3-Ethyl­sulfinyl-2-(3-fluoro­phen­yl)-5,6-methyl­enedi­oxy-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812044832

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3339

doi:10.1107/S1600536812044832

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3-Ethylsulfinyl-2-(3-fluorophenyl)-5,6-methylenedioxy-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 25 October 2012; accepted 30 October 2012; online 14 November 2012)

In the title compound, C₁₇H₁₃FO₄S, the 3-fluorophenyl ring makes a dihedral angle of 6.14 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯F, C—H⋯O and C—H⋯π interactions, forming a three--dimensional network. The crystal structure also exhibits slipped π–π interactions between the 3-fluorophenyl rings of neighbouring molecules [centroid–centroid distance = 3.769 (2) Å and slippage = 1.684 (2) Å].

Related literature

For background information on and the crystal structures of related benzofuran compounds, see: Choi et al. (2010 ); Seo et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₃FO₄S
M_r = 332.33
Monoclinic, P 2₁ /c
a = 8.8516 (2) Å
b = 21.8221 (4) Å
c = 7.7228 (2) Å
β = 102.949 (1)°
V = 1453.80 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.39 × 0.29 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.908, T_max = 0.937
14376 measured reflections
3600 independent reflections
3131 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.02
3600 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O4ⁱ	0.99	2.45	3.314 (2)	145
C9—H9B⋯O2ⁱⁱ	0.99	2.59	3.519 (3)	156
C16—H16A⋯O4ⁱⁱⁱ	0.99	2.29	3.2689 (19)	169
C6—H6⋯F1^iv	0.95	2.37	3.2532 (18)	154
C17—H17B⋯Cg1^v	0.98	2.74	3.642 (3)	153
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x+1, y, z+1; (v) 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 global, I. DOI: 10.1107/S1600536812044832/mw2094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044832/mw2094Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044832/mw2094Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5,6-methylenedioxy-1-benzofuran derivatives containing [3-ethylsulfinyl-2-(4-fluorophenyl)] (Choi et al., 2010) and [2-(4-fluorophenyl)-3-isopropylsulfinyl] (Seo et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 6.14 (5)°. In the crystal structure (Figs. 2 & 3), molecules are connected by weak C—H···F, C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 3) also exhibits slipped π–π interactions between the 3-fluorophenyl rings of neighbouring molecules, with a Cg2···Cg2^vi distance of 3.769 (2) Å and an interplanar distance of 3.372 (2) Å resulting in a slippage of 1.684 (2) Å (Cg2 is the centroid of the C10–C15 3-fluorophenyl ring).

Related literature top

For background information on and the crystal structures of related benzofuran compounds, see: Choi et al. (2010); Seo et al. (2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-ethylsulfanyl-2-(3-fluorophenyl)-5,6-methylenedioxy-1-benzofuran (284 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 408–409 K; R_f = 0.61 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···F and C—H···O interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x + 1, - y + 3/2, z + 1/2; (ii) x, - y + 3/2, z + 1/2; (iii) x, - y + 3/2, z - 1/2; (iv) x + 1, y, z + 1 (vii) x - 1, - y + 3/2, z - 1/2; (viii) x, - y + 3/2, z + 1/2; (ix) x, - y + 3/2, z + 1/2; (x) x - 1, y, z - 1.]
	Fig. 3. A view of the C—H···π and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (v) x, y, z - 1; (vi) - x, - y + 1, - z + 1; (xi) x, y, z + 1.]

3-Ethylsulfinyl-2-(3-fluorophenyl)-5,6-methylenedioxy-1-benzofuran top

Crystal data top

C₁₇H₁₃FO₄S	F(000) = 688
M_r = 332.33	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 408 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8516 (2) Å	Cell parameters from 6139 reflections
b = 21.8221 (4) Å	θ = 2.9–28.2°
c = 7.7228 (2) Å	µ = 0.25 mm⁻¹
β = 102.949 (1)°	T = 173 K
V = 1453.80 (6) Å³	Block, colourless
Z = 4	0.39 × 0.29 × 0.26 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3600 independent reflections
Radiation source: rotating anode	3131 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.025
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.9°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −29→27
T_min = 0.908, T_max = 0.937	l = −10→10
14376 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0488P)² + 0.7371P] where P = (F_o² + 2F_c²)/3
3600 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₇H₁₃FO₄S	V = 1453.80 (6) Å³
M_r = 332.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8516 (2) Å	µ = 0.25 mm⁻¹
b = 21.8221 (4) Å	T = 173 K
c = 7.7228 (2) Å	0.39 × 0.29 × 0.26 mm
β = 102.949 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3600 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3131 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.937	R_int = 0.025
14376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	Δρ_max = 0.45 e Å⁻³
3600 reflections	Δρ_min = −0.35 e Å⁻³
209 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.20748 (4)	0.653717 (15)	0.40724 (5)	0.02313 (11)
F1	−0.09845 (13)	0.46852 (5)	0.11643 (15)	0.0452 (3)
O1	0.44774 (12)	0.52350 (4)	0.70767 (14)	0.0247 (2)
O2	0.76433 (15)	0.73096 (6)	0.93233 (18)	0.0424 (3)
O3	0.86160 (15)	0.64201 (6)	1.07899 (18)	0.0431 (3)
O4	0.18119 (13)	0.70803 (5)	0.51487 (16)	0.0341 (3)
C1	0.33826 (16)	0.60530 (6)	0.55117 (19)	0.0215 (3)
C2	0.47112 (16)	0.62662 (6)	0.68258 (18)	0.0222 (3)
C3	0.54231 (17)	0.68385 (7)	0.7276 (2)	0.0252 (3)
H3	0.5037	0.7207	0.6683	0.030*
C4	0.67160 (18)	0.68235 (7)	0.8635 (2)	0.0271 (3)
C5	0.72968 (17)	0.62887 (7)	0.9530 (2)	0.0278 (3)
C6	0.66316 (17)	0.57266 (7)	0.9140 (2)	0.0271 (3)
H6	0.7020	0.5362	0.9755	0.033*
C7	0.53247 (16)	0.57424 (6)	0.77457 (19)	0.0229 (3)
C8	0.32896 (16)	0.54330 (6)	0.57115 (19)	0.0223 (3)
C9	0.8859 (2)	0.70603 (8)	1.0666 (2)	0.0403 (4)
H9A	0.9872	0.7137	1.0365	0.048*
H9B	0.8866	0.7259	1.1821	0.048*
C10	0.22658 (16)	0.49448 (6)	0.48447 (19)	0.0225 (3)
C11	0.10942 (17)	0.50551 (7)	0.3331 (2)	0.0257 (3)
H11	0.0948	0.5451	0.2812	0.031*
C12	0.01626 (18)	0.45741 (7)	0.2619 (2)	0.0274 (3)
C13	0.03117 (18)	0.39881 (7)	0.3285 (2)	0.0292 (3)
H13	−0.0358	0.3668	0.2743	0.035*
C14	0.14759 (19)	0.38828 (7)	0.4776 (2)	0.0314 (3)
H14	0.1613	0.3483	0.5272	0.038*
C15	0.24452 (18)	0.43523 (7)	0.5557 (2)	0.0280 (3)
H15	0.3238	0.4272	0.6583	0.034*
C16	0.33604 (19)	0.67847 (7)	0.2700 (2)	0.0306 (3)
H16A	0.2947	0.7164	0.2061	0.037*
H16B	0.4390	0.6880	0.3462	0.037*
C17	0.3535 (2)	0.62964 (10)	0.1369 (3)	0.0450 (4)
H17A	0.3961	0.5923	0.2000	0.068*
H17B	0.4237	0.6443	0.0642	0.068*
H17C	0.2519	0.6206	0.0600	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02202 (18)	0.01839 (17)	0.02712 (19)	0.00208 (12)	0.00156 (13)	0.00075 (13)
F1	0.0445 (6)	0.0362 (5)	0.0436 (6)	−0.0053 (4)	−0.0138 (5)	−0.0012 (4)
O1	0.0256 (5)	0.0197 (5)	0.0266 (5)	0.0015 (4)	0.0013 (4)	0.0023 (4)
O2	0.0397 (7)	0.0311 (6)	0.0465 (7)	−0.0092 (5)	−0.0113 (6)	−0.0031 (5)
O3	0.0365 (7)	0.0404 (7)	0.0419 (7)	−0.0063 (5)	−0.0133 (5)	0.0026 (5)
O4	0.0370 (6)	0.0226 (5)	0.0417 (7)	0.0079 (4)	0.0069 (5)	−0.0049 (5)
C1	0.0206 (6)	0.0208 (6)	0.0233 (6)	0.0025 (5)	0.0050 (5)	0.0011 (5)
C2	0.0216 (6)	0.0227 (7)	0.0226 (7)	0.0025 (5)	0.0056 (5)	−0.0009 (5)
C3	0.0261 (7)	0.0212 (7)	0.0278 (7)	0.0020 (5)	0.0046 (6)	−0.0011 (5)
C4	0.0264 (7)	0.0257 (7)	0.0288 (7)	−0.0023 (6)	0.0051 (6)	−0.0037 (6)
C5	0.0225 (7)	0.0342 (8)	0.0248 (7)	−0.0003 (6)	0.0011 (6)	−0.0010 (6)
C6	0.0262 (7)	0.0271 (7)	0.0264 (7)	0.0040 (6)	0.0021 (6)	0.0047 (6)
C7	0.0233 (7)	0.0211 (7)	0.0241 (7)	0.0002 (5)	0.0051 (5)	0.0000 (5)
C8	0.0219 (6)	0.0220 (7)	0.0225 (7)	0.0022 (5)	0.0041 (5)	0.0007 (5)
C9	0.0382 (9)	0.0403 (9)	0.0363 (9)	−0.0093 (8)	−0.0048 (7)	−0.0005 (7)
C10	0.0241 (7)	0.0196 (6)	0.0253 (7)	0.0001 (5)	0.0086 (5)	−0.0007 (5)
C11	0.0279 (7)	0.0212 (7)	0.0278 (7)	0.0001 (5)	0.0058 (6)	−0.0005 (5)
C12	0.0271 (7)	0.0274 (7)	0.0270 (7)	0.0003 (6)	0.0045 (6)	−0.0030 (6)
C13	0.0319 (8)	0.0242 (7)	0.0333 (8)	−0.0058 (6)	0.0111 (6)	−0.0059 (6)
C14	0.0391 (9)	0.0202 (7)	0.0360 (8)	−0.0007 (6)	0.0106 (7)	0.0017 (6)
C15	0.0308 (7)	0.0236 (7)	0.0289 (7)	0.0009 (6)	0.0050 (6)	0.0031 (6)
C16	0.0310 (8)	0.0296 (8)	0.0301 (8)	−0.0033 (6)	0.0046 (6)	0.0080 (6)
C17	0.0486 (11)	0.0550 (12)	0.0347 (9)	−0.0016 (9)	0.0162 (8)	−0.0018 (8)

Geometric parameters (Å, º) top

S1—O4	1.4954 (11)	C8—C10	1.4602 (19)
S1—C1	1.7651 (14)	C9—H9A	0.9900
S1—C16	1.8029 (16)	C9—H9B	0.9900
F1—C12	1.3568 (18)	C10—C11	1.399 (2)
O1—C7	1.3717 (17)	C10—C15	1.400 (2)
O1—C8	1.3809 (16)	C11—C12	1.372 (2)
O2—C4	1.3733 (18)	C11—H11	0.9500
O2—C9	1.424 (2)	C12—C13	1.373 (2)
O3—C5	1.3724 (18)	C13—C14	1.381 (2)
O3—C9	1.420 (2)	C13—H13	0.9500
C1—C8	1.366 (2)	C14—C15	1.385 (2)
C1—C2	1.4473 (19)	C14—H14	0.9500
C2—C7	1.3905 (19)	C15—H15	0.9500
C2—C3	1.407 (2)	C16—C17	1.513 (3)
C3—C4	1.369 (2)	C16—H16A	0.9900
C3—H3	0.9500	C16—H16B	0.9900
C4—C5	1.395 (2)	C17—H17A	0.9800
C5—C6	1.365 (2)	C17—H17B	0.9800
C6—C7	1.393 (2)	C17—H17C	0.9800
C6—H6	0.9500

O4—S1—C1	106.63 (7)	O3—C9—H9B	109.9
O4—S1—C16	106.65 (7)	O2—C9—H9B	109.9
C1—S1—C16	97.95 (7)	H9A—C9—H9B	108.3
C7—O1—C8	107.07 (10)	C11—C10—C15	118.99 (13)
C4—O2—C9	105.97 (13)	C11—C10—C8	121.69 (13)
C5—O3—C9	105.99 (13)	C15—C10—C8	119.32 (13)
C8—C1—C2	107.41 (12)	C12—C11—C10	118.03 (14)
C8—C1—S1	128.05 (11)	C12—C11—H11	121.0
C2—C1—S1	124.35 (11)	C10—C11—H11	121.0
C7—C2—C3	120.10 (13)	F1—C12—C11	117.79 (14)
C7—C2—C1	104.88 (12)	F1—C12—C13	117.90 (13)
C3—C2—C1	135.01 (13)	C11—C12—C13	124.31 (14)
C4—C3—C2	114.80 (13)	C12—C13—C14	117.26 (14)
C4—C3—H3	122.6	C12—C13—H13	121.4
C2—C3—H3	122.6	C14—C13—H13	121.4
C3—C4—O2	127.07 (14)	C13—C14—C15	120.90 (14)
C3—C4—C5	123.50 (14)	C13—C14—H14	119.5
O2—C4—C5	109.43 (13)	C15—C14—H14	119.5
C6—C5—O3	126.94 (14)	C14—C15—C10	120.50 (14)
C6—C5—C4	123.35 (14)	C14—C15—H15	119.8
O3—C5—C4	109.70 (14)	C10—C15—H15	119.8
C5—C6—C7	113.02 (13)	C17—C16—S1	111.26 (12)
C5—C6—H6	123.5	C17—C16—H16A	109.4
C7—C6—H6	123.5	S1—C16—H16A	109.4
O1—C7—C2	110.68 (12)	C17—C16—H16B	109.4
O1—C7—C6	124.09 (12)	S1—C16—H16B	109.4
C2—C7—C6	125.22 (13)	H16A—C16—H16B	108.0
C1—C8—O1	109.95 (12)	C16—C17—H17A	109.5
C1—C8—C10	135.85 (13)	C16—C17—H17B	109.5
O1—C8—C10	114.20 (12)	H17A—C17—H17B	109.5
O3—C9—O2	108.90 (13)	C16—C17—H17C	109.5
O3—C9—H9A	109.9	H17A—C17—H17C	109.5
O2—C9—H9A	109.9	H17B—C17—H17C	109.5

O4—S1—C1—C8	134.07 (14)	C1—C2—C7—C6	179.62 (14)
C16—S1—C1—C8	−115.83 (15)	C5—C6—C7—O1	178.29 (14)
O4—S1—C1—C2	−40.34 (14)	C5—C6—C7—C2	−0.7 (2)
C16—S1—C1—C2	69.76 (13)	C2—C1—C8—O1	0.08 (16)
C8—C1—C2—C7	−0.34 (16)	S1—C1—C8—O1	−175.09 (10)
S1—C1—C2—C7	175.05 (11)	C2—C1—C8—C10	−179.64 (16)
C8—C1—C2—C3	178.82 (16)	S1—C1—C8—C10	5.2 (3)
S1—C1—C2—C3	−5.8 (2)	C7—O1—C8—C1	0.22 (16)
C7—C2—C3—C4	0.3 (2)	C7—O1—C8—C10	180.00 (12)
C1—C2—C3—C4	−178.78 (16)	C5—O3—C9—O2	0.8 (2)
C2—C3—C4—O2	178.99 (15)	C4—O2—C9—O3	−1.3 (2)
C2—C3—C4—C5	−0.4 (2)	C1—C8—C10—C11	5.9 (3)
C9—O2—C4—C3	−178.18 (17)	O1—C8—C10—C11	−173.83 (13)
C9—O2—C4—C5	1.29 (19)	C1—C8—C10—C15	−173.27 (17)
C9—O3—C5—C6	178.63 (17)	O1—C8—C10—C15	7.0 (2)
C9—O3—C5—C4	−0.03 (19)	C15—C10—C11—C12	0.5 (2)
C3—C4—C5—C6	0.0 (3)	C8—C10—C11—C12	−178.70 (14)
O2—C4—C5—C6	−179.54 (15)	C10—C11—C12—F1	179.18 (13)
C3—C4—C5—O3	178.68 (15)	C10—C11—C12—C13	−0.6 (2)
O2—C4—C5—O3	−0.81 (19)	F1—C12—C13—C14	−179.45 (14)
O3—C5—C6—C7	−177.91 (15)	C11—C12—C13—C14	0.3 (2)
C4—C5—C6—C7	0.6 (2)	C12—C13—C14—C15	0.1 (2)
C8—O1—C7—C2	−0.45 (16)	C13—C14—C15—C10	−0.2 (2)
C8—O1—C7—C6	−179.59 (14)	C11—C10—C15—C14	−0.1 (2)
C3—C2—C7—O1	−178.82 (13)	C8—C10—C15—C14	179.08 (14)
C1—C2—C7—O1	0.49 (16)	O4—S1—C16—C17	−172.19 (12)
C3—C2—C7—C6	0.3 (2)	C1—S1—C16—C17	77.73 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O4ⁱ	0.99	2.45	3.314 (2)	145
C9—H9B···O2ⁱⁱ	0.99	2.59	3.519 (3)	156
C16—H16A···O4ⁱⁱⁱ	0.99	2.29	3.2689 (19)	169
C6—H6···F1^iv	0.95	2.37	3.2532 (18)	154
C17—H17B···Cg1^v	0.98	2.74	3.642 (3)	153

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x+1, y, z+1; (v) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃FO₄S
M_r	332.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.8516 (2), 21.8221 (4), 7.7228 (2)
β (°)	102.949 (1)
V (Å³)	1453.80 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.39 × 0.29 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.908, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	14376, 3600, 3131
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.02
No. of reflections	3600
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.35

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

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O4ⁱ	0.99	2.45	3.314 (2)	145
C9—H9B···O2ⁱⁱ	0.99	2.59	3.519 (3)	156
C16—H16A···O4ⁱⁱⁱ	0.99	2.29	3.2689 (19)	169
C6—H6···F1^iv	0.95	2.37	3.2532 (18)	154
C17—H17B···Cg1^v	0.98	2.74	3.642 (3)	153

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x+1, y, z+1; (v) x, y, z−1.

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

References

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. (2010). Acta Cryst. E66, o1296. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3504. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page o3339

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