3,5-Bis{4-[(benzimidazol-1-yl)methyl]phenyl}-4H-1,2,4-triazol-4-amine and its one-dimensional polymeric complex with HgCl₂

The mol­ecule of 3,5-bis­{4-[(benzimidazol-1-yl)methyl]phenyl}-4H-1,2,4-triazol-4-amine (L), C₃₀H₂₄N₈, has an antiperiplanar conformation of the two terminal benzimidazole groups and forms two-dimensional networks along the crystallographic b axis via two types of inter­molecular hy­drogen bonds. However, in catena-poly[[[dichloridomercury(II)]-[mu]-3,5-bis­{4-[(benzimidazol-1-yl)methyl]phenyl}-4H-1,2,4-triazol-4-amine] dichloro­methane hemisolvate], {[HgCl₂(C₃₀H₂₄N₈)]·0.5CH₂Cl₂}_n, synthesized by the combination of L with HgCl₂, the L ligand adopts a synperiplanar conformation. The Hg^II cation lies in a distorted tetra­hedral environment, which is defined by two N atoms and two Cl atoms to form a one-dimensional zigzag chain. These zigzag chains stack via hydrogen bonds which expand the dimensionality of the structure from one to two.

S1. Comment

Organometallic complexes have attracted considerable attention because of their fascinating topological structures (Eddaoudi et al., 2002) and potential applications as functional materials in gas storage (Ma & Zhou, 2010), host–guest chemistry (Yoshizawa et al., 2006), catalysis (Kim et al., 2010) and luminescence (Cui et al., 2012). Over the past decade, the design and construction of rigid organic ligands bridged by 1,2,4-triazol-4-amine has been pursued, due to their diversity in coordination chemistry and model applications in functional materials (Wang et al., 2007, 2009; Liu et al., 2009, 2010).

To date, various organic ligands have been used as molecular building blocks, but the use of 1,2,4-triazol-4-amine-based bent organic ligands as semi-rigid components has remained rare until recently. In order to investigate how the semi-rigid organic ligands bridged by 1,2,4-triazol-4-amine affect the arrangement of molecular complexes in self-assembled aggregates, we synthesized a new 1,2,4-triazol-4-amine bridging ligand, namely 3,5-bis{4-[(benzimidazol-1-yl)methyl]phenyl}-4H-1,2,4-triazol-4-amine, denoted L or (I). This compound introduces two large aromatic benzimidazole groups to the ligand. The combination of (I) with HgCl₂ afforded {[HgCl₂L].CH₂Cl₂}_n, (II), which features hydrogen-bonded stacking-driven two-dimensional networks.

Within the free ligand, (I) (Fig. 1), the terminal benzimidazole groups adopt a trans conformation with respect to the central bridging 1,2,4-triazol-4-amine group. The dihedral angles between the planes of the benzimidazole and triazole rings are 58.328 (2) and 89.328 (2)° [For which sides of the molecule?], and the dihedral angles between the benzimidazole and adjacent benzene rings are 78.663 (1) and 78.934 (2)° [For which sides of the molecule?]. The two benzene rings of (I) are almost coplanar, with a dihedral angle of 7.288 (1)°.

In the crystal structure, molecules of (I) are arranged in chains via N4—H4A···N8ⁱ hydrogen bonds along the crystallographic a axis (Table 1; symmetry codes given in Table 1). The chains stack via a second hydrogen-bond interaction (N4—H4B···N1ⁱⁱ) to form a two-dimensional network (Fig. 2). This is in contrast with 3,5-bis(2-chlorophenyl)-1H-1,2,4-triazol-4-amine (Zachara et al., 2004), the molecules of which are linked by hydrogen bonds to form a one-dimensional chain.

Compound (II) crystallizes with one unique four-coordinated Hg^II centre in a distorted tetrahedral {HgCl₂N₂} environment involving two Cl atoms (Cl1 and Cl2) and two N atoms [N1 and N6ⁱ; symmetry code: (i) x, -y + 3/2, z - 1/2] from two different ligands (Fig. 3). Neighbouring Hg^II cations are bound together by triazole atom N1 and the terminal benzimidazole N atoms of the L ligands to form an {HgCl₂L} one-dimensional zigzag chain. The coordination behaviour of the Hg^II cation is similar to that observed in Hg[1-(pyridin-2-ylmethyl)-1H-benzotriazole]Cl₂ (Liu et al., 2008), where the 1-(pyridin-2-ylmethyl)-1H-benzotriazole ligand (L2) is also coordinated to an Hg^II centre to form a single chain. Similarly, in Hg(L2)Cl₂ there are no bonding interactions observed between adjacent chains.

The ligand L adopts different conformations under different conditions. In the solid state, the benzimidazole moieties adopt a trans geometry about the triazole core in the free ligand, whereas after coordination to Hg^II the benzimidazole groups adopt a cis conformation. Compared with those given above for (I), the dihedral angles in (II) between the planes of the benzimidazole groups and the adjacent benzene rings change to 89.328 (2) and 75.986 (2)° [For which sides of the molecule?]. These are nearly perpendicular, clearly as a result of coordination to Hg^II. Additionally, the dihedral angle formed by the two benzene rings changes from 7.288 (1)° in the free ligand, (I), to 18.829 (2)° in (II).

In the solid state, the zigzag chains in (II) are arranged along the a axis, where they interact via N4—H4A···Cl2ⁱⁱⁱ hydrogen-bond interactions, as shown in Fig. 4 (details in Table 2; symmetry code given in Table 2). The result is that a two-dimensional sheet is generated in the bc plane. The dichloromethane solvent molecules are located within the cavities formed by the layered stacking of (II) (Fig. 5).

In summary, a new compound with a common zigzag chain motif has been successfully obtained based on a new 1,2,4-triazol-4-amine bridging bent organic ligand, (I), and HgCl₂. The chains assemble through hydrogen bonds to form a two-dimensional network. The hydrogen-bond interactions play an important role in constructing high-dimensional supramolecular compounds.

Related literature

For related literature, see: Cui et al. (2012); Eddaoudi et al. (2002); Kim et al. (2010); Liu et al. (2008, 2009, 2010); Müller et al. (2006); Ma & Zhou (2010); Wang et al. (2007, 2009); Yoshizawa et al. (2006); Zachara et al. (2004).

S2. Experimental

For the preparation of (I), 80% hydrazine hydrate (2.8 g, 45 mmol) was added with stirring to a solution of 3,5-bis{4-[(benzimidazol-1-yl)methyl]phenyl}-1,3,4-oxadiazole (1.49 g, 3.0 mmol) in N,N-dimethylformamide (DMF; 20 ml). The mixture was stirred for 4 h at 423 K, then cooled to room temperature and poured into water (100 ml). The product was obtained as a white solid and purified on a silica-gel column using tetrahydrofuran as the eluent to afford L, (I), as a white crystalline solid (yield 1.00 g, 67%). A solution of L (5.00 mg, 0.010 mmol) in CH₂Cl₂ (10 ml) was left for about 2 d at room temperature, after which time colourless crystals were obtained (yield 3.24 mg, 65%). IR (KBr pellet, ν, cm^-): 3442 (s), 1633 (s), 1496 (s), 1385 (s), 1295 (m), 1200 (w), 1123 (w), 974 (w), 765 (s), 619 (m); ¹H NMR (300 MHz, DMSO, 298 K, TMS, δ, p.p.m.): 8.44 (s, 2H, –C₃H₂N₂–), 7.96–7.94, 7.47–7.44 (aabb, 8H, –C₆H₄–), 7.67–7.64 (d, 2H, –C₃H₂N₂–, 7.56–7.53 (d, 2H, –C₆H₃–), 7.23–7.18 (m, 4H, –C₆H₃–), 6.17 (s, 2H, –NH₂), 5.57 (s, 4H, –CH₂–). Elemental analysis, calculated for C₃₀H₂₄N₈: C 72.32, H 4.91, N 22.77%; found: C 72.56, H 4.87, N 22.57%.

For the synthesis of (II), a solution of HgCl₂ (5.42 mg, 0.020 mmol) in CH₃OH (5 ml) was layered on to a solution of (I) (9.93 mg, 0.020 mmol) in CH₂Cl₂ (8 ml). The mixture was left for about a week at room temperature and colourless crystals of (II) were obtained (yield 8.64 mg, 62%). IR (KBr pellet, ν, cm^-): 3447 (w), 1636 (s), 1509 (w), 1459 (m), 1384 (w), 1266 (m), 1193 (m), 740 (s). Elemental analysis, calculated for C₆₁H₅₀Cl₆Hg₂N₁₆: C 45.34, H 3.23, N 13.66%; found: C 45.20, H 3.11, N 13.82%.

S3. Refinement

The H atoms on N4 were located in a difference map and their positions were initially refined subject to an N—H distance restraint of 0.89 Å. Subsequently, these H atoms were treated in fixed positions, with U_iso(H) = 1.2U_eq(N). The remaining 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) or C—H = 0.97 Å and U_iso(H) = 1.2U_eq(C) (methylene).

In noncentrosymmetric (I), Friedel pairs were merged in the final refinement. In (II), Cl atoms bonded to C33 were located in a difference Fourier map and were subsequently restrained to a C—Cl distance of 1.78 (1) Å and a Cl···Cl distance of 2.80 (2) Å to retain a tetrahedral geometry. The main directions of movement of covalently bonded atoms C29, C30 and C31 were likewise restrained with an s.u. value of 0.005 Ų (Müller et al., 2006).

Computing details

For both 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. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Poor quality; please revise]
	Fig. 2. The two-dimensional structure of (I), constructed by hydrogen bonds (dashed lines). H atoms have been omitted for clarity. [Symmetry codes: (i) x - 1/2, -y + 1/2, z - 1/2; (ii) x - 1, y, z.]
	Fig. 3. The molecular structure of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) x, -y + 3/2, z - 1/2; (ii) x, -y + 3/2, z + 1/2.]
	Fig. 4. The two-dimensional structure of (II), constructed by hydrogen bonds (dashed lines). H atoms have been omitted for clarity. [Symmetry codes: (ii) x, -y + 3/2, z + 1/2; (iii) x, y - 1, z.]
	Fig. 5. The crystal packing of (II), viewed along the b axis. The dichloromethane solvent molecules are located in channels. [Poor quality; please revise]

(I) 3,5-Bis{4-[(benzimidazol-1-yl)methyl]phenyl}-4H-1,2,4-triazol-4-amine

Crystal data

C30H24N8	F(000) = 1040
Mr = 496.57	Dx = 1.364 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 815 reflections
a = 6.141 (2) Å	θ = 2.3–19.6°
b = 19.914 (6) Å	µ = 0.09 mm^−1
c = 19.910 (6) Å	T = 298 K
β = 96.537 (6)°	Plate, colourless
V = 2418.8 (13) Å^3	0.17 × 0.11 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2748 independent reflections
Radiation source: fine-focus sealed tube	2008 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 8.33 pixels mm^-1	θmax = 25.6°, θmin = 2.1°
ϕ and ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −22→23
Tmin = 0.986, Tmax = 0.992	l = −20→24
5790 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0369P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2748 reflections	Δρmax = 0.14 e Å^−3
343 parameters	Δρmin = −0.15 e Å^−3
2 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 6 (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
C1	0.0844 (9)	0.7758 (3)	−0.1891 (3)	0.0642 (15)
H1	−0.0197	0.8099	−0.1919	0.077*
C2	0.2671 (8)	0.7767 (2)	−0.1404 (2)	0.0449 (12)
C3	0.4198 (8)	0.7254 (2)	−0.1388 (2)	0.0427 (11)
C4	0.4001 (9)	0.6719 (2)	−0.1827 (2)	0.0635 (15)
H4	0.5048	0.6380	−0.1806	0.076*
C5	0.2176 (10)	0.6709 (3)	−0.2299 (3)	0.0694 (17)
H5	0.1970	0.6353	−0.2602	0.083*
C6	0.0656 (10)	0.7218 (3)	−0.2329 (3)	0.0703 (16)
H6	−0.0546	0.7199	−0.2658	0.084*
C7	0.5107 (11)	0.8003 (2)	−0.0606 (2)	0.0574 (15)
H7	0.5907	0.8226	−0.0249	0.069*
C8	0.7913 (9)	0.7097 (3)	−0.0689 (3)	0.0701 (15)
H8A	0.8766	0.7368	−0.0349	0.084*
H8B	0.8670	0.7101	−0.1090	0.084*
C9	0.7883 (8)	0.6390 (2)	−0.0433 (2)	0.0471 (11)
C10	0.9736 (8)	0.5995 (3)	−0.0493 (2)	0.0556 (13)
H10	1.0876	0.6166	−0.0711	0.067*
C11	0.9893 (8)	0.5349 (2)	−0.0229 (2)	0.0530 (12)
H11	1.1146	0.5095	−0.0264	0.064*
C12	0.8171 (7)	0.5080 (2)	0.00876 (19)	0.0404 (11)
C13	0.6322 (8)	0.5467 (2)	0.0121 (2)	0.0451 (11)
H13	0.5149	0.5291	0.0321	0.054*
C14	0.6186 (8)	0.6113 (2)	−0.0138 (2)	0.0472 (12)
H14	0.4920	0.6363	−0.0110	0.057*
C15	0.8474 (7)	0.4422 (2)	0.03978 (19)	0.0386 (10)
C16	0.7993 (7)	0.3416 (2)	0.08063 (19)	0.0403 (11)
C17	0.7076 (7)	0.2776 (2)	0.0998 (2)	0.0407 (11)
C18	0.8355 (8)	0.2208 (2)	0.0985 (2)	0.0505 (12)
H18	0.9689	0.2232	0.0807	0.061*
C19	0.7687 (9)	0.1605 (2)	0.1232 (2)	0.0542 (13)
H19	0.8580	0.1230	0.1216	0.065*
C20	0.5727 (8)	0.1546 (2)	0.1501 (2)	0.0466 (12)
C21	0.4440 (9)	0.2110 (3)	0.1501 (3)	0.0624 (14)
H21	0.3109	0.2083	0.1680	0.075*
C22	0.5062 (8)	0.2719 (3)	0.1243 (2)	0.0536 (13)
H22	0.4130	0.3088	0.1234	0.064*
C23	0.5040 (8)	0.0895 (2)	0.1806 (2)	0.0563 (13)
H23A	0.3560	0.0942	0.1925	0.068*
H23B	0.5035	0.0540	0.1472	0.068*
C24	0.6435 (9)	0.0920 (2)	0.3054 (2)	0.0563 (13)
H24	0.5298	0.1183	0.3179	0.068*
C25	0.9393 (8)	0.0366 (2)	0.3092 (2)	0.0457 (11)
C26	1.1378 (9)	0.0054 (2)	0.3271 (3)	0.0591 (14)
H26	1.2057	0.0081	0.3712	0.071*
C27	1.2336 (9)	−0.0297 (2)	0.2792 (3)	0.0617 (14)
H27	1.3692	−0.0499	0.2908	0.074*
C28	1.1312 (9)	−0.0358 (2)	0.2129 (3)	0.0598 (14)
H28	1.1966	−0.0616	0.1818	0.072*
C29	0.9361 (9)	−0.0044 (2)	0.1935 (2)	0.0554 (14)
H29	0.8688	−0.0076	0.1494	0.066*
C30	0.8420 (8)	0.0325 (2)	0.2417 (2)	0.0415 (11)
N1	1.0373 (6)	0.42256 (18)	0.07188 (18)	0.0493 (10)
N2	1.0063 (6)	0.35886 (18)	0.09779 (18)	0.0485 (10)
N3	0.6930 (5)	0.39314 (17)	0.04478 (16)	0.0393 (9)
N4	0.4818 (6)	0.38538 (18)	0.00842 (19)	0.0480 (10)
H4A	0.4807	0.3928	−0.0355	0.058*
H4B	0.4034	0.4155	0.0287	0.058*
N5	0.5785 (7)	0.74170 (19)	−0.08529 (18)	0.0506 (10)
N6	0.3272 (8)	0.8236 (2)	−0.0900 (2)	0.0618 (12)
N7	0.6508 (7)	0.07047 (18)	0.24115 (18)	0.0485 (10)
N8	0.8080 (7)	0.0730 (2)	0.34802 (19)	0.0585 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.058 (4)	0.064 (3)	0.070 (3)	0.016 (3)	0.006 (3)	0.019 (3)
C2	0.053 (3)	0.037 (3)	0.045 (3)	0.005 (2)	0.008 (2)	0.003 (2)
C3	0.054 (3)	0.041 (2)	0.032 (2)	−0.006 (2)	0.006 (2)	0.001 (2)
C4	0.079 (4)	0.056 (3)	0.055 (3)	0.005 (3)	0.004 (3)	−0.007 (3)
C5	0.091 (5)	0.068 (4)	0.046 (3)	−0.012 (3)	−0.004 (3)	−0.013 (3)
C6	0.073 (4)	0.087 (4)	0.047 (3)	−0.007 (4)	−0.014 (3)	0.006 (3)
C7	0.086 (5)	0.049 (3)	0.038 (3)	−0.022 (3)	0.011 (3)	−0.008 (2)
C8	0.048 (3)	0.077 (4)	0.084 (4)	−0.010 (3)	0.001 (3)	0.022 (3)
C9	0.038 (3)	0.060 (3)	0.041 (3)	−0.007 (3)	−0.006 (2)	0.007 (2)
C10	0.039 (3)	0.079 (4)	0.048 (3)	−0.008 (3)	0.002 (2)	0.016 (3)
C11	0.026 (3)	0.074 (3)	0.056 (3)	0.003 (3)	−0.003 (2)	0.008 (3)
C12	0.035 (3)	0.052 (3)	0.032 (2)	0.003 (2)	−0.0059 (19)	−0.008 (2)
C13	0.040 (3)	0.053 (3)	0.043 (2)	−0.002 (2)	0.005 (2)	0.001 (2)
C14	0.042 (3)	0.052 (3)	0.048 (3)	0.006 (2)	0.006 (2)	0.004 (2)
C15	0.036 (3)	0.048 (3)	0.030 (2)	0.006 (2)	−0.0047 (19)	−0.005 (2)
C16	0.033 (3)	0.053 (3)	0.034 (2)	0.007 (2)	−0.0041 (19)	−0.005 (2)
C17	0.031 (3)	0.051 (3)	0.038 (2)	0.003 (2)	−0.0043 (19)	0.001 (2)
C18	0.040 (3)	0.059 (3)	0.053 (3)	0.005 (3)	0.011 (2)	−0.003 (2)
C19	0.052 (3)	0.045 (3)	0.066 (3)	0.010 (2)	0.010 (3)	−0.005 (2)
C20	0.035 (3)	0.055 (3)	0.048 (3)	−0.004 (2)	−0.004 (2)	−0.001 (2)
C21	0.040 (3)	0.082 (4)	0.065 (3)	−0.003 (3)	0.004 (2)	0.017 (3)
C22	0.032 (3)	0.067 (3)	0.062 (3)	0.013 (3)	0.003 (2)	0.004 (3)
C23	0.041 (3)	0.067 (3)	0.059 (3)	−0.013 (3)	0.000 (2)	0.003 (3)
C24	0.054 (4)	0.065 (3)	0.053 (3)	−0.005 (3)	0.016 (3)	−0.008 (3)
C25	0.056 (3)	0.046 (3)	0.036 (2)	−0.009 (2)	0.006 (2)	−0.001 (2)
C26	0.066 (4)	0.060 (3)	0.049 (3)	−0.007 (3)	−0.006 (3)	0.008 (3)
C27	0.062 (4)	0.055 (3)	0.067 (4)	0.002 (3)	0.003 (3)	0.010 (3)
C28	0.068 (4)	0.050 (3)	0.064 (3)	−0.001 (3)	0.018 (3)	−0.004 (3)
C29	0.072 (4)	0.051 (3)	0.042 (3)	−0.020 (3)	0.007 (2)	−0.005 (2)
C30	0.053 (3)	0.040 (2)	0.032 (2)	−0.009 (2)	0.006 (2)	0.000 (2)
N1	0.037 (2)	0.058 (2)	0.050 (2)	0.010 (2)	−0.0060 (19)	−0.0017 (19)
N2	0.034 (2)	0.057 (2)	0.051 (2)	0.007 (2)	−0.0096 (18)	0.0021 (19)
N3	0.022 (2)	0.054 (2)	0.041 (2)	0.0055 (18)	−0.0060 (16)	−0.0020 (18)
N4	0.030 (2)	0.065 (3)	0.045 (2)	−0.0010 (19)	−0.0121 (17)	0.0018 (18)
N5	0.052 (3)	0.049 (2)	0.049 (2)	−0.002 (2)	−0.002 (2)	0.0064 (19)
N6	0.077 (3)	0.047 (2)	0.062 (3)	0.003 (2)	0.014 (2)	−0.005 (2)
N7	0.050 (3)	0.058 (2)	0.037 (2)	−0.008 (2)	−0.0005 (19)	0.0016 (19)
N8	0.068 (3)	0.065 (3)	0.042 (2)	−0.008 (2)	0.005 (2)	−0.007 (2)

Geometric parameters (Å, º)

C1—C6	1.381 (7)	C16—C17	1.463 (6)
C1—C2	1.398 (7)	C17—C18	1.379 (6)
C1—H1	0.9300	C17—C22	1.385 (6)
C2—C3	1.385 (6)	C18—C19	1.377 (6)
C2—N6	1.388 (6)	C18—H18	0.9300
C3—C4	1.374 (6)	C19—C20	1.377 (6)
C3—N5	1.398 (6)	C19—H19	0.9300
C4—C5	1.379 (7)	C20—C21	1.374 (7)
C4—H4	0.9300	C20—C23	1.512 (6)
C5—C6	1.375 (7)	C21—C22	1.387 (7)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—N6	1.295 (7)	C23—N7	1.470 (5)
C7—N5	1.351 (6)	C23—H23A	0.9700
C7—H7	0.9300	C23—H23B	0.9700
C8—N5	1.457 (6)	C24—N8	1.300 (6)
C8—C9	1.498 (6)	C24—N7	1.354 (5)
C8—H8A	0.9700	C24—H24	0.9300
C8—H8B	0.9700	C25—C26	1.379 (7)
C9—C14	1.370 (6)	C25—N8	1.384 (6)
C9—C10	1.400 (7)	C25—C30	1.408 (6)
C10—C11	1.387 (6)	C26—C27	1.368 (7)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.398 (6)	C27—C28	1.401 (7)
C11—H11	0.9300	C27—H27	0.9300
C12—C13	1.380 (6)	C28—C29	1.368 (7)
C12—C15	1.452 (6)	C28—H28	0.9300
C13—C14	1.384 (6)	C29—C30	1.386 (6)
C13—H13	0.9300	C29—H29	0.9300
C14—H14	0.9300	C30—N7	1.395 (5)
C15—N1	1.323 (5)	N1—N2	1.390 (5)
C15—N3	1.373 (5)	N3—N4	1.420 (4)
C16—N2	1.323 (5)	N4—H4A	0.8859
C16—N3	1.371 (5)	N4—H4B	0.8947
C6—C1—C2	116.9 (5)	C17—C18—H18	119.5
C6—C1—H1	121.6	C20—C19—C18	121.5 (5)
C2—C1—H1	121.6	C20—C19—H19	119.2
C3—C2—N6	110.9 (4)	C18—C19—H19	119.2
C3—C2—C1	119.6 (4)	C21—C20—C19	117.3 (5)
N6—C2—C1	129.5 (5)	C21—C20—C23	121.0 (5)
C4—C3—C2	123.2 (4)	C19—C20—C23	121.7 (5)
C4—C3—N5	131.9 (5)	C20—C21—C22	122.1 (5)
C2—C3—N5	104.9 (4)	C20—C21—H21	118.9
C3—C4—C5	116.8 (5)	C22—C21—H21	118.9
C3—C4—H4	121.6	C17—C22—C21	119.8 (5)
C5—C4—H4	121.6	C17—C22—H22	120.1
C6—C5—C4	120.9 (5)	C21—C22—H22	120.1
C6—C5—H5	119.6	N7—C23—C20	112.2 (4)
C4—C5—H5	119.6	N7—C23—H23A	109.2
C5—C6—C1	122.6 (5)	C20—C23—H23A	109.2
C5—C6—H6	118.7	N7—C23—H23B	109.2
C1—C6—H6	118.7	C20—C23—H23B	109.2
N6—C7—N5	115.7 (5)	H23A—C23—H23B	107.9
N6—C7—H7	122.2	N8—C24—N7	114.7 (5)
N5—C7—H7	122.2	N8—C24—H24	122.6
N5—C8—C9	116.3 (4)	N7—C24—H24	122.6
N5—C8—H8A	108.2	C26—C25—N8	130.2 (4)
C9—C8—H8A	108.2	C26—C25—C30	119.2 (4)
N5—C8—H8B	108.2	N8—C25—C30	110.6 (4)
C9—C8—H8B	108.2	C27—C26—C25	119.1 (5)
H8A—C8—H8B	107.4	C27—C26—H26	120.4
C14—C9—C10	118.4 (4)	C25—C26—H26	120.4
C14—C9—C8	124.3 (4)	C26—C27—C28	121.3 (5)
C10—C9—C8	117.3 (5)	C26—C27—H27	119.4
C11—C10—C9	120.8 (5)	C28—C27—H27	119.4
C11—C10—H10	119.6	C29—C28—C27	120.7 (5)
C9—C10—H10	119.6	C29—C28—H28	119.6
C10—C11—C12	120.1 (5)	C27—C28—H28	119.6
C10—C11—H11	119.9	C28—C29—C30	117.9 (4)
C12—C11—H11	119.9	C28—C29—H29	121.1
C13—C12—C11	118.5 (4)	C30—C29—H29	121.1
C13—C12—C15	123.4 (4)	C29—C30—N7	134.3 (4)
C11—C12—C15	118.1 (4)	C29—C30—C25	121.7 (5)
C12—C13—C14	121.0 (4)	N7—C30—C25	104.0 (4)
C12—C13—H13	119.5	C15—N1—N2	107.4 (4)
C14—C13—H13	119.5	C16—N2—N1	108.0 (3)
C9—C14—C13	121.2 (4)	C16—N3—C15	106.2 (3)
C9—C14—H14	119.4	C16—N3—N4	122.5 (3)
C13—C14—H14	119.4	C15—N3—N4	129.7 (3)
N1—C15—N3	109.4 (4)	N3—N4—H4A	112.9
N1—C15—C12	122.4 (4)	N3—N4—H4B	101.7
N3—C15—C12	128.1 (4)	H4A—N4—H4B	113.0
N2—C16—N3	109.1 (4)	C7—N5—C3	105.1 (4)
N2—C16—C17	123.1 (4)	C7—N5—C8	127.0 (5)
N3—C16—C17	127.8 (4)	C3—N5—C8	126.8 (4)
C18—C17—C22	118.3 (5)	C7—N6—C2	103.4 (4)
C18—C17—C16	118.2 (4)	C24—N7—C30	106.4 (4)
C22—C17—C16	123.3 (4)	C24—N7—C23	127.5 (4)
C19—C18—C17	120.9 (5)	C30—N7—C23	125.7 (4)
C19—C18—H18	119.5	C24—N8—C25	104.2 (4)
C6—C1—C2—C3	1.1 (7)	C25—C26—C27—C28	−1.6 (7)
C6—C1—C2—N6	−179.5 (5)	C26—C27—C28—C29	2.8 (8)
N6—C2—C3—C4	179.4 (5)	C27—C28—C29—C30	−1.2 (7)
C1—C2—C3—C4	−1.0 (7)	C28—C29—C30—N7	179.7 (4)
N6—C2—C3—N5	0.1 (5)	C28—C29—C30—C25	−1.5 (7)
C1—C2—C3—N5	179.7 (4)	C26—C25—C30—C29	2.6 (7)
C2—C3—C4—C5	0.1 (7)	N8—C25—C30—C29	−176.6 (4)
N5—C3—C4—C5	179.1 (5)	C26—C25—C30—N7	−178.3 (4)
C3—C4—C5—C6	0.9 (8)	N8—C25—C30—N7	2.5 (5)
C4—C5—C6—C1	−0.8 (9)	N3—C15—N1—N2	0.6 (5)
C2—C1—C6—C5	−0.2 (8)	C12—C15—N1—N2	177.3 (4)
N5—C8—C9—C14	−22.8 (7)	N3—C16—N2—N1	−0.8 (4)
N5—C8—C9—C10	158.4 (4)	C17—C16—N2—N1	−179.6 (4)
C14—C9—C10—C11	−3.0 (7)	C15—N1—N2—C16	0.1 (5)
C8—C9—C10—C11	175.8 (4)	N2—C16—N3—C15	1.2 (4)
C9—C10—C11—C12	1.3 (7)	C17—C16—N3—C15	179.9 (4)
C10—C11—C12—C13	1.0 (6)	N2—C16—N3—N4	167.7 (4)
C10—C11—C12—C15	−175.7 (4)	C17—C16—N3—N4	−13.5 (6)
C11—C12—C13—C14	−1.5 (6)	N1—C15—N3—C16	−1.1 (4)
C15—C12—C13—C14	174.9 (4)	C12—C15—N3—C16	−177.6 (4)
C10—C9—C14—C13	2.5 (6)	N1—C15—N3—N4	−166.3 (4)
C8—C9—C14—C13	−176.3 (4)	C12—C15—N3—N4	17.2 (7)
C12—C13—C14—C9	−0.2 (6)	N6—C7—N5—C3	1.4 (6)
C13—C12—C15—N1	−138.9 (4)	N6—C7—N5—C8	170.2 (5)
C11—C12—C15—N1	37.5 (6)	C4—C3—N5—C7	−180.0 (5)
C13—C12—C15—N3	37.1 (6)	C2—C3—N5—C7	−0.8 (5)
C11—C12—C15—N3	−146.5 (4)	C4—C3—N5—C8	11.2 (8)
N2—C16—C17—C18	−39.0 (6)	C2—C3—N5—C8	−169.7 (4)
N3—C16—C17—C18	142.4 (4)	C9—C8—N5—C7	124.6 (5)
N2—C16—C17—C22	135.6 (5)	C9—C8—N5—C3	−68.8 (6)
N3—C16—C17—C22	−42.9 (6)	N5—C7—N6—C2	−1.2 (6)
C22—C17—C18—C19	−2.3 (7)	C3—C2—N6—C7	0.6 (5)
C16—C17—C18—C19	172.6 (4)	C1—C2—N6—C7	−178.9 (5)
C17—C18—C19—C20	−0.1 (7)	N8—C24—N7—C30	0.4 (5)
C18—C19—C20—C21	1.3 (7)	N8—C24—N7—C23	−172.6 (4)
C18—C19—C20—C23	−176.7 (4)	C29—C30—N7—C24	177.2 (5)
C19—C20—C21—C22	0.0 (7)	C25—C30—N7—C24	−1.7 (4)
C23—C20—C21—C22	178.1 (4)	C29—C30—N7—C23	−9.6 (7)
C18—C17—C22—C21	3.6 (7)	C25—C30—N7—C23	171.5 (4)
C16—C17—C22—C21	−171.0 (4)	C20—C23—N7—C24	83.6 (6)
C20—C21—C22—C17	−2.5 (8)	C20—C23—N7—C30	−88.2 (5)
C21—C20—C23—N7	−113.4 (5)	N7—C24—N8—C25	1.1 (6)
C19—C20—C23—N7	64.5 (6)	C26—C25—N8—C24	178.6 (5)
N8—C25—C26—C27	178.1 (4)	C30—C25—N8—C24	−2.2 (5)
C30—C25—C26—C27	−1.0 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N8^i	0.89	2.53	3.354 (5)	155
N4—H4B···N1^ii	0.89	2.50	3.222 (6)	138

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

(II) catena-poly[[[dichloridomercury(II)]-µ-3,5-bis{4-[(benzimidazol-1- yl)methyl]phenyl}-4H-1,2,4-triazol-4-amine] dichloromethane hemisolvate]

Crystal data

[HgCl2(C30H24N8)]·0.5CH2Cl2	F(000) = 1580
Mr = 810.53	Dx = 1.657 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5424 reflections
a = 16.627 (3) Å	θ = 2.2–24.9°
b = 10.6199 (18) Å	µ = 5.02 mm^−1
c = 20.082 (3) Å	T = 298 K
β = 113.586 (2)°	Block, colourless
V = 3249.9 (10) Å^3	0.40 × 0.38 × 0.34 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	6097 independent reflections
Radiation source: fine-focus sealed tube	4599 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.33 pixels mm^-1	θmax = 25.6°, θmin = 2.1°
ϕ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −11→12
Tmin = 0.239, Tmax = 0.280	l = −24→21
16724 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.9206P] where P = (Fo^2 + 2Fc^2)/3
6097 reflections	(Δ/σ)max = 0.002
397 parameters	Δρmax = 1.22 e Å^−3
6 restraints	Δρmin = −0.64 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	0.2929 (4)	0.1686 (6)	0.7716 (3)	0.0679 (17)
H1	0.2704	0.1287	0.8017	0.081*
C2	0.3518 (4)	0.2680 (5)	0.7960 (3)	0.0473 (13)
C3	0.3825 (3)	0.3279 (6)	0.7500 (3)	0.0495 (13)
C4	0.3583 (4)	0.2890 (6)	0.6783 (3)	0.0646 (17)
H4	0.3803	0.3284	0.6478	0.078*
C5	0.3018 (5)	0.1923 (7)	0.6551 (4)	0.082 (2)
H5	0.2839	0.1649	0.6073	0.098*
C6	0.2694 (5)	0.1321 (7)	0.7008 (4)	0.083 (2)
H6	0.2307	0.0652	0.6827	0.099*
C7	0.4375 (4)	0.4134 (5)	0.8577 (3)	0.0505 (13)
H7	0.4696	0.4671	0.8956	0.061*
C8	0.4972 (4)	0.4987 (6)	0.7699 (3)	0.0666 (17)
H8A	0.5362	0.4447	0.7575	0.080*
H8B	0.5330	0.5495	0.8113	0.080*
C9	0.4485 (3)	0.5848 (6)	0.7062 (3)	0.0544 (15)
C10	0.3975 (4)	0.6818 (6)	0.7121 (3)	0.0542 (14)
H10	0.3889	0.6921	0.7548	0.065*
C11	0.3583 (4)	0.7649 (5)	0.6546 (3)	0.0522 (14)
H11	0.3237	0.8306	0.6590	0.063*
C12	0.3706 (4)	0.7502 (5)	0.5915 (3)	0.0457 (13)
C13	0.4207 (4)	0.6519 (6)	0.5858 (3)	0.0579 (15)
H13	0.4284	0.6410	0.5428	0.069*
C14	0.4596 (4)	0.5695 (6)	0.6417 (3)	0.0594 (15)
H14	0.4934	0.5034	0.6366	0.071*
C15	0.3380 (3)	0.8477 (5)	0.5345 (3)	0.0455 (12)
C16	0.2797 (3)	0.9393 (5)	0.4296 (2)	0.0428 (12)
C17	0.2339 (3)	0.9643 (5)	0.3522 (2)	0.0439 (12)
C18	0.1805 (4)	1.0706 (5)	0.3297 (3)	0.0582 (15)
H18	0.1724	1.1222	0.3639	0.070*
C19	0.1394 (4)	1.0992 (5)	0.2559 (3)	0.0605 (15)
H19	0.1048	1.1711	0.2410	0.073*
C20	0.1498 (3)	1.0212 (5)	0.2048 (3)	0.0494 (13)
C21	0.2011 (4)	0.9170 (5)	0.2269 (3)	0.0596 (15)
H21	0.2078	0.8644	0.1924	0.072*
C22	0.2446 (4)	0.8873 (5)	0.3013 (3)	0.0528 (14)
H22	0.2801	0.8163	0.3159	0.063*
C23	0.1038 (5)	1.0571 (6)	0.1257 (3)	0.0731 (19)
H23A	0.0433	1.0780	0.1156	0.088*
H23B	0.1315	1.1319	0.1168	0.088*
C24	0.1647 (4)	0.9441 (7)	0.0470 (3)	0.0694 (17)
H24	0.2110	0.9997	0.0557	0.083*
C25	0.0777 (5)	0.7911 (6)	0.0073 (4)	0.0733 (18)
C26	0.0486 (4)	0.8590 (6)	0.0517 (3)	0.0634 (17)
C27	−0.0272 (5)	0.8288 (9)	0.0619 (4)	0.088 (2)
H27	−0.0466	0.8767	0.0914	0.106*
C28	−0.0717 (7)	0.7234 (11)	0.0254 (7)	0.119 (4)
H28	−0.1226	0.6992	0.0307	0.143*
C29	−0.0438 (7)	0.6535 (9)	−0.0182 (6)	0.120 (4)
H29	−0.0757	0.5831	−0.0419	0.144*
C30	0.0314 (7)	0.6859 (8)	−0.0277 (5)	0.102 (3)
H30	0.0505	0.6376	−0.0572	0.122*
C31	0.0981 (11)	0.9236 (17)	0.7769 (8)	0.145 (10)	0.50
H31A	0.1551	0.9285	0.8171	0.174*	0.50
H31B	0.0610	0.8651	0.7888	0.174*	0.50
Cl1	0.51584 (11)	1.22810 (16)	0.56785 (9)	0.0722 (4)
Cl2	0.26955 (13)	1.38869 (17)	0.45231 (11)	0.0874 (5)
Cl3	0.0483 (6)	1.0747 (10)	0.7525 (6)	0.265 (5)	0.50
Cl4	0.1068 (10)	0.8832 (9)	0.6947 (7)	0.358 (9)	0.50
Hg1	0.371973 (15)	1.22327 (2)	0.467698 (11)	0.05320 (11)
N1	0.3515 (3)	0.9673 (4)	0.5471 (2)	0.0507 (11)
N2	0.3141 (3)	1.0265 (4)	0.4796 (2)	0.0504 (11)
N3	0.2942 (3)	0.8264 (4)	0.4617 (2)	0.0431 (10)
N4	0.2625 (3)	0.7124 (4)	0.4262 (2)	0.0561 (13)
H4B	0.2237	0.6805	0.4419	0.084*
H4A	0.3070	0.6590	0.4361	0.084*
N5	0.4387 (3)	0.4201 (4)	0.7905 (2)	0.0494 (11)
N6	0.3877 (3)	0.3256 (4)	0.8638 (2)	0.0452 (10)
N7	0.1055 (3)	0.9591 (5)	0.0766 (2)	0.0597 (13)
N8	0.1522 (4)	0.8465 (6)	0.0057 (3)	0.0791 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.073 (4)	0.070 (4)	0.062 (4)	−0.014 (4)	0.028 (3)	−0.013 (3)
C2	0.053 (3)	0.049 (3)	0.041 (3)	0.000 (3)	0.019 (3)	−0.002 (2)
C3	0.045 (3)	0.064 (3)	0.037 (3)	0.010 (3)	0.014 (2)	0.007 (3)
C4	0.067 (4)	0.088 (5)	0.044 (4)	0.008 (4)	0.028 (3)	0.003 (3)
C5	0.086 (5)	0.097 (6)	0.059 (4)	0.005 (4)	0.026 (4)	−0.023 (4)
C6	0.085 (5)	0.082 (5)	0.075 (5)	−0.017 (4)	0.027 (4)	−0.035 (4)
C7	0.054 (3)	0.059 (3)	0.032 (3)	0.002 (3)	0.009 (3)	0.005 (2)
C8	0.047 (3)	0.089 (4)	0.053 (3)	−0.011 (3)	0.010 (3)	0.030 (3)
C9	0.039 (3)	0.074 (4)	0.044 (3)	−0.006 (3)	0.011 (3)	0.020 (3)
C10	0.053 (3)	0.075 (4)	0.032 (3)	−0.007 (3)	0.015 (3)	0.008 (3)
C11	0.056 (3)	0.057 (3)	0.038 (3)	−0.007 (3)	0.015 (3)	0.002 (2)
C12	0.055 (3)	0.046 (3)	0.032 (3)	−0.007 (2)	0.012 (2)	0.004 (2)
C13	0.069 (4)	0.064 (4)	0.040 (3)	−0.002 (3)	0.022 (3)	0.009 (3)
C14	0.069 (4)	0.061 (4)	0.052 (3)	0.008 (3)	0.028 (3)	0.015 (3)
C15	0.052 (3)	0.052 (3)	0.028 (3)	−0.004 (3)	0.012 (2)	0.004 (2)
C16	0.048 (3)	0.045 (3)	0.034 (3)	−0.001 (2)	0.015 (2)	0.004 (2)
C17	0.042 (3)	0.053 (3)	0.031 (3)	−0.005 (2)	0.009 (2)	0.004 (2)
C18	0.070 (4)	0.054 (3)	0.043 (3)	0.008 (3)	0.015 (3)	−0.001 (3)
C19	0.065 (4)	0.052 (3)	0.050 (3)	0.018 (3)	0.009 (3)	0.012 (3)
C20	0.046 (3)	0.062 (3)	0.035 (3)	0.010 (3)	0.011 (2)	0.013 (3)
C21	0.078 (4)	0.060 (4)	0.043 (3)	0.020 (3)	0.027 (3)	0.006 (3)
C22	0.058 (3)	0.060 (3)	0.032 (3)	0.014 (3)	0.009 (3)	0.009 (2)
C23	0.093 (5)	0.076 (4)	0.038 (3)	0.021 (4)	0.014 (3)	0.014 (3)
C24	0.062 (4)	0.092 (5)	0.052 (4)	0.005 (4)	0.021 (3)	0.017 (4)
C25	0.080 (5)	0.075 (4)	0.049 (4)	0.022 (3)	0.008 (4)	0.015 (3)
C26	0.058 (4)	0.080 (5)	0.043 (3)	0.016 (3)	0.010 (3)	0.027 (3)
C27	0.076 (5)	0.110 (6)	0.074 (5)	0.016 (5)	0.025 (4)	0.035 (5)
C28	0.091 (7)	0.120 (9)	0.120 (9)	−0.016 (6)	0.017 (6)	0.052 (7)
C29	0.115 (7)	0.075 (6)	0.123 (8)	−0.002 (5)	−0.003 (6)	0.030 (5)
C30	0.117 (6)	0.074 (4)	0.081 (5)	0.028 (4)	0.004 (5)	0.004 (4)
C31	0.061 (10)	0.21 (3)	0.136 (17)	−0.012 (13)	0.012 (11)	0.086 (18)
Cl1	0.0664 (10)	0.0896 (11)	0.0531 (9)	−0.0014 (8)	0.0162 (8)	0.0094 (8)
Cl2	0.1004 (14)	0.0686 (10)	0.1054 (14)	0.0271 (10)	0.0540 (12)	−0.0017 (10)
Cl3	0.220 (9)	0.299 (12)	0.321 (12)	−0.151 (9)	0.155 (9)	−0.056 (10)
Cl4	0.50 (2)	0.145 (8)	0.298 (14)	−0.040 (11)	0.021 (14)	−0.026 (9)
Hg1	0.06895 (18)	0.04852 (15)	0.04283 (15)	0.00558 (10)	0.02311 (12)	−0.00091 (9)
N1	0.064 (3)	0.053 (3)	0.029 (2)	−0.006 (2)	0.012 (2)	−0.0017 (19)
N2	0.067 (3)	0.047 (2)	0.031 (2)	−0.002 (2)	0.014 (2)	0.0024 (19)
N3	0.049 (2)	0.046 (2)	0.031 (2)	−0.005 (2)	0.0129 (19)	0.0003 (19)
N4	0.074 (3)	0.047 (3)	0.040 (3)	−0.017 (2)	0.015 (2)	−0.003 (2)
N5	0.045 (3)	0.063 (3)	0.036 (2)	−0.003 (2)	0.010 (2)	0.013 (2)
N6	0.052 (3)	0.051 (2)	0.035 (2)	−0.008 (2)	0.020 (2)	0.002 (2)
N7	0.066 (3)	0.074 (3)	0.031 (2)	0.008 (3)	0.010 (2)	0.013 (2)
N8	0.082 (4)	0.095 (5)	0.060 (4)	0.023 (4)	0.028 (3)	0.007 (3)

Geometric parameters (Å, º)

C1—C6	1.371 (8)	C19—C20	1.382 (7)
C1—C2	1.390 (8)	C19—H19	0.9300
C1—H1	0.9300	C20—C21	1.359 (8)
C2—C3	1.376 (8)	C20—C23	1.510 (7)
C2—N6	1.390 (7)	C21—C22	1.411 (7)
C3—N5	1.373 (7)	C21—H21	0.9300
C3—C4	1.394 (8)	C22—H22	0.9300
C4—C5	1.344 (10)	C23—N7	1.442 (7)
C4—H4	0.9300	C23—H23A	0.9700
C5—C6	1.390 (10)	C23—H23B	0.9700
C5—H5	0.9300	C24—N8	1.292 (9)
C6—H6	0.9300	C24—N7	1.348 (8)
C7—N6	1.284 (7)	C24—H24	0.9300
C7—N5	1.360 (6)	C25—C26	1.377 (9)
C7—H7	0.9300	C25—C30	1.379 (11)
C8—N5	1.462 (7)	C25—N8	1.383 (10)
C8—C9	1.517 (7)	C26—N7	1.376 (8)
C8—H8A	0.9700	C26—C27	1.393 (9)
C8—H8B	0.9700	C27—C28	1.380 (13)
C9—C10	1.369 (8)	C27—H27	0.9300
C9—C14	1.389 (7)	C28—C29	1.363 (14)
C10—C11	1.391 (8)	C28—H28	0.9300
C10—H10	0.9300	C29—C30	1.382 (13)
C11—C12	1.371 (8)	C29—H29	0.9300
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.368 (8)	C31—Cl4	1.766 (9)
C12—C15	1.477 (7)	C31—Cl3	1.782 (9)
C13—C14	1.364 (7)	C31—H31A	0.9700
C13—H13	0.9300	C31—H31B	0.9700
C14—H14	0.9300	Cl1—Hg1	2.4331 (17)
C15—N1	1.297 (7)	Cl2—Hg1	2.3793 (17)
C15—N3	1.367 (6)	Hg1—N6^i	2.265 (4)
C16—N2	1.316 (6)	Hg1—N2	2.353 (4)
C16—N3	1.337 (6)	N1—N2	1.395 (5)
C16—C17	1.455 (6)	N3—N4	1.397 (6)
C17—C22	1.374 (7)	N4—H4B	0.8900
C17—C18	1.394 (8)	N4—H4A	0.8900
C18—C19	1.396 (7)	N6—Hg1^ii	2.265 (4)
C18—H18	0.9300
C6—C1—C2	116.6 (6)	C20—C21—H21	119.5
C6—C1—H1	121.7	C22—C21—H21	119.5
C2—C1—H1	121.7	C17—C22—C21	119.4 (5)
C3—C2—N6	108.9 (5)	C17—C22—H22	120.3
C3—C2—C1	120.8 (5)	C21—C22—H22	120.3
N6—C2—C1	130.3 (5)	N7—C23—C20	113.4 (5)
N5—C3—C2	106.2 (4)	N7—C23—H23A	108.9
N5—C3—C4	132.0 (5)	C20—C23—H23A	108.9
C2—C3—C4	121.7 (6)	N7—C23—H23B	108.9
C5—C4—C3	117.2 (6)	C20—C23—H23B	108.9
C5—C4—H4	121.4	H23A—C23—H23B	107.7
C3—C4—H4	121.4	N8—C24—N7	114.8 (7)
C4—C5—C6	121.6 (6)	N8—C24—H24	122.6
C4—C5—H5	119.2	N7—C24—H24	122.6
C6—C5—H5	119.2	C26—C25—C30	119.0 (8)
C1—C6—C5	122.0 (7)	C26—C25—N8	110.0 (6)
C1—C6—H6	119.0	C30—C25—N8	130.9 (8)
C5—C6—H6	119.0	N7—C26—C25	105.8 (6)
N6—C7—N5	113.5 (5)	N7—C26—C27	130.9 (7)
N6—C7—H7	123.3	C25—C26—C27	123.2 (8)
N5—C7—H7	123.3	C28—C27—C26	115.7 (9)
N5—C8—C9	113.0 (4)	C28—C27—H27	122.2
N5—C8—H8A	109.0	C26—C27—H27	122.2
C9—C8—H8A	109.0	C29—C28—C27	122.3 (10)
N5—C8—H8B	109.0	C29—C28—H28	118.8
C9—C8—H8B	109.0	C27—C28—H28	118.8
H8A—C8—H8B	107.8	C28—C29—C30	120.9 (10)
C10—C9—C14	119.1 (5)	C28—C29—H29	119.6
C10—C9—C8	121.4 (5)	C30—C29—H29	119.6
C14—C9—C8	119.4 (6)	C25—C30—C29	118.8 (9)
C9—C10—C11	120.4 (5)	C25—C30—H30	120.6
C9—C10—H10	119.8	C29—C30—H30	120.6
C11—C10—H10	119.8	Cl4—C31—Cl3	99.5 (6)
C12—C11—C10	120.1 (6)	Cl4—C31—H31A	111.9
C12—C11—H11	120.0	Cl3—C31—H31A	111.9
C10—C11—H11	120.0	Cl4—C31—H31B	111.9
C13—C12—C11	119.1 (5)	Cl3—C31—H31B	111.9
C13—C12—C15	121.1 (5)	H31A—C31—H31B	109.6
C11—C12—C15	119.5 (5)	N6^i—Hg1—N2	95.32 (15)
C14—C13—C12	121.6 (5)	N6^i—Hg1—Cl2	112.97 (12)
C14—C13—H13	119.2	N2—Hg1—Cl2	111.62 (13)
C12—C13—H13	119.2	N6^i—Hg1—Cl1	109.17 (12)
C13—C14—C9	119.7 (6)	N2—Hg1—Cl1	103.99 (11)
C13—C14—H14	120.1	Cl2—Hg1—Cl1	120.51 (7)
C9—C14—H14	120.1	C15—N1—N2	106.1 (4)
N1—C15—N3	110.3 (4)	C16—N2—N1	108.3 (4)
N1—C15—C12	123.7 (5)	C16—N2—Hg1	128.2 (3)
N3—C15—C12	126.0 (5)	N1—N2—Hg1	117.2 (3)
N2—C16—N3	108.9 (4)	C16—N3—C15	106.5 (4)
N2—C16—C17	124.6 (4)	C16—N3—N4	125.0 (4)
N3—C16—C17	126.5 (4)	C15—N3—N4	128.3 (4)
C22—C17—C18	119.8 (5)	N3—N4—H4B	109.2
C22—C17—C16	121.1 (5)	N3—N4—H4A	109.1
C18—C17—C16	119.1 (5)	H4B—N4—H4A	109.5
C17—C18—C19	119.9 (5)	C7—N5—C3	105.9 (4)
C17—C18—H18	120.1	C7—N5—C8	125.9 (5)
C19—C18—H18	120.1	C3—N5—C8	127.8 (5)
C20—C19—C18	120.3 (5)	C7—N6—C2	105.5 (4)
C20—C19—H19	119.9	C7—N6—Hg1^ii	124.8 (3)
C18—C19—H19	119.9	C2—N6—Hg1^ii	129.7 (3)
C21—C20—C19	119.6 (5)	C24—N7—C26	105.4 (6)
C21—C20—C23	122.4 (5)	C24—N7—C23	127.1 (6)
C19—C20—C23	117.9 (5)	C26—N7—C23	127.5 (6)
C20—C21—C22	121.1 (5)	C24—N8—C25	104.0 (6)
C6—C1—C2—C3	1.7 (10)	C26—C25—C30—C29	1.4 (11)
C6—C1—C2—N6	−179.9 (6)	N8—C25—C30—C29	−177.7 (7)
N6—C2—C3—N5	1.4 (6)	C28—C29—C30—C25	−0.5 (13)
C1—C2—C3—N5	−179.9 (5)	N3—C15—N1—N2	0.6 (6)
N6—C2—C3—C4	179.1 (5)	C12—C15—N1—N2	177.3 (5)
C1—C2—C3—C4	−2.2 (9)	N3—C16—N2—N1	−0.9 (6)
N5—C3—C4—C5	178.7 (6)	C17—C16—N2—N1	179.4 (5)
C2—C3—C4—C5	1.6 (9)	N3—C16—N2—Hg1	149.8 (4)
C3—C4—C5—C6	−0.8 (11)	C17—C16—N2—Hg1	−29.9 (8)
C2—C1—C6—C5	−0.9 (11)	C15—N1—N2—C16	0.2 (6)
C4—C5—C6—C1	0.4 (12)	C15—N1—N2—Hg1	−154.2 (4)
N5—C8—C9—C10	67.2 (8)	N6^i—Hg1—N2—C16	−17.7 (5)
N5—C8—C9—C14	−116.4 (6)	Cl2—Hg1—N2—C16	99.6 (5)
C14—C9—C10—C11	−0.9 (9)	Cl1—Hg1—N2—C16	−128.9 (4)
C8—C9—C10—C11	175.5 (5)	N6^i—Hg1—N2—N1	130.9 (3)
C9—C10—C11—C12	0.0 (9)	Cl2—Hg1—N2—N1	−111.9 (3)
C10—C11—C12—C13	0.9 (9)	Cl1—Hg1—N2—N1	19.6 (4)
C10—C11—C12—C15	−172.5 (5)	N2—C16—N3—C15	1.2 (6)
C11—C12—C13—C14	−1.0 (9)	C17—C16—N3—C15	−179.1 (5)
C15—C12—C13—C14	172.3 (5)	N2—C16—N3—N4	175.9 (5)
C12—C13—C14—C9	0.0 (9)	C17—C16—N3—N4	−4.4 (8)
C10—C9—C14—C13	0.9 (9)	N1—C15—N3—C16	−1.1 (6)
C8—C9—C14—C13	−175.6 (5)	C12—C15—N3—C16	−177.8 (5)
C13—C12—C15—N1	−125.5 (6)	N1—C15—N3—N4	−175.5 (5)
C11—C12—C15—N1	47.8 (8)	C12—C15—N3—N4	7.8 (9)
C13—C12—C15—N3	50.8 (8)	N6—C7—N5—C3	1.1 (6)
C11—C12—C15—N3	−136.0 (6)	N6—C7—N5—C8	−171.6 (5)
N2—C16—C17—C22	140.7 (6)	C2—C3—N5—C7	−1.4 (6)
N3—C16—C17—C22	−38.9 (8)	C4—C3—N5—C7	−178.9 (6)
N2—C16—C17—C18	−37.2 (8)	C2—C3—N5—C8	171.0 (5)
N3—C16—C17—C18	143.1 (6)	C4—C3—N5—C8	−6.4 (10)
C22—C17—C18—C19	−1.0 (9)	C9—C8—N5—C7	−124.7 (6)
C16—C17—C18—C19	177.0 (5)	C9—C8—N5—C3	64.2 (8)
C17—C18—C19—C20	1.4 (9)	N5—C7—N6—C2	−0.2 (6)
C18—C19—C20—C21	−0.7 (9)	N5—C7—N6—Hg1^ii	177.1 (3)
C18—C19—C20—C23	−179.9 (6)	C3—C2—N6—C7	−0.7 (6)
C19—C20—C21—C22	−0.4 (9)	C1—C2—N6—C7	−179.3 (6)
C23—C20—C21—C22	178.8 (6)	C3—C2—N6—Hg1^ii	−177.9 (4)
C18—C17—C22—C21	−0.1 (8)	C1—C2—N6—Hg1^ii	3.6 (9)
C16—C17—C22—C21	−178.0 (5)	N8—C24—N7—C26	0.4 (7)
C20—C21—C22—C17	0.8 (9)	N8—C24—N7—C23	178.7 (5)
C21—C20—C23—N7	11.6 (9)	C25—C26—N7—C24	−0.9 (6)
C19—C20—C23—N7	−169.2 (6)	C27—C26—N7—C24	−176.9 (6)
C30—C25—C26—N7	−178.1 (6)	C25—C26—N7—C23	−179.2 (5)
N8—C25—C26—N7	1.1 (6)	C27—C26—N7—C23	4.9 (9)
C30—C25—C26—C27	−1.8 (9)	C20—C23—N7—C24	−93.4 (7)
N8—C25—C26—C27	177.5 (6)	C20—C23—N7—C26	84.6 (7)
N7—C26—C27—C28	176.6 (7)	N7—C24—N8—C25	0.3 (7)
C25—C26—C27—C28	1.3 (10)	C26—C25—N8—C24	−0.9 (7)
C26—C27—C28—C29	−0.4 (13)	C30—C25—N8—C24	178.3 (7)
C27—C28—C29—C30	0.0 (15)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···N8^ii	0.89	2.09	2.940 (8)	160
N4—H4A···Cl2^iii	0.89	2.98	3.473 (5)	117

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