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

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ISSN: 2056-9890

5-Cyclo­pentyl-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-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 8 October 2012; accepted 9 October 2012; online 13 October 2012)

In the title compound, C21H22O2S, the cyclo­pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The benzofuran unit is essentially planar, with a mean deviation from the least-squares plane defined by the nine constituent ring atoms of 0.008 (2) Å. In the crystal, mol­ecules are linked via pairs of C—H⋯π inter­actions, forming inversion dimers. In the ring of the 4-methyl­phenyl group, four C atoms and their attached H atoms are disordered over two sets of sites, with site-ccupancy factors of 0.899 (5) and 0.10.

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
  • C21H22O2S

  • Mr = 338.45

  • Monoclinic, P 21 /c

  • a = 15.2869 (5) Å

  • b = 7.2881 (3) Å

  • c = 15.3608 (6) Å

  • β = 97.599 (2)°

  • V = 1696.35 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 173 K

  • 0.29 × 0.23 × 0.17 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 = 0.653, Tmax = 0.746

  • 12919 measured reflections

  • 2994 independent reflections

  • 2154 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.173

  • S = 1.07

  • 2994 reflections

  • 212 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.86 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A D—H H⋯A DA D—H⋯A
C20—H20BCgi 0.98 2.78 3.665 (2) 150
Symmetry code: (i) -x+1, -y, -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 ongoing study of 5-cyclopentyl-3-methylsulfinyl-1-benzofuran derivatives containing 2-phenyl (Choi et al., 2011) and 2-(4-fluorophenyl) (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 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an envelope conformation. In the phenyl ring of the 4-methylphenyl group, the four C atoms (C15/C16/C18/C19) are disordered over two positions with site-ccupancy factors, from refinement of of 0.899 (5) (part A) and 0.101 (5) (part B). In the crystal structure, molecules are connected via pairs of weak C—H···π interactions (Fig. 2 & Table 1, Cg is the centroid of the C2–C7 benzene ring), forming inversion dimers.

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%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (290 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 424–425 K; Rf = 0.65 (hexane–ethyl acetate, 1:1 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. In the phenyl ring of the 4-methylphenyl group, the C15/C16/C18/C19 atoms are disordered over two positions with site occupancy factors, from refinement of of 0.899 (5) (part A) and 0.101 (5) (part B). The distance of equivalent C–C pairs were restrained to 0.002 Å using the SHELXL-97 command SADI, and C14 and C17 set, was refined using EXYZ,and C14–C19 set was refined using EADP.

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. In the phenyl ring of the 4-methylphenyl group, the C15/C16/C18/C19 atoms are disordered over two positions with site-ccupancy factors, from refinement of 0.899 (5) (part A) and 0.101 (5) (part B).
[Figure 2] Fig. 2. A view of C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding and disordered part B atoms were omitted for clarity. [Symmetry code: (i) - x + 1, - y, - z + 1.]
5-Cyclopentyl-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C21H22O2SF(000) = 720
Mr = 338.45Dx = 1.325 Mg m3
Monoclinic, P21/cMelting point = 424–425 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.2869 (5) ÅCell parameters from 2479 reflections
b = 7.2881 (3) Åθ = 2.7–28.1°
c = 15.3608 (6) ŵ = 0.20 mm1
β = 97.599 (2)°T = 173 K
V = 1696.35 (11) Å3Block, colourless
Z = 40.29 × 0.23 × 0.17 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2994 independent reflections
Radiation source: rotating anode2154 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.043
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 2.7°
ϕ– and ω–scansh = 1818
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 88
Tmin = 0.653, Tmax = 0.746l = 1618
12919 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)] = 0.059Hydrogen site location: difference Fourier map
wR(F2) = 0.173H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0828P)2 + 1.5926P]
where P = (Fo2 + 2Fc2)/3
2994 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.86 e Å3
14 restraintsΔρmin = 0.36 e Å3
Crystal data top
C21H22O2SV = 1696.35 (11) Å3
Mr = 338.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.2869 (5) ŵ = 0.20 mm1
b = 7.2881 (3) ÅT = 173 K
c = 15.3608 (6) Å0.29 × 0.23 × 0.17 mm
β = 97.599 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
2994 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2154 reflections with I > 2σ(I)
Tmin = 0.653, Tmax = 0.746Rint = 0.043
12919 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05914 restraints
wR(F2) = 0.173H-atom parameters constrained
S = 1.07Δρmax = 0.86 e Å3
2994 reflectionsΔρmin = 0.36 e Å3
212 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*/UeqOcc. (<1)
S10.39884 (5)0.23817 (10)0.27487 (5)0.0298 (3)
O20.33603 (17)0.1030 (4)0.22826 (15)0.0577 (7)
O10.37504 (12)0.2498 (2)0.52846 (12)0.0243 (5)
C10.36912 (17)0.2579 (3)0.38147 (18)0.0231 (6)
C20.27970 (17)0.2531 (3)0.40194 (18)0.0214 (6)
C30.19556 (17)0.2513 (3)0.35376 (18)0.0230 (6)
H30.18850.25160.29140.028*
C40.12236 (18)0.2493 (3)0.39841 (19)0.0228 (6)
C50.13432 (18)0.2478 (3)0.49058 (18)0.0248 (6)
H50.08370.24710.52040.030*
C60.21657 (18)0.2473 (3)0.53943 (18)0.0253 (6)
H60.22390.24590.60180.030*
C70.28779 (17)0.2491 (3)0.49274 (18)0.0224 (6)
C80.42346 (17)0.2554 (3)0.45874 (18)0.0224 (6)
C90.03109 (17)0.2503 (3)0.34703 (19)0.0244 (6)
H90.03800.24720.28320.029*
C100.02605 (17)0.4168 (4)0.36192 (19)0.0309 (7)
H10A0.00440.52840.33490.037*
H10B0.02690.43910.42540.037*
C110.11767 (18)0.3623 (5)0.3166 (2)0.0388 (8)
H11A0.12600.40380.25470.047*
H11B0.16430.41780.34720.047*
C120.12123 (18)0.1522 (5)0.3216 (2)0.0382 (8)
H12A0.13470.09880.26210.046*
H12B0.16720.11260.35730.046*
C130.02941 (17)0.0915 (4)0.3647 (2)0.0319 (7)
H13A0.02880.07220.42850.038*
H13B0.01110.02350.33790.038*
C14A0.51894 (17)0.2566 (3)0.48277 (18)0.0232 (7)0.899 (5)
C15A0.57418 (15)0.3215 (5)0.4245 (2)0.0300 (5)0.899 (5)
H15A0.54950.36880.36900.036*0.899 (5)
C16A0.66532 (18)0.3175 (5)0.4470 (2)0.0300 (5)0.899 (5)
H16A0.70220.35840.40570.036*0.899 (5)
C17A0.70343 (17)0.2548 (3)0.52866 (19)0.0262 (7)0.899 (5)
C18A0.64777 (15)0.1982 (5)0.5875 (2)0.0300 (5)0.899 (5)
H18A0.67240.15850.64440.036*0.899 (5)
C19A0.55714 (18)0.1983 (5)0.5653 (2)0.0300 (5)0.899 (5)
H19A0.52050.15810.60690.036*0.899 (5)
C14B0.51894 (17)0.2566 (3)0.48277 (18)0.0232 (7)0.10
C15B0.5736 (12)0.174 (4)0.4248 (19)0.0300 (5)0.10
H15B0.54890.11840.37110.036*0.101 (5)
C16B0.6644 (13)0.178 (4)0.4502 (10)0.0300 (5)0.10
H16B0.70160.12610.41190.036*0.101 (5)
C17B0.70343 (17)0.2548 (3)0.52866 (19)0.0262 (7)0.10
C18B0.6487 (11)0.308 (4)0.5890 (11)0.0300 (5)0.10
H18B0.67340.34350.64650.036*0.101 (5)
C19B0.5582 (12)0.309 (4)0.5658 (8)0.0300 (5)0.10
H19B0.52170.34680.60800.036*0.101 (5)
C200.80136 (18)0.2528 (4)0.5536 (2)0.0351 (8)
H20A0.83000.29830.50440.053*
H20B0.82100.12710.56780.053*
H20C0.81720.33170.60490.053*
C210.3672 (2)0.4541 (5)0.2339 (2)0.0483 (9)
H21A0.36890.45640.17040.072*
H21B0.40780.54680.26230.072*
H21C0.30720.48080.24600.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0305 (4)0.0384 (5)0.0214 (4)0.0008 (3)0.0067 (3)0.0013 (3)
O20.0737 (17)0.0619 (17)0.0379 (14)0.0226 (14)0.0086 (12)0.0090 (13)
O10.0240 (10)0.0286 (11)0.0196 (10)0.0005 (8)0.0007 (8)0.0009 (8)
C10.0226 (13)0.0249 (14)0.0223 (14)0.0016 (11)0.0048 (11)0.0017 (11)
C20.0262 (14)0.0185 (13)0.0201 (14)0.0004 (10)0.0051 (11)0.0009 (11)
C30.0275 (14)0.0231 (14)0.0180 (14)0.0003 (11)0.0020 (11)0.0003 (11)
C40.0236 (14)0.0192 (14)0.0253 (15)0.0000 (10)0.0022 (11)0.0004 (11)
C50.0246 (14)0.0259 (15)0.0243 (15)0.0008 (11)0.0052 (11)0.0002 (12)
C60.0293 (15)0.0285 (15)0.0183 (14)0.0000 (11)0.0035 (11)0.0002 (12)
C70.0225 (14)0.0212 (14)0.0227 (15)0.0008 (11)0.0002 (11)0.0013 (11)
C80.0250 (14)0.0205 (14)0.0224 (14)0.0000 (11)0.0052 (11)0.0015 (11)
C90.0249 (14)0.0268 (15)0.0209 (14)0.0005 (11)0.0008 (11)0.0003 (12)
C100.0300 (15)0.0300 (16)0.0318 (17)0.0035 (12)0.0008 (12)0.0011 (13)
C110.0247 (16)0.049 (2)0.0411 (19)0.0059 (14)0.0006 (13)0.0031 (16)
C120.0257 (16)0.050 (2)0.0375 (18)0.0083 (14)0.0003 (13)0.0014 (15)
C130.0301 (15)0.0291 (16)0.0354 (17)0.0051 (12)0.0001 (13)0.0006 (13)
C14A0.0244 (14)0.0200 (14)0.0243 (15)0.0000 (11)0.0002 (11)0.0019 (11)
C15A0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C16A0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C17A0.0247 (14)0.0206 (14)0.0322 (17)0.0009 (11)0.0006 (12)0.0041 (12)
C18A0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C19A0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C14B0.0244 (14)0.0200 (14)0.0243 (15)0.0000 (11)0.0002 (11)0.0019 (11)
C15B0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C16B0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C17B0.0247 (14)0.0206 (14)0.0322 (17)0.0009 (11)0.0006 (12)0.0041 (12)
C18B0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C19B0.0283 (9)0.0332 (11)0.0279 (9)0.0013 (7)0.0020 (7)0.0012 (8)
C200.0241 (15)0.0390 (18)0.0413 (19)0.0006 (13)0.0007 (13)0.0002 (14)
C210.068 (2)0.052 (2)0.0264 (18)0.0205 (18)0.0108 (16)0.0108 (16)
Geometric parameters (Å, º) top
S1—O21.491 (2)C12—H12A0.9900
S1—C211.740 (3)C12—H12B0.9900
S1—C11.762 (3)C13—H13A0.9900
O1—C71.374 (3)C13—H13B0.9900
O1—C81.381 (3)C14A—C19A1.390 (4)
C1—C81.356 (4)C14A—C15A1.393 (3)
C1—C21.443 (4)C15A—C16A1.391 (3)
C2—C71.384 (4)C15A—H15A0.9500
C2—C31.397 (4)C16A—C17A1.389 (4)
C3—C41.388 (4)C16A—H16A0.9500
C3—H30.9500C17A—C18A1.384 (3)
C4—C51.403 (4)C17A—C201.496 (4)
C4—C91.510 (4)C18A—C19A1.382 (3)
C5—C61.376 (4)C18A—H18A0.9500
C5—H50.9500C19A—H19A0.9500
C6—C71.381 (4)C15B—C16B1.392 (3)
C6—H60.9500C15B—H15B0.9500
C8—C14A1.458 (4)C16B—H16B0.9500
C9—C131.528 (4)C18B—C19B1.383 (3)
C9—C101.529 (4)C18B—H18B0.9500
C9—H91.0000C19B—H19B0.9500
C10—C111.532 (4)C20—H20A0.9800
C10—H10A0.9900C20—H20B0.9800
C10—H10B0.9900C20—H20C0.9800
C11—C121.534 (5)C21—H21A0.9800
C11—H11A0.9900C21—H21B0.9800
C11—H11B0.9900C21—H21C0.9800
C12—C131.536 (4)
O2—S1—C21107.08 (17)C11—C12—C13105.8 (2)
O2—S1—C1105.74 (13)C11—C12—H12A110.6
C21—S1—C199.72 (14)C13—C12—H12A110.6
C7—O1—C8106.4 (2)C11—C12—H12B110.6
C8—C1—C2107.3 (2)C13—C12—H12B110.6
C8—C1—S1127.5 (2)H12A—C12—H12B108.7
C2—C1—S1124.6 (2)C9—C13—C12104.2 (2)
C7—C2—C3119.1 (2)C9—C13—H13A110.9
C7—C2—C1105.0 (2)C12—C13—H13A110.9
C3—C2—C1135.8 (3)C9—C13—H13B110.9
C4—C3—C2119.0 (2)C12—C13—H13B110.9
C4—C3—H3120.5H13A—C13—H13B108.9
C2—C3—H3120.5C19A—C14A—C15A118.2 (3)
C3—C4—C5119.5 (3)C19A—C14A—C8121.0 (2)
C3—C4—C9119.4 (2)C15A—C14A—C8120.8 (3)
C5—C4—C9121.0 (2)C16A—C15A—C14A120.4 (3)
C6—C5—C4122.5 (3)C16A—C15A—H15A119.8
C6—C5—H5118.7C14A—C15A—H15A119.8
C4—C5—H5118.7C17A—C16A—C15A121.2 (3)
C5—C6—C7116.3 (3)C17A—C16A—H16A119.4
C5—C6—H6121.9C15A—C16A—H16A119.4
C7—C6—H6121.9C18A—C17A—C16A117.9 (3)
O1—C7—C6125.7 (2)C18A—C17A—C20120.7 (3)
O1—C7—C2110.8 (2)C16A—C17A—C20121.4 (3)
C6—C7—C2123.5 (3)C19A—C18A—C17A121.4 (3)
C1—C8—O1110.5 (2)C19A—C18A—H18A119.3
C1—C8—C14A134.3 (3)C17A—C18A—H18A119.3
O1—C8—C14A115.2 (2)C18A—C19A—C14A120.8 (3)
C4—C9—C13116.3 (2)C18A—C19A—H19A119.6
C4—C9—C10115.6 (2)C14A—C19A—H19A119.6
C13—C9—C10101.7 (2)C16B—C15B—H15B121.4
C4—C9—H9107.6C15B—C16B—H16B118.3
C13—C9—H9107.6C19B—C18B—H18B119.9
C10—C9—H9107.6C18B—C19B—H19B119.0
C9—C10—C11103.4 (2)C17A—C20—H20A109.5
C9—C10—H10A111.1C17A—C20—H20B109.5
C11—C10—H10A111.1H20A—C20—H20B109.5
C9—C10—H10B111.1C17A—C20—H20C109.5
C11—C10—H10B111.1H20A—C20—H20C109.5
H10A—C10—H10B109.0H20B—C20—H20C109.5
C10—C11—C12105.8 (2)S1—C21—H21A109.5
C10—C11—H11A110.6S1—C21—H21B109.5
C12—C11—H11A110.6H21A—C21—H21B109.5
C10—C11—H11B110.6S1—C21—H21C109.5
C12—C11—H11B110.6H21A—C21—H21C109.5
H11A—C11—H11B108.7H21B—C21—H21C109.5
O2—S1—C1—C8133.7 (3)C7—O1—C8—C10.1 (3)
C21—S1—C1—C8115.4 (3)C7—O1—C8—C14A179.9 (2)
O2—S1—C1—C236.8 (3)C3—C4—C9—C13123.0 (3)
C21—S1—C1—C274.2 (3)C5—C4—C9—C1357.6 (3)
C8—C1—C2—C70.4 (3)C3—C4—C9—C10117.8 (3)
S1—C1—C2—C7172.45 (19)C5—C4—C9—C1061.6 (3)
C8—C1—C2—C3179.4 (3)C4—C9—C10—C11169.5 (2)
S1—C1—C2—C37.3 (4)C13—C9—C10—C1142.5 (3)
C7—C2—C3—C41.3 (4)C9—C10—C11—C1228.5 (3)
C1—C2—C3—C4179.0 (3)C10—C11—C12—C133.3 (3)
C2—C3—C4—C50.4 (4)C4—C9—C13—C12167.1 (2)
C2—C3—C4—C9179.1 (2)C10—C9—C13—C1240.5 (3)
C3—C4—C5—C60.4 (4)C11—C12—C13—C923.1 (3)
C9—C4—C5—C6179.8 (2)C1—C8—C14A—C19A160.3 (3)
C4—C5—C6—C70.2 (4)O1—C8—C14A—C19A19.4 (4)
C8—O1—C7—C6178.8 (2)C1—C8—C14A—C15A21.6 (4)
C8—O1—C7—C20.3 (3)O1—C8—C14A—C15A158.7 (3)
C5—C6—C7—O1179.7 (2)C19A—C14A—C15A—C16A3.6 (4)
C5—C6—C7—C20.7 (4)C8—C14A—C15A—C16A178.2 (3)
C3—C2—C7—O1179.4 (2)C14A—C15A—C16A—C17A2.1 (5)
C1—C2—C7—O10.4 (3)C15A—C16A—C17A—C18A0.7 (5)
C3—C2—C7—C61.5 (4)C15A—C16A—C17A—C20179.1 (3)
C1—C2—C7—C6178.7 (2)C16A—C17A—C18A—C19A2.0 (5)
C2—C1—C8—O10.2 (3)C20—C17A—C18A—C19A179.6 (3)
S1—C1—C8—O1171.98 (18)C17A—C18A—C19A—C14A0.4 (5)
C2—C1—C8—C14A179.6 (3)C15A—C14A—C19A—C18A2.4 (5)
S1—C1—C8—C14A7.8 (4)C8—C14A—C19A—C18A179.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C20—H20B···Cgi0.982.783.665 (2)150
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC21H22O2S
Mr338.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)15.2869 (5), 7.2881 (3), 15.3608 (6)
β (°) 97.599 (2)
V3)1696.35 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.29 × 0.23 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.653, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
12919, 2994, 2154
Rint0.043
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.173, 1.07
No. of reflections2994
No. of parameters212
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.86, 0.36

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
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C20—H20B···Cgi0.982.783.665 (2)150.2
Symmetry code: (i) x+1, y, z+1.
 

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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