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

For aryl triazenes, their structural properties and metal complexes see: Vrieze & Van Koten (1987[@bb19]); Hörner *et al.* (2002[@bb3], 2004[@bb4], 2006[@bb5]). For the different coordination modes of the triazenide ligand, see: Moore & Robinson (1986[@bb10]). For the synthesis and mol­ecular structure of similar structures with cyano, meth­oxy and eth­oxy groups, see: Melardi *et al.* (2008[@bb7]); Rofouei *et al.* (2006[@bb15]); Rofouei, Melardi, Salemi *et al.* (2009[@bb14]). For the synthesis and crystal structures of Hg^II^ complexes with \[1,3-bis­(2-methoxy­phen­yl)\]triazene by using HgCl~2~, HgBr~2~, Hg(CH~3~COO)~2~ and Hg(SCN)~2~ salts as starting materials, see: Melardi *et al.* (2007[@bb8]); Hematyar & Rofouei (2008[@bb2]); Rofouei, Hematyar *et al.* (2009[@bb12]). For the synthesis and crystal structures of cadmium(II) and silver(I) complexes with 1,3-bis­(2-methoxy­phen­yl)triazene, see: Rofouei, Melardi, Khalili Ghaydari *et al.* (2009[@bb13]) and Payehghadr *et al.* (2007[@bb11]), respectively. For the synthesis and characterization of an isomorphous Hg^II^ structure with \[1,3-bis­(2-ethoxy­phen­yl)\]triazene by using HgCl~2~ instead of HgBr~2~, see: Melardi *et al.* (2009[@bb9]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

\[HgBr(C~16~H~18~N~3~O~2~)\]*M* *~r~* = 564.83Monoclinic,*a* = 10.2359 (7) Å*b* = 7.4659 (5) Å*c* = 22.4123 (14) Åβ = 98.860 (6)°*V* = 1692.32 (19) Å^3^*Z* = 4Mo *K*α radiationμ = 11.47 mm^−1^*T* = 100 K0.28 × 0.12 × 0.03 mm

### Data collection {#sec2.1.2}

Bruker APEXII CCD diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 1998[@bb16]) *T* ~min~ = 0.221, *T* ~max~ = 0.70920759 measured reflections4943 independent reflections4081 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.061

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.029*wR*(*F* ^2^) = 0.062*S* = 1.004943 reflections210 parametersH-atom parameters constrainedΔρ~max~ = 1.33 e Å^−3^Δρ~min~ = −1.43 e Å^−3^

 {#d5e558}

Data collection: *APEX2* (Bruker, 2005[@bb1]); cell refinement: *SAINT* (Bruker, 2005[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb17]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *Mercury* (Macrae *et al.*, 2006[@bb6]), *PLATON* (Spek, 2009[@bb18]) and *SHELXTL* (Sheldrick, 2008[@bb17]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablocks I, global. DOI: [10.1107/S1600536809038732/om2271sup1.cif](http://dx.doi.org/10.1107/S1600536809038732/om2271sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809038732/om2271Isup2.hkl](http://dx.doi.org/10.1107/S1600536809038732/om2271Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?om2271&file=om2271sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?om2271sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?om2271&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [OM2271](http://scripts.iucr.org/cgi-bin/sendsup?om2271)).

Comment
=======

Transition metal complexes containing 1,3-diaryltriazenide ligands have been the object of numerous structural studies in the past few years because of their diverse range of coordination geometries. The uncoordinated --NN--N-- compounds commonly adopt a *trans* configuration in the ground state. As ligands they exhibit versatile coordination geometries: with single or twofold nitrogen chains, neutral or anionic (triazenides) donor sets; they can be monodentate, (N1, N3)-chelating towards one metal atom or (N1, N3)-bridging over two metal atoms (Moore & Robinson, 1986), and they show a remarkable ability to support the stereochemical requisites of a wide variety of transition metal complexes (Hörner *et al.*, 2002, 2004). In these compounds, secondary bonds, or interactions such as hydrogen bonds and metal π-aryl interactions, can play an important role in their structures (Vrieze & Van Koten, 1987; Hörner *et al.*, 2006). We have previously reported the synthesis of the ligands, 1,3-bis(2-methoxyphenyl)\]triazene (Rofouei *et al.*, 2006), \[1,3-bis(2-ethoxyphenyl)\]triazene (Rofouei, Melardi, Salemi *et al.*, 2009), and \[1,3-bis(2-cyanophenyl)\]triazene (Melardi *et al.*, 2008). Representative metal complexes include the Hg^II^ complex with \[1,3-bis(2-methoxyphenyl)\]triazene by using HgCl~2~ (Melardi *et al.*, 2007), HgBr~2~ (Hematyar & Rofouei 2008), Hg(CH~3~COO)~2~ and Hg(SCN)~2~ (Rofouei, Hematyar *et al.*, 2009) salts as starting materials. In addition, Ag(I) and Cd(II) complexes with this ligand are known (Payehghadr *et al.*, 2007; Rofouei, Melardi, Khalili Ghaydari *et al.*, 2009). More recently, a Hg^II^ complex with \[1,3-bis(2-ethoxyphenyl)\]triazene as ligand was reported in which HgCl~2~ was used as the starting salt (Melardi *et al.*, 2009). In this paper, a Hg^II^ complex using HgBr~2~ as a starting material is reported. It is isomorphous to the latter chloride complex.

The molecular structure of HgBr(C~16~H~18~N~3~O~2~) is presented in Fig. 1. The Hg^II^ atom is coordinated by one triazenide and one bromide ion. The 1,3-bis(2-ethoxyphenyl)triazenide is coordinated to the central atom through two N atoms \[Hg1--N1 = 2.086 (3) Å and Hg1--N3 = 2.660 (3) Å\] and one O atom \[Hg1--O1 = 2.722 (3) Å\] at a relatively long distance. The Hg1--Br1 distance of 2.4014 (4) Å is shorter than the corresponding distance in 1,3-bis(2-methoxyphenyl) with Hg1--Br1 = 2.5175 (11) Å (Hematyar & Rofouei, 2008). The Hg--Cl, Hg--O and Hg--N bonds distances in the isomorphous chloride, HgCl(C~16~H~18~N~3~O~2~), are 2.284 (8), 2.721 (2), 2.074 (2) and 2.674 (2) Å, respectively. The atoms of the ligand and the bromide ion generate a plane (maximum deviation from coplanarity of 0.037 Å).

In the title compound, the monomeric HgBr(C~16~H~18~N~3~O~2~) moieties are linked to pairs through non-classical C13--H13B···N2 hydrogen bond (C13···N2 = 3.496 (5) Å and \<C13--H13B···N2 = 151 °, symmetry code (-*x*, 2 - *y*, -*z*). Also, weak Hg-η^3^-arene π-interactions (mean distance of 3.434 (3) Å) are present between these dimers. The secondary Hg-η^3^-arene π-interactions involving three carbon atoms of the C1--C6 phenyl ring. These metal-π interactions involve the Hg1 atom and C4 \[3.461 (5) Å\], C5 \[3.254 (5) Å\] and C6 \[3.515 (5) Å\] atoms with related symmetry code (-*x*, 2 - *y*, -*z*) (Fig. 2). The resulted dimeric units are assembled into zigzag chains by translation along the crystallographic *c* axis through secondary C--H···π stacking interactions. These edge-to-face interactions are present between CH group of phenyl rings and aromatic rings with H···π distances of 2.72 and 2.85 Å for C13--H13A···*Cg*1 \[symmetry code: 1/2 - *x*, -1/2 + *y*, 1/2 - *z*\] and C12--H12···*Cg*1 \[symmetry code: -*x*, 1 - *y*, -*z*\], respectively in which *Cg*1 is the centroid for C7---C12 aromatic ring (Fig. 3). The sum of the weak non-covalent interactions seems to play an important role in the crystal packing. The unit cell packing diagram of the title compound is shown in Fig. 4.

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

A methanol solution of 1,3-bis(2-ethoxyphenyl)triazene (0.2853 g, 1 mmol) was added to a methanol solution of mercury(II) bromide (0.3604 g, 1 mmol). After mixing for 1 h at room temperature, an orange solid was readily precipitated out. It was then filtered off, washed with methanol and dried in vacuum. The orange crude material was dissolved in 10 ml of THF, and placed in a freezer without covering. After two weeks beautiful orange and air-stable crystals of the title complex were obtained by slow evaporation of the solvent.

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

Positions of the H(C) were calculated from geometry with C---H = 0.95 - 0.99 Å. All hydrogen atoms were refined by use of a riding model with *U*~iso~(H) parameters equal to 1.5 *U*~eq~(C) for methyl groups and to 1.2 *U*~eq~(C) for other carbon atoms where *U*~eq~(C) are the equivalent isotropic thermal parameters of the atoms to which the corresponding H atoms are bonded.

Figures
=======

![Molecular structure of the title compound, with ellipsoids drawn at the 50% probability level.](e-65-m1259-fig1){#Fap1}

![Non-classical C13--H13B···N2 hydrogen bond with H13B···N2 distance of 2.60 Å and weak Hg-η3-arene π-interactions (mean distance of 3.434 (3) Å) between dimers. The secondary Hg-η3-arene π-interactions involve three carbon atoms of the C1--C6 phenyl ring.](e-65-m1259-fig2){#Fap2}

![C--H···π stacking interactions between CH group of phenyl rings and aromatic rings with H···π distances of 2.72 and 2.85 Å for C13--H13A···Cg1 and C12--H12···Cg1 (Cg1 is the centroid for the C7---C12 aromatic ring).](e-65-m1259-fig3){#Fap3}

![The packing diagram of the title compound.](e-65-m1259-fig4){#Fap4}

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

  ------------------------------ ---------------------------------------
  \[HgBr(C~16~H~18~N~3~O~2~)\]   *F*(000) = 1064
  *M~r~* = 564.83                *D*~x~ = 2.217 Mg m^−3^
  Monoclinic, *P*2~1~/*n*        Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2yn            Cell parameters from 4844 reflections
  *a* = 10.2359 (7) Å            θ = 2.3--29.5°
  *b* = 7.4659 (5) Å             µ = 11.47 mm^−1^
  *c* = 22.4123 (14) Å           *T* = 100 K
  β = 98.860 (6)°                Plate, orange
  *V* = 1692.32 (19) Å^3^        0.28 × 0.12 × 0.03 mm
  *Z* = 4                        
  ------------------------------ ---------------------------------------

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

  --------------------------------------------------------------- --------------------------------------
  Bruker APEXII CCD diffractometer                                4943 independent reflections
  Radiation source: fine-focus sealed tube                        4081 reflections with *I* \> 2σ(*I*)
  graphite                                                        *R*~int~ = 0.061
  ω scans                                                         θ~max~ = 30.0°, θ~min~ = 2.1°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 1998)   *h* = −14→14
  *T*~min~ = 0.221, *T*~max~ = 0.709                              *k* = −10→10
  20759 measured reflections                                      *l* = −31→31
  --------------------------------------------------------------- --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.029   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.062                  H-atom parameters constrained
  *S* = 1.00                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.01*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4943 reflections                      (Δ/σ)~max~ = 0.001
  210 parameters                        Δρ~max~ = 1.33 e Å^−3^
  0 restraints                          Δρ~min~ = −1.43 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. The maximum and minimum difference map peaks are within 1.21 Å of Hg1.
  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

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

  ------ ---------------- --------------- --------------- -------------------- --
         *x*              *y*             *z*             *U*~iso~\*/*U*~eq~   
  Hg1    −0.152069 (14)   0.681795 (19)   0.053806 (7)    0.01739 (5)          
  Br1    −0.36007 (4)     0.63210 (6)     0.08813 (2)     0.02803 (10)         
  O1     −0.1764 (2)      0.8602 (3)      −0.05325 (12)   0.0160 (5)           
  O2     0.0190 (3)       0.4368 (3)      0.20087 (13)    0.0175 (6)           
  N1     0.0246 (3)       0.7115 (4)      0.01922 (15)    0.0148 (6)           
  N2     0.1262 (3)       0.6390 (4)      0.05569 (15)    0.0140 (6)           
  N3     0.0888 (3)       0.5769 (4)      0.10309 (15)    0.0147 (6)           
  C1     −0.0555 (3)      0.8727 (5)      −0.07197 (17)   0.0127 (7)           
  C2     0.0503 (4)       0.7918 (4)      −0.03385 (17)   0.0133 (7)           
  C3     0.1769 (4)       0.7992 (5)      −0.05036 (18)   0.0170 (8)           
  H3     0.2493           0.7441          −0.0254         0.020\*              
  C4     0.1972 (4)       0.8862 (5)      −0.1028 (2)     0.0202 (8)           
  H4     0.2834           0.8906          −0.1136         0.024\*              
  C5     0.0928 (4)       0.9665 (5)      −0.13943 (18)   0.0182 (8)           
  H5     0.1073           1.0270          −0.1751         0.022\*              
  C6     −0.0331 (4)      0.9589 (5)      −0.12414 (18)   0.0168 (8)           
  H6     −0.1048          1.0134          −0.1497         0.020\*              
  C7     0.1494 (3)       0.4203 (5)      0.19634 (18)    0.0143 (7)           
  C8     0.1896 (3)       0.4974 (5)      0.14479 (17)    0.0136 (7)           
  C9     0.3235 (4)       0.4931 (5)      0.13872 (18)    0.0172 (8)           
  H9     0.3514           0.5475          0.1045          0.021\*              
  C10    0.4158 (4)       0.4114 (5)      0.18149 (19)    0.0187 (8)           
  H10    0.5066           0.4105          0.1770          0.022\*              
  C11    0.3744 (4)       0.3301 (5)      0.23141 (19)    0.0183 (8)           
  H11    0.4371           0.2716          0.2606          0.022\*              
  C12    0.2414 (4)       0.3343 (5)      0.23868 (19)    0.0173 (8)           
  H12    0.2139           0.2781          0.2727          0.021\*              
  C13    −0.2862 (4)      0.9515 (5)      −0.08961 (18)   0.0174 (8)           
  H13A   −0.3002          0.9034          −0.1313         0.021\*              
  H13B   −0.2678          1.0814          −0.0914         0.021\*              
  C14    −0.4070 (4)      0.9196 (6)      −0.0602 (2)     0.0233 (9)           
  H14A   −0.4809          0.9907          −0.0809         0.035\*              
  H14B   −0.3885          0.9552          −0.0177         0.035\*              
  H14C   −0.4303          0.7922          −0.0630         0.035\*              
  C15    −0.0256 (4)      0.3651 (5)      0.25327 (19)    0.0213 (8)           
  H15A   0.0251           0.4179          0.2902          0.026\*              
  H15B   −0.0132          0.2336          0.2548          0.026\*              
  C16    −0.1692 (4)      0.4104 (6)      0.2491 (2)      0.0272 (10)          
  H16A   −0.2048          0.3543          0.2828          0.041\*              
  H16B   −0.2173          0.3659          0.2108          0.041\*              
  H16C   −0.1795          0.5406          0.2511          0.041\*              
  ------ ---------------- --------------- --------------- -------------------- --

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

  ----- -------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^        *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Hg1   0.01495 (7)    0.01991 (8)   0.01826 (8)   −0.00083 (5)   0.00561 (5)    0.00169 (6)
  Br1   0.01972 (19)   0.0300 (2)    0.0374 (3)    0.00079 (16)   0.01402 (18)   0.00757 (19)
  O1    0.0130 (12)    0.0221 (13)   0.0132 (14)   0.0018 (10)    0.0027 (10)    0.0021 (11)
  O2    0.0165 (13)    0.0211 (13)   0.0156 (14)   −0.0003 (10)   0.0042 (11)    0.0040 (11)
  N1    0.0134 (14)    0.0167 (15)   0.0134 (16)   0.0014 (11)    −0.0006 (12)   0.0011 (12)
  N2    0.0169 (15)    0.0129 (14)   0.0117 (16)   −0.0016 (11)   0.0006 (12)    −0.0013 (12)
  N3    0.0156 (15)    0.0143 (14)   0.0138 (16)   −0.0030 (11)   0.0010 (12)    0.0007 (12)
  C1    0.0149 (17)    0.0127 (15)   0.0103 (17)   −0.0005 (13)   0.0017 (14)    −0.0027 (14)
  C2    0.0158 (17)    0.0123 (16)   0.0123 (18)   −0.0007 (12)   0.0043 (14)    −0.0009 (13)
  C3    0.0142 (17)    0.0181 (18)   0.019 (2)     −0.0015 (13)   0.0032 (15)    0.0000 (15)
  C4    0.0159 (18)    0.0242 (19)   0.022 (2)     −0.0039 (15)   0.0085 (16)    −0.0017 (17)
  C5    0.0197 (19)    0.0212 (19)   0.0149 (19)   −0.0034 (15)   0.0061 (15)    0.0005 (16)
  C6    0.0183 (18)    0.0148 (17)   0.017 (2)     −0.0002 (14)   0.0017 (15)    0.0008 (15)
  C7    0.0141 (17)    0.0119 (16)   0.0168 (19)   0.0004 (13)    0.0028 (14)    0.0005 (14)
  C8    0.0170 (17)    0.0123 (16)   0.0110 (18)   0.0001 (13)    0.0007 (14)    −0.0020 (14)
  C9    0.0208 (19)    0.0146 (17)   0.017 (2)     −0.0034 (14)   0.0041 (15)    −0.0011 (15)
  C10   0.0171 (18)    0.0187 (19)   0.019 (2)     −0.0005 (14)   −0.0001 (15)   −0.0015 (16)
  C11   0.0183 (18)    0.0173 (17)   0.017 (2)     0.0004 (14)    −0.0035 (15)   −0.0022 (16)
  C12   0.0215 (18)    0.0131 (17)   0.0167 (19)   −0.0001 (14)   0.0018 (15)    −0.0004 (15)
  C13   0.0146 (17)    0.0189 (18)   0.017 (2)     −0.0005 (14)   −0.0018 (15)   0.0005 (16)
  C14   0.0162 (19)    0.030 (2)     0.023 (2)     0.0012 (16)    0.0029 (16)    −0.0019 (18)
  C15   0.029 (2)      0.0205 (19)   0.015 (2)     0.0008 (16)    0.0069 (17)    0.0025 (16)
  C16   0.029 (2)      0.029 (2)     0.028 (3)     0.0044 (17)    0.0154 (19)    0.0074 (19)
  ----- -------------- ------------- ------------- -------------- -------------- --------------

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

  --------------------- ------------- ---------------------- ------------
  Hg1---N1              2.086 (3)     C7---C8                1.408 (5)
  Hg1---Br1             2.4014 (4)    C8---C9                1.398 (5)
  Hg1---N3              2.660 (3)     C9---C10               1.380 (5)
  O1---C1               1.370 (4)     C9---H9                0.9500
  O1---C13              1.452 (4)     C10---C11              1.395 (6)
  O2---C7               1.359 (4)     C10---H10              0.9500
  O2---C15              1.428 (5)     C11---C12              1.396 (5)
  N1---N2               1.334 (4)     C11---H11              0.9500
  N1---C2               1.393 (5)     C12---H12              0.9500
  N2---N3               1.271 (4)     C13---C14              1.507 (5)
  N3---C8               1.412 (5)     C13---H13A             0.9900
  C1---C6               1.384 (5)     C13---H13B             0.9900
  C1---C2               1.408 (5)     C14---H14A             0.9800
  C2---C3               1.403 (5)     C14---H14B             0.9800
  C3---C4               1.386 (6)     C14---H14C             0.9800
  C3---H3               0.9500        C15---C16              1.497 (6)
  C4---C5               1.381 (6)     C15---H15A             0.9900
  C4---H4               0.9500        C15---H15B             0.9900
  C5---C6               1.385 (5)     C16---H16A             0.9800
  C5---H5               0.9500        C16---H16B             0.9800
  C6---H6               0.9500        C16---H16C             0.9800
  C7---C12              1.387 (5)                            
                                                             
  N1---Hg1---Br1        175.94 (9)    C10---C9---C8          121.3 (4)
  N1---Hg1---N3         52.01 (11)    C10---C9---H9          119.4
  Br1---Hg1---N3        129.22 (7)    C8---C9---H9           119.4
  C1---O1---C13         117.0 (3)     C9---C10---C11         119.3 (4)
  C7---O2---C15         118.0 (3)     C9---C10---H10         120.4
  N2---N1---C2          117.8 (3)     C11---C10---H10        120.4
  N2---N1---Hg1         111.6 (2)     C10---C11---C12        120.4 (4)
  C2---N1---Hg1         130.7 (2)     C10---C11---H11        119.8
  N3---N2---N1          110.7 (3)     C12---C11---H11        119.8
  N2---N3---C8          115.1 (3)     C7---C12---C11         120.1 (4)
  N2---N3---Hg1         85.7 (2)      C7---C12---H12         119.9
  C8---N3---Hg1         159.2 (3)     C11---C12---H12        119.9
  O1---C1---C6          124.4 (3)     O1---C13---C14         107.3 (3)
  O1---C1---C2          115.6 (3)     O1---C13---H13A        110.3
  C6---C1---C2          120.0 (3)     C14---C13---H13A       110.3
  N1---C2---C3          123.1 (3)     O1---C13---H13B        110.3
  N1---C2---C1          118.3 (3)     C14---C13---H13B       110.3
  C3---C2---C1          118.6 (3)     H13A---C13---H13B      108.5
  C4---C3---C2          120.5 (4)     C13---C14---H14A       109.5
  C4---C3---H3          119.7         C13---C14---H14B       109.5
  C2---C3---H3          119.7         H14A---C14---H14B      109.5
  C5---C4---C3          120.3 (4)     C13---C14---H14C       109.5
  C5---C4---H4          119.9         H14A---C14---H14C      109.5
  C3---C4---H4          119.9         H14B---C14---H14C      109.5
  C4---C5---C6          120.0 (4)     O2---C15---C16         107.5 (3)
  C4---C5---H5          120.0         O2---C15---H15A        110.2
  C6---C5---H5          120.0         C16---C15---H15A       110.2
  C1---C6---C5          120.6 (4)     O2---C15---H15B        110.2
  C1---C6---H6          119.7         C16---C15---H15B       110.2
  C5---C6---H6          119.7         H15A---C15---H15B      108.5
  O2---C7---C12         124.2 (4)     C15---C16---H16A       109.5
  O2---C7---C8          116.0 (3)     C15---C16---H16B       109.5
  C12---C7---C8         119.8 (3)     H16A---C16---H16B      109.5
  C9---C8---C7          119.0 (3)     C15---C16---H16C       109.5
  C9---C8---N3          124.9 (3)     H16A---C16---H16C      109.5
  C7---C8---N3          116.0 (3)     H16B---C16---H16C      109.5
                                                             
  N3---Hg1---N1---N2    1.4 (2)       C3---C4---C5---C6      −0.6 (6)
  N3---Hg1---N1---C2    −178.7 (4)    O1---C1---C6---C5      179.5 (3)
  C2---N1---N2---N3     177.6 (3)     C2---C1---C6---C5      0.1 (5)
  Hg1---N1---N2---N3    −2.5 (3)      C4---C5---C6---C1      0.6 (6)
  N1---N2---N3---C8     −179.9 (3)    C15---O2---C7---C12    1.7 (5)
  N1---N2---N3---Hg1    1.8 (3)       C15---O2---C7---C8     −178.3 (3)
  N1---Hg1---N3---N2    −1.37 (19)    O2---C7---C8---C9      176.9 (3)
  Br1---Hg1---N3---N2   173.68 (16)   C12---C7---C8---C9     −3.1 (5)
  N1---Hg1---N3---C8    −177.1 (7)    O2---C7---C8---N3      −2.1 (5)
  Br1---Hg1---N3---C8   −2.1 (7)      C12---C7---C8---N3     177.9 (3)
  C13---O1---C1---C6    −3.0 (5)      N2---N3---C8---C9      3.9 (5)
  C13---O1---C1---C2    176.4 (3)     Hg1---N3---C8---C9     179.2 (5)
  N2---N1---C2---C3     0.1 (5)       N2---N3---C8---C7      −177.2 (3)
  Hg1---N1---C2---C3    −179.7 (3)    Hg1---N3---C8---C7     −1.9 (8)
  N2---N1---C2---C1     −178.4 (3)    C7---C8---C9---C10     1.5 (5)
  Hg1---N1---C2---C1    1.7 (5)       N3---C8---C9---C10     −179.6 (3)
  O1---C1---C2---N1     −1.5 (5)      C8---C9---C10---C11    0.6 (6)
  C6---C1---C2---N1     177.9 (3)     C9---C10---C11---C12   −1.2 (6)
  O1---C1---C2---C3     179.8 (3)     O2---C7---C12---C11    −177.5 (3)
  C6---C1---C2---C3     −0.7 (5)      C8---C7---C12---C11    2.5 (5)
  N1---C2---C3---C4     −177.8 (3)    C10---C11---C12---C7   −0.3 (6)
  C1---C2---C3---C4     0.7 (5)       C1---O1---C13---C14    −179.7 (3)
  C2---C3---C4---C5     −0.1 (6)      C7---O2---C15---C16    176.5 (3)
  --------------------- ------------- ---------------------- ------------

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

  ----------------------- --------- --------- ----------- ---------------
  *D*---H···*A*           *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C13---H13B···N2^i^      0.99      2.60      3.496 (5)   151
  C12---H12···Cg1^ii^     0.95      2.85      3.559 (4)   132
  C13---H13A···Cg1^iii^   0.99      2.72      3.523 (4)   139
  ----------------------- --------- --------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*               *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------------- --------- ------- ----------- -------------
  C13---H13*B*⋯N2^i^        0.99      2.60    3.496 (5)   151
  C12---H12⋯*Cg*1^ii^       0.95      2.85    3.559 (4)   132
  C13---H13*A*⋯*Cg*1^iii^   0.99      2.72    3.523 (4)   139

Symmetry codes: (i) ; (ii) ; (iii) . *Cg*1 is the centroid of the C7--C12 aromatic ring.
