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

For the synthesis and a closely related structure, see: Arumugam *et al.* (2010[@bb2]). For background to microwave chemistry, see: Kappe & Dallinger (2006[@bb6]); Hamzah *et al.* (2011[@bb5]). For the synthesis of benzimidazole derivatives and their applications, see: Wang *et al.* (2011[@bb13]); VanVliet *et al.* (2005[@bb12]); Loupy (2002[@bb7]); Santagada *et al.* (2001[@bb9]); Nicolaou *et al.* (2000[@bb8]); Evans *et al.* (1988[@bb4]). For standard bond lengths, see: Allen *et al.* (1987[@bb1]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~21~H~24~N~2~O~3~*M* *~r~* = 352.42Monoclinic,*a* = 10.6746 (3) Å*b* = 12.3344 (4) Å*c* = 15.6158 (5) Åβ = 106.901 (1)°*V* = 1967.25 (11) Å^3^*Z* = 4Mo *K*α radiationμ = 0.08 mm^−1^*T* = 296 K0.52 × 0.44 × 0.32 mm

### Data collection {#sec2.1.2}

Bruker SMART APEXII CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2009[@bb3]) *T* ~min~ = 0.959, *T* ~max~ = 0.97517688 measured reflections3475 independent reflections2712 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.025

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.045*wR*(*F* ^2^) = 0.122*S* = 1.053475 reflections245 parameters3 restraintsH-atom parameters constrainedΔρ~max~ = 0.35 e Å^−3^Δρ~min~ = −0.18 e Å^−3^

 {#d5e485}

Data collection: *APEX2* (Bruker, 2009[@bb3]); cell refinement: *SAINT* (Bruker, 2009[@bb3]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL* and *PLATON* (Spek, 2009[@bb11]).

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

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536811046095/lh5357sup1.cif](http://dx.doi.org/10.1107/S1600536811046095/lh5357sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536811046095/lh5357Isup2.hkl](http://dx.doi.org/10.1107/S1600536811046095/lh5357Isup2.hkl)

Supplementary material file. DOI: [10.1107/S1600536811046095/lh5357Isup3.cml](http://dx.doi.org/10.1107/S1600536811046095/lh5357Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?lh5357&file=lh5357sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?lh5357sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?lh5357&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [LH5357](http://scripts.iucr.org/cgi-bin/sendsup?lh5357)).

NA, HO and ASAR acknowledge the Ministry of Science, Technology and Innovations of Malaysia for funding the synthetic chemistry work under 304/PFARMASI/650544. NA thanks Universiti Sains Malaysia for the award of a postdoctoral fellowship.

Comment
=======

Microwave-assisted synthesis of heterocycles proves to be an invaluable technology in the fields of medicinal chemistry and drug discovery (Kappe & Dallinger, 2006). The utility of high-speed microwave chemistry is evident from the reported synthesis of privileged structures (Evans *et al.*, 1988; Nicolaou *et al.*, 2000) such as benzodiazepine (Santagada *et al.*, 2001), indoles (Loupy, 2002) and benzimidazoles (Wang *et al.*, 2011; VanVliet *et al.*, 2005). As a part of our on-going work in benzimidazole synthesis under microwave conditions (Hamzah *et al.*, 2011), we present herein the X-ray crystal structure of the title compound.

The molecular structure of the title compound (Fig. 1) is similiar to the previously reported ethyl 1-*sec*-butyl-2-(4-methoxyphenyl) -1*H*-benzimidazole-5-carboxylate (Arumugam *et al.*, 2010) in that only the position of the methoxy group is different. The benzene \[C8---C13\] ring and benzimidazole ring system \[N1/N2/C1-C7\] are essentially planar with maximum deviation of 0.050 (1)Å for atom N2. The mean-planes of the rings form a dihedral angle of 69.94 (7)°. The bond lengths (Allen *et al.*, 1987) and angles aree in the normal ranges and comparable to those in *para*-methoxy derivative. The ethyl atoms (C20 & C21) of ethanoate fragment are disordered over two positions with refined site occupancies of 0.742 (6) and 0.258 (6). In the crystal, a C12---H12···N1^i^ hydrogen bond connects molecules to form a *zigzag* chain propagating along the *b* axis (Fig. 2). An weak intermolecular C20A---H20C···*Cg*^ii^ (minor component of disorder) interaction is also observed; *Cg*1 is the centroid of N1/N2/C1/C2/C7.

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

The title compound was prepared according to our previous procedure (Arumugam *et al.*, 2010). A solution of the *sec*-butyl phenylene diamine (1.0 mmol) and sodium bisulfite adduct of 2-methoxybenzaldehyde (3.5 mmol) in DMF was heated under focused microwave conditions at 403K for 2 minutes. The reaction mixture was diluted in EtOAc (20 ml) and washed with H~2~O (20 ml). The organic layer was pooled together, dried over Na~2~SO~4~, and then removed *in vacuo*. Recrystallization with ethyl acetate gave the title compound as colourless crystals.

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

All atoms were position geometrically and refined using a riding model, with C---H = 0.93--0.97 Å and *U*~iso~(H)= 1.2 or 1.5*U*~eq~(C). The atoms C20 and C21 are disordered over two sites with site occupancies of 0.742 (6) and 0.258 (2). A rigid body restraint (DELU in SHELXL (Sheldrick, 2008)) was applied for atoms C17 and C18. A rotating group model was applied to the non-disordered methyl groups.

Figures
=======

![The molecular structure of (I) with displacement ellipsods are drawn at the 40% probability level. Both disordered component are shown, atoms label with suffix A correspond to minor disorder component.](e-67-o3231-fig1){#Fap1}

![The molecular packing of (I) viewed along the a axis.](e-67-o3231-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~21~H~24~N~2~O~3~        *F*(000) = 752
  *M~r~* = 352.42           *D*~x~ = 1.190 Mg m^−3^
  Monoclinic, *P*2~1~/*n*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2yn       Cell parameters from 8039 reflections
  *a* = 10.6746 (3) Å       θ = 2.1--25.0°
  *b* = 12.3344 (4) Å       µ = 0.08 mm^−1^
  *c* = 15.6158 (5) Å       *T* = 296 K
  β = 106.901 (1)°          Block, colourless
  *V* = 1967.25 (11) Å^3^   0.52 × 0.44 × 0.32 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART APEXII CCD area-detector diffractometer         3475 independent reflections
  Radiation source: fine-focus sealed tube                     2712 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.025
  Detector resolution: 83.66 pixels mm^-1^                     θ~max~ = 25.0°, θ~min~ = 2.1°
  φ and ω scan                                                 *h* = −11→12
  Absorption correction: multi-scan (*SADABS*; Bruker, 2009)   *k* = −11→14
  *T*~min~ = 0.959, *T*~max~ = 0.975                           *l* = −18→17
  17688 measured reflections                                   
  ------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.045   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.122                  H-atom parameters constrained
  *S* = 1.05                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0526*P*)^2^ + 0.5324*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3475 reflections                      (Δ/σ)~max~ \< 0.001
  245 parameters                        Δρ~max~ = 0.35 e Å^−3^
  3 restraints                          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.
  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~   Occ. (\<1)
  O1     0.22019 (14)   0.60261 (11)   0.83252 (9)    0.0694 (4)           
  O2     0.16647 (18)   1.12078 (12)   1.21044 (10)   0.0894 (5)           
  O3     0.10964 (19)   1.17279 (12)   1.06857 (10)   0.0917 (5)           
  N1     0.29480 (16)   0.88252 (11)   0.90695 (9)    0.0562 (4)           
  N2     0.36352 (14)   0.74369 (11)   1.00207 (8)    0.0475 (3)           
  C1     0.34617 (16)   0.78558 (13)   0.91776 (10)   0.0467 (4)           
  C2     0.32104 (16)   0.82294 (12)   1.04995 (10)   0.0445 (4)           
  C3     0.31600 (18)   0.82949 (14)   1.13790 (11)   0.0551 (5)           
  H3     0.3450         0.7729         1.1781         0.066\*              
  C4     0.26638 (18)   0.92316 (14)   1.16254 (11)   0.0542 (4)           
  H4     0.2638         0.9304         1.2213         0.065\*              
  C5     0.21963 (17)   1.00806 (13)   1.10246 (11)   0.0496 (4)           
  C6     0.22494 (19)   1.00099 (13)   1.01515 (11)   0.0540 (5)           
  H6     0.1942         1.0572         0.9748         0.065\*              
  C7     0.27727 (17)   0.90788 (13)   0.98941 (10)   0.0473 (4)           
  C8     0.38804 (17)   0.72852 (14)   0.84697 (10)   0.0498 (4)           
  C9     0.49117 (19)   0.76994 (16)   0.82051 (12)   0.0606 (5)           
  H9     0.5345         0.8316         0.8484         0.073\*              
  C10    0.5308 (2)     0.72096 (19)   0.75319 (13)   0.0711 (6)           
  H10    0.6003         0.7493         0.7358         0.085\*              
  C11    0.4666 (2)     0.63017 (18)   0.71234 (13)   0.0694 (6)           
  H11    0.4939         0.5966         0.6675         0.083\*              
  C12    0.3627 (2)     0.58773 (16)   0.73630 (11)   0.0608 (5)           
  H12    0.3196         0.5264         0.7076         0.073\*              
  C13    0.32254 (18)   0.63726 (14)   0.80372 (11)   0.0517 (4)           
  C14    0.1359 (2)     0.52171 (19)   0.78162 (15)   0.0819 (6)           
  H14A   0.0981         0.5473         0.7216         0.123\*              
  H14B   0.0675         0.5063         0.8084         0.123\*              
  H14C   0.1852         0.4569         0.7805         0.123\*              
  C15    0.42814 (19)   0.63962 (14)   1.03579 (12)   0.0601 (5)           
  H15    0.4483         0.6042         0.9852         0.072\*              
  C16    0.3357 (2)     0.56259 (16)   1.06687 (15)   0.0782 (6)           
  H16A   0.3108         0.5957         1.1151         0.117\*              
  H16B   0.3800         0.4955         1.0869         0.117\*              
  H16C   0.2589         0.5488         1.0179         0.117\*              
  C17    0.5563 (2)     0.65788 (19)   1.10606 (15)   0.0816 (6)           
  H17A   0.5395         0.6900         1.1583         0.098\*              
  H17B   0.5984         0.5884         1.1238         0.098\*              
  C18    0.6475 (2)     0.7294 (2)     1.07565 (18)   0.1013 (8)           
  H18A   0.6583         0.7017         1.0208         0.152\*              
  H18B   0.7308         0.7312         1.1206         0.152\*              
  H18C   0.6120         0.8014         1.0660         0.152\*              
  C19    0.1636 (2)     1.10442 (15)   1.13428 (13)   0.0599 (5)           
  C20    0.0550 (11)    1.2722 (4)     1.0931 (10)    0.103 (2)            0.742 (6)
  H20A   −0.0207        1.2560         1.1134         0.124\*              0.742 (6)
  H20B   0.1196         1.3091         1.1409         0.124\*              0.742 (6)
  C21    0.0176 (5)     1.3391 (3)     1.0141 (4)     0.1145 (15)          0.742 (6)
  H21A   −0.0225        1.4045         1.0269         0.172\*              0.742 (6)
  H21B   −0.0436        1.3005         0.9667         0.172\*              0.742 (6)
  H21C   0.0938         1.3571         0.9963         0.172\*              0.742 (6)
  C21A   0.0967 (16)    1.3540 (11)    1.0711 (11)    0.1145 (15)          0.258 (6)
  H21D   0.0569         1.4175         1.0873         0.172\*              0.258 (6)
  H21E   0.0936         1.3581         1.0091         0.172\*              0.258 (6)
  H21F   0.1863         1.3495         1.1073         0.172\*              0.258 (6)
  C20A   0.027 (4)      1.2591 (10)    1.086 (3)      0.103 (2)            0.258 (6)
  H20C   −0.0605        1.2561         1.0439         0.124\*              0.258 (6)
  H20D   0.0210         1.2562         1.1463         0.124\*              0.258 (6)
  ------ -------------- -------------- -------------- -------------------- ------------

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

  ------ ------------- ------------- ------------- -------------- ------------- --------------
         *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^       *U*^23^
  O1     0.0819 (9)    0.0691 (9)    0.0610 (8)    −0.0156 (7)    0.0268 (7)    −0.0184 (6)
  O2     0.1453 (15)   0.0707 (10)   0.0661 (9)    0.0110 (9)     0.0526 (10)   −0.0165 (7)
  O3     0.1471 (15)   0.0615 (9)    0.0743 (10)   0.0397 (9)     0.0445 (10)   −0.0029 (8)
  N1     0.0877 (11)   0.0440 (8)    0.0398 (8)    0.0137 (7)     0.0233 (7)    0.0026 (6)
  N2     0.0624 (9)    0.0405 (7)    0.0401 (7)    0.0093 (6)     0.0158 (6)    0.0030 (6)
  C1     0.0582 (10)   0.0426 (9)    0.0392 (9)    0.0031 (8)     0.0140 (7)    −0.0008 (7)
  C2     0.0558 (10)   0.0399 (9)    0.0390 (9)    0.0005 (7)     0.0158 (7)    0.0000 (7)
  C3     0.0745 (12)   0.0514 (10)   0.0420 (9)    0.0053 (9)     0.0212 (8)    0.0077 (8)
  C4     0.0724 (12)   0.0558 (11)   0.0394 (9)    −0.0028 (9)    0.0243 (8)    −0.0021 (8)
  C5     0.0639 (11)   0.0422 (9)    0.0473 (10)   −0.0050 (8)    0.0233 (8)    −0.0073 (7)
  C6     0.0795 (12)   0.0391 (9)    0.0451 (10)   0.0076 (8)     0.0207 (9)    0.0020 (7)
  C7     0.0662 (11)   0.0398 (9)    0.0377 (9)    0.0034 (8)     0.0179 (8)    −0.0004 (7)
  C8     0.0630 (11)   0.0465 (10)   0.0396 (9)    0.0106 (8)     0.0146 (8)    −0.0004 (7)
  C9     0.0673 (12)   0.0607 (12)   0.0557 (11)   0.0019 (9)     0.0206 (9)    −0.0064 (9)
  C10    0.0667 (12)   0.0876 (15)   0.0654 (12)   0.0048 (11)    0.0291 (10)   −0.0104 (11)
  C11    0.0724 (13)   0.0841 (15)   0.0542 (11)   0.0195 (11)    0.0224 (10)   −0.0142 (10)
  C12    0.0739 (13)   0.0579 (11)   0.0455 (10)   0.0130 (10)    0.0093 (9)    −0.0108 (8)
  C13    0.0608 (11)   0.0507 (10)   0.0417 (9)    0.0078 (8)     0.0118 (8)    −0.0020 (8)
  C14    0.0747 (14)   0.0818 (15)   0.0828 (15)   −0.0122 (12)   0.0129 (11)   −0.0203 (12)
  C15    0.0793 (13)   0.0460 (10)   0.0529 (11)   0.0168 (9)     0.0158 (9)    0.0044 (8)
  C16    0.1111 (18)   0.0497 (11)   0.0806 (14)   0.0041 (11)    0.0386 (13)   0.0131 (10)
  C17    0.0878 (15)   0.0715 (14)   0.0733 (14)   0.0173 (11)    0.0039 (11)   0.0000 (11)
  C18    0.0757 (16)   0.101 (2)     0.111 (2)     −0.0132 (13)   0.0018 (13)   −0.0121 (15)
  C19    0.0810 (13)   0.0475 (10)   0.0584 (12)   −0.0050 (9)    0.0315 (10)   −0.0091 (9)
  C20    0.153 (6)     0.058 (2)     0.108 (4)     0.034 (3)      0.053 (5)     −0.011 (2)
  C21    0.117 (4)     0.081 (2)     0.142 (4)     0.041 (3)      0.031 (3)     0.006 (3)
  C21A   0.117 (4)     0.081 (2)     0.142 (4)     0.041 (3)      0.031 (3)     0.006 (3)
  C20A   0.153 (6)     0.058 (2)     0.108 (4)     0.034 (3)      0.053 (5)     −0.011 (2)
  ------ ------------- ------------- ------------- -------------- ------------- --------------

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

  --------------------- -------------- ------------------------ --------------
  O1---C13              1.365 (2)      C12---C13                1.388 (2)
  O1---C14              1.422 (2)      C12---H12                0.9300
  O2---C19              1.198 (2)      C14---H14A               0.9600
  O3---C19              1.324 (2)      C14---H14B               0.9600
  O3---C20A             1.456 (5)      C14---H14C               0.9600
  O3---C20              1.456 (4)      C15---C17                1.501 (3)
  N1---C1               1.306 (2)      C15---C16                1.546 (3)
  N1---C7               1.390 (2)      C15---H15                0.9800
  N2---C1               1.376 (2)      C16---H16A               0.9600
  N2---C2               1.385 (2)      C16---H16B               0.9600
  N2---C15              1.480 (2)      C16---H16C               0.9600
  C1---C8               1.485 (2)      C17---C18                1.489 (3)
  C2---C3               1.392 (2)      C17---H17A               0.9700
  C2---C7               1.397 (2)      C17---H17B               0.9700
  C3---C4               1.372 (2)      C18---H18A               0.9600
  C3---H3               0.9300         C18---H18B               0.9600
  C4---C5               1.398 (2)      C18---H18C               0.9600
  C4---H4               0.9300         C20---C21                1.441 (12)
  C5---C6               1.384 (2)      C20---H20A               0.9700
  C5---C19              1.480 (2)      C20---H20B               0.9700
  C6---C7               1.387 (2)      C21---H21A               0.9600
  C6---H6               0.9300         C21---H21B               0.9600
  C8---C9               1.381 (3)      C21---H21C               0.9600
  C8---C13              1.392 (2)      C21A---C20A              1.440 (13)
  C9---C10              1.381 (3)      C21A---H21D              0.9600
  C9---H9               0.9300         C21A---H21E              0.9600
  C10---C11             1.370 (3)      C21A---H21F              0.9600
  C10---H10             0.9300         C20A---H20C              0.9700
  C11---C12             1.373 (3)      C20A---H20D              0.9700
  C11---H11             0.9300                                  
                                                                
  C13---O1---C14        118.20 (15)    N2---C15---C17           111.19 (16)
  C19---O3---C20A       118.4 (17)     N2---C15---C16           111.76 (15)
  C19---O3---C20        116.7 (6)      C17---C15---C16          113.08 (17)
  C1---N1---C7          104.53 (13)    N2---C15---H15           106.8
  C1---N2---C2          106.11 (12)    C17---C15---H15          106.8
  C1---N2---C15         125.83 (13)    C16---C15---H15          106.8
  C2---N2---C15         127.75 (13)    C15---C16---H16A         109.5
  N1---C1---N2          113.72 (13)    C15---C16---H16B         109.5
  N1---C1---C8          122.94 (14)    H16A---C16---H16B        109.5
  N2---C1---C8          123.27 (14)    C15---C16---H16C         109.5
  N2---C2---C3          133.33 (15)    H16A---C16---H16C        109.5
  N2---C2---C7          105.16 (13)    H16B---C16---H16C        109.5
  C3---C2---C7          121.52 (15)    C18---C17---C15          113.38 (19)
  C4---C3---C2          117.02 (15)    C18---C17---H17A         108.9
  C4---C3---H3          121.5          C15---C17---H17A         108.9
  C2---C3---H3          121.5          C18---C17---H17B         108.9
  C3---C4---C5          122.30 (15)    C15---C17---H17B         108.9
  C3---C4---H4          118.8          H17A---C17---H17B        107.7
  C5---C4---H4          118.8          C17---C18---H18A         109.5
  C6---C5---C4          120.35 (15)    C17---C18---H18B         109.5
  C6---C5---C19         121.18 (16)    H18A---C18---H18B        109.5
  C4---C5---C19         118.47 (15)    C17---C18---H18C         109.5
  C5---C6---C7          118.24 (15)    H18A---C18---H18C        109.5
  C5---C6---H6          120.9          H18B---C18---H18C        109.5
  C7---C6---H6          120.9          O2---C19---O3            122.81 (18)
  C6---C7---N1          128.98 (15)    O2---C19---C5            124.93 (19)
  C6---C7---C2          120.55 (14)    O3---C19---C5            112.26 (15)
  N1---C7---C2          110.46 (14)    C21---C20---O3           106.8 (8)
  C9---C8---C13         119.04 (15)    C21---C20---H20A         110.4
  C9---C8---C1          119.08 (16)    O3---C20---H20A          110.4
  C13---C8---C1         121.81 (16)    C21---C20---H20B         110.4
  C10---C9---C8         120.85 (19)    O3---C20---H20B          110.4
  C10---C9---H9         119.6          H20A---C20---H20B        108.6
  C8---C9---H9          119.6          C20---C21---H21A         109.5
  C11---C10---C9        119.33 (19)    C20---C21---H21B         109.5
  C11---C10---H10       120.3          H21A---C21---H21B        109.5
  C9---C10---H10        120.3          C20---C21---H21C         109.5
  C10---C11---C12       121.27 (17)    H21A---C21---H21C        109.5
  C10---C11---H11       119.4          H21B---C21---H21C        109.5
  C12---C11---H11       119.4          C20A---C21A---H21D       109.5
  C11---C12---C13       119.38 (18)    C20A---C21A---H21E       109.5
  C11---C12---H12       120.3          H21D---C21A---H21E       109.5
  C13---C12---H12       120.3          C20A---C21A---H21F       109.5
  O1---C13---C12        124.40 (17)    H21D---C21A---H21F       109.5
  O1---C13---C8         115.49 (14)    H21E---C21A---H21F       109.5
  C12---C13---C8        120.11 (17)    C21A---C20A---O3         101.4 (11)
  O1---C14---H14A       109.5          C21A---C20A---H20C       111.5
  O1---C14---H14B       109.5          O3---C20A---H20C         111.5
  H14A---C14---H14B     109.5          C21A---C20A---H20D       111.5
  O1---C14---H14C       109.5          O3---C20A---H20D         111.5
  H14A---C14---H14C     109.5          H20C---C20A---H20D       109.3
  H14B---C14---H14C     109.5                                   
                                                                
  C7---N1---C1---N2     0.4 (2)        C1---C8---C9---C10       −178.21 (17)
  C7---N1---C1---C8     −176.62 (16)   C8---C9---C10---C11      0.0 (3)
  C2---N2---C1---N1     −1.2 (2)       C9---C10---C11---C12     0.8 (3)
  C15---N2---C1---N1    −175.22 (16)   C10---C11---C12---C13    −0.5 (3)
  C2---N2---C1---C8     175.86 (16)    C14---O1---C13---C12     −10.5 (3)
  C15---N2---C1---C8    1.8 (3)        C14---O1---C13---C8      169.60 (17)
  C1---N2---C2---C3     −178.75 (18)   C11---C12---C13---O1     179.54 (17)
  C15---N2---C2---C3    −4.9 (3)       C11---C12---C13---C8     −0.6 (3)
  C1---N2---C2---C7     1.37 (18)      C9---C8---C13---O1       −178.76 (16)
  C15---N2---C2---C7    175.26 (16)    C1---C8---C13---O1       −1.7 (2)
  N2---C2---C3---C4     180.00 (18)    C9---C8---C13---C12      1.3 (3)
  C7---C2---C3---C4     −0.1 (3)       C1---C8---C13---C12      178.40 (16)
  C2---C3---C4---C5     1.5 (3)        C1---N2---C15---C17      111.1 (2)
  C3---C4---C5---C6     −1.5 (3)       C2---N2---C15---C17      −61.7 (2)
  C3---C4---C5---C19    177.90 (17)    C1---N2---C15---C16      −121.50 (19)
  C4---C5---C6---C7     0.2 (3)        C2---N2---C15---C16      65.7 (2)
  C19---C5---C6---C7    −179.26 (17)   N2---C15---C17---C18     −55.0 (2)
  C5---C6---C7---N1     −178.97 (17)   C16---C15---C17---C18    178.28 (19)
  C5---C6---C7---C2     1.2 (3)        C20A---O3---C19---O2     −13.3 (18)
  C1---N1---C7---C6     −179.38 (19)   C20---O3---C19---O2      1.3 (5)
  C1---N1---C7---C2     0.5 (2)        C20A---O3---C19---C5     167.2 (17)
  N2---C2---C7---C6     178.70 (16)    C20---O3---C19---C5      −178.2 (5)
  C3---C2---C7---C6     −1.2 (3)       C6---C5---C19---O2       −172.8 (2)
  N2---C2---C7---N1     −1.19 (19)     C4---C5---C19---O2       7.8 (3)
  C3---C2---C7---N1     178.91 (16)    C6---C5---C19---O3       6.7 (3)
  N1---C1---C8---C9     65.8 (2)       C4---C5---C19---O3       −172.74 (17)
  N2---C1---C8---C9     −110.9 (2)     C19---O3---C20---C21     172.8 (5)
  N1---C1---C8---C13    −111.2 (2)     C20A---O3---C20---C21    −86 (10)
  N2---C1---C8---C13    72.0 (2)       C19---O3---C20A---C21A   119 (2)
  C13---C8---C9---C10   −1.1 (3)       C20---O3---C20A---C21A   33 (6)
  --------------------- -------------- ------------------------ --------------

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

  --------------------------------------------------
  *Cg* is the centroid of the N1/N2/C1/C2/C7 ring.
  --------------------------------------------------

  ---------------------- --------- --------- ----------- ---------------
  *D*---H···*A*          *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C12---H12···N1^i^      0.93      2.56      3.471 (2)   165
  C20A---H20C···Cg^ii^   0.97      2.90      3.71 (4)    141
  ---------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

*Cg* is the centroid of the N1/N2/C1/C2/C7 ring.

  *D*---H⋯*A*                *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  -------------------------- --------- ------- ----------- -------------
  C12---H12⋯N1^i^            0.93      2.56    3.471 (2)   165
  C20*A*---H20*C*⋯*Cg*^ii^   0.97      2.90    3.71 (4)    141

Symmetry codes: (i) ; (ii) .
