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

For the synthesis of quinoxalines, see: Kowalski *et al.* (2006[@bb11]); Kou *et al.* (2006[@bb10]); Baek & Tan (2006[@bb3]). For applications of quinoxalines see: Mollegaard *et al.* (2000[@bb12]); Aldakov *et al.* (2005[@bb1]); Kaiwar *et al.* (1997[@bb9]); Anzenbacher *et al.* (2000[@bb2]). For related literature, see: Brown *et al.* (2004[@bb4]); Bruno *et al.* (2002[@bb6]); Gibson *et al.* (2006[@bb8]); Page *et al.* (1998[@bb13]); Pascal & Ho (1993[@bb14]); Salvatore *et al.* (2006[@bb15]); Simpson & Gordon (1995[@bb18]); Willett *et al.* (2001[@bb19]); Wozniak *et al.* (1993[@bb20]); Wu *et al.* (2002[@bb21]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~40~H~26~N~4~*M* *~r~* = 562.65Triclinic,*a* = 5.70240 (10) Å*b* = 9.9534 (2) Å*c* = 12.9785 (3) Åα = 105.3520 (10)°β = 96.6170 (10)°γ = 91.7510 (10)°*V* = 704.19 (3) Å^3^*Z* = 1Cu *K*α radiationμ = 0.61 mm^−1^*T* = 100 (2) K0.19 × 0.12 × 0.06 mm

### Data collection {#sec2.1.2}

Bruker SMART APEXII CCD diffractometerAbsorption correction: numerical (*SADABS*; Sheldrick, 2004[@bb17]) *T* ~min~ = 0.893, *T* ~max~ = 0.96412179 measured reflections2429 independent reflections2156 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.033

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.033*wR*(*F* ^2^) = 0.091*S* = 1.062429 reflections251 parametersAll H-atom parameters refinedΔρ~max~ = 0.23 e Å^−3^Δρ~min~ = −0.18 e Å^−3^

 {#d5e638}

Data collection: *APEX2* (Bruker, 2004[@bb5]); cell refinement: *SAINT-Plus* (Bruker, 2004[@bb5]); data reduction: *SAINT-Plus*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 1997[@bb16]); program(s) used to refine structure: *XSHELL* (Bruker, 2004[@bb5]); molecular graphics: *ORTEP-3* (Farrugia, 1997[@bb7]); software used to prepare material for publication: *SHELXL97* (Sheldrick, 1997[@bb16]).

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

Crystal structure: contains datablocks I, global, publication_text. DOI: [10.1107/S1600536807033521/gg2021sup1.cif](http://dx.doi.org/10.1107/S1600536807033521/gg2021sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536807033521/gg2021Isup2.hkl](http://dx.doi.org/10.1107/S1600536807033521/gg2021Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?gg2021&file=gg2021sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?gg2021sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?gg2021&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [GG2021](http://scripts.iucr.org/cgi-bin/sendsup?gg2021)).

EED acknowledges the National Science Foundation for primary support of this research (EPSCOR grant No. 450901). RDP is indebted to the NSF (CHE-0443345) and the College of William and Mary for the purchase of the X-ray diffractometer.

Comment
=======

Quinoxalines and their derivatives have received considerable attention in the past several years due to their electronic properties (Page *et al.*, 1998; Simpson & Gordon, 1995), H-bonding ability (Pascal *et al.*, 1993; Wozniak *et al.*, 1993), and their capacity to coordinate to metals forming interesting three-dimensional structures (Wu *et al.*, 2002; Willett *et al.*, 2001). During our investigations, we have prepared a number of substituted quinoxalines and phenazines, some of which coordinate to metal salts forming novel structures (Dueno, *et al.*, unpublished). Our current work involves the synthesis of new nitrogen heterocycles (Gibson, *et al.*, 2006; Salvatore, *et al.*, 2006) which may lead to novel three dimensional structures upon coordination to metal salts. Here, we report the crystal structure of 2,2\',3,3\'-Tetraphenyl-7,7\'-biquinoxaline (I), (Figure 1).

The structure of (I) has bond distances and angles that are unexceptional, as all fall within ranges found in the literature for similar nitrogen heterocycles (Brown *et al.*, 2004). The one molecule present in the asymmetric unit cell lies on an inversion center, so that half the molecule is related to its counterpart by symmetry (symmetry code, -*x*,-*y*,-*z*). As expected, the steric bulk of the phenyl substituents prevents them from being coplanar with the quinoxaline rings: the dihedral angle N2---C5---C15---C20 (phenyl ring 1) is 59.80 (11)°, and the dihedral angle N1---C4---C9---C10 (phenyl ring 2) is 25.98 (11)°. An interesting feature worth mentioning is that the two rings that make up the quinoxaline unit are not perfectly planar, for the angle between the N containing ring and the carbon-only ring is 3.50 (11)° (based on a least squares mean planes of N1---C4---C5---N2---C6---C3 and C1---C2---C3---C6---C7---C8). It is conceivable that this deviation from a planar structure is due to Van der Waals repulsion interactions between the aromatic substituents. Another interesting aspect of this molecule is that the packing diagram shows short contact interactions between phenyl substituents on one molecule and the quinoxaline ring of an adjacent molecule. Intermolecular distances range from 3.181 (2) Å (C10---C6) to 3.376 (2) Å (C11---C4), which suggests some degree of σ(CH)···π interaction (Figure 2).

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

A 50 ml round-bottomed flask was charged with biphenyl-3,3\',4,4\'-tetramine (214 mg, 1 mmol), benzil (420 mg, 2 mmol), iodine (51 mg, 0.2 mmol), and acetonitrile (15 ml). The reaction was monitored by thin-layer chromatography until complete consumption of the starting materials (15 min). The resulting amber solution was concentrated to dryness under reduced pressure. The dark-brown crude product was then subjected to flash column chromatography using silica gel (eluent: 9:1 hexane--EtOAc) in order to remove residual iodine. The pale-yellow solution was evaporated to dryness under reduced pressure to give (I) (yield 0.413 mg, 74%), as a white powder (m.p. 573 K). This powder was then crystallized from a minimal amount of toluene, and afforded (I) as pale-yellow cubes.

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

H atoms were placed in idealized positions (C---H = 0.96 -- 1.00 A) and allowed to ride on their parent atoms with *U*~iso~(H) = 1.2 *U*~eq~(C).

Figures
=======

![ORTEP (Farrugia, 1997) drawing of (I). Displacement ellipsoids have been drawn at the 50% probability level. Unlabeled atoms are related to labeled atoms by symmetry (code --x,-y,-z). H atoms have been omitted for clarity.](e-64-0o110-fig1){#Fap1}

![Mercury (Bruno et al., 2002) packing diagram of (I) along the b axis showing short contact interactions.](e-64-0o110-fig2){#Fap2}

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

  ----------------------- --------------------------------------
  C~40~H~26~N~4~          *Z* = 1
  *M~r~* = 562.65         *F*~000~ = 294
  Triclinic, *P*1         *D*~x~ = 1.327 Mg m^−3^
  Hall symbol: -P 1       Cu *K*α radiation λ = 1.54178 Å
  *a* = 5.70240 (10) Å    Cell parameters from 585 reflections
  *b* = 9.9534 (2) Å      θ = 3.6--67.0º
  *c* = 12.9785 (3) Å     µ = 0.61 mm^−1^
  α = 105.3520 (10)º      *T* = 100 (2) K
  β = 96.6170 (10)º       Block, colourless
  γ = 91.7510 (10)º       0.19 × 0.12 × 0.06 mm
  *V* = 704.19 (3) Å^3^   
  ----------------------- --------------------------------------

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

  ----------------------------------------------------------- --------------------------------------
  Bruker SMART APEXII CCD diffractometer                      2429 independent reflections
  Radiation source: fine-focus sealed tube                    2156 reflections with *I* \> 2σ(*I*)
  Monochromator: graphite                                     *R*~int~ = 0.033
  *T* = 100(2) K                                              θ~max~ = 67.0º
  ω and ψ scans                                               θ~min~ = 3.6º
  Absorption correction: numerical(SADABS; Sheldrick, 2004)   *h* = −6→6
  *T*~min~ = 0.893, *T*~max~ = 0.964                          *k* = −11→11
  12179 measured reflections                                  *l* = −15→15
  ----------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.033                              All H-atom parameters refined
  *wR*(*F*^2^) = 0.091                                               *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0496*P*)^2^ + 0.1323*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.06                                                       (Δ/σ)~max~ \< 0.001
  2429 reflections                                                 Δρ~max~ = 0.23 e Å^−3^
  251 parameters                                                   Δρ~min~ = −0.18 e Å^−3^
  Primary atom site location: structure-invariant direct methods   Extinction correction: none
  ---------------------------------------------------------------- ---------------------------------------------------------------------------------------------------

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~   
  N1    0.51854 (16)   0.85128 (10)   0.69940 (8)    0.0221 (2)           
  N2    0.23046 (17)   0.60236 (10)   0.64109 (8)    0.0224 (2)           
  C1    0.03603 (19)   0.94087 (11)   0.52202 (9)    0.0209 (3)           
  C2    0.2496 (2)     0.94755 (12)   0.58600 (9)    0.0226 (3)           
  C3    0.31629 (19)   0.83612 (11)   0.62942 (9)    0.0211 (3)           
  C4    0.57593 (19)   0.74558 (12)   0.73939 (9)    0.0212 (3)           
  C5    0.43238 (19)   0.61520 (12)   0.70434 (9)    0.0211 (3)           
  C6    0.1661 (2)     0.71321 (12)   0.60385 (9)    0.0217 (3)           
  C7    −0.0511 (2)    0.70597 (12)   0.53726 (9)    0.0231 (3)           
  C8    −0.1142 (2)    0.81609 (12)   0.49890 (9)    0.0225 (3)           
  C9    0.79004 (19)   0.77207 (11)   0.82117 (9)    0.0219 (3)           
  C10   0.9637 (2)     0.87320 (12)   0.81830 (10)   0.0239 (3)           
  C11   1.1675 (2)     0.90121 (13)   0.89186 (10)   0.0269 (3)           
  C12   1.2013 (2)     0.82934 (13)   0.97005 (10)   0.0288 (3)           
  C13   1.0272 (2)     0.73173 (13)   0.97578 (10)   0.0281 (3)           
  C14   0.8232 (2)     0.70364 (12)   0.90232 (10)   0.0252 (3)           
  C15   0.49998 (19)   0.48375 (11)   0.73197 (9)    0.0215 (3)           
  C16   0.7014 (2)     0.41920 (12)   0.69865 (9)    0.0240 (3)           
  C17   0.7507 (2)     0.29096 (12)   0.71734 (10)   0.0248 (3)           
  C18   0.6025 (2)     0.22840 (12)   0.77110 (9)    0.0244 (3)           
  C19   0.4035 (2)     0.29355 (13)   0.80581 (10)   0.0268 (3)           
  C20   0.3503 (2)     0.42037 (12)   0.78536 (10)   0.0247 (3)           
  H2    0.361 (3)      1.0290 (16)    0.6039 (12)    0.035 (4)\*          
  H7    −0.153 (3)     0.6200 (16)    0.5199 (12)    0.035 (4)\*          
  H8    −0.267 (2)     0.8096 (13)    0.4535 (11)    0.021 (3)\*          
  H10   0.938 (2)      0.9233 (14)    0.7633 (11)    0.026 (3)\*          
  H11   1.287 (3)      0.9694 (15)    0.8870 (12)    0.033 (4)\*          
  H12   1.344 (3)      0.8484 (16)    1.0224 (12)    0.036 (4)\*          
  H13   1.048 (2)      0.6786 (16)    1.0312 (13)    0.037 (4)\*          
  H14   0.698 (3)      0.6366 (16)    0.9090 (12)    0.033 (4)\*          
  H16   0.807 (2)      0.4646 (15)    0.6621 (12)    0.029 (3)\*          
  H17   0.888 (2)      0.2451 (14)    0.6924 (11)    0.023 (3)\*          
  H18   0.640 (2)      0.1387 (15)    0.7834 (11)    0.028 (3)\*          
  H19   0.296 (2)      0.2499 (15)    0.8440 (12)    0.033 (4)\*          
  H20   0.210 (3)      0.4660 (15)    0.8084 (12)    0.032 (4)\*          
  ----- -------------- -------------- -------------- -------------------- --

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

  ----- ------------ ------------ ------------ ------------- ------------- ------------
        *U*^11^      *U*^22^      *U*^33^      *U*^12^       *U*^13^       *U*^23^
  N1    0.0212 (5)   0.0209 (5)   0.0245 (5)   0.0010 (4)    0.0015 (4)    0.0073 (4)
  N2    0.0241 (5)   0.0195 (5)   0.0240 (5)   0.0010 (4)    0.0019 (4)    0.0070 (4)
  C1    0.0227 (6)   0.0196 (6)   0.0205 (6)   0.0010 (5)    0.0037 (4)    0.0052 (4)
  C2    0.0228 (6)   0.0193 (6)   0.0258 (6)   −0.0015 (5)   0.0015 (4)    0.0073 (5)
  C3    0.0204 (6)   0.0208 (6)   0.0216 (6)   0.0006 (5)    0.0027 (4)    0.0049 (4)
  C4    0.0219 (6)   0.0196 (5)   0.0231 (6)   0.0019 (4)    0.0047 (4)    0.0067 (4)
  C5    0.0204 (5)   0.0208 (6)   0.0224 (6)   0.0010 (4)    0.0035 (4)    0.0060 (4)
  C6    0.0243 (6)   0.0189 (5)   0.0217 (6)   0.0012 (5)    0.0038 (4)    0.0051 (4)
  C7    0.0238 (6)   0.0199 (6)   0.0244 (6)   −0.0024 (5)   0.0005 (4)    0.0053 (4)
  C8    0.0224 (6)   0.0217 (6)   0.0227 (6)   −0.0013 (5)   0.0003 (4)    0.0058 (4)
  C9    0.0207 (6)   0.0187 (5)   0.0249 (6)   0.0033 (4)    0.0025 (4)    0.0034 (4)
  C10   0.0247 (6)   0.0207 (6)   0.0260 (6)   0.0034 (5)    0.0037 (5)    0.0057 (5)
  C11   0.0227 (6)   0.0256 (6)   0.0302 (7)   −0.0002 (5)   0.0041 (5)    0.0036 (5)
  C12   0.0224 (6)   0.0343 (7)   0.0261 (6)   0.0014 (5)    −0.0025 (5)   0.0042 (5)
  C13   0.0279 (6)   0.0295 (6)   0.0270 (6)   0.0038 (5)    0.0002 (5)    0.0087 (5)
  C14   0.0248 (6)   0.0235 (6)   0.0262 (6)   0.0008 (5)    0.0015 (5)    0.0058 (5)
  C15   0.0218 (6)   0.0185 (5)   0.0225 (6)   −0.0011 (4)   −0.0023 (4)   0.0050 (4)
  C16   0.0240 (6)   0.0229 (6)   0.0258 (6)   0.0002 (5)    0.0034 (5)    0.0077 (5)
  C17   0.0238 (6)   0.0225 (6)   0.0264 (6)   0.0041 (5)    0.0008 (5)    0.0045 (5)
  C18   0.0285 (6)   0.0180 (5)   0.0253 (6)   0.0009 (5)    −0.0048 (5)   0.0069 (4)
  C19   0.0260 (6)   0.0259 (6)   0.0310 (7)   −0.0011 (5)   0.0017 (5)    0.0131 (5)
  C20   0.0206 (6)   0.0248 (6)   0.0296 (6)   0.0023 (5)    0.0030 (5)    0.0089 (5)
  ----- ------------ ------------ ------------ ------------- ------------- ------------

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

  ---------------------- -------------- ----------------------- --------------
  N1---C4                1.3245 (15)    C10---H10               0.974 (14)
  N1---C3                1.3613 (14)    C11---C12               1.3880 (18)
  N2---C5                1.3166 (15)    C11---H11               0.966 (15)
  N2---C6                1.3609 (15)    C12---C13               1.3899 (18)
  C1---C2                1.3819 (16)    C12---H12               0.978 (15)
  C1---C8                1.4301 (16)    C13---C14               1.3870 (17)
  C1---C1^i^             1.488 (2)      C13---H13               0.998 (15)
  C2---C3                1.4141 (16)    C14---H14               0.988 (15)
  C2---H2                0.976 (15)     C15---C16               1.3898 (17)
  C3---C6                1.4129 (16)    C15---C20               1.3936 (16)
  C4---C5                1.4484 (16)    C16---C17               1.3918 (16)
  C4---C9                1.4900 (15)    C16---H16               0.976 (14)
  C5---C15               1.4955 (15)    C17---C18               1.3865 (17)
  C6---C7                1.4143 (16)    C17---H17               0.962 (14)
  C7---C8                1.3604 (16)    C18---C19               1.3852 (18)
  C7---H7                0.977 (15)     C18---H18               0.973 (14)
  C8---H8                0.986 (13)     C19---C20               1.3922 (16)
  C9---C14               1.3967 (17)    C19---H19               0.990 (15)
  C9---C10               1.4010 (16)    C20---H20               0.971 (15)
  C10---C11              1.3868 (17)                            
                                                                
  C4---N1---C3           118.29 (10)    C9---C10---H10          118.5 (8)
  C5---N2---C6           117.97 (10)    C12---C11---C10         120.12 (11)
  C2---C1---C8           117.90 (10)    C12---C11---H11         120.4 (8)
  C2---C1---C1^i^        121.33 (13)    C10---C11---H11         119.4 (8)
  C8---C1---C1^i^        120.76 (12)    C11---C12---C13         119.59 (11)
  C1---C2---C3           121.34 (11)    C11---C12---H12         120.8 (9)
  C1---C2---H2           122.0 (8)      C13---C12---H12         119.6 (9)
  C3---C2---H2           116.6 (9)      C14---C13---C12         120.35 (11)
  N1---C3---C6           120.83 (10)    C14---C13---H13         118.8 (9)
  N1---C3---C2           119.57 (10)    C12---C13---H13         120.9 (9)
  C6---C3---C2           119.52 (10)    C13---C14---C9          120.67 (11)
  N1---C4---C5           120.22 (10)    C13---C14---H14         119.5 (8)
  N1---C4---C9           115.70 (10)    C9---C14---H14          119.8 (8)
  C5---C4---C9           124.07 (10)    C16---C15---C20         119.65 (10)
  N2---C5---C4           121.55 (10)    C16---C15---C5          120.82 (10)
  N2---C5---C15          114.09 (10)    C20---C15---C5          119.38 (10)
  C4---C5---C15          124.33 (10)    C15---C16---C17         119.93 (11)
  N2---C6---C3           120.68 (10)    C15---C16---H16         119.3 (8)
  N2---C6---C7           120.32 (10)    C17---C16---H16         120.8 (8)
  C3---C6---C7           118.99 (10)    C18---C17---C16         120.38 (11)
  C8---C7---C6           120.36 (11)    C18---C17---H17         119.8 (8)
  C8---C7---H7           121.6 (9)      C16---C17---H17         119.8 (8)
  C6---C7---H7           118.1 (9)      C19---C18---C17         119.78 (11)
  C7---C8---C1           121.85 (11)    C19---C18---H18         121.0 (8)
  C7---C8---H8           119.2 (7)      C17---C18---H18         119.2 (8)
  C1---C8---H8           119.0 (7)      C18---C19---C20         120.18 (11)
  C14---C9---C10         118.36 (11)    C18---C19---H19         120.6 (8)
  C14---C9---C4          123.20 (10)    C20---C19---H19         119.2 (8)
  C10---C9---C4          118.42 (10)    C15---C20---C19         120.05 (11)
  C11---C10---C9         120.85 (11)    C15---C20---H20         119.3 (8)
  C11---C10---H10        120.7 (8)      C19---C20---H20         120.7 (8)
                                                                
  C8---C1---C2---C3      −1.34 (17)     N1---C4---C9---C14      152.27 (11)
  C1^i^---C1---C2---C3   178.88 (12)    C5---C4---C9---C14      −26.95 (17)
  C4---N1---C3---C6      2.79 (16)      N1---C4---C9---C10      −25.98 (15)
  C4---N1---C3---C2      179.56 (10)    C5---C4---C9---C10      154.81 (11)
  C1---C2---C3---N1      −174.44 (10)   C14---C9---C10---C11    2.26 (17)
  C1---C2---C3---C6      2.37 (17)      C4---C9---C10---C11     −179.41 (10)
  C3---N1---C4---C5      3.29 (16)      C9---C10---C11---C12    −0.35 (18)
  C3---N1---C4---C9      −175.95 (9)    C10---C11---C12---C13   −1.57 (19)
  C6---N2---C5---C4      3.88 (16)      C11---C12---C13---C14   1.55 (19)
  C6---N2---C5---C15     −174.05 (9)    C12---C13---C14---C9    0.41 (18)
  N1---C4---C5---N2      −6.97 (17)     C10---C9---C14---C13    −2.28 (17)
  C9---C4---C5---N2      172.21 (10)    C4---C9---C14---C13     179.47 (10)
  N1---C4---C5---C15     170.75 (10)    N2---C5---C15---C16     115.78 (12)
  C9---C4---C5---C15     −10.07 (17)    C4---C5---C15---C16     −62.09 (15)
  C5---N2---C6---C3      2.27 (16)      N2---C5---C15---C20     −59.79 (14)
  C5---N2---C6---C7      −178.84 (10)   C4---C5---C15---C20     122.33 (12)
  N1---C3---C6---N2      −5.86 (17)     C20---C15---C16---C17   0.92 (17)
  C2---C3---C6---N2      177.37 (10)    C5---C15---C16---C17    −174.64 (10)
  N1---C3---C6---C7      175.23 (10)    C15---C16---C17---C18   −1.36 (18)
  C2---C3---C6---C7      −1.54 (16)     C16---C17---C18---C19   0.39 (17)
  N2---C6---C7---C8      −179.17 (10)   C17---C18---C19---C20   1.01 (18)
  C3---C6---C7---C8      −0.26 (17)     C16---C15---C20---C19   0.46 (18)
  C6---C7---C8---C1      1.31 (18)      C5---C15---C20---C19    176.09 (10)
  C2---C1---C8---C7      −0.51 (17)     C18---C19---C20---C15   −1.44 (18)
  C1^i^---C1---C8---C7   179.27 (13)                            
  ---------------------- -------------- ----------------------- --------------

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

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

  --------------------- ------------ ------------ ------------- ---------------
  *D*---H···*A*         *D*---H      H···*A*      *D*···*A*     *D*---H···*A*
  C2---H2···C18^ii^     0.977 (15)   2.722 (15)   3.5521 (16)   143.1 (12)
  C7---H7···N2^iii^     0.979 (15)   2.593 (16)   3.3635 (15)   135.6 (11)
  C10---H10···C3^iv^    0.974 (13)   2.935 (12)   3.2994 (15)   103.4 (8)
  C10---H10···C6^iv^    0.974 (13)   2.974 (13)   3.1801 (15)   93.1 (8)
  C11---H11···N1^iv^    0.963 (15)   2.893 (14)   3.3233 (14)   108.3 (10)
  C12---H12···C18^v^    0.975 (15)   2.959 (15)   3.6146 (16)   125.6 (10)
  C13---H13···C18^v^    0.999 (15)   2.978 (15)   3.6141 (16)   122.5 (10)
  C16---H16···N2^iv^    0.978 (14)   2.815 (14)   3.7256 (14)   155.2 (11)
  C17---H17···C1^vi^    0.969 (13)   2.993 (14)   3.7019 (16)   131.0 (9)
  C17---H17···C8^vi^    0.969 (13)   2.860 (14)   3.6338 (15)   137.5 (9)
  C18---H18···N1^vii^   0.975 (14)   2.808 (14)   3.6217 (14)   141.5 (10)
  --------------------- ------------ ------------ ------------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H      H⋯*A*        *D*⋯*A*       *D*---H⋯*A*
  ------------------- ------------ ------------ ------------- -------------
  C2---H2⋯C18^i^      0.977 (15)   2.722 (15)   3.5521 (16)   143.1 (12)
  C7---H7⋯N2^ii^      0.979 (15)   2.593 (16)   3.3635 (15)   135.6 (11)
  C10---H10⋯C3^iii^   0.974 (13)   2.935 (12)   3.2994 (15)   103.4 (8)
  C10---H10⋯C6^iii^   0.974 (13)   2.974 (13)   3.1801 (15)   93.1 (8)
  C11---H11⋯N1^iii^   0.963 (15)   2.893 (14)   3.3233 (14)   108.3 (10)
  C12---H12⋯C18^iv^   0.975 (15)   2.959 (15)   3.6146 (16)   125.6 (10)
  C13---H13⋯C18^iv^   0.999 (15)   2.978 (15)   3.6141 (16)   122.5 (10)
  C16---H16⋯N2^iii^   0.978 (14)   2.815 (14)   3.7256 (14)   155.2 (11)
  C17---H17⋯C1^v^     0.969 (13)   2.993 (14)   3.7019 (16)   131.0 (9)
  C17---H17⋯C8^v^     0.969 (13)   2.860 (14)   3.6338 (15)   137.5 (9)
  C18---H18⋯N1^vi^    0.975 (14)   2.808 (14)   3.6217 (14)   141.5 (10)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .
