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

For a related structure, see: Stilinovic *et al.* (2008[@bb5]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~19~H~22~N~2~O*M* *~r~* = 294.39Monoclinic,*a* = 10.603 (2) Å*b* = 9.6330 (19) Å*c* = 32.595 (7) Åβ = 95.60 (3)°*V* = 3313.3 (11) Å^3^*Z* = 8Mo *K*α radiationμ = 0.07 mm^−1^*T* = 293 K0.40 × 0.40 × 0.20 mm

### Data collection {#sec2.1.2}

Enraf--Nonius CAD-4 diffractometerAbsorption correction: ψ scan (North *et al.*, 1968[@bb3]) *T* ~min~ = 0.971, *T* ~max~ = 0.9866837 measured reflections6473 independent reflections2764 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.1173 standard reflections every 200 reflections intensity decay: 1%

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.082*wR*(*F* ^2^) = 0.268*S* = 1.096473 reflections406 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.22 e Å^−3^Δρ~min~ = −0.20 e Å^−3^

 {#d5e425}

Data collection: *CAD-4 Software* (Enraf--Nonius, 1989[@bb1]); cell refinement: *CAD-4 Software*; data reduction: *XCAD4* (Harms & Wocadlo, 1995[@bb2]); program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb4]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb4]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb4]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S160053681105197X/hb6532sup1.cif](http://dx.doi.org/10.1107/S160053681105197X/hb6532sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S160053681105197X/hb6532Isup2.hkl](http://dx.doi.org/10.1107/S160053681105197X/hb6532Isup2.hkl)

Supplementary material file. DOI: [10.1107/S160053681105197X/hb6532Isup3.cdx](http://dx.doi.org/10.1107/S160053681105197X/hb6532Isup3.cdx)

Supplementary material file. DOI: [10.1107/S160053681105197X/hb6532Isup4.cml](http://dx.doi.org/10.1107/S160053681105197X/hb6532Isup4.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?hb6532&file=hb6532sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?hb6532sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?hb6532&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [HB6532](http://scripts.iucr.org/cgi-bin/sendsup?hb6532)).

We are grateful to the China Postdoctoral Science Foundation (20110491380) and the Fundamental Research Funds for the Central Universities (ZYGX2009J085) for support.

Comment
=======

The cystal structure of 1,4-bis-((1-benzylpiperidin-4-ylimino)methyl)benzene has been reported, which was synthesized by 4-amino-*N*-benzylpiperidine and terephtaldialdehyde. (Stilinovic *et al.*, 2008). While, the title compund has been obtained by 4-amino-*N*-benzylpiperidine and salicyaldehyde. The molecular structure of title compound (I) with atom numbering are given in is shown in Fig. 1, there are two (*E*)-2-((1-benzylpiperidin-4-ylimino)methyl)phenol in an asymmetric unit. Both C7=N1 and C26=N3 are of the E configuration, with the bond lengths of 1.262 (6) and 1.267 (6) Å. The torsion angle of C9---C8---N1---C7 and C28---C27---N3---C26 is -118.2 (5) ° and 107.9 (5) °, respectively. The Rms of two six-member piperidine rings of chair conformation are 0.2354 Å and 0.2322 Å. The dihedral angles between two phenyl planes in two molecules are 45.97 (18) and 65.97 (21)°. In each molecule, intramolecular O---H···N hydrogen bonds occur, and molecules are linked through intermolecular O---H···O hydrogen bonds to form a packing network along *b* axis.(Fig. 2).

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

The title compound was prepared by stirring a mixture of salicylaldehyde (122 mg, 1 mmol) and 4-amino-*N*-benzylpiperidine (190 mg, 1 mmol) in methanol (15 ml) for 4 h at room temperature. After keeping the solution in air for 3 d, yellow block-shaped crystals of (I) were formed. The crystals were isolated, washed three times with methanol and dried in a vacuum desiccator containing anhydrous CaCl~2~.

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

All the H atoms, were placed in idealized positions (C---H = 0.93- 0.96 Å, O---H = 0.82 Å) and refined as riding with *U*~iso~(H) = 1.2*U*~eq~(C) and *U*~iso~(H) = 1.5*U*~eq~(O).

Figures
=======

![The structure of (I) showing 35% probability displacement ellipsoids.](e-68-00o85-fig1){#Fap1}

![The crystal packing of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.](e-68-00o85-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~19~H~22~N~2~O           *F*(000) = 1264
  *M~r~* = 294.39           *D*~x~ = 1.180 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 2318 reflections
  *a* = 10.603 (2) Å        θ = 2.6--24.7°
  *b* = 9.6330 (19) Å       µ = 0.07 mm^−1^
  *c* = 32.595 (7) Å        *T* = 293 K
  β = 95.60 (3)°            Block, yellow
  *V* = 3313.3 (11) Å^3^    0.40 × 0.40 × 0.20 mm
  *Z* = 8                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------ ----------------------------------------------
  Enraf--Nonius CAD-4 diffractometer                     2764 reflections with *I* \> 2σ(*I*)
  Radiation source: fine-focus sealed tube               *R*~int~ = 0.117
  graphite                                               θ~max~ = 26.0°, θ~min~ = 1.3°
  ω/2θ scan                                              *h* = 0→13
  Absorption correction: ψ scan (North *et al.*, 1968)   *k* = 0→11
  *T*~min~ = 0.971, *T*~max~ = 0.986                     *l* = −40→39
  6837 measured reflections                              3 standard reflections every 200 reflections
  6473 independent reflections                           intensity decay: 1%
  ------------------------------------------------------ ----------------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.082                              H atoms treated by a mixture of independent and constrained refinement
  *wR*(*F*^2^) = 0.268                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0628*P*)^2^ + 4.8871*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.09                                                       (Δ/σ)~max~ \< 0.001
  6473 reflections                                                 Δρ~max~ = 0.22 e Å^−3^
  406 parameters                                                   Δρ~min~ = −0.20 e Å^−3^
  0 restraints                                                     Extinction correction: *SHELXL97* (Sheldrick, 2008), Fc^\*^=kFc\[1+0.001xFc^2^λ^3^/sin(2θ)\]^-1/4^
  Primary atom site location: structure-invariant direct methods   Extinction coefficient: 0.0089 (11)
  ---------------------------------------------------------------- ----------------------------------------------------------------------------------------------------

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~   
  C1     0.3352 (5)    0.6495 (5)    1.08004 (15)   0.0556 (13)          
  C2     0.3051 (6)    0.6876 (5)    1.11893 (17)   0.0748 (16)          
  H2     0.2226        0.7148        1.1223         0.090\*              
  C3     0.3932 (8)    0.6864 (6)    1.15252 (19)   0.088 (2)            
  H3     0.3714        0.7136        1.1783         0.106\*              
  C4     0.5159 (7)    0.6437 (6)    1.14746 (18)   0.0829 (18)          
  H4     0.5767        0.6431        1.1700         0.099\*              
  C5     0.5483 (5)    0.6028 (6)    1.10994 (16)   0.0698 (15)          
  H5     0.6304        0.5726        1.1072         0.084\*              
  C6     0.4601 (5)    0.6057 (5)    1.07583 (15)   0.0581 (13)          
  C7     0.2416 (5)    0.6562 (5)    1.04446 (17)   0.0576 (13)          
  H7     0.1604        0.6872        1.0482         0.069\*              
  C8     0.1693 (5)    0.6312 (5)    0.97399 (15)   0.0566 (13)          
  H8     0.0912        0.6681        0.9836         0.068\*              
  C9     0.1432 (5)    0.4880 (5)    0.95584 (16)   0.0632 (14)          
  H9A    0.2228        0.4443        0.9510         0.076\*              
  H9B    0.1031        0.4313        0.9755         0.076\*              
  C10    0.0583 (5)    0.4942 (5)    0.91573 (16)   0.0672 (15)          
  H10A   0.0483        0.4015        0.9043         0.081\*              
  H10B   −0.0248       0.5275        0.9212         0.081\*              
  C11    0.1222 (5)    0.7256 (5)    0.90270 (16)   0.0621 (14)          
  H11A   0.0398        0.7586        0.9090         0.075\*              
  H11B   0.1527        0.7876        0.8824         0.075\*              
  C12    0.2130 (5)    0.7276 (5)    0.94143 (15)   0.0601 (14)          
  H12A   0.2195        0.8214        0.9522         0.072\*              
  H12B   0.2965        0.6993        0.9348         0.072\*              
  C13    0.0265 (5)    0.5833 (6)    0.84734 (17)   0.0780 (17)          
  H13A   −0.0563       0.6171        0.8529         0.094\*              
  H13B   0.0164        0.4879        0.8381         0.094\*              
  C14    0.0717 (5)    0.6680 (6)    0.81311 (17)   0.0674 (15)          
  C15    −0.0101 (6)   0.7503 (7)    0.7894 (2)     0.094 (2)            
  H15    −0.0943       0.7548        0.7950         0.113\*              
  C16    0.0286 (8)    0.8274 (8)    0.7570 (2)     0.112 (3)            
  H16    −0.0295       0.8827        0.7413         0.134\*              
  C17    0.1515 (8)    0.8224 (8)    0.74818 (19)   0.100 (2)            
  H17    0.1779        0.8738        0.7264         0.121\*              
  C18    0.2346 (7)    0.7413 (9)    0.7715 (2)     0.114 (3)            
  H18    0.3188        0.7375        0.7659         0.137\*              
  C19    0.1952 (7)    0.6646 (8)    0.8034 (2)     0.095 (2)            
  H19    0.2535        0.6088        0.8189         0.114\*              
  C20    0.8513 (5)    0.8847 (5)    1.08785 (16)   0.0553 (13)          
  C21    0.8191 (6)    0.8677 (6)    1.12796 (18)   0.0803 (17)          
  H21    0.7370        0.8410        1.1321         0.096\*              
  C22    0.9048 (7)    0.8893 (8)    1.1613 (2)     0.100 (2)            
  H22    0.8815        0.8767        1.1878         0.120\*              
  C23    1.0274 (6)    0.9302 (6)    1.15529 (19)   0.0836 (18)          
  H23    1.0865        0.9447        1.1779         0.100\*              
  C24    1.0607 (5)    0.9488 (6)    1.11692 (18)   0.0693 (15)          
  H24    1.1427        0.9772        1.1134         0.083\*              
  C25    0.9754 (5)    0.9267 (5)    1.08249 (16)   0.0564 (13)          
  C26    0.7581 (5)    0.8606 (5)    1.05304 (16)   0.0573 (13)          
  H26    0.6773        0.8313        1.0578         0.069\*              
  C27    0.6858 (5)    0.8565 (5)    0.98220 (15)   0.0605 (14)          
  H27    0.6128        0.8100        0.9924         0.073\*              
  C28    0.6448 (5)    0.9970 (5)    0.96375 (16)   0.0632 (14)          
  H28A   0.6056        1.0515        0.9841         0.076\*              
  H28B   0.7185        1.0472        0.9563         0.076\*              
  C29    0.5523 (5)    0.9782 (5)    0.92612 (17)   0.0661 (15)          
  H29A   0.4767        0.9324        0.9339         0.079\*              
  H29B   0.5278        1.0684        0.9148         0.079\*              
  C30    0.6422 (5)    0.7581 (5)    0.91122 (16)   0.0694 (15)          
  H30A   0.6789        0.7040        0.8903         0.083\*              
  H30B   0.5669        0.7102        0.9183         0.083\*              
  C31    0.7362 (5)    0.7691 (5)    0.94894 (16)   0.0682 (15)          
  H31A   0.8142        0.8099        0.9413         0.082\*              
  H31B   0.7557        0.6768        0.9597         0.082\*              
  C32    0.5155 (5)    0.8848 (6)    0.85825 (17)   0.0768 (16)          
  H32A   0.4821        0.9766        0.8514         0.092\*              
  H32B   0.4453        0.8272        0.8650         0.092\*              
  C33    0.5680 (5)    0.8258 (6)    0.82132 (17)   0.0676 (15)          
  C34    0.5566 (6)    0.6876 (7)    0.8109 (2)     0.0862 (18)          
  H34    0.5168        0.6284        0.8281         0.103\*              
  C35    0.6009 (7)    0.6343 (8)    0.7766 (2)     0.099 (2)            
  H35    0.5930        0.5398        0.7711         0.119\*              
  C36    0.6567 (7)    0.7187 (10)   0.7504 (2)     0.102 (2)            
  H36    0.6847        0.6827        0.7264         0.122\*              
  C37    0.6717 (7)    0.8574 (9)    0.7594 (2)     0.103 (2)            
  H37    0.7110        0.9157        0.7417         0.123\*              
  C38    0.6278 (6)    0.9096 (7)    0.7950 (2)     0.0878 (19)          
  H38    0.6390        1.0032        0.8013         0.105\*              
  N1     0.2660 (4)    0.6217 (4)    1.00875 (13)   0.0562 (11)          
  N2     0.1097 (4)    0.5853 (4)    0.88561 (12)   0.0586 (11)          
  N3     0.7836 (4)    0.8785 (4)    1.01623 (13)   0.0578 (11)          
  N4     0.6071 (4)    0.8956 (4)    0.89468 (13)   0.0597 (11)          
  O1     0.4961 (4)    0.5668 (4)    1.03919 (12)   0.0746 (11)          
  O2     1.0116 (4)    0.9462 (4)    1.04478 (12)   0.0777 (12)          
  H2A    0.937 (7)     0.915 (7)     1.023 (2)      0.14 (3)\*           
  H1     0.424 (7)     0.574 (8)     1.017 (2)      0.15 (3)\*           
  ------ ------------- ------------- -------------- -------------------- --

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

  ----- ----------- ----------- ----------- ------------ ------------ ------------
        *U*^11^     *U*^22^     *U*^33^     *U*^12^      *U*^13^      *U*^23^
  C1    0.072 (4)   0.037 (3)   0.060 (3)   −0.002 (2)   0.016 (3)    −0.001 (2)
  C2    0.102 (5)   0.061 (4)   0.065 (4)   0.009 (3)    0.024 (4)    −0.001 (3)
  C3    0.133 (6)   0.067 (4)   0.066 (4)   −0.003 (4)   0.019 (4)    −0.013 (3)
  C4    0.109 (5)   0.075 (4)   0.062 (4)   −0.018 (4)   −0.009 (4)   0.003 (3)
  C5    0.082 (4)   0.068 (4)   0.059 (3)   −0.013 (3)   0.003 (3)    0.004 (3)
  C6    0.074 (4)   0.047 (3)   0.054 (3)   −0.011 (3)   0.007 (3)    −0.003 (2)
  C7    0.058 (3)   0.039 (3)   0.078 (4)   0.001 (2)    0.016 (3)    0.007 (3)
  C8    0.054 (3)   0.047 (3)   0.069 (3)   0.007 (2)    0.008 (3)    0.005 (3)
  C9    0.063 (3)   0.041 (3)   0.086 (4)   −0.002 (2)   0.007 (3)    0.010 (3)
  C10   0.066 (3)   0.047 (3)   0.087 (4)   −0.005 (3)   0.000 (3)    0.008 (3)
  C11   0.069 (3)   0.041 (3)   0.077 (4)   0.004 (3)    0.004 (3)    0.006 (3)
  C12   0.073 (4)   0.036 (3)   0.071 (3)   −0.007 (2)   0.004 (3)    0.000 (2)
  C13   0.075 (4)   0.069 (4)   0.086 (4)   −0.009 (3)   −0.011 (3)   −0.005 (3)
  C14   0.067 (4)   0.066 (4)   0.066 (3)   0.004 (3)    −0.005 (3)   −0.005 (3)
  C15   0.070 (4)   0.114 (6)   0.094 (5)   0.011 (4)    −0.010 (4)   0.017 (4)
  C16   0.114 (7)   0.134 (7)   0.084 (5)   0.015 (5)    −0.007 (4)   0.035 (5)
  C17   0.104 (6)   0.129 (6)   0.067 (4)   −0.009 (5)   0.003 (4)    0.009 (4)
  C18   0.085 (5)   0.163 (8)   0.094 (5)   0.009 (5)    0.011 (4)    0.012 (5)
  C19   0.088 (5)   0.115 (6)   0.082 (4)   0.028 (4)    0.003 (4)    0.015 (4)
  C20   0.060 (3)   0.040 (3)   0.068 (3)   0.003 (2)    0.014 (3)    0.005 (2)
  C21   0.074 (4)   0.091 (4)   0.079 (4)   −0.013 (3)   0.020 (3)    0.005 (4)
  C22   0.107 (6)   0.122 (6)   0.072 (4)   −0.023 (5)   0.014 (4)    0.010 (4)
  C23   0.092 (5)   0.087 (5)   0.070 (4)   −0.002 (4)   −0.002 (3)   0.005 (3)
  C24   0.064 (4)   0.065 (4)   0.078 (4)   0.008 (3)    0.005 (3)    0.013 (3)
  C25   0.061 (3)   0.045 (3)   0.065 (3)   0.008 (2)    0.014 (3)    0.009 (2)
  C26   0.060 (3)   0.038 (3)   0.077 (4)   −0.002 (2)   0.022 (3)    0.003 (3)
  C27   0.066 (3)   0.047 (3)   0.070 (3)   −0.009 (3)   0.014 (3)    0.002 (3)
  C28   0.062 (3)   0.047 (3)   0.081 (4)   0.002 (3)    0.013 (3)    −0.004 (3)
  C29   0.058 (3)   0.049 (3)   0.093 (4)   0.009 (3)    0.014 (3)    0.002 (3)
  C30   0.085 (4)   0.049 (3)   0.075 (4)   0.005 (3)    0.007 (3)    −0.005 (3)
  C31   0.084 (4)   0.043 (3)   0.077 (4)   0.011 (3)    0.007 (3)    0.002 (3)
  C32   0.065 (4)   0.076 (4)   0.088 (4)   0.010 (3)    −0.001 (3)   0.001 (3)
  C33   0.064 (4)   0.063 (4)   0.073 (4)   0.003 (3)    −0.009 (3)   0.003 (3)
  C34   0.089 (5)   0.076 (4)   0.094 (5)   −0.003 (4)   0.008 (4)    −0.008 (4)
  C35   0.103 (6)   0.096 (5)   0.095 (5)   0.012 (4)    −0.004 (4)   −0.013 (5)
  C36   0.092 (5)   0.140 (7)   0.070 (4)   0.032 (5)    −0.005 (4)   −0.012 (5)
  C37   0.106 (6)   0.123 (7)   0.078 (5)   0.008 (5)    0.003 (4)    0.028 (5)
  C38   0.092 (5)   0.076 (4)   0.091 (5)   0.002 (4)    −0.013 (4)   0.007 (4)
  N1    0.058 (3)   0.049 (2)   0.063 (3)   0.004 (2)    0.010 (2)    0.002 (2)
  N2    0.065 (3)   0.041 (2)   0.068 (3)   −0.004 (2)   −0.005 (2)   0.000 (2)
  N3    0.058 (3)   0.049 (2)   0.069 (3)   −0.003 (2)   0.016 (2)    0.000 (2)
  N4    0.056 (3)   0.047 (2)   0.075 (3)   0.007 (2)    0.004 (2)    0.001 (2)
  O1    0.065 (2)   0.101 (3)   0.059 (2)   0.006 (2)    0.010 (2)    −0.011 (2)
  O2    0.062 (2)   0.101 (3)   0.072 (3)   −0.010 (2)   0.019 (2)    0.008 (2)
  ----- ----------- ----------- ----------- ------------ ------------ ------------

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

  ----------------------- ------------ ----------------------- ------------
  C1---C2                 1.386 (7)    C20---C25               1.404 (6)
  C1---C6                 1.409 (7)    C20---C26               1.449 (7)
  C1---C7                 1.453 (7)    C21---C22               1.362 (8)
  C2---C3                 1.368 (8)    C21---H21               0.9300
  C2---H2                 0.9300       C22---C23               1.390 (8)
  C3---C4                 1.389 (8)    C22---H22               0.9300
  C3---H3                 0.9300       C23---C24               1.344 (7)
  C4---C5                 1.361 (7)    C23---H23               0.9300
  C4---H4                 0.9300       C24---C25               1.387 (7)
  C5---C6                 1.381 (7)    C24---H24               0.9300
  C5---H5                 0.9300       C25---O2                1.336 (6)
  C6---O1                 1.342 (6)    C26---N3                1.267 (6)
  C7---N1                 1.262 (6)    C26---H26               0.9300
  C7---H7                 0.9300       C27---N3                1.458 (6)
  C8---N1                 1.455 (6)    C27---C31               1.511 (7)
  C8---C9                 1.516 (7)    C27---C28               1.527 (7)
  C8---C12                1.517 (6)    C27---H27               0.9800
  C8---H8                 0.9800       C28---C29               1.504 (7)
  C9---C10                1.514 (7)    C28---H28A              0.9700
  C9---H9A                0.9700       C28---H28B              0.9700
  C9---H9B                0.9700       C29---N4                1.462 (6)
  C10---N2                1.461 (6)    C29---H29A              0.9700
  C10---H10A              0.9700       C29---H29B              0.9700
  C10---H10B              0.9700       C30---N4                1.464 (6)
  C11---N2                1.462 (6)    C30---C31               1.509 (7)
  C11---C12               1.512 (6)    C30---H30A              0.9700
  C11---H11A              0.9700       C30---H30B              0.9700
  C11---H11B              0.9700       C31---H31A              0.9700
  C12---H12A              0.9700       C31---H31B              0.9700
  C12---H12B              0.9700       C32---N4                1.463 (6)
  C13---N2                1.456 (6)    C32---C33               1.487 (7)
  C13---C14               1.498 (7)    C32---H32A              0.9700
  C13---H13A              0.9700       C32---H32B              0.9700
  C13---H13B              0.9700       C33---C38               1.376 (8)
  C14---C15               1.360 (7)    C33---C34               1.377 (8)
  C14---C19               1.377 (8)    C34---C35               1.353 (8)
  C15---C16               1.384 (9)    C34---H34               0.9300
  C15---H15               0.9300       C35---C36               1.357 (9)
  C16---C17               1.363 (9)    C35---H35               0.9300
  C16---H16               0.9300       C36---C37               1.374 (10)
  C17---C18               1.355 (9)    C36---H36               0.9300
  C17---H17               0.9300       C37---C38               1.388 (9)
  C18---C19               1.372 (9)    C37---H37               0.9300
  C18---H18               0.9300       C38---H38               0.9300
  C19---H19               0.9300       O1---H1                 1.01 (8)
  C20---C21               1.393 (7)    O2---H2A                1.05 (7)
                                                               
  C2---C1---C6            118.1 (5)    C20---C21---H21         119.2
  C2---C1---C7            121.2 (5)    C21---C22---C23         119.4 (6)
  C6---C1---C7            120.7 (5)    C21---C22---H22         120.3
  C3---C2---C1            121.9 (6)    C23---C22---H22         120.3
  C3---C2---H2            119.0        C24---C23---C22         120.2 (6)
  C1---C2---H2            119.0        C24---C23---H23         119.9
  C2---C3---C4            118.8 (6)    C22---C23---H23         119.9
  C2---C3---H3            120.6        C23---C24---C25         121.5 (6)
  C4---C3---H3            120.6        C23---C24---H24         119.2
  C5---C4---C3            120.9 (6)    C25---C24---H24         119.2
  C5---C4---H4            119.5        O2---C25---C24          120.0 (5)
  C3---C4---H4            119.5        O2---C25---C20          120.8 (5)
  C4---C5---C6            120.5 (6)    C24---C25---C20         119.2 (5)
  C4---C5---H5            119.8        N3---C26---C20          121.8 (5)
  C6---C5---H5            119.8        N3---C26---H26          119.1
  O1---C6---C5            118.8 (5)    C20---C26---H26         119.1
  O1---C6---C1            121.4 (5)    N3---C27---C31          110.5 (4)
  C5---C6---C1            119.7 (5)    N3---C27---C28          109.0 (4)
  N1---C7---C1            122.6 (5)    C31---C27---C28         108.6 (4)
  N1---C7---H7            118.7        N3---C27---H27          109.6
  C1---C7---H7            118.7        C31---C27---H27         109.6
  N1---C8---C9            109.6 (4)    C28---C27---H27         109.6
  N1---C8---C12           110.0 (4)    C29---C28---C27         110.6 (4)
  C9---C8---C12           109.9 (4)    C29---C28---H28A        109.5
  N1---C8---H8            109.1        C27---C28---H28A        109.5
  C9---C8---H8            109.1        C29---C28---H28B        109.5
  C12---C8---H8           109.1        C27---C28---H28B        109.5
  C10---C9---C8           111.8 (4)    H28A---C28---H28B       108.1
  C10---C9---H9A          109.3        N4---C29---C28          111.4 (4)
  C8---C9---H9A           109.3        N4---C29---H29A         109.3
  C10---C9---H9B          109.3        C28---C29---H29A        109.3
  C8---C9---H9B           109.3        N4---C29---H29B         109.3
  H9A---C9---H9B          107.9        C28---C29---H29B        109.3
  N2---C10---C9           112.0 (4)    H29A---C29---H29B       108.0
  N2---C10---H10A         109.2        N4---C30---C31          111.1 (4)
  C9---C10---H10A         109.2        N4---C30---H30A         109.4
  N2---C10---H10B         109.2        C31---C30---H30A        109.4
  C9---C10---H10B         109.2        N4---C30---H30B         109.4
  H10A---C10---H10B       107.9        C31---C30---H30B        109.4
  N2---C11---C12          110.9 (4)    H30A---C30---H30B       108.0
  N2---C11---H11A         109.5        C30---C31---C27         111.8 (4)
  C12---C11---H11A        109.5        C30---C31---H31A        109.3
  N2---C11---H11B         109.5        C27---C31---H31A        109.3
  C12---C11---H11B        109.5        C30---C31---H31B        109.3
  H11A---C11---H11B       108.1        C27---C31---H31B        109.3
  C11---C12---C8          111.3 (4)    H31A---C31---H31B       107.9
  C11---C12---H12A        109.4        N4---C32---C33          114.4 (4)
  C8---C12---H12A         109.4        N4---C32---H32A         108.7
  C11---C12---H12B        109.4        C33---C32---H32A        108.7
  C8---C12---H12B         109.4        N4---C32---H32B         108.7
  H12A---C12---H12B       108.0        C33---C32---H32B        108.7
  N2---C13---C14          114.8 (5)    H32A---C32---H32B       107.6
  N2---C13---H13A         108.6        C38---C33---C34         116.6 (6)
  C14---C13---H13A        108.6        C38---C33---C32         120.8 (6)
  N2---C13---H13B         108.6        C34---C33---C32         122.6 (6)
  C14---C13---H13B        108.6        C35---C34---C33         122.8 (7)
  H13A---C13---H13B       107.5        C35---C34---H34         118.6
  C15---C14---C19         116.8 (6)    C33---C34---H34         118.6
  C15---C14---C13         120.6 (6)    C34---C35---C36         120.0 (7)
  C19---C14---C13         122.6 (5)    C34---C35---H35         120.0
  C14---C15---C16         121.7 (7)    C36---C35---H35         120.0
  C14---C15---H15         119.1        C35---C36---C37         119.8 (7)
  C16---C15---H15         119.1        C35---C36---H36         120.1
  C17---C16---C15         120.2 (7)    C37---C36---H36         120.1
  C17---C16---H16         119.9        C36---C37---C38         119.3 (7)
  C15---C16---H16         119.9        C36---C37---H37         120.4
  C18---C17---C16         119.0 (7)    C38---C37---H37         120.4
  C18---C17---H17         120.5        C33---C38---C37         121.5 (7)
  C16---C17---H17         120.5        C33---C38---H38         119.3
  C17---C18---C19         120.4 (7)    C37---C38---H38         119.3
  C17---C18---H18         119.8        C7---N1---C8            120.6 (4)
  C19---C18---H18         119.8        C13---N2---C10          109.5 (4)
  C18---C19---C14         121.8 (6)    C13---N2---C11          111.3 (4)
  C18---C19---H19         119.1        C10---N2---C11          109.0 (4)
  C14---C19---H19         119.1        C26---N3---C27          119.9 (4)
  C21---C20---C25         118.0 (5)    C29---N4---C32          109.3 (4)
  C21---C20---C26         120.4 (5)    C29---N4---C30          109.8 (4)
  C25---C20---C26         121.7 (5)    C32---N4---C30          111.1 (4)
  C22---C21---C20         121.7 (6)    C6---O1---H1            111 (4)
  C22---C21---H21         119.2        C25---O2---H2A          109 (4)
                                                               
  C6---C1---C2---C3       1.4 (8)      C21---C20---C25---C24   0.3 (7)
  C7---C1---C2---C3       −177.8 (5)   C26---C20---C25---C24   179.7 (5)
  C1---C2---C3---C4       −1.0 (9)     C21---C20---C26---N3    178.2 (5)
  C2---C3---C4---C5       −0.5 (9)     C25---C20---C26---N3    −1.1 (7)
  C3---C4---C5---C6       1.4 (9)      N3---C27---C28---C29    174.9 (4)
  C4---C5---C6---O1       178.9 (5)    C31---C27---C28---C29   54.5 (6)
  C4---C5---C6---C1       −0.9 (8)     C27---C28---C29---N4    −58.7 (6)
  C2---C1---C6---O1       179.7 (5)    N4---C30---C31---C27    57.2 (6)
  C7---C1---C6---O1       −1.1 (7)     N3---C27---C31---C30    −173.5 (4)
  C2---C1---C6---C5       −0.5 (7)     C28---C27---C31---C30   −54.0 (6)
  C7---C1---C6---C5       178.7 (5)    N4---C32---C33---C38    −85.8 (7)
  C2---C1---C7---N1       −179.7 (5)   N4---C32---C33---C34    96.1 (7)
  C6---C1---C7---N1       1.2 (7)      C38---C33---C34---C35   −0.1 (9)
  N1---C8---C9---C10      −171.3 (4)   C32---C33---C34---C35   178.0 (6)
  C12---C8---C9---C10     −50.2 (6)    C33---C34---C35---C36   −1.6 (10)
  C8---C9---C10---N2      55.4 (6)     C34---C35---C36---C37   2.1 (11)
  N2---C11---C12---C8     −58.8 (6)    C35---C36---C37---C38   −0.9 (11)
  N1---C8---C12---C11     172.8 (4)    C34---C33---C38---C37   1.4 (9)
  C9---C8---C12---C11     52.1 (5)     C32---C33---C38---C37   −176.8 (5)
  N2---C13---C14---C15    −136.4 (6)   C36---C37---C38---C33   −0.9 (10)
  N2---C13---C14---C19    45.2 (8)     C1---C7---N1---C8       −179.5 (4)
  C19---C14---C15---C16   −0.2 (10)    C9---C8---N1---C7       −118.2 (5)
  C13---C14---C15---C16   −178.7 (6)   C12---C8---N1---C7      120.8 (5)
  C14---C15---C16---C17   0.0 (12)     C14---C13---N2---C10    −177.4 (5)
  C15---C16---C17---C18   −0.1 (12)    C14---C13---N2---C11    62.1 (6)
  C16---C17---C18---C19   0.5 (12)     C9---C10---N2---C13     178.0 (4)
  C17---C18---C19---C14   −0.7 (12)    C9---C10---N2---C11     −60.0 (5)
  C15---C14---C19---C18   0.6 (10)     C12---C11---N2---C13    −177.6 (4)
  C13---C14---C19---C18   179.0 (6)    C12---C11---N2---C10    61.6 (5)
  C25---C20---C21---C22   −0.8 (9)     C20---C26---N3---C27    −178.4 (4)
  C26---C20---C21---C22   179.9 (6)    C31---C27---N3---C26    −132.8 (5)
  C20---C21---C22---C23   0.5 (11)     C28---C27---N3---C26    107.9 (5)
  C21---C22---C23---C24   0.3 (10)     C28---C29---N4---C32    −177.8 (4)
  C22---C23---C24---C25   −0.7 (9)     C28---C29---N4---C30    60.1 (5)
  C23---C24---C25---O2    180.0 (5)    C33---C32---N4---C29    169.3 (5)
  C23---C24---C25---C20   0.4 (8)      C33---C32---N4---C30    −69.5 (6)
  C21---C20---C25---O2    −179.3 (5)   C31---C30---N4---C29    −58.7 (6)
  C26---C20---C25---O2    0.1 (7)      C31---C30---N4---C32    −179.7 (4)
  ----------------------- ------------ ----------------------- ------------

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

  ----------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*     *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  O1---H1···N1      1.01 (8)   1.73 (7)   2.597 (5)   141 (6)
  O2---H2A···N3     1.05 (7)   1.66 (7)   2.588 (6)   144 (5)
  O1---H1···O1^i^   1.01 (8)   2.49 (7)   2.869 (7)   102 (5)
  ----------------- ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*     *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  --------------- ---------- ---------- ----------- -------------
  O1---H1⋯N1      1.01 (8)   1.73 (7)   2.597 (5)   141 (6)
  O2---H2*A*⋯N3   1.05 (7)   1.66 (7)   2.588 (6)   144 (5)
  O1---H1⋯O1^i^   1.01 (8)   2.49 (7)   2.869 (7)   102 (5)

Symmetry code: (i) .
