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

For the biological activity of some heterocyclic derivatives containing the 4*H*-pyran unit, see: Elnagdi *et al.* ( 1983[@bb4]); Goldmann & Stoltefus (1991[@bb7]); Perez-Perez *et al.* ( 1995[@bb8]); Fan *et al.* ( 2010[@bb5]); Aytemir *et al.* ( 2004[@bb3]); Uher *et al.* ( 1994[@bb12]).  For similar structures, see: Akkurt *et al.* ( 2013[@bb2], 2015[@bb1]). 

Experimental   {#sec2}
==============

Crystal data   {#sec2.1}
--------------

C~20~H~14~N~2~O~2~*M* *~r~* = 314.33Monoclinic,*a* = 12.1086 (8) Å*b* = 13.1418 (9) Å*c* = 10.1552 (7) Åβ = 96.992 (1)°*V* = 1603.97 (19) Å^3^*Z* = 4Mo *K*α radiationμ = 0.09 mm^−1^*T* = 100 K0.21 × 0.08 × 0.07 mm

Data collection   {#sec2.2}
-----------------

Rigaku AFC12 (Right) diffractometerAbsorption correction: multi-scan (*CrystalClear-SM Expert*; Rigaku, 2012[@bb9]) *T* ~min~ = 0.738, *T* ~max~ = 1.00017411 measured reflections3679 independent reflections3251 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.030

Refinement   {#sec2.3}
------------

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.034*wR*(*F* ^2^) = 0.092*S* = 1.063679 reflections229 parameters3 restraintsH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.26 e Å^−3^Δρ~min~ = −0.18 e Å^−3^

 {#d5e551}

Data collection: *CrystalClear-SM Expert* (Rigaku, 2012[@bb9]); cell refinement: *CrystalClear-SM Expert*; data reduction: *CrystalClear-SM Expert*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL2012* (Sheldrick, 2015[@bb11]); molecular graphics: *ORTEP-3 for Windows* (Farrugia, 2012[@bb6]); software used to prepare material for publication: *WinGX* (Farrugia, 2012[@bb6]). 

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

Crystal structure: contains datablock(s) I. DOI: [10.1107/S2056989015012566/tk5372sup1.cif](http://dx.doi.org/10.1107/S2056989015012566/tk5372sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S2056989015012566/tk5372Isup2.hkl](http://dx.doi.org/10.1107/S2056989015012566/tk5372Isup2.hkl)

###### 

Click here for additional data file. 

Supporting information file.  DOI: [10.1107/S2056989015012566/tk5372Isup3.cml](http://dx.doi.org/10.1107/S2056989015012566/tk5372Isup3.cml)

###### 

Click here for additional data file. 

.  DOI: [10.1107/S2056989015012566/tk5372fig1.tif](http://dx.doi.org/10.1107/S2056989015012566/tk5372fig1.tif)

View of the title compound with the atom-numbering scheme.  Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. 

###### 

Click here for additional data file. 

a .  DOI: [10.1107/S2056989015012566/tk5372fig2.tif](http://dx.doi.org/10.1107/S2056989015012566/tk5372fig2.tif)

View of the packing of the title compound viewing down *a* axis. 

CCDC reference: [1409621](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1409621)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?tk5372&file=tk5372sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?tk5372sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?tk5372&checkcif=yes)

Supporting information for this paper is available from the IUCr electronic archives (Reference: [TK5372](http://scripts.iucr.org/cgi-bin/sendsup?tk5372)). 

The authors would like to express their thanks to National Crystallography Service (NCS), Southampton, UK, for providing the X-ray data. 

S1.  Comment {#comment}
===========

During the last decade, 4*H*-pyrans have held a unique role in medicinal chemistry due to their biological and pharmacological activities (Elnagdi *et al.*,  1983; Goldmann & Stoltefus, 1991).  Fused pyran derivatives also exhibit a wide spectrum of biological and pharmacological properties, such as antiviral and antileishmanial (Perez-Perez *et al.*,  1995; Fan *et al.*,  2010), anticonvulsant and antimicrobial (Aytemir *et al.*,  2004) and insecticidal (Uher *et al.*,  1994).  In this context we report in this study the synthesis and crystal structural determination for the title compound. 

In the title compound (Fig.  1), the hydroxy-benzene ring (C15--C20) is approximately perpendicular to the naphthalene ring system \[C4--C13, maximum deviation = -0.017 (1) Å at atom C13\] as indicated by the dihedral angle of 85.56 (4)°.  The 4*H*-pyran ring (O1/C1--C4/C13) in the title compound is puckered with the puckering parameters of Q~T~ = 0.199 (1) Å, θ = 102.9 (3) ° and φ = 354.2 (3) °.  The bond lengths and angles in the title compound are within normal ranges and comparable with those reported for the similar structures (Akkurt *et al.*,  2013; 2015). 

In the crystal structure, molecules are linked by N---H···O and O---H···N hydrogen bonds (Table 1, Fig.  2), which leads to a layer in the *bc* plane. 

S2.  Experimental {#experimental}
================

The title compound was obtained in 95% yield from the reaction of 2-naphthol (144 mg; 1 mmol) and an equimolar amount of 4-hydroxybenzylidene-malononitrile (180 mg; 1 mmol) in absolute ethanol (10 ml ) in the presence of a catalytic amount of piperidine under reflux for 3 h. Crystallization of the crude product from ethanol gave colourless crystals of the title compound suitable for X-ray crystallography·M.pt: 521 K.

S3.  Refinement {#refinement}
==============

The H atoms of the OH and NH~2~ group were located in a difference Fourier map and were refined freely \[N1---H1N = 0.896 (12) Å, N1---H2N = 0.883 (12) Å and O2---H2O = 0.885 (13) Å\].  The H atoms attached to the C atoms were positioned geometrically, with C---H = 0.95 Å and C---H = 1.00 Å for aromatic and methine H, respectively, and with *U*~iso~(H) = 1.2*U*~eq~(C). 

Figures
=======

![ View of the title compound with the atom-numbering scheme.  Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.](e-71-0o536-fig1){#Fap1}

![ View of the packing of the title compound viewing down a axis.](e-71-0o536-fig2){#Fap2}

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

  ------------------------- ----------------------------------------
  C~20~H~14~N~2~O~2~        *F*(000) = 656
  *M~r~* = 314.33           *D*~x~ = 1.302 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71075 Å
  *a* = 12.1086 (8) Å       Cell parameters from 17749 reflections
  *b* = 13.1418 (9) Å       θ = 2.3--27.5°
  *c* = 10.1552 (7) Å       µ = 0.09 mm^−1^
  β = 96.992 (1)°           *T* = 100 K
  *V* = 1603.97 (19) Å^3^   Blade, colourless
  *Z* = 4                   0.21 × 0.08 × 0.07 mm
  ------------------------- ----------------------------------------

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

  ---------------------------------------------------------------------------- --------------------------------------
  Rigaku AFC12 (Right) diffractometer                                          3679 independent reflections
  Radiation source: Rotating Anode                                             3251 reflections with *I* \> 2σ(*I*)
  Detector resolution: 28.5714 pixels mm^-1^                                   *R*~int~ = 0.030
  profile data from ω--scans                                                   θ~max~ = 27.5°, θ~min~ = 2.9°
  Absorption correction: multi-scan (*CrystalClear-SM Expert*; Rigaku, 2012)   *h* = −15→15
  *T*~min~ = 0.738, *T*~max~ = 1.000                                           *k* = −17→14
  17411 measured reflections                                                   *l* = −12→13
  ---------------------------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  3 restraints
  Least-squares matrix: full            Hydrogen site location: mixed
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.034   H atoms treated by a mixture of independent and constrained refinement
  *wR*(*F*^2^) = 0.092                  *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0425*P*)^2^ + 0.4007*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.06                            (Δ/σ)~max~ = 0.001
  3679 reflections                      Δρ~max~ = 0.26 e Å^−3^
  229 parameters                        Δρ~min~ = −0.18 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. 
  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

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

  ----- -------------- -------------- -------------- -------------------- --
        *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  C1    0.33983 (8)    0.47639 (8)    1.11802 (10)   0.0237 (2)           
  C2    0.31777 (8)    0.53512 (7)    1.00751 (9)    0.0225 (2)           
  C3    0.22804 (8)    0.50920 (7)    0.89492 (9)    0.02158 (19)         
  H3    0.1865         0.5730         0.8672         0.026\*              
  C4    0.14741 (8)    0.43453 (7)    0.94430 (10)   0.0234 (2)           
  C5    0.04093 (8)    0.41495 (8)    0.87013 (10)   0.0261 (2)           
  C6    0.00288 (9)    0.46750 (8)    0.75126 (11)   0.0295 (2)           
  H6    0.0494         0.5170         0.7178         0.035\*              
  C7    −0.10048 (9)   0.44795 (9)    0.68361 (12)   0.0356 (3)           
  H7    −0.1250        0.4847         0.6049         0.043\*              
  C8    −0.17001 (9)   0.37399 (10)   0.73009 (13)   0.0380 (3)           
  H8    −0.2408        0.3603         0.6822         0.046\*              
  C9    −0.13586 (9)   0.32188 (9)    0.84389 (13)   0.0363 (3)           
  H9    −0.1836        0.2722         0.8747         0.044\*              
  C10   −0.03025 (9)   0.34047 (8)    0.91728 (11)   0.0300 (2)           
  C11   0.00527 (9)    0.28765 (9)    1.03649 (12)   0.0348 (3)           
  H11   −0.0417        0.2374         1.0675         0.042\*              
  C12   0.10573 (9)    0.30770 (8)    1.10727 (12)   0.0325 (2)           
  H12   0.1287         0.2723         1.1875         0.039\*              
  C13   0.17513 (8)    0.38188 (8)    1.05958 (10)   0.0256 (2)           
  C14   0.38247 (9)    0.62331 (8)    0.99791 (10)   0.0264 (2)           
  C15   0.27956 (8)    0.46801 (7)    0.77552 (9)    0.02106 (19)         
  C16   0.32470 (8)    0.37029 (7)    0.77790 (10)   0.0233 (2)           
  H16   0.3201         0.3280         0.8529         0.028\*              
  C17   0.37626 (8)    0.33360 (7)    0.67264 (10)   0.0237 (2)           
  H17   0.4067         0.2669         0.6758         0.028\*              
  C18   0.38308 (8)    0.39533 (8)    0.56223 (9)    0.0235 (2)           
  C19   0.33979 (9)    0.49308 (8)    0.55907 (10)   0.0272 (2)           
  H19   0.3453         0.5357         0.4846         0.033\*              
  C20   0.28830 (8)    0.52852 (8)    0.66516 (10)   0.0255 (2)           
  H20   0.2585         0.5955         0.6622         0.031\*              
  N1    0.42225 (8)    0.48875 (8)    1.21728 (9)    0.0297 (2)           
  N2    0.43322 (9)    0.69661 (8)    0.99112 (10)   0.0383 (2)           
  O1    0.27537 (6)    0.39555 (6)    1.14083 (7)    0.02776 (17)         
  O2    0.43199 (7)    0.36270 (6)    0.45510 (7)    0.02998 (18)         
  H1N   0.4259 (12)    0.4453 (10)    1.2856 (13)    0.042 (4)\*          
  H2N   0.4767 (11)    0.5317 (10)    1.2069 (14)    0.041 (4)\*          
  H2O   0.4737 (13)    0.3086 (11)    0.4770 (16)    0.057 (5)\*          
  ----- -------------- -------------- -------------- -------------------- --

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

  ----- ------------ ------------ ------------ ------------- ------------ -------------
        *U*^11^      *U*^22^      *U*^33^      *U*^12^       *U*^13^      *U*^23^
  C1    0.0230 (5)   0.0260 (5)   0.0232 (5)   0.0009 (4)    0.0073 (4)   −0.0010 (4)
  C2    0.0224 (5)   0.0251 (5)   0.0207 (4)   −0.0014 (4)   0.0050 (3)   −0.0007 (4)
  C3    0.0210 (4)   0.0223 (4)   0.0217 (4)   0.0009 (3)    0.0037 (3)   0.0003 (3)
  C4    0.0221 (5)   0.0226 (5)   0.0266 (5)   0.0006 (4)    0.0074 (4)   −0.0028 (4)
  C5    0.0226 (5)   0.0257 (5)   0.0312 (5)   0.0012 (4)    0.0080 (4)   −0.0073 (4)
  C6    0.0246 (5)   0.0322 (5)   0.0318 (5)   0.0016 (4)    0.0040 (4)   −0.0067 (4)
  C7    0.0281 (5)   0.0410 (6)   0.0370 (6)   0.0051 (5)    0.0009 (4)   −0.0108 (5)
  C8    0.0223 (5)   0.0430 (7)   0.0483 (7)   0.0012 (5)    0.0022 (5)   −0.0184 (5)
  C9    0.0251 (5)   0.0330 (6)   0.0529 (7)   −0.0045 (4)   0.0130 (5)   −0.0159 (5)
  C10   0.0249 (5)   0.0266 (5)   0.0405 (6)   −0.0014 (4)   0.0116 (4)   −0.0089 (4)
  C11   0.0317 (5)   0.0279 (5)   0.0477 (7)   −0.0057 (4)   0.0164 (5)   −0.0007 (5)
  C12   0.0338 (6)   0.0287 (5)   0.0370 (6)   −0.0008 (4)   0.0119 (5)   0.0051 (4)
  C13   0.0237 (5)   0.0250 (5)   0.0293 (5)   0.0004 (4)    0.0075 (4)   −0.0004 (4)
  C14   0.0277 (5)   0.0328 (5)   0.0189 (4)   −0.0026 (4)   0.0035 (4)   0.0001 (4)
  C15   0.0190 (4)   0.0237 (5)   0.0204 (4)   −0.0002 (3)   0.0020 (3)   −0.0005 (3)
  C16   0.0251 (5)   0.0232 (5)   0.0221 (4)   −0.0006 (4)   0.0046 (4)   0.0033 (4)
  C17   0.0251 (5)   0.0206 (4)   0.0258 (5)   0.0017 (4)    0.0045 (4)   0.0009 (4)
  C18   0.0224 (4)   0.0285 (5)   0.0196 (4)   0.0012 (4)    0.0032 (3)   −0.0011 (4)
  C19   0.0308 (5)   0.0294 (5)   0.0215 (5)   0.0051 (4)    0.0045 (4)   0.0067 (4)
  C20   0.0279 (5)   0.0238 (5)   0.0249 (5)   0.0058 (4)    0.0039 (4)   0.0033 (4)
  N1    0.0284 (5)   0.0386 (5)   0.0218 (4)   −0.0026 (4)   0.0020 (3)   0.0042 (4)
  N2    0.0448 (6)   0.0404 (6)   0.0292 (5)   −0.0161 (5)   0.0028 (4)   0.0030 (4)
  O1    0.0269 (4)   0.0280 (4)   0.0285 (4)   −0.0009 (3)   0.0036 (3)   0.0063 (3)
  O2    0.0364 (4)   0.0326 (4)   0.0223 (4)   0.0095 (3)    0.0091 (3)   0.0022 (3)
  ----- ------------ ------------ ------------ ------------- ------------ -------------

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

  --------------------- -------------- ----------------------- --------------
  C1---N1               1.3393 (13)    C11---C12               1.3612 (17)
  C1---O1               1.3548 (12)    C11---H11               0.9500
  C1---C2               1.3614 (14)    C12---C13               1.4108 (14)
  C2---C14              1.4089 (14)    C12---H12               0.9500
  C2---C3               1.5171 (13)    C13---O1                1.3937 (12)
  C3---C4               1.5122 (13)    C14---N2                1.1492 (14)
  C3---C15              1.5286 (13)    C15---C20               1.3887 (13)
  C3---H3               1.0000         C15---C16               1.3948 (13)
  C4---C13              1.3661 (14)    C16---C17               1.3883 (13)
  C4---C5               1.4351 (14)    C16---H16               0.9500
  C5---C6               1.4180 (15)    C17---C18               1.3945 (13)
  C5---C10              1.4250 (15)    C17---H17               0.9500
  C6---C7               1.3765 (15)    C18---O2                1.3693 (11)
  C6---H6               0.9500         C18---C19               1.3864 (14)
  C7---C8               1.4047 (18)    C19---C20               1.3892 (14)
  C7---H7               0.9500         C19---H19               0.9500
  C8---C9               1.3636 (19)    C20---H20               0.9500
  C8---H8               0.9500         N1---H1N                0.896 (12)
  C9---C10              1.4207 (15)    N1---H2N                0.883 (12)
  C9---H9               0.9500         O2---H2O                0.885 (13)
  C10---C11             1.4162 (17)                            
                                                               
  N1---C1---O1          111.01 (9)     C12---C11---C10         121.03 (10)
  N1---C1---C2          127.23 (10)    C12---C11---H11         119.5
  O1---C1---C2          121.75 (9)     C10---C11---H11         119.5
  C1---C2---C14         117.94 (9)     C11---C12---C13         118.93 (10)
  C1---C2---C3          122.99 (9)     C11---C12---H12         120.5
  C14---C2---C3         119.07 (8)     C13---C12---H12         120.5
  C4---C3---C2          109.14 (8)     C4---C13---O1           123.20 (9)
  C4---C3---C15         112.06 (8)     C4---C13---C12          123.35 (10)
  C2---C3---C15         110.69 (8)     O1---C13---C12          113.46 (9)
  C4---C3---H3          108.3          N2---C14---C2           178.35 (12)
  C2---C3---H3          108.3          C20---C15---C16         118.23 (9)
  C15---C3---H3         108.3          C20---C15---C3          121.06 (8)
  C13---C4---C5         118.06 (9)     C16---C15---C3          120.61 (8)
  C13---C4---C3         120.77 (9)     C17---C16---C15         121.23 (9)
  C5---C4---C3          121.16 (9)     C17---C16---H16         119.4
  C6---C5---C10         118.25 (10)    C15---C16---H16         119.4
  C6---C5---C4          122.52 (10)    C16---C17---C18         119.55 (9)
  C10---C5---C4         119.23 (10)    C16---C17---H17         120.2
  C7---C6---C5          121.03 (11)    C18---C17---H17         120.2
  C7---C6---H6          119.5          O2---C18---C19          118.08 (9)
  C5---C6---H6          119.5          O2---C18---C17          122.03 (9)
  C6---C7---C8          120.47 (12)    C19---C18---C17         119.90 (9)
  C6---C7---H7          119.8          C18---C19---C20         119.79 (9)
  C8---C7---H7          119.8          C18---C19---H19         120.1
  C9---C8---C7          120.00 (11)    C20---C19---H19         120.1
  C9---C8---H8          120.0          C15---C20---C19         121.29 (9)
  C7---C8---H8          120.0          C15---C20---H20         119.4
  C8---C9---C10         121.26 (11)    C19---C20---H20         119.4
  C8---C9---H9          119.4          C1---N1---H1N           117.9 (9)
  C10---C9---H9         119.4          C1---N1---H2N           119.1 (9)
  C11---C10---C9        121.63 (10)    H1N---N1---H2N          122.1 (13)
  C11---C10---C5        119.39 (10)    C1---O1---C13           118.57 (8)
  C9---C10---C5         118.98 (11)    C18---O2---H2O          109.9 (11)
                                                               
  N1---C1---C2---C14    −4.87 (16)     C9---C10---C11---C12    −178.64 (10)
  O1---C1---C2---C14    173.97 (9)     C5---C10---C11---C12    0.69 (16)
  N1---C1---C2---C3     174.55 (9)     C10---C11---C12---C13   −0.47 (17)
  O1---C1---C2---C3     −6.61 (15)     C5---C4---C13---O1      −179.02 (9)
  C1---C2---C3---C4     18.81 (13)     C3---C4---C13---O1      2.51 (15)
  C14---C2---C3---C4    −161.78 (9)    C5---C4---C13---C12     1.68 (15)
  C1---C2---C3---C15    −104.97 (10)   C3---C4---C13---C12     −176.79 (9)
  C14---C2---C3---C15   74.44 (11)     C11---C12---C13---C4    −0.76 (16)
  C2---C3---C4---C13    −16.41 (12)    C11---C12---C13---O1    179.88 (9)
  C15---C3---C4---C13   106.56 (10)    C4---C3---C15---C20     134.98 (10)
  C2---C3---C4---C5     165.16 (8)     C2---C3---C15---C20     −102.93 (10)
  C15---C3---C4---C5    −71.87 (11)    C4---C3---C15---C16     −48.65 (12)
  C13---C4---C5---C6    178.20 (9)     C2---C3---C15---C16     73.44 (11)
  C3---C4---C5---C6     −3.33 (14)     C20---C15---C16---C17   −0.56 (14)
  C13---C4---C5---C10   −1.40 (14)     C3---C15---C16---C17    −177.04 (9)
  C3---C4---C5---C10    177.07 (9)     C15---C16---C17---C18   −0.08 (15)
  C10---C5---C6---C7    0.61 (15)      C16---C17---C18---O2    −179.34 (9)
  C4---C5---C6---C7     −178.99 (10)   C16---C17---C18---C19   0.85 (15)
  C5---C6---C7---C8     −1.03 (16)     O2---C18---C19---C20    179.21 (9)
  C6---C7---C8---C9     0.84 (17)      C17---C18---C19---C20   −0.97 (16)
  C7---C8---C9---C10    −0.24 (17)     C16---C15---C20---C19   0.45 (15)
  C8---C9---C10---C11   179.16 (10)    C3---C15---C20---C19    176.91 (9)
  C8---C9---C10---C5    −0.17 (16)     C18---C19---C20---C15   0.31 (16)
  C6---C5---C10---C11   −179.35 (9)    N1---C1---O1---C13      169.17 (8)
  C4---C5---C10---C11   0.26 (14)      C2---C1---O1---C13      −9.84 (14)
  C6---C5---C10---C9    −0.01 (14)     C4---C13---O1---C1      12.00 (14)
  C4---C5---C10---C9    179.60 (9)     C12---C13---O1---C1     −168.63 (9)
  --------------------- -------------- ----------------------- --------------

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

Cg3 and Cg4 are the centroids of the C5--C10 and C15--C20 rings, respectively. 

  ------------------------- ---------- ---------- ------------- ---------------
  *D*---H···*A*             *D*---H    H···*A*    *D*···*A*     *D*---H···*A*
  N1---H1*N*···O2^i^        0.90 (1)   2.03 (1)   2.9191 (12)   173 (1)
  O2---H2*O*···N2^ii^       0.89 (1)   1.86 (1)   2.7403 (12)   175 (2)
  N1---H2*N*···*Cg*4^iii^   0.88 (1)   2.55 (1)   3.2340 (11)   135 (1)
  C11---H11···*Cg*3^iv^     0.95       2.97       3.7610 (13)   142
  ------------------------- ---------- ---------- ------------- ---------------

Symmetry codes: (i) *x*, *y*, *z*+1; (ii) −*x*+1, *y*−1/2, −*z*+3/2; (iii) −*x*+1, −*y*+1, −*z*+2; (iv) *x*, −*y*−1/2, *z*−1/2. 

###### Hydrogen-bond geometry (, )

*Cg*3 and *Cg*4 are the centroids of the C5C10 and C15C20 rings, respectively. 

  *D*H*A*              *D*H      H*A*      *D* *A*      *D*H*A*
  -------------------- --------- --------- ------------ ---------
  N1H1*N*O2^i^         0.90(1)   2.03(1)   2.9191(12)   173(1)
  O2H2*O*N2^ii^        0.89(1)   1.86(1)   2.7403(12)   175(2)
  N1H2*N* *Cg*4^iii^   0.88(1)   2.55(1)   3.2340(11)   135(1)
  C11H11*Cg*3^iv^      0.95      2.97      3.7610(13)   142

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