2-(4-Fluoro­phen­yl)-1-(phenyl­sulfin­yl)­naphtho­[2,1-b]furan

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

doi:10.1107/S1600536811034155

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2479

doi:10.1107/S1600536811034155

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2-(4-Fluorophenyl)-1-(phenylsulfinyl)naphtho[2,1-b]furan

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 17 August 2011; accepted 20 August 2011; online 27 August 2011)

In the title compound, C₂₄H₁₅FO₂S, the 4-fluorophenyl ring makes a dihedral angle of 19.43 (4)° with the mean plane of the naphthofuran fragment. The dihedral angle between the phenyl ring and the mean plane of the naphthofuran fragment is 85.83 (4)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ); Hagiwara et al. (1999 ); Piloto et al. (2005 ). For structural studies of related 2-aryl-1-(phenylsulfinyl)naphtho[2,1-b]furan derivatives, see: Choi et al. (2009a ,b ).

Experimental

Crystal data

C₂₄H₁₅FO₂S
M_r = 386.42
Triclinic, $[P \overline 1]$
a = 7.2853 (2) Å
b = 10.1619 (3) Å
c = 12.3137 (4) Å
α = 103.439 (2)°
β = 90.486 (2)°
γ = 96.422 (2)°
V = 880.53 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.29 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.941, T_max = 0.954
16660 measured reflections
4392 independent reflections
3675 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.05
4392 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O2ⁱ	0.95	2.53	3.277 (2)	136
Symmetry code: (i) x-1, y, z.

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/S1600536811034155/qm2024sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034155/qm2024Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034155/qm2024Isup3.cml

checkCIF report

Comment top

Many compounds containing a naphthofuran moiety have drawn much attention owing to their valuable biological properties (Goel & Dixit, 2004; Hagiwara et al., 1999; Piloto et al., 2005). As a part of our ongoing studies of the substituent effect on the solid state structures of 2–aryl–1–(phenylsulfinyl)naphtho[2,1–b]furan analogues (Choi et al., 2009a,b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.291 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The 4–fluorophenyl ring makes the dihedral angle of 19.43 (4)° with the mean plane of the naphthofuran fragment. The diheral angle formed by the phenyl ring and the mean plane of the naphthofuran fragment is 85.83 (4)°. The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds between a phenyl H atom and the O atom of the sulfinyl group (Table 1; C23—H23···O2ⁱ).

Related literature top

For the pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004); Hagiwara et al. (1999); Piloto et al. (2005). For structural studies of related 2–aryl–1–(phenylsulfinyl)naphtho[2,1–b]furan derivatives, see: Choi et al. (2009a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2–(4–fluorophenyl)–1–(phenylsulfanyl)naphtho [2,1-b]furan (333 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 andconcentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 65%, m.p. 473–474 K; Rf = 0.46 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X–ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene 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.

2-(4-Fluorophenyl)-1-(phenylsulfinyl)naphtho[2,1-b]furan top

Crystal data top

C₂₄H₁₅FO₂S	Z = 2
M_r = 386.42	F(000) = 400
Triclinic, P1	D_x = 1.457 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2853 (2) Å	Cell parameters from 5489 reflections
b = 10.1619 (3) Å	θ = 2.8–28.2°
c = 12.3137 (4) Å	µ = 0.21 mm⁻¹
α = 103.439 (2)°	T = 173 K
β = 90.486 (2)°	Block, colourless
γ = 96.422 (2)°	0.29 × 0.26 × 0.22 mm
V = 880.53 (5) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	4392 independent reflections
Radiation source: rotating anode	3675 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.037
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.7°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.941, T_max = 0.954	l = −16→16
16660 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.055P)² + 0.2885P] where P = (F_o² + 2F_c²)/3
4392 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₁₅FO₂S	γ = 96.422 (2)°
M_r = 386.42	V = 880.53 (5) Å³
Triclinic, P1	Z = 2
a = 7.2853 (2) Å	Mo Kα radiation
b = 10.1619 (3) Å	µ = 0.21 mm⁻¹
c = 12.3137 (4) Å	T = 173 K
α = 103.439 (2)°	0.29 × 0.26 × 0.22 mm
β = 90.486 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4392 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3675 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.954	R_int = 0.037
16660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	Δρ_max = 0.38 e Å⁻³
4392 reflections	Δρ_min = −0.33 e Å⁻³
253 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	0.45928 (5)	0.63116 (4)	0.30349 (3)	0.02511 (11)
O1	0.20787 (15)	0.47766 (10)	0.53486 (8)	0.0251 (2)
O2	0.60815 (15)	0.55620 (12)	0.24620 (9)	0.0325 (3)
F1	0.30192 (18)	1.08991 (10)	0.78434 (9)	0.0525 (3)
C1	0.3299 (2)	0.52987 (14)	0.38112 (11)	0.0227 (3)
C2	0.2802 (2)	0.38352 (14)	0.35730 (12)	0.0232 (3)
C3	0.2860 (2)	0.27066 (14)	0.26339 (12)	0.0241 (3)
C4	0.3429 (2)	0.28088 (15)	0.15649 (12)	0.0284 (3)
H4	0.3837	0.3678	0.1435	0.034*
C5	0.3403 (3)	0.16705 (17)	0.07079 (13)	0.0350 (4)
H5	0.3778	0.1759	−0.0011	0.042*
C6	0.2828 (3)	0.03789 (17)	0.08849 (14)	0.0396 (4)
H6	0.2823	−0.0404	0.0287	0.047*
C7	0.2276 (3)	0.02390 (16)	0.19071 (14)	0.0363 (4)
H7	0.1896	−0.0645	0.2017	0.044*
C8	0.2257 (2)	0.13876 (15)	0.28111 (13)	0.0277 (3)
C9	0.1638 (2)	0.12265 (16)	0.38691 (13)	0.0307 (3)
H9	0.1278	0.0334	0.3966	0.037*
C10	0.1545 (2)	0.23082 (15)	0.47463 (13)	0.0285 (3)
H10	0.1118	0.2198	0.5450	0.034*
C11	0.2112 (2)	0.35935 (14)	0.45543 (12)	0.0244 (3)
C13	0.2903 (2)	0.71658 (15)	0.56465 (11)	0.0246 (3)
C14	0.3198 (2)	0.83664 (15)	0.52753 (13)	0.0292 (3)
H14	0.3354	0.8320	0.4503	0.035*
C15	0.3266 (2)	0.96241 (16)	0.60182 (14)	0.0327 (3)
H15	0.3505	1.0441	0.5768	0.039*
C16	0.2981 (2)	0.96647 (16)	0.71221 (14)	0.0346 (4)
C17	0.2644 (3)	0.85122 (18)	0.75213 (13)	0.0376 (4)
H17	0.2433	0.8575	0.8291	0.045*
C18	0.2618 (2)	0.72569 (16)	0.67816 (12)	0.0315 (3)
H18	0.2404	0.6449	0.7047	0.038*
C19	0.2902 (2)	0.63310 (14)	0.19726 (12)	0.0243 (3)
C12	0.2825 (2)	0.58147 (14)	0.48933 (12)	0.0238 (3)
C20	0.3553 (2)	0.63478 (15)	0.09205 (12)	0.0284 (3)
H20	0.4813	0.6249	0.0766	0.034*
C21	0.2352 (2)	0.65096 (16)	0.00974 (13)	0.0341 (4)
H21	0.2779	0.6505	−0.0630	0.041*
C22	0.0532 (2)	0.66772 (17)	0.03334 (15)	0.0365 (4)
H22	−0.0281	0.6813	−0.0228	0.044*
C23	−0.0115 (2)	0.66481 (16)	0.13781 (15)	0.0352 (4)
H23	−0.1373	0.6754	0.1531	0.042*
C24	0.1062 (2)	0.64650 (15)	0.22047 (13)	0.0297 (3)
H24	0.0616	0.6431	0.2922	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02566 (19)	0.02638 (19)	0.02358 (18)	0.00069 (14)	0.00323 (13)	0.00750 (13)
O1	0.0290 (5)	0.0258 (5)	0.0215 (5)	0.0044 (4)	0.0048 (4)	0.0068 (4)
O2	0.0266 (6)	0.0420 (6)	0.0325 (6)	0.0091 (5)	0.0074 (5)	0.0135 (5)
F1	0.0772 (8)	0.0330 (5)	0.0407 (6)	0.0154 (5)	−0.0018 (6)	−0.0089 (4)
C1	0.0234 (7)	0.0237 (6)	0.0214 (6)	0.0024 (5)	0.0024 (5)	0.0064 (5)
C2	0.0213 (6)	0.0250 (7)	0.0242 (7)	0.0029 (5)	0.0002 (5)	0.0074 (5)
C3	0.0223 (7)	0.0248 (7)	0.0252 (7)	0.0037 (5)	0.0000 (5)	0.0052 (5)
C4	0.0328 (8)	0.0270 (7)	0.0255 (7)	0.0038 (6)	0.0011 (6)	0.0062 (6)
C5	0.0454 (10)	0.0336 (8)	0.0247 (7)	0.0057 (7)	0.0028 (7)	0.0039 (6)
C6	0.0537 (11)	0.0273 (8)	0.0322 (8)	0.0022 (8)	−0.0007 (8)	−0.0027 (6)
C7	0.0447 (10)	0.0239 (7)	0.0377 (9)	0.0003 (7)	−0.0002 (7)	0.0040 (6)
C8	0.0266 (7)	0.0262 (7)	0.0300 (7)	0.0030 (6)	−0.0008 (6)	0.0064 (6)
C9	0.0310 (8)	0.0261 (7)	0.0367 (8)	0.0004 (6)	0.0023 (7)	0.0122 (6)
C10	0.0279 (7)	0.0313 (7)	0.0293 (7)	0.0037 (6)	0.0054 (6)	0.0131 (6)
C11	0.0236 (7)	0.0257 (7)	0.0240 (7)	0.0045 (6)	0.0023 (5)	0.0054 (5)
C13	0.0226 (7)	0.0275 (7)	0.0232 (7)	0.0057 (6)	0.0011 (5)	0.0039 (5)
C14	0.0318 (8)	0.0289 (7)	0.0265 (7)	0.0045 (6)	0.0044 (6)	0.0048 (6)
C15	0.0331 (8)	0.0261 (7)	0.0378 (8)	0.0038 (6)	0.0021 (7)	0.0048 (6)
C16	0.0377 (9)	0.0287 (8)	0.0328 (8)	0.0102 (7)	−0.0034 (7)	−0.0051 (6)
C17	0.0506 (10)	0.0412 (9)	0.0218 (7)	0.0167 (8)	0.0005 (7)	0.0036 (6)
C18	0.0396 (9)	0.0322 (8)	0.0243 (7)	0.0109 (7)	0.0002 (6)	0.0069 (6)
C19	0.0273 (7)	0.0208 (6)	0.0254 (7)	0.0032 (5)	0.0015 (6)	0.0064 (5)
C12	0.0228 (7)	0.0265 (7)	0.0233 (6)	0.0033 (6)	0.0009 (5)	0.0084 (5)
C20	0.0282 (7)	0.0304 (7)	0.0281 (7)	0.0041 (6)	0.0045 (6)	0.0096 (6)
C21	0.0400 (9)	0.0350 (8)	0.0292 (8)	0.0010 (7)	0.0007 (7)	0.0129 (6)
C22	0.0361 (9)	0.0332 (8)	0.0409 (9)	0.0022 (7)	−0.0092 (7)	0.0112 (7)
C23	0.0258 (8)	0.0317 (8)	0.0475 (9)	0.0041 (6)	0.0004 (7)	0.0082 (7)
C24	0.0299 (8)	0.0270 (7)	0.0319 (8)	0.0044 (6)	0.0062 (6)	0.0058 (6)

Geometric parameters (Å, º) top

S1—O2	1.4840 (11)	C10—H10	0.9500
S1—C1	1.7655 (15)	C13—C14	1.395 (2)
S1—C19	1.7939 (15)	C13—C18	1.398 (2)
O1—C11	1.3650 (16)	C13—C12	1.4623 (19)
O1—C12	1.3690 (17)	C14—C15	1.384 (2)
F1—C16	1.3554 (17)	C14—H14	0.9500
C1—C12	1.3761 (19)	C15—C16	1.369 (2)
C1—C2	1.4505 (19)	C15—H15	0.9500
C2—C11	1.376 (2)	C16—C17	1.371 (2)
C2—C3	1.4316 (19)	C17—C18	1.383 (2)
C3—C4	1.407 (2)	C17—H17	0.9500
C3—C8	1.429 (2)	C18—H18	0.9500
C4—C5	1.371 (2)	C19—C20	1.387 (2)
C4—H4	0.9500	C19—C24	1.388 (2)
C5—C6	1.399 (2)	C20—C21	1.384 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.358 (2)	C21—C22	1.380 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.415 (2)	C22—C23	1.379 (3)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.421 (2)	C23—C24	1.384 (2)
C9—C10	1.359 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C10—C11	1.399 (2)

O2—S1—C1	109.66 (7)	C14—C13—C12	122.77 (13)
O2—S1—C19	106.56 (7)	C18—C13—C12	118.58 (14)
C1—S1—C19	100.32 (7)	C15—C14—C13	120.83 (14)
C11—O1—C12	107.08 (11)	C15—C14—H14	119.6
C12—C1—C2	106.96 (12)	C13—C14—H14	119.6
C12—C1—S1	122.10 (11)	C16—C15—C14	118.52 (15)
C2—C1—S1	130.23 (11)	C16—C15—H15	120.7
C11—C2—C3	118.81 (13)	C14—C15—H15	120.7
C11—C2—C1	104.59 (12)	F1—C16—C15	118.28 (15)
C3—C2—C1	136.60 (13)	F1—C16—C17	119.01 (15)
C4—C3—C8	118.60 (13)	C15—C16—C17	122.71 (14)
C4—C3—C2	124.99 (13)	C16—C17—C18	118.67 (15)
C8—C3—C2	116.40 (13)	C16—C17—H17	120.7
C5—C4—C3	120.89 (15)	C18—C17—H17	120.7
C5—C4—H4	119.6	C17—C18—C13	120.61 (15)
C3—C4—H4	119.6	C17—C18—H18	119.7
C4—C5—C6	120.45 (15)	C13—C18—H18	119.7
C4—C5—H5	119.8	C20—C19—C24	120.76 (14)
C6—C5—H5	119.8	C20—C19—S1	116.63 (12)
C7—C6—C5	120.35 (15)	C24—C19—S1	122.28 (11)
C7—C6—H6	119.8	O1—C12—C1	109.83 (12)
C5—C6—H6	119.8	O1—C12—C13	114.08 (12)
C6—C7—C8	121.09 (15)	C1—C12—C13	136.09 (14)
C6—C7—H7	119.5	C21—C20—C19	119.39 (15)
C8—C7—H7	119.5	C21—C20—H20	120.3
C7—C8—C9	120.40 (14)	C19—C20—H20	120.3
C7—C8—C3	118.61 (14)	C22—C21—C20	120.00 (15)
C9—C8—C3	120.99 (13)	C22—C21—H21	120.0
C10—C9—C8	122.07 (14)	C20—C21—H21	120.0
C10—C9—H9	119.0	C23—C22—C21	120.45 (15)
C8—C9—H9	119.0	C23—C22—H22	119.8
C9—C10—C11	116.22 (14)	C21—C22—H22	119.8
C9—C10—H10	121.9	C22—C23—C24	120.23 (15)
C11—C10—H10	121.9	C22—C23—H23	119.9
O1—C11—C2	111.49 (12)	C24—C23—H23	119.9
O1—C11—C10	123.09 (13)	C23—C24—C19	119.14 (15)
C2—C11—C10	125.40 (13)	C23—C24—H24	120.4
C14—C13—C18	118.63 (13)	C19—C24—H24	120.4

O2—S1—C1—C12	134.17 (12)	C9—C10—C11—C2	−2.3 (2)
C19—S1—C1—C12	−113.94 (13)	C18—C13—C14—C15	2.0 (2)
O2—S1—C1—C2	−34.89 (15)	C12—C13—C14—C15	−179.88 (14)
C19—S1—C1—C2	77.00 (14)	C13—C14—C15—C16	−2.0 (2)
C12—C1—C2—C11	−1.64 (16)	C14—C15—C16—F1	−178.94 (15)
S1—C1—C2—C11	168.69 (12)	C14—C15—C16—C17	0.4 (3)
C12—C1—C2—C3	178.01 (16)	F1—C16—C17—C18	−179.64 (15)
S1—C1—C2—C3	−11.7 (3)	C15—C16—C17—C18	1.0 (3)
C11—C2—C3—C4	176.20 (14)	C16—C17—C18—C13	−0.9 (3)
C1—C2—C3—C4	−3.4 (3)	C14—C13—C18—C17	−0.6 (2)
C11—C2—C3—C8	−2.6 (2)	C12—C13—C18—C17	−178.74 (15)
C1—C2—C3—C8	177.77 (15)	O2—S1—C19—C20	−31.41 (13)
C8—C3—C4—C5	0.2 (2)	C1—S1—C19—C20	−145.68 (12)
C2—C3—C4—C5	−178.65 (15)	O2—S1—C19—C24	155.11 (12)
C3—C4—C5—C6	−0.7 (3)	C1—S1—C19—C24	40.84 (13)
C4—C5—C6—C7	0.5 (3)	C11—O1—C12—C1	1.02 (16)
C5—C6—C7—C8	0.4 (3)	C11—O1—C12—C13	−179.62 (12)
C6—C7—C8—C9	178.66 (16)	C2—C1—C12—O1	0.40 (16)
C6—C7—C8—C3	−1.0 (3)	S1—C1—C12—O1	−170.89 (10)
C4—C3—C8—C7	0.7 (2)	C2—C1—C12—C13	−178.75 (16)
C2—C3—C8—C7	179.59 (14)	S1—C1—C12—C13	10.0 (2)
C4—C3—C8—C9	−178.94 (14)	C14—C13—C12—O1	−164.53 (14)
C2—C3—C8—C9	0.0 (2)	C18—C13—C12—O1	13.57 (19)
C7—C8—C9—C10	−177.87 (16)	C14—C13—C12—C1	14.6 (3)
C3—C8—C9—C10	1.7 (2)	C18—C13—C12—C1	−167.30 (17)
C8—C9—C10—C11	−0.7 (2)	C24—C19—C20—C21	0.4 (2)
C12—O1—C11—C2	−2.16 (16)	S1—C19—C20—C21	−173.16 (12)
C12—O1—C11—C10	176.51 (14)	C19—C20—C21—C22	1.2 (2)
C3—C2—C11—O1	−177.37 (12)	C20—C21—C22—C23	−1.8 (2)
C1—C2—C11—O1	2.34 (16)	C21—C22—C23—C24	0.7 (3)
C3—C2—C11—C10	4.0 (2)	C22—C23—C24—C19	0.9 (2)
C1—C2—C11—C10	−176.29 (14)	C20—C19—C24—C23	−1.5 (2)
C9—C10—C11—O1	179.24 (13)	S1—C19—C24—C23	171.74 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O2ⁱ	0.95	2.53	3.277 (2)	136

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅FO₂S
M_r	386.42
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.2853 (2), 10.1619 (3), 12.3137 (4)
α, β, γ (°)	103.439 (2), 90.486 (2), 96.422 (2)
V (Å³)	880.53 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.29 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.941, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	16660, 4392, 3675
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.05
No. of reflections	4392
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.33

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
C23—H23···O2ⁱ	0.95	2.53	3.277 (2)	135.6

Symmetry code: (i) x−1, y, z.

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. (2009a). Acta Cryst. E65, o1443. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o2014. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Goel, A. & Dixit, M. (2004). Tetrahedron Lett. 45, 8819–8821. Web of Science CrossRef CAS Google Scholar
Hagiwara, H., Sato, K., Suzuki, T. & Ando, M. (1999). Heterocycles, 51, 497–500. CrossRef CAS Google Scholar
Piloto, A. M., Costa, S. P. G. & Goncalves, M. S. T. (2005). Tetrahedron Lett. 46, 4757–4760. Web of Science CrossRef CAS 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 67| Part 9| September 2011| Page o2479

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