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

For bond-length data, see: Allen *et al.* (1987[@bb1]). For background to non-linear optical materials research, see: Koshima & Matsuura (1998[@bb9]); Prasad & Williams (1991[@bb10]); Wenseleers *et al.* (1998[@bb13]). For related structures, see: Chanawanno *et al.* (2008[@bb3]); Chantrapromma *et al.* (2007[@bb7], 2008[@bb5]); Chantrapromma, Chanawanno & Fun (2009[@bb4]); Chantrapromma, Jansrisewangwong *et al.* (2009[@bb6]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[@bb8]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~14~H~13~ClN^+^·C~6~H~4~ClO~3~S^−^*M* *~r~* = 422.32Monoclinic,*a* = 7.9018 (7) Å*b* = 18.5102 (17) Å*c* = 12.6818 (12) Åβ = 93.942 (7)°*V* = 1850.5 (3) Å^3^*Z* = 4Mo *K*α radiationμ = 0.49 mm^−1^*T* = 100 K0.19 × 0.17 × 0.09 mm

### Data collection {#sec2.1.2}

Bruker APEXII CCD area-detector diffractometerAbsorption correction: multi-scan (**SADABS**; Bruker, 2005[@bb2]) *T* ~min~ = 0.913, *T* ~max~ = 0.95919968 measured reflections4249 independent reflections2426 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.123

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.085*wR*(*F* ^2^) = 0.215*S* = 1.054249 reflections245 parametersH-atom parameters constrainedΔρ~max~ = 0.82 e Å^−3^Δρ~min~ = −0.58 e Å^−3^

 {#d5e647}

Data collection: *APEX2* (Bruker, 2005[@bb2]); cell refinement: *SAINT* (Bruker, 2005[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb11]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL* nd *PLATON* (Spek, 2009[@bb12]).

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536809021667/is2430sup1.cif](http://dx.doi.org/10.1107/S1600536809021667/is2430sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809021667/is2430Isup2.hkl](http://dx.doi.org/10.1107/S1600536809021667/is2430Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?is2430&file=is2430sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?is2430sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?is2430&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [IS2430](http://scripts.iucr.org/cgi-bin/sendsup?is2430)).

KC thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. Partial financial support from the Graduate School, Prince of Songkla University is gratefully acknowledged. The authors also thank the Prince of Songkla University for financial support through the Crystal Materials Research Unit and the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

Comment
=======

To search for new materials capable for nonlinear optical (NLO) applications, many studies have focused on organic molecules containing highly polarizable π-conjugated backbones (Wenseleers *et al.*, 1998). For second order NLO compounds, an electron donor and an acceptor group are attached to both ends of this backbone to create an asymmetric \"push-pull\" system (Prasad & Williams, 1991). In addition, due to the inherently second-order NLO character of noncentrosymmetric organic compounds, the x-ray structure determination is a very important method to determine their NLO properties (Koshima & Matsuura, 1998). During the course of our exploring for new organic NLO materials, we have previously synthesized and reported a number of the crystal structures of pyridinium derivatives (Chanawanno *et al.*, 2008; Chantrapromma *et al.*, 2007, 2008; Chantrapromma, Chanawanno & Fun, 2009; Chantrapromma, Jansrisewangwong *et al.*, 2009). The title compound (I) has been synthesized and its crystal structure was undertaken in order to establish the conformation of the various groups and its crystal packing. The title compound crystallized in centrosymmetric space group *P*2~1~/*c* which precluded the second-order nonlinear optical properties.

In the molecule of the title compound, C~14~H~13~ClN^+^.C~6~H~4~ClO~3~S^-^ (Fig. 1), the cation exists in an *E* configuration with respect to the C6═C7 double bond \[1.339 (7) Å\] and the torsion angle of C5---C6---C7---C8 = 178.2 (4)°. The cation is almost planar with the dihedral angle between the pyridinium and benzene rings of the cation being 3.4 (2)°. The orientation of the anion is perpendicular with respect to the cation which is reflected by the dihedral angles between the benzene ring of the anion and the pyridinium and benzene rings of the cation being 89.4 (2)° and 89.9 (2)°. The Cl^-^ ions are coplanar with the attached benzene rings. The bond distances in both cation and anion have normal values (Allen *et al.*, 1987) and comparable with the closely related compounds (Chanawanno *et al.*, 2008; Chantrapromma *et al.*, 2007, 2008; Chantrapromma, Chanawanno & Fun, 2009; Chantrapromma, Jansrisewangwong *et al.*, 2009).

In the crystal packing (Fig. 2), all O atoms of the sulfonate group are involved in weak C---H···O interactions (Table 1). The cations and anions are individually arranged alternatively with the cations being linked into chains along the *c* axis by C---H···Cl weak interaction (Table 1). The anions are linked to the adjacent cations chains by C---H···O and C---H···Cl weak interactions forming a 2D network parallel to the *bc* plane. The crystal structure is further stabilized by C---H···π interactions (Table 1). A π--π interaction is also observed with the Cg~1~···Cg~2~ distance of 3.668 (3) Å (symmetry code: -x, 1-y, 1-z); Cg~1~, Cg~2~ and Cg~3~ are the centroids of C1--C5/N1, C8--C13 and C15--C20, respectively.

Experimental {#experimental}
============

2-\[(*E*)-2-(4-Chlorophenyl)ethenyl\]-1-methylpyridinium iodide (0.24 g, 0.67 mmol) which was prepared according to the previous report (Chanawanno *et al.*, 2008) was mixed (1:1 molar ratio) with silver(I) 4-chlorobenzenesulfonate (0.20 g, 0.67 mmol) (Chantrapromma *et al.*, 2007) in methanol solution (100 ml). The mixture solution was stirred for 30 min, the precipitate of silver iodide which formed was filtered and the filtrate was evaporated to give the title compound as an orange solid. Orange needle-shaped single crystals of the title compound suitable for *x*-ray structure determination were recrystallized from methanol by slow evaporation at room temperature over a few weeks (m.p. 485-487 K).

Refinement {#refinement}
==========

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C-H) = 0.93 Å for aromatic and CH and 0.96 Å for CH~3~ atoms. The *U*~iso~ values were constrained to be 1.5*U*~eq~ of the carrier atom for methyl H atoms and 1.2*U*~eq~ for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.91 Å from Cl1 and the deepest hole is located at 0.91 Å from S1.

Figures
=======

![The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.](e-65-o1554-fig1){#Fap1}

![The crystal packing of the title compound viewed down the a axis. Weak C---H···O and C---H···Cl interactions are shown as dashed lines.](e-65-o1554-fig2){#Fap2}

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

  ------------------------------------- ---------------------------------------
  C~14~H~13~ClN^+^·C~6~H~4~ClO~3~S^−^   *F*(000) = 872
  *M~r~* = 422.32                       *D*~x~ = 1.516 Mg m^−3^
  Monoclinic, *P*2~1~/*c*               Melting point = 485--487 K
  Hall symbol: -P 2ybc                  Mo *K*α radiation, λ = 0.71073 Å
  *a* = 7.9018 (7) Å                    Cell parameters from 4249 reflections
  *b* = 18.5102 (17) Å                  θ = 2.0--27.5°
  *c* = 12.6818 (12) Å                  µ = 0.49 mm^−1^
  β = 93.942 (7)°                       *T* = 100 K
  *V* = 1850.5 (3) Å^3^                 Needle, orange
  *Z* = 4                               0.19 × 0.17 × 0.09 mm
  ------------------------------------- ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker APEXII CCD area-detector diffractometer               4249 independent reflections
  Radiation source: sealed tube                                2426 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.123
  φ and ω scans                                                θ~max~ = 27.5°, θ~min~ = 2.0°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2005)   *h* = −10→10
  *T*~min~ = 0.913, *T*~max~ = 0.959                           *k* = −24→23
  19968 measured reflections                                   *l* = −15→16
  ------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.085   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.215                  H-atom parameters constrained
  *S* = 1.05                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0922*P*)^2^ + 0.5785*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4249 reflections                      (Δ/σ)~max~ = 0.001
  245 parameters                        Δρ~max~ = 0.82 e Å^−3^
  0 restraints                          Δρ~min~ = −0.58 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

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

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
  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~   
  S1     0.14744 (15)   0.73096 (6)    0.57427 (10)   0.0223 (3)           
  Cl1    0.60079 (17)   0.44645 (8)    0.83430 (11)   0.0374 (4)           
  Cl2    0.76914 (16)   0.68816 (7)    0.90585 (10)   0.0315 (4)           
  N1     −0.0338 (5)    0.5768 (2)     0.2267 (3)     0.0242 (9)           
  O1     0.1460 (4)     0.80779 (17)   0.5473 (3)     0.0273 (8)           
  O2     −0.0022 (4)    0.70865 (18)   0.6258 (3)     0.0273 (8)           
  O3     0.1871 (4)     0.68462 (18)   0.4870 (3)     0.0300 (9)           
  C1     −0.1248 (6)    0.5785 (3)     0.1326 (4)     0.0295 (12)          
  H1A    −0.1595        0.6228         0.1040         0.035\*              
  C2     −0.1670 (6)    0.5162 (3)     0.0788 (4)     0.0306 (12)          
  H2A    −0.2302        0.5180         0.0142         0.037\*              
  C3     −0.1146 (6)    0.4514 (3)     0.1215 (4)     0.0306 (13)          
  H3A    −0.1406        0.4087         0.0852         0.037\*              
  C4     −0.0239 (6)    0.4492 (3)     0.2176 (4)     0.0312 (13)          
  H4A    0.0093         0.4048         0.2464         0.037\*              
  C5     0.0196 (6)     0.5129 (3)     0.2734 (4)     0.0283 (12)          
  C6     0.1196 (6)     0.5163 (3)     0.3718 (4)     0.0296 (12)          
  H6A    0.1531         0.5615         0.3979         0.035\*              
  C7     0.1672 (6)     0.4577 (3)     0.4281 (4)     0.0309 (13)          
  H7A    0.1299         0.4131         0.4018         0.037\*              
  C8     0.2740 (6)     0.4578 (3)     0.5282 (4)     0.0256 (12)          
  C9     0.3296 (6)     0.3914 (3)     0.5712 (4)     0.0292 (12)          
  H9A    0.2971         0.3487         0.5368         0.035\*              
  C10    0.4323 (6)     0.3886 (3)     0.6639 (4)     0.0314 (13)          
  H10A   0.4709         0.3444         0.6909         0.038\*              
  C11    0.4766 (6)     0.4515 (3)     0.7157 (4)     0.0246 (11)          
  C12    0.4242 (6)     0.5184 (3)     0.6760 (4)     0.0271 (12)          
  H12A   0.4562         0.5607         0.7116         0.032\*              
  C13    0.3237 (6)     0.5208 (3)     0.5825 (4)     0.0268 (12)          
  H13A   0.2885         0.5654         0.5551         0.032\*              
  C14    0.0109 (6)     0.6469 (3)     0.2776 (4)     0.0296 (12)          
  H14A   −0.0401        0.6855         0.2360         0.044\*              
  H14B   0.1319         0.6527         0.2828         0.044\*              
  H14C   −0.0301        0.6480         0.3471         0.044\*              
  C15    0.3208 (6)     0.7181 (2)     0.6698 (4)     0.0217 (11)          
  C16    0.2956 (6)     0.7066 (2)     0.7776 (4)     0.0229 (11)          
  H16A   0.1862         0.7062         0.8004         0.027\*              
  C17    0.4327 (6)     0.6958 (2)     0.8495 (4)     0.0248 (11)          
  H17A   0.4160         0.6872         0.9203         0.030\*              
  C18    0.5940 (6)     0.6977 (2)     0.8154 (4)     0.0248 (11)          
  C19    0.6226 (6)     0.7092 (3)     0.7092 (4)     0.0242 (11)          
  H19A   0.7322         0.7099         0.6867         0.029\*              
  C20    0.4844 (6)     0.7192 (2)     0.6385 (4)     0.0231 (11)          
  H20A   0.5020         0.7270         0.5676         0.028\*              
  ------ -------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------ -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^      *U*^12^        *U*^13^        *U*^23^
  S1    0.0271 (6)    0.0151 (7)    0.0242 (7)   0.0003 (5)     −0.0022 (5)    −0.0002 (5)
  Cl1   0.0445 (8)    0.0359 (9)    0.0306 (8)   −0.0021 (6)    −0.0061 (6)    0.0026 (6)
  Cl2   0.0339 (7)    0.0273 (7)    0.0317 (8)   0.0026 (5)     −0.0097 (6)    −0.0012 (6)
  N1    0.029 (2)     0.021 (2)     0.023 (2)    −0.0022 (18)   0.0003 (19)    −0.0006 (18)
  O1    0.0359 (19)   0.0165 (19)   0.028 (2)    0.0014 (15)    −0.0052 (16)   0.0039 (15)
  O2    0.0245 (17)   0.023 (2)     0.033 (2)    −0.0006 (14)   −0.0059 (15)   0.0014 (16)
  O3    0.041 (2)     0.023 (2)     0.025 (2)    0.0034 (16)    −0.0047 (16)   −0.0076 (15)
  C1    0.033 (3)     0.033 (3)     0.022 (3)    0.000 (2)      0.003 (2)      0.003 (2)
  C2    0.039 (3)     0.033 (3)     0.020 (3)    −0.006 (2)     0.004 (2)      −0.004 (2)
  C3    0.039 (3)     0.029 (3)     0.025 (3)    −0.012 (2)     0.008 (2)      −0.003 (2)
  C4    0.038 (3)     0.015 (3)     0.041 (3)    −0.003 (2)     0.006 (3)      0.000 (2)
  C5    0.024 (3)     0.029 (3)     0.033 (3)    0.000 (2)      0.003 (2)      0.003 (2)
  C6    0.037 (3)     0.017 (3)     0.034 (3)    −0.004 (2)     −0.001 (3)     −0.002 (2)
  C7    0.035 (3)     0.021 (3)     0.036 (3)    0.000 (2)      0.002 (3)      −0.004 (2)
  C8    0.025 (3)     0.024 (3)     0.028 (3)    −0.001 (2)     −0.003 (2)     0.001 (2)
  C9    0.040 (3)     0.018 (3)     0.030 (3)    −0.001 (2)     0.002 (2)      −0.002 (2)
  C10   0.038 (3)     0.020 (3)     0.036 (3)    0.002 (2)      −0.002 (3)     0.006 (2)
  C11   0.031 (3)     0.023 (3)     0.020 (3)    0.001 (2)      0.000 (2)      0.001 (2)
  C12   0.030 (3)     0.020 (3)     0.032 (3)    −0.005 (2)     0.003 (2)      −0.004 (2)
  C13   0.031 (3)     0.016 (3)     0.033 (3)    0.000 (2)      −0.002 (2)     0.002 (2)
  C14   0.043 (3)     0.017 (3)     0.029 (3)    −0.005 (2)     0.001 (2)      −0.001 (2)
  C15   0.028 (3)     0.015 (3)     0.021 (3)    −0.001 (2)     0.000 (2)      −0.005 (2)
  C16   0.030 (3)     0.010 (2)     0.029 (3)    0.0008 (19)    0.004 (2)      −0.002 (2)
  C17   0.037 (3)     0.014 (3)     0.022 (3)    0.002 (2)      −0.007 (2)     −0.001 (2)
  C18   0.030 (3)     0.011 (3)     0.032 (3)    0.001 (2)      −0.005 (2)     −0.002 (2)
  C19   0.022 (2)     0.023 (3)     0.027 (3)    0.000 (2)      −0.001 (2)     −0.002 (2)
  C20   0.029 (3)     0.019 (3)     0.021 (3)    −0.004 (2)     0.000 (2)      −0.002 (2)
  ----- ------------- ------------- ------------ -------------- -------------- --------------

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

  ---------------------- ------------ ----------------------- ------------
  S1---O2                1.450 (3)    C8---C9                 1.402 (7)
  S1---O3                1.451 (3)    C9---C10                1.383 (7)
  S1---O1                1.462 (3)    C9---H9A                0.9300
  S1---C15               1.781 (5)    C10---C11               1.370 (7)
  Cl1---C11              1.741 (5)    C10---H10A              0.9300
  Cl2---C18              1.745 (5)    C11---C12               1.389 (7)
  N1---C1                1.350 (6)    C12---C13               1.382 (7)
  N1---C5                1.375 (6)    C12---H12A              0.9300
  N1---C14               1.482 (6)    C13---H13A              0.9300
  C1---C2                1.369 (7)    C14---H14A              0.9600
  C1---H1A               0.9300       C14---H14B              0.9600
  C2---C3                1.370 (7)    C14---H14C              0.9600
  C2---H2A               0.9300       C15---C20               1.379 (6)
  C3---C4                1.372 (7)    C15---C16               1.411 (6)
  C3---H3A               0.9300       C16---C17               1.382 (7)
  C4---C5                1.406 (7)    C16---H16A              0.9300
  C4---H4A               0.9300       C17---C18               1.374 (7)
  C5---C6                1.432 (7)    C17---H17A              0.9300
  C6---C7                1.339 (7)    C18---C19               1.398 (7)
  C6---H6A               0.9300       C19---C20               1.377 (6)
  C7---C8                1.475 (7)    C19---H19A              0.9300
  C7---H7A               0.9300       C20---H20A              0.9300
  C8---C13               1.397 (7)                            
                                                              
  O2---S1---O3           113.6 (2)    C11---C10---C9          119.4 (5)
  O2---S1---O1           112.9 (2)    C11---C10---H10A        120.3
  O3---S1---O1           113.3 (2)    C9---C10---H10A         120.3
  O2---S1---C15          105.5 (2)    C10---C11---C12         121.5 (5)
  O3---S1---C15          104.1 (2)    C10---C11---Cl1         118.6 (4)
  O1---S1---C15          106.4 (2)    C12---C11---Cl1         119.8 (4)
  C1---N1---C5           122.0 (4)    C13---C12---C11         118.7 (5)
  C1---N1---C14          117.4 (4)    C13---C12---H12A        120.7
  C5---N1---C14          120.5 (4)    C11---C12---H12A        120.7
  N1---C1---C2           121.1 (5)    C12---C13---C8          121.4 (5)
  N1---C1---H1A          119.4        C12---C13---H13A        119.3
  C2---C1---H1A          119.4        C8---C13---H13A         119.3
  C1---C2---C3           119.0 (5)    N1---C14---H14A         109.5
  C1---C2---H2A          120.5        N1---C14---H14B         109.5
  C3---C2---H2A          120.5        H14A---C14---H14B       109.5
  C2---C3---C4           120.2 (5)    N1---C14---H14C         109.5
  C2---C3---H3A          119.9        H14A---C14---H14C       109.5
  C4---C3---H3A          119.9        H14B---C14---H14C       109.5
  C3---C4---C5           121.2 (5)    C20---C15---C16         118.6 (4)
  C3---C4---H4A          119.4        C20---C15---S1          119.6 (4)
  C5---C4---H4A          119.4        C16---C15---S1          121.8 (4)
  N1---C5---C4           116.6 (5)    C17---C16---C15         120.3 (4)
  N1---C5---C6           118.2 (4)    C17---C16---H16A        119.8
  C4---C5---C6           125.2 (5)    C15---C16---H16A        119.8
  C7---C6---C5           123.1 (5)    C18---C17---C16         119.4 (5)
  C7---C6---H6A          118.4        C18---C17---H17A        120.3
  C5---C6---H6A          118.4        C16---C17---H17A        120.3
  C6---C7---C8           125.5 (5)    C17---C18---C19         121.5 (4)
  C6---C7---H7A          117.2        C17---C18---Cl2         120.1 (4)
  C8---C7---H7A          117.2        C19---C18---Cl2         118.4 (4)
  C13---C8---C9          118.1 (5)    C20---C19---C18         118.3 (4)
  C13---C8---C7          123.3 (5)    C20---C19---H19A        120.8
  C9---C8---C7           118.6 (5)    C18---C19---H19A        120.8
  C10---C9---C8          120.9 (5)    C19---C20---C15         121.9 (4)
  C10---C9---H9A         119.6        C19---C20---H20A        119.1
  C8---C9---H9A          119.6        C15---C20---H20A        119.1
                                                              
  C5---N1---C1---C2      −0.6 (7)     C10---C11---C12---C13   0.6 (7)
  C14---N1---C1---C2     178.0 (4)    Cl1---C11---C12---C13   −179.1 (4)
  N1---C1---C2---C3      −0.3 (7)     C11---C12---C13---C8    0.3 (7)
  C1---C2---C3---C4      1.1 (7)      C9---C8---C13---C12     −0.3 (7)
  C2---C3---C4---C5      −1.1 (7)     C7---C8---C13---C12     −179.8 (4)
  C1---N1---C5---C4      0.6 (6)      O2---S1---C15---C20     165.8 (4)
  C14---N1---C5---C4     −177.9 (4)   O3---S1---C15---C20     45.9 (4)
  C1---N1---C5---C6      178.3 (4)    O1---S1---C15---C20     −74.1 (4)
  C14---N1---C5---C6     −0.3 (6)     O2---S1---C15---C16     −14.1 (4)
  C3---C4---C5---N1      0.2 (7)      O3---S1---C15---C16     −134.0 (4)
  C3---C4---C5---C6      −177.3 (5)   O1---S1---C15---C16     106.0 (4)
  N1---C5---C6---C7      174.7 (5)    C20---C15---C16---C17   −0.8 (7)
  C4---C5---C6---C7      −7.9 (8)     S1---C15---C16---C17    179.1 (4)
  C5---C6---C7---C8      178.2 (4)    C15---C16---C17---C18   1.2 (7)
  C6---C7---C8---C13     7.1 (8)      C16---C17---C18---C19   −1.1 (7)
  C6---C7---C8---C9      −172.5 (5)   C16---C17---C18---Cl2   177.2 (4)
  C13---C8---C9---C10    −0.7 (7)     C17---C18---C19---C20   0.6 (7)
  C7---C8---C9---C10     178.9 (4)    Cl2---C18---C19---C20   −177.7 (4)
  C8---C9---C10---C11    1.6 (7)      C18---C19---C20---C15   −0.2 (7)
  C9---C10---C11---C12   −1.6 (7)     C16---C15---C20---C19   0.3 (7)
  C9---C10---C11---Cl1   178.2 (4)    S1---C15---C20---C19    −179.6 (4)
  ---------------------- ------------ ----------------------- ------------

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

  ---------------------- --------- --------- ----------- ---------------
  *D*---H···*A*          *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C1---H1A···Cl2^i^      0.93      2.81      3.572 (5)   140
  C3---H3A···O1^ii^      0.93      2.51      3.411 (6)   163
  C6---H6A···O3          0.93      2.55      3.467 (6)   168
  C7---H7A···O2^iii^     0.93      2.48      3.395 (6)   166
  C13---H13A···O3        0.93      2.48      3.413 (6)   178
  C14---H14A···O2^iv^    0.96      2.44      3.292 (6)   148
  C14---H14C···O3        0.96      2.48      2.995 (6)   114
  C16---H16A···O2        0.93      2.58      2.936 (6)   103
  C19---H19A···O2^v^     0.93      2.29      3.216 (6)   178
  C10---H10A···Cg3^vi^   0.93      2.71      3.632 (6)   172
  C12---H12A···Cg3       0.93      2.75      3.614 (6)   154
  ---------------------- --------- --------- ----------- ---------------

Symmetry codes: (i) *x*−1, *y*, *z*−1; (ii) −*x*, *y*−1/2, −*z*+1/2; (iii) −*x*, −*y*+1, −*z*+1; (iv) *x*, −*y*+3/2, *z*−1/2; (v) *x*+1, *y*, *z*; (vi) −*x*+1, *y*−1/2, −*z*+3/2.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*              *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------------ --------- ------- ----------- -------------
  C1---H1*A*⋯Cl2^i^        0.93      2.81    3.572 (5)   140
  C3---H3*A*⋯O1^ii^        0.93      2.51    3.411 (6)   163
  C6---H6*A*⋯O3            0.93      2.55    3.467 (6)   168
  C7---H7*A*⋯O2^iii^       0.93      2.48    3.395 (6)   166
  C13---H13*A*⋯O3          0.93      2.48    3.413 (6)   178
  C14---H14*A*⋯O2^iv^      0.96      2.44    3.292 (6)   148
  C14---H14*C*⋯O3          0.96      2.48    2.995 (6)   114
  C16---H16*A*⋯O2          0.93      2.58    2.936 (6)   103
  C19---H19*A*⋯O2^v^       0.93      2.29    3.216 (6)   178
  C10---H10*A*⋯*Cg*3^vi^   0.93      2.71    3.632 (6)   172
  C12---H12*A*⋯*Cg*3       0.93      2.75    3.614 (6)   154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . *Cg*3 is the centroid of the C15--C20 ring.

[^1]: Thomson Reuters ResearcherID: A-3561-2009.

[^2]: Additional correspondence author, e-mail: suchada.c\@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.
