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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1410

2,5-Di­methyl-3-(4-methyl­phenyl­sulfin­yl)-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 23 March 2012; accepted 10 April 2012; online 18 April 2012)

In the title compound, C17H16O2S, the 4-methyl­phenyl ring makes a dihedral angle of 88.28 (5)° with the mean plane [mean deviation = 0.009 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o543.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2551.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o584.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16O2S

  • Mr = 284.36

  • Orthorhombic, P n a 21

  • a = 13.072 (2) Å

  • b = 6.1790 (11) Å

  • c = 17.979 (3) Å

  • V = 1452.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 173 K

  • 0.37 × 0.23 × 0.14 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 = 0.624, Tmax = 0.746

  • 13920 measured reflections

  • 3587 independent reflections

  • 3101 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.090

  • S = 1.03

  • 3587 reflections

  • 184 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.24 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1729 Friedel pairs

  • Flack parameter: −0.01 (7)

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
C12—H12⋯O2i 0.95 2.60 3.334 (2) 134
C17—H17B⋯O1ii 0.98 2.52 3.387 (3) 148
C10—H10BCgiii 0.98 2.74 3.538 (3) 139
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (ii) [-x+1, -y+1, z+{\script{1\over 2}}]; (iii) x, 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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 2,5-dimethyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a), 3-(4-chlorophenylsulfinyl) (Choi et al., 2010b) and 3-(4-bromophenylsulfinyl) (Choi et al., 2012) 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 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4–methylphenyl ring and the mean plane of the benzofurn fragment is 88.28 (5)°. In the crystal structure, molecules are connected by weak intermolecular C—H···O hydrogen bonds (Fig. 2 & Table 1) and C—H···π interactions (Fig. 3 & 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. (2010a,b, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2,5-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (322 mg, 1.2 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 412–413 K; Rf = 0.44 (hexane:ethyl acetate, 2:1 v/v)]. 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 positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl 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, 1997) 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 hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen bonding were omitted for clarity. [Symmetry codes: (i) x - 1/2, - y + 1/2, z ; (ii) - x + 1, - y + 1, z + 1/2; (iv) x + 1/2, - y + 1/2, z; (v) - x + 1, - y + 1, z - 1/2.]
[Figure 3] Fig. 3. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen bonding were omitted for clarity. [Symmetry codes: (iii) x, y - 1, z; (vi) x, y + 1, z.]
2,5-Dimethyl-3-(4-methylphenylsulfinyl)-1-benzofuran top
Crystal data top
C17H16O2SF(000) = 600
Mr = 284.36Dx = 1.301 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4157 reflections
a = 13.072 (2) Åθ = 2.3–24.8°
b = 6.1790 (11) ŵ = 0.22 mm1
c = 17.979 (3) ÅT = 173 K
V = 1452.2 (4) Å3Block, colourless
Z = 40.37 × 0.23 × 0.14 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3587 independent reflections
Radiation source: rotating anode3101 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.036
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.3°
ϕ and ω scansh = 1716
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 88
Tmin = 0.624, Tmax = 0.746l = 2323
13920 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0445P)2 + 0.1605P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3587 reflectionsΔρmax = 0.20 e Å3
184 parametersΔρmin = 0.24 e Å3
1 restraintAbsolute structure: Flack (1983), 1729 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Crystal data top
C17H16O2SV = 1452.2 (4) Å3
Mr = 284.36Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 13.072 (2) ŵ = 0.22 mm1
b = 6.1790 (11) ÅT = 173 K
c = 17.979 (3) Å0.37 × 0.23 × 0.14 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3587 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3101 reflections with I > 2σ(I)
Tmin = 0.624, Tmax = 0.746Rint = 0.036
13920 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.090Δρmax = 0.20 e Å3
S = 1.03Δρmin = 0.24 e Å3
3587 reflectionsAbsolute structure: Flack (1983), 1729 Friedel pairs
184 parametersAbsolute structure parameter: 0.01 (7)
1 restraint
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
S10.68387 (4)0.23443 (8)0.43774 (3)0.05093 (14)
O10.60322 (10)0.2839 (2)0.22842 (8)0.0447 (3)
O20.79502 (12)0.2480 (3)0.45451 (10)0.0708 (5)
C10.66469 (12)0.3081 (3)0.34471 (11)0.0379 (4)
C20.70684 (12)0.4873 (2)0.30262 (10)0.0332 (3)
C30.77327 (12)0.6586 (3)0.31664 (11)0.0372 (4)
H30.80170.67840.36480.045*
C40.79736 (14)0.7997 (3)0.25939 (12)0.0424 (4)
C50.75333 (16)0.7692 (3)0.18910 (12)0.0482 (5)
H50.77020.86770.15040.058*
C60.68661 (15)0.6026 (3)0.17362 (10)0.0464 (4)
H60.65660.58500.12590.056*
C70.66586 (12)0.4626 (3)0.23164 (10)0.0373 (4)
C80.60458 (13)0.1927 (3)0.29798 (12)0.0419 (4)
C90.87197 (17)0.9835 (3)0.27175 (15)0.0580 (6)
H9A0.87091.02600.32430.087*
H9B0.85231.10730.24080.087*
H9C0.94100.93620.25820.087*
C100.54077 (15)0.0042 (3)0.30769 (17)0.0602 (6)
H10A0.54880.05920.35850.090*
H10B0.56260.11520.27220.090*
H10C0.46880.03200.29880.090*
C110.62497 (13)0.4678 (3)0.47906 (10)0.0407 (4)
C120.52077 (14)0.4978 (3)0.47194 (11)0.0455 (4)
H120.48090.39810.44400.055*
C130.47520 (14)0.6721 (4)0.50530 (11)0.0473 (4)
H130.40350.69230.50000.057*
C140.53160 (17)0.8206 (3)0.54687 (10)0.0472 (5)
C150.63554 (18)0.7839 (4)0.55478 (11)0.0529 (5)
H150.67530.88100.58380.063*
C160.68289 (14)0.6082 (4)0.52116 (11)0.0486 (5)
H160.75430.58510.52710.058*
C170.4802 (2)1.0140 (4)0.58236 (13)0.0626 (6)
H17A0.53211.10690.60530.094*
H17B0.43200.96430.62050.094*
H17C0.44311.09600.54430.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0432 (2)0.0524 (3)0.0572 (3)0.0094 (2)0.0020 (2)0.0228 (2)
O10.0372 (7)0.0416 (7)0.0554 (8)0.0033 (5)0.0021 (6)0.0123 (6)
O20.0427 (8)0.1013 (12)0.0683 (12)0.0268 (8)0.0071 (7)0.0186 (9)
C10.0299 (8)0.0329 (8)0.0510 (10)0.0048 (6)0.0042 (7)0.0049 (7)
C20.0281 (7)0.0322 (7)0.0393 (9)0.0079 (6)0.0039 (6)0.0027 (7)
C30.0280 (8)0.0372 (8)0.0463 (10)0.0022 (6)0.0015 (7)0.0002 (7)
C40.0330 (10)0.0349 (9)0.0592 (12)0.0053 (7)0.0113 (8)0.0065 (8)
C50.0470 (12)0.0485 (11)0.0491 (12)0.0105 (8)0.0163 (9)0.0134 (8)
C60.0486 (11)0.0535 (11)0.0372 (10)0.0151 (9)0.0034 (8)0.0018 (8)
C70.0311 (8)0.0378 (8)0.0429 (9)0.0078 (7)0.0009 (7)0.0067 (7)
C80.0281 (9)0.0335 (8)0.0642 (12)0.0062 (7)0.0052 (8)0.0022 (8)
C90.0430 (11)0.0409 (10)0.0902 (17)0.0045 (9)0.0144 (10)0.0083 (10)
C100.0396 (10)0.0380 (10)0.1032 (19)0.0061 (8)0.0087 (12)0.0085 (11)
C110.0326 (9)0.0529 (10)0.0367 (9)0.0013 (7)0.0003 (7)0.0173 (8)
C120.0329 (9)0.0591 (11)0.0445 (10)0.0029 (8)0.0024 (8)0.0038 (9)
C130.0319 (9)0.0677 (12)0.0422 (10)0.0019 (9)0.0002 (8)0.0051 (9)
C140.0505 (12)0.0567 (11)0.0344 (9)0.0048 (9)0.0035 (8)0.0120 (8)
C150.0536 (13)0.0640 (13)0.0411 (10)0.0184 (10)0.0084 (9)0.0090 (9)
C160.0321 (9)0.0685 (12)0.0451 (11)0.0071 (9)0.0069 (8)0.0181 (9)
C170.0751 (15)0.0605 (13)0.0521 (13)0.0027 (12)0.0094 (11)0.0035 (10)
Geometric parameters (Å, º) top
S1—O21.4864 (17)C9—H9B0.9800
S1—C11.751 (2)C9—H9C0.9800
S1—C111.795 (2)C10—H10A0.9800
O1—C81.372 (3)C10—H10B0.9800
O1—C71.376 (2)C10—H10C0.9800
C1—C81.354 (3)C11—C161.378 (3)
C1—C21.450 (2)C11—C121.381 (3)
C2—C31.392 (2)C12—C131.369 (3)
C2—C71.392 (3)C12—H120.9500
C3—C41.385 (3)C13—C141.394 (3)
C3—H30.9500C13—H130.9500
C4—C51.401 (3)C14—C151.385 (3)
C4—C91.513 (3)C14—C171.512 (3)
C5—C61.378 (3)C15—C161.388 (3)
C5—H50.9500C15—H150.9500
C6—C71.382 (3)C16—H160.9500
C6—H60.9500C17—H17A0.9800
C8—C101.485 (2)C17—H17B0.9800
C9—H9A0.9800C17—H17C0.9800
O2—S1—C1108.60 (9)H9A—C9—H9C109.5
O2—S1—C11106.86 (10)H9B—C9—H9C109.5
C1—S1—C1197.17 (8)C8—C10—H10A109.5
C8—O1—C7106.49 (14)C8—C10—H10B109.5
C8—C1—C2107.41 (17)H10A—C10—H10B109.5
C8—C1—S1122.59 (14)C8—C10—H10C109.5
C2—C1—S1129.99 (14)H10A—C10—H10C109.5
C3—C2—C7119.29 (16)H10B—C10—H10C109.5
C3—C2—C1136.31 (17)C16—C11—C12120.55 (18)
C7—C2—C1104.40 (15)C16—C11—S1119.83 (14)
C4—C3—C2119.07 (17)C12—C11—S1119.51 (15)
C4—C3—H3120.5C13—C12—C11119.63 (19)
C2—C3—H3120.5C13—C12—H12120.2
C3—C4—C5119.48 (17)C11—C12—H12120.2
C3—C4—C9120.64 (19)C12—C13—C14121.49 (18)
C5—C4—C9119.87 (18)C12—C13—H13119.3
C6—C5—C4122.87 (18)C14—C13—H13119.3
C6—C5—H5118.6C15—C14—C13117.8 (2)
C4—C5—H5118.6C15—C14—C17121.5 (2)
C5—C6—C7116.07 (18)C13—C14—C17120.7 (2)
C5—C6—H6122.0C14—C15—C16121.39 (19)
C7—C6—H6122.0C14—C15—H15119.3
O1—C7—C6125.98 (17)C16—C15—H15119.3
O1—C7—C2110.81 (16)C11—C16—C15119.12 (18)
C6—C7—C2123.22 (17)C11—C16—H16120.4
C1—C8—O1110.90 (15)C15—C16—H16120.4
C1—C8—C10133.2 (2)C14—C17—H17A109.5
O1—C8—C10115.87 (19)C14—C17—H17B109.5
C4—C9—H9A109.5H17A—C17—H17B109.5
C4—C9—H9B109.5C14—C17—H17C109.5
H9A—C9—H9B109.5H17A—C17—H17C109.5
C4—C9—H9C109.5H17B—C17—H17C109.5
O2—S1—C1—C8133.66 (16)C1—C2—C7—C6179.67 (15)
C11—S1—C1—C8115.81 (15)C2—C1—C8—O10.62 (18)
O2—S1—C1—C244.98 (18)S1—C1—C8—O1179.53 (11)
C11—S1—C1—C265.56 (16)C2—C1—C8—C10179.34 (18)
C8—C1—C2—C3178.81 (18)S1—C1—C8—C101.8 (3)
S1—C1—C2—C30.0 (3)C7—O1—C8—C10.57 (18)
C8—C1—C2—C70.41 (17)C7—O1—C8—C10179.54 (14)
S1—C1—C2—C7179.21 (13)O2—S1—C11—C164.03 (17)
C7—C2—C3—C40.3 (2)C1—S1—C11—C16115.99 (15)
C1—C2—C3—C4178.80 (17)O2—S1—C11—C12179.77 (14)
C2—C3—C4—C51.0 (2)C1—S1—C11—C1267.80 (15)
C2—C3—C4—C9177.99 (16)C16—C11—C12—C131.8 (3)
C3—C4—C5—C60.4 (3)S1—C11—C12—C13178.02 (15)
C9—C4—C5—C6178.59 (17)C11—C12—C13—C140.3 (3)
C4—C5—C6—C70.8 (3)C12—C13—C14—C151.3 (3)
C8—O1—C7—C6179.98 (16)C12—C13—C14—C17179.07 (18)
C8—O1—C7—C20.30 (17)C13—C14—C15—C161.5 (3)
C5—C6—C7—O1178.81 (15)C17—C14—C15—C16178.94 (19)
C5—C6—C7—C21.5 (3)C12—C11—C16—C151.7 (3)
C3—C2—C7—O1179.32 (13)S1—C11—C16—C15177.86 (14)
C1—C2—C7—O10.07 (17)C14—C15—C16—C110.0 (3)
C3—C2—C7—C60.9 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.952.603.334 (2)134
C17—H17B···O1ii0.982.523.387 (3)148
C10—H10B···Cgiii0.982.743.538 (3)139
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1, y+1, z+1/2; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H16O2S
Mr284.36
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)173
a, b, c (Å)13.072 (2), 6.1790 (11), 17.979 (3)
V3)1452.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.37 × 0.23 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.624, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
13920, 3587, 3101
Rint0.036
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.090, 1.03
No. of reflections3587
No. of parameters184
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.24
Absolute structureFlack (1983), 1729 Friedel pairs
Absolute structure parameter0.01 (7)

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
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.952.603.334 (2)134.4
C17—H17B···O1ii0.982.523.387 (3)148.0
C10—H10B···Cgiii0.982.743.538 (3)138.5
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1, y+1, z+1/2; (iii) x, y1, z.
 

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
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Volume 68| Part 5| May 2012| Page o1410
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