3-(2-Fluoro­phenyl­sulfin­yl)-2,4,5,6-tetra­methyl-1-benzofuran

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

doi:10.1107/S1600536812035714

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2742

doi:10.1107/S1600536812035714

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3-(2-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-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 2 August 2012; accepted 14 August 2012; online 23 August 2012)

In the title compound, C₁₈H₁₇FO₂S, the 2-fluorophenyl ring makes a dihedral angle of 85.45 (4)° with the mean plane [r.m.s. deviation = 0.017 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Seo et al. (2011a ,b ).

Experimental

Crystal data

C₁₈H₁₇FO₂S
M_r = 316.38
Monoclinic, P 2₁ /c
a = 14.6851 (4) Å
b = 6.0786 (2) Å
c = 17.1647 (4) Å
β = 102.223 (1)°
V = 1497.47 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.33 × 0.30 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.593, T_max = 0.746
24418 measured reflections
3264 independent reflections
2803 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.08
3264 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C13–C18 2-fluorophenyl ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.40	3.3279 (19)	165
C12—H12C⋯Cg1ⁱⁱ	0.98	2.69	3.486 (2)	138
C16—H16⋯Cg2ⁱⁱⁱ	0.95	2.70	3.553 (2)	149
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812035714/lr2079sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035714/lr2079Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035714/lr2079Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2,4,5,6-tetramethyl-1-benzofuran derivatives containing 3-phenylsulfinyl (Seo et al., 2011a) and 3-(3-fluorophenylsulfinyl) (Seo et al., 2011b) 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 0.017 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 2-fluorophenyl ring and the mean plane of the benzofuran ring is 85.45 (4)°. In the crystal structure (Fig. 2), molecules are connected by weak C–H···O and C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids -of the C2–C7 benzene ring and the C13–C18 2-fluorophenyl ring, respectively).

Related literature top

For background information and the crystal structures of related compounds, see: Seo et al. (2011a,b).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(2-fluorophenylsulfanyl)-2,4,5,6-tetramethyl-1-benzofuran (330 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 63%, m.p. 464–465 K; R_f = 0.63 (hexane–ethyl acetate, 4:1 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 the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x, - y +1/2, z +1/2 (ii) x, y - 1, z (iii) - x, y + 1/2, - z + 1/2 (iv) x, - y + 1/2, z - 1/2 (v) x, y + 1, z (vi) - x, y - 1/2, - z + 1/2.]

3-(2-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-1-benzofuran top

Crystal data top

C₁₈H₁₇FO₂S	F(000) = 664
M_r = 316.38	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7371 reflections
a = 14.6851 (4) Å	θ = 2.4–28.3°
b = 6.0786 (2) Å	µ = 0.23 mm⁻¹
c = 17.1647 (4) Å	T = 173 K
β = 102.223 (1)°	Block, colourless
V = 1497.47 (7) Å³	0.33 × 0.30 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3264 independent reflections
Radiation source: rotating anode	2803 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.043
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.4°
ϕ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −7→7
T_min = 0.593, T_max = 0.746	l = −21→21
24418 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 = 1.08	w = 1/[σ²(F_o²) + (0.0453P)² + 0.658P] where P = (F_o² + 2F_c²)/3
3264 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₈H₁₇FO₂S	V = 1497.47 (7) Å³
M_r = 316.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6851 (4) Å	µ = 0.23 mm⁻¹
b = 6.0786 (2) Å	T = 173 K
c = 17.1647 (4) Å	0.33 × 0.30 × 0.07 mm
β = 102.223 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3264 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2803 reflections with I > 2σ(I)
T_min = 0.593, T_max = 0.746	R_int = 0.043
24418 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	Δρ_max = 0.28 e Å⁻³
3264 reflections	Δρ_min = −0.40 e Å⁻³
203 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	0.21698 (3)	0.16904 (7)	0.41644 (2)	0.03042 (13)
F1	0.03896 (7)	0.32249 (18)	0.45203 (6)	0.0416 (3)
O1	0.23316 (7)	0.20829 (17)	0.64475 (6)	0.0281 (3)
O2	0.29956 (9)	0.1670 (2)	0.37937 (7)	0.0404 (3)
C1	0.24718 (11)	0.2438 (2)	0.51761 (9)	0.0252 (3)
C2	0.29950 (10)	0.4245 (2)	0.56249 (9)	0.0220 (3)
C3	0.35600 (10)	0.5993 (2)	0.54765 (9)	0.0227 (3)
C4	0.39264 (10)	0.7410 (2)	0.61115 (9)	0.0237 (3)
C5	0.37560 (10)	0.7064 (2)	0.68833 (9)	0.0243 (3)
C6	0.32286 (10)	0.5281 (3)	0.70348 (9)	0.0254 (3)
H6	0.3123	0.5001	0.7553	0.030*
C7	0.28666 (10)	0.3939 (2)	0.63998 (9)	0.0233 (3)
C8	0.21110 (10)	0.1214 (2)	0.56972 (10)	0.0272 (3)
C9	0.37842 (12)	0.6310 (3)	0.46666 (9)	0.0300 (3)
H9A	0.3410	0.7522	0.4390	0.045*
H9B	0.3641	0.4956	0.4355	0.045*
H9C	0.4447	0.6657	0.4729	0.045*
C10	0.45310 (11)	0.9320 (3)	0.59733 (10)	0.0322 (4)
H10A	0.5185	0.8857	0.6083	0.048*
H10B	0.4455	1.0536	0.6329	0.048*
H10C	0.4346	0.9807	0.5418	0.048*
C11	0.41622 (11)	0.8586 (3)	0.75636 (10)	0.0317 (4)
H11A	0.4009	0.8035	0.8057	0.048*
H11B	0.3900	1.0063	0.7450	0.048*
H11C	0.4841	0.8648	0.7626	0.048*
C12	0.15203 (12)	−0.0779 (3)	0.56170 (12)	0.0372 (4)
H12A	0.1433	−0.1347	0.5072	0.056*
H12B	0.0913	−0.0408	0.5733	0.056*
H12C	0.1824	−0.1902	0.5993	0.056*
C13	0.15085 (11)	0.4095 (3)	0.37763 (9)	0.0272 (3)
C14	0.06721 (11)	0.4548 (3)	0.39837 (9)	0.0295 (3)
C15	0.01129 (12)	0.6277 (3)	0.36623 (10)	0.0364 (4)
H15	−0.0459	0.6556	0.3818	0.044*
C16	0.04042 (13)	0.7601 (3)	0.31056 (11)	0.0398 (4)
H16	0.0033	0.8814	0.2880	0.048*
C17	0.12312 (13)	0.7163 (3)	0.28783 (10)	0.0390 (4)
H17	0.1426	0.8078	0.2495	0.047*
C18	0.17811 (12)	0.5402 (3)	0.32034 (10)	0.0338 (4)
H18	0.2343	0.5089	0.3035	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0325 (2)	0.0273 (2)	0.0304 (2)	0.00289 (16)	0.00422 (17)	−0.00763 (15)
F1	0.0326 (6)	0.0485 (6)	0.0465 (6)	−0.0011 (4)	0.0151 (5)	0.0097 (5)
O1	0.0284 (6)	0.0253 (5)	0.0309 (6)	−0.0028 (4)	0.0073 (5)	0.0056 (4)
O2	0.0386 (7)	0.0465 (7)	0.0376 (7)	0.0107 (6)	0.0114 (6)	−0.0102 (6)
C1	0.0249 (8)	0.0223 (7)	0.0276 (8)	0.0023 (6)	0.0036 (6)	−0.0011 (6)
C2	0.0214 (7)	0.0218 (7)	0.0227 (7)	0.0033 (6)	0.0044 (6)	0.0013 (5)
C3	0.0209 (7)	0.0236 (7)	0.0243 (8)	0.0028 (6)	0.0063 (6)	0.0027 (5)
C4	0.0204 (7)	0.0238 (7)	0.0274 (8)	0.0018 (6)	0.0062 (6)	0.0027 (6)
C5	0.0210 (7)	0.0271 (7)	0.0241 (8)	0.0033 (6)	0.0032 (6)	0.0005 (6)
C6	0.0253 (7)	0.0305 (8)	0.0210 (7)	0.0036 (6)	0.0065 (6)	0.0045 (6)
C7	0.0202 (7)	0.0225 (7)	0.0278 (8)	0.0000 (6)	0.0065 (6)	0.0057 (6)
C8	0.0234 (8)	0.0234 (7)	0.0332 (8)	0.0010 (6)	0.0024 (6)	0.0012 (6)
C9	0.0331 (9)	0.0327 (8)	0.0258 (8)	−0.0011 (7)	0.0099 (7)	0.0024 (6)
C10	0.0307 (8)	0.0312 (8)	0.0356 (9)	−0.0071 (7)	0.0089 (7)	−0.0005 (7)
C11	0.0329 (9)	0.0338 (9)	0.0276 (8)	−0.0007 (7)	0.0042 (7)	−0.0039 (7)
C12	0.0355 (9)	0.0257 (8)	0.0497 (11)	−0.0055 (7)	0.0075 (8)	0.0027 (7)
C13	0.0264 (8)	0.0301 (8)	0.0233 (8)	−0.0002 (6)	0.0012 (6)	−0.0055 (6)
C14	0.0274 (8)	0.0339 (8)	0.0265 (8)	−0.0031 (6)	0.0042 (6)	−0.0028 (6)
C15	0.0307 (9)	0.0419 (9)	0.0354 (9)	0.0064 (7)	0.0039 (7)	−0.0050 (7)
C16	0.0438 (11)	0.0342 (9)	0.0359 (9)	0.0043 (8)	−0.0037 (8)	−0.0001 (7)
C17	0.0448 (11)	0.0409 (10)	0.0283 (9)	−0.0078 (8)	0.0008 (8)	0.0046 (7)
C18	0.0298 (9)	0.0446 (10)	0.0263 (8)	−0.0036 (7)	0.0041 (7)	−0.0024 (7)

Geometric parameters (Å, º) top

S1—O2	1.4839 (13)	C9—H9C	0.9800
S1—C1	1.7587 (16)	C10—H10A	0.9800
S1—C13	1.8028 (16)	C10—H10B	0.9800
F1—C14	1.3524 (19)	C10—H10C	0.9800
O1—C8	1.3660 (19)	C11—H11A	0.9800
O1—C7	1.3869 (17)	C11—H11B	0.9800
C1—C8	1.355 (2)	C11—H11C	0.9800
C1—C2	1.463 (2)	C12—H12A	0.9800
C2—C7	1.395 (2)	C12—H12B	0.9800
C2—C3	1.404 (2)	C12—H12C	0.9800
C3—C4	1.404 (2)	C13—C14	1.377 (2)
C3—C9	1.507 (2)	C13—C18	1.387 (2)
C4—C5	1.415 (2)	C14—C15	1.375 (2)
C4—C10	1.511 (2)	C15—C16	1.384 (3)
C5—C6	1.389 (2)	C15—H15	0.9500
C5—C11	1.510 (2)	C16—C17	1.378 (3)
C6—C7	1.375 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.386 (3)
C8—C12	1.479 (2)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800

O2—S1—C1	111.56 (7)	C4—C10—H10B	109.5
O2—S1—C13	105.88 (8)	H10A—C10—H10B	109.5
C1—S1—C13	99.13 (7)	C4—C10—H10C	109.5
C8—O1—C7	106.45 (12)	H10A—C10—H10C	109.5
C8—C1—C2	107.46 (13)	H10B—C10—H10C	109.5
C8—C1—S1	117.25 (12)	C5—C11—H11A	109.5
C2—C1—S1	135.13 (12)	C5—C11—H11B	109.5
C7—C2—C3	118.58 (13)	H11A—C11—H11B	109.5
C7—C2—C1	103.89 (13)	C5—C11—H11C	109.5
C3—C2—C1	137.49 (14)	H11A—C11—H11C	109.5
C4—C3—C2	117.87 (13)	H11B—C11—H11C	109.5
C4—C3—C9	120.99 (13)	C8—C12—H12A	109.5
C2—C3—C9	121.13 (14)	C8—C12—H12B	109.5
C3—C4—C5	121.39 (14)	H12A—C12—H12B	109.5
C3—C4—C10	119.42 (14)	C8—C12—H12C	109.5
C5—C4—C10	119.18 (14)	H12A—C12—H12C	109.5
C6—C5—C4	120.50 (14)	H12B—C12—H12C	109.5
C6—C5—C11	118.57 (14)	C14—C13—C18	118.43 (15)
C4—C5—C11	120.91 (14)	C14—C13—S1	120.45 (13)
C7—C6—C5	116.88 (14)	C18—C13—S1	120.81 (13)
C7—C6—H6	121.6	F1—C14—C15	118.99 (15)
C5—C6—H6	121.6	F1—C14—C13	118.43 (14)
C6—C7—O1	124.37 (13)	C15—C14—C13	122.58 (16)
C6—C7—C2	124.69 (14)	C14—C15—C16	118.40 (17)
O1—C7—C2	110.94 (13)	C14—C15—H15	120.8
C1—C8—O1	111.23 (13)	C16—C15—H15	120.8
C1—C8—C12	133.80 (16)	C17—C16—C15	120.20 (17)
O1—C8—C12	114.94 (14)	C17—C16—H16	119.9
C3—C9—H9A	109.5	C15—C16—H16	119.9
C3—C9—H9B	109.5	C16—C17—C18	120.57 (17)
H9A—C9—H9B	109.5	C16—C17—H17	119.7
C3—C9—H9C	109.5	C18—C17—H17	119.7
H9A—C9—H9C	109.5	C17—C18—C13	119.79 (16)
H9B—C9—H9C	109.5	C17—C18—H18	120.1
C4—C10—H10A	109.5	C13—C18—H18	120.1

O2—S1—C1—C8	−134.50 (13)	C3—C2—C7—C6	2.4 (2)
C13—S1—C1—C8	114.31 (13)	C1—C2—C7—C6	−179.26 (14)
O2—S1—C1—C2	50.87 (17)	C3—C2—C7—O1	−176.94 (12)
C13—S1—C1—C2	−60.32 (17)	C1—C2—C7—O1	1.35 (16)
C8—C1—C2—C7	−1.67 (16)	C2—C1—C8—O1	1.44 (17)
S1—C1—C2—C7	173.33 (13)	S1—C1—C8—O1	−174.59 (10)
C8—C1—C2—C3	176.11 (17)	C2—C1—C8—C12	179.33 (16)
S1—C1—C2—C3	−8.9 (3)	S1—C1—C8—C12	3.3 (2)
C7—C2—C3—C4	−3.3 (2)	C7—O1—C8—C1	−0.60 (17)
C1—C2—C3—C4	179.19 (16)	C7—O1—C8—C12	−178.92 (13)
C7—C2—C3—C9	175.39 (14)	O2—S1—C13—C14	177.56 (12)
C1—C2—C3—C9	−2.1 (3)	C1—S1—C13—C14	−66.81 (14)
C2—C3—C4—C5	1.7 (2)	O2—S1—C13—C18	4.09 (15)
C9—C3—C4—C5	−176.96 (14)	C1—S1—C13—C18	119.73 (13)
C2—C3—C4—C10	−179.50 (13)	C18—C13—C14—F1	177.57 (14)
C9—C3—C4—C10	1.8 (2)	S1—C13—C14—F1	3.9 (2)
C3—C4—C5—C6	0.9 (2)	C18—C13—C14—C15	−1.9 (2)
C10—C4—C5—C6	−177.87 (14)	S1—C13—C14—C15	−175.52 (13)
C3—C4—C5—C11	179.36 (13)	F1—C14—C15—C16	−179.13 (15)
C10—C4—C5—C11	0.6 (2)	C13—C14—C15—C16	0.3 (3)
C4—C5—C6—C7	−1.8 (2)	C14—C15—C16—C17	0.7 (3)
C11—C5—C6—C7	179.67 (13)	C15—C16—C17—C18	−0.1 (3)
C5—C6—C7—O1	179.48 (13)	C16—C17—C18—C13	−1.5 (3)
C5—C6—C7—C2	0.2 (2)	C14—C13—C18—C17	2.4 (2)
C8—O1—C7—C6	−179.93 (14)	S1—C13—C18—C17	176.04 (13)
C8—O1—C7—C2	−0.54 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C13–C18 2-fluorophenyl ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.40	3.3279 (19)	165
C12—H12C···Cg1ⁱⁱ	0.98	2.69	3.486 (2)	138
C16—H16···Cg2ⁱⁱⁱ	0.95	2.70	3.553 (2)	149

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FO₂S
M_r	316.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.6851 (4), 6.0786 (2), 17.1647 (4)
β (°)	102.223 (1)
V (Å³)	1497.47 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.33 × 0.30 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.593, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	24418, 3264, 2803
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.08
No. of reflections	3264
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.40

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 and Cg2 are the centroids of the C2–C7 benzene ring and the C13–C18 2-fluorophenyl ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.40	3.3279 (19)	164.7
C12—H12C···Cg1ⁱⁱ	0.98	2.69	3.486 (2)	138.4
C16—H16···Cg2ⁱⁱⁱ	0.95	2.70	3.553 (2)	148.6

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

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
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. (2011a). Acta Cryst. E67, o1512. Web of Science CSD CrossRef IUCr Journals Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o2327. 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 9| September 2012| Page o2742

doi:10.1107/S1600536812035714

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