.9500
O2—C4	1.379 (2)	C13—C14	1.370 (3)
O2—C5	1.424 (3)	C14—C15	1.386 (3)
O3—C6	1.372 (2)	C14—H14	0.9500
O3—C5	1.431 (3)	C15—H15	0.9500
C1—C9	1.362 (3)	C16—C21	1.382 (3)
C1—C2	1.446 (3)	C16—C17	1.394 (3)
C2—C8	1.392 (3)	C17—C18	1.388 (3)
C2—C3	1.412 (3)	C17—H17	0.9500
C3—C4	1.365 (3)	C18—C19	1.380 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C6	1.396 (3)	C19—C20	1.386 (3)
C5—H5A	0.9900	C19—H19	0.9500
C5—H5B	0.9900	C20—C21	1.389 (3)
C6—C7	1.370 (3)	C20—H20	0.9500
C7—C8	1.390 (3)	C21—H21	0.9500
C7—H7	0.9500	O5W—H5WA	0.99 (4)
C9—C10	1.463 (3)	O5W—H5WB	0.97 (4)
O4—S1—C1	105.95 (9)	C11—C10—C9	119.98 (18)
O4—S1—C16	107.47 (9)	C15—C10—C9	121.54 (18)
C1—S1—C16	97.82 (9)	C12—C11—C10	121.2 (2)
C8—O1—C9	107.01 (15)	C12—C11—H11	119.4
C4—O2—C5	105.97 (16)	C10—C11—H11	119.4
C6—O3—C5	105.66 (16)	C13—C12—C11	118.1 (2)
C9—C1—C2	107.74 (17)	C13—C12—H12	121.0
C9—C1—S1	127.35 (15)	C11—C12—H12	121.0
C2—C1—S1	124.90 (15)	F1—C13—C14	118.50 (19)
C8—C2—C3	120.43 (18)	F1—C13—C12	118.2 (2)
C8—C2—C1	104.83 (17)	C14—C13—C12	123.3 (2)
C3—C2—C1	134.74 (19)	C13—C14—C15	118.3 (2)
C4—C3—C2	114.14 (19)	C13—C14—H14	120.9
C4—C3—H3	122.9	C15—C14—H14	120.9
C2—C3—H3	122.9	C14—C15—C10	120.8 (2)
C3—C4—O2	126.70 (19)	C14—C15—H15	119.6
C3—C4—C6	124.11 (19)	C10—C15—H15	119.6
O2—C4—C6	109.16 (17)	C21—C16—C17	121.89 (19)
O2—C5—O3	108.26 (16)	C21—C16—S1	121.13 (15)
O2—C5—H5A	110.0	C17—C16—S1	116.96 (16)
O3—C5—H5A	110.0	C18—C17—C16	118.6 (2)
O2—C5—H5B	110.0	C18—C17—H17	120.7
O3—C5—H5B	110.0	C16—C17—H17	120.7
H5A—C5—H5B	108.4	C19—C18—C17	120.1 (2)
C7—C6—O3	127.0 (2)	C19—C18—H18	119.9
C7—C6—C4	123.18 (19)	C17—C18—H18	119.9
O3—C6—C4	109.81 (18)	C18—C19—C20	120.6 (2)
C6—C7—C8	112.86 (19)	C18—C19—H19	119.7
C6—C7—H7	123.6	C20—C19—H19	119.7
C8—C7—H7	123.6	C19—C20—C21	120.3 (2)
O1—C8—C7	124.23 (18)	C19—C20—H20	119.8
O1—C8—C2	110.50 (17)	C21—C20—H20	119.8
C7—C8—C2	125.26 (19)	C16—C21—C20	118.5 (2)
C1—C9—O1	109.91 (17)	C16—C21—H21	120.8
C1—C9—C10	135.77 (18)	C20—C21—H21	120.8
O1—C9—C10	114.29 (16)	H5WA—O5W—H5WB	100 (3)
C11—C10—C15	118.48 (19)
O4—S1—C1—C9	−152.40 (17)	C2—C1—C9—O1	0.7 (2)
C16—S1—C1—C9	96.85 (18)	S1—C1—C9—O1	−177.99 (13)
O4—S1—C1—C2	29.11 (18)	C2—C1—C9—C10	179.0 (2)
C16—S1—C1—C2	−81.65 (17)	S1—C1—C9—C10	0.3 (3)
C9—C1—C2—C8	−0.6 (2)	C8—O1—C9—C1	−0.5 (2)
S1—C1—C2—C8	178.14 (14)	C8—O1—C9—C10	−179.20 (15)
C9—C1—C2—C3	179.6 (2)	C1—C9—C10—C11	−172.4 (2)
S1—C1—C2—C3	−1.7 (3)	O1—C9—C10—C11	5.7 (3)
C8—C2—C3—C4	−0.4 (3)	C1—C9—C10—C15	7.8 (3)
C1—C2—C3—C4	179.5 (2)	O1—C9—C10—C15	−173.98 (17)
C2—C3—C4—O2	−178.00 (18)	C15—C10—C11—C12	−0.3 (3)
C2—C3—C4—C6	−0.4 (3)	C9—C10—C11—C12	180.00 (19)
C5—O2—C4—C3	−176.2 (2)	C10—C11—C12—C13	0.6 (3)
C5—O2—C4—C6	5.9 (2)	C11—C12—C13—F1	178.6 (2)
C4—O2—C5—O3	−10.2 (2)	C11—C12—C13—C14	−0.7 (4)
C6—O3—C5—O2	10.6 (2)	F1—C13—C14—C15	−178.81 (19)
C5—O3—C6—C7	174.8 (2)	C12—C13—C14—C15	0.5 (3)
C5—O3—C6—C4	−7.0 (2)	C13—C14—C15—C10	−0.1 (3)
C3—C4—C6—C7	1.0 (3)	C11—C10—C15—C14	0.0 (3)
O2—C4—C6—C7	178.98 (19)	C9—C10—C15—C14	179.77 (18)
C3—C4—C6—O3	−177.25 (18)	O4—S1—C16—C21	−22.09 (19)
O2—C4—C6—O3	0.7 (2)	C1—S1—C16—C21	87.42 (18)
O3—C6—C7—C8	177.22 (19)	O4—S1—C16—C17	156.30 (16)
C4—C6—C7—C8	−0.7 (3)	C1—S1—C16—C17	−94.18 (17)
C9—O1—C8—C7	179.68 (18)	C21—C16—C17—C18	−1.8 (3)
C9—O1—C8—C2	0.1 (2)	S1—C16—C17—C18	179.81 (17)
C6—C7—C8—O1	−179.52 (17)	C16—C17—C18—C19	1.0 (3)
C6—C7—C8—C2	0.0 (3)	C17—C18—C19—C20	0.4 (4)
C3—C2—C8—O1	−179.85 (16)	C18—C19—C20—C21	−0.9 (4)
C1—C2—C8—O1	0.3 (2)	C17—C16—C21—C20	1.2 (3)
C3—C2—C8—C7	0.6 (3)	S1—C16—C21—C20	179.56 (16)
C1—C2—C8—C7	−179.26 (18)	C19—C20—C21—C16	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O4i	0.95	2.46	3.375 (3)	162.
C19—H19···O5wi	0.95	2.49	3.433 (3)	171.
O5W—H5WA···O4ii	0.99 (4)	1.87 (4)	2.834 (2)	164 (3)
O5W—H5WB···O4iii	0.97 (4)	1.98 (4)	2.908 (2)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O4i	0.95	2.46	3.375 (3)	162
C19—H19⋯O5wi	0.95	2.49	3.433 (3)	171
O5W—H5WA⋯O4ii	0.99 (4)	1.87 (4)	2.834 (2)	164 (3)
O5W—H5WB⋯O4iii	0.97 (4)	1.98 (4)	2.908 (2)	161 (3)

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