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

For the synthesis of pelanserin, see: Cortez *et al.* (1991[@bb1]); Garcia *et al.* (2000[@bb4]); Li *et al.* (2011[@bb5]). For the pharmacology of pelanserin, see: Flores-Murrieta *et al.* (1990[@bb2], 1992[@bb3]); Villalobos-Molina *et al.* (1995[@bb10]). For the structure of quinazoline-2,4(1*H*,3*H*)-dione, see: Liu (2008[@bb6]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~21~H~24~N~4~O~2~*M* *~r~* = 364.44Monoclinic,*a* = 15.7531 (17) Å*b* = 5.4345 (10) Å*c* = 22.756 (3) Åβ = 104.506 (9)°*V* = 1886.0 (5) Å^3^*Z* = 4Mo *K*α radiationμ = 0.09 mm^−1^*T* = 296 K0.60 × 0.30 × 0.10 mm

### Data collection   {#sec2.1.2}

Bruker P4 diffractometer3452 measured reflections3323 independent reflections1301 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.0773 standard reflections every 97 reflections intensity decay: 1%

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.072*wR*(*F* ^2^) = 0.148*S* = 0.993323 reflections247 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.18 e Å^−3^Δρ~min~ = −0.19 e Å^−3^

 {#d5e492}

Data collection: *XSCANS* (Siemens, 1996[@bb9]); cell refinement: *XSCANS*; data reduction: *XSCANS*; program(s) used to solve structure: *SHELXS2013* (Sheldrick, 2008[@bb8]); program(s) used to refine structure: *SHELXL2013* (Sheldrick, 2008[@bb8]); molecular graphics: *Mercury* (Macrae *et al.*, 2008[@bb7]); software used to prepare material for publication: *SHELXL2013*.

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

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S160053681401602X/zs2304sup1.cif](http://dx.doi.org/10.1107/S160053681401602X/zs2304sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S160053681401602X/zs2304Isup2.hkl](http://dx.doi.org/10.1107/S160053681401602X/zs2304Isup2.hkl)

###### 

Click here for additional data file.

Supporting information file. DOI: [10.1107/S160053681401602X/zs2304Isup3.cml](http://dx.doi.org/10.1107/S160053681401602X/zs2304Isup3.cml)

CCDC reference: [1013055](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1013055)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?zs2304&file=zs2304sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?zs2304sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?zs2304&checkcif=yes)

Supporting information for this paper is available from the IUCr electronic archives (Reference: [ZS2304](http://scripts.iucr.org/cgi-bin/sendsup?zs2304)).

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

Quinazolinediones are important heterocycles, which have been shown to possess pharmacologically interesting properties, displaying for example anti-hypertensive, or antidiabetic activity. Among these, synthetic pelanserin (TR-2515) is a well-established potent antihypertensive agent, a feature attributed to its 5-HT~2~ and α~1~-adrenoceptor antagonist activity (Flores-Murrieta *et al.*, 1990, 1992; Villalobos-Molina *et al.*, 1995). Indeed, this molecule presents an activity comparable to that of ketanserin, a clinically used drug. Both molecules also share the quinazoline-2,4-dione scaffold.

We synthesized pelanserin *via* a ring closure procedure we have developed, based on the reaction between an *o*-aminobenzamide and triphosgene (Cortez *et al.*, 1991; Garcia *et al.*, 2000). Such a strategy has also been used starting from isatoic anhydride and a readily available primary amine, with triphosgene as ring closure agent (Li *et al.*, 2011).

The title compound has the expected conformation, with the extended *n*-propyl chain linking the heterocyclic systems (Fig. 1). The quinazolinedione group has the same geometry as that observed for free quinazoline-2,4(1*H*,3*H*)-dione (Liu, 2008), and the piperazine ring is found in the chair conformation, with the phenyl substituent group equatorially located. Both lone pairs in the piperazine ring are thus placed in axial positions. The dihedral angle between phenyl and quinazolinedione rings is 74.1 (1)°, giving a twisted conformation for the overall molecule. The crystal structure is dominated by common intermolecular *R*~2~^2^(8) hydrogen-bonded ring motifs formed through N3---H···O2^i^ hydrogen bonds (Table 2). These centrosymmetric dimers are extended through weak C---H···O hydrogen-bonding associations involving the second carbonyl group in a bifurcated *R*~1~^2^(7) motif (C18---H···O10^ii^, C25---H···O10^ii^), giving an expanded cyclic *R*~2~^2^(20) motif in one-dimensional chains extending along *a* (Fig. 2).

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

2-Amino-*N*-\[3-(4-phenhylpiperazin-1-yl)propyl\]benzamide (1.7 g, 5 mmol) was stirred in CH~2~Cl~2~ (50 ml) at room temperature and triphosgene (0.5 g, 1.7 mmol) in CH~2~Cl~2~ (10 ml) was added. The mixture was refluxed for 2 h. The organic phase was washed with water and dried over MgSO~4~. The solvent was removed under reduced pressure, to give a solid product, which was recrystallized from ethanol, affording pure pelanserin. *M*.p. 190--192 °C, yield 88%; IR (KBr): 3358 (NH), 2982 (CH), 1737 cm^-1^ (C═O). ^1^H-NMR (200 MHz, CDCl~3~, p.p.m.): δ 10.70 (s, 1H), 8.12 (d, 1H, *J* = 8.0 Hz), 7.0 (t, 1H, *J* = 8.4 Hz), 7.25 (m, 4H), 6.87 (m, 3H), 4.19 (t, 2H, *J* = 6.9 Hz), 3.12 (t, 4H, *J* = 6.0 Hz), 2.61 (m, 6H), 1.95 (q, 2H); ^13^C-NMR (50 MHz, CDCl~3~, p.p.m.): δ 162, 152, 151, 139, 135, 129, 128, 123, 119, 116, 114, 56, 53, 49, 30, 25. EIMS (*m*/*z*): 364 \[*M*^+^, 3\], 175 \[100\]. Anal. calcd. for C~21~H~24~N~4~O~2~: C 69.21, H 6.64%; found: C 69.23, H 6.58%.

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

Crystals were thin plates (0.1 mm) and as a consequence, only poorly diffracting samples were obtained, hence room-temperature collected data had resolution limited to sin(θ)/λ = 0.59 Å^-1^, with 97.5% completeness. All H atoms bonded to C atoms were placed in idealized positions and refined as riding on their carrier atoms, with bond lengths fixed to 0.93 Å (aromatic CH) or 0.97 Å (methylene CH~2~). The amine H atom (H3) was found in a difference map and refined freely. For all H atoms, isotropic displacement parameters were calculated as *U*~iso~(H) = 1.2*U*~eq~(carrier atom).

Figures
=======

![Molecular structure of the title compound, with 30% probability level displacement ellipsoids for non-H atoms.](e-70-0o878-fig1){#Fap1}

![Part of the crystal structure, showing hydrogen bonds as dashed lines.](e-70-0o878-fig2){#Fap2}

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

  ------------------------- -------------------------------------
  C~21~H~24~N~4~O~2~        *D*~x~ = 1.283 Mg m^−3^
  *M~r~* = 364.44           Melting point = 463--465 K
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  *a* = 15.7531 (17) Å      Cell parameters from 33 reflections
  *b* = 5.4345 (10) Å       θ = 4.7--10.7°
  *c* = 22.756 (3) Å        µ = 0.09 mm^−1^
  β = 104.506 (9)°          *T* = 296 K
  *V* = 1886.0 (5) Å^3^     Plate, yellow
  *Z* = 4                   0.60 × 0.30 × 0.10 mm
  *F*(000) = 776            
  ------------------------- -------------------------------------

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

  ------------------------------------------ ---------------------------------------------
  Bruker P4 diffractometer                   *R*~int~ = 0.077
  Radiation source: fine-focus sealed tube   θ~max~ = 25.0°, θ~min~ = 2.5°
  Graphite monochromator                     *h* = 0→18
  2θ/ω scans                                 *k* = 0→6
  3452 measured reflections                  *l* = −27→26
  3323 independent reflections               3 standard reflections every 97 reflections
  1301 reflections with *I* \> 2σ(*I*)       intensity decay: 1%
  ------------------------------------------ ---------------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.072   Hydrogen site location: mixed
  *wR*(*F*^2^) = 0.148                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 0.99                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0399*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3323 reflections                      (Δ/σ)~max~ \< 0.001
  247 parameters                        Δρ~max~ = 0.18 e Å^−3^
  0 restraints                          Δρ~min~ = −0.19 e Å^−3^
  0 constraints                         
  ------------------------------------- -------------------------------------------------------------------------------------

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

  ------ -------------- -------------- -------------- -------------------- --
         *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  N1     0.8261 (2)     0.4446 (7)     0.56297 (15)   0.0441 (10)          
  C2     0.8955 (3)     0.4694 (10)    0.5359 (2)     0.0476 (13)          
  O2     0.90428 (19)   0.3299 (6)     0.49494 (13)   0.0615 (10)          
  N3     0.9524 (2)     0.6547 (8)     0.55692 (17)   0.0510 (11)          
  H3     1.004 (3)      0.669 (8)      0.5430 (17)    0.061\*              
  C4     0.9477 (3)     0.8081 (9)     0.60436 (19)   0.0437 (12)          
  C5     1.0100 (3)     0.9929 (9)     0.6239 (2)     0.0530 (14)          
  H5A    1.0556         1.0136         0.6051         0.064\*              
  C6     1.0035 (3)     1.1443 (10)    0.6712 (2)     0.0602 (14)          
  H6A    1.0447         1.2681         0.6842         0.072\*              
  C7     0.9361 (3)     1.1131 (10)    0.6995 (2)     0.0592 (14)          
  H7A    0.9326         1.2143         0.7318         0.071\*              
  C8     0.8741 (3)     0.9326 (9)     0.6800 (2)     0.0536 (14)          
  H8A    0.8282         0.9145         0.6986         0.064\*              
  C9     0.8798 (3)     0.7762 (9)     0.63228 (18)   0.0416 (12)          
  C10    0.8130 (3)     0.5898 (9)     0.61014 (19)   0.0457 (12)          
  O10    0.7479 (2)     0.5615 (6)     0.62947 (13)   0.0649 (10)          
  C11    0.7659 (3)     0.2377 (9)     0.54229 (18)   0.0488 (13)          
  H11A   0.7447         0.1788         0.5763         0.059\*              
  H11B   0.7982         0.1045         0.5296         0.059\*              
  C12    0.6878 (3)     0.3001 (9)     0.49053 (18)   0.0506 (13)          
  H12A   0.7075         0.3740         0.4575         0.061\*              
  H12B   0.6502         0.4169         0.5041         0.061\*              
  C13    0.6375 (3)     0.0642 (9)     0.46908 (18)   0.0502 (13)          
  H13A   0.6737         −0.0416        0.4510         0.060\*              
  H13B   0.6271         −0.0211        0.5041         0.060\*              
  N14    0.5535 (2)     0.1028 (7)     0.42500 (15)   0.0435 (10)          
  C15    0.5664 (3)     0.1797 (9)     0.36668 (18)   0.0551 (14)          
  H15A   0.6014         0.0573         0.3524         0.066\*              
  H15B   0.5985         0.3337         0.3717         0.066\*              
  C16    0.4801 (3)     0.2128 (9)     0.31949 (19)   0.0605 (14)          
  H16A   0.4476         0.3471         0.3317         0.073\*              
  H16B   0.4917         0.2565         0.2809         0.073\*              
  N17    0.4269 (2)     −0.0093 (7)    0.31190 (15)   0.0432 (10)          
  C18    0.4153 (3)     −0.0908 (9)    0.37070 (18)   0.0528 (13)          
  H18A   0.3833         −0.2451        0.3657         0.063\*              
  H18B   0.3811         0.0302         0.3862         0.063\*              
  C19    0.5027 (3)     −0.1247 (9)    0.41534 (19)   0.0555 (14)          
  H19A   0.4935         −0.1805        0.4538         0.067\*              
  H19B   0.5356         −0.2507        0.4004         0.067\*              
  C20    0.3524 (3)     −0.0201 (9)    0.26258 (19)   0.0446 (12)          
  C21    0.3356 (3)     0.1559 (10)    0.2177 (2)     0.0651 (16)          
  H21A   0.3723         0.2919         0.2209         0.078\*              
  C22    0.2645 (3)     0.1331 (11)    0.1677 (2)     0.0708 (17)          
  H22A   0.2545         0.2541         0.1378         0.085\*              
  C23    0.2089 (3)     −0.0630 (11)   0.1614 (2)     0.0643 (15)          
  H23A   0.1614         −0.0777        0.1278         0.077\*              
  C24    0.2254 (3)     −0.2380 (11)   0.2063 (2)     0.0656 (15)          
  H24A   0.1878         −0.3722        0.2031         0.079\*              
  C25    0.2961 (3)     −0.2202 (10)   0.2562 (2)     0.0559 (14)          
  H25A   0.3061         −0.3428        0.2857         0.067\*              
  ------ -------------- -------------- -------------- -------------------- --

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

  ----- ----------- ----------- ------------- ------------ ------------- ------------
        *U*^11^     *U*^22^     *U*^33^       *U*^12^      *U*^13^       *U*^23^
  N1    0.033 (2)   0.057 (3)   0.043 (2)     −0.005 (2)   0.0113 (18)   0.003 (2)
  C2    0.032 (3)   0.069 (4)   0.038 (3)     0.001 (3)    0.000 (2)     0.000 (3)
  O2    0.059 (2)   0.079 (3)   0.0492 (19)   −0.012 (2)   0.0193 (17)   −0.019 (2)
  N3    0.037 (2)   0.065 (3)   0.052 (2)     −0.010 (2)   0.013 (2)     −0.008 (2)
  C4    0.039 (3)   0.049 (3)   0.040 (3)     0.002 (3)    0.005 (2)     0.001 (3)
  C5    0.040 (3)   0.063 (4)   0.053 (3)     0.001 (3)    0.005 (2)     0.012 (3)
  C6    0.057 (3)   0.056 (4)   0.061 (3)     −0.002 (3)   0.002 (3)     −0.002 (3)
  C7    0.065 (3)   0.056 (4)   0.054 (3)     0.006 (3)    0.010 (3)     −0.005 (3)
  C8    0.047 (3)   0.063 (4)   0.050 (3)     0.014 (3)    0.011 (2)     0.007 (3)
  C9    0.039 (3)   0.048 (3)   0.034 (2)     0.012 (3)    0.003 (2)     0.007 (2)
  C10   0.042 (3)   0.051 (3)   0.042 (3)     0.006 (3)    0.007 (2)     0.004 (3)
  O10   0.054 (2)   0.079 (3)   0.073 (2)     −0.009 (2)   0.0345 (18)   −0.008 (2)
  C11   0.036 (3)   0.061 (3)   0.049 (3)     −0.001 (3)   0.010 (2)     0.004 (3)
  C12   0.044 (3)   0.052 (3)   0.048 (3)     −0.005 (3)   −0.002 (2)    0.002 (3)
  C13   0.048 (3)   0.051 (3)   0.048 (3)     −0.001 (3)   0.005 (2)     −0.003 (3)
  N14   0.044 (2)   0.046 (3)   0.039 (2)     −0.006 (2)   0.0074 (18)   −0.005 (2)
  C15   0.051 (3)   0.064 (4)   0.048 (3)     −0.015 (3)   0.008 (2)     0.000 (3)
  C16   0.059 (3)   0.064 (4)   0.055 (3)     −0.016 (3)   0.007 (3)     0.006 (3)
  N17   0.045 (2)   0.048 (3)   0.038 (2)     −0.010 (2)   0.0131 (18)   0.000 (2)
  C18   0.047 (3)   0.062 (4)   0.048 (3)     −0.018 (3)   0.008 (2)     −0.001 (3)
  C19   0.060 (3)   0.060 (4)   0.045 (3)     −0.011 (3)   0.012 (2)     0.000 (3)
  C20   0.044 (3)   0.050 (3)   0.039 (3)     0.002 (3)    0.008 (2)     −0.010 (3)
  C21   0.077 (4)   0.067 (4)   0.044 (3)     −0.011 (3)   0.000 (3)     −0.002 (3)
  C22   0.076 (4)   0.076 (4)   0.051 (3)     0.001 (4)    0.000 (3)     0.008 (3)
  C23   0.049 (3)   0.087 (4)   0.054 (3)     0.000 (4)    0.007 (3)     −0.011 (3)
  C24   0.053 (3)   0.079 (4)   0.064 (3)     −0.022 (3)   0.015 (3)     −0.016 (4)
  C25   0.049 (3)   0.058 (4)   0.056 (3)     −0.005 (3)   0.004 (3)     −0.006 (3)
  ----- ----------- ----------- ------------- ------------ ------------- ------------

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

  ---------------------- ------------ ----------------------- ------------
  N1---C2                1.389 (5)    C13---H13B              0.9700
  N1---C10               1.389 (5)    N14---C15               1.453 (5)
  N1---C11               1.470 (5)    N14---C19               1.459 (5)
  C2---O2                1.235 (5)    C15---C16               1.518 (5)
  C2---N3                1.353 (5)    C15---H15A              0.9700
  N3---C4                1.381 (5)    C15---H15B              0.9700
  N3---H3                0.95 (4)     C16---N17               1.454 (5)
  C4---C9                1.385 (5)    C16---H16A              0.9700
  C4---C5                1.397 (6)    C16---H16B              0.9700
  C5---C6                1.379 (6)    N17---C20               1.407 (5)
  C5---H5A               0.9300       N17---C18               1.464 (5)
  C6---C7                1.384 (6)    C18---C19               1.504 (5)
  C6---H6A               0.9300       C18---H18A              0.9700
  C7---C8                1.377 (6)    C18---H18B              0.9700
  C7---H7A               0.9300       C19---H19A              0.9700
  C8---C9                1.400 (6)    C19---H19B              0.9700
  C8---H8A               0.9300       C20---C21               1.375 (6)
  C9---C10               1.456 (6)    C20---C25               1.388 (6)
  C10---O10              1.223 (5)    C21---C22               1.388 (6)
  C11---C12              1.513 (5)    C21---H21A              0.9300
  C11---H11A             0.9700       C22---C23               1.364 (6)
  C11---H11B             0.9700       C22---H22A              0.9300
  C12---C13              1.522 (6)    C23---C24               1.373 (6)
  C12---H12A             0.9700       C23---H23A              0.9300
  C12---H12B             0.9700       C24---C25               1.381 (5)
  C13---N14              1.462 (5)    C24---H24A              0.9300
  C13---H13A             0.9700       C25---H25A              0.9300
                                                              
  C2---N1---C10          125.0 (4)    C15---N14---C19         107.6 (3)
  C2---N1---C11          116.7 (4)    C15---N14---C13         111.0 (3)
  C10---N1---C11         118.2 (4)    C19---N14---C13         110.5 (4)
  O2---C2---N3           122.3 (4)    N14---C15---C16         112.0 (4)
  O2---C2---N1           121.6 (5)    N14---C15---H15A        109.2
  N3---C2---N1           116.1 (5)    C16---C15---H15A        109.2
  C2---N3---C4           124.4 (4)    N14---C15---H15B        109.2
  C2---N3---H3           119 (3)      C16---C15---H15B        109.2
  C4---N3---H3           115 (3)      H15A---C15---H15B       107.9
  N3---C4---C9           118.8 (5)    N17---C16---C15         111.9 (4)
  N3---C4---C5           120.7 (5)    N17---C16---H16A        109.2
  C9---C4---C5           120.4 (5)    C15---C16---H16A        109.2
  C6---C5---C4           119.6 (5)    N17---C16---H16B        109.2
  C6---C5---H5A          120.2        C15---C16---H16B        109.2
  C4---C5---H5A          120.2        H16A---C16---H16B       107.9
  C5---C6---C7           120.4 (5)    C20---N17---C16         118.0 (4)
  C5---C6---H6A          119.8        C20---N17---C18         116.5 (3)
  C7---C6---H6A          119.8        C16---N17---C18         110.1 (3)
  C8---C7---C6           120.1 (5)    N17---C18---C19         110.6 (3)
  C8---C7---H7A          119.9        N17---C18---H18A        109.5
  C6---C7---H7A          119.9        C19---C18---H18A        109.5
  C7---C8---C9           120.3 (5)    N17---C18---H18B        109.5
  C7---C8---H8A          119.8        C19---C18---H18B        109.5
  C9---C8---H8A          119.8        H18A---C18---H18B       108.1
  C4---C9---C8           119.1 (5)    N14---C19---C18         111.9 (4)
  C4---C9---C10          120.1 (4)    N14---C19---H19A        109.2
  C8---C9---C10          120.6 (5)    C18---C19---H19A        109.2
  O10---C10---N1         120.5 (5)    N14---C19---H19B        109.2
  O10---C10---C9         124.1 (5)    C18---C19---H19B        109.2
  N1---C10---C9          115.4 (4)    H19A---C19---H19B       107.9
  N1---C11---C12         114.3 (4)    C21---C20---C25         117.9 (4)
  N1---C11---H11A        108.7        C21---C20---N17         122.0 (5)
  C12---C11---H11A       108.7        C25---C20---N17         119.9 (4)
  N1---C11---H11B        108.7        C20---C21---C22         120.8 (5)
  C12---C11---H11B       108.7        C20---C21---H21A        119.6
  H11A---C11---H11B      107.6        C22---C21---H21A        119.6
  C11---C12---C13        108.5 (4)    C23---C22---C21         121.4 (5)
  C11---C12---H12A       110.0        C23---C22---H22A        119.3
  C13---C12---H12A       110.0        C21---C22---H22A        119.3
  C11---C12---H12B       110.0        C22---C23---C24         117.8 (5)
  C13---C12---H12B       110.0        C22---C23---H23A        121.1
  H12A---C12---H12B      108.4        C24---C23---H23A        121.1
  N14---C13---C12        114.1 (4)    C23---C24---C25         121.8 (5)
  N14---C13---H13A       108.7        C23---C24---H24A        119.1
  C12---C13---H13A       108.7        C25---C24---H24A        119.1
  N14---C13---H13B       108.7        C24---C25---C20         120.2 (5)
  C12---C13---H13B       108.7        C24---C25---H25A        119.9
  H13A---C13---H13B      107.6        C20---C25---H25A        119.9
                                                              
  C10---N1---C2---O2     178.3 (4)    C10---N1---C11---C12    92.2 (4)
  C11---N1---C2---O2     2.5 (6)      N1---C11---C12---C13    173.4 (4)
  C10---N1---C2---N3     −1.7 (6)     C11---C12---C13---N14   171.7 (3)
  C11---N1---C2---N3     −177.5 (4)   C12---C13---N14---C15   71.1 (5)
  O2---C2---N3---C4      −176.9 (4)   C12---C13---N14---C19   −169.6 (4)
  N1---C2---N3---C4      3.1 (6)      C19---N14---C15---C16   57.1 (5)
  C2---N3---C4---C9      −1.2 (6)     C13---N14---C15---C16   178.1 (4)
  C2---N3---C4---C5      179.0 (4)    N14---C15---C16---N17   −56.3 (5)
  N3---C4---C5---C6      179.7 (4)    C15---C16---N17---C20   −169.2 (4)
  C9---C4---C5---C6      −0.1 (6)     C15---C16---N17---C18   53.8 (5)
  C4---C5---C6---C7      0.4 (7)      C20---N17---C18---C19   167.0 (4)
  C5---C6---C7---C8      −1.0 (7)     C16---N17---C18---C19   −55.2 (5)
  C6---C7---C8---C9      1.3 (7)      C15---N14---C19---C18   −59.3 (5)
  N3---C4---C9---C8      −179.4 (4)   C13---N14---C19---C18   179.4 (3)
  C5---C4---C9---C8      0.5 (6)      N17---C18---C19---N14   59.6 (5)
  N3---C4---C9---C10     −2.3 (6)     C16---N17---C20---C21   8.9 (6)
  C5---C4---C9---C10     177.5 (4)    C18---N17---C20---C21   143.2 (4)
  C7---C8---C9---C4      −1.1 (6)     C16---N17---C20---C25   −175.1 (4)
  C7---C8---C9---C10     −178.1 (4)   C18---N17---C20---C25   −40.7 (6)
  C2---N1---C10---O10    176.8 (4)    C25---C20---C21---C22   −0.1 (7)
  C11---N1---C10---O10   −7.4 (6)     N17---C20---C21---C22   176.1 (4)
  C2---N1---C10---C9     −1.5 (6)     C20---C21---C22---C23   0.3 (8)
  C11---N1---C10---C9    174.3 (3)    C21---C22---C23---C24   0.1 (8)
  C4---C9---C10---O10    −174.7 (4)   C22---C23---C24---C25   −0.7 (8)
  C8---C9---C10---O10    2.3 (7)      C23---C24---C25---C20   0.9 (7)
  C4---C9---C10---N1     3.5 (6)      C21---C20---C25---C24   −0.5 (7)
  C8---C9---C10---N1     −179.5 (4)   N17---C20---C25---C24   −176.7 (4)
  C2---N1---C11---C12    −91.7 (4)                            
  ---------------------- ------------ ----------------------- ------------

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

  ------------------------ ---------- ---------- ----------- ---------------
  *D*---H···*A*            *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N3---H3···O2^i^          0.95 (4)   1.85 (4)   2.799 (5)   171 (4)
  C18---H18*A*···O10^ii^   0.97       2.71       3.625 (6)   157
  C25---H25*A*···O10^ii^   0.93       2.59       3.404 (6)   147
  ------------------------ ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*            *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  ---------------------- ---------- ---------- ----------- -------------
  N3---H3⋯O2^i^          0.95 (4)   1.85 (4)   2.799 (5)   171 (4)
  C18---H18*A*⋯O10^ii^   0.97       2.71       3.625 (6)   157
  C25---H25*A*⋯O10^ii^   0.93       2.59       3.404 (6)   147

Symmetry codes: (i) ; (ii) .

[^1]: Currently unaffiliated to UANL.
