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

For the biological properties of 8-hydroxy­quinoline derivatives, see: Chen *et al.* (2002[@bb3]); Fakhfakh *et al.* (2003[@bb4]); Mekouar *et al.* (1998[@bb5]); Ouali *et al.* (2000[@bb6]); Storz *et al.* (2004[@bb8]); Zeng, Wang *et al.* (2006[@bb10]). For a related crystal structure, see: Zeng, OuYang *et al.* (2006[@bb9]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~19~H~14~N~2~O~4~*M* *~r~* = 334.32Orthorhombic,*a* = 25.8466 (13) Å*b* = 11.8451 (6) Å*c* = 10.5870 (5) Å*V* = 3241.3 (3) Å^3^*Z* = 8Mo *K*α radiationμ = 0.10 mm^−1^*T* = 173 K0.47 × 0.45 × 0.26 mm

### Data collection {#sec2.1.2}

Bruker SMART 1000 CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2001[@bb1]) *T* ~min~ = 0.956, *T* ~max~ = 0.97517451 measured reflections3731 independent reflections2785 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.039

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.058*wR*(*F* ^2^) = 0.171*S* = 1.043731 reflections453 parameters7 restraintsH-atom parameters constrainedΔρ~max~ = 0.56 e Å^−3^Δρ~min~ = −0.22 e Å^−3^

 {#d5e359}

Data collection: *SMART* (Bruker, 2001[@bb1]); cell refinement: *SAINT-Plus* (Bruker, 2003[@bb2]); data reduction: *SAINT-Plus*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablocks I, global. DOI: [10.1107/S1600536809044158/wn2356sup1.cif](http://dx.doi.org/10.1107/S1600536809044158/wn2356sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809044158/wn2356Isup2.hkl](http://dx.doi.org/10.1107/S1600536809044158/wn2356Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?wn2356&file=wn2356sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?wn2356sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?wn2356&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [WN2356](http://scripts.iucr.org/cgi-bin/sendsup?wn2356)).

This work was supported by the National Natural Science Foundation of China (20802010), the Natural Science Foundation of Guangdong Province (No. 07300884) and the 211 project of Guangdong University of Technology.

Comment
=======

8-Hydroxyquinoline derivatives are important constituents in a variety of classes of pharmaceutically important compounds. They have generated interest as a new class of potent HIV-1 integrase inhibitors (Mekouar *et al.*, 1998), for modeling of the inhibition of retroviral integrases (Ouali *et al.*, 2000), as protein tyrosine kinase inhibitors (Chen *et al.*, 2002), as protozoal and retroviral co-infections (Fakhfakh *et al.*, 2003), and as anti-HIV-1 agents (Storz *et al.*, 2004). Zeng, Wang *et al.* (2006) reported that a series of 8-hydroxyquinoline derivatives with vinyl substituents at the 2-position could induce the proliferation of rMSCs (rat mesenchymal stem cells). With these findings, some analogs need to be synthesized for structure activity relationship research to find more potent molecules.

One of these analogs, the title compound, (*E*)-2-\[2-(2-nitrophenyl)ethenyl\]-8-acetoxyquinoline, was prepared by the Knoevenagel condensation reaction between 8-hydroxyquinaldine and 2-nitrobenzaldehyde (Zeng, OuYang *et al.* (2006)) (Fig. 1). To provide structural information for the title compound, we studied its crystal structure.

The molecular structure of the two molecules per asymmetric unit is illustrated in Fig. 2. In one molecule, the angle between the two ring systems is 8.7 (1)°; in the other it is 4.2 (1)°. In this crystal structure, the ethylenic bond lengths for C1---C2 and C26---C27 are 1.322 (5) and 1.329 (5) Å, respectively. The analogous bond reported by Zeng, OuYang *et al.* (2006) has a length of 1.335 (2) Å. Intermolecular π--π interactions, with a centroid···centroid distance of 3.973 (1) Å, lead directly to a three-dimensional supramolecular network (Fig. 3).

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

To a solution of 8-hydroxyquinaldine (1.19 g, 7.5 mmol) in acetic anhydride (5 ml) was added 2-nitrobenzaldehyde (1.12 g, 7.5 mmol). The mixture was heated under reflux for 11 h. After cooling, it was poured into ice water (50 ml) and stirred overnight. The yellow solid obtained was filtered and washed with water. The solid residue was recrystallized from CH~2~Cl~2~to afford the title compound (2.04 g, 75%). mp 143--144 °C. 20 mg was dissolved in 10 ml (EtOAc:petroleum ether 1:4) and the solution was kept at room temperature for 4 d. Natural evaporation gave orange single crystals suitable for X-ray analysis.

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

All H atoms were positioned geometrically and refined using a riding model (including free rotation about the acetoxy C---C bond), with C---H = 0.95 Å (Csp^2^) and 0.98 Å (methyl C); *U*~iso~(H) = k*U*~eq~(C), where k = 1.5 for methyl H atoms and 1.2 for all other H atoms. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Figures
=======

![The synthesis of (E)-2-\[2-(2-nitrophenyl)ethenyl\]-8-acetoxyquinoline.](e-65-o2960-fig1){#Fap1}

![View of the asymmetric unit of the title compound. Hydrogen atoms have been omitted.](e-65-o2960-fig2){#Fap2}

![View of the three-dimensional supramolecular structure.](e-65-o2960-fig3){#Fap3}

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

  ------------------------- ---------------------------------------
  C~19~H~14~N~2~O~4~        *F*(000) = 1392
  *M~r~* = 334.32           *D*~x~ = 1.370 Mg m^−3^
  Orthorhombic, *Pna*2~1~   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: P 2c -2n     Cell parameters from 5386 reflections
  *a* = 25.8466 (13) Å      θ = 2.3--26.3°
  *b* = 11.8451 (6) Å       µ = 0.10 mm^−1^
  *c* = 10.5870 (5) Å       *T* = 173 K
  *V* = 3241.3 (3) Å^3^     Block, yellow
  *Z* = 8                   0.47 × 0.45 × 0.26 mm
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART 1000 CCD diffractometer                         3731 independent reflections
  Radiation source: fine-focus sealed tube                     2785 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.039
  ω scans                                                      θ~max~ = 27.1°, θ~min~ = 1.6°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2001)   *h* = −29→33
  *T*~min~ = 0.956, *T*~max~ = 0.975                           *k* = −13→15
  17451 measured reflections                                   *l* = −13→13
  ------------------------------------------------------------ --------------------------------------

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^) = 0.171                  H-atom parameters constrained
  *S* = 1.04                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.1126*P*)^2^ + 0.5654*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3731 reflections                      (Δ/σ)~max~ = 0.004
  453 parameters                        Δρ~max~ = 0.56 e Å^−3^
  7 restraints                          Δρ~min~ = −0.22 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Experimental. ^1^H NMR (CDCl~3~, 300 MHz) δ 8.17--8.26 (m, 2H), 7.94 (d, J=7.5 Hz, 1H), 7.82 (d, J=7.8 Hz 1H), 7.64--7.70 (m, 4H), 7.47--7.53 (m, 3H), 2.58(s, 3H); IR (KBr, cm^-1^): 3067, 1723, 1577, 1520, 1457, 1175, 1128, 970, 850, 765, 708; ESI-MS m/*z*: 335.9 (\[*M*+H\]^+^); Elemental analysis: found C: 68.45, H: 4.40, N: 8.38 (%)
  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     0.79027 (14)   0.4406 (3)    0.2939 (4)    0.0354 (9)           
  H1     0.7753         0.5118        0.2748        0.043\*              
  C2     0.83678 (14)   0.4416 (3)    0.3458 (4)    0.0347 (8)           
  H2     0.8522         0.3712        0.3664        0.042\*              
  C3     0.92068 (14)   0.7392 (3)    0.4307 (4)    0.0337 (9)           
  C4     0.87102 (14)   0.7393 (3)    0.3743 (4)    0.0301 (8)           
  N5     0.84409 (11)   0.6440 (3)    0.3460 (3)    0.0299 (7)           
  C6     0.86607 (13)   0.5452 (3)    0.3734 (4)    0.0321 (8)           
  C7     0.91645 (16)   0.5376 (4)    0.4257 (4)    0.0383 (9)           
  H7     0.9315         0.4656        0.4403        0.046\*              
  C8     0.94344 (14)   0.6324 (4)    0.4549 (4)    0.0396 (10)          
  H8     0.9770         0.6273        0.4910        0.048\*              
  C9     0.94489 (16)   0.8434 (4)    0.4613 (4)    0.0432 (10)          
  H9     0.9779         0.8436        0.5007        0.052\*              
  C10    0.92101 (17)   0.9425 (4)    0.4346 (4)    0.0447 (10)          
  H10    0.9372         1.0116        0.4569        0.054\*              
  C11    0.87218 (16)   0.9444 (3)    0.3739 (4)    0.0393 (9)           
  H11    0.8560         1.0143        0.3544        0.047\*              
  C12    0.84871 (14)   0.8454 (3)    0.3436 (4)    0.0310 (8)           
  O13    0.79975 (10)   0.8466 (2)    0.2896 (3)    0.0343 (6)           
  C14    0.75968 (15)   0.3408 (3)    0.2631 (4)    0.0360 (9)           
  C15    0.71059 (16)   0.3464 (4)    0.2113 (5)    0.0470 (11)          
  C16    0.67993 (18)   0.2511 (5)    0.1900 (6)    0.0594 (15)          
  H16    0.6458         0.2589        0.1576        0.071\*              
  C17    0.6995 (2)     0.1471 (5)    0.2162 (5)    0.0580 (14)          
  H17    0.6794         0.0815        0.2005        0.070\*              
  C18    0.74860 (19)   0.1373 (4)    0.2656 (5)    0.0492 (11)          
  H18    0.7623         0.0646        0.2834        0.059\*              
  C19    0.77801 (16)   0.2319 (3)    0.2896 (4)    0.0395 (10)          
  H19    0.8116         0.2231        0.3249        0.047\*              
  C20    0.79586 (15)   0.8136 (3)    0.1658 (4)    0.0330 (8)           
  O21    0.83315 (11)   0.7982 (2)    0.1009 (3)    0.0417 (7)           
  C22    0.74072 (15)   0.8026 (4)    0.1270 (5)    0.0473 (11)          
  H22A   0.7385         0.8011        0.0346        0.071\*              
  H22B   0.7210         0.8670        0.1594        0.071\*              
  H22C   0.7264         0.7324        0.1614        0.071\*              
  N23    0.68857 (17)   0.4577 (5)    0.1744 (6)    0.0746 (17)          
  O24    0.7137 (2)     0.5202 (4)    0.1073 (7)    0.101 (2)            
  O25    0.64504 (18)   0.4750 (5)    0.2109 (7)    0.124 (2)            
  C26    0.46521 (13)   −0.0779 (3)   0.1266 (4)    0.0304 (8)           
  H26    0.4808         −0.0079       0.1483        0.036\*              
  C27    0.41923 (15)   −0.0756 (3)   0.0705 (4)    0.0358 (9)           
  H27    0.4045         −0.1458       0.0459        0.043\*              
  C28    0.33041 (14)   0.2153 (3)    −0.0099 (4)   0.0321 (8)           
  C29    0.37963 (13)   0.2194 (3)    0.0491 (4)    0.0290 (8)           
  N30    0.40900 (11)   0.1266 (3)    0.0752 (3)    0.0308 (7)           
  C31    0.38950 (14)   0.0269 (3)    0.0438 (4)    0.0318 (8)           
  C32    0.33986 (15)   0.0140 (3)    −0.0117 (4)   0.0378 (9)           
  H32    0.3268         −0.0592       −0.0298       0.045\*              
  C33    0.31110 (15)   0.1068 (4)    −0.0387 (4)   0.0376 (9)           
  H33    0.2780         0.0988        −0.0768       0.045\*              
  C34    0.30335 (15)   0.3162 (3)    −0.0367 (4)   0.0364 (9)           
  H34    0.2705         0.3132        −0.0767       0.044\*              
  C35    0.32446 (16)   0.4174 (4)    −0.0053 (4)   0.0415 (10)          
  H35    0.3063         0.4849        −0.0247       0.050\*              
  C36    0.37324 (15)   0.4241 (3)    0.0561 (4)    0.0383 (9)           
  H36    0.3876         0.4955        0.0772        0.046\*              
  C37    0.39908 (14)   0.3276 (3)    0.0842 (4)    0.0314 (8)           
  O38    0.44801 (10)   0.3328 (2)    0.1386 (3)    0.0339 (6)           
  C39    0.49328 (13)   −0.1817 (3)   0.1570 (4)    0.0305 (8)           
  C40    0.54472 (14)   −0.1848 (3)   0.2014 (4)    0.0340 (9)           
  C41    0.57112 (16)   −0.2840 (4)   0.2254 (5)    0.0425 (11)          
  H41    0.6063         −0.2822       0.2513        0.051\*              
  C42    0.54573 (16)   −0.3852 (4)   0.2111 (5)    0.0458 (10)          
  H42    0.5628         −0.4540       0.2311        0.055\*              
  C43    0.49544 (15)   −0.3867 (3)   0.1678 (5)    0.0428 (10)          
  H43    0.4782         −0.4568       0.1564        0.051\*              
  C44    0.46994 (14)   −0.2877 (3)   0.1411 (4)    0.0360 (9)           
  H44    0.4354         −0.2912       0.1109        0.043\*              
  C45    0.45270 (15)   0.2938 (3)    0.2601 (4)    0.0345 (9)           
  O46    0.41633 (11)   0.2756 (3)    0.3261 (3)    0.0436 (7)           
  C47    0.50824 (17)   0.2795 (4)    0.2951 (5)    0.0510 (12)          
  H47A   0.5112         0.2715        0.3870        0.076\*              
  H47B   0.5279         0.3458        0.2674        0.076\*              
  H47C   0.5221         0.2118        0.2540        0.076\*              
  N48    0.57481 (13)   −0.0810 (3)   0.2185 (4)    0.0428 (9)           
  O49    0.55389 (14)   0.0009 (3)    0.2665 (4)    0.0621 (10)          
  O50    0.62029 (12)   −0.0830 (3)   0.1858 (4)    0.0628 (10)          
  ------ -------------- ------------- ------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  C1    0.037 (2)     0.033 (2)     0.036 (2)     0.0056 (15)    −0.0016 (16)   −0.0013 (16)
  C2    0.0349 (19)   0.0296 (19)   0.039 (2)     0.0053 (15)    0.0015 (16)    0.0038 (16)
  C3    0.0286 (19)   0.049 (2)     0.023 (2)     −0.0057 (16)   −0.0027 (16)   0.0050 (16)
  C4    0.0296 (19)   0.038 (2)     0.0223 (19)   −0.0017 (15)   0.0006 (15)    0.0022 (15)
  N5    0.0253 (15)   0.0350 (17)   0.0293 (17)   0.0025 (12)    −0.0008 (13)   0.0008 (13)
  C6    0.0279 (18)   0.036 (2)     0.032 (2)     0.0030 (15)    0.0030 (15)    0.0058 (16)
  C7    0.039 (2)     0.045 (2)     0.031 (2)     0.0094 (17)    −0.0005 (17)   0.0089 (18)
  C8    0.0250 (19)   0.059 (3)     0.035 (2)     0.0009 (17)    −0.0046 (16)   0.0100 (19)
  C9    0.031 (2)     0.061 (3)     0.038 (2)     −0.0135 (19)   −0.0060 (18)   0.002 (2)
  C10   0.048 (2)     0.049 (3)     0.037 (2)     −0.021 (2)     −0.0052 (19)   −0.0014 (19)
  C11   0.040 (2)     0.037 (2)     0.040 (2)     −0.0045 (17)   −0.0010 (18)   −0.0002 (18)
  C12   0.0263 (18)   0.038 (2)     0.029 (2)     −0.0030 (14)   0.0012 (15)    −0.0016 (15)
  O13   0.0299 (13)   0.0375 (15)   0.0356 (15)   0.0027 (10)    −0.0024 (11)   −0.0036 (11)
  C14   0.032 (2)     0.039 (2)     0.036 (2)     0.0017 (16)    0.0026 (16)    −0.0066 (17)
  C15   0.039 (2)     0.060 (3)     0.042 (3)     0.0037 (19)    −0.004 (2)     −0.016 (2)
  C16   0.036 (2)     0.089 (4)     0.054 (3)     −0.007 (2)     −0.006 (2)     −0.023 (3)
  C17   0.062 (3)     0.067 (4)     0.046 (3)     −0.027 (3)     0.012 (2)      −0.008 (2)
  C18   0.058 (3)     0.042 (2)     0.047 (3)     −0.011 (2)     0.010 (2)      0.001 (2)
  C19   0.040 (2)     0.038 (2)     0.041 (3)     −0.0021 (17)   0.0066 (19)    0.0015 (18)
  C20   0.0354 (19)   0.0249 (18)   0.039 (2)     0.0032 (14)    −0.0032 (17)   0.0015 (16)
  O21   0.0397 (16)   0.0473 (16)   0.0382 (17)   0.0054 (12)    0.0026 (13)    0.0020 (13)
  C22   0.036 (2)     0.061 (3)     0.044 (3)     0.0046 (19)    −0.0094 (19)   0.000 (2)
  N23   0.045 (3)     0.089 (4)     0.090 (4)     0.028 (2)      −0.035 (3)     −0.039 (3)
  O24   0.102 (4)     0.053 (2)     0.150 (5)     0.014 (2)      −0.063 (4)     −0.004 (3)
  O25   0.077 (3)     0.167 (5)     0.126 (4)     0.071 (3)      −0.028 (3)     −0.049 (4)
  C26   0.0292 (18)   0.0292 (18)   0.0326 (19)   −0.0033 (14)   0.0012 (15)    0.0004 (15)
  C27   0.038 (2)     0.0288 (19)   0.041 (2)     0.0020 (15)    −0.0058 (17)   −0.0073 (16)
  C28   0.0293 (19)   0.043 (2)     0.024 (2)     0.0012 (16)    −0.0011 (15)   −0.0016 (16)
  C29   0.0227 (17)   0.036 (2)     0.028 (2)     0.0018 (14)    0.0017 (15)    0.0010 (15)
  N30   0.0277 (15)   0.0323 (16)   0.0324 (18)   0.0018 (12)    −0.0006 (13)   −0.0036 (13)
  C31   0.0308 (18)   0.035 (2)     0.029 (2)     −0.0003 (15)   −0.0018 (15)   −0.0031 (15)
  C32   0.036 (2)     0.035 (2)     0.043 (2)     −0.0014 (16)   −0.0104 (17)   −0.0033 (17)
  C33   0.0266 (18)   0.047 (2)     0.039 (2)     −0.0024 (16)   −0.0088 (16)   −0.0033 (19)
  C34   0.031 (2)     0.043 (2)     0.035 (2)     0.0056 (16)    −0.0038 (17)   0.0001 (18)
  C35   0.039 (2)     0.043 (2)     0.042 (3)     0.0125 (18)    0.0008 (18)    0.0050 (19)
  C36   0.039 (2)     0.033 (2)     0.043 (2)     0.0005 (16)    0.0005 (18)    −0.0004 (18)
  C37   0.0279 (18)   0.038 (2)     0.029 (2)     −0.0001 (14)   0.0028 (15)    −0.0016 (16)
  O38   0.0295 (13)   0.0325 (13)   0.0398 (16)   −0.0051 (10)   −0.0011 (11)   0.0029 (12)
  C39   0.0291 (18)   0.0318 (18)   0.031 (2)     −0.0006 (14)   0.0026 (15)    −0.0011 (16)
  C40   0.0313 (19)   0.036 (2)     0.035 (2)     −0.0040 (15)   −0.0038 (17)   −0.0019 (17)
  C41   0.032 (2)     0.045 (3)     0.051 (3)     0.0033 (17)    −0.006 (2)     0.000 (2)
  C42   0.043 (2)     0.037 (2)     0.058 (3)     0.0068 (17)    0.000 (2)      0.000 (2)
  C43   0.035 (2)     0.032 (2)     0.060 (3)     −0.0005 (16)   0.0018 (19)    −0.0030 (19)
  C44   0.0267 (18)   0.039 (2)     0.042 (2)     −0.0043 (15)   0.0031 (16)    −0.0013 (18)
  C45   0.038 (2)     0.0258 (18)   0.040 (2)     −0.0047 (15)   −0.0043 (17)   −0.0021 (16)
  O46   0.0421 (17)   0.0522 (18)   0.0366 (17)   −0.0094 (13)   0.0040 (14)    −0.0005 (14)
  C47   0.043 (3)     0.066 (3)     0.043 (3)     −0.004 (2)     −0.010 (2)     0.008 (2)
  N48   0.045 (2)     0.0363 (19)   0.047 (2)     −0.0037 (15)   −0.0175 (17)   0.0026 (16)
  O49   0.065 (2)     0.0429 (19)   0.079 (3)     −0.0009 (16)   −0.0301 (19)   −0.0133 (18)
  O50   0.0353 (16)   0.062 (2)     0.091 (3)     −0.0134 (15)   −0.0157 (17)   0.009 (2)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ----------------------- ------------ ----------------------- ------------
  C1---C2                 1.322 (5)    C26---C27               1.329 (5)
  C1---C14                1.459 (5)    C26---C39               1.464 (5)
  C1---H1                 0.9500       C26---H26               0.9500
  C2---C6                 1.471 (5)    C27---C31               1.465 (5)
  C2---H2                 0.9500       C27---H27               0.9500
  C3---C4                 1.415 (5)    C28---C33               1.412 (6)
  C3---C8                 1.418 (6)    C28---C34               1.414 (5)
  C3---C9                 1.421 (6)    C28---C29               1.418 (5)
  C4---N5                 1.361 (5)    C29---N30               1.364 (5)
  C4---C12                1.420 (5)    C29---C37               1.426 (5)
  N5---C6                 1.332 (5)    N30---C31               1.327 (5)
  C6---C7                 1.418 (5)    C31---C32               1.419 (5)
  C7---C8                 1.358 (6)    C32---C33               1.358 (6)
  C7---H7                 0.9500       C32---H32               0.9500
  C8---H8                 0.9500       C33---H33               0.9500
  C9---C10                1.357 (6)    C34---C35               1.358 (6)
  C9---H9                 0.9500       C34---H34               0.9500
  C10---C11               1.417 (6)    C35---C36               1.420 (6)
  C10---H10               0.9500       C35---H35               0.9500
  C11---C12               1.358 (5)    C36---C37               1.357 (5)
  C11---H11               0.9500       C36---H36               0.9500
  C12---O13               1.389 (4)    C37---O38               1.391 (5)
  O13---C20               1.372 (5)    O38---C45               1.372 (5)
  C14---C15               1.384 (6)    C39---C44               1.403 (5)
  C14---C19               1.403 (6)    C39---C40               1.411 (5)
  C15---C16               1.397 (7)    C40---C41               1.382 (6)
  C15---N23               1.488 (7)    C40---N48               1.466 (5)
  C16---C17               1.361 (8)    C41---C42               1.375 (6)
  C16---H16               0.9500       C41---H41               0.9500
  C17---C18               1.377 (7)    C42---C43               1.378 (6)
  C17---H17               0.9500       C42---H42               0.9500
  C18---C19               1.378 (6)    C43---C44               1.375 (6)
  C18---H18               0.9500       C43---H43               0.9500
  C19---H19               0.9500       C44---H44               0.9500
  C20---O21               1.197 (5)    C45---O46               1.191 (5)
  C20---C22               1.489 (5)    C45---C47               1.492 (6)
  C22---H22A              0.9800       C47---H47A              0.9800
  C22---H22B              0.9800       C47---H47B              0.9800
  C22---H22C              0.9800       C47---H47C              0.9800
  N23---O25               1.207 (6)    N48---O49               1.222 (5)
  N23---O24               1.215 (7)    N48---O50               1.226 (5)
                                                               
  C2---C1---C14           126.4 (4)    C27---C26---C39         123.9 (3)
  C2---C1---H1            116.8        C27---C26---H26         118.0
  C14---C1---H1           116.8        C39---C26---H26         118.0
  C1---C2---C6            123.9 (3)    C26---C27---C31         124.9 (3)
  C1---C2---H2            118.0        C26---C27---H27         117.6
  C6---C2---H2            118.0        C31---C27---H27         117.6
  C4---C3---C8            117.0 (4)    C33---C28---C34         123.4 (3)
  C4---C3---C9            119.7 (4)    C33---C28---C29         116.3 (3)
  C8---C3---C9            123.4 (4)    C34---C28---C29         120.2 (3)
  N5---C4---C3            123.8 (3)    N30---C29---C28         124.1 (3)
  N5---C4---C12           118.4 (3)    N30---C29---C37         118.4 (3)
  C3---C4---C12           117.8 (3)    C28---C29---C37         117.5 (3)
  C6---N5---C4            117.6 (3)    C31---N30---C29         117.1 (3)
  N5---C6---C7            122.2 (4)    N30---C31---C32         122.9 (3)
  N5---C6---C2            118.0 (3)    N30---C31---C27         119.4 (3)
  C7---C6---C2            119.8 (3)    C32---C31---C27         117.7 (3)
  C8---C7---C6            120.6 (4)    C33---C32---C31         119.7 (4)
  C8---C7---H7            119.7        C33---C32---H32         120.2
  C6---C7---H7            119.7        C31---C32---H32         120.2
  C7---C8---C3            118.9 (4)    C32---C33---C28         119.9 (3)
  C7---C8---H8            120.6        C32---C33---H33         120.1
  C3---C8---H8            120.6        C28---C33---H33         120.1
  C10---C9---C3           120.2 (4)    C35---C34---C28         119.9 (4)
  C10---C9---H9           119.9        C35---C34---H34         120.1
  C3---C9---H9            119.9        C28---C34---H34         120.1
  C9---C10---C11          120.9 (4)    C34---C35---C36         121.2 (4)
  C9---C10---H10          119.5        C34---C35---H35         119.4
  C11---C10---H10         119.5        C36---C35---H35         119.4
  C12---C11---C10         119.4 (4)    C37---C36---C35         119.3 (4)
  C12---C11---H11         120.3        C37---C36---H36         120.3
  C10---C11---H11         120.3        C35---C36---H36         120.3
  C11---C12---O13         119.7 (3)    C36---C37---O38         120.1 (3)
  C11---C12---C4          121.9 (4)    C36---C37---C29         121.8 (3)
  O13---C12---C4          118.3 (3)    O38---C37---C29         117.9 (3)
  C20---O13---C12         117.2 (3)    C45---O38---C37         117.0 (3)
  C15---C14---C19         115.6 (4)    C44---C39---C40         114.9 (3)
  C15---C14---C1          123.2 (4)    C44---C39---C26         120.8 (3)
  C19---C14---C1          121.2 (4)    C40---C39---C26         124.2 (3)
  C14---C15---C16         123.1 (5)    C41---C40---C39         123.3 (4)
  C14---C15---N23         119.8 (4)    C41---C40---N48         115.3 (3)
  C16---C15---N23         117.2 (4)    C39---C40---N48         121.3 (3)
  C17---C16---C15         119.2 (4)    C42---C41---C40         119.0 (4)
  C17---C16---H16         120.4        C42---C41---H41         120.5
  C15---C16---H16         120.4        C40---C41---H41         120.5
  C16---C17---C18         119.8 (4)    C41---C42---C43         119.8 (4)
  C16---C17---H17         120.1        C41---C42---H42         120.1
  C18---C17---H17         120.1        C43---C42---H42         120.1
  C17---C18---C19         120.6 (5)    C44---C43---C42         120.7 (4)
  C17---C18---H18         119.7        C44---C43---H43         119.7
  C19---C18---H18         119.7        C42---C43---H43         119.7
  C18---C19---C14         121.7 (4)    C43---C44---C39         122.2 (4)
  C18---C19---H19         119.2        C43---C44---H44         118.9
  C14---C19---H19         119.2        C39---C44---H44         118.9
  O21---C20---O13         122.2 (4)    O46---C45---O38         122.7 (4)
  O21---C20---C22         126.8 (4)    O46---C45---C47         126.4 (4)
  O13---C20---C22         111.0 (3)    O38---C45---C47         110.9 (4)
  C20---C22---H22A        109.5        C45---C47---H47A        109.5
  C20---C22---H22B        109.5        C45---C47---H47B        109.5
  H22A---C22---H22B       109.5        H47A---C47---H47B       109.5
  C20---C22---H22C        109.5        C45---C47---H47C        109.5
  H22A---C22---H22C       109.5        H47A---C47---H47C       109.5
  H22B---C22---H22C       109.5        H47B---C47---H47C       109.5
  O25---N23---O24         125.6 (7)    O49---N48---O50         123.8 (4)
  O25---N23---C15         115.0 (7)    O49---N48---C40         118.9 (4)
  O24---N23---C15         119.3 (4)    O50---N48---C40         117.3 (4)
                                                               
  C14---C1---C2---C6      179.3 (4)    C39---C26---C27---C31   177.4 (4)
  C8---C3---C4---N5       1.8 (6)      C33---C28---C29---N30   2.0 (6)
  C9---C3---C4---N5       −177.5 (4)   C34---C28---C29---N30   −178.1 (4)
  C8---C3---C4---C12      −176.9 (4)   C33---C28---C29---C37   −177.3 (4)
  C9---C3---C4---C12      3.8 (6)      C34---C28---C29---C37   2.6 (5)
  C3---C4---N5---C6       0.1 (6)      C28---C29---N30---C31   −0.7 (6)
  C12---C4---N5---C6      178.8 (3)    C37---C29---N30---C31   178.7 (4)
  C4---N5---C6---C7       −2.5 (6)     C29---N30---C31---C32   −1.6 (6)
  C4---N5---C6---C2       178.7 (3)    C29---N30---C31---C27   −179.5 (3)
  C1---C2---C6---N5       0.9 (6)      C26---C27---C31---N30   0.9 (7)
  C1---C2---C6---C7       −178.0 (4)   C26---C27---C31---C32   −177.2 (4)
  N5---C6---C7---C8       2.9 (6)      N30---C31---C32---C33   2.3 (6)
  C2---C6---C7---C8       −178.2 (4)   C27---C31---C32---C33   −179.7 (4)
  C6---C7---C8---C3       −0.9 (6)     C31---C32---C33---C28   −0.8 (7)
  C4---C3---C8---C7       −1.3 (6)     C34---C28---C33---C32   178.9 (4)
  C9---C3---C8---C7       178.0 (4)    C29---C28---C33---C32   −1.2 (6)
  C4---C3---C9---C10      −1.2 (7)     C33---C28---C34---C35   179.6 (4)
  C8---C3---C9---C10      179.5 (4)    C29---C28---C34---C35   −0.4 (6)
  C3---C9---C10---C11     −1.2 (7)     C28---C34---C35---C36   −0.9 (6)
  C9---C10---C11---C12    0.9 (7)      C34---C35---C36---C37   −0.3 (6)
  C10---C11---C12---O13   176.9 (4)    C35---C36---C37---O38   176.8 (4)
  C10---C11---C12---C4    1.8 (6)      C35---C36---C37---C29   2.7 (6)
  N5---C4---C12---C11     177.1 (4)    N30---C29---C37---C36   176.8 (4)
  C3---C4---C12---C11     −4.1 (6)     C28---C29---C37---C36   −3.8 (6)
  N5---C4---C12---O13     2.0 (6)      N30---C29---C37---O38   2.5 (5)
  C3---C4---C12---O13     −179.3 (3)   C28---C29---C37---O38   −178.1 (3)
  C11---C12---O13---C20   111.1 (4)    C36---C37---O38---C45   113.4 (4)
  C4---C12---O13---C20    −73.7 (4)    C29---C37---O38---C45   −72.2 (4)
  C2---C1---C14---C15     178.5 (4)    C27---C26---C39---C44   −7.5 (6)
  C2---C1---C14---C19     1.1 (7)      C27---C26---C39---C40   171.5 (4)
  C19---C14---C15---C16   2.1 (7)      C44---C39---C40---C41   1.3 (6)
  C1---C14---C15---C16    −175.4 (4)   C26---C39---C40---C41   −177.7 (4)
  C19---C14---C15---N23   −177.3 (4)   C44---C39---C40---N48   177.9 (4)
  C1---C14---C15---N23    5.2 (7)      C26---C39---C40---N48   −1.2 (6)
  C14---C15---C16---C17   −2.7 (8)     C39---C40---C41---C42   −3.1 (7)
  N23---C15---C16---C17   176.7 (5)    N48---C40---C41---C42   −179.8 (4)
  C15---C16---C17---C18   1.4 (8)      C40---C41---C42---C43   3.0 (8)
  C16---C17---C18---C19   0.4 (8)      C41---C42---C43---C44   −1.3 (8)
  C17---C18---C19---C14   −1.0 (7)     C42---C43---C44---C39   −0.4 (7)
  C15---C14---C19---C18   −0.3 (7)     C40---C39---C44---C43   0.4 (6)
  C1---C14---C19---C18    177.3 (4)    C26---C39---C44---C43   179.5 (4)
  C12---O13---C20---O21   −9.5 (5)     C37---O38---C45---O46   −13.8 (5)
  C12---O13---C20---C22   171.4 (3)    C37---O38---C45---C47   166.9 (3)
  C14---C15---N23---O25   −132.0 (5)   C41---C40---N48---O49   −140.5 (4)
  C16---C15---N23---O25   48.6 (7)     C39---C40---N48---O49   42.7 (6)
  C14---C15---N23---O24   51.4 (7)     C41---C40---N48---O50   37.9 (6)
  C16---C15---N23---O24   −128.0 (6)   C39---C40---N48---O50   −138.9 (4)
  ----------------------- ------------ ----------------------- ------------
