3-Cyclo­pentyl­sulfonyl-5-fluoro-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811021222

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1689

doi:10.1107/S1600536811021222

Open

access

3-Cyclopentylsulfonyl-5-fluoro-2-methyl-1-benzofuran

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 30 May 2011; accepted 2 June 2011; online 18 June 2011)

There are two independent molecules, A and B, in the asymmetric unit of the title compound, C₁₄H₁₅FO₃S, in each of which the cyclopentyl ring adopts an envelope conformation. The benzofuran units in each molecule are essentially planar, with mean deviations from the least-squares plane defined by the nine constituent ring atoms of 0.009 (2) Å for molecule A and 0.013 (2) Å for molecule B. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds. In the cyclopentyl ring of molecule B, one C atom is disordered over two positions with site-occupancy factors of 0.60 (2) and 0.40 (2).

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 a structural study of the related compound 5-bromo-3-cyclopentylsulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011 ).

Experimental

Crystal data

C₁₄H₁₅FO₃S
M_r = 282.32
Triclinic, $[P \overline 1]$
a = 10.0568 (8) Å
b = 10.2697 (8) Å
c = 13.2894 (10) Å
α = 95.033 (4)°
β = 109.140 (4)°
γ = 91.229 (4)°
V = 1289.82 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 173 K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.936, T_max = 0.948
21777 measured reflections
5565 independent reflections
4022 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.03
5565 reflections
361 parameters
20 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O6ⁱ	0.98	2.45	3.348 (3)	152
C19—H19⋯O6ⁱⁱ	0.95	2.58	3.469 (3)	157
C23—H23A⋯O2ⁱⁱⁱ	0.98	2.50	3.318 (3)	141
Symmetry codes: (i) x-1, y-1, z; (ii) x-1, y, z; (iii) 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/S1600536811021222/go2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021222/go2016Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021222/go2016Isup3.cml

checkCIF report

Comment top

Many compounds having a benzofuran moiety have attracted much attention due to their valuable biological properties such as antifungal, antimicrobial, antitumor and antiviral 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 the substituent effect on the solid state structures of 3-cyclopentylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Seo et al., 2011), we report herein on the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. There are two independent unique molecules [labelled A & B] in which the benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å for A and 0.013 (2) Å for B, respectively, from the least-squares plane defined by the nine constituent atoms. The cyclopentyl rings of both molecules are in an envelope form. In the cyclopentyl ring of molecule B, C27 atom is disordered over two positions with site-occupancy factors, from refinement of 0.60 (2) (part 1) and 0.40 (8) (part 2). In the crystal packing (Fig. 2), molecules are linked by weak non-classical intermolecular C–H···O hydrogen bonds; the first one between a methyl H atom and the O atom of the sulfonyl group (Table 1; C9–H9C···O6ⁱ), the second one between a benzene H atom and the O atom of the sulfonyl group (Table 1; C19–H19···O6ⁱⁱ), and the third one between a methyl H atom and the O atom of the sulfonyl group (Table 1; C23–H23A···O2ⁱⁱⁱ).

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 a structural study of the related compound, 5-bromo-3-cyclopentylsulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011).

Experimental top

3-chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-cyclopentylsulfanyl-5-fluoro-2-methyl-1-benzofuran (325 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 71%, m.p. 394-395 K; R_f = 0.49 (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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the C–H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1, y - 1, z; (ii) x - 1, y, z; (iii) x + 1, y, z; (iv) x + 1, y + 1, z.]

3-Cyclopentylsulfonyl-5-fluoro-2-methyl-1-benzofuran top

Crystal data top

C₁₄H₁₅FO₃S	Z = 4
M_r = 282.32	F(000) = 592
Triclinic, P1	D_x = 1.454 Mg m⁻³
Hall symbol: -P 1	Melting point = 394–395 K
a = 10.0568 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2697 (8) Å	Cell parameters from 6383 reflections
c = 13.2894 (10) Å	θ = 2.2–28.1°
α = 95.033 (4)°	µ = 0.26 mm⁻¹
β = 109.140 (4)°	T = 173 K
γ = 91.229 (4)°	Block, colourless
V = 1289.82 (17) Å³	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	5565 independent reflections
Radiation source: rotating anode	4022 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.042
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.6°
ϕ and ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.936, T_max = 0.948	l = −16→16
21777 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0514P)² + 0.6137P] where P = (F_o² + 2F_c²)/3
5565 reflections	(Δ/σ)_max = 0.001
361 parameters	Δρ_max = 0.50 e Å⁻³
20 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₄H₁₅FO₃S	γ = 91.229 (4)°
M_r = 282.32	V = 1289.82 (17) Å³
Triclinic, P1	Z = 4
a = 10.0568 (8) Å	Mo Kα radiation
b = 10.2697 (8) Å	µ = 0.26 mm⁻¹
c = 13.2894 (10) Å	T = 173 K
α = 95.033 (4)°	0.26 × 0.24 × 0.20 mm
β = 109.140 (4)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5565 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4022 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.948	R_int = 0.042
21777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	20 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.50 e Å⁻³
5565 reflections	Δρ_min = −0.31 e Å⁻³
361 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	Occ. (<1)
S1	0.23453 (6)	0.33785 (5)	0.23641 (4)	0.03150 (15)
F1	0.81952 (14)	0.46170 (14)	0.28853 (11)	0.0484 (4)
O1	0.40319 (15)	0.10269 (14)	0.07061 (11)	0.0326 (4)
O2	0.09116 (17)	0.32983 (18)	0.16639 (13)	0.0460 (4)
C1	0.3369 (2)	0.2567 (2)	0.17088 (16)	0.0269 (4)
C2	0.4835 (2)	0.28575 (19)	0.18530 (15)	0.0252 (4)
O3	0.30185 (18)	0.46418 (15)	0.27859 (14)	0.0438 (4)
C3	0.5859 (2)	0.3822 (2)	0.24350 (16)	0.0296 (5)
H3	0.5664	0.4524	0.2872	0.036*
C4	0.7165 (2)	0.3693 (2)	0.23369 (17)	0.0311 (5)
C5	0.7522 (2)	0.2698 (2)	0.17204 (18)	0.0344 (5)
H5	0.8456	0.2666	0.1699	0.041*
C6	0.6504 (2)	0.1750 (2)	0.11357 (17)	0.0333 (5)
H6	0.6704	0.1051	0.0699	0.040*
C7	0.5185 (2)	0.1872 (2)	0.12172 (16)	0.0280 (5)
C8	0.2955 (2)	0.1465 (2)	0.10210 (16)	0.0305 (5)
C9	0.1621 (2)	0.0657 (2)	0.05858 (19)	0.0411 (6)
H9A	0.1435	0.0392	−0.0177	0.062*
H9B	0.0847	0.1166	0.0675	0.062*
H9C	0.1697	−0.0125	0.0971	0.062*
C10	0.2422 (2)	0.2431 (2)	0.34337 (17)	0.0310 (5)
H10	0.2079	0.1510	0.3140	0.037*
C11	0.3910 (3)	0.2436 (2)	0.42411 (18)	0.0396 (6)
H11A	0.4133	0.1548	0.4460	0.048*
H11B	0.4617	0.2748	0.3933	0.048*
C12	0.3888 (3)	0.3373 (3)	0.5190 (2)	0.0514 (7)
H12A	0.4612	0.3171	0.5860	0.062*
H12B	0.4047	0.4293	0.5070	0.062*
C13	0.2438 (3)	0.3130 (3)	0.5228 (2)	0.0510 (7)
H13A	0.2174	0.3868	0.5643	0.061*
H13B	0.2374	0.2315	0.5560	0.061*
C14	0.1491 (3)	0.3006 (2)	0.40645 (19)	0.0405 (6)
H14A	0.1171	0.3872	0.3839	0.049*
H14B	0.0654	0.2414	0.3954	0.049*
S2	0.97507 (6)	0.86902 (6)	0.24244 (5)	0.03691 (16)
F2	0.43771 (16)	0.96231 (15)	0.28861 (13)	0.0589 (4)
O4	0.67248 (16)	0.60770 (14)	0.08407 (12)	0.0359 (4)
O5	0.93729 (18)	1.00229 (16)	0.24654 (16)	0.0536 (5)
O6	1.07814 (18)	0.83460 (19)	0.19339 (15)	0.0534 (5)
C15	0.8217 (2)	0.7728 (2)	0.17896 (17)	0.0308 (5)
C16	0.6865 (2)	0.7948 (2)	0.19121 (16)	0.0290 (5)
C17	0.6327 (2)	0.8908 (2)	0.24526 (17)	0.0332 (5)
H17	0.6884	0.9657	0.2853	0.040*
C18	0.4942 (3)	0.8703 (2)	0.23702 (19)	0.0399 (6)
C19	0.4080 (3)	0.7648 (2)	0.1794 (2)	0.0424 (6)
H19	0.3129	0.7566	0.1776	0.051*
C20	0.4606 (2)	0.6713 (2)	0.12428 (19)	0.0387 (5)
H20	0.4039	0.5976	0.0830	0.046*
C21	0.5994 (2)	0.6900 (2)	0.13206 (17)	0.0312 (5)
C22	0.8073 (2)	0.6592 (2)	0.11486 (17)	0.0334 (5)
C23	0.9032 (3)	0.5815 (3)	0.0738 (2)	0.0456 (6)
H23A	0.9124	0.4962	0.1026	0.068*
H23B	0.9960	0.6279	0.0961	0.068*
H23C	0.8650	0.5686	−0.0045	0.068*
C24	1.0323 (2)	0.8246 (2)	0.37518 (18)	0.0367 (5)
H24	0.9527	0.8329	0.4044	0.044*
C25	1.1571 (3)	0.9139 (3)	0.4469 (2)	0.0526 (7)
H25A	1.2183	0.9408	0.4064	0.063*
H25B	1.1246	0.9932	0.4779	0.063*
C26	1.2325 (3)	0.8310 (2)	0.5315 (2)	0.0665 (9)
H26A	1.1804	0.8185	0.5819	0.080*	0.60 (2)
H26B	1.3293	0.8672	0.5719	0.080*	0.60 (2)
H26C	1.1987	0.8460	0.5934	0.080*	0.40 (2)
H26D	1.3349	0.8542	0.5562	0.080*	0.40 (2)
C27A	1.2327 (6)	0.7051 (8)	0.4620 (8)	0.060 (3)	0.60 (2)
H27A	1.3006	0.7139	0.4230	0.072*	0.60 (2)
H27B	1.2574	0.6306	0.5058	0.072*	0.60 (2)
C27B	1.1998 (14)	0.6866 (3)	0.4914 (7)	0.050 (3)	0.40 (2)
H27C	1.2837	0.6453	0.4824	0.060*	0.40 (2)
H27D	1.1679	0.6392	0.5419	0.060*	0.40 (2)
C28	1.0829 (3)	0.6861 (2)	0.3846 (2)	0.0429 (6)
H28A	1.0237	0.6318	0.4132	0.051*	0.60 (2)
H28B	1.0810	0.6439	0.3142	0.051*	0.60 (2)
H28C	1.012 (7)	0.612 (7)	0.354 (5)	0.051*	0.40 (2)
H28D	1.134 (8)	0.675 (7)	0.343 (5)	0.051*	0.40 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0255 (3)	0.0333 (3)	0.0406 (3)	0.0073 (2)	0.0156 (2)	0.0095 (2)
F1	0.0306 (8)	0.0513 (8)	0.0585 (9)	−0.0166 (6)	0.0147 (7)	−0.0158 (7)
O1	0.0280 (8)	0.0345 (8)	0.0335 (8)	−0.0066 (6)	0.0106 (7)	−0.0059 (6)
O2	0.0253 (9)	0.0664 (12)	0.0505 (10)	0.0139 (8)	0.0136 (8)	0.0204 (9)
C1	0.0210 (10)	0.0323 (11)	0.0289 (11)	0.0036 (8)	0.0093 (8)	0.0064 (9)
C2	0.0241 (11)	0.0269 (10)	0.0266 (10)	0.0031 (8)	0.0103 (8)	0.0048 (8)
O3	0.0478 (10)	0.0284 (8)	0.0672 (11)	0.0050 (7)	0.0350 (9)	0.0058 (8)
C3	0.0292 (12)	0.0291 (11)	0.0305 (11)	−0.0005 (9)	0.0112 (9)	−0.0016 (9)
C4	0.0240 (11)	0.0318 (11)	0.0347 (11)	−0.0067 (9)	0.0073 (9)	−0.0002 (9)
C5	0.0247 (11)	0.0387 (12)	0.0418 (13)	0.0011 (9)	0.0139 (10)	0.0036 (10)
C6	0.0328 (12)	0.0321 (11)	0.0370 (12)	0.0025 (9)	0.0160 (10)	−0.0029 (9)
C7	0.0267 (11)	0.0287 (11)	0.0272 (10)	−0.0035 (9)	0.0079 (9)	0.0003 (8)
C8	0.0237 (11)	0.0380 (12)	0.0295 (11)	−0.0011 (9)	0.0079 (9)	0.0050 (9)
C9	0.0302 (13)	0.0490 (14)	0.0402 (13)	−0.0123 (11)	0.0086 (10)	−0.0014 (11)
C10	0.0313 (12)	0.0297 (11)	0.0353 (11)	0.0024 (9)	0.0153 (9)	0.0035 (9)
C11	0.0370 (13)	0.0476 (14)	0.0365 (12)	0.0095 (11)	0.0137 (10)	0.0082 (10)
C12	0.0499 (16)	0.0596 (17)	0.0428 (14)	−0.0057 (13)	0.0161 (12)	−0.0057 (12)
C13	0.0549 (17)	0.0577 (17)	0.0448 (15)	−0.0044 (13)	0.0266 (13)	−0.0091 (12)
C14	0.0375 (14)	0.0428 (13)	0.0483 (14)	0.0030 (11)	0.0240 (11)	0.0039 (11)
S2	0.0264 (3)	0.0356 (3)	0.0497 (4)	0.0012 (2)	0.0113 (3)	0.0147 (3)
F2	0.0464 (9)	0.0605 (10)	0.0742 (11)	0.0162 (8)	0.0294 (8)	−0.0092 (8)
O4	0.0350 (9)	0.0342 (8)	0.0360 (8)	0.0045 (7)	0.0096 (7)	−0.0021 (7)
O5	0.0420 (10)	0.0311 (9)	0.0794 (13)	−0.0014 (8)	0.0065 (9)	0.0158 (9)
O6	0.0326 (10)	0.0718 (13)	0.0651 (12)	0.0029 (9)	0.0248 (9)	0.0214 (10)
C15	0.0278 (12)	0.0328 (11)	0.0347 (11)	0.0066 (9)	0.0120 (9)	0.0098 (9)
C16	0.0262 (11)	0.0308 (11)	0.0301 (11)	0.0035 (9)	0.0081 (9)	0.0080 (9)
C17	0.0300 (12)	0.0311 (11)	0.0375 (12)	0.0031 (9)	0.0099 (10)	0.0024 (9)
C18	0.0388 (14)	0.0397 (13)	0.0444 (14)	0.0123 (11)	0.0176 (11)	0.0041 (11)
C19	0.0253 (12)	0.0509 (15)	0.0521 (15)	0.0053 (11)	0.0129 (11)	0.0109 (12)
C20	0.0291 (12)	0.0377 (13)	0.0443 (13)	−0.0010 (10)	0.0059 (10)	0.0023 (10)
C21	0.0307 (12)	0.0299 (11)	0.0325 (11)	0.0059 (9)	0.0095 (9)	0.0034 (9)
C22	0.0327 (12)	0.0372 (12)	0.0340 (12)	0.0086 (10)	0.0139 (10)	0.0102 (9)
C23	0.0499 (16)	0.0497 (15)	0.0450 (14)	0.0195 (12)	0.0246 (12)	0.0076 (11)
C24	0.0318 (12)	0.0339 (12)	0.0417 (13)	−0.0020 (10)	0.0091 (10)	0.0031 (10)
C25	0.0480 (16)	0.0382 (14)	0.0609 (17)	−0.0087 (12)	0.0060 (13)	−0.0013 (12)
C26	0.0509 (18)	0.0546 (18)	0.069 (2)	0.0086 (14)	−0.0089 (15)	−0.0162 (15)
C27A	0.046 (3)	0.050 (3)	0.058 (4)	0.016 (3)	−0.013 (3)	−0.009 (3)
C27B	0.059 (6)	0.040 (4)	0.042 (4)	0.011 (4)	0.005 (4)	0.000 (3)
C28	0.0407 (15)	0.0318 (13)	0.0478 (15)	−0.0022 (11)	0.0034 (12)	0.0050 (11)

Geometric parameters (Å, º) top

S1—O3	1.4289 (17)	F2—C18	1.360 (3)
S1—O2	1.4329 (17)	O4—C22	1.362 (3)
S1—C1	1.735 (2)	O4—C21	1.379 (3)
S1—C10	1.774 (2)	C15—C22	1.358 (3)
F1—C4	1.359 (2)	C15—C16	1.442 (3)
O1—C8	1.355 (3)	C16—C21	1.380 (3)
O1—C7	1.377 (2)	C16—C17	1.390 (3)
C1—C8	1.356 (3)	C17—C18	1.372 (3)
C1—C2	1.444 (3)	C17—H17	0.9500
C2—C7	1.387 (3)	C18—C19	1.375 (3)
C2—C3	1.392 (3)	C19—C20	1.375 (3)
C3—C4	1.370 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.374 (3)
C4—C5	1.381 (3)	C20—H20	0.9500
C5—C6	1.379 (3)	C22—C23	1.471 (3)
C5—H5	0.9500	C23—H23A	0.9800
C6—C7	1.373 (3)	C23—H23B	0.9800
C6—H6	0.9500	C23—H23C	0.9800
C8—C9	1.478 (3)	C24—C28	1.523 (3)
C9—H9A	0.9800	C24—C25	1.529 (3)
C9—H9B	0.9800	C24—H24	1.0000
C9—H9C	0.9800	C25—C26	1.484 (4)
C10—C11	1.528 (3)	C25—H25A	0.9900
C10—C14	1.543 (3)	C25—H25B	0.9900
C10—H10	1.0000	C26—C27B	1.522 (2)
C11—C12	1.524 (3)	C26—C27A	1.522 (2)
C11—H11A	0.9900	C26—H26A	0.9900
C11—H11B	0.9900	C26—H26B	0.9900
C12—C13	1.492 (4)	C26—H26C	0.9900
C12—H12A	0.9900	C26—H26D	0.9900
C12—H12B	0.9900	C27A—C28	1.5166 (18)
C13—C14	1.520 (3)	C27A—H27A	0.9900
C13—H13A	0.9900	C27A—H27B	0.9900
C13—H13B	0.9900	C27B—C28	1.5171 (18)
C14—H14A	0.9900	C27B—H27C	0.9900
C14—H14B	0.9900	C27B—H27D	0.9900
S2—O6	1.4292 (19)	C28—H28A	0.9900
S2—O5	1.4294 (18)	C28—H28B	0.9900
S2—C15	1.733 (2)	C28—H28C	0.99 (7)
S2—C24	1.771 (2)	C28—H28D	0.87 (7)

O3—S1—O2	118.65 (11)	F2—C18—C19	117.8 (2)
O3—S1—C1	107.46 (10)	C17—C18—C19	124.8 (2)
O2—S1—C1	108.81 (10)	C20—C19—C18	119.4 (2)
O3—S1—C10	109.46 (10)	C20—C19—H19	120.3
O2—S1—C10	107.34 (10)	C18—C19—H19	120.3
C1—S1—C10	104.18 (10)	C21—C20—C19	116.5 (2)
C8—O1—C7	107.10 (15)	C21—C20—H20	121.7
C8—C1—C2	107.13 (19)	C19—C20—H20	121.7
C8—C1—S1	125.44 (16)	C20—C21—O4	125.7 (2)
C2—C1—S1	127.23 (16)	C20—C21—C16	124.1 (2)
C7—C2—C3	119.14 (19)	O4—C21—C16	110.18 (19)
C7—C2—C1	104.77 (17)	C15—C22—O4	110.5 (2)
C3—C2—C1	136.1 (2)	C15—C22—C23	134.7 (2)
C4—C3—C2	115.69 (19)	O4—C22—C23	114.8 (2)
C4—C3—H3	122.2	C22—C23—H23A	109.5
C2—C3—H3	122.2	C22—C23—H23B	109.5
F1—C4—C3	117.72 (19)	H23A—C23—H23B	109.5
F1—C4—C5	117.06 (19)	C22—C23—H23C	109.5
C3—C4—C5	125.22 (19)	H23A—C23—H23C	109.5
C6—C5—C4	119.1 (2)	H23B—C23—H23C	109.5
C6—C5—H5	120.5	C28—C24—C25	105.42 (19)
C4—C5—H5	120.5	C28—C24—S2	113.88 (17)
C7—C6—C5	116.5 (2)	C25—C24—S2	111.11 (17)
C7—C6—H6	121.8	C28—C24—H24	108.8
C5—C6—H6	121.8	C25—C24—H24	108.8
C6—C7—O1	125.45 (19)	S2—C24—H24	108.8
C6—C7—C2	124.39 (19)	C26—C25—C24	103.5 (2)
O1—C7—C2	110.14 (18)	C26—C25—H25A	111.1
O1—C8—C1	110.84 (17)	C24—C25—H25A	111.1
O1—C8—C9	115.52 (19)	C26—C25—H25B	111.1
C1—C8—C9	133.6 (2)	C24—C25—H25B	111.1
C8—C9—H9A	109.5	H25A—C25—H25B	109.0
C8—C9—H9B	109.5	C25—C26—C27B	110.6 (2)
H9A—C9—H9B	109.5	C25—C26—C27A	99.5 (5)
C8—C9—H9C	109.5	C25—C26—H26A	111.9
H9A—C9—H9C	109.5	C27B—C26—H26A	88.1
H9B—C9—H9C	109.5	C27A—C26—H26A	111.9
C11—C10—C14	106.14 (18)	C25—C26—H26B	111.9
C11—C10—S1	112.41 (15)	C27B—C26—H26B	122.4
C14—C10—S1	110.05 (16)	C27A—C26—H26B	111.9
C11—C10—H10	109.4	H26A—C26—H26B	109.6
C14—C10—H10	109.4	C25—C26—H26C	109.7
S1—C10—H10	109.4	C27B—C26—H26C	106.2
C12—C11—C10	104.7 (2)	C27A—C26—H26C	129.9
C12—C11—H11A	110.8	H26B—C26—H26C	94.1
C10—C11—H11A	110.8	C25—C26—H26D	110.0
C12—C11—H11B	110.8	C27B—C26—H26D	111.9
C10—C11—H11B	110.8	C27A—C26—H26D	98.1
H11A—C11—H11B	108.9	H26A—C26—H26D	122.4
C13—C12—C11	103.0 (2)	H26C—C26—H26D	108.3
C13—C12—H12A	111.2	C28—C27A—C26	104.3 (2)
C11—C12—H12A	111.2	C28—C27A—H27A	110.9
C13—C12—H12B	111.2	C26—C27A—H27A	110.9
C11—C12—H12B	111.2	C28—C27A—H27B	110.9
H12A—C12—H12B	109.1	C26—C27A—H27B	110.9
C12—C13—C14	104.7 (2)	H27A—C27A—H27B	108.9
C12—C13—H13A	110.8	C26—C27A—H28D	124 (3)
C14—C13—H13A	110.8	H27A—C27A—H28D	78.9
C12—C13—H13B	110.8	H27B—C27A—H28D	117.5
C14—C13—H13B	110.8	C28—C27B—C26	104.3 (2)
H13A—C13—H13B	108.9	C28—C27B—H27C	110.9
C13—C14—C10	104.66 (19)	C26—C27B—H27C	110.9
C13—C14—H14A	110.8	C28—C27B—H27D	110.9
C10—C14—H14A	110.8	C26—C27B—H27D	110.9
C13—C14—H14B	110.8	H27C—C27B—H27D	108.9
C10—C14—H14B	110.8	C27A—C28—C24	103.9 (3)
H14A—C14—H14B	108.9	C27B—C28—C24	107.6 (3)
O6—S2—O5	118.23 (11)	C27A—C28—H28A	111.0
O6—S2—C15	109.20 (11)	C27B—C28—H28A	88.1
O5—S2—C15	107.56 (10)	C24—C28—H28A	111.0
O6—S2—C24	109.04 (11)	C27A—C28—H28B	111.0
O5—S2—C24	107.64 (11)	C27B—C28—H28B	127.7
C15—S2—C24	104.28 (10)	C24—C28—H28B	111.0
C22—O4—C21	107.03 (16)	H28A—C28—H28B	109.0
C22—C15—C16	107.17 (19)	C27A—C28—H28C	137 (4)
C22—C15—S2	127.18 (18)	C27B—C28—H28C	123 (4)
C16—C15—S2	125.52 (17)	C24—C28—H28C	118 (4)
C21—C16—C17	119.4 (2)	H28A—C28—H28C	45.4
C21—C16—C15	105.14 (19)	H28B—C28—H28C	64.8
C17—C16—C15	135.4 (2)	C27A—C28—H28D	76 (4)
C18—C17—C16	115.7 (2)	C27B—C28—H28D	98 (5)
C18—C17—H17	122.2	C24—C28—H28D	107 (5)
C16—C17—H17	122.2	H28A—C28—H28D	137.9
F2—C18—C17	117.4 (2)	H28C—C28—H28D	100 (6)

O3—S1—C1—C8	−165.58 (19)	C24—S2—C15—C16	76.3 (2)
O2—S1—C1—C8	−35.9 (2)	C22—C15—C16—C21	0.1 (2)
C10—S1—C1—C8	78.3 (2)	S2—C15—C16—C21	−176.02 (16)
O3—S1—C1—C2	20.1 (2)	C22—C15—C16—C17	−180.0 (2)
O2—S1—C1—C2	149.75 (18)	S2—C15—C16—C17	3.9 (4)
C10—S1—C1—C2	−96.00 (19)	C21—C16—C17—C18	1.7 (3)
C8—C1—C2—C7	0.0 (2)	C15—C16—C17—C18	−178.2 (2)
S1—C1—C2—C7	175.20 (16)	C16—C17—C18—F2	−179.82 (19)
C8—C1—C2—C3	179.9 (2)	C16—C17—C18—C19	−0.8 (4)
S1—C1—C2—C3	−4.9 (4)	F2—C18—C19—C20	178.6 (2)
C7—C2—C3—C4	−1.0 (3)	C17—C18—C19—C20	−0.5 (4)
C1—C2—C3—C4	179.1 (2)	C18—C19—C20—C21	0.7 (3)
C2—C3—C4—F1	179.56 (18)	C19—C20—C21—O4	179.4 (2)
C2—C3—C4—C5	−0.2 (3)	C19—C20—C21—C16	0.3 (3)
F1—C4—C5—C6	−178.90 (19)	C22—O4—C21—C20	−177.9 (2)
C3—C4—C5—C6	0.9 (4)	C22—O4—C21—C16	1.3 (2)
C4—C5—C6—C7	−0.2 (3)	C17—C16—C21—C20	−1.6 (3)
C5—C6—C7—O1	−179.5 (2)	C15—C16—C21—C20	178.4 (2)
C5—C6—C7—C2	−1.1 (3)	C17—C16—C21—O4	179.21 (18)
C8—O1—C7—C6	178.1 (2)	C15—C16—C21—O4	−0.8 (2)
C8—O1—C7—C2	−0.5 (2)	C16—C15—C22—O4	0.7 (2)
C3—C2—C7—C6	1.8 (3)	S2—C15—C22—O4	176.73 (15)
C1—C2—C7—C6	−178.4 (2)	C16—C15—C22—C23	−178.4 (2)
C3—C2—C7—O1	−179.60 (17)	S2—C15—C22—C23	−2.4 (4)
C1—C2—C7—O1	0.3 (2)	C21—O4—C22—C15	−1.2 (2)
C7—O1—C8—C1	0.5 (2)	C21—O4—C22—C23	178.08 (18)
C7—O1—C8—C9	−177.92 (18)	O6—S2—C24—C28	−47.9 (2)
C2—C1—C8—O1	−0.3 (2)	O5—S2—C24—C28	−177.32 (17)
S1—C1—C8—O1	−175.62 (14)	C15—S2—C24—C28	68.63 (19)
C2—C1—C8—C9	177.7 (2)	O6—S2—C24—C25	70.9 (2)
S1—C1—C8—C9	2.4 (4)	O5—S2—C24—C25	−58.5 (2)
O3—S1—C10—C11	−50.09 (18)	C15—S2—C24—C25	−172.52 (18)
O2—S1—C10—C11	179.88 (16)	C28—C24—C25—C26	−29.6 (3)
C1—S1—C10—C11	64.59 (18)	S2—C24—C25—C26	−153.4 (2)
O3—S1—C10—C14	67.98 (17)	C24—C25—C26—C27B	23.9 (8)
O2—S1—C10—C14	−62.05 (17)	C24—C25—C26—C27A	45.8 (5)
C1—S1—C10—C14	−177.34 (15)	C25—C26—C27A—C28	−46.0 (9)
C14—C10—C11—C12	−17.1 (2)	C27B—C26—C27A—C28	74.3 (4)
S1—C10—C11—C12	103.3 (2)	C25—C26—C27B—C28	−8.7 (12)
C10—C11—C12—C13	36.0 (3)	C27A—C26—C27B—C28	−74.2 (4)
C11—C12—C13—C14	−41.4 (3)	C26—C27A—C28—C27B	−74.3 (4)
C12—C13—C14—C10	30.6 (3)	C26—C27A—C28—C24	27.8 (10)
C11—C10—C14—C13	−7.9 (2)	C26—C27B—C28—C27A	74.2 (4)
S1—C10—C14—C13	−129.75 (18)	C26—C27B—C28—C24	−10.5 (12)
O6—S2—C15—C22	17.4 (2)	C25—C24—C28—C27A	0.6 (7)
O5—S2—C15—C22	146.8 (2)	S2—C24—C28—C27A	122.7 (6)
C24—S2—C15—C22	−99.1 (2)	C25—C24—C28—C27B	25.2 (8)
O6—S2—C15—C16	−167.32 (18)	S2—C24—C28—C27B	147.2 (8)
O5—S2—C15—C16	−37.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O6ⁱ	0.98	2.45	3.348 (3)	152
C19—H19···O6ⁱⁱ	0.95	2.58	3.469 (3)	157
C23—H23A···O2ⁱⁱⁱ	0.98	2.50	3.318 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅FO₃S
M_r	282.32
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	10.0568 (8), 10.2697 (8), 13.2894 (10)
α, β, γ (°)	95.033 (4), 109.140 (4), 91.229 (4)
V (Å³)	1289.82 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.936, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	21777, 5565, 4022
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.119, 1.03
No. of reflections	5565
No. of parameters	361
No. of restraints	20
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.31

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
C9—H9C···O6ⁱ	0.98	2.45	3.348 (3)	152
C19—H19···O6ⁱⁱ	0.95	2.58	3.469 (3)	157
C23—H23A···O2ⁱⁱⁱ	0.98	2.50	3.318 (3)	141

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

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
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
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1386. 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
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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1689

doi:10.1107/S1600536811021222

Open

access