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

For background details and biological applications of quinolines, see: Markees *et al.* ( 1970[@bb9]); Campbell *et al.* ( 1998[@bb3]); Kalluraya & Sreenivasa (1998[@bb8]).  For the biological activity of chalcones, see: Dimmock *et al.* ( 1999[@bb4]); Xiang *et al.* ( 2006[@bb13]).  For related structures, see: Prasath *et al.* ( 2010[@bb10]); Kaiser *et al.* ( 2009[@bb7]). 

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~20~H~16~ClNO*M* *~r~* = 321.79Triclinic,*a* = 11.3172 (5) Å*b* = 12.0268 (4) Å*c* = 12.6634 (5) Åα = 111.318 (3)°β = 91.620 (3)°γ = 94.581 (3)°*V* = 1597.50 (11) Å^3^*Z* = 4Mo *K*α radiationμ = 0.24 mm^−1^*T* = 100 K0.30 × 0.20 × 0.10 mm

### Data collection {#sec2.1.2}

Agilent SuperNova Dual diffractometer with an Atlas detectorAbsorption correction: multi-scan (*CrysAlis PRO*; Agilent, 2010[@bb1]) *T* ~min~ = 0.931, *T* ~max~ = 0.97613075 measured reflections6879 independent reflections5750 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.023

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.038*wR*(*F* ^2^) = 0.109*S* = 1.086879 reflections419 parametersH-atom parameters constrainedΔρ~max~ = 0.30 e Å^−3^Δρ~min~ = −0.30 e Å^−3^

 {#d5e488}

Data collection: *CrysAlis PRO* (Agilent, 2010[@bb1]); cell refinement: *CrysAlis PRO*; data reduction: *CrysAlis PRO*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb11]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb11]); molecular graphics: *ORTEP-3* (Farrugia, 1997[@bb5]), *DIAMOND* (Brandenburg, 2006[@bb2]), Qmol (Gans & Shalloway, 2001[@bb6]); software used to prepare material for publication: *publCIF* (Westrip, 2010[@bb12]). 

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

Crystal structure: contains datablocks general, I. DOI: [10.1107/S1600536811007835/hg5005sup1.cif](http://dx.doi.org/10.1107/S1600536811007835/hg5005sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536811007835/hg5005Isup2.hkl](http://dx.doi.org/10.1107/S1600536811007835/hg5005Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?hg5005&file=hg5005sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?hg5005sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?hg5005&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [HG5005](http://scripts.iucr.org/cgi-bin/sendsup?hg5005)). 

BP acknowledges the Department of Science and Technology (DST), India, for a research grant (SR/FTP/CS-57/2007).  The University of Malaya is thanked for support of the crystallographic facility. 

Comment
=======

Quinoline derivatives find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees *et al.*,  1970; Campbell *et al.*,  1998; Kalluraya & Sreenivasa, 1998).  Quinoline chalcone analogues have also attracted significant attention as a result of their bio-activity, *e.g*.  anti-plasmodial, anti-microbial, anti-malarial and anti-cancer (Dimmock *et al.*,  1999; Xiang *et al.*,  2006).  In continuation of structural studies of these derivatives (Kaiser *et al.*,  2009; Prasath *et al.*,  2010), the title compound, (I), was investigated. 

Two independent molecules comprise the asymmetric unit of (I), Figs 1 and 2.  Each features an *E* configuration about the C═C bond \[C13═C14 is 1.342 (2) Å and C33═C34 is 1.338 (2) Å\].  Differences between the independent molecules are highlighted in the overlay diagram, Fig.  3, and relate to the twist about the C9---C12 \[C29---C32\] bond as seen in the C8---C9---C12---C13 and C28---C29---C32---C33 torsion angles of 69.5 (2) and 86.0 (2) °, respectively. 

Molecules are consolidated in the crystal packing by a combination of C---H···O, C---H···N, and C---H···π interactions as detailed in Table 1 as well as π···π contacts, with shortest contact of this type occurring between the two independent molecules \[*Cg*(C1--C6)···*Cg*(C21--C26) = 3.6719 (11) Å, angle between rings = 1.27 (9) °\], Fig.  4. 

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

A mixture of 3-acetyl-2,4-dimethylquinoline (0.01 *M*), 4-chlorobenzaldehyde (0.01 *M*) and a catalytic amount of KOH in distilled ethanol was stirred for 12 h at room temperature.  The resulting mixture was neutralized with dilute acetic acid.  The resultant solid was filtered, dried and purified by column chromatography using a 1:3 mixture of ethyl acetate and hexane.  Re-crystallization was by slow evaporation of acetone solution of (I) which yielded colourless prisms in 86% yield; *M*.pt.  426--428 K.

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

The C-bound H atoms were geometrically placed (C--H = 0.95--0.98 Å) and refined as riding with *U~iso~*(H) = 1.2--1.5*U~eq~*(C). 

Figures
=======

![ The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.](e-67-0o796-fig1){#Fap1}

![ The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.](e-67-0o796-fig2){#Fap2}

![ Overlay diagram of the two independent molecules in (I) with the the first independent molecule shown in red.](e-67-0o796-fig3){#Fap3}

![ A view in projection down the a axis of the packing in (I).  The C---H···N, C---H···O, C---H···π, and π···π interactions are shown as blue, orange, green and purple dashed lines, respectively.](e-67-0o796-fig4){#Fap4}

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

  ------------------------- ---------------------------------------
  C~20~H~16~ClNO            *Z* = 4
  *M~r~* = 321.79           *F*(000) = 672
  Triclinic, *P*1           *D*~x~ = 1.338 Mg m^−3^
  Hall symbol: -P 1         Mo *K*α radiation, λ = 0.71073 Å
  *a* = 11.3172 (5) Å       Cell parameters from 6658 reflections
  *b* = 12.0268 (4) Å       θ = 2.4--29.2°
  *c* = 12.6634 (5) Å       µ = 0.24 mm^−1^
  α = 111.318 (3)°          *T* = 100 K
  β = 91.620 (3)°           Prismatic, colourless
  γ = 94.581 (3)°           0.30 × 0.20 × 0.10 mm
  *V* = 1597.50 (11) Å^3^   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------------- --------------------------------------
  Agilent SuperNova Dual diffractometer with an Atlas detector        6879 independent reflections
  Radiation source: SuperNova (Mo) X-ray Source                       5750 reflections with *I* \> 2σ(*I*)
  Mirror                                                              *R*~int~ = 0.023
  Detector resolution: 10.4041 pixels mm^-1^                          θ~max~ = 27.0°, θ~min~ = 2.4°
  ω scan                                                              *h* = −11→14
  Absorption correction: multi-scan (*CrysAlis PRO*; Agilent, 2010)   *k* = −14→15
  *T*~min~ = 0.931, *T*~max~ = 0.976                                  *l* = −16→16
  13075 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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.038   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.109                  H-atom parameters constrained
  *S* = 1.08                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0488*P*)^2^ + 0.5056*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  6879 reflections                      (Δ/σ)~max~ = 0.001
  419 parameters                        Δρ~max~ = 0.30 e Å^−3^
  0 restraints                          Δρ~min~ = −0.30 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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~   
  Cl1    0.30818 (4)    1.10668 (4)    0.01940 (3)    0.02200 (11)         
  Cl2    0.94188 (4)    −0.07691 (3)   0.17947 (4)    0.02391 (11)         
  O1     0.27425 (11)   0.43144 (11)   0.19111 (10)   0.0237 (3)           
  O2     1.01594 (11)   0.65990 (10)   0.11770 (10)   0.0244 (3)           
  N1     0.63923 (12)   0.47181 (12)   0.31920 (11)   0.0181 (3)           
  N2     0.69353 (12)   0.77627 (12)   0.28121 (11)   0.0183 (3)           
  C1     0.65234 (14)   0.55428 (14)   0.42863 (13)   0.0169 (3)           
  C2     0.75852 (15)   0.56068 (15)   0.49298 (14)   0.0208 (4)           
  H2     0.8172         0.5082         0.4604         0.025\*              
  C3     0.77728 (16)   0.64175 (16)   0.60164 (14)   0.0240 (4)           
  H3     0.8489         0.6454         0.6443         0.029\*              
  C4     0.69125 (17)   0.71968 (16)   0.65055 (14)   0.0255 (4)           
  H4     0.7052         0.7762         0.7260         0.031\*              
  C5     0.58725 (16)   0.71496 (15)   0.59032 (14)   0.0212 (4)           
  H5     0.5295         0.7679         0.6247         0.025\*              
  C6     0.56483 (15)   0.63183 (14)   0.47703 (13)   0.0164 (3)           
  C7     0.36198 (16)   0.70116 (16)   0.46065 (15)   0.0230 (4)           
  H7A    0.2937         0.6807         0.4054         0.034\*              
  H7B    0.3912         0.7856         0.4806         0.034\*              
  H7C    0.3378         0.6877         0.5291         0.034\*              
  C8     0.45920 (15)   0.62335 (14)   0.40959 (13)   0.0168 (3)           
  C9     0.44899 (14)   0.54124 (14)   0.29911 (13)   0.0167 (3)           
  C10    0.54205 (15)   0.46604 (14)   0.25775 (13)   0.0178 (3)           
  C11    0.53295 (16)   0.37519 (16)   0.13797 (14)   0.0268 (4)           
  H11A   0.6084         0.3395         0.1209         0.040\*              
  H11B   0.5154         0.4148         0.0848         0.040\*              
  H11C   0.4691         0.3122         0.1303         0.040\*              
  C12    0.34040 (15)   0.52485 (15)   0.22153 (13)   0.0185 (3)           
  C13    0.31533 (15)   0.61965 (15)   0.17951 (13)   0.0193 (3)           
  H13    0.2394         0.6139         0.1428         0.023\*              
  C14    0.39258 (14)   0.71409 (14)   0.18947 (13)   0.0169 (3)           
  H14    0.4673         0.7207         0.2284         0.020\*              
  C15    0.37082 (14)   0.80785 (14)   0.14499 (13)   0.0163 (3)           
  C16    0.45856 (15)   0.90306 (15)   0.16371 (13)   0.0185 (3)           
  H16    0.5317         0.9044         0.2030         0.022\*              
  C17    0.44053 (15)   0.99568 (15)   0.12578 (14)   0.0202 (3)           
  H17    0.5002         1.0603         0.1395         0.024\*              
  C18    0.33394 (15)   0.99194 (14)   0.06763 (13)   0.0172 (3)           
  C19    0.24596 (15)   0.89808 (14)   0.04630 (13)   0.0175 (3)           
  H19    0.1737         0.8965         0.0055         0.021\*              
  C20    0.26433 (15)   0.80688 (14)   0.08494 (13)   0.0176 (3)           
  H20    0.2041         0.7426         0.0707         0.021\*              
  C21    0.73255 (15)   0.84513 (14)   0.39108 (13)   0.0169 (3)           
  C22    0.65761 (15)   0.92923 (15)   0.45675 (14)   0.0214 (4)           
  H22    0.5828         0.9355         0.4246         0.026\*              
  C23    0.69216 (16)   1.00162 (15)   0.56633 (14)   0.0234 (4)           
  H23    0.6414         1.0582         0.6096         0.028\*              
  C24    0.80236 (17)   0.99265 (16)   0.61511 (14)   0.0248 (4)           
  H24    0.8256         1.0430         0.6913         0.030\*              
  C25    0.87611 (16)   0.91200 (15)   0.55367 (14)   0.0223 (4)           
  H25    0.9503         0.9067         0.5877         0.027\*              
  C26    0.84371 (14)   0.83584 (14)   0.43949 (13)   0.0165 (3)           
  C27    1.03653 (16)   0.73737 (16)   0.41847 (15)   0.0240 (4)           
  H27A   1.0757         0.6761         0.3601         0.036\*              
  H27B   1.0249         0.7130         0.4837         0.036\*              
  H27C   1.0862         0.8140         0.4430         0.036\*              
  C28    0.91775 (14)   0.75128 (14)   0.37029 (13)   0.0166 (3)           
  C29    0.87938 (14)   0.68731 (13)   0.25941 (13)   0.0156 (3)           
  C30    0.76478 (15)   0.70176 (14)   0.21780 (13)   0.0172 (3)           
  C31    0.72207 (17)   0.63121 (17)   0.09640 (14)   0.0266 (4)           
  H31A   0.6385         0.6425         0.0851         0.040\*              
  H31B   0.7301         0.5459         0.0790         0.040\*              
  H31C   0.7698         0.6592         0.0459         0.040\*              
  C32    0.96148 (14)   0.61323 (14)   0.17584 (13)   0.0177 (3)           
  C33    0.97704 (15)   0.48990 (14)   0.16405 (14)   0.0187 (3)           
  H33    1.0385         0.4512         0.1195         0.022\*              
  C34    0.90871 (14)   0.42888 (14)   0.21311 (13)   0.0164 (3)           
  H34    0.8480         0.4693         0.2576         0.020\*              
  C35    0.91928 (14)   0.30507 (14)   0.20433 (13)   0.0153 (3)           
  C36    0.83251 (15)   0.24830 (15)   0.24922 (14)   0.0191 (3)           
  H36    0.7681         0.2907         0.2845         0.023\*              
  C37    0.83849 (15)   0.13140 (15)   0.24336 (14)   0.0209 (4)           
  H37    0.7794         0.0940         0.2746         0.025\*              
  C38    0.93268 (15)   0.07030 (14)   0.19082 (13)   0.0186 (3)           
  C39    1.02011 (15)   0.12443 (14)   0.14643 (14)   0.0193 (3)           
  H39    1.0844         0.0816         0.1115         0.023\*              
  C40    1.01375 (14)   0.24142 (14)   0.15301 (13)   0.0175 (3)           
  H40    1.0738         0.2786         0.1225         0.021\*              
  ------ -------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------ -------------- --------------- --------------
        *U*^11^       *U*^22^       *U*^33^      *U*^12^        *U*^13^         *U*^23^
  Cl1   0.0232 (2)    0.0193 (2)    0.0263 (2)   0.00249 (16)   0.00071 (17)    0.01157 (17)
  Cl2   0.0277 (2)    0.0146 (2)    0.0308 (2)   0.00188 (17)   −0.00441 (18)   0.01043 (17)
  O1    0.0212 (6)    0.0235 (6)    0.0280 (6)   −0.0027 (5)    −0.0042 (5)     0.0127 (5)
  O2    0.0264 (7)    0.0203 (6)    0.0300 (6)   0.0040 (5)     0.0104 (5)      0.0123 (5)
  N1    0.0164 (7)    0.0177 (7)    0.0191 (7)   0.0026 (6)     0.0009 (6)      0.0051 (6)
  N2    0.0168 (7)    0.0192 (7)    0.0183 (7)   0.0023 (6)     −0.0008 (6)     0.0063 (6)
  C1    0.0179 (8)    0.0165 (8)    0.0176 (8)   −0.0006 (6)    0.0019 (6)      0.0081 (6)
  C2    0.0177 (8)    0.0245 (9)    0.0228 (8)   0.0016 (7)     0.0020 (7)      0.0118 (7)
  C3    0.0221 (9)    0.0320 (10)   0.0193 (8)   −0.0018 (8)    −0.0047 (7)     0.0126 (7)
  C4    0.0339 (10)   0.0244 (9)    0.0163 (8)   −0.0014 (8)    −0.0017 (7)     0.0062 (7)
  C5    0.0273 (9)    0.0193 (8)    0.0179 (8)   0.0040 (7)     0.0030 (7)      0.0072 (7)
  C6    0.0194 (8)    0.0143 (7)    0.0172 (7)   0.0000 (6)     0.0026 (6)      0.0080 (6)
  C7    0.0242 (9)    0.0235 (9)    0.0226 (8)   0.0084 (7)     0.0033 (7)      0.0087 (7)
  C8    0.0194 (8)    0.0154 (8)    0.0187 (8)   0.0029 (6)     0.0026 (7)      0.0096 (6)
  C9    0.0159 (8)    0.0167 (8)    0.0196 (8)   0.0001 (6)     0.0007 (6)      0.0095 (7)
  C10   0.0178 (8)    0.0159 (8)    0.0188 (8)   0.0003 (6)     0.0010 (7)      0.0055 (6)
  C11   0.0228 (9)    0.0270 (9)    0.0222 (9)   0.0059 (8)     −0.0029 (7)     −0.0012 (7)
  C12   0.0165 (8)    0.0209 (8)    0.0185 (8)   0.0035 (7)     0.0032 (7)      0.0073 (7)
  C13   0.0162 (8)    0.0222 (8)    0.0194 (8)   0.0050 (7)     −0.0001 (7)     0.0071 (7)
  C14   0.0157 (8)    0.0202 (8)    0.0135 (7)   0.0050 (7)     0.0011 (6)      0.0041 (6)
  C15   0.0167 (8)    0.0180 (8)    0.0133 (7)   0.0040 (6)     0.0030 (6)      0.0041 (6)
  C16   0.0152 (8)    0.0234 (8)    0.0165 (8)   0.0026 (7)     −0.0006 (6)     0.0067 (7)
  C17   0.0183 (8)    0.0213 (8)    0.0199 (8)   −0.0014 (7)    0.0004 (7)      0.0071 (7)
  C18   0.0205 (8)    0.0150 (8)    0.0164 (7)   0.0044 (6)     0.0038 (6)      0.0053 (6)
  C19   0.0168 (8)    0.0166 (8)    0.0171 (8)   0.0042 (7)     0.0005 (6)      0.0032 (6)
  C20   0.0181 (8)    0.0160 (8)    0.0173 (8)   0.0016 (6)     0.0013 (7)      0.0043 (6)
  C21   0.0186 (8)    0.0149 (8)    0.0183 (8)   0.0017 (6)     0.0023 (7)      0.0072 (6)
  C22   0.0204 (9)    0.0222 (9)    0.0231 (8)   0.0065 (7)     0.0035 (7)      0.0090 (7)
  C23   0.0281 (10)   0.0211 (9)    0.0225 (8)   0.0088 (7)     0.0070 (7)      0.0079 (7)
  C24   0.0327 (10)   0.0223 (9)    0.0157 (8)   0.0037 (8)     0.0004 (7)      0.0026 (7)
  C25   0.0252 (9)    0.0216 (9)    0.0198 (8)   0.0030 (7)     −0.0031 (7)     0.0072 (7)
  C26   0.0181 (8)    0.0140 (8)    0.0179 (8)   0.0013 (6)     0.0010 (6)      0.0064 (6)
  C27   0.0208 (9)    0.0242 (9)    0.0250 (9)   0.0069 (7)     −0.0032 (7)     0.0058 (7)
  C28   0.0166 (8)    0.0130 (7)    0.0217 (8)   0.0022 (6)     0.0017 (7)      0.0082 (6)
  C29   0.0171 (8)    0.0117 (7)    0.0190 (8)   0.0005 (6)     0.0024 (6)      0.0068 (6)
  C30   0.0183 (8)    0.0161 (8)    0.0178 (8)   0.0010 (7)     0.0010 (7)      0.0070 (6)
  C31   0.0247 (9)    0.0284 (10)   0.0199 (8)   0.0049 (8)     −0.0021 (7)     0.0007 (7)
  C32   0.0166 (8)    0.0161 (8)    0.0191 (8)   0.0007 (6)     0.0012 (7)      0.0054 (6)
  C33   0.0202 (8)    0.0151 (8)    0.0207 (8)   0.0057 (7)     0.0053 (7)      0.0053 (6)
  C34   0.0163 (8)    0.0147 (8)    0.0162 (7)   0.0036 (6)     0.0015 (6)      0.0028 (6)
  C35   0.0166 (8)    0.0148 (8)    0.0135 (7)   0.0014 (6)     −0.0017 (6)     0.0041 (6)
  C36   0.0197 (8)    0.0185 (8)    0.0195 (8)   0.0040 (7)     0.0043 (7)      0.0068 (7)
  C37   0.0223 (9)    0.0200 (8)    0.0219 (8)   0.0002 (7)     0.0026 (7)      0.0099 (7)
  C38   0.0232 (9)    0.0134 (8)    0.0190 (8)   0.0020 (7)     −0.0054 (7)     0.0060 (6)
  C39   0.0164 (8)    0.0156 (8)    0.0239 (8)   0.0036 (6)     −0.0005 (7)     0.0048 (7)
  C40   0.0162 (8)    0.0156 (8)    0.0199 (8)   0.0009 (6)     0.0005 (7)      0.0059 (6)
  ----- ------------- ------------- ------------ -------------- --------------- --------------

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

  ----------------------- -------------- ----------------------- --------------
  Cl1---C18               1.7404 (16)    C18---C19               1.386 (2)
  Cl2---C38               1.7354 (16)    C19---C20               1.381 (2)
  O1---C12                1.227 (2)      C19---H19               0.9500
  O2---C32                1.2279 (19)    C20---H20               0.9500
  N1---C10                1.312 (2)      C21---C22               1.414 (2)
  N1---C1                 1.375 (2)      C21---C26               1.414 (2)
  N2---C30                1.314 (2)      C22---C23               1.369 (2)
  N2---C21                1.373 (2)      C22---H22               0.9500
  C1---C6                 1.412 (2)      C23---C24               1.405 (3)
  C1---C2                 1.414 (2)      C23---H23               0.9500
  C2---C3                 1.365 (2)      C24---C25               1.364 (2)
  C2---H2                 0.9500         C24---H24               0.9500
  C3---C4                 1.403 (3)      C25---C26               1.420 (2)
  C3---H3                 0.9500         C25---H25               0.9500
  C4---C5                 1.370 (3)      C26---C28               1.426 (2)
  C4---H4                 0.9500         C27---C28               1.507 (2)
  C5---C6                 1.421 (2)      C27---H27A              0.9800
  C5---H5                 0.9500         C27---H27B              0.9800
  C6---C8                 1.424 (2)      C27---H27C              0.9800
  C7---C8                 1.506 (2)      C28---C29               1.371 (2)
  C7---H7A                0.9800         C29---C30               1.433 (2)
  C7---H7B                0.9800         C29---C32               1.510 (2)
  C7---H7C                0.9800         C30---C31               1.504 (2)
  C8---C9                 1.383 (2)      C31---H31A              0.9800
  C9---C10                1.428 (2)      C31---H31B              0.9800
  C9---C12                1.506 (2)      C31---H31C              0.9800
  C10---C11               1.508 (2)      C32---C33               1.461 (2)
  C11---H11A              0.9800         C33---C34               1.338 (2)
  C11---H11B              0.9800         C33---H33               0.9500
  C11---H11C              0.9800         C34---C35               1.467 (2)
  C12---C13               1.466 (2)      C34---H34               0.9500
  C13---C14               1.342 (2)      C35---C40               1.400 (2)
  C13---H13               0.9500         C35---C36               1.400 (2)
  C14---C15               1.466 (2)      C36---C37               1.388 (2)
  C14---H14               0.9500         C36---H36               0.9500
  C15---C16               1.400 (2)      C37---C38               1.389 (2)
  C15---C20               1.404 (2)      C37---H37               0.9500
  C16---C17               1.390 (2)      C38---C39               1.383 (2)
  C16---H16               0.9500         C39---C40               1.387 (2)
  C17---C18               1.384 (2)      C39---H39               0.9500
  C17---H17               0.9500         C40---H40               0.9500
                                                                 
  C10---N1---C1           118.49 (14)    C15---C20---H20         119.6
  C30---N2---C21          118.16 (14)    N2---C21---C22          117.67 (15)
  N1---C1---C6            122.40 (14)    N2---C21---C26          122.79 (14)
  N1---C1---C2            117.73 (14)    C22---C21---C26         119.54 (14)
  C6---C1---C2            119.87 (14)    C23---C22---C21         120.46 (16)
  C3---C2---C1            120.43 (16)    C23---C22---H22         119.8
  C3---C2---H2            119.8          C21---C22---H22         119.8
  C1---C2---H2            119.8          C22---C23---C24         120.31 (15)
  C2---C3---C4            120.26 (16)    C22---C23---H23         119.8
  C2---C3---H3            119.9          C24---C23---H23         119.8
  C4---C3---H3            119.9          C25---C24---C23         120.36 (16)
  C5---C4---C3            120.53 (16)    C25---C24---H24         119.8
  C5---C4---H4            119.7          C23---C24---H24         119.8
  C3---C4---H4            119.7          C24---C25---C26         120.98 (16)
  C4---C5---C6            120.72 (16)    C24---C25---H25         119.5
  C4---C5---H5            119.6          C26---C25---H25         119.5
  C6---C5---H5            119.6          C21---C26---C25         118.34 (14)
  C1---C6---C5            118.19 (15)    C21---C26---C28         118.04 (14)
  C1---C6---C8            118.38 (14)    C25---C26---C28         123.62 (15)
  C5---C6---C8            123.43 (15)    C28---C27---H27A        109.5
  C8---C7---H7A           109.5          C28---C27---H27B        109.5
  C8---C7---H7B           109.5          H27A---C27---H27B       109.5
  H7A---C7---H7B          109.5          C28---C27---H27C        109.5
  C8---C7---H7C           109.5          H27A---C27---H27C       109.5
  H7A---C7---H7C          109.5          H27B---C27---H27C       109.5
  H7B---C7---H7C          109.5          C29---C28---C26         118.19 (14)
  C9---C8---C6            118.16 (14)    C29---C28---C27         121.81 (14)
  C9---C8---C7            122.28 (15)    C26---C28---C27         119.96 (14)
  C6---C8---C7            119.55 (14)    C28---C29---C30         119.89 (14)
  C8---C9---C10           119.42 (15)    C28---C29---C32         121.05 (14)
  C8---C9---C12           122.13 (14)    C30---C29---C32         118.62 (14)
  C10---C9---C12          118.41 (14)    N2---C30---C29          122.82 (14)
  N1---C10---C9           123.13 (14)    N2---C30---C31          117.12 (14)
  N1---C10---C11          116.29 (14)    C29---C30---C31         120.05 (14)
  C9---C10---C11          120.58 (14)    C30---C31---H31A        109.5
  C10---C11---H11A        109.5          C30---C31---H31B        109.5
  C10---C11---H11B        109.5          H31A---C31---H31B       109.5
  H11A---C11---H11B       109.5          C30---C31---H31C        109.5
  C10---C11---H11C        109.5          H31A---C31---H31C       109.5
  H11A---C11---H11C       109.5          H31B---C31---H31C       109.5
  H11B---C11---H11C       109.5          O2---C32---C33          120.45 (14)
  O1---C12---C13          119.77 (15)    O2---C32---C29          117.96 (14)
  O1---C12---C9           120.40 (15)    C33---C32---C29         121.60 (14)
  C13---C12---C9          119.81 (14)    C34---C33---C32         123.07 (15)
  C14---C13---C12         124.27 (15)    C34---C33---H33         118.5
  C14---C13---H13         117.9          C32---C33---H33         118.5
  C12---C13---H13         117.9          C33---C34---C35         125.80 (15)
  C13---C14---C15         125.19 (15)    C33---C34---H34         117.1
  C13---C14---H14         117.4          C35---C34---H34         117.1
  C15---C14---H14         117.4          C40---C35---C36         118.54 (14)
  C16---C15---C20         118.31 (15)    C40---C35---C34         122.29 (14)
  C16---C15---C14         119.19 (14)    C36---C35---C34         119.16 (14)
  C20---C15---C14         122.50 (15)    C37---C36---C35         121.45 (15)
  C17---C16---C15         121.19 (15)    C37---C36---H36         119.3
  C17---C16---H16         119.4          C35---C36---H36         119.3
  C15---C16---H16         119.4          C36---C37---C38         118.57 (15)
  C18---C17---C16         118.76 (16)    C36---C37---H37         120.7
  C18---C17---H17         120.6          C38---C37---H37         120.7
  C16---C17---H17         120.6          C39---C38---C37         121.22 (15)
  C17---C18---C19         121.47 (15)    C39---C38---Cl2         118.80 (12)
  C17---C18---Cl1         119.97 (13)    C37---C38---Cl2         119.98 (13)
  C19---C18---Cl1         118.56 (13)    C38---C39---C40         119.85 (15)
  C20---C19---C18         119.38 (15)    C38---C39---H39         120.1
  C20---C19---H19         120.3          C40---C39---H39         120.1
  C18---C19---H19         120.3          C39---C40---C35         120.35 (15)
  C19---C20---C15         120.89 (15)    C39---C40---H40         119.8
  C19---C20---H20         119.6          C35---C40---H40         119.8
                                                                 
  C10---N1---C1---C6      0.5 (2)        C30---N2---C21---C22    176.92 (14)
  C10---N1---C1---C2      −178.93 (15)   C30---N2---C21---C26    −2.4 (2)
  N1---C1---C2---C3       179.21 (15)    N2---C21---C22---C23    −179.12 (15)
  C6---C1---C2---C3       −0.2 (2)       C26---C21---C22---C23   0.2 (2)
  C1---C2---C3---C4       0.0 (3)        C21---C22---C23---C24   −0.4 (3)
  C2---C3---C4---C5       0.4 (3)        C22---C23---C24---C25   0.2 (3)
  C3---C4---C5---C6       −0.5 (3)       C23---C24---C25---C26   0.2 (3)
  N1---C1---C6---C5       −179.25 (14)   N2---C21---C26---C25    179.46 (15)
  C2---C1---C6---C5       0.2 (2)        C22---C21---C26---C25   0.2 (2)
  N1---C1---C6---C8       0.3 (2)        N2---C21---C26---C28    0.2 (2)
  C2---C1---C6---C8       179.69 (15)    C22---C21---C26---C28   −179.11 (14)
  C4---C5---C6---C1       0.2 (2)        C24---C25---C26---C21   −0.4 (2)
  C4---C5---C6---C8       −179.31 (16)   C24---C25---C26---C28   178.87 (16)
  C1---C6---C8---C9       −1.4 (2)       C21---C26---C28---C29   2.7 (2)
  C5---C6---C8---C9       178.07 (15)    C25---C26---C28---C29   −176.56 (15)
  C1---C6---C8---C7       177.33 (14)    C21---C26---C28---C27   −179.45 (15)
  C5---C6---C8---C7       −3.2 (2)       C25---C26---C28---C27   1.3 (2)
  C6---C8---C9---C10      1.8 (2)        C26---C28---C29---C30   −3.3 (2)
  C7---C8---C9---C10      −176.91 (15)   C27---C28---C29---C30   178.82 (15)
  C6---C8---C9---C12      179.45 (14)    C26---C28---C29---C32   168.91 (14)
  C7---C8---C9---C12      0.7 (2)        C27---C28---C29---C32   −8.9 (2)
  C1---N1---C10---C9      −0.1 (2)       C21---N2---C30---C29    1.7 (2)
  C1---N1---C10---C11     179.24 (14)    C21---N2---C30---C31    −177.48 (14)
  C8---C9---C10---N1      −1.1 (2)       C28---C29---C30---N2    1.2 (2)
  C12---C9---C10---N1     −178.82 (15)   C32---C29---C30---N2    −171.27 (14)
  C8---C9---C10---C11     179.60 (15)    C28---C29---C30---C31   −179.64 (15)
  C12---C9---C10---C11    1.9 (2)        C32---C29---C30---C31   7.9 (2)
  C8---C9---C12---O1      −112.18 (18)   C28---C29---C32---O2    −93.64 (19)
  C10---C9---C12---O1     65.5 (2)       C30---C29---C32---O2    78.7 (2)
  C8---C9---C12---C13     69.5 (2)       C28---C29---C32---C33   86.0 (2)
  C10---C9---C12---C13    −112.79 (17)   C30---C29---C32---C33   −101.63 (18)
  O1---C12---C13---C14    −166.68 (16)   O2---C32---C33---C34    −170.54 (16)
  C9---C12---C13---C14    11.6 (2)       C29---C32---C33---C34   9.8 (3)
  C12---C13---C14---C15   177.97 (14)    C32---C33---C34---C35   179.74 (15)
  C13---C14---C15---C16   178.60 (15)    C33---C34---C35---C40   7.9 (3)
  C13---C14---C15---C20   −0.7 (2)       C33---C34---C35---C36   −172.45 (16)
  C20---C15---C16---C17   1.1 (2)        C40---C35---C36---C37   −0.2 (2)
  C14---C15---C16---C17   −178.23 (14)   C34---C35---C36---C37   −179.86 (15)
  C15---C16---C17---C18   −0.6 (2)       C35---C36---C37---C38   −0.5 (2)
  C16---C17---C18---C19   −0.3 (2)       C36---C37---C38---C39   0.9 (2)
  C16---C17---C18---Cl1   179.76 (12)    C36---C37---C38---Cl2   −178.83 (13)
  C17---C18---C19---C20   0.7 (2)        C37---C38---C39---C40   −0.7 (2)
  Cl1---C18---C19---C20   −179.33 (12)   Cl2---C38---C39---C40   179.07 (12)
  C18---C19---C20---C15   −0.2 (2)       C38---C39---C40---C35   0.0 (2)
  C16---C15---C20---C19   −0.7 (2)       C36---C35---C40---C39   0.5 (2)
  C14---C15---C20---C19   178.65 (14)    C34---C35---C40---C39   −179.90 (15)
  ----------------------- -------------- ----------------------- --------------

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

  -------------------------------------------
  Cg1 is the centroid of the C35--C40 ring. 
  -------------------------------------------

  --------------------- --------- --------- ------------- ---------------
  *D*---H···*A*         *D*---H   H···*A*   *D*···*A*     *D*---H···*A*
  C14---H14···N2        0.95      2.60      3.500 (2)     158
  C20---H20···O2^i^     0.95      2.46      3.317 (2)     150
  C34---H34···N1        0.95      2.51      3.369 (2)     151
  C19---H19···Cg1^ii^   0.95      2.59      3.3826 (17)   142
  --------------------- --------- --------- ------------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

*Cg*1 is the centroid of the C35--C40 ring. 

  *D*---H⋯*A*           *D*---H   H⋯*A*   *D*⋯*A*       *D*---H⋯*A*
  --------------------- --------- ------- ------------- -------------
  C14---H14⋯N2          0.95      2.60    3.500 (2)     158
  C20---H20⋯O2^i^       0.95      2.46    3.317 (2)     150
  C34---H34⋯N1          0.95      2.51    3.369 (2)     151
  C19---H19⋯*Cg*1^ii^   0.95      2.59    3.3826 (17)   142

Symmetry codes: (i) ; (ii) . 

[^1]: Additional correspondence author, e-mail: juliebhavana\@gmail.com.