Di-μ-chlorido-bis­{[4-amino-3,5-bis­(2-pyrid­yl)-4H-1,2,4-triazole-κN1]chloridomercury(II)}

Guo, J.; Tang, M.; Chen, J.; Li, C.-P.

doi:10.1107/S1600536811029886

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1180

doi:10.1107/S1600536811029886

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Di-μ-chlorido-bis{[4-amino-3,5-bis(2-pyridyl)-4H-1,2,4-triazole-κN¹]chloridomercury(II)}

Jian Guo,^a Min Tang,^a Jing Chen ^a and Cheng-Peng Li ^a ^*

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance of Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: tjnulicp@gmail.com

(Received 12 July 2011; accepted 24 July 2011; online 2 August 2011)

In the centrosymmetric binuclear title complex, [Hg₂Cl₄(C₁₂H₁₀N₆)₂], the Hg^II ion is five-coordinated by two N atoms and three chloride ions with a distorted square-pyramidal geometry. In the complex, there is an intramolecular N—H⋯N hydrogen bond. In the crystal, the binuclear units are connected by intermolecular N—H⋯Cl hydrogen bonds, as well as π–π stacking interactions [centroid–centroid distances = 3.526 (2) and 3.696 (2) Å], forming a two-dimensional layered structure parallel to (010).

Related literature

For background information on triazole derivatives, see: Klingele et al. (2009 ); Shao et al. (2004 ); Huang et al. (2011 ). For the coordination compounds synthesized with related triazole ligands, see: Du et al. (2007 , 2008 ). For a description of the geometry of complexes with five-coordinate metal ions, see: Addison et al. (1984 ).

Experimental

Crystal data

[Hg₂Cl₄(C₁₂H₁₀N₆)₂]
M_r = 1019.50
Orthorhombic, P b c a
a = 11.3634 (4) Å
b = 14.9962 (6) Å
c = 17.2328 (7) Å
V = 2936.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 10.85 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.475, T_max = 1.000
14063 measured reflections
2596 independent reflections
2071 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.058
S = 1.08
2596 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯Cl2ⁱ	0.89	2.80	3.446 (3)	131
N5—H5A⋯Cl1ⁱⁱ	0.89	2.77	3.512 (4)	142
N5—H5B⋯Cl1ⁱⁱⁱ	0.89	2.62	3.452 (4)	155
N5—H5B⋯N6	0.89	2.47	2.956 (5)	115
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029886/su2294sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029886/su2294Isup2.hkl

checkCIF report

Comment top

1,2,4-triazole and its derivatives have been extensively used to prepare diverse coordination complexes (Klingele et al., 2009; Shao et al., 2004; Huang et al., 2011). Recently, a series of interesting metallosupramolecular systems have been constructed using the triazole ligands 4-amino-3,5-bis(4-pyridyl)-1,2,4-triazole and 4-amino-3,5-bis(3-pyridyl)-1,2,4-triazole, using different synthetic methods (Du et al., 2007, 2008). In this context, the analogous ligand, 4-amino-3,5-bis(2-pyridyl)-1,2,4-triazole (2-bpt), that may exhibit different conformations and coordination modes, has received our attention.

Herein, we present the title binuclear complex obtained by the reaction of 2-bpt and HgCl₂ under the hydrothermal condition. In the centrosymmetric title complex, the coordination sphere of each Hg^II ion can be described as a distorted square pyramid, as indicated by the τ value of 0.33 (Addison et al., 1984). The Hg^II ion coordinates to one terminal chloride ion, two bridging chloride ions and two chelating nitrogen donors from the same 2-bpt ligand (Fig. 1). Each 2-bpt ligand adopts the anti-conformation considering its two terminal pyridyl nitrogen, with the bidentate chelating coordination to one Hg^II center. In addition, the two adjacent Hg^II centers are linked by a pair of chloride bridges to form a Hg₂Cl₂ subunit, in which the Hg···Hg separation is 3.856 (1) Å and the Hg–Cl–Hg angle is 93.22 (3)°. There is an intramolecular N5–H5B···N6 hydrogen bond in the complex (Table 1).

In the crystal the binuclear units are connected to form a two-dimensional supramolecular network via intermolecular N-H···Cl hydrogen bonds (Table 1 and Fig. 2). In addition, π–π stacking interactions are present and further reinforce the two-dimensional supramolecular network. The centroid-centroid distance of the involved pyridyl rings, (N1/C1—C5) and (N6/C8—C12)ⁱ, is 3.696 (2) Å, while the centroid-centroid distance involving the triazole rings, (N2—N4/C6,C7) and (N2—N4/C6,C7)ⁱ, is 3.526 (2) Å (Fig. 2; symmetry code: (i) = -x+2, -y+1, -z+2).

Related literature top

For background information on triazole derivatives, see: Klingele et al. (2009); Shao et al. (2004); Huang et al. (2011). For the coordination compounds synthesized with related triazole ligands, see: Du et al. (2007, 2008). For a description of five-coordinate metal geometries, see: Addison et al. (1984).

Experimental top

A mixture of 2-bpt (23.8 mg, 0.1 mmol), HgCl₂ (27.1 mg, 0.1 mmol) in water (10 ml) was sealed in a Teflon-lined stainless steel vessel (20 ml), which was heated to 413 K over a period of 24 h. It was then gradually cooled to room temperature at a rate of 5 °C/h. Colourless block-like crystals, suitable for X-ray analysis, were obtained. Anal. Calc. for C₂₄H₂₀Cl₄Hg₂N₁₂: C, 28.27; H, 1.98; N, 16.49%. Found: C, 28.30; H, 1.94; N, 16.47%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view along the c-axis of the two-dimensional network in the crystal of the title compound, showing the N–H···N and N–H···Cl hydrogen bonds (red dashed lines) and the π–π stacking interactions (green dashed lines) [See Table 1 and the comment section for details].

Di-µ-chlorido-bis{[4-amino-3,5-bis(2-pyridyl)-4H-1,2,4- triazole-κN¹]chloridomercury(II)} top

Crystal data top

[Hg₂Cl₄(C₁₂H₁₀N₆)₂]	F(000) = 1904
M_r = 1019.50	D_x = 2.306 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5032 reflections
a = 11.3634 (4) Å	θ = 2.5–28.1°
b = 14.9962 (6) Å	µ = 10.85 mm⁻¹
c = 17.2328 (7) Å	T = 296 K
V = 2936.6 (2) Å³	Block, colourless
Z = 4	0.28 × 0.22 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2596 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→13
T_min = 0.475, T_max = 1.000	k = −16→17
14063 measured reflections	l = −20→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.028P)² + 2.8778P] where P = (F_o² + 2F_c²)/3
2596 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

[Hg₂Cl₄(C₁₂H₁₀N₆)₂]	V = 2936.6 (2) Å³
M_r = 1019.50	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 11.3634 (4) Å	µ = 10.85 mm⁻¹
b = 14.9962 (6) Å	T = 296 K
c = 17.2328 (7) Å	0.28 × 0.22 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2596 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2071 reflections with I > 2σ(I)
T_min = 0.475, T_max = 1.000	R_int = 0.023
14063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.08	Δρ_max = 0.53 e Å⁻³
2596 reflections	Δρ_min = −1.26 e Å⁻³
190 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Hg1	0.661120 (15)	0.459756 (11)	0.997612 (9)	0.04268 (8)
Cl1	0.66817 (10)	0.31955 (7)	0.92929 (6)	0.0460 (3)
Cl2	0.53708 (10)	0.57586 (7)	0.92105 (6)	0.0486 (3)
N1	0.7468 (3)	0.5214 (2)	1.11219 (19)	0.0384 (8)
N2	0.8392 (3)	0.5359 (2)	0.9665 (2)	0.0381 (9)
N3	0.8938 (3)	0.5633 (2)	0.89923 (19)	0.0377 (8)
N4	0.9726 (3)	0.63366 (19)	0.99779 (15)	0.0266 (7)
N5	1.0319 (3)	0.6981 (2)	1.04316 (18)	0.0356 (8)
H5A	1.0021	0.7495	1.0264	0.053*
H5B	1.1086	0.6932	1.0335	0.053*
N6	1.1599 (3)	0.6863 (2)	0.89418 (19)	0.0413 (9)
C1	0.9194 (4)	0.5833 (3)	1.1697 (2)	0.0377 (10)
H1	0.9916	0.6116	1.1636	0.045*
C2	0.8783 (5)	0.5612 (3)	1.2427 (2)	0.0489 (12)
H2	0.9231	0.5735	1.2866	0.059*
C3	0.7707 (5)	0.5210 (3)	1.2493 (3)	0.0554 (13)
H3	0.7406	0.5068	1.2980	0.066*
C4	0.7081 (4)	0.5017 (3)	1.1836 (3)	0.0504 (12)
H4	0.6354	0.4738	1.1888	0.060*
C5	0.8509 (4)	0.5626 (3)	1.1058 (2)	0.0326 (9)
C6	0.8872 (4)	0.5792 (3)	1.0255 (2)	0.0292 (8)
C7	0.9726 (3)	0.6220 (2)	0.9190 (2)	0.0286 (8)
C8	1.0551 (3)	0.6651 (2)	0.8653 (2)	0.0300 (9)
C9	1.0248 (4)	0.6771 (3)	0.7884 (2)	0.0438 (10)
H9	0.9512	0.6599	0.7702	0.053*
C10	1.1062 (5)	0.7153 (3)	0.7393 (2)	0.0506 (13)
H10	1.0883	0.7250	0.6873	0.061*
C11	1.2143 (5)	0.7389 (3)	0.7688 (3)	0.0536 (13)
H11	1.2710	0.7650	0.7371	0.064*
C12	1.2368 (4)	0.7232 (3)	0.8453 (3)	0.0515 (12)
H12	1.3102	0.7392	0.8646	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.04114 (12)	0.03899 (12)	0.04791 (13)	−0.00931 (7)	0.00559 (8)	−0.00763 (7)
Cl1	0.0512 (7)	0.0409 (6)	0.0458 (6)	−0.0077 (5)	0.0005 (5)	−0.0119 (5)
Cl2	0.0474 (7)	0.0458 (6)	0.0524 (7)	0.0020 (5)	0.0129 (5)	0.0116 (5)
N1	0.038 (2)	0.0356 (19)	0.0413 (19)	−0.0031 (16)	0.0071 (16)	0.0029 (15)
N2	0.039 (2)	0.039 (2)	0.0355 (19)	−0.0087 (17)	0.0010 (16)	−0.0032 (16)
N3	0.041 (2)	0.040 (2)	0.0321 (18)	−0.0088 (17)	0.0007 (16)	−0.0049 (15)
N4	0.0283 (17)	0.0246 (16)	0.0271 (16)	−0.0013 (13)	−0.0005 (14)	−0.0011 (13)
N5	0.042 (2)	0.0365 (19)	0.0283 (17)	−0.0086 (16)	−0.0004 (16)	−0.0082 (14)
N6	0.042 (2)	0.048 (2)	0.0347 (18)	−0.0137 (17)	0.0009 (16)	0.0035 (16)
C1	0.043 (3)	0.037 (2)	0.033 (2)	0.0008 (19)	0.0031 (19)	0.0026 (18)
C2	0.063 (3)	0.049 (3)	0.035 (2)	0.005 (3)	0.004 (2)	0.004 (2)
C3	0.073 (4)	0.053 (3)	0.040 (3)	0.002 (3)	0.021 (3)	0.008 (2)
C4	0.051 (3)	0.047 (3)	0.054 (3)	−0.007 (2)	0.017 (2)	0.009 (2)
C5	0.036 (2)	0.024 (2)	0.038 (2)	0.0060 (18)	0.0041 (18)	0.0025 (17)
C6	0.030 (2)	0.025 (2)	0.0319 (19)	0.0008 (17)	0.0031 (17)	−0.0020 (16)
C7	0.033 (2)	0.0270 (19)	0.0261 (18)	0.0032 (17)	−0.0026 (17)	−0.0008 (15)
C8	0.037 (2)	0.028 (2)	0.0251 (19)	0.0000 (18)	0.0040 (17)	−0.0004 (15)
C9	0.052 (3)	0.047 (3)	0.032 (2)	−0.002 (2)	−0.007 (2)	−0.0006 (18)
C10	0.085 (4)	0.041 (2)	0.026 (2)	0.003 (3)	0.007 (2)	0.0065 (18)
C11	0.072 (4)	0.045 (3)	0.044 (3)	−0.011 (3)	0.017 (3)	0.004 (2)
C12	0.050 (3)	0.051 (3)	0.054 (3)	−0.018 (2)	0.005 (2)	0.002 (2)

Geometric parameters (Å, º) top

Hg1—N2	2.385 (3)	C1—C2	1.383 (6)
Hg1—N1	2.388 (3)	C1—C5	1.384 (6)
Hg1—Cl1	2.4111 (10)	C1—H1	0.9300
Hg1—Cl2	2.5998 (11)	C2—C3	1.368 (7)
Hg1—Cl2ⁱ	2.7061 (11)	C2—H2	0.9300
Cl2—Hg1ⁱ	2.7061 (11)	C3—C4	1.368 (7)
N1—C5	1.339 (5)	C3—H3	0.9300
N1—C4	1.340 (5)	C4—H4	0.9300
N2—C6	1.324 (5)	C5—C6	1.465 (5)
N2—N3	1.378 (5)	C7—C8	1.468 (5)
N3—C7	1.301 (5)	C8—C9	1.380 (5)
N4—C6	1.355 (5)	C9—C10	1.378 (6)
N4—C7	1.368 (4)	C9—H9	0.9300
N4—N5	1.414 (4)	C10—C11	1.376 (8)
N5—H5A	0.8901	C10—H10	0.9300
N5—H5B	0.8900	C11—C12	1.365 (6)
N6—C8	1.329 (5)	C11—H11	0.9300
N6—C12	1.333 (5)	C12—H12	0.9300

N2—Hg1—N1	69.78 (12)	C2—C3—C4	119.3 (4)
N2—Hg1—Cl1	106.24 (9)	C2—C3—H3	120.4
N1—Hg1—Cl1	136.70 (9)	C4—C3—H3	120.4
N2—Hg1—Cl2	91.45 (9)	N1—C4—C3	122.9 (5)
N1—Hg1—Cl2	112.43 (8)	N1—C4—H4	118.6
Cl1—Hg1—Cl2	110.74 (4)	C3—C4—H4	118.6
N2—Hg1—Cl2ⁱ	156.52 (9)	N1—C5—C1	122.3 (4)
N1—Hg1—Cl2ⁱ	89.27 (8)	N1—C5—C6	113.9 (4)
Cl1—Hg1—Cl2ⁱ	96.23 (4)	C1—C5—C6	123.7 (4)
Cl2—Hg1—Cl2ⁱ	86.78 (3)	N2—C6—N4	108.6 (3)
Hg1—Cl2—Hg1ⁱ	93.22 (3)	N2—C6—C5	121.7 (4)
C5—N1—C4	117.9 (4)	N4—C6—C5	129.6 (4)
C5—N1—Hg1	118.1 (3)	N3—C7—N4	110.3 (3)
C4—N1—Hg1	122.7 (3)	N3—C7—C8	124.9 (3)
C6—N2—N3	108.4 (3)	N4—C7—C8	124.8 (3)
C6—N2—Hg1	114.3 (3)	N6—C8—C9	123.5 (4)
N3—N2—Hg1	135.5 (3)	N6—C8—C7	116.2 (3)
C7—N3—N2	106.9 (3)	C9—C8—C7	120.2 (4)
C6—N4—C7	105.9 (3)	C10—C9—C8	118.4 (4)
C6—N4—N5	123.9 (3)	C10—C9—H9	120.8
C7—N4—N5	129.4 (3)	C8—C9—H9	120.8
N4—N5—H5A	103.4	C11—C10—C9	118.7 (4)
N4—N5—H5B	107.9	C11—C10—H10	120.6
H5A—N5—H5B	112.5	C9—C10—H10	120.6
C8—N6—C12	116.7 (4)	C12—C11—C10	118.6 (4)
C2—C1—C5	118.7 (4)	C12—C11—H11	120.7
C2—C1—H1	120.6	C10—C11—H11	120.7
C5—C1—H1	120.6	N6—C12—C11	124.1 (5)
C3—C2—C1	118.9 (4)	N6—C12—H12	118.0
C3—C2—H2	120.6	C11—C12—H12	118.0
C1—C2—H2	120.6

N2—Hg1—Cl2—Hg1ⁱ	−156.57 (9)	C2—C1—C5—C6	−177.3 (4)
N1—Hg1—Cl2—Hg1ⁱ	−87.88 (9)	N3—N2—C6—N4	−0.5 (4)
Cl1—Hg1—Cl2—Hg1ⁱ	95.44 (4)	Hg1—N2—C6—N4	−167.7 (2)
Cl2ⁱ—Hg1—Cl2—Hg1ⁱ	0.0	N3—N2—C6—C5	−177.9 (4)
N2—Hg1—N1—C5	−3.4 (3)	Hg1—N2—C6—C5	14.9 (5)
Cl1—Hg1—N1—C5	89.1 (3)	C7—N4—C6—N2	0.9 (4)
Cl2—Hg1—N1—C5	−86.3 (3)	N5—N4—C6—N2	171.6 (3)
Cl2ⁱ—Hg1—N1—C5	−172.6 (3)	C7—N4—C6—C5	178.0 (4)
N2—Hg1—N1—C4	−169.9 (4)	N5—N4—C6—C5	−11.2 (6)
Cl1—Hg1—N1—C4	−77.4 (4)	N1—C5—C6—N2	−17.9 (5)
Cl2—Hg1—N1—C4	107.1 (3)	C1—C5—C6—N2	159.1 (4)
Cl2ⁱ—Hg1—N1—C4	20.9 (3)	N1—C5—C6—N4	165.3 (4)
N1—Hg1—N2—C6	−5.9 (3)	C1—C5—C6—N4	−17.8 (7)
Cl1—Hg1—N2—C6	−140.4 (3)	N2—N3—C7—N4	0.6 (4)
Cl2—Hg1—N2—C6	107.5 (3)	N2—N3—C7—C8	176.7 (3)
Cl2ⁱ—Hg1—N2—C6	22.2 (4)	C6—N4—C7—N3	−0.9 (4)
N1—Hg1—N2—N3	−168.5 (4)	N5—N4—C7—N3	−171.0 (4)
Cl1—Hg1—N2—N3	57.0 (4)	C6—N4—C7—C8	−177.0 (3)
Cl2—Hg1—N2—N3	−55.1 (4)	N5—N4—C7—C8	12.9 (6)
Cl2ⁱ—Hg1—N2—N3	−140.3 (3)	C12—N6—C8—C9	1.8 (6)
C6—N2—N3—C7	−0.1 (4)	C12—N6—C8—C7	178.2 (4)
Hg1—N2—N3—C7	163.2 (3)	N3—C7—C8—N6	−148.0 (4)
C5—C1—C2—C3	−1.0 (6)	N4—C7—C8—N6	27.6 (5)
C1—C2—C3—C4	1.6 (7)	N3—C7—C8—C9	28.6 (6)
C5—N1—C4—C3	−0.9 (7)	N4—C7—C8—C9	−155.9 (4)
Hg1—N1—C4—C3	165.7 (4)	N6—C8—C9—C10	−1.8 (6)
C2—C3—C4—N1	−0.6 (7)	C7—C8—C9—C10	−178.1 (4)
C4—N1—C5—C1	1.5 (6)	C8—C9—C10—C11	0.7 (7)
Hg1—N1—C5—C1	−165.7 (3)	C9—C10—C11—C12	0.2 (7)
C4—N1—C5—C6	178.5 (4)	C8—N6—C12—C11	−0.8 (7)
Hg1—N1—C5—C6	11.3 (4)	C10—C11—C12—N6	−0.2 (7)
C2—C1—C5—N1	−0.5 (6)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···Cl2ⁱⁱ	0.89	2.80	3.446 (3)	131
N5—H5A···Cl1ⁱⁱⁱ	0.89	2.77	3.512 (4)	142
N5—H5B···Cl1^iv	0.89	2.62	3.452 (4)	155
N5—H5B···N6	0.89	2.47	2.956 (5)	115

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

Experimental details

Crystal data
Chemical formula	[Hg₂Cl₄(C₁₂H₁₀N₆)₂]
M_r	1019.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.3634 (4), 14.9962 (6), 17.2328 (7)
V (Å³)	2936.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.85
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.475, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14063, 2596, 2071
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.058, 1.08
No. of reflections	2596
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −1.26

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···Cl2ⁱ	0.89	2.80	3.446 (3)	131
N5—H5A···Cl1ⁱⁱ	0.89	2.77	3.512 (4)	142
N5—H5B···Cl1ⁱⁱⁱ	0.89	2.62	3.452 (4)	155
N5—H5B···N6	0.89	2.47	2.956 (5)	115

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

Acknowledgements

This work was financially supported by Tianjin Normal University (grant No. 52X09004).

References

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