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

For bond-length data, see: Allen *et al.* ( 1987[@bb1]).  For details of hydrogen-bond motifs, see: Bernstein *et al.* ( 1995[@bb2]).  For related structures, see for example: Chantrapromma *et al.* ( 2006*a* [@bb7],*b* [@bb4]; 2007*a* [@bb5],*b* [@bb8],*c* [@bb6]); Fun *et al.* ( 2006[@bb9]); Glavcheva *et al.* ( 2004[@bb10]); Jindawong *et al.* ( 2005[@bb11]).  For background to non-linear optics, see for example: Oudar & Chemla (1977[@bb12]); Williams (1984[@bb15]). 

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

(C~19~H~18~NO~2~)~2~\[ZnI~4~\]·CH~4~O*M* *~r~* = 1189.72Monoclinic,*a* = 8.6449 (1) Å*b* = 23.4312 (4) Å*c* = 19.7763 (3) Åβ = 91.724 (1)°*V* = 4004.08 (10) Å^3^*Z* = 4Mo *K*α radiationμ = 3.74 mm^−1^*T* = 100.0 (1) K0.43 × 0.28 × 0.13 mm

### Data collection {#sec2.1.2}

Bruker SMART APEX2 CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2005[@bb3]) *T* ~min~ = 0.295, *T* ~max~ = 0.646100181 measured reflections18959 independent reflections15305 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.033

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.035*wR*(*F* ^2^) = 0.091*S* = 1.1018959 reflections465 parametersH-atom parameters constrainedΔρ~max~ = 4.98 e Å^−3^Δρ~min~ = −1.46 e Å^−3^

 {#d5e640}

Data collection: *APEX2* (Bruker, 2005[@bb3]); cell refinement: *APEX2*; data reduction: *SAINT* (Bruker, 2005[@bb3]); program(s) used to solve structure: *SHELXTL* (Sheldrick, 1998[@bb13]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL* and *PLATON* (Spek, 2003[@bb14]). 

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536807064215/sj2450sup1.cif](http://dx.doi.org/10.1107/S1600536807064215/sj2450sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536807064215/sj2450Isup2.hkl](http://dx.doi.org/10.1107/S1600536807064215/sj2450Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?sj2450&file=sj2450sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?sj2450sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?sj2450&checkcif=yes)

This paper is dedicated to His Majesty, Thai King Bhumibol Adulyadej on the occasion of his 80th Birthday Anniversary which fell on December 5th, 2007. 

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [SJ2450](http://scripts.iucr.org/cgi-bin/sendsup?sj2450)). 

The authors thank Prince of Songkla University for a research grant.  The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Scientific Advancement Grant Allocation (SAGA) grant No.  304/PFIZIK/653003/A118.  KC thanks the Development and Promotion of Science and Technology Talents Project for a study grant.  PR thanks the Graduate School, Prince of Songkla University. 

Comment
=======

There is considerable interest in the synthesis of new materials with large second-order nonlinear properties because of their potential usage in a varity of applications such as in optical data storage, optical information processing and telecommunication.  We have previously reported the structures of several quinolinium salts (Chantrapromma *et al.*,  2006*a*,*b*, 2007*a*,*b*,*c*; Fun *et al.*,  2006; Jindawong *et al.*,  2005), which were synthesized to study their nonlinear optical (NLO) properties.  At the molecular level, a generally popular approach towards NLO materials is to design and systhesize compounds with extended conjugated π systems with donor and acceptor groups because such compounds are likely to exhibit large values of molecular hyperpolarizability (β) and to possess polarizable electrons (as in a conjugated π system) spread over a large distance (Oudar & Chemla, 1977).  Quinolinium derivatives are considered to be good conjugated π systems.  Organic--inorganic hybrid complexes also present a promising new type of materials for various applications.  Thus, we extended our synthesis to this class of materials.  This single-crystal X-ray structural study of the title compound was carried out in order to obtain detailed information about its crystal structure.  However, the title compound crystallized in the centrosymmetric monoclinic space group *P*2~1~/*c* and therefore does not exhibit nonlinear optical properties (Williams, 1984). 

The asymmetric unit of the title compound consists of two C~19~H~18~NO~2~^+^ cations, a ZnI~4~^2-^ anion and a methanol solvate molecule (Fig.  1).  Each cation is nearly planar as indicated by the dihedral angle between the quinolinium planes and the benzene rings in each cation being 1.78 (10) and 5.44 (10)°, respectively.  The H atoms attached to the alkene C atoms C10 and C11 and C29 and C30 are mutually *trans*; torsion angles C9---C10---C11---C12 = 179.1 (2)° and C28---C29---C30---C31 = -179.3 (2)°.  Both the hydroxy and methoxy groups are reasonably coplanar with the benzene rings to which they are attached with torsion angles C19---O2---C15---C16 = -0.4 (4)° and C38---O4---C34---C35 = 1.2 (4)°.  Both cations form intramolecular O---H···O hydrogen bonds between the hydroxy and methoxy groups which generate S(5) ring motifs (Bernstein *et al.*,  1995).  The two cations are approximately parallel to one another with dihedral angles 7.55 (7)° between the two quinolinium planes (C1--C9/N1 and C20--C28/N2) and 12.82 (12)° between the two benzene rings (C12--C17 and C31--C36).  The ZnI~4~^2-^ anion shows only small distortions from a regular tetrahedron as was found previously (Glavcheva *et al.*,  2004).  Zn---I bond distances are in the range 2.6035 (3)--2.6409 (3) Å, and I---Zn---I bond angles lie in the range 106.583 (11)--114.187 (11)°.  Bond distances and angles of the cations show normal values (Allen *et al.*,  1987) and are comparable with closely related structures (Chantrapromma *et al.*,  2006*a*,*b*, 2007*a*,*b*,*c*; Fun *et al.*,  2006; Jindawong *et al.*,  2005). 

In the crystal packing, the cations are linked together through O---H···O hydrogen bonds and weak C---H···O interactions (Table 1).  The cations are also linked to the ZnI~4~^2-^ anions through weak C27---H27A···I4 interactions (symmetry code: -1 + *x*, *y*, -1 + *z*).  The methanol molecule links with the cation by an O3---H1O3···O5 hydrogen bond (symmetry code: 1 - *x*, -1/2 + *y*, 1/2 - *z*) and with the ZnI~4~^2-^ anion by an O5---H1O5···I1 hydrogen bond (symmetry code: 1 - *x*, 1 - *y*, 1 - *z*).  The cations are arranged in an antiparallel manner and stacked along the *a* axis in such a way that the centroid--centroid distance between the C1--C6 (*Cg*~1~) and C12--C17 (*Cg*~2~) rings is 3.6054 (15)Å (symmetry code: 1 - *x*, 1 - *y*, 1 - *z*) and that between the C20--C25 (*Cg*~3~) and C31--C36 (*Cg*~4~) rings is 3.6057 (15)Å (symmetry code: 1 - *x*, 1 - *y*, -*z*), indicating π--π interactions.  The crystal is further stabilized by C---H···π interactions (Table 1); *Cg*~2~ and *Cg*~4~ are the centroids of the C12--C17 and C31--C36 benzene rings, respectively. 

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

The title compound was synthesized by mixing a solution of 2-\[(*E*)-2-(3-Hydroxy-4-methoxyphenyl)ethynyl\]-1-methylquinolinium iodide (Chantrapromma *et al.*,  2006*a*) (0.20 g, 0.48 mmol) in hot methanol (50 ml) and a solution of ZnI~2~ (0.19 g, 0.48 mmol) in hot methanol (30 ml).  The mixture was stirred for half an hour and then left at room-temperature.  The title compound formed as a red solid after 2 days.  Red plates suitable for X-ray diffraction analysis were obtained by recrystallization from a methanol/ethanol (1:2 *v*/*v*) by slow evaporation of the solvents at ambient temperature after several days, *M*.p.  493--494 K.

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

All H atoms were placed in calculated positions with an O---H distance of 0.82 Å and C---H distances in the range 0.93--0.97 Å. The *U*~iso~(H) values were constrained to be 1.5*U*~eq~ of the carrier atom for hydroxyl and methyl H atoms, and 1.2*U*~eq~(C) for the remaining H atoms.  A rotating group model was used for the methyl groups.  The highest residual electron density peak is located at 0.76 Å from I4 and the deepest hole is located at 0.50 Å from I4. 

Figures
=======

![ The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.  The dashed lines indicate O---H···O hydrogen bonds.](e-64-0m126-fig1){#Fap1}

![ The crystal packing of (I), viewed down the b axis.  Hydrogen bonds are shown as dashed lines.](e-64-0m126-fig2){#Fap2}

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

  --------------------------------------- ----------------------------------------
  (C~19~H~18~NO~2~)~2~\[ZnI~4~\]·CH~4~O   *F*~000~ = 2280
  *M~r~* = 1189.72                        *D*~x~ = 1.974 Mg m^−3^
  Monoclinic, *P*2~1~/*c*                 Melting point = 493--494 K
  Hall symbol: -P 2ybc                    Mo *K*α radiation λ = 0.71073 Å
  *a* = 8.6449 (1) Å                      Cell parameters from 18959 reflections
  *b* = 23.4312 (4) Å                     θ = 1.4--36.0º
  *c* = 19.7763 (3) Å                     µ = 3.74 mm^−1^
  β = 91.724 (1)º                         *T* = 100.0 (1) K
  *V* = 4004.08 (10) Å^3^                 Plate, orange
  *Z* = 4                                 0.43 × 0.28 × 0.13 mm
  --------------------------------------- ----------------------------------------

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

  --------------------------------------------------------- ---------------------------------------
  Bruker SMART APEX2 CCD area-detector diffractometer       18959 independent reflections
  Radiation source: fine-focus sealed tube                  15305 reflections with *I* \> 2σ(*I*)
  Monochromator: graphite                                   *R*~int~ = 0.033
  Detector resolution: 8.33 pixels mm^-1^                   θ~max~ = 36.0º
  *T* = 100.0(1) K                                          θ~min~ = 1.4º
  ω scans                                                   *h* = −14→14
  Absorption correction: multi-scan(SADABS; Bruker, 2005)   *k* = −38→38
  *T*~min~ = 0.295, *T*~max~ = 0.646                        *l* = −32→32
  100181 measured reflections                               
  --------------------------------------------------------- ---------------------------------------

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

  ---------------------------------------------------------------- ---------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                                             Secondary atom site location: difference Fourier map
  Least-squares matrix: full                                       Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.035                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.091                                               *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0361*P*)^2^ + 5.8575*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.10                                                       (Δ/σ)~max~ = 0.003
  18959 reflections                                                Δρ~max~ = 4.98 e Å^−3^
  465 parameters                                                   Δρ~min~ = −1.46 e Å^−3^
  Primary atom site location: structure-invariant direct methods   Extinction correction: none
  ---------------------------------------------------------------- ---------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental.  The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. 
  Geometry.  All e.s.d.\'s (except the e.s.d.  in the dihedral angle between two l.s.  planes) are estimated using the full covariance matrix.  The cell e.s.d.\'s are taken into account individually in the estimation of e.s.d.\'s in distances, angles and torsion angles; correlations between e.s.d.\'s in cell parameters are only used when they are defined by crystal symmetry.  An approximate (isotropic) treatment of cell e.s.d.\'s is used for estimating e.s.d.\'s 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^ \> σ(*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~   
  Zn1    1.00933 (3)     0.428527 (12)   0.759635 (14)   0.01632 (5)          
  I1     0.961758 (19)   0.360714 (7)    0.654410 (8)    0.01980 (4)          
  I2     0.763779 (18)   0.492846 (7)    0.768472 (8)    0.02042 (4)          
  I3     1.242365 (18)   0.496650 (7)    0.741500 (8)    0.01896 (3)          
  I4     1.06173 (2)     0.361619 (7)    0.865320 (8)    0.02277 (4)          
  O1     0.4535 (3)      0.23008 (8)     0.41531 (10)    0.0276 (4)           
  H1O1   0.3889          0.2141          0.3908          0.041\*              
  O2     0.2948 (2)      0.26419 (8)     0.30840 (10)    0.0228 (4)           
  N1     0.7449 (2)      0.57253 (9)     0.48296 (10)    0.0157 (3)           
  C1     0.8311 (3)      0.61157 (10)    0.52232 (11)    0.0157 (4)           
  C2     0.8240 (3)      0.67052 (11)    0.50971 (12)    0.0195 (4)           
  H2A    0.7600          0.6848          0.4751          0.023\*              
  C3     0.9135 (3)      0.70685 (12)    0.54942 (13)    0.0217 (5)           
  H3A    0.9080          0.7459          0.5414          0.026\*              
  C4     1.0122 (3)      0.68662 (12)    0.60141 (13)    0.0226 (5)           
  H4A    1.0736          0.7119          0.6266          0.027\*              
  C5     1.0179 (3)      0.62947 (12)    0.61501 (13)    0.0218 (5)           
  H5A    1.0824          0.6160          0.6499          0.026\*              
  C6     0.9259 (3)      0.59056 (11)    0.57618 (12)    0.0179 (4)           
  C7     0.9253 (3)      0.53154 (11)    0.59081 (12)    0.0202 (4)           
  H7A    0.9854          0.5174          0.6268          0.024\*              
  C8     0.8368 (3)      0.49546 (11)    0.55219 (13)    0.0204 (4)           
  H8A    0.8354          0.4568          0.5626          0.024\*              
  C9     0.7464 (3)      0.51611 (10)    0.49612 (12)    0.0166 (4)           
  C10    0.6567 (3)      0.47728 (11)    0.45303 (13)    0.0209 (4)           
  H10A   0.5975          0.4932          0.4178          0.025\*              
  C11    0.6525 (3)      0.42026 (11)    0.46004 (12)    0.0182 (4)           
  H11A   0.7128          0.4042          0.4948          0.022\*              
  C12    0.5606 (3)      0.38162 (10)    0.41721 (12)    0.0166 (4)           
  C13    0.5545 (3)      0.32353 (10)    0.43517 (12)    0.0184 (4)           
  H13A   0.6117          0.3103          0.4725          0.022\*              
  C14    0.4634 (3)      0.28614 (10)    0.39728 (12)    0.0180 (4)           
  C15    0.3786 (3)      0.30571 (10)    0.34013 (11)    0.0165 (4)           
  C16    0.3839 (3)      0.36292 (10)    0.32192 (12)    0.0175 (4)           
  H16A   0.3272          0.3760          0.2843          0.021\*              
  C17    0.4750 (3)      0.40049 (11)    0.36050 (12)    0.0186 (4)           
  H17A   0.4789          0.4388          0.3483          0.022\*              
  C18    0.6509 (3)      0.59471 (11)    0.42510 (13)    0.0217 (5)           
  H18A   0.6655          0.5710          0.3863          0.033\*              
  H18B   0.6825          0.6330          0.4152          0.033\*              
  H18C   0.5436          0.5946          0.4363          0.033\*              
  C19    0.2009 (3)      0.27958 (12)    0.25072 (13)    0.0235 (5)           
  H19A   0.1487          0.2463          0.2332          0.035\*              
  H19B   0.2649          0.2954          0.2166          0.035\*              
  H19C   0.1258          0.3074          0.2636          0.035\*              
  O3     0.4542 (2)      0.23128 (8)     0.09856 (10)    0.0247 (4)           
  H1O3   0.5009          0.2121          0.1272          0.037\*              
  O4     0.6512 (2)      0.26270 (8)     0.19848 (10)    0.0218 (4)           
  N2     0.2764 (2)      0.58183 (9)     0.01849 (10)    0.0164 (3)           
  C20    0.1990 (3)      0.62274 (10)    −0.02175 (11)   0.0162 (4)           
  C21    0.2255 (3)      0.68161 (10)    −0.01304 (12)   0.0183 (4)           
  H21A   0.2984          0.6945          0.0189          0.022\*              
  C22    0.1422 (3)      0.71975 (11)    −0.05247 (13)   0.0211 (4)           
  H22A   0.1611          0.7586          −0.0473         0.025\*              
  C23    0.0292 (3)      0.70159 (12)    −0.10046 (14)   0.0228 (5)           
  H23A   −0.0293         0.7282          −0.1251         0.027\*              
  C24    0.0065 (3)      0.64442 (11)    −0.11052 (13)   0.0209 (4)           
  H24A   −0.0664         0.6322          −0.1429         0.025\*              
  C25    0.0921 (3)      0.60365 (11)    −0.07241 (12)   0.0175 (4)           
  C26    0.0762 (3)      0.54494 (11)    −0.08489 (12)   0.0201 (4)           
  H26A   0.0072          0.5320          −0.1185         0.024\*              
  C27    0.1627 (3)      0.50671 (11)    −0.04747 (13)   0.0201 (4)           
  H27A   0.1556          0.4680          −0.0574         0.024\*              
  C28    0.2627 (3)      0.52520 (10)    0.00606 (11)    0.0159 (4)           
  C29    0.3499 (3)      0.48449 (10)    0.04726 (12)    0.0180 (4)           
  H29A   0.4236          0.4988          0.0780          0.022\*              
  C30    0.3313 (3)      0.42729 (10)    0.04406 (12)    0.0166 (4)           
  H30A   0.2583          0.4130          0.0129          0.020\*              
  C31    0.4171 (3)      0.38655 (10)    0.08570 (11)    0.0158 (4)           
  C32    0.3966 (3)      0.32777 (10)    0.07350 (12)    0.0165 (4)           
  H32A   0.3285          0.3159          0.0390          0.020\*              
  C33    0.4759 (3)      0.28738 (10)    0.11199 (12)    0.0168 (4)           
  C34    0.5794 (3)      0.30554 (10)    0.16424 (11)    0.0156 (4)           
  C35    0.5998 (3)      0.36337 (10)    0.17718 (12)    0.0167 (4)           
  H35A   0.6670          0.3752          0.2120          0.020\*              
  C36    0.5195 (3)      0.40361 (10)    0.13794 (12)    0.0172 (4)           
  H36A   0.5342          0.4423          0.1466          0.021\*              
  C37    0.3706 (3)      0.60281 (11)    0.07710 (12)    0.0208 (4)           
  H37A   0.3660          0.5758          0.1135          0.031\*              
  H37B   0.3308          0.6389          0.0916          0.031\*              
  H37C   0.4760          0.6074          0.0642          0.031\*              
  C38    0.7552 (3)      0.27751 (12)    0.25358 (13)    0.0231 (5)           
  H38A   0.7961          0.2433          0.2741          0.035\*              
  H38B   0.7005          0.2990          0.2866          0.035\*              
  H38C   0.8385          0.3001          0.2370          0.035\*              
  O5     0.4508 (2)      0.64459 (8)     0.32101 (11)    0.0268 (4)           
  H1O5   0.3567          0.6404          0.3178          0.040\*              
  C39    0.5133 (4)      0.64612 (14)    0.25496 (16)    0.0316 (6)           
  H39A   0.4609          0.6749          0.2283          0.047\*              
  H39B   0.4993          0.6096          0.2336          0.047\*              
  H39C   0.6217          0.6549          0.2585          0.047\*              
  ------ --------------- --------------- --------------- -------------------- --

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

  ----- -------------- -------------- -------------- -------------- -------------- --------------
        *U*^11^        *U*^22^        *U*^33^        *U*^12^        *U*^13^        *U*^23^
  Zn1   0.01907 (12)   0.01326 (12)   0.01669 (11)   −0.00056 (9)   0.00160 (9)    −0.00004 (9)
  I1    0.02518 (7)    0.01483 (7)    0.01937 (7)    −0.00102 (5)   0.00049 (6)    −0.00314 (5)
  I2    0.01964 (7)    0.02145 (8)    0.02027 (7)    0.00436 (5)    0.00210 (5)    0.00072 (5)
  I3    0.01906 (6)    0.01890 (7)    0.01889 (6)    −0.00450 (5)   −0.00014 (5)   −0.00183 (5)
  I4    0.03423 (9)    0.01546 (7)    0.01869 (7)    0.00205 (6)    0.00207 (6)    0.00244 (5)
  O1    0.0404 (11)    0.0138 (8)     0.0280 (10)    −0.0005 (7)    −0.0109 (9)    0.0017 (7)
  O2    0.0283 (9)     0.0184 (8)     0.0214 (8)     −0.0023 (7)    −0.0062 (7)    −0.0020 (7)
  N1    0.0155 (8)     0.0180 (9)     0.0135 (8)     0.0002 (6)     −0.0010 (6)    0.0006 (6)
  C1    0.0145 (8)     0.0188 (10)    0.0139 (8)     −0.0014 (7)    0.0013 (7)     −0.0015 (7)
  C2    0.0218 (10)    0.0202 (11)    0.0167 (9)     −0.0032 (8)    0.0000 (8)     −0.0009 (8)
  C3    0.0237 (11)    0.0216 (12)    0.0199 (10)    −0.0044 (9)    0.0016 (9)     −0.0011 (9)
  C4    0.0203 (10)    0.0275 (13)    0.0200 (10)    −0.0048 (9)    −0.0009 (9)    −0.0049 (9)
  C5    0.0196 (10)    0.0271 (13)    0.0185 (10)    −0.0020 (9)    −0.0020 (8)    −0.0044 (9)
  C6    0.0155 (9)     0.0232 (11)    0.0150 (9)     −0.0008 (8)    0.0000 (7)     −0.0003 (8)
  C7    0.0200 (10)    0.0236 (12)    0.0168 (10)    0.0017 (8)     −0.0017 (8)    0.0001 (8)
  C8    0.0233 (10)    0.0197 (11)    0.0179 (10)    0.0000 (8)     −0.0020 (8)    0.0028 (8)
  C9    0.0171 (9)     0.0171 (10)    0.0157 (9)     −0.0008 (7)    0.0000 (7)     0.0002 (7)
  C10   0.0267 (11)    0.0168 (11)    0.0188 (10)    −0.0022 (8)    −0.0056 (9)    0.0016 (8)
  C11   0.0174 (9)     0.0193 (11)    0.0179 (9)     0.0008 (8)     −0.0017 (8)    0.0005 (8)
  C12   0.0165 (9)     0.0172 (10)    0.0160 (9)     0.0003 (7)     0.0000 (8)     0.0002 (7)
  C13   0.0203 (10)    0.0180 (10)    0.0168 (9)     0.0011 (8)     −0.0023 (8)    0.0018 (8)
  C14   0.0224 (10)    0.0135 (10)    0.0179 (9)     0.0017 (8)     −0.0018 (8)    0.0011 (7)
  C15   0.0183 (9)     0.0167 (10)    0.0145 (9)     0.0004 (7)     −0.0002 (7)    0.0000 (7)
  C16   0.0185 (9)     0.0176 (10)    0.0163 (9)     −0.0004 (8)    −0.0016 (8)    0.0028 (8)
  C17   0.0192 (10)    0.0165 (10)    0.0200 (10)    −0.0015 (8)    −0.0004 (8)    0.0020 (8)
  C18   0.0248 (11)    0.0194 (11)    0.0204 (10)    −0.0004 (9)    −0.0067 (9)    −0.0002 (8)
  C19   0.0261 (11)    0.0274 (13)    0.0168 (10)    −0.0027 (10)   −0.0036 (9)    −0.0019 (9)
  O3    0.0359 (10)    0.0135 (8)     0.0237 (9)     −0.0023 (7)    −0.0147 (8)    0.0008 (6)
  O4    0.0239 (8)     0.0195 (8)     0.0214 (8)     −0.0006 (7)    −0.0082 (7)    0.0012 (6)
  N2    0.0189 (8)     0.0157 (9)     0.0145 (8)     −0.0002 (7)    −0.0006 (7)    −0.0003 (6)
  C20   0.0172 (9)     0.0179 (10)    0.0134 (8)     0.0002 (7)     0.0020 (7)     0.0016 (7)
  C21   0.0207 (10)    0.0152 (10)    0.0191 (10)    0.0002 (8)     0.0029 (8)     0.0010 (8)
  C22   0.0254 (11)    0.0169 (11)    0.0210 (10)    0.0035 (8)     0.0033 (9)     0.0020 (8)
  C23   0.0219 (11)    0.0233 (12)    0.0232 (11)    0.0041 (9)     0.0004 (9)     0.0047 (9)
  C24   0.0199 (10)    0.0239 (12)    0.0188 (10)    0.0014 (8)     −0.0002 (8)    0.0026 (9)
  C25   0.0171 (9)     0.0200 (11)    0.0155 (9)     0.0012 (8)     0.0011 (8)     0.0018 (8)
  C26   0.0209 (10)    0.0219 (11)    0.0172 (10)    −0.0009 (8)    −0.0027 (8)    −0.0005 (8)
  C27   0.0237 (10)    0.0174 (11)    0.0189 (10)    −0.0015 (8)    −0.0021 (8)    −0.0017 (8)
  C28   0.0190 (9)     0.0142 (10)    0.0147 (9)     −0.0015 (7)    0.0012 (8)     −0.0009 (7)
  C29   0.0205 (10)    0.0172 (10)    0.0163 (9)     −0.0003 (8)    −0.0016 (8)    0.0004 (8)
  C30   0.0181 (9)     0.0149 (10)    0.0167 (9)     −0.0010 (7)    0.0005 (8)     0.0004 (7)
  C31   0.0163 (9)     0.0160 (10)    0.0151 (9)     −0.0004 (7)    −0.0015 (7)    −0.0013 (7)
  C32   0.0161 (9)     0.0170 (10)    0.0162 (9)     −0.0011 (7)    −0.0030 (7)    −0.0005 (7)
  C33   0.0196 (9)     0.0143 (9)     0.0163 (9)     −0.0015 (7)    −0.0031 (8)    −0.0010 (7)
  C34   0.0167 (9)     0.0151 (10)    0.0150 (9)     −0.0004 (7)    −0.0016 (7)    −0.0003 (7)
  C35   0.0165 (9)     0.0185 (10)    0.0151 (9)     −0.0014 (7)    −0.0019 (7)    −0.0023 (7)
  C36   0.0185 (9)     0.0146 (10)    0.0185 (9)     −0.0003 (7)    −0.0001 (8)    −0.0024 (8)
  C37   0.0279 (11)    0.0175 (11)    0.0168 (10)    −0.0024 (9)    −0.0049 (9)    0.0008 (8)
  C38   0.0210 (10)    0.0282 (13)    0.0196 (10)    −0.0005 (9)    −0.0058 (9)    −0.0009 (9)
  O5    0.0260 (9)     0.0240 (10)    0.0300 (10)    −0.0015 (7)    −0.0094 (8)    0.0014 (8)
  C39   0.0382 (16)    0.0235 (14)    0.0330 (15)    0.0020 (11)    0.0005 (13)    −0.0007 (11)
  ----- -------------- -------------- -------------- -------------- -------------- --------------

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

  ----------------------- -------------- ----------------------- ------------
  Zn1---I3                2.6035 (3)     O3---H1O3               0.8200
  Zn1---I2                2.6135 (3)     O4---C34                1.351 (3)
  Zn1---I1                2.6406 (3)     O4---C38                1.434 (3)
  Zn1---I4                2.6409 (3)     N2---C28                1.354 (3)
  O1---C14                1.364 (3)      N2---C20                1.403 (3)
  O1---H1O1               0.8200         N2---C37                1.480 (3)
  O2---C15                1.356 (3)      C20---C21               1.408 (3)
  O2---C19                1.426 (3)      C20---C25               1.415 (3)
  N1---C9                 1.347 (3)      C21---C22               1.375 (3)
  N1---C1                 1.401 (3)      C21---H21A              0.9300
  N1---C18                1.478 (3)      C22---C23               1.407 (4)
  C1---C2                 1.405 (3)      C22---H22A              0.9300
  C1---C6                 1.413 (3)      C23---C24               1.368 (4)
  C2---C3                 1.380 (3)      C23---H23A              0.9300
  C2---H2A                0.9300         C24---C25               1.412 (3)
  C3---C4                 1.399 (4)      C24---H24A              0.9300
  C3---H3A                0.9300         C25---C26               1.404 (4)
  C4---C5                 1.366 (4)      C26---C27               1.370 (3)
  C4---H4A                0.9300         C26---H26A              0.9300
  C5---C6                 1.420 (3)      C27---C28               1.415 (3)
  C5---H5A                0.9300         C27---H27A              0.9300
  C6---C7                 1.413 (4)      C28---C29               1.450 (3)
  C7---C8                 1.359 (4)      C29---C30               1.351 (3)
  C7---H7A                0.9300         C29---H29A              0.9300
  C8---C9                 1.422 (3)      C30---C31               1.450 (3)
  C8---H8A                0.9300         C30---H30A              0.9300
  C9---C10                1.455 (3)      C31---C36               1.398 (3)
  C10---C11               1.344 (3)      C31---C32               1.409 (3)
  C10---H10A              0.9300         C32---C33               1.384 (3)
  C11---C12               1.459 (3)      C32---H32A              0.9300
  C11---H11A              0.9300         C33---C34               1.412 (3)
  C12---C17               1.397 (3)      C34---C35               1.389 (3)
  C12---C13               1.408 (3)      C35---C36               1.393 (3)
  C13---C14               1.383 (3)      C35---H35A              0.9300
  C13---H13A              0.9300         C36---H36A              0.9300
  C14---C15               1.405 (3)      C37---H37A              0.9600
  C15---C16               1.389 (3)      C37---H37B              0.9600
  C16---C17               1.393 (3)      C37---H37C              0.9600
  C16---H16A              0.9300         C38---H38A              0.9600
  C17---H17A              0.9300         C38---H38B              0.9600
  C18---H18A              0.9600         C38---H38C              0.9600
  C18---H18B              0.9600         O5---C39                1.429 (4)
  C18---H18C              0.9600         O5---H1O5               0.8200
  C19---H19A              0.9600         C39---H39A              0.9600
  C19---H19B              0.9600         C39---H39B              0.9600
  C19---H19C              0.9600         C39---H39C              0.9600
  O3---C33                1.353 (3)                              
                                                                 
  I3---Zn1---I2           106.804 (12)   C34---O4---C38          118.0 (2)
  I3---Zn1---I1           111.295 (11)   C28---N2---C20          122.0 (2)
  I2---Zn1---I1           106.985 (11)   C28---N2---C37          120.7 (2)
  I3---Zn1---I4           110.977 (11)   C20---N2---C37          117.3 (2)
  I2---Zn1---I4           114.187 (11)   N2---C20---C21          121.8 (2)
  I1---Zn1---I4           106.583 (11)   N2---C20---C25          118.4 (2)
  C14---O1---H1O1         109.5          C21---C20---C25         119.8 (2)
  C15---O2---C19          118.2 (2)      C22---C21---C20         119.1 (2)
  C9---N1---C1            122.09 (19)    C22---C21---H21A        120.4
  C9---N1---C18           119.8 (2)      C20---C21---H21A        120.4
  C1---N1---C18           118.1 (2)      C21---C22---C23         121.8 (2)
  N1---C1---C2            121.6 (2)      C21---C22---H22A        119.1
  N1---C1---C6            118.6 (2)      C23---C22---H22A        119.1
  C2---C1---C6            119.8 (2)      C24---C23---C22         119.2 (2)
  C3---C2---C1            119.0 (2)      C24---C23---H23A        120.4
  C3---C2---H2A           120.5          C22---C23---H23A        120.4
  C1---C2---H2A           120.5          C23---C24---C25         120.9 (2)
  C2---C3---C4            121.9 (3)      C23---C24---H24A        119.5
  C2---C3---H3A           119.0          C25---C24---H24A        119.5
  C4---C3---H3A           119.0          C26---C25---C24         121.5 (2)
  C5---C4---C3            119.6 (2)      C26---C25---C20         119.5 (2)
  C5---C4---H4A           120.2          C24---C25---C20         119.0 (2)
  C3---C4---H4A           120.2          C27---C26---C25         119.8 (2)
  C4---C5---C6            120.4 (2)      C27---C26---H26A        120.1
  C4---C5---H5A           119.8          C25---C26---H26A        120.1
  C6---C5---H5A           119.8          C26---C27---C28         121.0 (2)
  C1---C6---C7            119.3 (2)      C26---C27---H27A        119.5
  C1---C6---C5            119.1 (2)      C28---C27---H27A        119.5
  C7---C6---C5            121.5 (2)      N2---C28---C27          118.9 (2)
  C8---C7---C6            119.9 (2)      N2---C28---C29          120.1 (2)
  C8---C7---H7A           120.0          C27---C28---C29         121.0 (2)
  C6---C7---H7A           120.0          C30---C29---C28         124.5 (2)
  C7---C8---C9            120.9 (2)      C30---C29---H29A        117.7
  C7---C8---H8A           119.6          C28---C29---H29A        117.7
  C9---C8---H8A           119.6          C29---C30---C31         124.6 (2)
  N1---C9---C8            119.1 (2)      C29---C30---H30A        117.7
  N1---C9---C10           119.9 (2)      C31---C30---H30A        117.7
  C8---C9---C10           121.0 (2)      C36---C31---C32         118.7 (2)
  C11---C10---C9          125.2 (2)      C36---C31---C30         122.2 (2)
  C11---C10---H10A        117.4          C32---C31---C30         119.1 (2)
  C9---C10---H10A         117.4          C33---C32---C31         121.1 (2)
  C10---C11---C12         125.0 (2)      C33---C32---H32A        119.4
  C10---C11---H11A        117.5          C31---C32---H32A        119.4
  C12---C11---H11A        117.5          O3---C33---C32          119.5 (2)
  C17---C12---C13         119.0 (2)      O3---C33---C34          121.2 (2)
  C17---C12---C11         122.4 (2)      C32---C33---C34         119.3 (2)
  C13---C12---C11         118.5 (2)      O4---C34---C35          125.3 (2)
  C14---C13---C12         120.0 (2)      O4---C34---C33          114.5 (2)
  C14---C13---H13A        120.0          C35---C34---C33         120.2 (2)
  C12---C13---H13A        120.0          C34---C35---C36         119.9 (2)
  O1---C14---C13          120.5 (2)      C34---C35---H35A        120.0
  O1---C14---C15          119.3 (2)      C36---C35---H35A        120.0
  C13---C14---C15         120.2 (2)      C35---C36---C31         120.8 (2)
  O2---C15---C16          126.4 (2)      C35---C36---H36A        119.6
  O2---C15---C14          113.4 (2)      C31---C36---H36A        119.6
  C16---C15---C14         120.2 (2)      N2---C37---H37A         109.5
  C15---C16---C17         119.4 (2)      N2---C37---H37B         109.5
  C15---C16---H16A        120.3          H37A---C37---H37B       109.5
  C17---C16---H16A        120.3          N2---C37---H37C         109.5
  C16---C17---C12         121.1 (2)      H37A---C37---H37C       109.5
  C16---C17---H17A        119.4          H37B---C37---H37C       109.5
  C12---C17---H17A        119.4          O4---C38---H38A         109.5
  N1---C18---H18A         109.5          O4---C38---H38B         109.5
  N1---C18---H18B         109.5          H38A---C38---H38B       109.5
  H18A---C18---H18B       109.5          O4---C38---H38C         109.5
  N1---C18---H18C         109.5          H38A---C38---H38C       109.5
  H18A---C18---H18C       109.5          H38B---C38---H38C       109.5
  H18B---C18---H18C       109.5          C39---O5---H1O5         109.5
  O2---C19---H19A         109.5          O5---C39---H39A         109.5
  O2---C19---H19B         109.5          O5---C39---H39B         109.5
  H19A---C19---H19B       109.5          H39A---C39---H39B       109.5
  O2---C19---H19C         109.5          O5---C39---H39C         109.5
  H19A---C19---H19C       109.5          H39A---C39---H39C       109.5
  H19B---C19---H19C       109.5          H39B---C39---H39C       109.5
  C33---O3---H1O3         109.5                                  
                                                                 
  C9---N1---C1---C2       −177.6 (2)     C28---N2---C20---C21    −173.4 (2)
  C18---N1---C1---C2      2.9 (3)        C37---N2---C20---C21    8.6 (3)
  C9---N1---C1---C6       2.0 (3)        C28---N2---C20---C25    6.4 (3)
  C18---N1---C1---C6      −177.6 (2)     C37---N2---C20---C25    −171.7 (2)
  N1---C1---C2---C3       −178.9 (2)     N2---C20---C21---C22    −177.8 (2)
  C6---C1---C2---C3       1.6 (4)        C25---C20---C21---C22   2.5 (4)
  C1---C2---C3---C4       0.7 (4)        C20---C21---C22---C23   1.1 (4)
  C2---C3---C4---C5       −1.9 (4)       C21---C22---C23---C24   −3.1 (4)
  C3---C4---C5---C6       0.8 (4)        C22---C23---C24---C25   1.5 (4)
  N1---C1---C6---C7       −3.1 (3)       C23---C24---C25---C26   −176.3 (2)
  C2---C1---C6---C7       176.4 (2)      C23---C24---C25---C20   2.1 (4)
  N1---C1---C6---C5       177.9 (2)      N2---C20---C25---C26    −5.4 (3)
  C2---C1---C6---C5       −2.6 (3)       C21---C20---C25---C26   174.4 (2)
  C4---C5---C6---C1       1.4 (4)        N2---C20---C25---C24    176.2 (2)
  C4---C5---C6---C7       −177.6 (2)     C21---C20---C25---C24   −4.0 (3)
  C1---C6---C7---C8       1.5 (4)        C24---C25---C26---C27   179.1 (2)
  C5---C6---C7---C8       −179.4 (2)     C20---C25---C26---C27   0.8 (4)
  C6---C7---C8---C9       1.2 (4)        C25---C26---C27---C28   3.2 (4)
  C1---N1---C9---C8       0.8 (3)        C20---N2---C28---C27    −2.5 (3)
  C18---N1---C9---C8      −179.7 (2)     C37---N2---C28---C27    175.4 (2)
  C1---N1---C9---C10      −179.0 (2)     C20---N2---C28---C29    177.5 (2)
  C18---N1---C9---C10     0.5 (3)        C37---N2---C28---C29    −4.6 (3)
  C7---C8---C9---N1       −2.4 (4)       C26---C27---C28---N2    −2.4 (4)
  C7---C8---C9---C10      177.4 (2)      C26---C27---C28---C29   177.7 (2)
  N1---C9---C10---C11     178.1 (3)      N2---C28---C29---C30    172.1 (2)
  C8---C9---C10---C11     −1.7 (4)       C27---C28---C29---C30   −7.9 (4)
  C9---C10---C11---C12    179.1 (2)      C28---C29---C30---C31   −179.3 (2)
  C10---C11---C12---C17   4.9 (4)        C29---C30---C31---C36   5.7 (4)
  C10---C11---C12---C13   −173.1 (3)     C29---C30---C31---C32   −174.6 (2)
  C17---C12---C13---C14   −0.7 (4)       C36---C31---C32---C33   −0.2 (4)
  C11---C12---C13---C14   177.4 (2)      C30---C31---C32---C33   −180.0 (2)
  C12---C13---C14---O1    −178.3 (2)     C31---C32---C33---O3    −179.5 (2)
  C12---C13---C14---C15   1.0 (4)        C31---C32---C33---C34   −0.2 (4)
  C19---O2---C15---C16    −0.4 (4)       C38---O4---C34---C35    1.2 (4)
  C19---O2---C15---C14    178.4 (2)      C38---O4---C34---C33    −178.3 (2)
  O1---C14---C15---O2     −0.5 (3)       O3---C33---C34---O4     −0.4 (3)
  C13---C14---C15---O2    −179.8 (2)     C32---C33---C34---O4    −179.7 (2)
  O1---C14---C15---C16    178.3 (2)      O3---C33---C34---C35    −180.0 (2)
  C13---C14---C15---C16   −1.0 (4)       C32---C33---C34---C35   0.7 (4)
  O2---C15---C16---C17    179.2 (2)      O4---C34---C35---C36    179.6 (2)
  C14---C15---C16---C17   0.5 (4)        C33---C34---C35---C36   −0.9 (4)
  C15---C16---C17---C12   −0.2 (4)       C34---C35---C36---C31   0.5 (4)
  C13---C12---C17---C16   0.2 (4)        C32---C31---C36---C35   0.0 (4)
  C11---C12---C17---C16   −177.7 (2)     C30---C31---C36---C35   179.8 (2)
  ----------------------- -------------- ----------------------- ------------

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

  ---------------------- --------- --------- ------------- ---------------
  *D*---H···*A*          *D*---H   H···*A*   *D*···*A*     *D*---H···*A*
  O1---H1O1···O2         0.82      2.15      2.611 (3)     116
  O3---H1O3···O4         0.82      2.23      2.673 (3)     114
  O3---H1O3···O5^i^      0.82      1.92      2.693 (3)     156
  O5---H1O5···I1^ii^     0.82      2.82      3.6161 (17)   163
  C2---H2A···O3^iii^     0.93      2.56      3.476 (3)     167
  C18---H18B···O3^iii^   0.96      2.60      3.355 (3)     136
  C27---H27A···I4^iv^    0.93      3.02      3.899 (3)     158
  C19---H19B···Cg4       0.96      2.99      3.944 (3)     172
  C38---H38B···Cg2       0.96      2.94      3.871 (3)     165
  ---------------------- --------- --------- ------------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*            *D*---H   H⋯*A*   *D*⋯*A*       *D*---H⋯*A*
  ---------------------- --------- ------- ------------- -------------
  O1---H1*O*1⋯O2         0.82      2.15    2.611 (3)     116
  O3---H1*O*3⋯O4         0.82      2.23    2.673 (3)     114
  O3---H1*O*3⋯O5^i^      0.82      1.92    2.693 (3)     156
  O5---H1*O*5⋯I1^ii^     0.82      2.82    3.6161 (17)   163
  C2---H2*A*⋯O3^iii^     0.93      2.56    3.476 (3)     167
  C18---H18*B*⋯O3^iii^   0.96      2.60    3.355 (3)     136
  C27---H27*A*⋯I4^iv^    0.93      3.02    3.899 (3)     158
  C19---H19*B*⋯*Cg*4     0.96      2.99    3.944 (3)     172
  C38---H38*B*⋯*Cg*2     0.96      2.94    3.871 (3)     165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . * Cg*2 and *Cg*4 are the centroids of the C12--C17 and C31--C36 benzene rings, respectively. 

[^1]: Additional correspondence author, email: suchada.c\@psu.ac.th
