One-dimensional coordination polymers generated from a new triazole bridging ligand and HgX₂ (X = Cl, Br and I): characterization and luminescent properties

The new 4-amino-1,2,4-triazole asymmetric bridging ligand 4-amino-5-(pyridin-3-yl)-3-[4-(pyridin-4-yl)phen­yl]-4H-1,2,4-triazole (L) has been used to generate three novel isomorphic one-dimensional coordination polymers, viz. catena-poly[[tris­[dichloridomercury(II)]-bis­{[mu]₃-4-amino-5-(pyridin-3-yl)-3-[4-(pyridin-4-yl)phen­yl]-4H-1,2,4-triazole}] aceto­nitrile monosolvate], {[Hg₃Cl₆(C₁₈H₁₄N₆)₂]·CH₃CN}_n, (I), and the bromido, {[Hg₃Br₆(C₁₈H₁₄N₆)₂]·CH₃CN}_n, (II), and iodido, {[Hg₃I₆(C₁₈H₁₄N₆)₂]·CH₃CN}_n, (III), analogs. The asymmetric ligand acts as a tridentate ligand to coordinate the three different Hg^II centers (two of which are symmetry-related). Two ligands and two symmetry-related Hg^II centers form centrosymmetric rectangular units which are linked into one-dimensional chains via the other unique Hg atoms, which sit on mirror planes. The chains are elaborated into a three-dimensional structure via inter­chain hydrogen bonds. The acetonitrile solvent mol­ecules are located in ellipsoidal cavities. The luminescent character of these three coordination complexes was investigated in the solid state.

S1. Comment

Coordination polymers containing metal nodes and organic ligands have attracted tremendous attention over the past 30 years because of their wide application as functional materials (Long & Yaghi, 2009; Spokoyny et al., 2009). The syntheses of coordination polymers by judicious choice of organic spacers and metal centers can be an efficient method for obtaining new types of luminescent materials, especially for d¹⁰ or d¹⁰–d¹⁰ systems of metal centers (Morsali & Masoomi, 2009; Tang et al., 2011). The design and construction of coordination polymers based on rigid and bent organic ligands bridged by 4-amino-4H-1,2,4-triazole have been pursued because of their specific geometry (Liu et al., 2009; Du et al., 2006). In addition, hydrogen bonds play an important role in constructing high-dimensional supramolecular compounds (Mu et al., 2008).

The study of the asymmetric oxadiazole ligand with d¹⁰ metal centers has been previously carried out by our group (Song et al., 2010), but the coordination polymers generated by asymmetric 4-amino-4H-1,2,4-triazole-based organic ligands are extremely rare. As part of our systematic studies into self-assembly based on asymmetric ligands, we have synthesized a novel asymmetric rigid ligand, viz. 4-amino-3-[4-(pyridin-4-yl)phenyl]-5-(pyridin-3-yl)-4H-1,2,4-triazole (L), which has a short (pyridin-3-yl) and a long arm [4-(pyridin-4-yl)phenyl]. Three novel isomorphous coordination complexes, viz. {[Hg₃X₆(L)₂].CH₃CN}_n, with X = Cl, (I), Br, (II), and I, (III), based on L were obtained and their structures explored.

The isomorphous compounds (I), (II) and (III) were crystallized in the orthorhombic space group Pnma, with one and a half Hg^II centers, one L ligand, three halide atoms and half an acetonitrile solvent molecule in the asymmetric unit. Single-crystal structural analysis revealed that complex (I) contains two crystallographically independent Hg^II centers, as shown in Fig. 1(a). The Hg1 center is coordinated by one pyridine N atom in the long arm of the ligand, one N atom of the triazole group and two halide atoms. The Hg2 center is coordinated by two pyridine N atoms in the short arm of the ligand in addition to two halide atoms. The intrachain Hg···Hg distance is 8.729 (1) Å, which is similar to our previous report on diiodido[2,5-bis(3-pyridyl)-1,3,4-oxadiazole]mercury (Dong et al., 2003). As shown in Fig. 1(b), two ligands, two Hg1 centers and four halide atoms form rectangular units. In these structural units, the long arms of two ligands and part of the triazole ring with two Hg1 centers form a rectangular 20-membered macrocycle. The pyridine and benzene rings of the long arms of the ligand are almost coplanar, with a dihedral angle of 4.158 (4)° between the planes. In the `rectangle', there are π–π interactions (π–π = 3.800 Å) between the aromatic groups (Fig. 3), while the two pyridine rings and the two benzene rings in the macrocycle are parallel. As shown in Fig. 2, the nearby Hg2 centers are coordinated to form one-dimensional zigzag chains along the [110] direction through Hg—N bonds involving the terminal pyridin-3-yl N atom of the short arm on the ligands. The Hg2 center is located in a distorted tetrahedral environment consisting of two pyridine N-atom donors and two coordinated halide counter-ions, which is similar to our previously reported complex diiodido[2,5-bis(3-pyridyl)-1,3,4-oxadiazole]mercury (Dong et al., 2003).

As shown in Figs. 4(a) and 4(b), the chains are linked by two types of hydrogen-bonding interactions {N—H···N [N5···N3 = 3.15 (1) Å] and N—H···Cl [N5···Cl3 = 3.51 (1) Å]} into three-dimensional networks. Weaker hydrogen-bonding interactions C—H···Cl [C7···Cl1 3.61 (1) Å] extended along the a axis (Fig. 4c). In the three-dimensional network, there are ellipsoidal grids, within which the the acetonitrile solvent molecules are arranged regularly (Fig. 5).

The luminescent properties of these three new coordination polymers were investigated in the solid state at room temperature. Upon excitation at λ = 395 nm, compounds (I)–(III) showed emission maxima at 469, 474 and 474 nm, respectively. Notably, in the cases of (I), (II) and (III), almost identical emission bands were observed with the different intensities (Fig. 6); thus, the different emission luminescent intensities of (I)–(III) might be attributed to the halide-to-ligand charge transfer (XLCT) (Park et al., 2009).

In summary, the asymmetric rigid ligand L can be used as a tridentate ligand to coordinate transition metal ions. Three novel one-dimensional coordination polymers have been synthesized based on L and HgX₂ (X = Cl, Br and I), and their luminescent properties investigated in the solid state at room temperature.

Related literature

For related literature, see: Dong et al. (2003); Du et al. (2006); Morsali & Masoomi (2009); Mu et al. (2008); Liu et al. (2009); Long & Yaghi (2009); Park, et al. (2009); Song et al. (2010); Spokoyny et al. (2009); Tang et al. (2011).

S2. Experimental

For the preparation of 4-amino-5-(3-bromophenyl)-3-(pyridin-3-yl)-4H-1,2,4-triazole, a mixture of hydrazine hydrate (6.90 g, 110 mmol), 3-bromobenzonitrile (5.00 g, 27.5 mmol) and pyridine-3-carbonitrile (2.86 g, 27.5 mmol) in ethanediol (10 ml) was stirred at 413 K for 12 h. The reaction was monitored by thin layer chromatography (TLC). Sufficient water was added to the mixture to cause precipitation. The precipitate was purified by silica-gel column chromatography using dichloromethane (DCM) and MeOH (30:1 v/v) as eluent to afford 4-amino-5-(3-bromophenyl)-3-(pyridin-3-yl)-4H-1,2,4-triazole as a white crystalline solid (yield 2.40 g, 7.6 mmol, 27.6%). ¹H NMR (300 MHz, DMSO, 298 K, TMS): δ 9.18 (s, 1H, –C₅H₄N), 8.73 (d, 1H, –C₅H₄N), 8.39 (d, 1H, –C₅H₄N), 8.27 (s, 1H), 8.06 (d, 1H,–C₆H₄–), 7.75 (d, 1H, –C₆H₄–), 7.61 (m, 1H, –C₆H₄–), 7.54 (t, 1H, –C₆H₄–), 6.42 (s, 2H, –NH₂); IR (KBr pellet, cm^-1): 3417 (s), 3355 (s), 1623 (m), 1598 (m), 1567 (m), 1515 (w), 1477 (s), 1447 (m), 1399 (vs), 1331 (w), 1192 (w), 1070 (m), 1030 (w), 1015 (m), 997 (w), 976 (w), 892 (m), 815 (m), 794 (m), 766 (m), 690 (w). Analysis calculated for C₁₂H₁₂BrN₅: C 22.45, H 1.54, N 8.96%; found: C 22.48, H 1.51, N 9.01%.

For the preparation of 4-amino-3-[4-(pyridin-4-yl)phenyl]-5-(pyridin-3-yl)-4H-1,2,4-triazole (L), a mixture of 4-amino-5-(3-bromophenyl)-3-(pyridin-3-yl)-4H-1,2,4-triazole (2.0 mmol) and pyridine-4-boronic acid (2.4 mmol), Pd(PPh₃)₄ (0.048 mmol), K₂CO₃ (6 mmol) in an EtOH–H₂O system was stirred at 348–353 K for 48 h. After removal of the solvent under vacuum, the residue was purified by silica-gel column chromatography using DCM–MeOH (10:1 v/v) as eluent to afford L as a white crystalline solid (yield 2.40 g, 7.6 mmol, 90.2%). ¹H NMR (300 MHz, DMSO, 298 K, TMS): δ 9.22 (s, 1H, –C₅H₄N), 8.73 (d, 3H, –C₅H₄N), 8.44 (d, 2H, –C₅H₄N), 8.13 (d, 1H, –C₅H₄N), 8.01 (d, 1H, –C₅H₄N), 7.90 (d, 2H, –C₆H₄–), 7.75 (t, 1H, –C₆H₄–), 7.63 (m, 1H, –C₆H₄–), 6.47 (s, 2H, –NH₂); IR (KBr pellet, cm^-1): 3406 (s), 3355 (s), 1637 (m), 1593 (m), 1509 (w), 1463 (m), 1400 (vs), 1264 (w), 1193 (w), 1070 (m), 1026 (w), 970 (w), 919 (w), 901 (m), 814 (w), 795 (m), 713 (m), 692 (m), 610 (m). Analysis calculated for C₁₈H₁₄N₆: C 68.78, H 4.49, N 24.73%; found: C 68.80, H 4.47, N 24.73%.

For the preparation of (I), a solution of HgCl₂ (10.86 mg, 0.04 mmol) in CH₃CN (7 ml) was layered onto a solution of L (6.28 mg, 0.02 mmol) in CH₂Cl₂ (7 ml). The solution was left for about 5 d at room temperature and colorless crystals of (I) were obtained (yield 80%). IR (KBr pellet, cm^-1): 3417 (s), 3330 (s), 2170 (w), 1607 (s), 1518 (w), 1459 (m), 1400 (vs), 1231 (m), 1192 (m), 1122 (m), 1076 (m), 1015 (m), 987 (m), 794 (s), 686 (m), 641 (m), 574 (m). Analysis calculated for C₃₈H₃₁C_l6Hg₃N₁₃: C 30.75, H 2.11, N 12.27%; found: C 30.78, H 2.06, N 12.28%.

For the preparation of (II), a solution of HgBr₂ (14.42 mg, 0.04 mmol) in CH₃CN (7 ml) was layered onto a solution of L (6.28 mg, 0.02 mmol) in CH₂Cl₂ (7 ml). The solution was left for about 5 d at room temperature and colorless crystals of (II) were obtained (yield 78%). IR (KBr pellet, cm^-1): 3417 (s), 3330 (s), 2170 (w), 1607 (s), 1518 (w), 1459 (m), 1400 (vs), 1231 (m), 1192 (m), 1122 (m), 1076 (m), 1015 (m), 987 (m), 794 (s), 686 (m), 641 (m), 574 (m). Analysis calculated for C₃₈H₃₁Br₆Hg₃N₁₃: C 26.07, H 1.78, N 10.40%; found: C 26.09, H 1.76, N 10.41%.

For the preparation of (III), a solution of HgI₂ (18.18 mg, 0.04 mmol) in CH₃CN (7 ml) was layered onto a solution of L (6.28 mg, 0.02 mmol) in CH₂Cl₂ (7 ml). The solution was left for about 5 d at room temperature and colorless crystals (III) were obtained (yield 80%). IR (KBr pellet, cm^-1): 3417 (s), 3332 (s), 2170 (w), 1607 (s), 1515 (m), 1458 (m), 1400 (vs), 1230 (m), 1191 (m), 1121 (m), 1074 (m), 1013 (m), 986 (m), 796 (s), 687 (m), 640 (m), 573(m). Analysis calculated for C₃₈H₃₁Hg₃I₆N₁₃: C 22.45, H 1.54, N 8.96%; found: C 22.46, H 1.52, N 8.98%.

S3. Refinement

For (I), H atoms were placed in geometrically idealized positions and included as riding atoms, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) (aromatic) and C—H = 0.96 Å and U_iso(H) = 1.2U_eq(C) (acetonitrile). The NH₂ group was assumed to be NH₃ and three H atoms were added in geometrically idealized positions. One H atom without an acceptor was then deleted and refined as riding model, with N—H = 0.89 Å and U_iso(H) = 1.2U_eq(N). Half of one Cl atom (Cl4) is disordered over two orientations in the refined ratio 0.64 (8):0.36 (8), and the anisotropic displacement parameters (ADPs) of atoms Cl4 and Cl4' were restrained to be isotropic within a standard uncertainty of 0.01 Ų. The acetonitrile solvent molecule lies on a mirror position and was refined as partially occupied, using a total of 12 restraints. The highest peak of residual electron density was located at (0.0982, 0.7500, 0.0785), 1.00 Å from atom Hg2.

For (II), H atoms on C and N atoms were treated as for (I). The acetonitrile solvent molecule lies on a mirror position and wasrefined as partially occupied. The highest peak of residual electron density was located at (0.0488, 0.7500, 0.9981), 0.99 Å from atom Hg2.

For (III), H atoms on C and N atoms were treated as for (I). The acetonitrile solvent molecule lies on a mirror position and was refined as partially occupied; the ADPs of atoms C19, C20 and N7 was restrained to be isotropic within a standard uncertainty of 0.01 Ų, using a total of 18 restraints. The highest peak of residual electron density was located at (0.1152, 0.7500, 0.2023), 0.99 Šfrom atom I4.

Computing details

For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. (a) The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. (b) The rectangular 20-membered macrocycle formed by two ligands and two Hg^II centers. [Symmetry codes: (i) x, -y+3/2, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, y+1/2, -z+1.]
	Fig. 2. Extension of the centrosymmetric units along the [110] direction. [Symmetry codes: (i) x, -y+3/2, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, y+1/2, -z+1; (iv) x, -y+1/2, z; (v) -x+1, y-1/2, -z+1; (vi) x, y+1, z; (vii) -x+1, -y+2, -z+1.]
	Fig. 3. , The π–π interactions in the rectanglular units (π–π = 3.800 Å).
	Fig. 4. (a) Hydrogen-bonding interactions extending along the c axis, (b) the three-dimensional networks formed via the two kinds of hydrogen bonds (d1 = 2.390 Å and d2 = 2.704 Å) and (c) the three-dimensional hydrogen-bonded network viewed down the a axis (d1 = 2.752 Å).
	Fig. 5. Ellipsoid grids containing acetonitrile solvent molecules.
	Fig. 6. Solid-state luminescent emission properties of the three novel coordination polymers at room temperature.

(I) catena-poly[[tris[dichloridomercury(II)]-bis{µ₃-4-amino- 5-(pyridin-3-yl)-3-[4-(pyridin-4-yl)phenyl]-4H-1,2,4-triazole}] acetonitrile monosolvate]

Crystal data

[Hg3Cl6(C18H14N6)2]·C2H3N	Dx = 2.187 Mg m^−3
Mr = 1484.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 4616 reflections
a = 12.773 (2) Å	θ = 2.4–24.4°
b = 27.267 (5) Å	µ = 10.60 mm^−1
c = 12.941 (2) Å	T = 298 K
V = 4506.9 (14) Å^3	Plan, colourless
Z = 4	0.32 × 0.18 × 0.05 mm
F(000) = 2768

Data collection

Bruker SMART CCD area-detector diffractometer	4277 independent reflections
Radiation source: fine-focus sealed tube	3278 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
ϕ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→15
Tmin = 0.133, Tmax = 0.619	k = −33→17
22532 measured reflections	l = −15→15

Refinement

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1128P)^2 + 27.9072P] where P = (Fo^2 + 2Fc^2)/3
4277 reflections	(Δ/σ)max = 0.001
287 parameters	Δρmax = 2.67 e Å^−3
12 restraints	Δρmin = −1.89 e Å^−3

Special details

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2512 (11)	0.5128 (6)	0.3878 (12)	0.064 (4)
H1	0.2145	0.5071	0.3269	0.077*
C2	0.3371 (12)	0.5424 (6)	0.3839 (11)	0.062 (4)
H2	0.3551	0.5581	0.3226	0.074*
C3	0.3977 (9)	0.5490 (5)	0.4722 (9)	0.037 (2)
C4	0.3600 (9)	0.5277 (5)	0.5608 (9)	0.044 (3)
H4	0.3942	0.5326	0.6234	0.053*
C5	0.2722 (10)	0.4992 (6)	0.5568 (9)	0.052 (3)
H5	0.2510	0.4842	0.6179	0.062*
C6	0.4950 (9)	0.5790 (4)	0.4695 (8)	0.036 (2)
C7	0.5323 (10)	0.5987 (5)	0.3788 (9)	0.050 (3)
H7	0.4939	0.5944	0.3184	0.060*
C8	0.6262 (12)	0.6251 (6)	0.3744 (9)	0.063 (4)
H8	0.6516	0.6365	0.3115	0.075*
C9	0.6799 (10)	0.6337 (5)	0.4639 (9)	0.048 (3)
H9	0.7410	0.6522	0.4616	0.057*
C10	0.6455 (8)	0.6156 (4)	0.5576 (8)	0.034 (2)
C11	0.5513 (9)	0.5883 (5)	0.5610 (8)	0.040 (3)
H11	0.5265	0.5764	0.6238	0.048*
C12	0.7090 (7)	0.6225 (4)	0.6489 (8)	0.031 (2)
C13	0.7644 (8)	0.6399 (4)	0.8043 (8)	0.035 (2)
C14	0.7714 (8)	0.6557 (4)	0.9109 (7)	0.033 (2)
C15	0.8593 (8)	0.6798 (4)	0.9434 (8)	0.036 (2)
H15	0.9108	0.6865	0.8947	0.043*
C16	0.8017 (11)	0.6836 (6)	1.1088 (10)	0.058 (4)
H16	0.8135	0.6919	1.1776	0.069*
C17	0.7105 (12)	0.6617 (6)	1.0845 (10)	0.063 (4)
H17	0.6595	0.6567	1.1347	0.075*
C18	0.6942 (10)	0.6468 (6)	0.9846 (9)	0.055 (4)
H18	0.6324	0.6310	0.9663	0.066*
C19	0.905 (3)	0.7500	0.638 (3)	0.090 (8)
C20	0.926 (5)	0.7500	0.525 (4)	0.21 (3)
H20A	0.9369	0.7169	0.5013	0.320*	0.50
H20B	0.9882	0.7690	0.5105	0.320*	0.50
H20C	0.8679	0.7641	0.4888	0.320*	0.50
Cl1	0.9409 (2)	0.61459 (14)	0.3833 (2)	0.0510 (8)
Cl2	1.0295 (2)	0.52970 (12)	0.6709 (2)	0.0447 (7)
Cl3	1.1093 (4)	0.7500	0.9121 (4)	0.0573 (12)
Cl4	1.066 (4)	0.7500	1.253 (2)	0.029 (6)	0.36 (8)
Cl4'	1.024 (3)	0.7500	1.2638 (8)	0.039 (4)	0.64 (8)
Hg1	0.92151 (4)	0.56482 (2)	0.53538 (4)	0.0524 (2)
Hg2	1.02020 (6)	0.7500	1.07687 (5)	0.0520 (3)
N1	0.2163 (8)	0.4912 (4)	0.4757 (8)	0.045 (3)
N2	0.8105 (7)	0.6135 (4)	0.6523 (7)	0.037 (2)
N3	0.8451 (6)	0.6237 (4)	0.7500 (7)	0.039 (2)
N4	0.6777 (6)	0.6387 (4)	0.7429 (6)	0.033 (2)
N5	0.5797 (6)	0.6573 (4)	0.7741 (7)	0.045 (3)
H5A	0.5660	0.6847	0.7392	0.067*
H5B	0.5303	0.6352	0.7610	0.067*
N6	0.8757 (8)	0.6942 (4)	1.0405 (7)	0.044 (2)
N7	0.880 (3)	0.7500	0.713 (3)	0.129 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.059 (8)	0.073 (11)	0.059 (8)	−0.028 (8)	−0.016 (7)	−0.002 (8)
C2	0.079 (10)	0.060 (9)	0.047 (7)	−0.031 (8)	−0.016 (7)	0.011 (7)
C3	0.034 (5)	0.033 (6)	0.044 (6)	−0.002 (5)	−0.005 (5)	−0.008 (5)
C4	0.044 (7)	0.053 (8)	0.037 (6)	−0.008 (6)	−0.009 (5)	−0.003 (6)
C5	0.048 (7)	0.068 (10)	0.040 (6)	−0.006 (7)	0.004 (5)	−0.007 (6)
C6	0.038 (6)	0.038 (7)	0.031 (5)	0.001 (5)	−0.006 (4)	−0.003 (5)
C7	0.047 (7)	0.067 (9)	0.037 (6)	−0.013 (6)	−0.013 (5)	0.005 (6)
C8	0.072 (9)	0.088 (12)	0.028 (6)	−0.024 (8)	−0.004 (6)	0.016 (7)
C9	0.039 (6)	0.058 (9)	0.046 (6)	−0.011 (6)	−0.008 (5)	0.000 (6)
C10	0.032 (5)	0.039 (6)	0.030 (5)	0.004 (4)	0.001 (4)	−0.006 (5)
C11	0.037 (6)	0.053 (8)	0.031 (5)	−0.005 (5)	0.002 (5)	−0.008 (5)
C12	0.026 (5)	0.035 (6)	0.033 (5)	−0.005 (4)	0.006 (4)	−0.003 (5)
C13	0.026 (5)	0.037 (7)	0.041 (6)	−0.006 (4)	0.000 (4)	−0.003 (5)
C14	0.025 (5)	0.043 (7)	0.032 (5)	−0.001 (4)	−0.001 (4)	0.003 (5)
C15	0.028 (5)	0.041 (7)	0.039 (6)	−0.002 (5)	0.001 (4)	−0.005 (5)
C16	0.069 (9)	0.072 (10)	0.032 (6)	−0.011 (7)	−0.007 (6)	−0.012 (6)
C17	0.065 (9)	0.082 (11)	0.041 (7)	−0.022 (8)	0.018 (6)	−0.005 (7)
C18	0.041 (7)	0.082 (11)	0.043 (7)	−0.014 (7)	0.004 (5)	0.000 (7)
C19	0.12 (2)	0.069 (19)	0.076 (18)	0.000	0.010 (17)	0.000
C20	0.34 (9)	0.09 (4)	0.20 (6)	0.000	0.04 (6)	0.000
Cl1	0.0514 (16)	0.073 (2)	0.0286 (13)	−0.0121 (15)	0.0170 (12)	−0.0064 (14)
Cl2	0.0352 (14)	0.0536 (18)	0.0452 (15)	0.0143 (12)	−0.0051 (11)	−0.0117 (14)
Cl3	0.063 (3)	0.048 (3)	0.062 (3)	0.000	0.005 (2)	0.000
Cl4	0.036 (11)	0.030 (7)	0.021 (6)	0.000	−0.021 (6)	0.000
Cl4'	0.054 (10)	0.048 (4)	0.016 (3)	0.000	−0.017 (4)	0.000
Hg1	0.0437 (3)	0.0625 (4)	0.0512 (4)	−0.0099 (2)	0.0037 (2)	−0.0105 (2)
Hg2	0.0537 (4)	0.0539 (5)	0.0484 (4)	0.000	−0.0190 (3)	0.000
N1	0.041 (5)	0.045 (6)	0.050 (6)	−0.010 (4)	−0.010 (5)	−0.011 (5)
N2	0.033 (5)	0.042 (6)	0.035 (4)	−0.004 (4)	0.003 (4)	−0.010 (4)
N3	0.025 (4)	0.052 (6)	0.041 (5)	−0.002 (4)	−0.005 (4)	−0.015 (5)
N4	0.016 (4)	0.045 (6)	0.038 (5)	−0.004 (3)	0.000 (3)	−0.006 (4)
N5	0.024 (4)	0.072 (8)	0.038 (5)	0.004 (4)	−0.007 (4)	−0.013 (5)
N6	0.052 (6)	0.046 (6)	0.034 (5)	−0.007 (5)	−0.010 (4)	−0.013 (4)
N7	0.18 (3)	0.10 (2)	0.11 (2)	0.000	−0.02 (2)	0.000

Geometric parameters (Å, º)

C1—N1	1.356 (18)	C14—C18	1.393 (16)
C1—C2	1.363 (19)	C15—N6	1.333 (13)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.392 (17)	C16—N6	1.326 (17)
C2—H2	0.9300	C16—C17	1.35 (2)
C3—C4	1.374 (17)	C16—H16	0.9300
C3—C6	1.487 (16)	C17—C18	1.372 (18)
C4—C5	1.365 (18)	C17—H17	0.9300
C4—H4	0.9300	C18—H18	0.9300
C5—N1	1.288 (15)	C19—N7	1.03 (4)
C5—H5	0.9300	C19—C20	1.49 (6)
C6—C7	1.377 (17)	C20—H20A	0.9600
C6—C11	1.407 (15)	C20—H20B	0.9600
C7—C8	1.398 (18)	C20—H20C	0.9600
C7—H7	0.9300	Cl1—Hg1	2.403 (3)
C8—C9	1.366 (17)	Cl2—Hg1	2.428 (3)
C8—H8	0.9300	Cl3—Hg2	2.418 (5)
C9—C10	1.382 (16)	Cl4—Hg2	2.353 (19)
C9—H9	0.9300	Hg1—N1^i	2.336 (10)
C10—C11	1.416 (16)	Hg1—N2	2.462 (9)
C10—C12	1.445 (14)	Hg2—N6	2.438 (10)
C11—H11	0.9300	Hg2—N6^ii	2.438 (10)
C12—N2	1.319 (13)	N1—Hg1^i	2.336 (10)
C12—N4	1.355 (13)	N2—N3	1.369 (12)
C13—N3	1.323 (14)	N4—N5	1.410 (12)
C13—N4	1.364 (13)	N5—H5A	0.8900
C13—C14	1.447 (14)	N5—H5B	0.8900
C14—C15	1.367 (15)
N1—C1—C2	123.5 (12)	N6—C16—C17	123.8 (11)
N1—C1—H1	118.2	N6—C16—H16	118.1
C2—C1—H1	118.2	C17—C16—H16	118.1
C1—C2—C3	119.7 (13)	C16—C17—C18	118.9 (12)
C1—C2—H2	120.2	C16—C17—H17	120.5
C3—C2—H2	120.2	C18—C17—H17	120.5
C4—C3—C2	115.8 (11)	C17—C18—C14	119.1 (12)
C4—C3—C6	123.0 (10)	C17—C18—H18	120.5
C2—C3—C6	121.2 (11)	C14—C18—H18	120.5
C5—C4—C3	119.9 (11)	N7—C19—C20	172 (5)
C5—C4—H4	120.1	C19—C20—H20A	109.5
C3—C4—H4	120.1	C19—C20—H20B	109.5
N1—C5—C4	125.6 (12)	H20A—C20—H20B	109.5
N1—C5—H5	117.2	C19—C20—H20C	109.5
C4—C5—H5	117.2	H20A—C20—H20C	109.5
C7—C6—C11	118.0 (11)	H20B—C20—H20C	109.5
C7—C6—C3	121.6 (10)	N1^i—Hg1—Cl1	113.4 (3)
C11—C6—C3	120.4 (10)	N1^i—Hg1—Cl2	102.4 (3)
C6—C7—C8	122.2 (11)	Cl1—Hg1—Cl2	139.08 (11)
C6—C7—H7	118.9	N1^i—Hg1—N2	87.5 (3)
C8—C7—H7	118.9	Cl1—Hg1—N2	105.0 (2)
C9—C8—C7	119.0 (11)	Cl2—Hg1—N2	95.5 (2)
C9—C8—H8	120.5	Cl4—Hg2—Cl3	137.4 (12)
C7—C8—H8	120.5	Cl4—Hg2—N6	112.1 (9)
C8—C9—C10	121.6 (12)	Cl3—Hg2—N6	100.7 (2)
C8—C9—H9	119.2	Cl4—Hg2—N6^ii	112.1 (9)
C10—C9—H9	119.2	Cl3—Hg2—N6^ii	100.7 (2)
C9—C10—C11	119.0 (10)	N6—Hg2—N6^ii	77.3 (5)
C9—C10—C12	119.5 (10)	C5—N1—C1	115.4 (11)
C11—C10—C12	121.4 (10)	C5—N1—Hg1^i	125.3 (9)
C6—C11—C10	120.2 (10)	C1—N1—Hg1^i	118.7 (8)
C6—C11—H11	119.9	C12—N2—N3	108.0 (8)
C10—C11—H11	119.9	C12—N2—Hg1	130.2 (7)
N2—C12—N4	108.7 (8)	N3—N2—Hg1	119.5 (6)
N2—C12—C10	123.7 (9)	C13—N3—N2	107.9 (8)
N4—C12—C10	127.6 (9)	C12—N4—C13	106.9 (8)
N3—C13—N4	108.4 (9)	C12—N4—N5	129.6 (8)
N3—C13—C14	123.9 (9)	C13—N4—N5	123.0 (8)
N4—C13—C14	127.8 (9)	N4—N5—H5A	109.4
C15—C14—C18	117.0 (10)	N4—N5—H5B	109.3
C15—C14—C13	119.2 (9)	H5A—N5—H5B	109.5
C18—C14—C13	123.8 (10)	C16—N6—C15	116.9 (10)
N6—C15—C14	124.2 (10)	C16—N6—Hg2	123.1 (8)
N6—C15—H15	117.9	C15—N6—Hg2	119.1 (8)
C14—C15—H15	117.9
N1—C1—C2—C3	4 (3)	C4—C5—N1—Hg1^i	172.2 (11)
C1—C2—C3—C4	−5 (2)	C2—C1—N1—C5	−2 (2)
C1—C2—C3—C6	176.8 (14)	C2—C1—N1—Hg1^i	−173.7 (13)
C2—C3—C4—C5	4 (2)	N4—C12—N2—N3	0.2 (13)
C6—C3—C4—C5	−177.6 (12)	C10—C12—N2—N3	−179.7 (10)
C3—C4—C5—N1	−3 (2)	N4—C12—N2—Hg1	162.7 (7)
C4—C3—C6—C7	178.1 (13)	C10—C12—N2—Hg1	−17.2 (16)
C2—C3—C6—C7	−4 (2)	N1^i—Hg1—N2—C12	−39.2 (10)
C4—C3—C6—C11	−2.5 (19)	Cl1—Hg1—N2—C12	74.4 (10)
C2—C3—C6—C11	175.3 (13)	Cl2—Hg1—N2—C12	−141.4 (10)
C11—C6—C7—C8	4 (2)	N1^i—Hg1—N2—N3	121.6 (8)
C3—C6—C7—C8	−177.1 (14)	Cl1—Hg1—N2—N3	−124.9 (7)
C6—C7—C8—C9	−3 (2)	Cl2—Hg1—N2—N3	19.4 (8)
C7—C8—C9—C10	2 (2)	N4—C13—N3—N2	1.7 (12)
C8—C9—C10—C11	−1 (2)	C14—C13—N3—N2	−178.3 (10)
C8—C9—C10—C12	175.3 (13)	C12—N2—N3—C13	−1.2 (13)
C7—C6—C11—C10	−2.4 (19)	Hg1—N2—N3—C13	−165.9 (7)
C3—C6—C11—C10	178.2 (11)	N2—C12—N4—C13	0.8 (12)
C9—C10—C11—C6	1.3 (18)	C10—C12—N4—C13	−179.3 (11)
C12—C10—C11—C6	−175.2 (11)	N2—C12—N4—N5	173.2 (11)
C9—C10—C12—N2	−47.6 (17)	C10—C12—N4—N5	−7.0 (19)
C11—C10—C12—N2	128.9 (12)	N3—C13—N4—C12	−1.5 (12)
C9—C10—C12—N4	132.6 (13)	C14—C13—N4—C12	178.5 (11)
C11—C10—C12—N4	−51.0 (18)	N3—C13—N4—N5	−174.5 (10)
N3—C13—C14—C15	35.9 (18)	C14—C13—N4—N5	5.5 (18)
N4—C13—C14—C15	−144.1 (12)	C17—C16—N6—C15	−3 (2)
N3—C13—C14—C18	−142.5 (13)	C17—C16—N6—Hg2	165.3 (13)
N4—C13—C14—C18	37 (2)	C14—C15—N6—C16	0.8 (19)
C18—C14—C15—N6	1.3 (19)	C14—C15—N6—Hg2	−168.3 (9)
C13—C14—C15—N6	−177.2 (11)	Cl4—Hg2—N6—C16	29.8 (14)
N6—C16—C17—C18	4 (3)	Cl3—Hg2—N6—C16	−177.8 (11)
C16—C17—C18—C14	−1 (3)	N6^ii—Hg2—N6—C16	−79.1 (11)
C15—C14—C18—C17	−1 (2)	Cl4—Hg2—N6—C15	−161.8 (12)
C13—C14—C18—C17	177.4 (14)	Cl3—Hg2—N6—C15	−9.4 (9)
C4—C5—N1—C1	1 (2)	N6^ii—Hg2—N6—C15	89.3 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1^iii	0.93	2.75	3.613 (12)	154
N5—H5A···Cl3^iv	0.89	2.70	3.512 (12)	152
N5—H5B···N3^iv	0.89	2.39	3.149 (12)	143

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

(II) catena-poly[[tris[dibromidomercury(II)]-bis{µ₃-4-amino- 5-(pyridin-3-yl)-3-[4-(pyridin-4-yl)phenyl]-4H-1,2,4-triazole}] acetonitrile monosolvate]

Crystal data

[Hg3Br6(C18H14N6)2]·C2H3N	Dx = 2.501 Mg m^−3
Mr = 1750.99	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 4737 reflections
a = 12.8037 (16) Å	θ = 2.2–24.2°
b = 27.890 (4) Å	µ = 15.08 mm^−1
c = 13.0245 (17) Å	T = 298 K
V = 4651.0 (10) Å^3	Plan, colourless
Z = 4	0.25 × 0.20 × 0.03 mm
F(000) = 3200

Data collection

Bruker SMART CCD area-detector diffractometer	4422 independent reflections
Radiation source: fine-focus sealed tube	3338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ϕ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→15
Tmin = 0.117, Tmax = 0.661	k = −30→33
23320 measured reflections	l = −15→15

Refinement

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 19.0915P] where P = (Fo^2 + 2Fc^2)/3
4422 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 2.17 e Å^−3
0 restraints	Δρmin = −2.04 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2547 (9)	0.5098 (5)	0.3954 (8)	0.063 (4)
H1	0.2159	0.5054	0.3358	0.076*
C2	0.3395 (9)	0.5395 (4)	0.3905 (8)	0.058 (3)
H2	0.3574	0.5545	0.3291	0.069*
C3	0.3995 (7)	0.5473 (4)	0.4794 (7)	0.038 (2)
C4	0.3639 (8)	0.5246 (4)	0.5667 (7)	0.046 (3)
H4	0.3976	0.5296	0.6291	0.055*
C5	0.2781 (7)	0.4944 (4)	0.5621 (7)	0.046 (3)
H5	0.2579	0.4785	0.6217	0.055*
C6	0.4918 (7)	0.5790 (4)	0.4759 (6)	0.039 (2)
C7	0.5274 (8)	0.5985 (4)	0.3854 (7)	0.050 (3)
H7	0.4907	0.5924	0.3252	0.061*
C8	0.6158 (9)	0.6267 (4)	0.3814 (7)	0.053 (3)
H8	0.6370	0.6401	0.3194	0.063*
C9	0.6721 (7)	0.6348 (4)	0.4684 (7)	0.042 (2)
H9	0.7324	0.6532	0.4654	0.050*
C10	0.6395 (7)	0.6154 (4)	0.5627 (6)	0.034 (2)
C11	0.5495 (7)	0.5878 (4)	0.5656 (7)	0.035 (2)
H11	0.5270	0.5750	0.6276	0.042*
C12	0.7065 (7)	0.6219 (4)	0.6518 (6)	0.034 (2)
C13	0.7665 (7)	0.6386 (4)	0.8048 (6)	0.035 (2)
C14	0.7750 (7)	0.6544 (4)	0.9115 (6)	0.037 (2)
C15	0.8625 (7)	0.6803 (4)	0.9401 (7)	0.039 (2)
H15	0.9106	0.6886	0.8896	0.047*
C16	0.8097 (9)	0.6841 (5)	1.1072 (8)	0.060 (3)
H16	0.8212	0.6944	1.1742	0.072*
C17	0.7212 (9)	0.6592 (6)	1.0851 (8)	0.069 (4)
H17	0.6739	0.6523	1.1372	0.083*
C18	0.7007 (8)	0.6442 (4)	0.9860 (8)	0.050 (3)
H18	0.6396	0.6278	0.9699	0.061*
C19	0.9133 (18)	0.7500	0.638 (2)	0.088 (7)
C20	0.943 (3)	0.7500	0.531 (2)	0.175 (17)
H20A	0.9534	0.7176	0.5080	0.263*	0.50
H20B	1.0071	0.7677	0.5224	0.263*	0.50
H20C	0.8891	0.7647	0.4906	0.263*	0.50
Br1	0.93810 (11)	0.61893 (6)	0.37937 (9)	0.0699 (4)
Br2	1.02939 (9)	0.52835 (5)	0.66479 (9)	0.0633 (4)
Br3	1.11989 (15)	0.7500	0.90326 (14)	0.0651 (5)
Br4	1.0444 (2)	0.7500	1.25598 (15)	0.0980 (8)
Hg1	0.91579 (3)	0.566873 (18)	0.53097 (3)	0.05143 (17)
Hg2	1.02217 (5)	0.7500	1.06911 (4)	0.0520 (2)
N1	0.2243 (6)	0.4871 (3)	0.4787 (6)	0.042 (2)
N2	0.8075 (6)	0.6138 (3)	0.6533 (5)	0.0393 (19)
N3	0.8451 (6)	0.6236 (3)	0.7500 (5)	0.0398 (19)
N4	0.6770 (5)	0.6370 (3)	0.7464 (5)	0.0337 (18)
N5	0.5794 (6)	0.6554 (4)	0.7804 (6)	0.046 (2)
H5A	0.5657	0.6828	0.7455	0.069*
H5B	0.5300	0.6332	0.7673	0.069*
N6	0.8809 (7)	0.6939 (3)	1.0349 (6)	0.043 (2)
N7	0.890 (2)	0.7500	0.7162 (17)	0.120 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.057 (7)	0.098 (11)	0.035 (5)	−0.031 (7)	−0.013 (5)	0.001 (6)
C2	0.075 (8)	0.064 (9)	0.034 (5)	−0.028 (6)	−0.016 (5)	0.001 (5)
C3	0.037 (5)	0.032 (6)	0.045 (6)	0.003 (4)	−0.003 (4)	−0.008 (4)
C4	0.051 (6)	0.060 (8)	0.027 (4)	0.002 (5)	0.000 (4)	−0.005 (5)
C5	0.039 (5)	0.061 (8)	0.037 (5)	−0.009 (5)	0.000 (4)	−0.004 (5)
C6	0.038 (5)	0.050 (7)	0.028 (5)	0.001 (4)	−0.005 (4)	−0.006 (4)
C7	0.050 (6)	0.074 (9)	0.027 (5)	−0.009 (6)	−0.009 (4)	0.001 (5)
C8	0.068 (7)	0.061 (8)	0.029 (5)	−0.013 (6)	−0.008 (5)	0.009 (5)
C9	0.039 (5)	0.049 (7)	0.037 (5)	−0.004 (5)	0.005 (4)	0.002 (4)
C10	0.037 (5)	0.037 (6)	0.029 (4)	0.005 (4)	0.002 (4)	−0.008 (4)
C11	0.033 (5)	0.040 (6)	0.032 (5)	−0.004 (4)	0.002 (4)	−0.005 (4)
C12	0.036 (5)	0.040 (6)	0.025 (4)	−0.002 (4)	−0.001 (4)	−0.007 (4)
C13	0.031 (4)	0.044 (6)	0.031 (4)	−0.007 (4)	0.000 (4)	−0.004 (4)
C14	0.038 (5)	0.047 (7)	0.027 (4)	0.000 (4)	0.001 (4)	−0.001 (4)
C15	0.039 (5)	0.038 (6)	0.041 (5)	−0.002 (4)	−0.001 (4)	−0.001 (4)
C16	0.072 (8)	0.080 (9)	0.027 (5)	−0.003 (7)	−0.014 (5)	−0.002 (5)
C17	0.063 (7)	0.113 (12)	0.031 (5)	−0.025 (7)	0.008 (5)	0.002 (6)
C18	0.046 (6)	0.063 (8)	0.043 (6)	−0.016 (5)	0.003 (5)	−0.001 (5)
C19	0.083 (15)	0.073 (17)	0.107 (18)	0.000	−0.012 (14)	0.000
C20	0.29 (5)	0.15 (4)	0.09 (2)	0.000	0.05 (2)	0.000
Br1	0.0775 (8)	0.0880 (11)	0.0441 (6)	−0.0077 (7)	0.0171 (6)	0.0010 (6)
Br2	0.0578 (7)	0.0794 (10)	0.0529 (7)	0.0176 (6)	−0.0055 (5)	−0.0120 (6)
Br3	0.0744 (11)	0.0568 (12)	0.0640 (10)	0.000	0.0057 (9)	0.000
Br4	0.171 (2)	0.0764 (16)	0.0471 (10)	0.000	−0.0423 (12)	0.000
Hg1	0.0461 (3)	0.0649 (4)	0.0433 (3)	−0.0102 (2)	0.00130 (17)	−0.0057 (2)
Hg2	0.0564 (4)	0.0571 (4)	0.0426 (3)	0.000	−0.0175 (3)	0.000
N1	0.041 (4)	0.037 (5)	0.047 (5)	−0.011 (4)	0.003 (4)	−0.010 (4)
N2	0.037 (4)	0.052 (6)	0.030 (4)	−0.002 (4)	0.003 (3)	−0.006 (3)
N3	0.035 (4)	0.052 (6)	0.033 (4)	−0.002 (4)	−0.004 (3)	−0.007 (4)
N4	0.026 (4)	0.044 (5)	0.031 (4)	−0.001 (3)	−0.003 (3)	−0.006 (3)
N5	0.028 (4)	0.070 (7)	0.041 (4)	0.003 (4)	0.000 (3)	−0.004 (4)
N6	0.047 (5)	0.048 (6)	0.033 (4)	−0.003 (4)	−0.008 (4)	−0.005 (4)
N7	0.14 (2)	0.13 (2)	0.083 (14)	0.000	−0.011 (15)	0.000

Geometric parameters (Å, º)

C1—N1	1.315 (13)	C14—C18	1.389 (13)
C1—C2	1.368 (15)	C15—N6	1.314 (11)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.406 (13)	C16—N6	1.339 (14)
C2—H2	0.9300	C16—C17	1.359 (17)
C3—C4	1.379 (14)	C16—H16	0.9300
C3—C6	1.478 (14)	C17—C18	1.383 (15)
C4—C5	1.386 (14)	C17—H17	0.9300
C4—H4	0.9300	C18—H18	0.9300
C5—N1	1.303 (12)	C19—N7	1.06 (3)
C5—H5	0.9300	C19—C20	1.45 (4)
C6—C7	1.375 (13)	C20—H20A	0.9600
C6—C11	1.403 (12)	C20—H20B	0.9600
C7—C8	1.381 (15)	C20—H20C	0.9600
C7—H7	0.9300	Br1—Hg1	2.4674 (14)
C8—C9	1.361 (13)	Br2—Hg1	2.5115 (13)
C8—H8	0.9300	Br3—Hg2	2.4963 (19)
C9—C10	1.406 (12)	Br4—Hg2	2.4505 (19)
C9—H9	0.9300	Hg1—N1^i	2.345 (8)
C10—C11	1.386 (13)	Hg1—N2	2.484 (8)
C10—C12	1.455 (12)	Hg2—N6	2.432 (8)
C11—H11	0.9300	Hg2—N6^ii	2.432 (8)
C12—N2	1.313 (11)	N1—Hg1^i	2.345 (8)
C12—N4	1.356 (10)	N2—N3	1.376 (10)
C13—N3	1.302 (11)	N4—N5	1.422 (10)
C13—N4	1.375 (11)	N5—H5A	0.9059
C13—C14	1.462 (12)	N5—H5B	0.9007
C14—C15	1.384 (13)
N1—C1—C2	124.4 (10)	N6—C16—C17	121.5 (10)
N1—C1—H1	117.8	N6—C16—H16	119.2
C2—C1—H1	117.8	C17—C16—H16	119.2
C1—C2—C3	119.2 (10)	C16—C17—C18	120.7 (10)
C1—C2—H2	120.4	C16—C17—H17	119.6
C3—C2—H2	120.4	C18—C17—H17	119.6
C4—C3—C2	115.4 (9)	C17—C18—C14	117.4 (10)
C4—C3—C6	124.4 (9)	C17—C18—H18	121.3
C2—C3—C6	120.2 (9)	C14—C18—H18	121.3
C3—C4—C5	120.4 (9)	N7—C19—C20	179 (3)
C3—C4—H4	119.8	C19—C20—H20A	109.5
C5—C4—H4	119.8	C19—C20—H20B	109.5
N1—C5—C4	123.4 (10)	H20A—C20—H20B	109.5
N1—C5—H5	118.3	C19—C20—H20C	109.5
C4—C5—H5	118.3	H20A—C20—H20C	109.5
C7—C6—C11	118.1 (9)	H20B—C20—H20C	109.5
C7—C6—C3	121.8 (8)	N1^i—Hg1—Br1	115.0 (2)
C11—C6—C3	120.0 (8)	N1^i—Hg1—N2	86.9 (3)
C6—C7—C8	121.9 (9)	Br1—Hg1—N2	105.5 (2)
C6—C7—H7	119.0	N1^i—Hg1—Br2	101.9 (2)
C8—C7—H7	119.0	Br1—Hg1—Br2	137.73 (5)
C9—C8—C7	119.8 (9)	N2—Hg1—Br2	95.95 (18)
C9—C8—H8	120.1	N6—Hg2—N6^ii	80.0 (4)
C7—C8—H8	120.1	N6—Hg2—Br4	105.57 (18)
C8—C9—C10	120.5 (10)	N6^ii—Hg2—Br4	105.57 (18)
C8—C9—H9	119.8	N6—Hg2—Br3	102.38 (18)
C10—C9—H9	119.8	N6^ii—Hg2—Br3	102.38 (18)
C11—C10—C9	118.9 (8)	Br4—Hg2—Br3	143.24 (9)
C11—C10—C12	122.6 (8)	C5—N1—C1	117.2 (9)
C9—C10—C12	118.3 (9)	C5—N1—Hg1^i	123.3 (7)
C10—C11—C6	120.8 (9)	C1—N1—Hg1^i	119.5 (7)
C10—C11—H11	119.6	C12—N2—N3	108.9 (7)
C6—C11—H11	119.6	C12—N2—Hg1	129.1 (6)
N2—C12—N4	108.3 (7)	N3—N2—Hg1	119.8 (5)
N2—C12—C10	124.8 (8)	C13—N3—N2	107.1 (7)
N4—C12—C10	126.9 (8)	C12—N4—C13	106.3 (7)
N3—C13—N4	109.3 (7)	C12—N4—N5	129.8 (7)
N3—C13—C14	124.0 (8)	C13—N4—N5	123.3 (7)
N4—C13—C14	126.6 (8)	N4—N5—H5A	108.6
C15—C14—C18	118.2 (9)	N4—N5—H5B	108.1
C15—C14—C13	118.3 (8)	H5A—N5—H5B	110.3
C18—C14—C13	123.5 (9)	C15—N6—C16	118.7 (9)
N6—C15—C14	123.3 (9)	C15—N6—Hg2	119.4 (7)
N6—C15—H15	118.3	C16—N6—Hg2	120.6 (7)
C14—C15—H15	118.3
N1—C1—C2—C3	0 (2)	C4—C5—N1—Hg1^i	176.9 (8)
C1—C2—C3—C4	−2.1 (17)	C2—C1—N1—C5	1.4 (19)
C1—C2—C3—C6	179.7 (11)	C2—C1—N1—Hg1^i	−175.4 (11)
C2—C3—C4—C5	3.6 (16)	N4—C12—N2—N3	0.1 (11)
C6—C3—C4—C5	−178.3 (10)	C10—C12—N2—N3	−179.8 (9)
C3—C4—C5—N1	−2.9 (17)	N4—C12—N2—Hg1	162.7 (6)
C4—C3—C6—C7	176.1 (11)	C10—C12—N2—Hg1	−17.2 (15)
C2—C3—C6—C7	−5.9 (16)	N1^i—Hg1—N2—C12	−38.1 (9)
C4—C3—C6—C11	0.0 (16)	Br1—Hg1—N2—C12	77.1 (9)
C2—C3—C6—C11	178.0 (10)	Br2—Hg1—N2—C12	−139.7 (8)
C11—C6—C7—C8	−1.3 (17)	N1^i—Hg1—N2—N3	122.9 (7)
C3—C6—C7—C8	−177.5 (11)	Br1—Hg1—N2—N3	−122.0 (6)
C6—C7—C8—C9	1.9 (19)	Br2—Hg1—N2—N3	21.3 (7)
C7—C8—C9—C10	−1.3 (18)	N4—C13—N3—N2	2.3 (11)
C8—C9—C10—C11	0.2 (16)	C14—C13—N3—N2	−177.6 (9)
C8—C9—C10—C12	175.3 (10)	C12—N2—N3—C13	−1.5 (11)
C9—C10—C11—C6	0.4 (15)	Hg1—N2—N3—C13	−166.0 (6)
C12—C10—C11—C6	−174.5 (9)	N2—C12—N4—C13	1.2 (11)
C7—C6—C11—C10	0.2 (15)	C10—C12—N4—C13	−178.9 (10)
C3—C6—C11—C10	176.4 (9)	N2—C12—N4—N5	171.9 (9)
C11—C10—C12—N2	127.0 (11)	C10—C12—N4—N5	−8.2 (17)
C9—C10—C12—N2	−48.0 (15)	N3—C13—N4—C12	−2.2 (11)
C11—C10—C12—N4	−52.9 (15)	C14—C13—N4—C12	177.7 (10)
C9—C10—C12—N4	132.2 (11)	N3—C13—N4—N5	−173.7 (9)
N3—C13—C14—C15	38.0 (15)	C14—C13—N4—N5	6.2 (15)
N4—C13—C14—C15	−141.9 (10)	C14—C15—N6—C16	−2.9 (16)
N3—C13—C14—C18	−141.0 (11)	C14—C15—N6—Hg2	−170.2 (8)
N4—C13—C14—C18	39.1 (17)	C17—C16—N6—C15	2.0 (18)
C18—C14—C15—N6	3.1 (16)	C17—C16—N6—Hg2	169.1 (11)
C13—C14—C15—N6	−176.0 (10)	N6^ii—Hg2—N6—C15	87.7 (8)
N6—C16—C17—C18	−1 (2)	Br4—Hg2—N6—C15	−168.8 (7)
C16—C17—C18—C14	2 (2)	Br3—Hg2—N6—C15	−12.9 (8)
C15—C14—C18—C17	−2.3 (17)	N6^ii—Hg2—N6—C16	−79.4 (9)
C13—C14—C18—C17	176.7 (11)	Br4—Hg2—N6—C16	24.2 (9)
C4—C5—N1—C1	0.3 (16)	Br3—Hg2—N6—C16	−180.0 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Br1^iii	0.93	2.85	3.678 (9)	150
N5—H5A···Br3^iv	0.91	2.78	3.599 (10)	150
N5—H5B···N3^iv	0.90	2.39	3.153 (10)	142

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

(III) catena-poly[[tris[diiodidomercury(II)]-bis{µ₃-4-amino- 5-(pyridin-3-yl)-3-[4-(pyridin-4-yl)phenyl]-4H-1,2,4-triazole}] acetonitrile monosolvate]

Crystal data

[Hg3I6(C18H14N6)2]·C2H3N	Dx = 2.731 Mg m^−3
Mr = 2032.93	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 7784 reflections
a = 12.822 (3) Å	θ = 2.3–27.5°
b = 28.976 (7) Å	µ = 13.08 mm^−1
c = 13.309 (3) Å	T = 298 K
V = 4945 (2) Å^3	Plan, colourless
Z = 4	0.50 × 0.20 × 0.04 mm
F(000) = 3632

Data collection

Bruker SMART CCD area-detector diffractometer	4701 independent reflections
Radiation source: fine-focus sealed tube	3888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ϕ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→15
Tmin = 0.059, Tmax = 0.623	k = −35→32
24554 measured reflections	l = −15→16

Refinement

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0671P)^2 + 52.8532P] where P = (Fo^2 + 2Fc^2)/3
4701 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 2.60 e Å^−3
18 restraints	Δρmin = −1.85 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2600 (10)	0.5064 (5)	0.4001 (9)	0.057 (4)
H1	0.2219	0.5022	0.3413	0.069*
C2	0.3397 (11)	0.5365 (5)	0.3982 (8)	0.054 (3)
H2	0.3564	0.5518	0.3389	0.065*
C3	0.3971 (8)	0.5448 (4)	0.4850 (7)	0.030 (2)
C4	0.3663 (9)	0.5214 (4)	0.5691 (8)	0.042 (3)
H4	0.3994	0.5271	0.6300	0.051*
C5	0.2876 (9)	0.4899 (4)	0.5644 (8)	0.042 (3)
H5	0.2715	0.4730	0.6218	0.051*
C6	0.4870 (7)	0.5782 (3)	0.4854 (7)	0.027 (2)
C7	0.5198 (8)	0.5989 (4)	0.3964 (7)	0.036 (2)
H7	0.4834	0.5931	0.3373	0.044*
C8	0.6039 (9)	0.6274 (4)	0.3944 (8)	0.045 (3)
H8	0.6225	0.6417	0.3344	0.054*
C9	0.6614 (8)	0.6354 (4)	0.4782 (7)	0.035 (2)
H9	0.7201	0.6542	0.4758	0.042*
C10	0.6301 (8)	0.6146 (3)	0.5691 (7)	0.028 (2)
C11	0.5450 (7)	0.5865 (4)	0.5712 (7)	0.028 (2)
H11	0.5255	0.5727	0.6314	0.034*
C12	0.7022 (8)	0.6202 (3)	0.6574 (7)	0.029 (2)
C13	0.7647 (7)	0.6366 (3)	0.8038 (7)	0.028 (2)
C14	0.7755 (8)	0.6525 (4)	0.9088 (7)	0.033 (2)
C15	0.8606 (8)	0.6801 (4)	0.9316 (7)	0.034 (2)
H15	0.9057	0.6886	0.8801	0.041*
C16	0.8154 (10)	0.6831 (4)	1.0988 (8)	0.046 (3)
H16	0.8285	0.6936	1.1636	0.055*
C17	0.7288 (11)	0.6557 (5)	1.0810 (9)	0.059 (4)
H17	0.6846	0.6474	1.1335	0.071*
C18	0.7089 (9)	0.6407 (5)	0.9837 (8)	0.049 (3)
H18	0.6505	0.6227	0.9700	0.059*
C19	0.922 (2)	0.7500	0.638 (2)	0.097 (8)
C20	0.967 (4)	0.7500	0.536 (3)	0.169 (17)
H20A	0.9771	0.7188	0.5134	0.253*	0.50
H20B	1.0335	0.7656	0.5366	0.253*	0.50
H20C	0.9210	0.7657	0.4905	0.253*	0.50
I1	0.93194 (8)	0.62394 (4)	0.37414 (6)	0.0631 (3)
I2	1.03030 (7)	0.52660 (3)	0.66052 (6)	0.0599 (3)
I3	1.12891 (13)	0.7500	0.88685 (11)	0.0707 (4)
I4	1.05389 (15)	0.7500	1.24935 (10)	0.0764 (5)
Hg1	0.90889 (4)	0.569653 (17)	0.53010 (3)	0.04264 (16)
Hg2	1.02075 (5)	0.7500	1.05464 (4)	0.04159 (19)
N1	0.2324 (7)	0.4823 (3)	0.4806 (6)	0.040 (2)
N2	0.8025 (6)	0.6127 (3)	0.6544 (6)	0.0317 (19)
N3	0.8420 (7)	0.6234 (3)	0.7481 (6)	0.036 (2)
N4	0.6741 (6)	0.6355 (3)	0.7499 (5)	0.0287 (17)
N5	0.5783 (6)	0.6520 (4)	0.7853 (6)	0.040 (2)
H5A	0.5646	0.6794	0.7504	0.060*
H5B	0.5289	0.6298	0.7721	0.060*
N6	0.8802 (7)	0.6948 (3)	1.0249 (6)	0.035 (2)
N7	0.902 (2)	0.7500	0.711 (2)	0.129 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.062 (8)	0.072 (10)	0.037 (6)	−0.038 (7)	−0.015 (6)	0.004 (6)
C2	0.071 (9)	0.058 (8)	0.033 (5)	−0.029 (7)	−0.010 (5)	0.004 (5)
C3	0.030 (5)	0.025 (5)	0.034 (5)	−0.004 (4)	−0.003 (4)	0.002 (4)
C4	0.038 (6)	0.052 (7)	0.037 (5)	−0.009 (5)	−0.005 (5)	0.001 (5)
C5	0.036 (6)	0.052 (7)	0.039 (6)	−0.011 (5)	0.002 (5)	−0.001 (5)
C6	0.027 (5)	0.026 (5)	0.027 (4)	−0.002 (4)	−0.001 (4)	−0.004 (4)
C7	0.040 (6)	0.041 (6)	0.028 (5)	−0.008 (5)	−0.008 (4)	0.002 (4)
C8	0.052 (7)	0.044 (7)	0.038 (6)	−0.003 (6)	0.002 (5)	0.011 (5)
C9	0.034 (6)	0.027 (6)	0.044 (6)	−0.001 (4)	0.000 (4)	0.001 (4)
C10	0.037 (5)	0.015 (5)	0.033 (5)	−0.003 (4)	−0.006 (4)	−0.005 (4)
C11	0.023 (5)	0.035 (6)	0.027 (4)	0.000 (4)	−0.001 (4)	−0.006 (4)
C12	0.033 (5)	0.026 (5)	0.029 (5)	−0.010 (4)	0.000 (4)	−0.002 (4)
C13	0.030 (5)	0.025 (5)	0.030 (5)	−0.006 (4)	−0.002 (4)	−0.005 (4)
C14	0.038 (6)	0.029 (6)	0.032 (5)	−0.002 (4)	−0.002 (4)	0.002 (4)
C15	0.038 (6)	0.036 (6)	0.028 (5)	−0.010 (5)	−0.005 (4)	−0.004 (4)
C16	0.052 (7)	0.055 (8)	0.032 (5)	−0.001 (6)	−0.010 (5)	−0.009 (5)
C17	0.058 (8)	0.085 (11)	0.035 (6)	−0.014 (7)	0.009 (6)	−0.003 (6)
C18	0.034 (6)	0.066 (9)	0.048 (6)	−0.019 (6)	0.005 (5)	−0.011 (6)
C19	0.095 (11)	0.096 (12)	0.099 (11)	0.000	0.006 (9)	0.000
C20	0.177 (19)	0.168 (19)	0.162 (19)	0.000	0.004 (10)	0.000
I1	0.0694 (6)	0.0741 (7)	0.0458 (5)	−0.0059 (5)	0.0160 (4)	0.0063 (4)
I2	0.0613 (6)	0.0665 (6)	0.0520 (5)	0.0142 (4)	−0.0041 (4)	−0.0122 (4)
I3	0.0941 (11)	0.0454 (8)	0.0725 (8)	0.000	0.0119 (8)	0.000
I4	0.1369 (14)	0.0489 (8)	0.0433 (6)	0.000	−0.0357 (7)	0.000
Hg1	0.0415 (3)	0.0468 (3)	0.0396 (2)	−0.0112 (2)	−0.00049 (18)	−0.00256 (19)
Hg2	0.0483 (4)	0.0382 (4)	0.0383 (3)	0.000	−0.0146 (3)	0.000
N1	0.041 (5)	0.040 (5)	0.039 (5)	−0.005 (4)	−0.001 (4)	−0.014 (4)
N2	0.022 (4)	0.038 (5)	0.035 (4)	−0.002 (4)	−0.005 (3)	−0.010 (4)
N3	0.030 (5)	0.047 (6)	0.031 (4)	−0.002 (4)	0.001 (4)	−0.009 (4)
N4	0.024 (4)	0.035 (5)	0.028 (4)	−0.004 (3)	0.003 (3)	−0.003 (3)
N5	0.019 (4)	0.063 (7)	0.038 (4)	−0.002 (4)	−0.001 (3)	−0.008 (4)
N6	0.044 (5)	0.028 (5)	0.034 (4)	−0.006 (4)	−0.012 (4)	−0.004 (4)
N7	0.129 (13)	0.133 (13)	0.127 (12)	0.000	−0.005 (9)	0.000

Geometric parameters (Å, º)

C1—N1	1.327 (15)	C14—C15	1.386 (14)
C1—C2	1.344 (16)	C15—N6	1.337 (12)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.390 (14)	C16—N6	1.331 (15)
C2—H2	0.9300	C16—C17	1.386 (18)
C3—C4	1.366 (15)	C16—H16	0.9300
C3—C6	1.506 (13)	C17—C18	1.391 (16)
C4—C5	1.363 (15)	C17—H17	0.9300
C4—H4	0.9300	C18—H18	0.9300
C5—N1	1.340 (14)	C19—N7	1.00 (4)
C5—H5	0.9300	C19—C20	1.47 (4)
C6—C11	1.385 (13)	C20—H20A	0.9600
C6—C7	1.392 (14)	C20—H20B	0.9600
C7—C8	1.358 (16)	C20—H20C	0.9600
C7—H7	0.9300	I1—Hg1	2.6211 (11)
C8—C9	1.357 (15)	I2—Hg1	2.6444 (11)
C8—H8	0.9300	I3—Hg2	2.6287 (17)
C9—C10	1.410 (14)	I4—Hg2	2.6258 (14)
C9—H9	0.9300	Hg1—N1^i	2.359 (9)
C10—C11	1.361 (14)	Hg1—N2	2.481 (8)
C10—C12	1.504 (13)	Hg2—N6	2.442 (9)
C11—H11	0.9300	Hg2—N6^ii	2.442 (9)
C12—N2	1.305 (13)	N1—Hg1^i	2.359 (9)
C12—N4	1.356 (12)	N2—N3	1.381 (11)
C13—N3	1.296 (12)	N4—N5	1.400 (11)
C13—N4	1.366 (12)	N5—H5A	0.9360
C13—C14	1.477 (13)	N5—H5B	0.9187
C14—C18	1.356 (15)
N1—C1—C2	124.0 (11)	N6—C16—C17	121.3 (10)
N1—C1—H1	118.0	N6—C16—H16	119.3
C2—C1—H1	118.0	C17—C16—H16	119.3
C1—C2—C3	119.9 (11)	C16—C17—C18	119.1 (11)
C1—C2—H2	120.0	C16—C17—H17	120.5
C3—C2—H2	120.0	C18—C17—H17	120.5
C4—C3—C2	116.3 (10)	C14—C18—C17	119.3 (11)
C4—C3—C6	122.5 (9)	C14—C18—H18	120.4
C2—C3—C6	121.3 (9)	C17—C18—H18	120.4
C5—C4—C3	120.5 (10)	N7—C19—C20	172 (4)
C5—C4—H4	119.7	C19—C20—H20A	109.5
C3—C4—H4	119.7	C19—C20—H20B	109.5
N1—C5—C4	122.7 (10)	H20A—C20—H20B	109.5
N1—C5—H5	118.7	C19—C20—H20C	109.5
C4—C5—H5	118.7	H20A—C20—H20C	109.5
C11—C6—C7	117.7 (9)	H20B—C20—H20C	109.5
C11—C6—C3	121.8 (9)	N1^i—Hg1—N2	86.5 (3)
C7—C6—C3	120.4 (8)	N1^i—Hg1—I1	114.9 (2)
C8—C7—C6	121.2 (9)	N2—Hg1—I1	106.8 (2)
C8—C7—H7	119.4	N1^i—Hg1—I2	101.0 (2)
C6—C7—H7	119.4	N2—Hg1—I2	97.08 (19)
C9—C8—C7	121.3 (10)	I1—Hg1—I2	137.44 (4)
C9—C8—H8	119.4	N6—Hg2—N6^ii	81.9 (4)
C7—C8—H8	119.4	N6—Hg2—I4	106.2 (2)
C8—C9—C10	118.5 (10)	N6^ii—Hg2—I4	106.2 (2)
C8—C9—H9	120.7	N6—Hg2—I3	104.6 (2)
C10—C9—H9	120.7	N6^ii—Hg2—I3	104.6 (2)
C11—C10—C9	120.1 (9)	I4—Hg2—I3	138.85 (7)
C11—C10—C12	122.8 (9)	C1—N1—C5	116.4 (10)
C9—C10—C12	116.7 (9)	C1—N1—Hg1^i	119.5 (7)
C10—C11—C6	121.2 (9)	C5—N1—Hg1^i	124.1 (7)
C10—C11—H11	119.4	C12—N2—N3	107.3 (8)
C6—C11—H11	119.4	C12—N2—Hg1	130.2 (6)
N2—C12—N4	110.0 (8)	N3—N2—Hg1	120.9 (6)
N2—C12—C10	124.3 (9)	C13—N3—N2	107.6 (8)
N4—C12—C10	125.6 (9)	C12—N4—C13	105.1 (8)
N3—C13—N4	110.0 (8)	C12—N4—N5	130.5 (8)
N3—C13—C14	124.1 (9)	C13—N4—N5	124.1 (7)
N4—C13—C14	125.8 (9)	N4—N5—H5A	106.7
C18—C14—C15	118.8 (9)	N4—N5—H5B	107.6
C18—C14—C13	123.9 (10)	H5A—N5—H5B	111.6
C15—C14—C13	117.4 (9)	C16—N6—C15	119.2 (9)
N6—C15—C14	122.4 (10)	C16—N6—Hg2	120.5 (7)
N6—C15—H15	118.8	C15—N6—Hg2	119.9 (7)
C14—C15—H15	118.8
N1—C1—C2—C3	−2 (2)	C2—C1—N1—Hg1^i	−179.5 (12)
C1—C2—C3—C4	−1.0 (19)	C4—C5—N1—C1	1.6 (18)
C1—C2—C3—C6	179.8 (12)	C4—C5—N1—Hg1^i	−177.5 (9)
C2—C3—C4—C5	3.8 (18)	N4—C12—N2—N3	−0.1 (11)
C6—C3—C4—C5	−177.0 (10)	C10—C12—N2—N3	177.6 (9)
C3—C4—C5—N1	−4.3 (19)	N4—C12—N2—Hg1	165.1 (6)
C4—C3—C6—C11	1.2 (16)	C10—C12—N2—Hg1	−17.2 (15)
C2—C3—C6—C11	−179.6 (11)	N1^i—Hg1—N2—C12	−36.9 (9)
C4—C3—C6—C7	175.8 (11)	I1—Hg1—N2—C12	78.1 (9)
C2—C3—C6—C7	−5.1 (16)	I2—Hg1—N2—C12	−137.6 (9)
C11—C6—C7—C8	−1.9 (16)	N1^i—Hg1—N2—N3	126.5 (8)
C3—C6—C7—C8	−176.7 (10)	I1—Hg1—N2—N3	−118.4 (7)
C6—C7—C8—C9	2.4 (19)	I2—Hg1—N2—N3	25.9 (7)
C7—C8—C9—C10	−2.0 (17)	N4—C13—N3—N2	−0.4 (11)
C8—C9—C10—C11	1.1 (16)	C14—C13—N3—N2	−178.0 (9)
C8—C9—C10—C12	173.7 (10)	C12—N2—N3—C13	0.3 (11)
C9—C10—C11—C6	−0.7 (15)	Hg1—N2—N3—C13	−166.6 (7)
C12—C10—C11—C6	−172.8 (9)	N2—C12—N4—C13	−0.2 (11)
C7—C6—C11—C10	1.1 (15)	C10—C12—N4—C13	−177.8 (9)
C3—C6—C11—C10	175.8 (9)	N2—C12—N4—N5	173.1 (10)
C11—C10—C12—N2	123.8 (11)	C10—C12—N4—N5	−4.5 (16)
C9—C10—C12—N2	−48.6 (14)	N3—C13—N4—C12	0.3 (11)
C11—C10—C12—N4	−59.0 (14)	C14—C13—N4—C12	177.9 (9)
C9—C10—C12—N4	128.7 (11)	N3—C13—N4—N5	−173.4 (9)
N3—C13—C14—C18	−138.5 (12)	C14—C13—N4—N5	4.1 (15)
N4—C13—C14—C18	44.3 (17)	C17—C16—N6—C15	0.7 (18)
N3—C13—C14—C15	39.9 (15)	C17—C16—N6—Hg2	173.1 (10)
N4—C13—C14—C15	−137.4 (11)	C14—C15—N6—C16	−0.9 (17)
C18—C14—C15—N6	1.2 (17)	C14—C15—N6—Hg2	−173.3 (8)
C13—C14—C15—N6	−177.3 (10)	N6^ii—Hg2—N6—C16	−83.0 (9)
N6—C16—C17—C18	−1 (2)	I4—Hg2—N6—C16	21.6 (9)
C15—C14—C18—C17	−1.3 (19)	I3—Hg2—N6—C16	173.9 (8)
C13—C14—C18—C17	177.0 (12)	N6^ii—Hg2—N6—C15	89.3 (8)
C16—C17—C18—C14	1 (2)	I4—Hg2—N6—C15	−166.1 (8)
C2—C1—N1—C5	1 (2)	I3—Hg2—N6—C15	−13.7 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···N3^iii	0.92	2.42	3.173 (12)	139
N5—H5A···I3^iii	0.94	2.86	3.706 (10)	150
C7—H7···I1^iv	0.93	3.02	3.842 (10)	148

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