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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Cyclo­pentyl-2-(4-fluoro­phen­yl)-3-iso­propyl­sulfonyl-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 22 October 2012; accepted 7 November 2012; online 10 November 2012)

In the title compound, C22H23FO3S, the cyclo­pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The 4-fluoro­phenyl ring makes a dihedral angle of 43.67 (3)° 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⋯O and C—H⋯π inter­actions, forming a three--dimensional network. The crystal structure also exhibits slipped ππ inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.883 (2) Å and slippage = 1.731 (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, o1000.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2591.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23FO3S

  • Mr = 386.46

  • Monoclinic, P 21 /n

  • a = 9.4736 (3) Å

  • b = 19.6185 (7) Å

  • c = 10.8018 (3) Å

  • β = 108.833 (1)°

  • V = 1900.12 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 173 K

  • 0.40 × 0.39 × 0.36 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 = 0.678, Tmax = 0.746

  • 18610 measured reflections

  • 4714 independent reflections

  • 3948 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.103

  • S = 1.03

  • 4714 reflections

  • 246 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −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 DA D—H⋯A
C6—H6⋯O2i 0.95 2.60 3.3341 (17) 135
C18—H18⋯O3ii 0.95 2.48 3.2932 (19) 144
C21—H21ACg1iii 0.98 2.71 3.693 (2) 177
Symmetry codes: (i) x-1, y, z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z.

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 ongoing study of 5-cyclopentyl-1-benzofuran derivatives containing (2-phenyl-3-methylsulfinyl) (Choi et al., 2011) and {2-(4-fluorophenyl)-3-methylsulfinyl} (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 cyclopentyl ring has an envelope conformation. The dihedral angle between the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 43.67 (3)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 2) also exhibits slipped ππ interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2iv distance of 3.883 (2) Å and an interplanar distance of 3.476 (2) Å resulting in a slippage of 1.731 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring, iv: -x + 1, -y + 1, -z + 1).

Related literature top

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

Experimental top

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-(4-fluorophenyl)-3-isopropylsulfanyl-1-benzofuran (283 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 67%, m.p. 397–398 K; Rf = 0.62 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Refinement top

All H atoms were geometrically positioned 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, 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, 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: (i) x -1, y, z; (ii) - x + 1.5, y - 0.5, - z + 0.5; (iii) - x + 1, - y + 1, - z; (iv) - x + 1, - y + 1, - z + 1; (v) x + 1, y, z; (vi) - x + 1/2, y + 1/2, - z + 1/2.]
5-Cyclopentyl-2-(4-fluorophenyl)-3-isopropylsulfonyl-1-benzofuran top
Crystal data top
C22H23FO3SF(000) = 816
Mr = 386.46Dx = 1.351 Mg m3
Monoclinic, P21/nMelting point = 397–398 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.4736 (3) ÅCell parameters from 5864 reflections
b = 19.6185 (7) Åθ = 2.3–28.0°
c = 10.8018 (3) ŵ = 0.20 mm1
β = 108.833 (1)°T = 173 K
V = 1900.12 (10) Å3Block, colourless
Z = 40.40 × 0.39 × 0.36 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4714 independent reflections
Radiation source: rotating anode3948 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.1°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 2226
Tmin = 0.678, Tmax = 0.746l = 1414
18610 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)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.103H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6277P]
where P = (Fo2 + 2Fc2)/3
4714 reflections(Δ/σ)max = 0.001
246 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C22H23FO3SV = 1900.12 (10) Å3
Mr = 386.46Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.4736 (3) ŵ = 0.20 mm1
b = 19.6185 (7) ÅT = 173 K
c = 10.8018 (3) Å0.40 × 0.39 × 0.36 mm
β = 108.833 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
4714 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3948 reflections with I > 2σ(I)
Tmin = 0.678, Tmax = 0.746Rint = 0.030
18610 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.03Δρmax = 0.40 e Å3
4714 reflectionsΔρmin = 0.35 e Å3
246 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.81280 (3)0.528906 (17)0.27421 (3)0.02105 (10)
F10.90366 (12)0.18165 (5)0.46703 (11)0.0459 (3)
O10.48867 (10)0.43110 (5)0.35291 (10)0.0264 (2)
O20.93832 (11)0.48394 (5)0.32355 (11)0.0299 (2)
O30.83351 (11)0.60006 (5)0.30821 (10)0.0297 (2)
C10.66190 (14)0.50030 (7)0.31937 (13)0.0215 (3)
C20.53071 (14)0.54131 (7)0.30820 (13)0.0217 (3)
C30.49027 (15)0.60966 (7)0.28294 (13)0.0235 (3)
H30.55890.64190.26970.028*
C40.34694 (15)0.62964 (7)0.27761 (13)0.0251 (3)
C50.24785 (15)0.58109 (8)0.29843 (14)0.0275 (3)
H50.15060.59550.29390.033*
C60.28562 (15)0.51320 (8)0.32526 (14)0.0280 (3)
H60.21800.48090.33990.034*
C70.42847 (15)0.49561 (7)0.32929 (14)0.0238 (3)
C80.63093 (14)0.43500 (7)0.34624 (13)0.0229 (3)
C90.29291 (16)0.70217 (8)0.24587 (15)0.0292 (3)
H90.20070.70760.27090.035*
C100.2528 (2)0.72112 (9)0.10096 (16)0.0411 (4)
H10A0.33310.70740.06600.049*
H10B0.15870.69880.04870.049*
C110.2353 (2)0.79875 (9)0.09816 (17)0.0416 (4)
H11A0.12950.81150.08070.050*
H11B0.27060.81900.02950.050*
C120.3312 (2)0.82331 (9)0.2342 (2)0.0471 (5)
H12A0.41070.85430.22710.057*
H12B0.26920.84790.27780.057*
C130.3992 (2)0.75922 (9)0.31167 (18)0.0424 (4)
H13A0.50030.75060.30700.051*
H13B0.40560.76390.40460.051*
C140.70929 (15)0.36969 (7)0.37007 (14)0.0241 (3)
C150.85560 (16)0.36436 (7)0.45435 (14)0.0256 (3)
H150.91030.40440.48960.031*
C160.92156 (16)0.30085 (8)0.48691 (15)0.0298 (3)
H161.02040.29660.54560.036*
C170.83981 (18)0.24418 (8)0.43187 (16)0.0323 (3)
C180.69763 (19)0.24717 (8)0.34516 (16)0.0347 (3)
H180.64610.20690.30690.042*
C190.63156 (17)0.31065 (8)0.31509 (15)0.0306 (3)
H190.53250.31410.25660.037*
C200.74619 (16)0.52264 (8)0.09910 (14)0.0292 (3)
H200.64930.54770.06550.035*
C210.7201 (2)0.44906 (10)0.05634 (18)0.0481 (5)
H21A0.68780.44660.03940.072*
H21B0.64260.42960.08780.072*
H21C0.81280.42330.09290.072*
C220.8593 (2)0.55731 (9)0.04609 (17)0.0410 (4)
H22A0.95600.53440.08100.061*
H22B0.86980.60530.07290.061*
H22C0.82460.55450.04960.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01823 (16)0.01971 (18)0.02505 (17)0.00166 (12)0.00676 (12)0.00080 (12)
F10.0517 (6)0.0212 (5)0.0596 (7)0.0103 (4)0.0106 (5)0.0027 (4)
O10.0223 (5)0.0215 (5)0.0367 (6)0.0023 (4)0.0113 (4)0.0004 (4)
O20.0193 (5)0.0320 (6)0.0380 (6)0.0034 (4)0.0090 (4)0.0067 (5)
O30.0314 (5)0.0216 (5)0.0373 (6)0.0074 (4)0.0124 (4)0.0046 (4)
C10.0190 (6)0.0198 (6)0.0253 (6)0.0007 (5)0.0065 (5)0.0015 (5)
C20.0196 (6)0.0228 (7)0.0225 (6)0.0011 (5)0.0063 (5)0.0020 (5)
C30.0231 (6)0.0216 (7)0.0260 (7)0.0002 (5)0.0082 (5)0.0008 (5)
C40.0245 (6)0.0257 (7)0.0244 (7)0.0026 (5)0.0066 (5)0.0035 (5)
C50.0199 (6)0.0332 (8)0.0298 (7)0.0020 (6)0.0087 (5)0.0046 (6)
C60.0223 (7)0.0302 (8)0.0329 (7)0.0040 (6)0.0110 (6)0.0028 (6)
C70.0235 (6)0.0204 (7)0.0270 (7)0.0007 (5)0.0077 (5)0.0010 (5)
C80.0202 (6)0.0228 (7)0.0256 (7)0.0025 (5)0.0071 (5)0.0029 (5)
C90.0256 (7)0.0268 (8)0.0355 (8)0.0056 (6)0.0103 (6)0.0023 (6)
C100.0478 (10)0.0339 (9)0.0335 (9)0.0123 (8)0.0018 (7)0.0007 (7)
C110.0459 (10)0.0343 (10)0.0449 (10)0.0155 (8)0.0150 (8)0.0075 (7)
C120.0444 (10)0.0260 (9)0.0634 (12)0.0050 (7)0.0070 (9)0.0025 (8)
C130.0415 (9)0.0304 (9)0.0444 (10)0.0063 (7)0.0014 (7)0.0084 (7)
C140.0269 (7)0.0188 (7)0.0272 (7)0.0003 (5)0.0098 (5)0.0003 (5)
C150.0266 (7)0.0218 (7)0.0287 (7)0.0017 (5)0.0092 (6)0.0014 (6)
C160.0287 (7)0.0277 (8)0.0321 (8)0.0025 (6)0.0083 (6)0.0012 (6)
C170.0413 (8)0.0188 (7)0.0381 (8)0.0067 (6)0.0148 (7)0.0020 (6)
C180.0412 (9)0.0200 (8)0.0394 (9)0.0042 (6)0.0082 (7)0.0051 (6)
C190.0298 (7)0.0233 (7)0.0346 (8)0.0019 (6)0.0047 (6)0.0026 (6)
C200.0290 (7)0.0333 (8)0.0239 (7)0.0019 (6)0.0065 (6)0.0006 (6)
C210.0667 (12)0.0422 (11)0.0345 (9)0.0129 (9)0.0150 (8)0.0137 (8)
C220.0479 (10)0.0459 (10)0.0356 (9)0.0007 (8)0.0225 (7)0.0012 (7)
Geometric parameters (Å, º) top
S1—O21.4377 (10)C11—H11A0.9900
S1—O31.4406 (11)C11—H11B0.9900
S1—C11.7455 (13)C12—C131.533 (2)
S1—C201.7946 (14)C12—H12A0.9900
F1—C171.3663 (17)C12—H12B0.9900
O1—C81.3749 (15)C13—H13A0.9900
O1—C71.3776 (17)C13—H13B0.9900
C1—C81.3661 (19)C14—C151.395 (2)
C1—C21.4526 (18)C14—C191.398 (2)
C2—C71.3916 (18)C15—C161.387 (2)
C2—C31.3971 (19)C15—H150.9500
C3—C41.3965 (18)C16—C171.375 (2)
C3—H30.9500C16—H160.9500
C4—C51.405 (2)C17—C181.371 (2)
C4—C91.514 (2)C18—C191.385 (2)
C5—C61.385 (2)C18—H180.9500
C5—H50.9500C19—H190.9500
C6—C71.3836 (18)C20—C211.511 (2)
C6—H60.9500C20—C221.528 (2)
C8—C141.4613 (19)C20—H201.0000
C9—C131.520 (2)C21—H21A0.9800
C9—C101.533 (2)C21—H21B0.9800
C9—H91.0000C21—H21C0.9800
C10—C111.531 (2)C22—H22A0.9800
C10—H10A0.9900C22—H22B0.9800
C10—H10B0.9900C22—H22C0.9800
C11—C121.534 (3)
O2—S1—O3118.15 (6)C13—C12—C11106.26 (14)
O2—S1—C1110.68 (6)C13—C12—H12A110.5
O3—S1—C1107.26 (6)C11—C12—H12A110.5
O2—S1—C20108.42 (7)C13—C12—H12B110.5
O3—S1—C20107.92 (7)C11—C12—H12B110.5
C1—S1—C20103.38 (7)H12A—C12—H12B108.7
C8—O1—C7107.06 (10)C9—C13—C12104.50 (13)
C8—C1—C2107.48 (11)C9—C13—H13A110.9
C8—C1—S1127.76 (10)C12—C13—H13A110.9
C2—C1—S1123.69 (10)C9—C13—H13B110.9
C7—C2—C3119.27 (12)C12—C13—H13B110.9
C7—C2—C1104.57 (12)H13A—C13—H13B108.9
C3—C2—C1136.16 (12)C15—C14—C19119.42 (13)
C4—C3—C2118.62 (13)C15—C14—C8121.46 (13)
C4—C3—H3120.7C19—C14—C8118.93 (13)
C2—C3—H3120.7C16—C15—C14120.27 (13)
C3—C4—C5119.61 (13)C16—C15—H15119.9
C3—C4—C9121.76 (13)C14—C15—H15119.9
C5—C4—C9118.61 (12)C17—C16—C15118.14 (14)
C6—C5—C4122.97 (13)C17—C16—H16120.9
C6—C5—H5118.5C15—C16—H16120.9
C4—C5—H5118.5F1—C17—C18118.51 (14)
C7—C6—C5115.49 (13)F1—C17—C16117.95 (14)
C7—C6—H6122.3C18—C17—C16123.54 (14)
C5—C6—H6122.3C17—C18—C19117.95 (14)
O1—C7—C6125.26 (13)C17—C18—H18121.0
O1—C7—C2110.72 (11)C19—C18—H18121.0
C6—C7—C2124.02 (13)C18—C19—C14120.62 (14)
C1—C8—O1110.16 (12)C18—C19—H19119.7
C1—C8—C14136.71 (12)C14—C19—H19119.7
O1—C8—C14113.13 (11)C21—C20—C22112.09 (14)
C4—C9—C13117.50 (13)C21—C20—S1110.77 (11)
C4—C9—C10114.43 (12)C22—C20—S1108.30 (11)
C13—C9—C10101.96 (14)C21—C20—H20108.5
C4—C9—H9107.5C22—C20—H20108.5
C13—C9—H9107.5S1—C20—H20108.5
C10—C9—H9107.5C20—C21—H21A109.5
C11—C10—C9104.54 (13)C20—C21—H21B109.5
C11—C10—H10A110.8H21A—C21—H21B109.5
C9—C10—H10A110.8C20—C21—H21C109.5
C11—C10—H10B110.8H21A—C21—H21C109.5
C9—C10—H10B110.8H21B—C21—H21C109.5
H10A—C10—H10B108.9C20—C22—H22A109.5
C10—C11—C12105.45 (14)C20—C22—H22B109.5
C10—C11—H11A110.7H22A—C22—H22B109.5
C12—C11—H11A110.7C20—C22—H22C109.5
C10—C11—H11B110.7H22A—C22—H22C109.5
C12—C11—H11B110.7H22B—C22—H22C109.5
H11A—C11—H11B108.8
O2—S1—C1—C826.55 (15)C3—C4—C9—C1343.8 (2)
O3—S1—C1—C8156.74 (12)C5—C4—C9—C13138.05 (15)
C20—S1—C1—C889.36 (14)C3—C4—C9—C1075.76 (18)
O2—S1—C1—C2166.81 (11)C5—C4—C9—C10102.40 (16)
O3—S1—C1—C236.62 (13)C4—C9—C10—C11168.08 (13)
C20—S1—C1—C277.28 (12)C13—C9—C10—C1140.14 (16)
C8—C1—C2—C70.33 (15)C9—C10—C11—C1225.31 (18)
S1—C1—C2—C7168.63 (10)C10—C11—C12—C130.8 (2)
C8—C1—C2—C3179.94 (15)C4—C9—C13—C12165.45 (14)
S1—C1—C2—C311.1 (2)C10—C9—C13—C1239.50 (17)
C7—C2—C3—C41.0 (2)C11—C12—C13—C924.25 (19)
C1—C2—C3—C4178.68 (15)C1—C8—C14—C1545.9 (2)
C2—C3—C4—C50.4 (2)O1—C8—C14—C15133.59 (13)
C2—C3—C4—C9177.73 (13)C1—C8—C14—C19139.22 (17)
C3—C4—C5—C60.4 (2)O1—C8—C14—C1941.31 (17)
C9—C4—C5—C6178.60 (13)C19—C14—C15—C162.3 (2)
C4—C5—C6—C70.5 (2)C8—C14—C15—C16172.62 (13)
C8—O1—C7—C6178.93 (13)C14—C15—C16—C171.3 (2)
C8—O1—C7—C20.37 (15)C15—C16—C17—F1178.20 (13)
C5—C6—C7—O1179.33 (13)C15—C16—C17—C181.0 (2)
C5—C6—C7—C20.1 (2)F1—C17—C18—C19176.99 (14)
C3—C2—C7—O1179.78 (12)C16—C17—C18—C192.2 (3)
C1—C2—C7—O10.43 (15)C17—C18—C19—C141.2 (2)
C3—C2—C7—C60.9 (2)C15—C14—C19—C181.0 (2)
C1—C2—C7—C6178.88 (13)C8—C14—C19—C18173.99 (14)
C2—C1—C8—O10.11 (15)O2—S1—C20—C2151.63 (13)
S1—C1—C8—O1168.26 (10)O3—S1—C20—C21179.29 (12)
C2—C1—C8—C14179.37 (15)C1—S1—C20—C2165.87 (13)
S1—C1—C8—C1412.3 (3)O2—S1—C20—C2271.66 (12)
C7—O1—C8—C10.15 (15)O3—S1—C20—C2257.41 (12)
C7—O1—C8—C14179.77 (11)C1—S1—C20—C22170.83 (11)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.952.603.3341 (17)135
C18—H18···O3ii0.952.483.2932 (19)144
C21—H21A···Cg1iii0.982.713.693 (2)177
Symmetry codes: (i) x1, y, z; (ii) x+3/2, y1/2, z+1/2; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H23FO3S
Mr386.46
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.4736 (3), 19.6185 (7), 10.8018 (3)
β (°) 108.833 (1)
V3)1900.12 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.40 × 0.39 × 0.36
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.678, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
18610, 4714, 3948
Rint0.030
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.103, 1.03
No. of reflections4714
No. of parameters246
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.35

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
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.952.603.3341 (17)134.5
C18—H18···O3ii0.952.483.2932 (19)144.0
C21—H21A···Cg1iii0.982.713.693 (2)177.3
Symmetry codes: (i) x1, y, z; (ii) x+3/2, y1/2, z+1/2; (iii) x+1, y+1, z.
 

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

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., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1000.  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 citationSeo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2591.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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