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

For hydrogen-bond motifs, see: Bernstein *et al.* (1995[@bb1]). For ring puckering parameters, see: Cremer & Pople (1975[@bb3]); Nardelli (1983[@bb5]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~21~H~14~N~2~O~5~*M* *~r~* = 374.34Monoclinic,*a* = 7.9191 (4) Å*b* = 23.3876 (11) Å*c* = 9.6199 (5) Åβ = 104.632 (2)°*V* = 1723.91 (15) Å^3^*Z* = 4Mo *K*α radiationμ = 0.11 mm^−1^*T* = 293 K0.33 × 0.27 × 0.25 mm

### Data collection {#sec2.1.2}

'Bruker Kappa APEXII CCD diffractometer'Absorption correction: multi-scan (*SADABS*; Bruker, 2004[@bb2]) *T* ~min~ = 0.897, *T* ~max~ = 0.97416263 measured reflections3023 independent reflections2334 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.032

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.036*wR*(*F* ^2^) = 0.102*S* = 1.003023 reflections253 parametersH-atom parameters constrainedΔρ~max~ = 0.12 e Å^−3^Δρ~min~ = −0.17 e Å^−3^

 {#d5e485}

Data collection: *APEX2* (Bruker, 2004[@bb2]); cell refinement: *APEX2* and *SAINT* (Bruker, 2004[@bb2]); data reduction: *SAINT* and *XPREP* (Bruker, 2004[@bb2]); program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb6]); molecular graphics: *ORTEP-3* (Farrugia, 1997[@bb4]); software used to prepare material for publication: *SHELXL97* and *PLATON* (Spek, 2009[@bb7])'.

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536809006023/bt2875sup1.cif](http://dx.doi.org/10.1107/S1600536809006023/bt2875sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809006023/bt2875Isup2.hkl](http://dx.doi.org/10.1107/S1600536809006023/bt2875Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?bt2875&file=bt2875sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?bt2875sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?bt2875&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [BT2875](http://scripts.iucr.org/cgi-bin/sendsup?bt2875)).

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help in collecting the X-ray intensity data. MNM and ASP thank Dr J. Jothi Kumar, Principal of Presidency College, Chennai, India, for providing the computer and internet facilities.

Comment
=======

A view of the title compound with the atom-numbering scheme is shown in Fig. 1. The bond lengths C1---O1 and C1---N1 in the oxazine ring are 1.344 (2) and 1.307 (2)Å respectively.

The six membered oxazine moiety is not planar, having a total puckering amplitude, Q~T~ of 0.329 (2) Å and adopting a boat conformation \[θ = 81.8 (1) and φ = 171.8 (2)°\] (Cremer & Pople, 1975), and the lowest displacement asymmetry parameters Δ~S~(O1) is 8.0 (1)° (Nardelli, 1983). The dihedral angle between the naphthalene and benzene ring is 89.2 (1)°.

The crystal structure of the title compound is characterized by bifurcated hydrogen bonds between the amine and aldehyde groups (Table 1 and Fig. 2). One interaction is an intramolecular N---H···O hydrogen bond between donor atom N1 and acceptor atom O4, described by the graph-set motif S(6) (Bernstein *et al.*, 1995). Atom N1 in the molecule at (*x*, *y*, *z*) also acts as a hydrogen-bond donor *via* atom H1 to atom O4 in the molecule at (1 - *x*, -*y*, -*z*). This intermolecular hydrogen bond links the molecules into dimers described by a graph-set motif *R*^2^~2~(12). The structure also contains C---H···O intermolecular interactions. Atom C11 and C18 in the molecule at (*x*, *y*, *z*) acts as a hydrogen-bond donor *via* atom H11 and H18 to atom O3 and O4 in the molecule at (2 - *x*, -*y*, 1 - *z*). This intermolecular hydrogen bond links the molecules into dimers with a cyclic *R*^2^~2~(20) and *R*^2^~2~(18) ring system, respectively.

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

To the solution containing *N*-\[(3-Nitro-phenyl)-(2-hydroxy-napthalen-1-yl) -methyl\]-acetamide (10 mmol) dissolved in DMF (12 equiv), POCl3 (8 eqiuv) was added slowly dropwise (around 15 min) at 273°K, then the reaction mixture was allowed to reach room temperature. The reaction mixture was stirred at 363°K for about 3.5 h. Afer completion of the reaction, it was allowed to cool to room temperature. Then it was poured into crushed ice and refrigerated overnight. The solution was neutralized with sodium acetate and the crude compound was extracted with dichloromethane (3 × 50 ml) and washed with water (3 × 25 ml). Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified through column chromatography using ethyl acetate: petroleum ether (1:1) as eluent. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in Ethanol.

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

All H atoms were positioned geometrically, with N---H = 0.86 and C---H = 0.93 and 0.98 Å aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with *U*~iso~(H) = *xU*~eq~(C, N), where *x* = 1.2 for all H atoms.

Figures
=======

![The molecular structure of (I), showing the atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.](e-65-0o582-fig1){#Fap1}

![The crystal packing of compound (I), showing the R22(12), R22(20) and R22(18) rings. Hydrogen bonding is shown as dashed lines. H atoms not involved in the hydrogen bonding have been omitted for clarity. \[Symmetry codes: (\*)-x + 2, -y, -z + 1, (\$)-x + 1, -y, -z\]](e-65-0o582-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~21~H~14~N~2~O~5~        *F*(000) = 776
  *M~r~* = 374.34           *D*~x~ = 1.442 Mg m^−3^
  Monoclinic, *P*2~1~/*n*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2yn       Cell parameters from 2334 reflections
  *a* = 7.9191 (4) Å        θ = 2.5--25°
  *b* = 23.3876 (11) Å      µ = 0.11 mm^−1^
  *c* = 9.6199 (5) Å        *T* = 293 K
  β = 104.632 (2)°          Block, colourless
  *V* = 1723.91 (15) Å^3^   0.33 × 0.27 × 0.25 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  \'Bruker Kappa APEXII CCD diffractometer\'                   3023 independent reflections
  Radiation source: fine-focus sealed tube                     2334 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.032
  ω and φ scan                                                 θ~max~ = 24.9°, θ~min~ = 2.8°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2004)   *h* = −9→9
  *T*~min~ = 0.897, *T*~max~ = 0.974                           *k* = −27→27
  16263 measured reflections                                   *l* = −11→11
  ------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.036   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.102                  H-atom parameters constrained
  *S* = 1.00                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0509*P*)^2^ + 0.352*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3023 reflections                      (Δ/σ)~max~ \< 0.001
  253 parameters                        Δρ~max~ = 0.12 e Å^−3^
  0 restraints                          Δρ~min~ = −0.17 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

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

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All e.s.d.\'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.\'s are taken into account individually in the estimation of e.s.d.\'s in distances, angles and torsion angles; correlations between e.s.d.\'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.\'s is used for estimating e.s.d.\'s involving l.s. planes.
  Refinement. Refinement of *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*- factors based on ALL data will be even larger.
  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ----- --------------- -------------- --------------- -------------------- --
        *x*             *y*            *z*             *U*~iso~\*/*U*~eq~   
  O1    0.30114 (13)    0.16841 (5)    0.13932 (12)    0.0486 (3)           
  O2    0.8553 (2)      −0.07387 (6)   0.43720 (18)    0.0878 (5)           
  O3    0.8486 (3)      −0.07086 (8)   0.6565 (2)      0.1195 (7)           
  O4    0.30819 (17)    0.00916 (5)    −0.05620 (14)   0.0638 (4)           
  O5    −0.14205 (16)   0.09772 (6)    −0.06754 (16)   0.0718 (4)           
  N1    0.47317 (16)    0.09268 (5)    0.11444 (13)    0.0418 (3)           
  H1    0.4847          0.0619         0.0690          0.050\*              
  N2    0.8208 (2)      −0.04987 (7)   0.53794 (19)    0.0637 (4)           
  C1    0.3180 (2)      0.11583 (6)    0.08808 (16)    0.0401 (4)           
  C2    0.62913 (19)    0.11553 (6)    0.21612 (16)    0.0388 (4)           
  H2    0.7310          0.1063         0.1799          0.047\*              
  C3    0.61165 (19)    0.17956 (6)    0.21877 (16)    0.0395 (4)           
  C4    0.45014 (19)    0.20287 (6)    0.18043 (17)    0.0412 (4)           
  C5    0.4178 (2)      0.26167 (7)    0.17688 (17)    0.0464 (4)           
  H5    0.3042          0.2757         0.1503          0.056\*              
  C6    0.5556 (2)      0.29776 (7)    0.21305 (18)    0.0485 (4)           
  H6    0.5363          0.3370         0.2088          0.058\*              
  C7    0.7285 (2)      0.27682 (7)    0.25716 (17)    0.0439 (4)           
  C8    0.8737 (2)      0.31383 (8)    0.29883 (19)    0.0529 (4)           
  H8    0.8562          0.3532         0.2938          0.063\*              
  C9    1.0376 (2)      0.29305 (8)    0.3459 (2)      0.0576 (5)           
  H9    1.1313          0.3181         0.3739          0.069\*              
  C10   1.0666 (2)      0.23391 (8)    0.35255 (19)    0.0555 (5)           
  H10   1.1796          0.2199         0.3856          0.067\*              
  C11   0.9305 (2)      0.19657 (7)    0.31089 (17)    0.0474 (4)           
  H11   0.9518          0.1574         0.3150          0.057\*              
  C12   0.7579 (2)      0.21687 (7)    0.26167 (16)    0.0402 (4)           
  C13   0.65335 (18)    0.08758 (6)    0.36265 (16)    0.0370 (3)           
  C14   0.6049 (2)      0.11392 (7)    0.47526 (18)    0.0504 (4)           
  H14   0.5557          0.1503         0.4621          0.061\*              
  C15   0.6281 (2)      0.08734 (8)    0.60702 (19)    0.0590 (5)           
  H15   0.5947          0.1060         0.6812          0.071\*              
  C16   0.6998 (2)      0.03369 (8)    0.62976 (18)    0.0510 (4)           
  H16   0.7172          0.0157         0.7184          0.061\*              
  C17   0.7447 (2)      0.00769 (7)    0.51666 (18)    0.0441 (4)           
  C18   0.72429 (19)    0.03325 (7)    0.38466 (17)    0.0410 (4)           
  H18   0.7578          0.0142         0.3110          0.049\*              
  C19   0.1647 (2)      0.08978 (7)    0.00800 (16)    0.0425 (4)           
  C20   −0.0008 (2)     0.11766 (8)    −0.00797 (18)   0.0525 (4)           
  H20   0.0004          0.1542         0.0307          0.063\*              
  C21   0.1741 (2)      0.03622 (8)    −0.05856 (18)   0.0529 (4)           
  H21   0.0691          0.0200         −0.1087         0.063\*              
  ----- --------------- -------------- --------------- -------------------- --

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

  ----- ------------- ------------- ------------- ------------- ------------- -------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^       *U*^13^       *U*^23^
  O1    0.0428 (6)    0.0418 (7)    0.0611 (7)    −0.0005 (5)   0.0128 (5)    −0.0115 (5)
  O2    0.1298 (13)   0.0574 (9)    0.0767 (11)   0.0390 (9)    0.0270 (10)   0.0026 (8)
  O3    0.1869 (19)   0.1002 (13)   0.0839 (12)   0.0799 (13)   0.0572 (12)   0.0540 (10)
  O4    0.0610 (8)    0.0556 (8)    0.0703 (9)    0.0025 (6)    0.0082 (6)    −0.0219 (6)
  O5    0.0463 (7)    0.0827 (10)   0.0801 (10)   −0.0028 (7)   0.0041 (7)    −0.0112 (8)
  N1    0.0474 (8)    0.0357 (7)    0.0391 (7)    0.0028 (6)    0.0050 (6)    −0.0071 (6)
  N2    0.0758 (10)   0.0516 (9)    0.0642 (11)   0.0201 (8)    0.0189 (8)    0.0122 (8)
  C1    0.0477 (9)    0.0381 (9)    0.0355 (8)    0.0008 (7)    0.0123 (7)    −0.0007 (7)
  C2    0.0400 (8)    0.0348 (8)    0.0408 (9)    0.0007 (6)    0.0089 (7)    −0.0045 (7)
  C3    0.0466 (9)    0.0352 (8)    0.0369 (8)    0.0012 (7)    0.0111 (7)    −0.0008 (7)
  C4    0.0447 (9)    0.0375 (9)    0.0419 (9)    −0.0009 (7)   0.0116 (7)    −0.0032 (7)
  C5    0.0504 (9)    0.0402 (9)    0.0490 (10)   0.0084 (8)    0.0134 (8)    −0.0002 (7)
  C6    0.0645 (11)   0.0330 (9)    0.0511 (10)   0.0038 (8)    0.0202 (8)    0.0013 (7)
  C7    0.0582 (10)   0.0380 (9)    0.0392 (9)    −0.0041 (7)   0.0191 (7)    −0.0002 (7)
  C8    0.0672 (12)   0.0434 (10)   0.0530 (11)   −0.0129 (9)   0.0245 (9)    −0.0026 (8)
  C9    0.0598 (11)   0.0612 (12)   0.0553 (11)   −0.0230 (9)   0.0211 (9)    −0.0057 (9)
  C10   0.0486 (10)   0.0660 (12)   0.0531 (11)   −0.0078 (9)   0.0150 (8)    −0.0017 (9)
  C11   0.0491 (9)    0.0467 (10)   0.0470 (10)   −0.0016 (8)   0.0133 (8)    0.0000 (8)
  C12   0.0482 (9)    0.0386 (9)    0.0354 (8)    −0.0028 (7)   0.0136 (7)    −0.0010 (7)
  C13   0.0338 (7)    0.0342 (8)    0.0404 (8)    −0.0017 (6)   0.0044 (6)    −0.0046 (7)
  C14   0.0612 (11)   0.0413 (10)   0.0485 (10)   0.0106 (8)    0.0133 (8)    −0.0042 (8)
  C15   0.0745 (12)   0.0609 (12)   0.0441 (11)   0.0126 (10)   0.0197 (9)    −0.0063 (9)
  C16   0.0554 (10)   0.0559 (11)   0.0391 (9)    0.0020 (8)    0.0071 (7)    0.0031 (8)
  C17   0.0431 (9)    0.0396 (9)    0.0466 (10)   0.0042 (7)    0.0056 (7)    0.0025 (7)
  C18   0.0415 (8)    0.0389 (9)    0.0417 (9)    0.0028 (7)    0.0088 (7)    −0.0055 (7)
  C19   0.0448 (9)    0.0458 (10)   0.0362 (8)    −0.0034 (7)   0.0087 (7)    −0.0027 (7)
  C20   0.0488 (10)   0.0591 (11)   0.0482 (10)   −0.0017 (8)   0.0094 (8)    −0.0038 (8)
  C21   0.0511 (10)   0.0563 (11)   0.0482 (10)   −0.0069 (9)   0.0068 (8)    −0.0092 (8)
  ----- ------------- ------------- ------------- ------------- ------------- -------------

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

  ---------------------- -------------- ----------------------- --------------
  O1---C1                1.3440 (18)    C8---C9                 1.352 (3)
  O1---C4                1.4009 (18)    C8---H8                 0.9300
  O2---N2                1.209 (2)      C9---C10                1.401 (3)
  O3---N2                1.210 (2)      C9---H9                 0.9300
  O4---C21               1.232 (2)      C10---C11               1.366 (2)
  O5---C20               1.214 (2)      C10---H10               0.9300
  N1---C1                1.3075 (19)    C11---C12               1.411 (2)
  N1---C2                1.4689 (19)    C11---H11               0.9300
  N1---H1                0.8600         C13---C14               1.382 (2)
  N2---C17               1.468 (2)      C13---C18               1.384 (2)
  C1---C19               1.402 (2)      C14---C15               1.382 (3)
  C2---C3                1.505 (2)      C14---H14               0.9300
  C2---C13               1.521 (2)      C15---C16               1.372 (2)
  C2---H2                0.9800         C15---H15               0.9300
  C3---C4                1.353 (2)      C16---C17               1.370 (2)
  C3---C12               1.425 (2)      C16---H16               0.9300
  C4---C5                1.398 (2)      C17---C18               1.376 (2)
  C5---C6                1.354 (2)      C18---H18               0.9300
  C5---H5                0.9300         C19---C21               1.417 (2)
  C6---C7                1.414 (2)      C19---C20               1.437 (2)
  C6---H6                0.9300         C20---H20               0.9300
  C7---C8                1.414 (2)      C21---H21               0.9300
  C7---C12               1.420 (2)                              
                                                                
  C1---O1---C4           118.37 (12)    C11---C10---C9          120.65 (17)
  C1---N1---C2           124.71 (13)    C11---C10---H10         119.7
  C1---N1---H1           117.6          C9---C10---H10          119.7
  C2---N1---H1           117.6          C10---C11---C12         120.58 (16)
  O2---N2---O3           122.89 (17)    C10---C11---H11         119.7
  O2---N2---C17          118.80 (16)    C12---C11---H11         119.7
  O3---N2---C17          118.31 (17)    C11---C12---C7          118.71 (14)
  N1---C1---O1           118.90 (14)    C11---C12---C3          122.58 (14)
  N1---C1---C19          124.59 (14)    C7---C12---C3           118.70 (14)
  O1---C1---C19          116.51 (13)    C14---C13---C18         118.15 (15)
  N1---C2---C3           107.93 (12)    C14---C13---C2          122.67 (14)
  N1---C2---C13          110.41 (12)    C18---C13---C2          119.18 (13)
  C3---C2---C13          113.73 (12)    C13---C14---C15         121.30 (16)
  N1---C2---H2           108.2          C13---C14---H14         119.3
  C3---C2---H2           108.2          C15---C14---H14         119.3
  C13---C2---H2          108.2          C16---C15---C14         120.76 (16)
  C4---C3---C12          118.39 (14)    C16---C15---H15         119.6
  C4---C3---C2           118.75 (13)    C14---C15---H15         119.6
  C12---C3---C2          122.86 (13)    C17---C16---C15         117.36 (16)
  C3---C4---O1           121.07 (13)    C17---C16---H16         121.3
  C3---C4---C5           123.91 (15)    C15---C16---H16         121.3
  O1---C4---C5           115.02 (13)    C16---C17---C18         123.15 (15)
  C6---C5---C4           118.41 (15)    C16---C17---N2          118.43 (15)
  C6---C5---H5           120.8          C18---C17---N2          118.41 (15)
  C4---C5---H5           120.8          C17---C18---C13         119.26 (14)
  C5---C6---C7           121.19 (15)    C17---C18---H18         120.4
  C5---C6---H6           119.4          C13---C18---H18         120.4
  C7---C6---H6           119.4          C1---C19---C21          119.67 (15)
  C6---C7---C8           121.97 (15)    C1---C19---C20          120.10 (15)
  C6---C7---C12          119.34 (15)    C21---C19---C20         120.22 (15)
  C8---C7---C12          118.69 (15)    O5---C20---C19          125.67 (18)
  C9---C8---C7           121.21 (17)    O5---C20---H20          117.2
  C9---C8---H8           119.4          C19---C20---H20         117.2
  C7---C8---H8           119.4          O4---C21---C19          126.11 (16)
  C8---C9---C10          120.15 (16)    O4---C21---H21          116.9
  C8---C9---H9           119.9          C19---C21---H21         116.9
  C10---C9---H9          119.9                                  
                                                                
  C2---N1---C1---O1      10.5 (2)       C8---C7---C12---C3      −179.59 (14)
  C2---N1---C1---C19     −169.97 (14)   C4---C3---C12---C11     176.48 (15)
  C4---O1---C1---N1      18.7 (2)       C2---C3---C12---C11     −2.7 (2)
  C4---O1---C1---C19     −160.81 (13)   C4---C3---C12---C7      −2.3 (2)
  C1---N1---C2---C3      −31.1 (2)      C2---C3---C12---C7      178.44 (14)
  C1---N1---C2---C13     93.82 (17)     N1---C2---C13---C14     −100.41 (16)
  N1---C2---C3---C4      24.17 (19)     C3---C2---C13---C14     21.1 (2)
  C13---C2---C3---C4     −98.69 (16)    N1---C2---C13---C18     78.61 (16)
  N1---C2---C3---C12     −156.62 (13)   C3---C2---C13---C18     −159.90 (13)
  C13---C2---C3---C12    80.52 (17)     C18---C13---C14---C15   0.8 (2)
  C12---C3---C4---O1     −179.04 (13)   C2---C13---C14---C15    179.79 (16)
  C2---C3---C4---O1      0.2 (2)        C13---C14---C15---C16   −0.2 (3)
  C12---C3---C4---C5     1.6 (2)        C14---C15---C16---C17   −0.8 (3)
  C2---C3---C4---C5      −179.12 (15)   C15---C16---C17---C18   1.3 (3)
  C1---O1---C4---C3      −24.0 (2)      C15---C16---C17---N2    −179.66 (15)
  C1---O1---C4---C5      155.39 (14)    O2---N2---C17---C16     177.49 (18)
  C3---C4---C5---C6      0.4 (2)        O3---N2---C17---C16     −3.6 (3)
  O1---C4---C5---C6      −178.97 (14)   O2---N2---C17---C18     −3.4 (3)
  C4---C5---C6---C7      −1.7 (2)       O3---N2---C17---C18     175.53 (19)
  C5---C6---C7---C8      −178.35 (16)   C16---C17---C18---C13   −0.7 (2)
  C5---C6---C7---C12     0.9 (2)        N2---C17---C18---C13    −179.79 (14)
  C6---C7---C8---C9      177.48 (16)    C14---C13---C18---C17   −0.3 (2)
  C12---C7---C8---C9     −1.8 (2)       C2---C13---C18---C17    −179.37 (13)
  C7---C8---C9---C10     0.8 (3)        N1---C1---C19---C21     −4.3 (2)
  C8---C9---C10---C11    0.4 (3)        O1---C1---C19---C21     175.26 (14)
  C9---C10---C11---C12   −0.6 (3)       N1---C1---C19---C20     176.56 (15)
  C10---C11---C12---C7   −0.4 (2)       O1---C1---C19---C20     −3.9 (2)
  C10---C11---C12---C3   −179.22 (15)   C1---C19---C20---O5     −175.50 (17)
  C6---C7---C12---C11    −177.72 (14)   C21---C19---C20---O5    5.3 (3)
  C8---C7---C12---C11    1.5 (2)        C1---C19---C21---O4     −1.5 (3)
  C6---C7---C12---C3     1.2 (2)        C20---C19---C21---O4    177.67 (17)
  ---------------------- -------------- ----------------------- --------------

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

  -------------------- --------- --------- ----------- ---------------
  *D*---H···*A*        *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C11---H11···O3^i^    0.93      2.54      3.395 (2)   153
  C18---H18···O4^ii^   0.93      2.44      3.259 (2)   148
  N1---H1···O4^ii^     0.86      2.36      3.078 (2)   141
  N1---H1···O4         0.86      2.02      2.670 (2)   132
  C20---H20···O1       0.93      2.37      2.724 (2)   102
  -------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*        *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------ --------- ------- ----------- -------------
  C11---H11⋯O3^i^    0.93      2.54    3.395 (2)   153
  C18---H18⋯O4^ii^   0.93      2.44    3.259 (2)   148
  N1---H1⋯O4^ii^     0.86      2.36    3.078 (2)   141
  N1---H1⋯O4         0.86      2.02    2.670 (2)   132

Symmetry codes: (i) ; (ii) .
