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

For the biological activity of the benzimidazole core, see: Horton *et al.* (2003[@bb2]). For the anti­protozoal activity of 2- and 5-substituted benzimidazoles, see: Navarrete-Vázquez *et al.* (2001[@bb3]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~30~H~26~N~4~O*M* *~r~* = 458.55Triclinic,*a* = 8.5477 (3) Å*b* = 11.8976 (5) Å*c* = 12.3961 (5) Åα = 101.300 (1)°β = 92.394 (1)°γ = 107.765 (1)°*V* = 1170.28 (8) Å^3^*Z* = 2Mo *K*α radiationμ = 0.08 mm^−1^*T* = 153 K0.58 × 0.52 × 0.19 mm

### Data collection {#sec2.1.2}

Rigaku R-AXIS Spider diffractometerAbsorption correction: multi-scan (*ABSCOR*; Higashi, 1995[@bb1]) *T* ~min~ = 0.955, *T* ~max~ = 0.98511531 measured reflections5275 independent reflections4542 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.013

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.038*wR*(*F* ^2^) = 0.126*S* = 1.095275 reflections317 parametersH-atom parameters constrainedΔρ~max~ = 0.50 e Å^−3^Δρ~min~ = −0.34 e Å^−3^

 {#d5e341}

Data collection: *RAPID-AUTO* (Rigaku/MSC, 2004[@bb4]); cell refinement: *RAPID-AUTO*; data reduction: *RAPID-AUTO*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb5]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb5]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb5]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536809012781/lh2800sup1.cif](http://dx.doi.org/10.1107/S1600536809012781/lh2800sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809012781/lh2800Isup2.hkl](http://dx.doi.org/10.1107/S1600536809012781/lh2800Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?lh2800&file=lh2800sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?lh2800sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?lh2800&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [LH2800](http://scripts.iucr.org/cgi-bin/sendsup?lh2800)).

The authors acknowledge financial support and a grant from the 'Qing Lan' Talent Engineering Funds and Students' Science and Technology Innovation Funds (grant No. DXS2008--040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25--023) and 'Long Yuan Qing Nian' of Gansu Province is also acknowledged.

Comment
=======

Benzimidazole derivatives, such as mebendazole and albendazole, are used as anthelmintic drugs. More recently, the antiprotozoal activity of 2- and 5-substituted benzimidazoles has been reported (Navarrete-Vázquez *et al.* 2001). The benzimidazole core is of interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton *et al.* 2003). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between N3/N4/C10-C16 and C18-C23 is 76.79 (12)° and that between N1/N2/C1-C7 and C25-C30 is 86.10 (11)°.

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

A solution of 5.56 (20 mmol) of 1,3-bis(benzimidazol-2-yl)-2-oxopropane with 1.56 g (40 mmol) potassium in 150 ml tetrahydrofuran followed by addition of 5.06 g (40 mmol) benzyl bromide was concentrated and recrystallized from methanol, formimg white block crystals suitable for X-ray diffraction studies. (found: C, 78.51; H, 5.73; N,12.24 Calcd. for C~30~H~26~N~4~O: C, 78.58; H, 5.71; N, 12.22)

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

All H atoms were positioned geometrically with C---H distances ranging from 0.95 to 0.99 Å and allowed to ride on their parent atoms with *U*~iso~(H) = 1.2 *U*~eq~ of the carrier atom.

Figures
=======

![Molecular structure of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.](e-65-o1014-fig1){#Fap1}

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

  ------------------------ ---------------------------------------
  C~30~H~26~N~4~O          *Z* = 2
  *M~r~* = 458.55          *F*(000) = 484
  Triclinic, *P*1          *D*~x~ = 1.301 Mg m^−3^
  Hall symbol: -P 1        Melting point = 450--451 K
  *a* = 8.5477 (3) Å       Mo *K*α radiation, λ = 0.71073 Å
  *b* = 11.8976 (5) Å      Cell parameters from 5275 reflections
  *c* = 12.3961 (5) Å      θ = 3.0--27.5°
  α = 101.300 (1)°         µ = 0.08 mm^−1^
  β = 92.394 (1)°          *T* = 153 K
  γ = 107.765 (1)°         Block, white
  *V* = 1170.28 (8) Å^3^   0.58 × 0.52 × 0.19 mm
  ------------------------ ---------------------------------------

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

  ------------------------------------------------------------- --------------------------------------
  Rigaku R-AXIS Spider diffractometer                           5275 independent reflections
  Radiation source: fine-focus sealed tube                      4542 reflections with *I* \> 2σ(*I*)
  graphite                                                      *R*~int~ = 0.013
  φ and ω scans                                                 θ~max~ = 27.5°, θ~min~ = 3.0°
  Absorption correction: multi-scan (*ABSCOR*; Higashi, 1995)   *h* = −11→10
  *T*~min~ = 0.955, *T*~max~ = 0.985                            *k* = −15→15
  11531 measured reflections                                    *l* = −16→16
  ------------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.038                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.126                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0736*P*)^2^ + 0.3041*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.09                                                       (Δ/σ)~max~ \< 0.001
  5275 reflections                                                 Δρ~max~ = 0.50 e Å^−3^
  317 parameters                                                   Δρ~min~ = −0.34 e Å^−3^
  0 restraints                                                     Extinction correction: *SHELXL*, Fc^\*^=kFc\[1+0.001xFc^2^λ^3^/sin(2θ)\]^-1/4^
  Primary atom site location: structure-invariant direct methods   Extinction coefficient: 0.044 (4)
  ---------------------------------------------------------------- -------------------------------------------------------------------------------------------------

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~   
  O      0.80479 (11)   0.49510 (8)     0.70677 (7)    0.0252 (2)           
  N1     0.73219 (13)   0.71312 (9)     0.90708 (8)    0.0233 (2)           
  N2     0.54296 (12)   0.52783 (9)     0.85764 (8)    0.0214 (2)           
  N3     0.99857 (12)   0.31236 (9)     0.79071 (8)    0.0231 (2)           
  N4     0.77779 (12)   0.22141 (9)     0.66368 (8)    0.0231 (2)           
  C1     0.58038 (15)   0.71864 (10)    0.93941 (9)    0.0213 (2)           
  C2     0.53783 (16)   0.81685 (11)    0.99680 (10)   0.0256 (3)           
  H2     0.6172         0.8953          1.0182         0.031\*              
  C3     0.37662 (17)   0.79594 (12)    1.02133 (10)   0.0276 (3)           
  H3     0.3451         0.8610          1.0611         0.033\*              
  C4     0.25816 (16)   0.68035 (12)    0.98864 (10)   0.0276 (3)           
  H4     0.1483         0.6695          1.0065         0.033\*              
  C5     0.29667 (15)   0.58181 (11)    0.93114 (10)   0.0247 (3)           
  H5     0.2164         0.5039          0.9086         0.030\*              
  C6     0.46015 (15)   0.60377 (10)    0.90831 (9)    0.0208 (2)           
  C7     0.70389 (15)   0.59876 (11)    0.85997 (9)    0.0217 (2)           
  C8     0.83822 (16)   0.55036 (12)    0.82143 (10)   0.0264 (3)           
  H8A    0.9446         0.6171          0.8349         0.032\*              
  H8B    0.8481         0.4902          0.8640         0.032\*              
  C9     0.92732 (15)   0.44005 (11)    0.67180 (10)   0.0258 (3)           
  H9A    1.0385         0.4975          0.7013         0.031\*              
  H9B    0.9208         0.4227          0.5900         0.031\*              
  C10    0.90483 (14)   0.32529 (11)    0.71040 (10)   0.0222 (2)           
  C11    0.79369 (14)   0.13374 (11)    0.71787 (9)    0.0221 (2)           
  C12    0.70094 (16)   0.01242 (12)    0.70590 (11)   0.0284 (3)           
  H12    0.6078         −0.0257         0.6520         0.034\*              
  C13    0.75138 (17)   −0.04945 (12)   0.77646 (11)   0.0295 (3)           
  H13    0.6919         −0.1325         0.7706         0.035\*              
  C14    0.88820 (17)   0.00726 (12)    0.85663 (11)   0.0283 (3)           
  H14    0.9187         −0.0382         0.9040         0.034\*              
  C15    0.98002 (15)   0.12805 (12)    0.86844 (10)   0.0258 (3)           
  H15    1.0722         0.1661          0.9231         0.031\*              
  C16    0.93194 (14)   0.19187 (10)    0.79690 (10)   0.0212 (2)           
  C17    0.64947 (15)   0.20654 (12)    0.57568 (10)   0.0257 (3)           
  H17A   0.6159         0.2803          0.5873         0.031\*              
  H17B   0.5516         0.1378          0.5808         0.031\*              
  C18    0.70267 (15)   0.18411 (11)    0.46087 (10)   0.0236 (3)           
  C19    0.66731 (18)   0.24654 (12)    0.38477 (11)   0.0312 (3)           
  H19    0.6115         0.3040          0.4057         0.037\*              
  C20    0.7125 (2)     0.22588 (14)    0.27833 (12)   0.0403 (4)           
  H20    0.6869         0.2686          0.2266         0.048\*              
  C21    0.7950 (2)     0.14290 (14)    0.24755 (12)   0.0393 (3)           
  H21    0.8275         0.1294          0.1750         0.047\*              
  C22    0.82983 (19)   0.07973 (13)    0.32288 (12)   0.0363 (3)           
  H22    0.8861         0.0225          0.3020         0.044\*              
  C23    0.78271 (17)   0.09980 (12)    0.42866 (11)   0.0303 (3)           
  H23    0.8055         0.0553          0.4797         0.036\*              
  C24    0.46863 (16)   0.39871 (10)    0.81196 (10)   0.0250 (3)           
  H24A   0.3901         0.3635          0.8622         0.030\*              
  H24B   0.5565         0.3603          0.8095         0.030\*              
  C25    0.37816 (14)   0.36798 (10)    0.69711 (10)   0.0214 (2)           
  C26    0.28424 (15)   0.24803 (12)    0.65272 (12)   0.0289 (3)           
  H26    0.2773         0.1885          0.6950         0.035\*              
  C27    0.20114 (18)   0.21494 (13)    0.54754 (13)   0.0383 (3)           
  H27    0.1383         0.1327          0.5179         0.046\*              
  C28    0.20876 (18)   0.30063 (14)    0.48511 (12)   0.0382 (3)           
  H28    0.1505         0.2778          0.4132         0.046\*              
  C29    0.30168 (19)   0.41940 (14)    0.52837 (12)   0.0352 (3)           
  H29    0.3079         0.4787          0.4859         0.042\*              
  C30    0.38665 (17)   0.45315 (12)    0.63410 (11)   0.0287 (3)           
  H30    0.4508         0.5352          0.6631         0.034\*              
  ------ -------------- --------------- -------------- -------------------- --

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

  ----- ------------ ------------ ------------ ------------ ------------- -------------
        *U*^11^      *U*^22^      *U*^33^      *U*^12^      *U*^13^       *U*^23^
  O     0.0294 (4)   0.0282 (4)   0.0204 (4)   0.0137 (4)   0.0023 (3)    0.0041 (3)
  N1    0.0256 (5)   0.0211 (5)   0.0220 (5)   0.0072 (4)   −0.0003 (4)   0.0032 (4)
  N2    0.0266 (5)   0.0177 (5)   0.0187 (5)   0.0064 (4)   −0.0011 (4)   0.0031 (4)
  N3    0.0228 (5)   0.0223 (5)   0.0224 (5)   0.0066 (4)   0.0023 (4)    0.0019 (4)
  N4    0.0236 (5)   0.0234 (5)   0.0208 (5)   0.0060 (4)   −0.0005 (4)   0.0043 (4)
  C1    0.0254 (6)   0.0206 (5)   0.0176 (5)   0.0066 (4)   0.0005 (4)    0.0051 (4)
  C2    0.0331 (6)   0.0207 (6)   0.0217 (6)   0.0085 (5)   0.0023 (5)    0.0023 (4)
  C3    0.0374 (7)   0.0288 (6)   0.0200 (6)   0.0159 (5)   0.0062 (5)    0.0044 (5)
  C4    0.0297 (6)   0.0346 (7)   0.0204 (6)   0.0120 (5)   0.0047 (5)    0.0075 (5)
  C5    0.0265 (6)   0.0262 (6)   0.0192 (5)   0.0046 (5)   0.0011 (4)    0.0060 (4)
  C6    0.0268 (6)   0.0208 (5)   0.0147 (5)   0.0072 (4)   0.0002 (4)    0.0045 (4)
  C7    0.0250 (6)   0.0221 (6)   0.0181 (5)   0.0079 (4)   −0.0011 (4)   0.0046 (4)
  C8    0.0286 (6)   0.0284 (6)   0.0225 (6)   0.0128 (5)   −0.0019 (5)   0.0015 (5)
  C9    0.0272 (6)   0.0257 (6)   0.0260 (6)   0.0094 (5)   0.0086 (5)    0.0065 (5)
  C10   0.0217 (5)   0.0223 (6)   0.0217 (5)   0.0071 (4)   0.0051 (4)    0.0021 (4)
  C11   0.0240 (6)   0.0232 (6)   0.0182 (5)   0.0071 (5)   0.0030 (4)    0.0034 (4)
  C12   0.0294 (6)   0.0251 (6)   0.0243 (6)   0.0019 (5)   −0.0017 (5)   0.0022 (5)
  C13   0.0358 (7)   0.0217 (6)   0.0281 (6)   0.0046 (5)   0.0050 (5)    0.0056 (5)
  C14   0.0343 (7)   0.0292 (6)   0.0253 (6)   0.0138 (5)   0.0050 (5)    0.0083 (5)
  C15   0.0256 (6)   0.0290 (6)   0.0224 (6)   0.0099 (5)   0.0003 (5)    0.0036 (5)
  C16   0.0209 (5)   0.0211 (5)   0.0201 (5)   0.0064 (4)   0.0040 (4)    0.0011 (4)
  C17   0.0225 (6)   0.0314 (6)   0.0229 (6)   0.0092 (5)   0.0002 (5)    0.0048 (5)
  C18   0.0225 (6)   0.0210 (5)   0.0230 (6)   0.0025 (4)   −0.0037 (4)   0.0030 (4)
  C19   0.0393 (7)   0.0268 (6)   0.0285 (6)   0.0122 (5)   −0.0017 (5)   0.0070 (5)
  C20   0.0543 (9)   0.0395 (8)   0.0271 (7)   0.0124 (7)   −0.0023 (6)   0.0127 (6)
  C21   0.0470 (8)   0.0395 (8)   0.0243 (6)   0.0057 (6)   0.0046 (6)    0.0036 (6)
  C22   0.0408 (8)   0.0321 (7)   0.0352 (7)   0.0125 (6)   0.0092 (6)    0.0032 (6)
  C23   0.0348 (7)   0.0297 (6)   0.0298 (7)   0.0132 (5)   0.0044 (5)    0.0096 (5)
  C24   0.0343 (6)   0.0171 (5)   0.0223 (6)   0.0064 (5)   0.0001 (5)    0.0048 (4)
  C25   0.0205 (5)   0.0211 (6)   0.0217 (6)   0.0071 (4)   0.0030 (4)    0.0019 (4)
  C26   0.0247 (6)   0.0222 (6)   0.0367 (7)   0.0056 (5)   0.0011 (5)    0.0027 (5)
  C27   0.0330 (7)   0.0272 (7)   0.0438 (8)   0.0053 (5)   −0.0093 (6)   −0.0076 (6)
  C28   0.0369 (7)   0.0422 (8)   0.0285 (7)   0.0121 (6)   −0.0081 (6)   −0.0050 (6)
  C29   0.0403 (7)   0.0370 (7)   0.0262 (7)   0.0099 (6)   −0.0040 (6)   0.0077 (6)
  C30   0.0337 (7)   0.0238 (6)   0.0245 (6)   0.0044 (5)   −0.0022 (5)   0.0046 (5)
  ----- ------------ ------------ ------------ ------------ ------------- -------------

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

  ---------------------- -------------- ----------------------- --------------
  O---C8                 1.4211 (14)    C13---H13               0.9500
  O---C9                 1.4350 (14)    C14---C15               1.3865 (18)
  N1---C7                1.3141 (15)    C14---H14               0.9500
  N1---C1                1.3907 (16)    C15---C16               1.3985 (17)
  N2---C7                1.3726 (15)    C15---H15               0.9500
  N2---C6                1.3846 (15)    C17---C18               1.5108 (17)
  N2---C24               1.4553 (14)    C17---H17A              0.9900
  N3---C10               1.3136 (16)    C17---H17B              0.9900
  N3---C16               1.3905 (15)    C18---C23               1.3850 (18)
  N4---C10               1.3748 (15)    C18---C19               1.3859 (18)
  N4---C11               1.3825 (15)    C19---C20               1.387 (2)
  N4---C17               1.4596 (15)    C19---H19               0.9500
  C1---C2                1.3996 (17)    C20---C21               1.384 (2)
  C1---C6                1.4056 (16)    C20---H20               0.9500
  C2---C3                1.3816 (18)    C21---C22               1.383 (2)
  C2---H2                0.9500         C21---H21               0.9500
  C3---C4                1.4065 (19)    C22---C23               1.385 (2)
  C3---H3                0.9500         C22---H22               0.9500
  C4---C5                1.3851 (18)    C23---H23               0.9500
  C4---H4                0.9500         C24---C25               1.5134 (16)
  C5---C6                1.3929 (17)    C24---H24A              0.9900
  C5---H5                0.9500         C24---H24B              0.9900
  C7---C8                1.4898 (17)    C25---C30               1.3828 (17)
  C8---H8A               0.9900         C25---C26               1.3930 (16)
  C8---H8B               0.9900         C26---C27               1.382 (2)
  C9---C10               1.4945 (17)    C26---H26               0.9500
  C9---H9A               0.9900         C27---C28               1.384 (2)
  C9---H9B               0.9900         C27---H27               0.9500
  C11---C12              1.3935 (17)    C28---C29               1.378 (2)
  C11---C16              1.4049 (16)    C28---H28               0.9500
  C12---C13              1.3811 (19)    C29---C30               1.3938 (18)
  C12---H12              0.9500         C29---H29               0.9500
  C13---C14              1.4033 (19)    C30---H30               0.9500
                                                                
  C8---O---C9            110.65 (9)     C13---C14---H14         119.2
  C7---N1---C1           104.47 (10)    C14---C15---C16         117.55 (11)
  C7---N2---C6           106.33 (9)     C14---C15---H15         121.2
  C7---N2---C24          128.47 (10)    C16---C15---H15         121.2
  C6---N2---C24          125.20 (10)    N3---C16---C15          130.02 (11)
  C10---N3---C16         104.83 (10)    N3---C16---C11          109.99 (10)
  C10---N4---C11         106.39 (10)    C15---C16---C11         119.97 (11)
  C10---N4---C17         127.05 (11)    N4---C17---C18          113.67 (10)
  C11---N4---C17         126.55 (10)    N4---C17---H17A         108.8
  N1---C1---C2           129.86 (11)    C18---C17---H17A        108.8
  N1---C1---C6           110.28 (10)    N4---C17---H17B         108.8
  C2---C1---C6           119.85 (11)    C18---C17---H17B        108.8
  C3---C2---C1           117.78 (11)    H17A---C17---H17B       107.7
  C3---C2---H2           121.1          C23---C18---C19         118.91 (12)
  C1---C2---H2           121.1          C23---C18---C17         121.38 (11)
  C2---C3---C4           121.34 (12)    C19---C18---C17         119.69 (11)
  C2---C3---H3           119.3          C18---C19---C20         120.65 (13)
  C4---C3---H3           119.3          C18---C19---H19         119.7
  C5---C4---C3           122.06 (12)    C20---C19---H19         119.7
  C5---C4---H4           119.0          C21---C20---C19         119.97 (13)
  C3---C4---H4           119.0          C21---C20---H20         120.0
  C4---C5---C6           116.01 (11)    C19---C20---H20         120.0
  C4---C5---H5           122.0          C22---C21---C20         119.69 (13)
  C6---C5---H5           122.0          C22---C21---H21         120.2
  N2---C6---C5           131.85 (11)    C20---C21---H21         120.2
  N2---C6---C1           105.17 (10)    C21---C22---C23         120.05 (14)
  C5---C6---C1           122.96 (11)    C21---C22---H22         120.0
  N1---C7---N2           113.75 (11)    C23---C22---H22         120.0
  N1---C7---C8           122.39 (11)    C18---C23---C22         120.71 (12)
  N2---C7---C8           123.68 (11)    C18---C23---H23         119.6
  O---C8---C7            110.75 (10)    C22---C23---H23         119.6
  O---C8---H8A           109.5          N2---C24---C25          114.13 (10)
  C7---C8---H8A          109.5          N2---C24---H24A         108.7
  O---C8---H8B           109.5          C25---C24---H24A        108.7
  C7---C8---H8B          109.5          N2---C24---H24B         108.7
  H8A---C8---H8B         108.1          C25---C24---H24B        108.7
  O---C9---C10           112.03 (10)    H24A---C24---H24B       107.6
  O---C9---H9A           109.2          C30---C25---C26         118.82 (11)
  C10---C9---H9A         109.2          C30---C25---C24         122.96 (11)
  O---C9---H9B           109.2          C26---C25---C24         118.21 (11)
  C10---C9---H9B         109.2          C27---C26---C25         120.48 (13)
  H9A---C9---H9B         107.9          C27---C26---H26         119.8
  N3---C10---N4          113.39 (11)    C25---C26---H26         119.8
  N3---C10---C9          125.14 (11)    C26---C27---C28         120.52 (13)
  N4---C10---C9          121.46 (11)    C26---C27---H27         119.7
  N4---C11---C12         131.98 (11)    C28---C27---H27         119.7
  N4---C11---C16         105.38 (10)    C29---C28---C27         119.31 (13)
  C12---C11---C16        122.64 (11)    C29---C28---H28         120.3
  C13---C12---C11        116.55 (11)    C27---C28---H28         120.3
  C13---C12---H12        121.7          C28---C29---C30         120.41 (13)
  C11---C12---H12        121.7          C28---C29---H29         119.8
  C12---C13---C14        121.68 (12)    C30---C29---H29         119.8
  C12---C13---H13        119.2          C25---C30---C29         120.44 (12)
  C14---C13---H13        119.2          C25---C30---H30         119.8
  C15---C14---C13        121.61 (12)    C29---C30---H30         119.8
  C15---C14---H14        119.2                                  
                                                                
  C7---N1---C1---C2      177.64 (12)    C17---N4---C11---C16    −178.40 (11)
  C7---N1---C1---C6      −0.91 (12)     N4---C11---C12---C13    −179.01 (13)
  N1---C1---C2---C3      −178.07 (12)   C16---C11---C12---C13   0.11 (19)
  C6---C1---C2---C3      0.35 (17)      C11---C12---C13---C14   0.5 (2)
  C1---C2---C3---C4      −0.82 (18)     C12---C13---C14---C15   −0.4 (2)
  C2---C3---C4---C5      0.42 (19)      C13---C14---C15---C16   −0.32 (19)
  C3---C4---C5---C6      0.47 (18)      C10---N3---C16---C15    −178.95 (12)
  C7---N2---C6---C5      −178.66 (12)   C10---N3---C16---C11    −0.61 (13)
  C24---N2---C6---C5     1.42 (19)      C14---C15---C16---N3    179.09 (12)
  C7---N2---C6---C1      −0.40 (12)     C14---C15---C16---C11   0.90 (17)
  C24---N2---C6---C1     179.68 (10)    N4---C11---C16---N3     −0.03 (13)
  C4---C5---C6---N2      177.04 (12)    C12---C11---C16---N3    −179.35 (11)
  C4---C5---C6---C1      −0.95 (17)     N4---C11---C16---C15    178.50 (10)
  N1---C1---C6---N2      0.82 (12)      C12---C11---C16---C15   −0.82 (18)
  C2---C1---C6---N2      −177.89 (10)   C10---N4---C17---C18    82.90 (15)
  N1---C1---C6---C5      179.27 (10)    C11---N4---C17---C18    −98.27 (14)
  C2---C1---C6---C5      0.56 (17)      N4---C17---C18---C23    47.20 (16)
  C1---N1---C7---N2      0.66 (13)      N4---C17---C18---C19    −134.51 (12)
  C1---N1---C7---C8      −174.66 (11)   C23---C18---C19---C20   −0.6 (2)
  C6---N2---C7---N1      −0.17 (13)     C17---C18---C19---C20   −178.91 (12)
  C24---N2---C7---N1     179.75 (11)    C18---C19---C20---C21   −0.5 (2)
  C6---N2---C7---C8      175.08 (10)    C19---C20---C21---C22   0.9 (2)
  C24---N2---C7---C8     −5.00 (18)     C20---C21---C22---C23   −0.2 (2)
  C9---O---C8---C7       −175.36 (10)   C19---C18---C23---C22   1.3 (2)
  N1---C7---C8---O       −122.70 (12)   C17---C18---C23---C22   179.60 (12)
  N2---C7---C8---O       62.45 (15)     C21---C22---C23---C18   −0.9 (2)
  C8---O---C9---C10      74.56 (13)     C7---N2---C24---C25     −98.23 (14)
  C16---N3---C10---N4    1.06 (13)      C6---N2---C24---C25     81.68 (14)
  C16---N3---C10---C9    −179.86 (11)   N2---C24---C25---C30    9.57 (17)
  C11---N4---C10---N3    −1.10 (14)     N2---C24---C25---C26    −171.39 (11)
  C17---N4---C10---N3    177.92 (11)    C30---C25---C26---C27   0.00 (19)
  C11---N4---C10---C9    179.78 (10)    C24---C25---C26---C27   −179.08 (12)
  C17---N4---C10---C9    −1.20 (18)     C25---C26---C27---C28   −0.6 (2)
  O---C9---C10---N3      −106.11 (13)   C26---C27---C28---C29   0.7 (2)
  O---C9---C10---N4      72.90 (14)     C27---C28---C29---C30   −0.3 (2)
  C10---N4---C11---C12   179.86 (13)    C26---C25---C30---C29   0.43 (19)
  C17---N4---C11---C12   0.8 (2)        C24---C25---C30---C29   179.46 (13)
  C10---N4---C11---C16   0.63 (13)      C28---C29---C30---C25   −0.3 (2)
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