2-(4-Fluoro­phen­yl)-5,6-methyl­enedi­oxy-3-phenyl­sulfinyl-1-benzofuran monohydrate

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S160053681105553X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o375

doi:10.1107/S160053681105553X

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2-(4-Fluorophenyl)-5,6-methylenedioxy-3-phenylsulfinyl-1-benzofuran monohydrate

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 12 December 2011; accepted 24 December 2011; online 14 January 2012)

In the title compound, C₂₁H₁₃FO₄S·H₂O, the dihedral angles between the mean plane of the benzofuran fragment (r.m.s. deviation = 0.005 Å) and the pendant 4-fluorophenyl and phenyl rings are 6.24 (7) and 83.39 (6)°, respectively. In the crystal, molecules 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_r = 398.39
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.120
S = 1.02
3947 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.61 e Å⁻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) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y, z-1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681105553X/lr2043sup1.cif

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

checkCIF report

Comment top

Recently, many compounds having a benzofuran ring have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of 5,6-(methylenedioxy)benzofuran derivatives containing 2-(4-bromophenyl) (Choi et al., 2009) substituents, we report herein the crystal structure of the title compound.

The title compound crystallizes as a hydrate (Fig. 1). The benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 6.24 (7) and 83.39 (6)°, respectively. The crystal packing (Fig. 2) is stabilized by intermolecular O—H···O and C—H···O hydrogen bonds (see Table 1).

Related literature top

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 top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5,6-methylenedioxy-3-phenylsulfanyl-1-benzofuran (291 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 3 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 451–453 K; R_f = 0.79 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of crystal packing showing the O—H···O and C—H···O hydrogen bonds (dotted lines).H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x + 1, y, z (ii) x, - y + 1/2, z - 1/2 (iii) x, y, z - 1 (iv) x - 1, y, z; (v) x, y, z + 1.]

2-(4-Fluorophenyl)-5,6-methylenedioxy-3-phenylsulfinyl-1-benzofuran monohydrate top

Crystal data top

C₂₁H₁₃FO₄S·H₂O	F(000) = 824
M_r = 398.39	D_x = 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

Data collection top

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

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)] = 0.048	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(F_o²) + (0.0512P)² + 1.6272P] where P = (F_o² + 2F_c²)/3
3947 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.94 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₂₁H₁₃FO₄S·H₂O	V = 1710.01 (8) Å³
M_r = 398.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2485 (2) Å	µ = 0.23 mm⁻¹
b = 33.5624 (9) Å	T = 173 K
c = 6.1854 (2) Å	0.39 × 0.16 × 0.11 mm
β = 93.001 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3947 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3235 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.975	R_int = 0.036
16270 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.94 e Å⁻³
3947 reflections	Δρ_min = −0.61 e Å⁻³
261 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₃FO₄S·H₂O
M_r	398.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.2485 (2), 33.5624 (9), 6.1854 (2)
β (°)	93.001 (2)
V (Å³)	1710.01 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.39 × 0.16 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.915, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	16270, 3947, 3235
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.120, 1.02
No. of reflections	3947
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.94, −0.61

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O4ⁱ	0.95	2.46	3.375 (3)	161.7
C19—H19···O5wⁱ	0.95	2.49	3.433 (3)	170.9
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) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x, y, z−1.

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 2| February 2012| Page o375

doi:10.1107/S160053681105553X

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

2-(4-Fluoro­phen­yl)-5,6-methyl­enedi­­oxy-3-phenyl­sulfinyl-1-benzo­furan monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

2-(4-Fluorophenyl)-5,6-methylenedioxy-3-phenylsulfinyl-1-benzofuran monohydrate