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ISSN: 2056-9890

5-Cyclo­hexyl-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 29 August 2012; accepted 29 August 2012; online 5 September 2012)

In the title compound, C22H24O2S, the cyclo­hexyl ring adopts a chair conformation. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. In the methyl­sulfinyl group, the methyl group and S atom are disordered over two sets of sites, with site-occupancy factors of 0.58 (3) and 0.42 (3). In the ring of the 4-methyl­phenyl group, the four C atoms are disordered over two sets of sites, with site-occupancy factors of 0.858 (5) and 0.142 (5).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.]).

[Scheme 1]

Experimental

Crystal data
  • C22H24O2S

  • Mr = 352.47

  • Monoclinic, P 21 /c

  • a = 16.4392 (5) Å

  • b = 7.2726 (2) Å

  • c = 15.8433 (5) Å

  • β = 108.652 (1)°

  • V = 1794.67 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 173 K

  • 0.40 × 0.33 × 0.29 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 = 0.671, Tmax = 0.746

  • 16617 measured reflections

  • 4447 independent reflections

  • 3204 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.204

  • S = 1.06

  • 4447 reflections

  • 280 parameters

  • 83 restraints

  • H-atom parameters constrained

  • Δρmax = 0.84 e Å−3

  • Δρmin = −0.68 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
C6—H6⋯O2i 0.95 2.60 3.405 (3) 143
C21—H21ACgii 0.98 2.89 3.619 (3) 137
C21—H21CCgiii 0.98 2.97 3.665 (3) 137
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -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-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2011a) and 4-fluorophenyl (Choi et al., 2011b) substituents in 2-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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring has a chair conformation. In the methylsulfinyl group, the C22 and S1 atoms are disordered over two positions with site-occupancy factors, from refinement of 0.58 (3) (part A) and 0.42 (3) (part B). In the phenyl ring of the 4-methylphenyl group, the four C atoms (C16/C17/C19/C20) are disordered over two positions with site-occupancy factors, from refinement of 0.858 (5) (part C) and 0.142 (5) (part D). In the crystal structure (Fig. 2), molecules are connected by weak C–H···O and C–H···π interactions (Table 1, Cg is the centroid of the C2-C7 benzene ring).

Related literature top

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

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (302 mg, 0.9 mmol) in dichloromethane (30 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 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 74%, m.p. 442-443 K; Rf = 0.63 (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 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 and methylene, and 1.5Ueq(C) for methyl H atoms. The positions of methyl, methylene and methine hydrogens were optimized rotationally. The C22 and S1 atoms of the methylsulfinyl group is disordered over two positions with site-occupancy factors, from refinement of of 0.58 (3) (part A) and 0.42 (3) (part B). The distance of equivalent S–C and S–O pairs were restrained to 1.790 (3) and 1.500 (3) Å using command DFIX, and displacement ellipsoids of C22 and S1 set were restrained to 0.01 using SHELXL command ISOR, respectively. In the phenyl ring of the 4-methylphenyl group, the C16/C17/C19/C20 atoms are disordered over two positions with site-occupancy factors, from refinement of 0.858 (5) (part C) and 0.142 (5) (part D). The distance of equivalent C-C pairs were restrained to 1.400 (3) Å using command DFIX, and displacement ellipsoids of C16/C17/C19/C20 sets were restrained to 0.01 using command ISOR.

Structure description top

As a part of our ongoing study of 5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2011a) and 4-fluorophenyl (Choi et al., 2011b) substituents in 2-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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring has a chair conformation. In the methylsulfinyl group, the C22 and S1 atoms are disordered over two positions with site-occupancy factors, from refinement of 0.58 (3) (part A) and 0.42 (3) (part B). In the phenyl ring of the 4-methylphenyl group, the four C atoms (C16/C17/C19/C20) are disordered over two positions with site-occupancy factors, from refinement of 0.858 (5) (part C) and 0.142 (5) (part D). In the crystal structure (Fig. 2), molecules are connected by weak C–H···O and C–H···π interactions (Table 1, Cg is the centroid of the C2-C7 benzene ring).

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

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. The C22 and S1 atoms of the methylsulfinyl group is disordered over two positions with site occupancy factors, from refinement of 0.58 (3) (part A) and 0.42 (3) (part B). In the phenyl ring of the 4-methylphenyl group, the C16/C17/C19/C20 atoms are disordered over two positions with site-occupancy factors, from refinement of 0.858 (5) (part C) and 0.142 (5) (part D).
[Figure 2] Fig. 2. A view of the C–H···O and 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 and D atoms were omitted for clarity. [Symmetry codes: (i) x, - y + 3/2, z + 1/2; (ii) - x, - y + 2, - z + 1; (iii) - x, - y + 1 ,- z + 1; (iv) x, - y + 3/2, z - 1/2.]
5-Cyclohexyl-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C22H24O2SF(000) = 752
Mr = 352.47Dx = 1.305 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5036 reflections
a = 16.4392 (5) Åθ = 2.6–28.3°
b = 7.2726 (2) ŵ = 0.19 mm1
c = 15.8433 (5) ÅT = 173 K
β = 108.652 (1)°Block, colourless
V = 1794.67 (9) Å30.40 × 0.33 × 0.29 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
4447 independent reflections
Radiation source: rotating anode3204 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.037
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.6°
φ and ω scansh = 2121
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 97
Tmin = 0.671, Tmax = 0.746l = 2021
16617 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)] = 0.064Hydrogen site location: difference Fourier map
wR(F2) = 0.204H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1164P)2 + 0.6896P]
where P = (Fo2 + 2Fc2)/3
4447 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.84 e Å3
83 restraintsΔρmin = 0.68 e Å3
Crystal data top
C22H24O2SV = 1794.67 (9) Å3
Mr = 352.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.4392 (5) ŵ = 0.19 mm1
b = 7.2726 (2) ÅT = 173 K
c = 15.8433 (5) Å0.40 × 0.33 × 0.29 mm
β = 108.652 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
4447 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3204 reflections with I > 2σ(I)
Tmin = 0.671, Tmax = 0.746Rint = 0.037
16617 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06483 restraints
wR(F2) = 0.204H-atom parameters constrained
S = 1.06Δρmax = 0.84 e Å3
4447 reflectionsΔρmin = 0.68 e Å3
280 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)
S1A0.1071 (3)0.7252 (6)0.3361 (4)0.0252 (8)0.58 (3)
S1B0.1117 (5)0.7405 (10)0.3352 (6)0.0397 (18)0.42 (3)
O10.12467 (10)0.75238 (19)0.59015 (11)0.0241 (4)
O20.17368 (13)0.6013 (3)0.32049 (13)0.0552 (6)
C10.13693 (13)0.7551 (3)0.45074 (15)0.0221 (5)
C20.22173 (14)0.7527 (3)0.51491 (15)0.0212 (5)
C30.30555 (14)0.7503 (3)0.51048 (15)0.0218 (5)
H30.31510.74860.45440.026*
C40.37431 (14)0.7506 (3)0.58871 (15)0.0215 (5)
C50.35942 (15)0.7514 (3)0.67138 (16)0.0258 (5)
H50.40720.75150.72450.031*
C60.27707 (15)0.7520 (3)0.67783 (16)0.0268 (5)
H60.26720.75260.73370.032*
C70.21044 (14)0.7518 (3)0.59833 (15)0.0225 (5)
C80.07917 (13)0.7542 (3)0.50148 (15)0.0216 (5)
C90.46566 (14)0.7488 (3)0.58568 (15)0.0227 (5)
H90.46220.74840.52150.027*
C100.51523 (14)0.5758 (4)0.62860 (16)0.0328 (6)
H10A0.51950.57150.69230.039*
H10B0.48350.46520.59920.039*
C110.60521 (15)0.5740 (4)0.62039 (17)0.0385 (6)
H11A0.63670.46480.65160.046*
H11B0.60090.56440.55680.046*
C120.65480 (17)0.7463 (4)0.65976 (19)0.0453 (8)
H12A0.66620.74670.72500.054*
H12B0.71080.74530.64880.054*
C130.60627 (15)0.9196 (4)0.62008 (17)0.0389 (7)
H13A0.60200.92830.55650.047*
H13B0.63831.02830.65120.047*
C140.51605 (14)0.9202 (4)0.62825 (16)0.0319 (6)
H14A0.52040.92520.69200.038*
H14B0.48491.03130.59880.038*
C150.01307 (13)0.7544 (3)0.47842 (13)0.0220 (5)
C180.19280 (14)0.7538 (3)0.44006 (14)0.0258 (5)
C16C0.06670 (13)0.8143 (4)0.39572 (16)0.0267 (7)0.858 (5)
H16C0.04270.85660.35210.032*0.858 (5)
C17C0.15553 (14)0.8122 (4)0.37691 (17)0.0286 (7)0.858 (5)
H17C0.19140.85140.32000.034*0.858 (5)
C19C0.13836 (14)0.7002 (4)0.52330 (16)0.0257 (6)0.858 (5)
H19C0.16230.66300.56780.031*0.858 (5)
C20C0.04973 (15)0.6999 (4)0.54265 (18)0.0271 (7)0.858 (5)
H20C0.01390.66230.59990.033*0.858 (5)
C16D0.0668 (7)0.685 (3)0.3974 (6)0.031 (4)0.142 (5)
H16D0.04240.63530.35550.038*0.142 (5)
C17D0.1562 (7)0.687 (3)0.3774 (8)0.034 (4)0.142 (5)
H17D0.19200.64380.32130.041*0.142 (5)
C19D0.1381 (7)0.795 (3)0.5255 (5)0.024 (4)*0.142 (5)
H19D0.16200.82120.57150.029*0.142 (5)
C20D0.0490 (8)0.800 (3)0.5447 (7)0.030 (4)0.142 (5)
H20D0.01300.83370.60250.035*0.142 (5)
C210.28860 (15)0.7517 (3)0.4204 (2)0.0347 (6)
H21A0.31360.86200.38650.052*
H21B0.30180.74960.47650.052*
H21C0.31270.64200.38540.052*
C22A0.1276 (5)0.9500 (7)0.3058 (4)0.0223 (16)0.58 (3)
H22A0.18690.98440.33900.033*0.58 (3)
H22B0.08811.03650.31980.033*0.58 (3)
H22C0.11940.95390.24170.033*0.58 (3)
C22B0.1599 (16)0.9450 (17)0.3132 (10)0.069 (4)0.42 (3)
H22D0.22240.93570.33930.103*0.42 (3)
H22E0.13931.05000.33940.103*0.42 (3)
H22F0.14460.96260.24870.103*0.42 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0228 (13)0.0305 (14)0.0237 (15)0.0006 (8)0.0095 (10)0.0053 (9)
S1B0.0250 (19)0.077 (4)0.017 (2)0.0061 (18)0.0069 (14)0.003 (2)
O10.0168 (7)0.0356 (10)0.0215 (8)0.0001 (6)0.0086 (6)0.0012 (6)
O20.0683 (14)0.0619 (14)0.0433 (11)0.0228 (11)0.0290 (10)0.0001 (10)
C10.0187 (10)0.0254 (11)0.0227 (11)0.0004 (8)0.0074 (8)0.0009 (8)
C20.0191 (10)0.0236 (11)0.0215 (10)0.0002 (8)0.0073 (8)0.0009 (8)
C30.0201 (10)0.0266 (12)0.0216 (10)0.0008 (8)0.0106 (8)0.0001 (8)
C40.0183 (10)0.0231 (11)0.0239 (11)0.0001 (8)0.0080 (8)0.0001 (8)
C50.0207 (10)0.0346 (13)0.0213 (11)0.0001 (9)0.0057 (8)0.0015 (9)
C60.0220 (11)0.0382 (14)0.0215 (11)0.0002 (9)0.0087 (9)0.0008 (9)
C70.0167 (10)0.0284 (12)0.0245 (11)0.0001 (8)0.0096 (8)0.0011 (8)
C80.0192 (10)0.0238 (11)0.0222 (11)0.0006 (8)0.0071 (8)0.0013 (8)
C90.0176 (10)0.0295 (12)0.0226 (11)0.0006 (8)0.0086 (8)0.0003 (8)
C100.0270 (11)0.0382 (14)0.0364 (13)0.0080 (10)0.0144 (10)0.0104 (11)
C110.0281 (12)0.0531 (17)0.0378 (13)0.0172 (12)0.0154 (10)0.0153 (13)
C120.0200 (11)0.087 (3)0.0273 (13)0.0037 (12)0.0054 (10)0.0006 (13)
C130.0252 (11)0.0562 (18)0.0375 (13)0.0143 (12)0.0130 (10)0.0143 (13)
C140.0242 (11)0.0401 (14)0.0339 (12)0.0059 (10)0.0127 (9)0.0091 (11)
C150.0179 (10)0.0220 (11)0.0275 (12)0.0007 (8)0.0095 (9)0.0028 (8)
C180.0195 (10)0.0250 (12)0.0342 (13)0.0004 (8)0.0107 (9)0.0049 (9)
C16C0.0212 (12)0.0342 (17)0.0264 (13)0.0013 (11)0.0101 (10)0.0003 (12)
C17C0.0196 (12)0.0377 (18)0.0272 (13)0.0018 (11)0.0056 (10)0.0010 (12)
C19C0.0235 (13)0.0254 (16)0.0329 (15)0.0007 (11)0.0156 (11)0.0009 (11)
C20C0.0220 (13)0.0310 (17)0.0295 (14)0.0006 (12)0.0100 (10)0.0022 (13)
C16D0.036 (7)0.041 (9)0.028 (7)0.003 (6)0.024 (6)0.002 (6)
C17D0.035 (7)0.037 (9)0.030 (7)0.001 (7)0.011 (6)0.005 (7)
C20D0.026 (7)0.036 (8)0.027 (7)0.003 (6)0.010 (6)0.002 (7)
C210.0201 (11)0.0448 (16)0.0410 (14)0.0021 (10)0.0123 (10)0.0026 (11)
C22A0.021 (3)0.025 (3)0.022 (2)0.0064 (18)0.010 (2)0.0050 (16)
C22B0.074 (8)0.095 (7)0.053 (5)0.046 (6)0.041 (6)0.013 (5)
Geometric parameters (Å, º) top
S1A—O21.499 (2)C13—H13A0.9900
S1A—C11.736 (6)C13—H13B0.9900
S1A—C22A1.767 (3)C14—H14A0.9900
S1B—O21.507 (3)C14—H14B0.9900
S1B—C11.745 (9)C15—C16C1.395 (2)
S1B—C22B1.772 (3)C15—C20C1.396 (2)
O1—C81.364 (3)C15—C20D1.400 (3)
O1—C71.374 (2)C15—C16D1.400 (3)
C1—C81.427 (2)C18—C19C1.392 (2)
C1—C21.439 (3)C18—C17C1.396 (2)
C2—C71.392 (3)C18—C19D1.398 (3)
C2—C31.402 (3)C18—C17D1.401 (3)
C3—C41.385 (3)C18—C211.505 (3)
C3—H30.9500C16C—C17C1.394 (2)
C4—C51.407 (3)C16C—H16C0.9500
C4—C91.518 (3)C17C—H17C0.9500
C5—C61.390 (3)C19C—C20C1.390 (2)
C5—H50.9500C19C—H19C0.9500
C6—C71.380 (3)C20C—H20C0.9500
C6—H60.9500C16D—C17D1.401 (3)
C8—C151.442 (3)C16D—H16D0.9500
C9—C141.529 (3)C17D—H17D0.9500
C9—C101.535 (3)C19D—C20D1.398 (3)
C9—H91.0000C19D—H19D0.9500
C10—C111.526 (3)C20D—H20D0.9500
C10—H10A0.9900C21—H21A0.9800
C10—H10B0.9900C21—H21B0.9800
C11—C121.517 (4)C21—H21C0.9800
C11—H11A0.9900C22A—H22A0.9800
C11—H11B0.9900C22A—H22B0.9800
C12—C131.516 (4)C22A—H22C0.9800
C12—H12A0.9900C22B—H22D0.9800
C12—H12B0.9900C22B—H22E0.9800
C13—C141.529 (3)C22B—H22F0.9800
O2—S1A—C1105.7 (3)C14—C13—H13B109.4
O2—S1A—C22A107.3 (3)H13A—C13—H13B108.0
C1—S1A—C22A98.9 (3)C9—C14—C13111.32 (19)
O2—S1B—C1104.9 (4)C9—C14—H14A109.4
O2—S1B—C22B99.6 (7)C13—C14—H14A109.4
C1—S1B—C22B100.6 (6)C9—C14—H14B109.4
C8—O1—C7107.78 (16)C13—C14—H14B109.4
C8—C1—C2105.71 (19)H14A—C14—H14B108.0
C8—C1—S1A124.9 (2)C16C—C15—C20C118.9 (2)
C2—C1—S1A128.6 (2)C16C—C15—C20D109.9 (7)
C8—C1—S1B127.8 (3)C20C—C15—C16D105.8 (6)
C2—C1—S1B126.3 (3)C20D—C15—C16D118.7 (8)
C7—C2—C3118.6 (2)C16C—C15—C8122.42 (19)
C7—C2—C1106.12 (19)C20C—C15—C8118.64 (19)
C3—C2—C1135.3 (2)C20D—C15—C8118.2 (6)
C4—C3—C2119.3 (2)C16D—C15—C8122.4 (5)
C4—C3—H3120.4C19C—C18—C17C117.9 (2)
C2—C3—H3120.4C17C—C18—C19D109.5 (6)
C3—C4—C5119.9 (2)C19C—C18—C17D106.4 (7)
C3—C4—C9120.3 (2)C19D—C18—C17D118.2 (8)
C5—C4—C9119.9 (2)C19C—C18—C21120.4 (2)
C6—C5—C4122.1 (2)C17C—C18—C21121.7 (2)
C6—C5—H5118.9C19D—C18—C21120.6 (6)
C4—C5—H5118.9C17D—C18—C21120.5 (5)
C7—C6—C5116.1 (2)C17C—C16C—C15120.1 (2)
C7—C6—H6121.9C17C—C16C—H16C119.9
C5—C6—H6121.9C15—C16C—H16C119.9
O1—C7—C6125.3 (2)C16C—C17C—C18121.3 (2)
O1—C7—C2110.78 (19)C16C—C17C—H17C119.3
C6—C7—C2124.0 (2)C18—C17C—H17C119.3
O1—C8—C1109.61 (18)C20C—C19C—C18121.4 (2)
O1—C8—C15116.54 (17)C20C—C19C—H19C119.3
C1—C8—C15133.8 (2)C18—C19C—H19C119.3
C4—C9—C14112.41 (17)C19C—C20C—C15120.4 (2)
C4—C9—C10112.55 (17)C19C—C20C—H20C119.8
C14—C9—C10109.7 (2)C15—C20C—H20C119.8
C4—C9—H9107.3C15—C16D—C17D120.7 (10)
C14—C9—H9107.3C15—C16D—H16D119.6
C10—C9—H9107.3C17D—C16D—H16D119.6
C11—C10—C9111.17 (19)C16D—C17D—C18120.1 (10)
C11—C10—H10A109.4C16D—C17D—H17D119.9
C9—C10—H10A109.4C18—C17D—H17D119.9
C11—C10—H10B109.4C18—C19D—C20D121.4 (11)
C9—C10—H10B109.4C18—C19D—H19D119.3
H10A—C10—H10B108.0C20D—C19D—H19D119.3
C12—C11—C10111.5 (2)C19D—C20D—C15119.7 (11)
C12—C11—H11A109.3C19D—C20D—H20D120.2
C10—C11—H11A109.3C15—C20D—H20D120.2
C12—C11—H11B109.3C18—C21—H21A109.5
C10—C11—H11B109.3C18—C21—H21B109.5
H11A—C11—H11B108.0H21A—C21—H21B109.5
C13—C12—C11112.0 (2)C18—C21—H21C109.5
C13—C12—H12A109.2H21A—C21—H21C109.5
C11—C12—H12A109.2H21B—C21—H21C109.5
C13—C12—H12B109.2S1B—C22B—H22D109.5
C11—C12—H12B109.2S1B—C22B—H22E109.5
H12A—C12—H12B107.9H22D—C22B—H22E109.5
C12—C13—C14111.3 (2)S1B—C22B—H22F109.5
C12—C13—H13A109.4H22D—C22B—H22F109.5
C14—C13—H13A109.4H22E—C22B—H22F109.5
C12—C13—H13B109.4
C1—S1A—O2—S1B92 (6)C9—C10—C11—C1255.7 (3)
C22A—S1A—O2—S1B13 (6)C10—C11—C12—C1354.2 (3)
C1—S1B—O2—S1A82 (6)C11—C12—C13—C1454.1 (3)
C22B—S1B—O2—S1A174 (6)C4—C9—C14—C13177.1 (2)
O2—S1A—C1—C8138.2 (3)C10—C9—C14—C1356.9 (3)
C22A—S1A—C1—C8110.9 (3)C12—C13—C14—C955.8 (3)
O2—S1A—C1—C229.8 (5)O1—C8—C15—C16C158.9 (2)
C22A—S1A—C1—C281.1 (4)C1—C8—C15—C16C21.2 (4)
O2—S1A—C1—S1B91 (3)O1—C8—C15—C20C18.4 (3)
C22A—S1A—C1—S1B20 (2)C1—C8—C15—C20C161.5 (2)
O2—S1B—C1—C8134.1 (4)O1—C8—C15—C20D16.1 (10)
C22B—S1B—C1—C8122.9 (8)C1—C8—C15—C20D164.0 (10)
O2—S1B—C1—C239.5 (7)O1—C8—C15—C16D154.0 (10)
C22B—S1B—C1—C263.6 (9)C1—C8—C15—C16D25.9 (10)
O2—S1B—C1—S1A82 (2)C20C—C15—C16C—C17C2.5 (4)
C22B—S1B—C1—S1A175 (3)C20D—C15—C16C—C17C34.3 (9)
C8—C1—C2—C70.4 (2)C16D—C15—C16C—C17C77.1 (8)
S1A—C1—C2—C7170.1 (3)C8—C15—C16C—C17C179.8 (2)
S1B—C1—C2—C7175.1 (3)C15—C16C—C17C—C181.1 (4)
C8—C1—C2—C3179.2 (2)C19C—C18—C17C—C16C1.0 (4)
S1A—C1—C2—C39.5 (4)C19D—C18—C17C—C16C31.2 (8)
S1B—C1—C2—C34.5 (5)C17D—C18—C17C—C16C79.8 (9)
C7—C2—C3—C41.2 (3)C21—C18—C17C—C16C179.8 (2)
C1—C2—C3—C4179.3 (2)C17C—C18—C19C—C20C1.6 (4)
C2—C3—C4—C50.6 (3)C19D—C18—C19C—C20C81.4 (12)
C2—C3—C4—C9179.76 (18)C17D—C18—C19C—C20C37.6 (8)
C3—C4—C5—C60.0 (3)C21—C18—C19C—C20C179.5 (2)
C9—C4—C5—C6179.66 (19)C18—C19C—C20C—C150.2 (4)
C4—C5—C6—C70.0 (3)C16C—C15—C20C—C19C1.9 (4)
C8—O1—C7—C6179.2 (2)C20D—C15—C20C—C19C81.8 (12)
C8—O1—C7—C20.2 (2)C16D—C15—C20C—C19C38.6 (8)
C5—C6—C7—O1179.97 (19)C8—C15—C20C—C19C179.3 (2)
C5—C6—C7—C20.6 (3)C16C—C15—C16D—C17D76.9 (17)
C3—C2—C7—O1179.35 (17)C20C—C15—C16D—C17D39.6 (18)
C1—C2—C7—O10.3 (2)C20D—C15—C16D—C17D10 (2)
C3—C2—C7—C61.2 (3)C8—C15—C16D—C17D179.9 (13)
C1—C2—C7—C6179.1 (2)C15—C16D—C17D—C182 (3)
C7—O1—C8—C10.1 (2)C19C—C18—C17D—C16D36.2 (18)
C7—O1—C8—C15179.79 (16)C17C—C18—C17D—C16D78.3 (17)
C2—C1—C8—O10.3 (2)C19D—C18—C17D—C16D8 (2)
S1A—C1—C8—O1170.5 (2)C21—C18—C17D—C16D178.1 (13)
S1B—C1—C8—O1174.9 (3)C19C—C18—C19D—C20D82.3 (18)
C2—C1—C8—C15179.6 (2)C17C—C18—C19D—C20D30.3 (18)
S1A—C1—C8—C159.3 (4)C17D—C18—C19D—C20D10 (2)
S1B—C1—C8—C155.0 (4)C21—C18—C19D—C20D179.3 (13)
C3—C4—C9—C14118.1 (2)C18—C19D—C20D—C153 (3)
C5—C4—C9—C1462.3 (3)C16C—C15—C20D—C19D35.0 (19)
C3—C4—C9—C10117.5 (2)C20C—C15—C20D—C19D78.6 (17)
C5—C4—C9—C1062.2 (3)C16D—C15—C20D—C19D7 (2)
C4—C9—C10—C11177.2 (2)C8—C15—C20D—C19D177.8 (13)
C14—C9—C10—C1156.8 (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
C6—H6···O2i0.952.603.405 (3)143
C21—H21A···Cgii0.982.893.619 (3)137
C21—H21C···Cgiii0.982.973.665 (3)137
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+2, z+1; (iii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC22H24O2S
Mr352.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)16.4392 (5), 7.2726 (2), 15.8433 (5)
β (°) 108.652 (1)
V3)1794.67 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.40 × 0.33 × 0.29
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.671, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
16617, 4447, 3204
Rint0.037
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.204, 1.06
No. of reflections4447
No. of parameters280
No. of restraints83
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.84, 0.68

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
C6—H6···O2i0.952.603.405 (3)143
C21—H21A···Cgii0.982.893.619 (3)137
C21—H21C···Cgiii0.982.973.665 (3)137
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+2, z+1; (iii) x, y+1, 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.  Google Scholar
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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