Related literature   {#sec1}
====================

For background information and the crystal structures of related compounds, see: Choi *et al.* (2010*a* [@bb3],*b* [@bb4]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~17~H~15~ClO~2~S*M* *~r~* = 318.80Triclinic,*a* = 6.043 (2) Å*b* = 11.716 (4) Å*c* = 12.217 (5) Åα = 117.99 (2)°β = 92.00 (2)°γ = 97.42 (2)°*V* = 752.9 (5) Å^3^*Z* = 2Mo *K*α radiationμ = 0.39 mm^−1^*T* = 173 K0.31 × 0.24 × 0.17 mm

### Data collection   {#sec2.1.2}

Bruker SMART APEXII CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2009[@bb2]) *T* ~min~ = 0.633, *T* ~max~ = 0.74612137 measured reflections3192 independent reflections2515 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.036

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.040*wR*(*F* ^2^) = 0.128*S* = 1.123192 reflections193 parametersH-atom parameters constrainedΔρ~max~ = 0.48 e Å^−3^Δρ~min~ = −0.55 e Å^−3^

 {#d5e469}

Data collection: *APEX2* (Bruker, 2009[@bb2]); cell refinement: *SAINT* (Bruker, 2009[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb6]); molecular graphics: *ORTEP-3* for Windows (Farrugia, 2012[@bb5]) and *DIAMOND* (Brandenburg, 1998[@bb1]); software used to prepare material for publication: *SHELXL97*.

Supplementary Material
======================

Crystal structure: contains datablock(s) I. DOI: [10.1107/S160053681302117X/pk2491sup1.cif](http://dx.doi.org/10.1107/S160053681302117X/pk2491sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S160053681302117X/pk2491Isup2.hkl](http://dx.doi.org/10.1107/S160053681302117X/pk2491Isup2.hkl)

###### 

Click here for additional data file.

Supplementary material file. DOI: [10.1107/S160053681302117X/pk2491Isup3.cml](http://dx.doi.org/10.1107/S160053681302117X/pk2491Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?pk2491&file=pk2491sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?pk2491sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?pk2491&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [PK2491](http://scripts.iucr.org/cgi-bin/sendsup?pk2491)).

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.

1. Comment
==========

As a part of our ongoing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (Choi *et al.*, 2010*a*) and 4-chlorophenylsulfinyl (Choi *et al.*, 2010*b*) substituents in 3-postion, 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 0.020 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-chlorophenyl ring is essentially planar, with a mean deviation of 0.011 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-chlorophenyl ring is 72.68 (6)°. In the crystal structure (Fig. 2), molecules are connected via pairs of C---H···π interactions into inversion dimers (Table 1, Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring). These dimers are further packed by C---H···O hydrogen bonds (Table 1) into supramolecular chains running along the *a*-axis direction. Additionally, the crystal packing (Fig. 2) also exhibits π--π interactions between the 4-chlorophenyl rings of adjacent molecules, with a Cg2···Cg2^iii^ distance of 4.094 (3) Å and an interplanar distance of 3.648 (3) Å resulting in a slippage of 1.656 (3) Å (Cg2 is the centroid of C12--C17 4-chlorophenyl ring).

2. Experimental {#experimental}
===============

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-2,4,7-trimethyl-1-benzofuran (333 mg, 1.1 mmol) in dichloromethane (40 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, 4:1 v/v) to afford the title compound as a colorless solid \[yield 66%, m.p. 432--433 K; *R*~f~ = 0.45 (hexane-ethyl acetate, 4:1 v/v)\]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

3. Refinement {#refinement}
=============

All H atoms were positioned geometrically and refined using a riding model, with C---H = 0.95 Å for aryl and 0.99 Å for methyl H atoms, respectively. *U*~iso~(H) = 1.2*U*~eq~(C) for aryl and 1.5*U*~eq~(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

Figures
=======

![The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.](e-69-o1383-fig1){#Fap1}

![A view of the C---H···O, C---H···π and π--π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. \[Symmetry codes: (i) x + 1, y, z; (ii) - x + 1, - y + 1, - z; (iii) - x + 1, - y, - z; (iv) x - 1, y, z.\]](e-69-o1383-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ---------------------- ---------------------------------------
  C~17~H~15~ClO~2~S      *Z* = 2
  *M~r~* = 318.80        *F*(000) = 332
  Triclinic, *P*1        *D*~x~ = 1.406 Mg m^−3^
  Hall symbol: -P 1      Melting point = 432--433 K
  *a* = 6.043 (2) Å      Mo *K*α radiation, λ = 0.71073 Å
  *b* = 11.716 (4) Å     Cell parameters from 4880 reflections
  *c* = 12.217 (5) Å     θ = 3.3--28.5°
  α = 117.99 (2)°        µ = 0.39 mm^−1^
  β = 92.00 (2)°         *T* = 173 K
  γ = 97.42 (2)°         Block, colourless
  *V* = 752.9 (5) Å^3^   0.31 × 0.24 × 0.17 mm
  ---------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART APEXII CCD diffractometer                       3192 independent reflections
  Radiation source: rotating anode                             2515 reflections with *I* \> 2σ(*I*)
  Graphite multilayer monochromator                            *R*~int~ = 0.036
  Detector resolution: 10.0 pixels mm^-1^                      θ~max~ = 27.0°, θ~min~ = 1.9°
  φ and ω scans                                                *h* = −7→7
  Absorption correction: multi-scan (*SADABS*; Bruker, 2009)   *k* = −14→14
  *T*~min~ = 0.633, *T*~max~ = 0.746                           *l* = −15→15
  12137 measured reflections                                   
  ------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- ------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.040   Hydrogen site location: difference Fourier map
  *wR*(*F*^2^) = 0.128                  H-atom parameters constrained
  *S* = 1.12                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0707*P*)^2^ + 0.168*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3192 reflections                      (Δ/σ)~max~ \< 0.001
  193 parameters                        Δρ~max~ = 0.48 e Å^−3^
  0 restraints                          Δρ~min~ = −0.55 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ \> 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------------- --------------- -------------------- --
         *x*            *y*            *z*             *U*~iso~\*/*U*~eq~   
  Cl1    0.57368 (11)   −0.03761 (6)   0.34385 (5)     0.0487 (2)           
  S1     0.33471 (8)    0.22715 (5)    0.02081 (5)     0.03169 (17)         
  O1     0.7881 (2)     0.53758 (12)   0.14079 (13)    0.0322 (3)           
  O2     0.0894 (2)     0.22965 (15)   0.02338 (16)    0.0456 (4)           
  C1     0.4952 (3)     0.38358 (17)   0.10912 (18)    0.0276 (4)           
  C2     0.5111 (3)     0.48591 (18)   0.23757 (18)    0.0294 (4)           
  C3     0.3881 (4)     0.5125 (2)     0.3376 (2)      0.0366 (5)           
  C4     0.4708 (5)     0.6281 (2)     0.4462 (2)      0.0471 (6)           
  H4     0.3926         0.6495         0.5176          0.057\*              
  C5     0.6598 (4)     0.7135 (2)     0.4561 (2)      0.0475 (6)           
  H5     0.7066         0.7902         0.5337          0.057\*              
  C6     0.7820 (4)     0.69163 (19)   0.3584 (2)      0.0392 (5)           
  C7     0.6962 (3)     0.57630 (18)   0.25069 (19)    0.0313 (4)           
  C8     0.6624 (3)     0.42057 (17)   0.05637 (18)    0.0290 (4)           
  C9     0.1778 (4)     0.4253 (2)     0.3290 (2)      0.0486 (6)           
  H9A    0.0852         0.3988         0.2509          0.073\*              
  H9B    0.0943         0.4726         0.3997          0.073\*              
  H9C    0.2157         0.3474         0.3308          0.073\*              
  C10    0.9885 (4)     0.7807 (2)     0.3643 (2)      0.0527 (7)           
  H10A   1.0121         0.8601         0.4455          0.079\*              
  H10B   0.9702         0.8046         0.2980          0.079\*              
  H10C   1.1185         0.7357         0.3530          0.079\*              
  C11    0.7331 (4)     0.36120 (19)   −0.06862 (19)   0.0343 (5)           
  H11A   0.8690         0.3239         −0.0681         0.051\*              
  H11B   0.7646         0.4281         −0.0952         0.051\*              
  H11C   0.6132         0.2917         −0.1266         0.051\*              
  C12    0.4109 (3)     0.15774 (17)   0.11811 (17)    0.0270 (4)           
  C13    0.6311 (3)     0.17380 (19)   0.1672 (2)      0.0323 (4)           
  H13    0.7474         0.2259         0.1523          0.039\*              
  C14    0.6813 (3)     0.1143 (2)     0.2374 (2)      0.0355 (5)           
  H14    0.8307         0.1269         0.2728          0.043\*              
  C15    0.5108 (4)     0.03655 (18)   0.25513 (18)    0.0319 (5)           
  C16    0.2927 (4)     0.01659 (19)   0.20341 (19)    0.0339 (5)           
  H16    0.1778         −0.0391        0.2147          0.041\*              
  C17    0.2428 (3)     0.07844 (19)   0.13485 (18)    0.0312 (4)           
  H17    0.0932         0.0660         0.0997          0.037\*              
  ------ -------------- -------------- --------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- --------------- -------------- -------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^         *U*^13^        *U*^23^
  Cl1   0.0644 (4)    0.0447 (3)    0.0454 (3)    0.0075 (3)      −0.0040 (3)    0.0294 (3)
  S1    0.0320 (3)    0.0291 (3)    0.0334 (3)    −0.00004 (19)   −0.0040 (2)    0.0162 (2)
  O1    0.0341 (8)    0.0262 (7)    0.0362 (8)    0.0016 (5)      0.0023 (6)     0.0159 (6)
  O2    0.0290 (8)    0.0526 (9)    0.0651 (11)   −0.0005 (7)     −0.0084 (7)    0.0389 (9)
  C1    0.0292 (10)   0.0255 (9)    0.0304 (10)   0.0061 (7)      0.0021 (8)     0.0151 (8)
  C2    0.0321 (10)   0.0272 (9)    0.0318 (10)   0.0088 (8)      0.0022 (8)     0.0158 (8)
  C3    0.0411 (12)   0.0387 (11)   0.0367 (11)   0.0166 (9)      0.0097 (9)     0.0207 (10)
  C4    0.0590 (15)   0.0478 (13)   0.0360 (12)   0.0222 (12)     0.0119 (11)    0.0174 (11)
  C5    0.0614 (16)   0.0332 (11)   0.0367 (13)   0.0129 (11)     −0.0026 (11)   0.0068 (10)
  C6    0.0451 (12)   0.0273 (10)   0.0405 (12)   0.0083 (9)      −0.0046 (10)   0.0124 (9)
  C7    0.0353 (11)   0.0271 (9)    0.0337 (11)   0.0086 (8)      0.0009 (9)     0.0156 (8)
  C8    0.0317 (10)   0.0249 (9)    0.0330 (10)   0.0050 (7)      −0.0008 (8)    0.0162 (8)
  C9    0.0490 (15)   0.0514 (14)   0.0506 (14)   0.0151 (11)     0.0204 (12)    0.0260 (12)
  C10   0.0501 (15)   0.0303 (11)   0.0598 (16)   −0.0017 (10)    −0.0098 (12)   0.0101 (11)
  C11   0.0395 (11)   0.0349 (10)   0.0353 (11)   0.0093 (9)      0.0076 (9)     0.0212 (9)
  C12   0.0284 (10)   0.0221 (8)    0.0277 (10)   0.0048 (7)      0.0019 (8)     0.0095 (8)
  C13   0.0253 (10)   0.0326 (10)   0.0403 (11)   0.0033 (8)      0.0054 (9)     0.0188 (9)
  C14   0.0291 (10)   0.0356 (10)   0.0423 (12)   0.0076 (8)      −0.0007 (9)    0.0187 (9)
  C15   0.0415 (12)   0.0267 (9)    0.0291 (10)   0.0089 (8)      0.0056 (9)     0.0137 (8)
  C16   0.0350 (11)   0.0300 (10)   0.0351 (11)   −0.0003 (8)     0.0047 (9)     0.0156 (9)
  C17   0.0273 (10)   0.0309 (10)   0.0331 (11)   0.0001 (8)      0.0014 (8)     0.0146 (9)
  ----- ------------- ------------- ------------- --------------- -------------- -------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  -------------------- -------------- ----------------------- --------------
  Cl1---C15            1.736 (2)      C9---H9A                0.9800
  S1---O2              1.4876 (16)    C9---H9B                0.9800
  S1---C1              1.754 (2)      C9---H9C                0.9800
  S1---C12             1.803 (2)      C10---H10A              0.9800
  O1---C7              1.365 (3)      C10---H10B              0.9800
  O1---C8              1.367 (2)      C10---H10C              0.9800
  C1---C8              1.348 (3)      C11---H11A              0.9800
  C1---C2              1.450 (3)      C11---H11B              0.9800
  C2---C3              1.382 (3)      C11---H11C              0.9800
  C2---C7              1.386 (3)      C12---C17               1.373 (3)
  C3---C4              1.392 (3)      C12---C13               1.393 (3)
  C3---C9              1.491 (3)      C13---C14               1.383 (3)
  C4---C5              1.379 (4)      C13---H13               0.9500
  C4---H4              0.9500         C14---C15               1.377 (3)
  C5---C6              1.363 (4)      C14---H14               0.9500
  C5---H5              0.9500         C15---C16               1.383 (3)
  C6---C7              1.389 (3)      C16---C17               1.388 (3)
  C6---C10             1.497 (3)      C16---H16               0.9500
  C8---C11             1.457 (3)      C17---H17               0.9500
                                                              
  O2---S1---C1         112.31 (9)     H9A---C9---H9C          109.5
  O2---S1---C12        106.67 (9)     H9B---C9---H9C          109.5
  C1---S1---C12        97.93 (9)      C6---C10---H10A         109.5
  C7---O1---C8         106.81 (16)    C6---C10---H10B         109.5
  C8---C1---C2         106.85 (17)    H10A---C10---H10B       109.5
  C8---C1---S1         117.84 (15)    C6---C10---H10C         109.5
  C2---C1---S1         134.94 (16)    H10A---C10---H10C       109.5
  C3---C2---C7         118.84 (19)    H10B---C10---H10C       109.5
  C3---C2---C1         136.4 (2)      C8---C11---H11A         109.5
  C7---C2---C1         104.69 (18)    C8---C11---H11B         109.5
  C2---C3---C4         115.3 (2)      H11A---C11---H11B       109.5
  C2---C3---C9         122.4 (2)      C8---C11---H11C         109.5
  C4---C3---C9         122.2 (2)      H11A---C11---H11C       109.5
  C5---C4---C3         123.8 (2)      H11B---C11---H11C       109.5
  C5---C4---H4         118.1          C17---C12---C13         120.27 (18)
  C3---C4---H4         118.1          C17---C12---S1          116.75 (15)
  C6---C5---C4         122.3 (2)      C13---C12---S1          122.80 (16)
  C6---C5---H5         118.9          C14---C13---C12         120.40 (19)
  C4---C5---H5         118.9          C14---C13---H13         119.8
  C5---C6---C7         113.1 (2)      C12---C13---H13         119.8
  C5---C6---C10        124.5 (2)      C15---C14---C13         118.78 (19)
  C7---C6---C10        122.4 (2)      C15---C14---H14         120.6
  O1---C7---C2         110.62 (17)    C13---C14---H14         120.6
  O1---C7---C6         122.9 (2)      C14---C15---C16         121.26 (19)
  C2---C7---C6         126.5 (2)      C14---C15---Cl1         118.78 (16)
  C1---C8---O1         111.01 (18)    C16---C15---Cl1         119.97 (17)
  C1---C8---C11        133.18 (18)    C15---C16---C17         119.65 (19)
  O1---C8---C11        115.80 (18)    C15---C16---H16         120.2
  C3---C9---H9A        109.5          C17---C16---H16         120.2
  C3---C9---H9B        109.5          C12---C17---C16         119.60 (18)
  H9A---C9---H9B       109.5          C12---C17---H17         120.2
  C3---C9---H9C        109.5          C16---C17---H17         120.2
                                                              
  O2---S1---C1---C8    −132.20 (15)   C10---C6---C7---O1      −2.5 (3)
  C12---S1---C1---C8   116.06 (16)    C5---C6---C7---C2       −2.0 (3)
  O2---S1---C1---C2    55.9 (2)       C10---C6---C7---C2      177.73 (19)
  C12---S1---C1---C2   −55.8 (2)      C2---C1---C8---O1       1.1 (2)
  C8---C1---C2---C3    175.4 (2)      S1---C1---C8---O1       −172.94 (12)
  S1---C1---C2---C3    −12.0 (4)      C2---C1---C8---C11      −179.51 (19)
  C8---C1---C2---C7    −1.4 (2)       S1---C1---C8---C11      6.5 (3)
  S1---C1---C2---C7    171.16 (16)    C7---O1---C8---C1       −0.4 (2)
  C7---C2---C3---C4    −2.7 (3)       C7---O1---C8---C11      −179.88 (15)
  C1---C2---C3---C4    −179.2 (2)     O2---S1---C12---C17     23.92 (17)
  C7---C2---C3---C9    175.67 (19)    C1---S1---C12---C17     140.15 (16)
  C1---C2---C3---C9    −0.8 (4)       O2---S1---C12---C13     −160.93 (16)
  C2---C3---C4---C5    0.9 (3)        C1---S1---C12---C13     −44.70 (18)
  C9---C3---C4---C5    −177.5 (2)     C17---C12---C13---C14   −2.6 (3)
  C3---C4---C5---C6    0.5 (4)        S1---C12---C13---C14    −177.56 (15)
  C4---C5---C6---C7    −0.1 (3)       C12---C13---C14---C15   1.6 (3)
  C4---C5---C6---C10   −179.8 (2)     C13---C14---C15---C16   0.5 (3)
  C8---O1---C7---C2    −0.6 (2)       C13---C14---C15---Cl1   −179.75 (15)
  C8---O1---C7---C6    179.63 (17)    C14---C15---C16---C17   −1.6 (3)
  C3---C2---C7---O1    −176.29 (16)   Cl1---C15---C16---C17   178.62 (15)
  C1---C2---C7---O1    1.2 (2)        C13---C12---C17---C16   1.4 (3)
  C3---C2---C7---C6    3.5 (3)        S1---C12---C17---C16    176.70 (15)
  C1---C2---C7---C6    −179.02 (18)   C15---C16---C17---C12   0.6 (3)
  C5---C6---C7---O1    177.81 (18)                            
  -------------------- -------------- ----------------------- --------------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring.

  -------------------------- --------- --------- ----------- ---------------
  *D*---H···*A*              *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C11---H11*A*···O2^i^       0.98      2.38      3.254 (3)   148
  C11---H11*B*···*Cg*1^ii^   0.98      2.96      3.503 (3)   116
  -------------------------- --------- --------- ----------- ---------------

Symmetry codes: (i) *x*+1, *y*, *z*; (ii) −*x*+1, −*y*+1, −*z*.

###### Hydrogen-bond geometry (Å, °)

*Cg*1 is the centroid of the C1/C2/C7/O1/C8 furan ring.

  *D*---H⋯*A*              *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------------ --------- ------- ----------- -------------
  C11---H11*A*⋯O2^i^       0.98      2.38    3.254 (3)   148
  C11---H11*B*⋯*Cg*1^ii^   0.98      2.96    3.503 (3)   116

Symmetry codes: (i) ; (ii) .
