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

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COMMUNICATIONS
ISSN: 2056-9890

5-Cyclo­hexyl-3-(2-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzo­furan

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 April 2013; accepted 1 May 2013; online 15 May 2013)

In the title compound, C21H21FO2S, the cyclo­hexyl ring adopts a chair conformation. The 2-fluoro­phenyl ring makes a dihedral angle of 88.47 (4)° with the mean plane [r.m.s. deviation = 0.013 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions, forming chains propagating along [100]. The crystal structure also exhibits slipped ππ inter­actions between the furan rings of neighboring mol­ecules [centroid-to-centroid distance = 3.397 (2) Å, inter­planar distance = 3.346 (2) Å and slippage = 0.586 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o768.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o205.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21FO2S

  • Mr = 356.44

  • Triclinic, [P \overline 1]

  • a = 9.0667 (2) Å

  • b = 10.3647 (2) Å

  • c = 10.6838 (2) Å

  • α = 105.395 (1)°

  • β = 93.418 (1)°

  • γ = 110.839 (1)°

  • V = 891.33 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 173 K

  • 0.30 × 0.22 × 0.21 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.681, Tmax = 0.746

  • 16785 measured reflections

  • 4455 independent reflections

  • 3495 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.04

  • 4455 reflections

  • 227 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O2i 0.95 2.60 3.5024 (19) 160
C20—H20⋯O1ii 0.95 2.53 3.316 (2) 140
C21—H21⋯O2i 0.95 2.49 3.332 (2) 148
C14—H14BCg2iii 0.99 2.69 3.618 (2) 156
C15—H15BCg2iv 0.98 2.85 3.422 (2) 118
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our continuing study of 5-cyclohexyl-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (Choi et al., 2011) and 4-bromophenylsulfinyl (Choi et al., 2012) substituents in 3-position, 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 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring has the chair form. The dihedral angle formed by the 2-fluorophenyl ring and the mean plane of the benzofuran fragment is 88.47 (4)°. In the crystal structure (Figs. 2 and 3), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg2 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 3) also exhibits slipped ππ interactions between the furan rings of neighbouring molecules, with a Cg1···Cg1iv distance of 3.397 (2) Å and an interplanar distance of 3.346 (2) Å resulting in a slippage of 0.586 (2) Å (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(2-fluorophenylsulfanyl)-2-methyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (40 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 424-425 K; Rf = 0.46 (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 acetone at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine and methylene, and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

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, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. A view of the C—H···O 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 + 1, -y + 2, -z + 1; (ii) x - 1, y, z; (v) x + 1, y, z.]
[Figure 3] Fig. 3. A view of the C—H···π and ππ interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (iii) -x + 1, -y + 1, -z + 1; (iv) -x + 2, -y + 2, -z + 1.]
5-Cyclohexyl-3-(2-fluorophenylsulfinyl)-2-methyl-1-benzofuran top
Crystal data top
C21H21FO2SZ = 2
Mr = 356.44F(000) = 376
Triclinic, P1Dx = 1.328 Mg m3
Hall symbol: -P 1Melting point = 424–425 K
a = 9.0667 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3647 (2) ÅCell parameters from 5827 reflections
c = 10.6838 (2) Åθ = 2.5–28.3°
α = 105.395 (1)°µ = 0.20 mm1
β = 93.418 (1)°T = 173 K
γ = 110.839 (1)°Block, colourless
V = 891.33 (3) Å30.30 × 0.22 × 0.21 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4455 independent reflections
Radiation source: rotating anode3495 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.031
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.0°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.681, Tmax = 0.746l = 1414
16785 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.116H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.2597P]
where P = (Fo2 + 2Fc2)/3
4455 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C21H21FO2Sγ = 110.839 (1)°
Mr = 356.44V = 891.33 (3) Å3
Triclinic, P1Z = 2
a = 9.0667 (2) ÅMo Kα radiation
b = 10.3647 (2) ŵ = 0.20 mm1
c = 10.6838 (2) ÅT = 173 K
α = 105.395 (1)°0.30 × 0.22 × 0.21 mm
β = 93.418 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
4455 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3495 reflections with I > 2σ(I)
Tmin = 0.681, Tmax = 0.746Rint = 0.031
16785 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.04Δρmax = 0.35 e Å3
4455 reflectionsΔρmin = 0.30 e Å3
227 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
xyzUiso*/Ueq
S10.76058 (5)1.09181 (4)0.70859 (4)0.03217 (12)
O11.03485 (12)0.87847 (12)0.60101 (10)0.0301 (2)
O20.67934 (15)1.12362 (13)0.60291 (12)0.0422 (3)
F10.79828 (12)0.97950 (14)0.92911 (10)0.0507 (3)
C10.84436 (18)0.96774 (16)0.63603 (14)0.0264 (3)
C20.77490 (17)0.83447 (15)0.52735 (14)0.0251 (3)
C30.62620 (18)0.75355 (16)0.44660 (15)0.0278 (3)
H30.54060.78600.45600.033*
C40.60561 (19)0.62411 (16)0.35184 (16)0.0306 (3)
C50.7353 (2)0.58063 (18)0.33814 (17)0.0364 (4)
H50.71980.49250.27260.044*
C60.8845 (2)0.66036 (18)0.41581 (17)0.0351 (4)
H60.97170.63040.40450.042*
C70.89918 (18)0.78535 (16)0.51019 (15)0.0273 (3)
C80.99753 (18)0.98799 (16)0.67553 (15)0.0282 (3)
C90.4458 (2)0.52941 (17)0.26325 (17)0.0362 (4)
H90.45100.43340.21930.043*
C100.4120 (2)0.5904 (2)0.15474 (17)0.0394 (4)
H10A0.40590.68580.19490.047*
H10B0.50120.60550.10390.047*
C110.2557 (2)0.4885 (2)0.06208 (19)0.0517 (5)
H11A0.23430.53360.00410.062*
H11B0.26620.39700.01470.062*
C120.1165 (2)0.4548 (2)0.1352 (2)0.0489 (5)
H12A0.09590.54390.17170.059*
H12B0.01940.38160.07300.059*
C130.1483 (2)0.3982 (2)0.2457 (2)0.0567 (6)
H13A0.15320.30190.20830.068*
H13B0.05900.38600.29630.068*
C140.3054 (2)0.5009 (2)0.3382 (2)0.0516 (5)
H14A0.29640.59400.38290.062*
H14B0.32540.45800.40670.062*
C151.1253 (2)1.09951 (19)0.78339 (17)0.0372 (4)
H15A1.09491.18210.81900.056*
H15B1.22561.13230.74930.056*
H15C1.14011.05810.85330.056*
C160.60472 (19)0.97077 (17)0.76771 (15)0.0303 (3)
C170.6418 (2)0.93040 (19)0.87463 (16)0.0347 (4)
C180.5274 (2)0.8447 (2)0.92798 (18)0.0406 (4)
H180.55600.81801.00140.049*
C190.3692 (2)0.79842 (19)0.87168 (19)0.0416 (4)
H190.28720.73980.90740.050*
C200.3288 (2)0.83647 (19)0.76392 (19)0.0427 (4)
H200.21940.80250.72540.051*
C210.4458 (2)0.92345 (18)0.71169 (17)0.0364 (4)
H210.41750.95040.63830.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0368 (2)0.0274 (2)0.0298 (2)0.01355 (17)0.00040 (16)0.00423 (16)
O10.0240 (5)0.0359 (6)0.0295 (6)0.0102 (5)0.0022 (4)0.0111 (5)
O20.0506 (7)0.0417 (7)0.0430 (7)0.0253 (6)0.0040 (6)0.0176 (6)
F10.0376 (6)0.0818 (8)0.0353 (6)0.0238 (6)0.0011 (5)0.0229 (6)
C10.0276 (7)0.0260 (7)0.0232 (7)0.0083 (6)0.0021 (6)0.0069 (6)
C20.0277 (7)0.0251 (7)0.0236 (7)0.0093 (6)0.0038 (6)0.0103 (6)
C30.0269 (7)0.0264 (7)0.0289 (8)0.0086 (6)0.0019 (6)0.0095 (6)
C40.0321 (8)0.0245 (7)0.0309 (8)0.0073 (6)0.0003 (6)0.0079 (6)
C50.0426 (10)0.0276 (8)0.0342 (9)0.0141 (7)0.0030 (7)0.0019 (7)
C60.0348 (9)0.0368 (9)0.0368 (9)0.0183 (7)0.0077 (7)0.0099 (7)
C70.0255 (7)0.0300 (7)0.0257 (7)0.0084 (6)0.0027 (6)0.0113 (6)
C80.0293 (8)0.0299 (8)0.0250 (8)0.0085 (6)0.0033 (6)0.0121 (6)
C90.0364 (9)0.0224 (7)0.0396 (9)0.0068 (7)0.0048 (7)0.0019 (7)
C100.0337 (9)0.0483 (10)0.0296 (9)0.0080 (8)0.0040 (7)0.0126 (8)
C110.0410 (11)0.0669 (13)0.0342 (10)0.0092 (10)0.0038 (8)0.0129 (9)
C120.0332 (9)0.0543 (12)0.0502 (11)0.0084 (9)0.0025 (8)0.0155 (9)
C130.0379 (10)0.0543 (12)0.0627 (13)0.0061 (9)0.0035 (9)0.0294 (11)
C140.0390 (10)0.0554 (12)0.0464 (11)0.0057 (9)0.0023 (8)0.0284 (10)
C150.0306 (8)0.0394 (9)0.0329 (9)0.0057 (7)0.0051 (7)0.0105 (7)
C160.0345 (8)0.0312 (8)0.0251 (8)0.0169 (7)0.0036 (6)0.0032 (6)
C170.0350 (9)0.0408 (9)0.0278 (8)0.0187 (7)0.0014 (7)0.0050 (7)
C180.0502 (11)0.0438 (10)0.0353 (9)0.0257 (9)0.0104 (8)0.0128 (8)
C190.0426 (10)0.0317 (9)0.0494 (11)0.0152 (8)0.0149 (8)0.0083 (8)
C200.0329 (9)0.0373 (9)0.0525 (11)0.0149 (8)0.0001 (8)0.0048 (8)
C210.0369 (9)0.0364 (9)0.0349 (9)0.0186 (7)0.0021 (7)0.0053 (7)
Geometric parameters (Å, º) top
S1—O21.4823 (12)C11—C121.508 (3)
S1—C11.7516 (15)C11—H11A0.9900
S1—C161.7988 (17)C11—H11B0.9900
O1—C81.3647 (19)C12—C131.506 (3)
O1—C71.3790 (18)C12—H12A0.9900
F1—C171.3569 (19)C12—H12B0.9900
C1—C81.351 (2)C13—C141.527 (3)
C1—C21.447 (2)C13—H13A0.9900
C2—C31.392 (2)C13—H13B0.9900
C2—C71.395 (2)C14—H14A0.9900
C3—C41.392 (2)C14—H14B0.9900
C3—H30.9500C15—H15A0.9800
C4—C51.403 (2)C15—H15B0.9800
C4—C91.513 (2)C15—H15C0.9800
C5—C61.381 (2)C16—C171.379 (2)
C5—H50.9500C16—C211.383 (2)
C6—C71.371 (2)C17—C181.368 (3)
C6—H60.9500C18—C191.380 (3)
C8—C151.479 (2)C18—H180.9500
C9—C101.524 (2)C19—C201.382 (3)
C9—C141.527 (3)C19—H190.9500
C9—H91.0000C20—C211.381 (3)
C10—C111.522 (2)C20—H200.9500
C10—H10A0.9900C21—H210.9500
C10—H10B0.9900
O2—S1—C1108.76 (7)C10—C11—H11B109.3
O2—S1—C16106.28 (8)H11A—C11—H11B107.9
C1—S1—C1697.18 (7)C13—C12—C11111.76 (17)
C8—O1—C7106.55 (11)C13—C12—H12A109.3
C8—C1—C2107.67 (13)C11—C12—H12A109.3
C8—C1—S1122.41 (12)C13—C12—H12B109.3
C2—C1—S1129.89 (11)C11—C12—H12B109.3
C3—C2—C7119.50 (14)H12A—C12—H12B107.9
C3—C2—C1136.36 (14)C12—C13—C14111.52 (15)
C7—C2—C1104.13 (13)C12—C13—H13A109.3
C2—C3—C4118.59 (14)C14—C13—H13A109.3
C2—C3—H3120.7C12—C13—H13B109.3
C4—C3—H3120.7C14—C13—H13B109.3
C3—C4—C5119.45 (15)H13A—C13—H13B108.0
C3—C4—C9121.17 (14)C9—C14—C13111.25 (17)
C5—C4—C9119.38 (14)C9—C14—H14A109.4
C6—C5—C4122.89 (15)C13—C14—H14A109.4
C6—C5—H5118.6C9—C14—H14B109.4
C4—C5—H5118.6C13—C14—H14B109.4
C7—C6—C5116.01 (15)H14A—C14—H14B108.0
C7—C6—H6122.0C8—C15—H15A109.5
C5—C6—H6122.0C8—C15—H15B109.5
C6—C7—O1125.80 (14)H15A—C15—H15B109.5
C6—C7—C2123.52 (15)C8—C15—H15C109.5
O1—C7—C2110.68 (13)H15A—C15—H15C109.5
C1—C8—O1110.97 (13)H15B—C15—H15C109.5
C1—C8—C15132.96 (15)C17—C16—C21119.06 (16)
O1—C8—C15116.03 (13)C17—C16—S1120.14 (13)
C4—C9—C10112.40 (13)C21—C16—S1120.71 (13)
C4—C9—C14113.24 (14)F1—C17—C18119.26 (15)
C10—C9—C14109.31 (14)F1—C17—C16118.10 (15)
C4—C9—H9107.2C18—C17—C16122.63 (16)
C10—C9—H9107.2C17—C18—C19117.89 (17)
C14—C9—H9107.2C17—C18—H18121.1
C11—C10—C9111.29 (15)C19—C18—H18121.1
C11—C10—H10A109.4C18—C19—C20120.65 (17)
C9—C10—H10A109.4C18—C19—H19119.7
C11—C10—H10B109.4C20—C19—H19119.7
C9—C10—H10B109.4C21—C20—C19120.64 (17)
H10A—C10—H10B108.0C21—C20—H20119.7
C12—C11—C10111.80 (16)C19—C20—H20119.7
C12—C11—H11A109.3C20—C21—C16119.12 (16)
C10—C11—H11A109.3C20—C21—H21120.4
C12—C11—H11B109.3C16—C21—H21120.4
O2—S1—C1—C8131.20 (13)C7—O1—C8—C15178.13 (12)
C16—S1—C1—C8118.85 (14)C3—C4—C9—C1075.69 (19)
O2—S1—C1—C246.74 (16)C5—C4—C9—C10104.29 (18)
C16—S1—C1—C263.21 (15)C3—C4—C9—C1448.8 (2)
C8—C1—C2—C3178.69 (16)C5—C4—C9—C14131.23 (17)
S1—C1—C2—C33.1 (3)C4—C9—C10—C11176.45 (15)
C8—C1—C2—C70.48 (16)C14—C9—C10—C1156.9 (2)
S1—C1—C2—C7177.70 (12)C9—C10—C11—C1255.9 (2)
C7—C2—C3—C40.9 (2)C10—C11—C12—C1353.9 (2)
C1—C2—C3—C4178.16 (16)C11—C12—C13—C1453.8 (3)
C2—C3—C4—C51.5 (2)C4—C9—C14—C13176.82 (15)
C2—C3—C4—C9178.51 (14)C10—C9—C14—C1357.0 (2)
C3—C4—C5—C60.5 (3)C12—C13—C14—C956.0 (2)
C9—C4—C5—C6179.48 (15)O2—S1—C16—C17174.67 (12)
C4—C5—C6—C71.0 (2)C1—S1—C16—C1773.34 (14)
C5—C6—C7—O1177.69 (14)O2—S1—C16—C211.70 (15)
C5—C6—C7—C21.7 (2)C1—S1—C16—C21110.29 (14)
C8—O1—C7—C6179.97 (15)C21—C16—C17—F1179.18 (14)
C8—O1—C7—C20.55 (15)S1—C16—C17—F12.8 (2)
C3—C2—C7—C60.7 (2)C21—C16—C17—C180.1 (2)
C1—C2—C7—C6179.93 (14)S1—C16—C17—C18176.54 (13)
C3—C2—C7—O1178.71 (12)F1—C17—C18—C19178.98 (15)
C1—C2—C7—O10.63 (16)C16—C17—C18—C190.3 (3)
C2—C1—C8—O10.17 (17)C17—C18—C19—C200.7 (3)
S1—C1—C8—O1178.18 (10)C18—C19—C20—C211.0 (3)
C2—C1—C8—C15177.26 (15)C19—C20—C21—C160.8 (3)
S1—C1—C8—C154.4 (2)C17—C16—C21—C200.3 (2)
C7—O1—C8—C10.23 (16)S1—C16—C21—C20176.75 (12)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.603.5024 (19)160
C20—H20···O1ii0.952.533.316 (2)140
C21—H21···O2i0.952.493.332 (2)148
C14—H14B···Cg2iii0.992.693.618 (2)156
C15—H15B···Cg2iv0.982.853.422 (2)118
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+2, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC21H21FO2S
Mr356.44
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.0667 (2), 10.3647 (2), 10.6838 (2)
α, β, γ (°)105.395 (1), 93.418 (1), 110.839 (1)
V3)891.33 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.30 × 0.22 × 0.21
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.681, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
16785, 4455, 3495
Rint0.031
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.04
No. of reflections4455
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.603.5024 (19)159.5
C20—H20···O1ii0.952.533.316 (2)139.8
C21—H21···O2i0.952.493.332 (2)147.7
C14—H14B···Cg2iii0.992.693.618 (2)156.0
C15—H15B···Cg2iv0.982.853.422 (2)118.2
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+2, y+2, z+1.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (grant No. RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o205.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o768.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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