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

For background to applications of Schiff bases, see: Lozier *et al.* (1975[@bb5]); Kargar *et al.* (2009[@bb4]); Yeap *et al.* (2009[@bb9]). For related structures, see: Higuchi *et al.* (2001[@bb3]); Manseong *et al.* (2006[@bb6]); Vitor *et al.* (2008[@bb8]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~30~H~18~ClNO*M* *~r~* = 443.90Monoclinic,*a* = 12.4929 (6) Å*b* = 10.8699 (7) Å*c* = 16.0758 (8) Åβ = 91.864 (5)°*V* = 2181.9 (2) Å^3^*Z* = 4Mo *K*α radiationμ = 0.20 mm^−1^*T* = 100 K0.32 × 0.28 × 0.25 mm

### Data collection   {#sec2.1.2}

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometerAbsorption correction: multi-scan (*CrysAlis PRO*; Agilent, 2012[@bb1]) *T* ~min~ = 0.866, *T* ~max~ = 1.0008827 measured reflections4461 independent reflections3151 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.041

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.058*wR*(*F* ^2^) = 0.121*S* = 1.094461 reflections298 parametersH-atom parameters constrainedΔρ~max~ = 0.50 e Å^−3^Δρ~min~ = −0.28 e Å^−3^

 {#d5e454}

Data collection: *CrysAlis PRO* (Agilent, 2012[@bb1]); cell refinement: *CrysAlis PRO*; data reduction: *CrysAlis PRO*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *OLEX2* (Dolomanov *et al.*, 2009[@bb2]); software used to prepare material for publication: *OLEX2*.

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

###### 

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536813008015/kq2002sup1.cif](http://dx.doi.org/10.1107/S1600536813008015/kq2002sup1.cif)

###### 

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536813008015/kq2002Isup2.hkl](http://dx.doi.org/10.1107/S1600536813008015/kq2002Isup2.hkl)

###### 

Click here for additional data file.

Supplementary material file. DOI: [10.1107/S1600536813008015/kq2002Isup3.cml](http://dx.doi.org/10.1107/S1600536813008015/kq2002Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?kq2002&file=kq2002sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?kq2002sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?kq2002&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [KQ2002](http://scripts.iucr.org/cgi-bin/sendsup?kq2002)).

We gratefully acknowledge the Natural Science Foundation of China (20702042, 21262028), the Program for Changjiang Scholars and Innovative Research Teams in Universities of the Ministry of Education of China (IRT1177), the Natural Science Foundation of Gansu Province (1208RJZA140) and the NWNU Young Teachers Reseach Improving Program (NWNU-LKQN-10--11) for financial support.

Comment
=======

Schiff bases often exhibit various biological activities, for example, anti-inflammatory, antibacterial, anticancer and antitoxic properties (Lozier *et al.*, 1975). They have also been used as versatile ligands in coordination chemistry (Kargar *et al.*, 2009; Yeap *et al.*, 2009). The present work describes the structure of a new Schiff base, C~30~H~18~ClNO, (I) obtained by the condensation reaction of acenaphthylene-1,2-dione and 5\'-chloro-1,1\':3\',1\'\'-terphenyl-4\'-amine (Figure 1).

The geometrical parameters of I are in good accordance with those found in the related compounds (Higuchi *et al.*, 2001; Manseong *et al.*, 2006; Vitor *et al.*, 2008). The acenaphthylene fragment and two terminal phenyl rings in I are rotated in relative to the central benzene ring by 72.2 (3), 43.2 (3) and 41.2 (3)°, respectively (Figure 2). The molecular conformation of I is supported by the weak intramolecular C20---H20···N2 (Table 1) and C2---H2···π(C13=C14) \[H2···C13 2.76 Å, H2···C14 2.80 Å\] hydrogen bonding interactions (Figure 2).

In the crystal, the molecules form centrosymmetric dimers by the stacking interactions between two neighboring acenaphthylene fragments, with the interplane distance of 3.365 (3) Å. The dimers are bound to each other by the weak C24---H24···N2^i^, C4---H4···Cg1^ii^ (Cg1 is the centroid of the C25/C26/C27/C28/C29/C30 ring) and C6---H6···Cg2^iii^ (Cg2 is the centroid of the C19/C20/C21/C22/C23/C24 ring) hydrogen bonding interactions (Table 1) into 3-dimensional framework. Symmetry codes: (i) --*x*+1/2, *y*+1/2, --*z*+1/2; (ii) *x*--1/2, --*y*+1/2, *z*--1/2; (iii) --*x*+1, --*y*+1, --*z*+1.

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

Formic acid (1 mL) was added to a stirred solution of acenaphthenequinone (1.2 mmol) and 2-chloro-4,6-diphenylaniline (1.2 mmol) in methanol (20 mL). The mixture was refluxed for 24 h, then cooled, and the precipitate was separated by filtration. The solid was recrystallized from dichloromethane/cyclohexane (*v*/*v* = 8:1), washed with cold ethanol and dried under vacuum to give the title compound I. Yield is 0.15 g (83%). Crystals of I suitable for X-ray structure determination were grown from a cyclohexane/dichloromethane (1:2, *v*/*v*) solution. Anal. Calcd. for C~30~H~18~ClNO: C, 81.17; H, 4.09; N,3.16. Found: C, 81.11; H, 4.19; N, 3.12.

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

All hydrogen atoms were placed in the calculated positions with C---H = 0.93 Å and refined in the riding model with fixed isotropic displacement parameters \[*U*~iso~(H) = 1.2*U*~eq~(C)\].

Figures
=======

![A condensation reaction of acenaphthylene-1,2-dione and 5\'-chloro-1,1\':3\',1\'\'-terphenyl-4\'-amine.](e-69-0o624-fig1){#Fap1}

![Molecular structure of I. Displacement ellipsoids are shown at the 40% probability level. H atoms are presented as small spheres of arbitrary radius. The dashed lines indicate the intramolecular C---H···N and C---H···π(C=C) hydrogen bonds.](e-69-0o624-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~30~H~18~ClNO            *F*(000) = 920
  *M~r~* = 443.90           *D*~x~ = 1.351 Mg m^−3^
  Monoclinic, *P*2~1~/*n*   Mo *K*α radiation, λ = 0.7107 Å
  *a* = 12.4929 (6) Å       Cell parameters from 2796 reflections
  *b* = 10.8699 (7) Å       θ = 3.1--28.4°
  *c* = 16.0758 (8) Å       µ = 0.20 mm^−1^
  β = 91.864 (5)°           *T* = 100 K
  *V* = 2181.9 (2) Å^3^     Block, clear light-yellow
  *Z* = 4                   0.32 × 0.28 × 0.25 mm
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------------- --------------------------------------
  Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer            4461 independent reflections
  Radiation source: SuperNova (Mo) X-ray Source                       3151 reflections with *I* \> 2σ(*I*)
  Mirror monochromator                                                *R*~int~ = 0.041
  Detector resolution: 16.0733 pixels mm^-1^                          θ~max~ = 26.4°, θ~min~ = 3.2°
  ω scans                                                             *h* = −15→15
  Absorption correction: multi-scan (*CrysAlis PRO*; Agilent, 2012)   *k* = −13→11
  *T*~min~ = 0.866, *T*~max~ = 1.000                                  *l* = −19→20
  8827 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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.058   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.121                  H-atom parameters constrained
  *S* = 1.09                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.031*P*)^2^ + 0.7817*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4461 reflections                      (Δ/σ)~max~ \< 0.001
  298 parameters                        Δρ~max~ = 0.50 e Å^−3^
  0 restraints                          Δρ~min~ = −0.28 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   0.04696 (5)     0.31870 (6)    0.48276 (4)    0.02604 (18)         
  O1    0.41337 (15)    0.16285 (19)   0.45458 (12)   0.0333 (5)           
  N2    0.23922 (15)    0.29536 (19)   0.37546 (11)   0.0179 (5)           
  C1    0.29301 (19)    0.4619 (3)     0.47857 (15)   0.0226 (6)           
  C2    0.2362 (2)      0.5671 (3)     0.46784 (16)   0.0255 (6)           
  H2    0.1824          0.5737         0.4267         0.031\*              
  C3    0.2617 (2)      0.6671 (3)     0.52178 (18)   0.0335 (7)           
  H3    0.2249          0.7408         0.5143         0.040\*              
  C4    0.3393 (2)      0.6593 (3)     0.58509 (17)   0.0334 (7)           
  H4    0.3515          0.7262         0.6201         0.040\*              
  C5    0.3989 (2)      0.5525 (3)     0.59681 (16)   0.0276 (7)           
  C6    0.4832 (2)      0.5294 (3)     0.65685 (16)   0.0330 (7)           
  H6    0.5019          0.5901         0.6954         0.040\*              
  C7    0.5368 (2)      0.4199 (3)     0.65874 (16)   0.0352 (8)           
  H7    0.5911          0.4087         0.6990         0.042\*              
  C8    0.5140 (2)      0.3233 (3)     0.60276 (15)   0.0317 (7)           
  H8    0.5527          0.2502         0.6045         0.038\*              
  C9    0.4309 (2)      0.3422 (3)     0.54485 (15)   0.0249 (6)           
  C10   0.3752 (2)      0.4534 (3)     0.54261 (15)   0.0250 (6)           
  C11   0.3865 (2)      0.2656 (3)     0.47682 (15)   0.0247 (6)           
  C12   0.29469 (18)    0.3418 (2)     0.43510 (14)   0.0186 (6)           
  C13   0.15077 (18)    0.3582 (2)     0.33866 (14)   0.0176 (5)           
  C14   0.05499 (19)    0.3719 (2)     0.38076 (14)   0.0195 (6)           
  C15   −0.03509 (19)   0.4241 (2)     0.34434 (15)   0.0213 (6)           
  H15   −0.0974         0.4306         0.3741         0.026\*              
  C16   −0.03305 (19)   0.4674 (2)     0.26273 (15)   0.0208 (6)           
  C17   0.06207 (18)    0.4559 (2)     0.22035 (15)   0.0195 (6)           
  H17   0.0645          0.4862         0.1663         0.023\*              
  C18   0.15357 (18)    0.4010 (2)     0.25532 (14)   0.0169 (5)           
  C19   0.25352 (18)    0.3931 (2)     0.20691 (14)   0.0176 (5)           
  C20   0.31803 (19)    0.2884 (2)     0.20722 (14)   0.0211 (6)           
  H20   0.2982          0.2193         0.2372         0.025\*              
  C21   0.4119 (2)      0.2865 (3)     0.16287 (15)   0.0250 (6)           
  H21   0.4542          0.2160         0.1632         0.030\*              
  C22   0.4425 (2)      0.3883 (3)     0.11853 (15)   0.0265 (6)           
  H22   0.5062          0.3874         0.0902         0.032\*              
  C23   0.3783 (2)      0.4918 (3)     0.11635 (15)   0.0247 (6)           
  H23   0.3984          0.5603         0.0859         0.030\*              
  C24   0.28386 (19)    0.4937 (2)     0.15946 (14)   0.0209 (6)           
  H24   0.2403          0.5631         0.1566         0.025\*              
  C25   −0.1326 (2)     0.5199 (3)     0.22308 (17)   0.0258 (6)           
  C26   −0.2001 (2)     0.5956 (3)     0.26780 (18)   0.0335 (7)           
  H26   −0.1807         0.6176         0.3221         0.040\*              
  C27   −0.2959 (2)     0.6385 (3)     0.2324 (2)     0.0415 (8)           
  H27   −0.3399         0.6897         0.2625         0.050\*              
  C28   −0.3251 (2)     0.6047 (3)     0.1522 (2)     0.0447 (9)           
  H28   −0.3900         0.6316         0.1287         0.054\*              
  C29   −0.2592 (2)     0.5316 (3)     0.1070 (2)     0.0434 (9)           
  H29   −0.2794         0.5096         0.0529         0.052\*              
  C30   −0.1619 (2)     0.4899 (3)     0.14165 (18)   0.0338 (7)           
  H30   −0.1167         0.4420         0.1101         0.041\*              
  ----- --------------- -------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Cl1   0.0262 (3)    0.0333 (4)    0.0187 (3)    −0.0013 (3)    0.0026 (2)     0.0074 (3)
  O1    0.0344 (11)   0.0298 (12)   0.0354 (11)   0.0085 (10)    −0.0043 (8)    0.0040 (9)
  N2    0.0197 (10)   0.0197 (12)   0.0139 (10)   −0.0025 (10)   −0.0030 (8)    0.0026 (9)
  C1    0.0201 (12)   0.0284 (16)   0.0193 (13)   −0.0087 (13)   0.0024 (10)    −0.0033 (11)
  C2    0.0239 (13)   0.0242 (16)   0.0285 (14)   −0.0040 (13)   0.0047 (11)    −0.0062 (12)
  C3    0.0247 (14)   0.0299 (18)   0.0461 (18)   −0.0004 (14)   0.0070 (12)    −0.0112 (14)
  C4    0.0246 (14)   0.041 (2)     0.0352 (16)   −0.0075 (15)   0.0095 (12)    −0.0183 (14)
  C5    0.0208 (13)   0.0387 (19)   0.0235 (14)   −0.0099 (14)   0.0055 (11)    −0.0036 (13)
  C6    0.0295 (15)   0.050 (2)     0.0195 (14)   −0.0194 (16)   0.0031 (11)    −0.0103 (14)
  C7    0.0259 (15)   0.058 (2)     0.0209 (14)   −0.0123 (16)   −0.0051 (11)   0.0032 (14)
  C8    0.0264 (14)   0.048 (2)     0.0201 (13)   −0.0138 (15)   −0.0022 (10)   0.0100 (13)
  C9    0.0231 (13)   0.0350 (18)   0.0165 (12)   −0.0062 (14)   −0.0005 (10)   0.0046 (12)
  C10   0.0212 (13)   0.0396 (18)   0.0145 (12)   −0.0137 (14)   0.0059 (10)    −0.0023 (12)
  C11   0.0251 (14)   0.0293 (17)   0.0197 (13)   −0.0020 (14)   0.0009 (10)    0.0075 (12)
  C12   0.0188 (12)   0.0219 (15)   0.0150 (12)   −0.0035 (12)   0.0013 (9)     0.0020 (11)
  C13   0.0212 (12)   0.0141 (13)   0.0170 (12)   −0.0008 (11)   −0.0048 (9)    −0.0020 (10)
  C14   0.0250 (13)   0.0184 (15)   0.0150 (12)   −0.0048 (12)   −0.0005 (10)   0.0031 (10)
  C15   0.0174 (12)   0.0217 (15)   0.0248 (13)   −0.0032 (12)   0.0014 (10)    0.0031 (11)
  C16   0.0165 (12)   0.0186 (15)   0.0268 (14)   −0.0040 (12)   −0.0043 (10)   0.0020 (11)
  C17   0.0235 (13)   0.0180 (14)   0.0167 (12)   −0.0036 (12)   −0.0039 (10)   0.0014 (11)
  C18   0.0201 (12)   0.0135 (13)   0.0168 (12)   −0.0033 (11)   −0.0028 (9)    −0.0026 (10)
  C19   0.0186 (12)   0.0204 (14)   0.0134 (11)   −0.0007 (12)   −0.0050 (9)    −0.0044 (10)
  C20   0.0266 (13)   0.0191 (15)   0.0174 (12)   −0.0025 (12)   −0.0036 (10)   −0.0020 (11)
  C21   0.0273 (14)   0.0236 (16)   0.0239 (14)   0.0030 (13)    −0.0003 (11)   −0.0086 (12)
  C22   0.0242 (14)   0.0339 (18)   0.0218 (14)   −0.0070 (14)   0.0071 (11)    −0.0105 (12)
  C23   0.0313 (14)   0.0247 (16)   0.0183 (13)   −0.0079 (14)   0.0039 (10)    −0.0023 (11)
  C24   0.0269 (13)   0.0205 (15)   0.0151 (12)   −0.0011 (12)   −0.0037 (10)   −0.0019 (11)
  C25   0.0197 (13)   0.0257 (16)   0.0318 (15)   −0.0054 (13)   −0.0030 (11)   0.0104 (12)
  C26   0.0249 (14)   0.0405 (19)   0.0354 (16)   0.0011 (15)    0.0070 (12)    0.0145 (14)
  C27   0.0211 (14)   0.047 (2)     0.058 (2)     0.0073 (15)    0.0114 (14)    0.0223 (17)
  C28   0.0195 (14)   0.045 (2)     0.069 (2)     −0.0037 (16)   −0.0114 (15)   0.0275 (19)
  C29   0.0426 (18)   0.033 (2)     0.052 (2)     −0.0058 (17)   −0.0250 (15)   0.0092 (16)
  C30   0.0345 (16)   0.0253 (17)   0.0405 (17)   −0.0008 (15)   −0.0146 (13)   0.0026 (14)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ----------------------- ------------- ----------------------- -------------
  Cl1---C14               1.745 (2)     C15---C16               1.395 (3)
  O1---C11                1.223 (3)     C16---C17               1.394 (3)
  N2---C12                1.269 (3)     C16---C25               1.492 (3)
  N2---C13                1.412 (3)     C17---H17               0.9300
  C1---C2                 1.354 (4)     C17---C18               1.392 (3)
  C1---C10                1.433 (3)     C18---C19               1.495 (3)
  C1---C12                1.481 (4)     C19---C20               1.395 (3)
  C2---H2                 0.9300        C19---C24               1.393 (3)
  C2---C3                 1.420 (4)     C20---H20               0.9300
  C3---H3                 0.9300        C20---C21               1.392 (3)
  C3---C4                 1.385 (4)     C21---H21               0.9300
  C4---H4                 0.9300        C21---C22               1.378 (4)
  C4---C5                 1.389 (4)     C22---H22               0.9300
  C5---C6                 1.427 (4)     C22---C23               1.381 (4)
  C5---C10                1.411 (4)     C23---H23               0.9300
  C6---H6                 0.9300        C23---C24               1.388 (3)
  C6---C7                 1.366 (4)     C24---H24               0.9300
  C7---H7                 0.9300        C25---C26               1.394 (4)
  C7---C8                 1.407 (4)     C25---C30               1.387 (4)
  C8---H8                 0.9300        C26---H26               0.9300
  C8---C9                 1.387 (3)     C26---C27               1.389 (4)
  C9---C10                1.394 (4)     C27---H27               0.9300
  C9---C11                1.469 (4)     C27---C28               1.378 (5)
  C11---C12               1.550 (4)     C28---H28               0.9300
  C13---C14               1.402 (3)     C28---C29               1.370 (5)
  C13---C18               1.420 (3)     C29---H29               0.9300
  C14---C15               1.374 (3)     C29---C30               1.396 (4)
  C15---H15               0.9300        C30---H30               0.9300
                                                                
  C12---N2---C13          121.6 (2)     C15---C16---C25         119.4 (2)
  C2---C1---C10           120.5 (2)     C17---C16---C15         118.1 (2)
  C2---C1---C12           134.4 (2)     C17---C16---C25         122.5 (2)
  C10---C1---C12          105.1 (2)     C16---C17---H17         118.6
  C1---C2---H2            121.2         C18---C17---C16         122.9 (2)
  C1---C2---C3            117.5 (2)     C18---C17---H17         118.6
  C3---C2---H2            121.2         C13---C18---C19         121.3 (2)
  C2---C3---H3            118.7         C17---C18---C13         118.4 (2)
  C4---C3---C2            122.7 (3)     C17---C18---C19         120.2 (2)
  C4---C3---H3            118.7         C20---C19---C18         122.5 (2)
  C3---C4---H4            119.6         C24---C19---C18         119.1 (2)
  C3---C4---C5            120.7 (3)     C24---C19---C20         118.4 (2)
  C5---C4---H4            119.6         C19---C20---H20         119.8
  C4---C5---C6            128.3 (3)     C21---C20---C19         120.4 (2)
  C4---C5---C10           117.0 (2)     C21---C20---H20         119.8
  C10---C5---C6           114.8 (3)     C20---C21---H21         119.8
  C5---C6---H6            119.4         C22---C21---C20         120.4 (3)
  C7---C6---C5            121.3 (3)     C22---C21---H21         119.8
  C7---C6---H6            119.4         C21---C22---H22         120.1
  C6---C7---H7            118.4         C21---C22---C23         119.8 (2)
  C6---C7---C8            123.2 (3)     C23---C22---H22         120.1
  C8---C7---H7            118.4         C22---C23---H23         119.9
  C7---C8---H8            121.6         C22---C23---C24         120.2 (3)
  C9---C8---C7            116.8 (3)     C24---C23---H23         119.9
  C9---C8---H8            121.6         C19---C24---H24         119.6
  C8---C9---C10           120.5 (3)     C23---C24---C19         120.8 (3)
  C8---C9---C11           132.2 (3)     C23---C24---H24         119.6
  C10---C9---C11          107.2 (2)     C26---C25---C16         121.0 (2)
  C5---C10---C1           121.7 (3)     C30---C25---C16         120.3 (3)
  C9---C10---C1           114.8 (2)     C30---C25---C26         118.7 (3)
  C9---C10---C5           123.5 (2)     C25---C26---H26         119.5
  O1---C11---C9           129.4 (3)     C27---C26---C25         120.9 (3)
  O1---C11---C12          124.6 (2)     C27---C26---H26         119.5
  C9---C11---C12          106.0 (2)     C26---C27---H27         120.2
  N2---C12---C1           133.7 (2)     C28---C27---C26         119.5 (3)
  N2---C12---C11          119.5 (2)     C28---C27---H27         120.2
  C1---C12---C11          106.8 (2)     C27---C28---H28         119.8
  N2---C13---C18          120.7 (2)     C29---C28---C27         120.3 (3)
  C14---C13---N2          121.2 (2)     C29---C28---H28         119.8
  C14---C13---C18         117.9 (2)     C28---C29---H29         119.8
  C13---C14---Cl1         119.65 (18)   C28---C29---C30         120.5 (3)
  C15---C14---Cl1         117.78 (19)   C30---C29---H29         119.8
  C15---C14---C13         122.6 (2)     C25---C30---C29         120.0 (3)
  C14---C15---H15         120.0         C25---C30---H30         120.0
  C14---C15---C16         120.0 (2)     C29---C30---H30         120.0
  C16---C15---H15         120.0                                 
                                                                
  Cl1---C14---C15---C16   −179.6 (2)    C12---C1---C2---C3      −177.2 (3)
  O1---C11---C12---N2     2.8 (4)       C12---C1---C10---C5     178.9 (2)
  O1---C11---C12---C1     −177.2 (2)    C12---C1---C10---C9     0.9 (3)
  N2---C13---C14---Cl1    3.9 (3)       C13---N2---C12---C1     −3.7 (4)
  N2---C13---C14---C15    −174.9 (2)    C13---N2---C12---C11    176.2 (2)
  N2---C13---C18---C17    176.2 (2)     C13---C14---C15---C16   −0.8 (4)
  N2---C13---C18---C19    −6.6 (4)      C13---C18---C19---C20   44.1 (3)
  C1---C2---C3---C4       −1.8 (4)      C13---C18---C19---C24   −136.0 (2)
  C2---C1---C10---C5      0.7 (4)       C14---C13---C18---C17   1.0 (4)
  C2---C1---C10---C9      −177.3 (2)    C14---C13---C18---C19   178.2 (2)
  C2---C1---C12---N2      −4.2 (5)      C14---C15---C16---C17   0.0 (4)
  C2---C1---C12---C11     175.8 (3)     C14---C15---C16---C25   177.9 (2)
  C2---C3---C4---C5       2.3 (4)       C15---C16---C17---C18   1.4 (4)
  C3---C4---C5---C6       178.2 (3)     C15---C16---C25---C26   40.5 (4)
  C3---C4---C5---C10      −1.2 (4)      C15---C16---C25---C30   −136.8 (3)
  C4---C5---C6---C7       −177.9 (3)    C16---C17---C18---C13   −1.9 (4)
  C4---C5---C10---C1      −0.3 (4)      C16---C17---C18---C19   −179.1 (2)
  C4---C5---C10---C9      177.6 (2)     C16---C25---C26---C27   −176.2 (3)
  C5---C6---C7---C8       0.1 (4)       C16---C25---C30---C29   175.0 (3)
  C6---C5---C10---C1      −179.7 (2)    C17---C16---C25---C26   −141.7 (3)
  C6---C5---C10---C9      −1.9 (4)      C17---C16---C25---C30   41.0 (4)
  C6---C7---C8---C9       −1.4 (4)      C17---C18---C19---C20   −138.7 (2)
  C7---C8---C9---C10      1.1 (4)       C17---C18---C19---C24   41.2 (3)
  C7---C8---C9---C11      178.4 (3)     C18---C13---C14---Cl1   179.04 (18)
  C8---C9---C10---C1      178.6 (2)     C18---C13---C14---C15   0.3 (4)
  C8---C9---C10---C5      0.6 (4)       C18---C19---C20---C21   −178.3 (2)
  C8---C9---C11---O1      0.2 (5)       C18---C19---C24---C23   177.4 (2)
  C8---C9---C11---C12     −179.5 (3)    C19---C20---C21---C22   0.4 (4)
  C9---C11---C12---N2     −177.5 (2)    C20---C19---C24---C23   −2.7 (3)
  C9---C11---C12---C1     2.4 (2)       C20---C21---C22---C23   −1.7 (4)
  C10---C1---C2---C3      0.3 (4)       C21---C22---C23---C24   0.8 (4)
  C10---C1---C12---N2     178.0 (3)     C22---C23---C24---C19   1.4 (4)
  C10---C1---C12---C11    −2.0 (2)      C24---C19---C20---C21   1.8 (3)
  C10---C5---C6---C7      1.5 (4)       C25---C16---C17---C18   −176.4 (2)
  C10---C9---C11---O1     177.7 (3)     C25---C26---C27---C28   0.7 (4)
  C10---C9---C11---C12    −1.9 (3)      C26---C25---C30---C29   −2.3 (4)
  C11---C9---C10---C1     0.7 (3)       C26---C27---C28---C29   −1.5 (5)
  C11---C9---C10---C5     −177.3 (2)    C27---C28---C29---C30   0.4 (5)
  C12---N2---C13---C14    −72.0 (3)     C28---C29---C30---C25   1.6 (5)
  C12---N2---C13---C18    112.9 (3)     C30---C25---C26---C27   1.2 (4)
  ----------------------- ------------- ----------------------- -------------

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

Cg1 and Cg2 are the centroids of the C25--C30 and C19--C24 rings, respectively.

  ---------------------- --------- --------- ----------- ---------------
  *D*---H···*A*          *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C20---H20···N2         0.93      2.50      2.909 (3)   107
  C24---H24···N2^i^      0.93      2.59      3.338 (3)   138
  C4---H4···*Cg*1^ii^    0.93      2.74      3.551 (3)   147
  C6---H6···*Cg*2^iii^   0.93      2.92      3.647 (3)   136
  ---------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

*Cg*1 and *Cg*2 are the centroids of the C25--C30 and C19--C24 rings, respectively.

  *D*---H⋯*A*          *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  -------------------- --------- ------- ----------- -------------
  C24---H24⋯N2^i^      0.93      2.59    3.338 (3)   138
  C4---H4⋯*Cg*1^ii^    0.93      2.74    3.551 (3)   147
  C6---H6⋯*Cg*2^iii^   0.93      2.92    3.647 (3)   136

Symmetry codes: (i) ; (ii) ; (iii) .
