[μ-1,1′-(Butane-1,4-di­yl)di-1H-benz­imidazole-κ2N3:N3′]bis­{[N,N′-bis(car­boxy­meth­yl)ethyl­enediamine-N,N′-di­acetato-κ5O,O′,O′′,N,N′]mercury(II)} methanol disolvate

Zhu, X.-W.; Xiao, B.; Yin, Z.-G.; Qian, H.-Y.; Li, G.-S.

doi:10.1107/S1600536809026221

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m912

doi:10.1107/S1600536809026221

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[μ-1,1′-(Butane-1,4-diyl)di-1H-benzimidazole-κ²N³:N^3′]bis{[N,N′-bis(carboxymethyl)ethylenediamine-N,N′-diacetato-κ⁵O,O′,O′′,N,N′]mercury(II)} methanol disolvate

Xue-Wen Zhu,^a ^* Bo Xiao,^a Zhi-Gang Yin,^a Heng-Yu Qian ^a and Gang-Sen Li ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: zhuxuew@126.com

(Received 24 May 2009; accepted 6 July 2009; online 11 July 2009)

The binuclear title complex, [Hg₂(C₁₀H₁₄N₂O₈)₂(C₁₈H₁₈N₄)]·2CH₃OH, lies on an inversion center with the unique Hg^II ion coordinated in a disorted octahedral environment with one Hg—N bond significantly shorter than the other two. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link complex and solvent molecules into a three-dimensional network.

Related literature

For the synthesis, see: Xiao et al. (2004 ); Xie et al. (2002 ). For bond lengths related mercury compounds, see: Guo & Dong (2009 ); Aghabozorg, et al. (2008 ).

Experimental

Crystal data

[Hg₂(C₁₀H₁₄N₂O₈)₂(C₁₈H₁₈N₄)]·2CH₄O
M_r = 1336.09
Monoclinic, P 2₁ /n
a = 10.274 (2) Å
b = 19.990 (3) Å
c = 11.4717 (17) Å
β = 104.035 (13)°
V = 2285.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 6.79 mm⁻¹
T = 291 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.21, T_max = 0.29
14826 measured reflections
4397 independent reflections
3744 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 1.04
4397 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −1.60 e Å⁻³

Table 1
Selected bond lengths (Å)

Hg1—N1	2.138 (6)
Hg1—N4	2.364 (6)
Hg1—N3	2.390 (6)
Hg1—O3	2.473 (5)
Hg1—O5	2.547 (5)
Hg1—O1	2.604 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.82	1.74	2.534 (7)	164
O8—H8⋯O4ⁱⁱ	0.82	1.84	2.462 (7)	131
O9—H9⋯O6ⁱⁱⁱ	0.82	2.00	2.744 (7)	150
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x, -y, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026221/lh2830sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026221/lh2830Isup2.hkl

checkCIF report

Comment top

Research of transition metal-organic polymers has been rapidly expanding because of their intriguing topologies and potential applications in catalysis, fluorescence, electrical conductivity and magnetism. As a result, the preparation of coordination polymers with fascinating frameworks has attracted considerable attention in recent years. For our group, metal-organic nonlinear optical (NLO) materials are of interest for various applications such as optical data processing and biological imaging (Xiao et al., 2004). Some mercury complexes have already been synthesised (Guo, et al., 2009; Aghabozorg et al., 2008), and herein we present the synthesis and crystal structure of the title complex (I) using EDTA and bbbm (Xie, et al., 2002) as ligands. The molecular structure of the title complex is shown in Fig. 1. The dinuclear complex lies on an inversion center with the unique Hg^II ion coordinated in a disorted octahedral coordination environment with one Hg—N bond significantly shorter than the other two, most likely, in part, as a results of steric effects from the bulky ligands. The Hg-O bond lengths are in agreement with those found in related Hg(II) complexes (Guo & Dong, 2009; Aghabozorg, et al., 2008). The intramolecular Hg···Hg distance is ca. 12.21Å. In the crystal structure, intermolecular O-H···O hydrogen bonds link complex and solvent molecules into a three-dimensional network (Fig. 2). In addition there are weak π···π stacking interactions between benzimidazole rings related by inversion symmetry with a centroid to centroid distance of 3.556 (4)Å.

Related literature top

For the synthesis, see: Bo Xiao et al. (2004); Xie et al. (2002). For bond lengths related mercury compounds, see: Guo & Dong (2009); Aghabozorg, et al. (2008).

Experimental top

Methanol solutions of HgCl₂.2H₂O (76 mg, 0.2 mmol), Na₂edta (67 mg, 0.2 mmol) and 1, 1'-(1,4-butylidene)bis-1H-benzimidazole (15 mg, 0.1 mmol) were mixed in a 2:2:1 molar ratio, and the reaction mixture was stirred at about 300 K for 2 h. Colourless crystals ofthe title compound were obtained from the solution after three weeks at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure with ellipsoids shown at the 30% level. Symmetry code: (A) 1-x, 2-y, -z. The symmetry related solvent methanol molecule is not shown.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. Only H atoms included in the hydrogen bonds have been included.

[µ-1,1'-(Butane-1,4-diyl)di-1H-benzimidazole-κ²N³: N^3']bis{[N,N'-bis(carboxymethyl)ethylenediamine- N,N'-diacetato-κ⁵O,O',O'',N, N']mercury(II)} methanol disolvate top

Crystal data top

[Hg₂(C₁₀H₁₄N₂O₈)₂(C₁₈H₁₈N₄)]·2CH₄O	F(000) = 1308
M_r = 1336.09	D_x = 1.941 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2608 reflections
a = 10.274 (2) Å	θ = 2.4–25.3°
b = 19.990 (3) Å	µ = 6.79 mm⁻¹
c = 11.4717 (17) Å	T = 291 K
β = 104.035 (13)°	Prism, colorless
V = 2285.7 (7) Å³	0.24 × 0.20 × 0.18 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	4397 independent reflections
Radiation source: sealed tube	3744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.21, T_max = 0.29	k = −23→24
14826 measured reflections	l = −14→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.08P)² + 1.99P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4397 reflections	Δρ_max = 1.08 e Å⁻³
310 parameters	Δρ_min = −1.60 e Å⁻³
0 restraints	Absolute structure: Refinement
Primary atom site location: structure-invariant direct methods

Crystal data top

[Hg₂(C₁₀H₁₄N₂O₈)₂(C₁₈H₁₈N₄)]·2CH₄O	V = 2285.7 (7) Å³
M_r = 1336.09	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.274 (2) Å	µ = 6.79 mm⁻¹
b = 19.990 (3) Å	T = 291 K
c = 11.4717 (17) Å	0.24 × 0.20 × 0.18 mm
β = 104.035 (13)°

Data collection top

Bruker SMART APEX diffractometer	4397 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3744 reflections with I > 2σ(I)
T_min = 0.21, T_max = 0.29	R_int = 0.062
14826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	Δρ_max = 1.08 e Å⁻³
4397 reflections	Δρ_min = −1.60 e Å⁻³
310 parameters	Absolute structure: Refinement

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
C1	0.1031 (7)	0.0816 (3)	1.0464 (6)	0.0335 (15)
C2	0.0283 (8)	0.1117 (4)	1.1206 (6)	0.0395 (17)
H2A	−0.0216	0.1506	1.0997	0.047*
C3	0.0363 (8)	0.0778 (4)	1.2276 (7)	0.0421 (17)
H3	−0.0152	0.0924	1.2791	0.051*
C4	0.1222 (7)	0.0205 (4)	1.2612 (6)	0.0357 (15)
H4	0.1289	0.0008	1.3359	0.043*
C5	0.1937 (7)	−0.0058 (4)	1.1866 (6)	0.0370 (16)
H5	0.2490	−0.0428	1.2085	0.044*
C6	0.1803 (7)	0.0253 (4)	1.0767 (7)	0.0379 (16)
C7	0.1798 (7)	0.0552 (4)	0.8889 (7)	0.0419 (17)
H7	0.1937	0.0537	0.8118	0.050*
C8	0.3271 (7)	−0.0452 (4)	0.9728 (7)	0.0393 (16)
H8A	0.3203	−0.0567	0.8894	0.047*
H8B	0.3010	−0.0842	1.0121	0.047*
C9	0.4721 (7)	−0.0270 (4)	1.0330 (7)	0.0414 (18)
H9A	0.4770	−0.0121	1.1144	0.050*
H9B	0.5275	−0.0667	1.0376	0.050*
C10	0.0718 (8)	0.3206 (4)	0.9820 (7)	0.0406 (17)
C11	−0.0801 (8)	0.3230 (3)	0.9266 (7)	0.0349 (16)
H11A	−0.1279	0.3025	0.9806	0.042*
H11B	−0.1098	0.3690	0.9130	0.042*
C12	−0.2518 (7)	0.2659 (4)	0.7742 (7)	0.0370 (15)
H12A	−0.2759	0.2549	0.6893	0.044*
H12B	−0.3076	0.3029	0.7873	0.044*
C13	−0.2778 (7)	0.2037 (4)	0.8490 (6)	0.0321 (15)
C14	−0.0796 (8)	0.3303 (3)	0.7160 (6)	0.0348 (15)
H14A	0.0002	0.3564	0.7497	0.042*
H14B	−0.1539	0.3611	0.6894	0.042*
C15	−0.0589 (8)	0.2912 (4)	0.6100 (7)	0.0385 (16)
H15A	−0.1428	0.2700	0.5699	0.046*
H15B	−0.0341	0.3218	0.5534	0.046*
C16	0.0334 (8)	0.1861 (3)	0.5512 (7)	0.0356 (15)
H16A	0.0232	0.2068	0.4731	0.043*
H16B	0.1149	0.1595	0.5675	0.043*
C17	−0.0798 (7)	0.1425 (3)	0.5481 (6)	0.0313 (14)
C18	0.1874 (7)	0.2721 (4)	0.6685 (7)	0.0415 (17)
H18A	0.2052	0.2850	0.5923	0.050*
H18B	0.1872	0.3124	0.7154	0.050*
C19	0.2947 (7)	0.2284 (4)	0.7319 (7)	0.0363 (15)
H20A	0.2877	0.0381	0.5581	0.055*
H20B	0.4119	0.0503	0.6662	0.055*
H20C	0.4187	−0.0043	0.5697	0.055*
C20	0.3614 (9)	0.0155 (4)	0.6152 (7)	0.0436 (18)
Hg1	0.02119 (3)	0.185765 (13)	0.82144 (2)	0.03426 (13)
N1	0.1043 (6)	0.1013 (3)	0.9279 (6)	0.0395 (14)
N2	0.2331 (6)	0.0113 (3)	0.9788 (6)	0.0385 (14)
N3	−0.1082 (6)	0.2859 (3)	0.8103 (6)	0.0375 (13)
N4	0.0466 (6)	0.2392 (3)	0.6444 (5)	0.0366 (13)
O1	0.1436 (5)	0.2817 (3)	0.9589 (5)	0.0465 (13)
O2	0.1103 (5)	0.3704 (3)	1.0576 (5)	0.0414 (12)
H2	0.1924	0.3733	1.0740	0.050*
O3	−0.1763 (5)	0.1700 (3)	0.9062 (5)	0.0412 (13)
O4	−0.3977 (6)	0.1878 (3)	0.8430 (5)	0.0443 (13)
O5	−0.1373 (5)	0.1400 (3)	0.6322 (5)	0.0380 (11)
O6	−0.1182 (6)	0.1106 (3)	0.4498 (5)	0.0502 (15)
O7	0.2823 (6)	0.1763 (3)	0.7841 (6)	0.0443 (13)
O8	0.4098 (5)	0.2491 (3)	0.7194 (5)	0.0401 (12)
H8	0.4604	0.2171	0.7225	0.048*
O9	0.3170 (5)	−0.0289 (3)	0.6776 (5)	0.0415 (12)
H9	0.2418	−0.0408	0.6411	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.040 (4)	0.027 (3)	0.029 (3)	−0.005 (3)	0.000 (3)	−0.007 (3)
C2	0.041 (4)	0.040 (4)	0.031 (4)	0.001 (3)	−0.004 (3)	−0.002 (3)
C3	0.041 (4)	0.042 (4)	0.046 (4)	0.004 (3)	0.015 (3)	0.010 (3)
C4	0.029 (3)	0.042 (4)	0.034 (4)	0.000 (3)	0.001 (3)	0.007 (3)
C5	0.042 (4)	0.032 (4)	0.033 (4)	0.004 (3)	0.000 (3)	0.001 (3)
C6	0.027 (3)	0.039 (4)	0.044 (4)	0.005 (3)	0.001 (3)	0.008 (3)
C7	0.038 (4)	0.040 (4)	0.046 (4)	0.010 (3)	0.007 (3)	0.006 (3)
C8	0.034 (4)	0.044 (4)	0.042 (4)	−0.005 (3)	0.014 (3)	−0.002 (3)
C9	0.032 (4)	0.046 (4)	0.050 (5)	−0.005 (3)	0.016 (3)	−0.013 (4)
C10	0.038 (4)	0.051 (5)	0.035 (4)	0.007 (3)	0.013 (3)	0.007 (3)
C11	0.039 (4)	0.030 (3)	0.038 (4)	−0.005 (3)	0.014 (3)	0.009 (3)
C12	0.040 (4)	0.036 (4)	0.037 (4)	0.011 (3)	0.013 (3)	0.009 (3)
C13	0.034 (4)	0.038 (4)	0.026 (3)	0.011 (3)	0.011 (3)	0.003 (3)
C14	0.037 (4)	0.030 (3)	0.031 (4)	−0.004 (3)	−0.005 (3)	0.000 (3)
C15	0.045 (4)	0.043 (4)	0.030 (4)	0.003 (3)	0.015 (3)	0.004 (3)
C16	0.036 (4)	0.035 (4)	0.038 (4)	−0.008 (3)	0.013 (3)	−0.002 (3)
C17	0.031 (3)	0.020 (3)	0.040 (4)	0.003 (3)	0.004 (3)	0.002 (3)
C18	0.041 (4)	0.036 (4)	0.047 (4)	−0.012 (3)	0.011 (3)	0.002 (3)
C19	0.031 (3)	0.038 (4)	0.045 (4)	−0.005 (3)	0.018 (3)	0.005 (3)
C20	0.062 (5)	0.029 (3)	0.037 (4)	−0.011 (3)	0.008 (4)	−0.001 (3)
Hg1	0.02994 (18)	0.03898 (19)	0.03433 (18)	0.00717 (11)	0.00868 (11)	0.00914 (11)
N1	0.033 (3)	0.047 (4)	0.035 (3)	0.010 (3)	0.001 (3)	0.010 (3)
N2	0.035 (3)	0.045 (3)	0.034 (3)	−0.004 (3)	0.005 (3)	0.004 (3)
N3	0.044 (3)	0.037 (3)	0.034 (3)	0.006 (3)	0.014 (3)	0.003 (3)
N4	0.032 (3)	0.045 (3)	0.032 (3)	−0.007 (3)	0.007 (2)	0.000 (3)
O1	0.036 (3)	0.061 (4)	0.039 (3)	0.005 (3)	0.001 (2)	−0.007 (3)
O2	0.028 (3)	0.053 (3)	0.049 (3)	−0.004 (2)	0.020 (2)	−0.002 (3)
O3	0.042 (3)	0.044 (3)	0.041 (3)	0.012 (2)	0.017 (2)	0.024 (2)
O4	0.033 (3)	0.057 (4)	0.042 (3)	0.002 (2)	0.008 (2)	0.015 (2)
O5	0.031 (2)	0.044 (3)	0.038 (3)	0.002 (2)	0.006 (2)	0.008 (2)
O6	0.050 (3)	0.056 (3)	0.050 (3)	−0.030 (3)	0.023 (3)	−0.018 (3)
O7	0.039 (3)	0.036 (3)	0.056 (4)	−0.012 (2)	0.009 (3)	0.011 (2)
O8	0.029 (2)	0.053 (3)	0.040 (3)	−0.005 (2)	0.012 (2)	0.014 (2)
O9	0.044 (3)	0.050 (3)	0.035 (3)	−0.015 (2)	0.018 (2)	−0.006 (2)

Geometric parameters (Å, º) top

C1—C6	1.372 (10)	C13—O3	1.282 (9)
C1—C2	1.412 (11)	C14—N3	1.481 (9)
C1—N1	1.417 (9)	C14—C15	1.503 (11)
C2—C3	1.388 (10)	C14—H14A	0.9700
C2—H2A	0.9300	C14—H14B	0.9700
C3—C4	1.440 (10)	C15—N4	1.486 (10)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.361 (10)	C15—H15B	0.9700
C4—H4	0.9300	C16—C17	1.446 (9)
C5—C6	1.383 (10)	C16—N4	1.489 (9)
C5—H5	0.9300	C16—H16A	0.9700
C6—N2	1.389 (10)	C16—H16B	0.9700
C7—N1	1.348 (10)	C17—O5	1.248 (9)
C7—N2	1.364 (10)	C17—O6	1.271 (9)
C7—H7	0.9300	C18—C19	1.456 (11)
C8—N2	1.498 (10)	C18—N4	1.552 (9)
C8—C9	1.527 (10)	C18—H18A	0.9700
C8—H8A	0.9700	C18—H18B	0.9700
C8—H8B	0.9700	C19—O7	1.224 (9)
C9—C9ⁱ	1.509 (15)	C19—O8	1.293 (8)
C9—H9A	0.9700	C20—O9	1.291 (9)
C9—H9B	0.9700	C20—H20A	0.9822
C10—O1	1.148 (10)	C20—H20B	0.9735
C10—O2	1.316 (10)	C20—H20C	0.9611
C10—C11	1.536 (11)	Hg1—N1	2.138 (6)
C11—N3	1.492 (10)	Hg1—N4	2.364 (6)
C11—H11A	0.9700	Hg1—N3	2.390 (6)
C11—H11B	0.9700	Hg1—O3	2.473 (5)
C12—N3	1.488 (10)	Hg1—O5	2.547 (5)
C12—C13	1.569 (10)	Hg1—O1	2.604 (6)
C12—H12A	0.9700	O2—H2	0.8200
C12—H12B	0.9700	O8—H8	0.8200
C13—O4	1.258 (9)	O9—H9	0.8200

C6—C1—C2	124.2 (7)	C17—C16—N4	112.3 (6)
C6—C1—N1	109.3 (6)	C17—C16—H16A	109.1
C2—C1—N1	126.3 (6)	N4—C16—H16A	109.1
C3—C2—C1	113.6 (7)	C17—C16—H16B	109.1
C3—C2—H2A	123.2	N4—C16—H16B	109.1
C1—C2—H2A	123.2	H16A—C16—H16B	107.9
C2—C3—C4	121.8 (7)	O5—C17—O6	124.2 (6)
C2—C3—H3	119.1	O5—C17—C16	122.2 (6)
C4—C3—H3	119.1	O6—C17—C16	113.5 (6)
C5—C4—C3	121.9 (7)	C19—C18—N4	113.2 (6)
C5—C4—H4	119.1	C19—C18—H18A	108.9
C3—C4—H4	119.1	N4—C18—H18A	108.9
C4—C5—C6	116.7 (7)	C19—C18—H18B	108.9
C4—C5—H5	121.6	N4—C18—H18B	108.9
C6—C5—H5	121.6	H18A—C18—H18B	107.7
C1—C6—C5	121.6 (7)	O7—C19—O8	122.2 (7)
C1—C6—N2	106.0 (6)	O7—C19—C18	126.9 (7)
C5—C6—N2	132.4 (7)	O8—C19—C18	110.8 (6)
N1—C7—N2	110.3 (7)	O9—C20—H20A	111.4
N1—C7—H7	124.9	O9—C20—H20B	111.5
N2—C7—H7	124.9	H20A—C20—H20B	106.6
N2—C8—C9	111.6 (6)	O9—C20—H20C	111.3
N2—C8—H8A	109.3	H20A—C20—H20C	107.5
C9—C8—H8A	109.3	H20B—C20—H20C	108.3
N2—C8—H8B	109.3	N1—Hg1—N4	137.4 (2)
C9—C8—H8B	109.3	N1—Hg1—N3	146.4 (2)
H8A—C8—H8B	108.0	N4—Hg1—N3	75.6 (2)
C9ⁱ—C9—C8	113.0 (9)	N1—Hg1—O3	85.8 (2)
C9ⁱ—C9—H9A	109.0	N4—Hg1—O3	131.86 (19)
C8—C9—H9A	109.0	N3—Hg1—O3	68.26 (19)
C9ⁱ—C9—H9B	109.0	N1—Hg1—O5	106.7 (2)
C8—C9—H9B	109.0	N4—Hg1—O5	67.09 (18)
H9A—C9—H9B	107.8	N3—Hg1—O5	91.30 (19)
O1—C10—O2	123.9 (8)	O3—Hg1—O5	82.73 (18)
O1—C10—C11	124.8 (8)	N1—Hg1—O1	99.7 (2)
O2—C10—C11	111.3 (6)	N4—Hg1—O1	92.9 (2)
N3—C11—C10	108.2 (6)	N3—Hg1—O1	66.2 (2)
N3—C11—H11A	110.1	O3—Hg1—O1	100.25 (19)
C10—C11—H11A	110.1	O5—Hg1—O1	153.57 (18)
N3—C11—H11B	110.1	C7—N1—C1	105.6 (6)
C10—C11—H11B	110.1	C7—N1—Hg1	122.1 (5)
H11A—C11—H11B	108.4	C1—N1—Hg1	132.2 (5)
N3—C12—C13	110.5 (6)	C7—N2—C6	108.5 (6)
N3—C12—H12A	109.5	C7—N2—C8	126.6 (6)
C13—C12—H12A	109.5	C6—N2—C8	124.9 (6)
N3—C12—H12B	109.5	C14—N3—C12	108.5 (6)
C13—C12—H12B	109.5	C14—N3—C11	109.0 (5)
H12A—C12—H12B	108.1	C12—N3—C11	110.2 (6)
O4—C13—O3	124.0 (7)	C14—N3—Hg1	109.5 (4)
O4—C13—C12	117.8 (6)	C12—N3—Hg1	106.9 (4)
O3—C13—C12	118.1 (6)	C11—N3—Hg1	112.6 (4)
N3—C14—C15	111.8 (6)	C15—N4—C16	112.1 (6)
N3—C14—H14A	109.2	C15—N4—C18	109.8 (6)
C15—C14—H14A	109.2	C16—N4—C18	110.4 (6)
N3—C14—H14B	109.2	C15—N4—Hg1	108.6 (4)
C15—C14—H14B	109.2	C16—N4—Hg1	106.5 (4)
H14A—C14—H14B	107.9	C18—N4—Hg1	109.3 (4)
N4—C15—C14	112.7 (6)	C10—O1—Hg1	113.3 (6)
N4—C15—H15A	109.1	C10—O2—H2	109.5
C14—C15—H15A	109.1	C13—O3—Hg1	112.0 (4)
N4—C15—H15B	109.1	C17—O5—Hg1	108.7 (4)
C14—C15—H15B	109.1	C19—O8—H8	109.5
H15A—C15—H15B	107.8	C20—O9—H9	109.5

C6—C1—C2—C3	−1.8 (11)	O5—Hg1—N3—C14	−76.7 (5)
N1—C1—C2—C3	173.8 (7)	O1—Hg1—N3—C14	89.0 (5)
C1—C2—C3—C4	4.6 (11)	N1—Hg1—N3—C12	−83.0 (6)
C2—C3—C4—C5	−4.0 (12)	N4—Hg1—N3—C12	106.5 (4)
C3—C4—C5—C6	0.1 (11)	O3—Hg1—N3—C12	−41.0 (4)
C2—C1—C6—C5	−1.9 (11)	O5—Hg1—N3—C12	40.6 (4)
N1—C1—C6—C5	−178.2 (7)	O1—Hg1—N3—C12	−153.7 (5)
C2—C1—C6—N2	178.3 (7)	N1—Hg1—N3—C11	38.1 (7)
N1—C1—C6—N2	2.0 (8)	N4—Hg1—N3—C11	−132.3 (5)
C4—C5—C6—C1	2.7 (11)	O3—Hg1—N3—C11	80.1 (5)
C4—C5—C6—N2	−177.5 (8)	O5—Hg1—N3—C11	161.8 (4)
N2—C8—C9—C9ⁱ	−67.0 (10)	O1—Hg1—N3—C11	−32.5 (4)
O1—C10—C11—N3	−21.5 (10)	C14—C15—N4—C16	159.3 (6)
O2—C10—C11—N3	156.8 (6)	C14—C15—N4—C18	−77.6 (8)
N3—C12—C13—O4	168.5 (6)	C14—C15—N4—Hg1	41.9 (7)
N3—C12—C13—O3	−15.8 (9)	C17—C16—N4—C15	−72.5 (8)
N3—C14—C15—N4	−54.6 (8)	C17—C16—N4—C18	164.8 (6)
N4—C16—C17—O5	−16.4 (10)	C17—C16—N4—Hg1	46.2 (7)
N4—C16—C17—O6	159.9 (6)	C19—C18—N4—C15	165.0 (6)
N4—C18—C19—O7	−14.0 (12)	C19—C18—N4—C16	−71.0 (8)
N4—C18—C19—O8	161.4 (6)	C19—C18—N4—Hg1	45.9 (7)
N2—C7—N1—C1	−4.4 (8)	N1—Hg1—N4—C15	171.9 (5)
N2—C7—N1—Hg1	172.8 (5)	N3—Hg1—N4—C15	−15.9 (5)
C6—C1—N1—C7	1.4 (8)	O3—Hg1—N4—C15	26.0 (6)
C2—C1—N1—C7	−174.8 (7)	O5—Hg1—N4—C15	81.8 (5)
C6—C1—N1—Hg1	−175.4 (5)	O1—Hg1—N4—C15	−80.5 (5)
C2—C1—N1—Hg1	8.4 (11)	N1—Hg1—N4—C16	51.0 (6)
N4—Hg1—N1—C7	−12.1 (8)	N3—Hg1—N4—C16	−136.8 (5)
N3—Hg1—N1—C7	−178.3 (5)	O3—Hg1—N4—C16	−94.9 (5)
O3—Hg1—N1—C7	143.1 (6)	O5—Hg1—N4—C16	−39.1 (4)
O5—Hg1—N1—C7	62.0 (6)	O1—Hg1—N4—C16	158.6 (4)
O1—Hg1—N1—C7	−117.2 (6)	N1—Hg1—N4—C18	−68.3 (6)
N4—Hg1—N1—C1	164.2 (5)	N3—Hg1—N4—C18	103.8 (5)
N3—Hg1—N1—C1	−2.0 (9)	O3—Hg1—N4—C18	145.8 (4)
O3—Hg1—N1—C1	−40.6 (6)	O5—Hg1—N4—C18	−158.5 (5)
O5—Hg1—N1—C1	−121.7 (6)	O1—Hg1—N4—C18	39.3 (5)
O1—Hg1—N1—C1	59.1 (7)	O2—C10—O1—Hg1	174.3 (6)
N1—C7—N2—C6	5.8 (9)	C11—C10—O1—Hg1	−7.6 (10)
N1—C7—N2—C8	−177.3 (6)	N1—Hg1—O1—C10	−125.7 (6)
C1—C6—N2—C7	−4.7 (8)	N4—Hg1—O1—C10	95.2 (6)
C5—C6—N2—C7	175.6 (8)	N3—Hg1—O1—C10	22.3 (6)
C1—C6—N2—C8	178.3 (6)	O3—Hg1—O1—C10	−38.2 (6)
C5—C6—N2—C8	−1.4 (13)	O5—Hg1—O1—C10	56.1 (8)
C9—C8—N2—C7	100.6 (9)	O4—C13—O3—Hg1	153.3 (6)
C9—C8—N2—C6	−82.9 (9)	C12—C13—O3—Hg1	−22.1 (8)
C15—C14—N3—C12	−79.7 (7)	N1—Hg1—O3—C13	−166.5 (5)
C15—C14—N3—C11	160.2 (6)	N4—Hg1—O3—C13	−9.0 (6)
C15—C14—N3—Hg1	36.6 (7)	N3—Hg1—O3—C13	35.3 (5)
C13—C12—N3—C14	163.5 (6)	O5—Hg1—O3—C13	−59.1 (5)
C13—C12—N3—C11	−77.1 (7)	O1—Hg1—O3—C13	94.4 (5)
C13—C12—N3—Hg1	45.5 (6)	O6—C17—O5—Hg1	163.8 (6)
C10—C11—N3—C14	−80.9 (7)	C16—C17—O5—Hg1	−20.2 (8)
C10—C11—N3—C12	160.1 (6)	N1—Hg1—O5—C17	−101.6 (5)
C10—C11—N3—Hg1	40.9 (6)	N4—Hg1—O5—C17	33.4 (4)
N1—Hg1—N3—C14	159.6 (5)	N3—Hg1—O5—C17	107.1 (5)
N4—Hg1—N3—C14	−10.8 (4)	O3—Hg1—O5—C17	175.0 (5)
O3—Hg1—N3—C14	−158.4 (5)	O1—Hg1—O5—C17	76.6 (6)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱⁱ	0.82	1.74	2.534 (7)	164
O8—H8···O4ⁱⁱⁱ	0.82	1.84	2.462 (7)	131
O9—H9···O6^iv	0.82	2.00	2.744 (7)	150

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

Experimental details

Crystal data
Chemical formula	[Hg₂(C₁₀H₁₄N₂O₈)₂(C₁₈H₁₈N₄)]·2CH₄O
M_r	1336.09
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	10.274 (2), 19.990 (3), 11.4717 (17)
β (°)	104.035 (13)
V (Å³)	2285.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.79
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.21, 0.29
No. of measured, independent and observed [I > 2σ(I)] reflections	14826, 4397, 3744
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.121, 1.04
No. of reflections	4397
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −1.60
Absolute structure	Refinement

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Hg1—N1	2.138 (6)	Hg1—O3	2.473 (5)
Hg1—N4	2.364 (6)	Hg1—O5	2.547 (5)
Hg1—N3	2.390 (6)	Hg1—O1	2.604 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.82	1.74	2.534 (7)	164
O8—H8···O4ⁱⁱ	0.82	1.84	2.462 (7)	131
O9—H9···O6ⁱⁱⁱ	0.82	2.00	2.744 (7)	150

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

Acknowledgements

X-WZ thanks Zhengzhou University of Light Industry for research facilities

References

Aghabozorg, H., Bagheri, S., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008). Acta Cryst. E64, m1065–m1066. Web of Science CSD CrossRef IUCr Journals Google Scholar
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