Bis{μ-2,5-bis­[4-(2-pyridylmethyl­amino)phen­yl]-1,3,4-oxadiazole}bis­[dichlorido­mercury(II)]

Liu, L.-L.; Hou, G.-G.; Ma, J.-P.; Huang, R.-Q.; Dong, Y.-B.

doi:10.1107/S1600536808006788

Bis{μ-2,5-bis[4-(2-pyridylmethylamino)phenyl]-1,3,4-oxadiazole}bis[dichloridomercury(II)]

L.-L. Liu, G.-G. Hou, J.-P. Ma, R.-Q. Huang and Y.-B. Dong

In the title centrosymmetric compound, [Hg₂Cl₄(C₂₆H₂₂N₆O)₂], each Hg^II center adopts a distorted HgN₃Cl₂ trigonal bipyramidal coordination geometry, formed by two pyridine N atoms, one imine N atom and two chloride anions. Within the organic ligand, the oxadiazole ring is nearly coplanar with the two benzene rings [dihedral angles = 5.9 (4) and 6.5 (4)°] and nearly perpendicular to the two pyridine rings with the same dihedral angle of 77.4 (4)°. The two organic ligands bridge two Hg^II ions to form the macrocyclic complex. Intermolecular N—H

Cl and N—H

N hydrogen bonding helps to stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808006788/xu2406sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808006788/xu2406Isup2.hkl Contains datablock I

CCDC reference: 684437

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.011 Å
R factor = 0.045
wR factor = 0.118
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.113     0.153
            Tmin and Tmax expected:      0.102     0.153
            RR =      1.101
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.11
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.62
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Hg1    -   Cl2     ..       5.98 su
PLAT318_ALERT_2_C Check Hybridisation of  N5     in Main Residue .          ?
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11

Alert level G
PLAT793_ALERT_2_G Check the Absolute Configuration of N3     .....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Combining metal ions with oxadiazole-bridging organic ligands may result in coordination polymers with novel network connectivities (Dong et al., 2003). Our interest in understanding the relationship between the metal coordination modes with such ligands and their extended structures led us to synthesize the title Hg^II compound, (I).

As shown in Fig. 1, there are five primary bonds to each Hg^II center, three Hg—N bonds and two Hg—Cl bonds, resulting in a distorted trigonal bipyramid coordination geometry around the Hg center. Three Hg—N bond distances (Table 1) are significantly different, but all agree with those reported previously (Gallagher et al., 1999; Grupce et al., 1999). The bond angles at Hg1 atom rang from 70.81 (18)° [N4—Hg—N3] to 145.19 (16)° [N4—Hg1—Cl1]. While the ligand chelates to a Hg atom by a pyridine N and an imine N atoms, the other pyridine N atom bridges to another Hg atom to form the title binuclear macrocyclic complex with the Hg···Hg separation of 12.969 (2) Å. Within the ligand, the dihedral angles between the oxadiazole and N4-pyridine rings and between the oxadiazole and N6-pyridine rings are identical [77.4 (4)°]. Intermolecular N—H···Cl and N—H···N hydrogen bonding helps to stabilize the crystal structure (Table 2).

Related literature top

For general background, see: Dong et al. (2003). For related structures, see: Gallagher et al. (1999); Grupce et al. (1999). For synthesis, see: Ren et al. (1995).

Experimental top

2,5-Bis(4-aminophenyl)-1,3,4-oxadiazole (L1) was prepared according to the literature method (Ren et al., 1995). A solution of L1 (2.56 g, 10 mmol) and 2-pyridylaldehyde (4 ml) in anhydrous EtOH (20 ml) was refluxed for 24 h, with HCOOH as catalyzer. After the mixture was cooled to room temperature, the precipitated product was filtered off, washed with EtOH and dried, yielding a light-yellow power [2,5-bis(4-((2-pyridinyl)methyleneamino)phenyl) -1,3,4-oxadiazole] (L2). Then the L2 was deoxidized by NaBH₄ in anhydrous CH₃OH (20 ml). The solvent was removed under reduced pressure, and the residue was washed with water to afford the ligand [2,5-bis(4-((2-pyridinylmethyl)amino)phenyl)-1,3,4-oxadiazole] (L) as a yellow solid. A solution of HgCl₂ (13.58 mg, 0.05 mmol) in EtOH (8 ml) was layered onto a solution of the ligand L (21.7 mg, 0.05 mmol) in CH₂Cl₂ (8 ml). Single yellow crystals of the title compound were obtained after 7 d at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing 30% displacement ellipsoids, hydrogen atoms have been omitted [symmetry code: (i) -x + 2,-y,-z].

Bis{µ-2,5-bis[4-(2-pyridylmethylamino)phenyl]-1,3,4- oxadiazole}bis[dichloridomercury(II)] top

Crystal data top

[Hg₂Cl₄(C₂₆H₂₂N₆O)₂]	Z = 1
M_r = 1411.98	F(000) = 684
Triclinic, P1	D_x = 1.834 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5426 (19) Å	Cell parameters from 2786 reflections
b = 9.945 (2) Å	θ = 2.5–25.6°
c = 16.533 (4) Å	µ = 6.26 mm⁻¹
α = 83.773 (3)°	T = 298 K
β = 80.001 (3)°	Block, yellow
γ = 67.671 (2)°	0.40 × 0.40 × 0.30 mm
V = 1278.2 (5) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	4652 independent reflections
Radiation source: fine-focus sealed tube	3878 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
T_min = 0.113, T_max = 0.153	k = −12→11
6681 measured reflections	l = −20→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0677P)² + 1.1058P] where P = (F_o² + 2F_c²)/3
4652 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 2.20 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

[Hg₂Cl₄(C₂₆H₂₂N₆O)₂]	γ = 67.671 (2)°
M_r = 1411.98	V = 1278.2 (5) Å³
Triclinic, P1	Z = 1
a = 8.5426 (19) Å	Mo Kα radiation
b = 9.945 (2) Å	µ = 6.26 mm⁻¹
c = 16.533 (4) Å	T = 298 K
α = 83.773 (3)°	0.40 × 0.40 × 0.30 mm
β = 80.001 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	4652 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	3878 reflections with I > 2σ(I)
T_min = 0.113, T_max = 0.153	R_int = 0.023
6681 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	Δρ_max = 2.20 e Å⁻³
4652 reflections	Δρ_min = −0.84 e Å⁻³
325 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
N6	0.7661 (9)	−0.1644 (7)	−0.4018 (4)	0.0529 (16)
C5	0.6054 (9)	−0.1027 (8)	−0.3635 (4)	0.0418 (16)
C6	0.5468 (11)	−0.2001 (8)	−0.2981 (4)	0.0516 (19)
H6A	0.5341	−0.2764	−0.3251	0.062*
H6B	0.6356	−0.2462	−0.2636	0.062*
N5	0.3889 (8)	−0.1271 (7)	−0.2465 (4)	0.0495 (15)
H5	0.2971	−0.1354	−0.2559	0.059*
C7	0.3785 (9)	−0.0447 (7)	−0.1829 (4)	0.0399 (15)
Hg1	0.95952 (4)	0.33183 (3)	0.324081 (19)	0.05155 (14)
Cl1	1.0242 (3)	0.1191 (2)	0.25208 (17)	0.0723 (6)
Cl2	0.6820 (3)	0.4107 (3)	0.41247 (15)	0.0854 (8)
O1	0.4543 (5)	0.2726 (5)	0.0143 (3)	0.0354 (10)
N3	0.8599 (7)	0.5232 (6)	0.2061 (3)	0.0371 (12)
H3	0.9511	0.5157	0.1666	0.045*
C19	0.7868 (8)	0.4113 (8)	0.1043 (4)	0.0413 (16)
H19	0.9008	0.3795	0.0803	0.050*
C13	0.3210 (8)	0.2390 (7)	0.0028 (4)	0.0380 (15)
C14	0.3883 (8)	0.3660 (7)	0.0762 (4)	0.0356 (14)
C18	0.7341 (8)	0.4991 (7)	0.1714 (4)	0.0363 (14)
C9	0.4933 (9)	0.0866 (8)	−0.1119 (4)	0.0419 (16)
H9	0.5837	0.1135	−0.1062	0.050*
C11	0.2122 (8)	0.0950 (8)	−0.0669 (4)	0.0421 (16)
H11	0.1104	0.1278	−0.0308	0.051*
C10	0.3426 (8)	0.1393 (8)	−0.0594 (4)	0.0368 (14)
N2	0.2294 (7)	0.3897 (7)	0.1005 (4)	0.0472 (15)
C15	0.5034 (8)	0.4177 (7)	0.1072 (4)	0.0347 (14)
C16	0.4485 (8)	0.5123 (8)	0.1708 (4)	0.0412 (16)
H16	0.3331	0.5495	0.1924	0.049*
C12	0.2300 (9)	0.0027 (8)	−0.1270 (4)	0.0436 (16)
H12	0.1413	−0.0282	−0.1301	0.052*
C21	0.8165 (10)	0.6524 (7)	0.2504 (5)	0.0481 (18)
H21A	0.7151	0.6637	0.2903	0.058*
H21B	0.7898	0.7365	0.2123	0.058*
N1	0.1858 (7)	0.3049 (8)	0.0520 (4)	0.0508 (16)
C23	1.0048 (10)	0.7665 (8)	0.2940 (5)	0.0516 (19)
H23	0.9519	0.8514	0.2637	0.062*
C20	0.6746 (8)	0.3714 (8)	0.0733 (4)	0.0404 (15)
H20	0.7131	0.3121	0.0286	0.048*
C4	0.5020 (11)	0.0367 (9)	−0.3836 (5)	0.0547 (19)
H4	0.3909	0.0769	−0.3564	0.066*
N4	1.0367 (7)	0.5233 (6)	0.3357 (3)	0.0420 (13)
C22	0.9585 (9)	0.6475 (7)	0.2942 (4)	0.0401 (15)
C25	1.2047 (10)	0.6336 (9)	0.3837 (5)	0.055 (2)
H25	1.2881	0.6265	0.4151	0.066*
C17	0.5620 (9)	0.5517 (8)	0.2022 (4)	0.0432 (16)
H17	0.5226	0.6150	0.2451	0.052*
C3	0.5663 (14)	0.1169 (10)	−0.4453 (6)	0.067 (2)
H3A	0.5009	0.2133	−0.4581	0.080*
C8	0.5139 (8)	−0.0050 (8)	−0.1727 (4)	0.0415 (16)
H8	0.6178	−0.0405	−0.2071	0.050*
C1	0.8213 (13)	−0.0863 (11)	−0.4622 (6)	0.069 (2)
H1	0.9318	−0.1286	−0.4897	0.083*
C24	1.1299 (11)	0.7583 (9)	0.3391 (5)	0.058 (2)
H24	1.1628	0.8373	0.3391	0.069*
C26	1.1544 (9)	0.5180 (8)	0.3812 (4)	0.0481 (17)
H26	1.2039	0.4332	0.4124	0.058*
C2	0.7255 (14)	0.0522 (11)	−0.4864 (6)	0.070 (3)
H2	0.7688	0.1012	−0.5302	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N6	0.064 (4)	0.042 (4)	0.052 (4)	−0.020 (3)	−0.011 (3)	0.011 (3)
C5	0.052 (4)	0.034 (4)	0.043 (4)	−0.017 (3)	−0.012 (3)	−0.006 (3)
C6	0.071 (5)	0.036 (4)	0.045 (4)	−0.019 (4)	−0.001 (4)	−0.003 (3)
N5	0.053 (4)	0.051 (4)	0.048 (4)	−0.023 (3)	−0.006 (3)	−0.012 (3)
C7	0.047 (4)	0.024 (3)	0.048 (4)	−0.013 (3)	−0.011 (3)	0.004 (3)
Hg1	0.0623 (2)	0.03300 (18)	0.0642 (2)	−0.02039 (14)	−0.02216 (14)	0.00926 (13)
Cl1	0.0659 (13)	0.0379 (11)	0.122 (2)	−0.0203 (10)	−0.0315 (12)	−0.0090 (11)
Cl2	0.0705 (14)	0.104 (2)	0.0654 (15)	−0.0260 (14)	−0.0016 (11)	0.0254 (13)
O1	0.030 (2)	0.039 (3)	0.039 (3)	−0.0149 (19)	−0.0056 (18)	−0.0019 (19)
N3	0.040 (3)	0.035 (3)	0.038 (3)	−0.016 (2)	−0.007 (2)	−0.001 (2)
C19	0.030 (3)	0.046 (4)	0.042 (4)	−0.009 (3)	0.000 (3)	−0.005 (3)
C13	0.036 (3)	0.039 (4)	0.041 (4)	−0.015 (3)	−0.011 (3)	0.004 (3)
C14	0.034 (3)	0.036 (4)	0.034 (4)	−0.010 (3)	−0.002 (3)	0.000 (3)
C18	0.041 (4)	0.034 (4)	0.036 (4)	−0.016 (3)	−0.008 (3)	0.004 (3)
C9	0.037 (4)	0.041 (4)	0.049 (4)	−0.016 (3)	−0.012 (3)	0.005 (3)
C11	0.034 (3)	0.048 (4)	0.043 (4)	−0.014 (3)	−0.005 (3)	−0.001 (3)
C10	0.035 (3)	0.042 (4)	0.036 (4)	−0.017 (3)	−0.012 (3)	0.004 (3)
N2	0.040 (3)	0.055 (4)	0.050 (4)	−0.020 (3)	0.002 (3)	−0.019 (3)
C15	0.031 (3)	0.037 (4)	0.035 (3)	−0.012 (3)	−0.007 (3)	0.006 (3)
C16	0.035 (3)	0.045 (4)	0.039 (4)	−0.011 (3)	−0.004 (3)	−0.004 (3)
C12	0.039 (4)	0.046 (4)	0.050 (4)	−0.021 (3)	−0.008 (3)	−0.002 (3)
C21	0.057 (4)	0.027 (4)	0.065 (5)	−0.013 (3)	−0.031 (4)	0.005 (3)
N1	0.035 (3)	0.070 (5)	0.055 (4)	−0.026 (3)	0.000 (3)	−0.022 (3)
C23	0.065 (5)	0.029 (4)	0.065 (5)	−0.014 (3)	−0.027 (4)	−0.001 (3)
C20	0.042 (4)	0.039 (4)	0.041 (4)	−0.015 (3)	−0.007 (3)	−0.005 (3)
C4	0.071 (5)	0.045 (5)	0.053 (5)	−0.022 (4)	−0.021 (4)	−0.001 (4)
N4	0.045 (3)	0.039 (3)	0.044 (3)	−0.013 (3)	−0.017 (3)	0.000 (3)
C22	0.049 (4)	0.029 (3)	0.040 (4)	−0.011 (3)	−0.011 (3)	−0.001 (3)
C25	0.057 (5)	0.055 (5)	0.059 (5)	−0.017 (4)	−0.027 (4)	−0.011 (4)
C17	0.045 (4)	0.041 (4)	0.042 (4)	−0.014 (3)	−0.003 (3)	−0.009 (3)
C3	0.094 (7)	0.042 (5)	0.071 (6)	−0.025 (5)	−0.040 (5)	0.017 (4)
C8	0.035 (3)	0.044 (4)	0.043 (4)	−0.010 (3)	−0.011 (3)	0.001 (3)
C1	0.072 (6)	0.076 (7)	0.062 (6)	−0.034 (5)	−0.014 (4)	0.014 (5)
C24	0.068 (5)	0.042 (5)	0.072 (5)	−0.023 (4)	−0.025 (4)	−0.009 (4)
C26	0.055 (4)	0.034 (4)	0.050 (4)	−0.006 (3)	−0.019 (3)	0.000 (3)
C2	0.096 (7)	0.077 (7)	0.060 (5)	−0.057 (6)	−0.032 (5)	0.028 (5)

Geometric parameters (Å, º) top

N6—C1	1.330 (11)	C11—C10	1.373 (9)
N6—C5	1.343 (10)	C11—C12	1.375 (10)
C5—C4	1.372 (11)	C11—H11	0.9300
C5—C6	1.520 (10)	N2—N1	1.407 (8)
C6—N5	1.437 (10)	C15—C16	1.385 (9)
C6—H6A	0.9700	C15—C20	1.388 (9)
C6—H6B	0.9700	C16—C17	1.368 (10)
N5—C7	1.373 (9)	C16—H16	0.9300
N5—H5	0.8600	C12—H12	0.9300
C7—C12	1.385 (10)	C21—C22	1.500 (10)
C7—C8	1.397 (9)	C21—H21A	0.9700
Hg1—Cl1	2.373 (2)	C21—H21B	0.9700
Hg1—Cl2	2.451 (2)	C23—C24	1.379 (11)
Hg1—N3	2.587 (6)	C23—C22	1.383 (10)
Hg1—N4	2.275 (6)	C23—H23	0.9300
Hg1—N6ⁱ	2.745 (7)	C20—H20	0.9300
O1—C13	1.350 (7)	C4—C3	1.394 (12)
O1—C14	1.355 (7)	C4—H4	0.9300
N3—C18	1.408 (8)	N4—C22	1.338 (9)
N3—C21	1.440 (9)	N4—C26	1.340 (9)
N3—H3	0.9100	C25—C24	1.361 (12)
C19—C20	1.358 (9)	C25—C26	1.378 (11)
C19—C18	1.390 (9)	C25—H25	0.9300
C19—H19	0.9300	C17—H17	0.9300
C13—N1	1.280 (9)	C3—C2	1.354 (14)
C13—C10	1.446 (9)	C3—H3A	0.9300
C14—N2	1.284 (8)	C8—H8	0.9300
C14—C15	1.452 (9)	C1—C2	1.365 (14)
C18—C17	1.381 (10)	C1—H1	0.9300
C9—C10	1.373 (10)	C24—H24	0.9300
C9—C8	1.374 (10)	C26—H26	0.9300
C9—H9	0.9300	C2—H2	0.9300

C1—N6—C5	117.3 (7)	C16—C15—C20	117.9 (6)
N6—C5—C4	122.1 (7)	C16—C15—C14	122.2 (6)
N6—C5—C6	114.8 (6)	C20—C15—C14	119.9 (6)
C4—C5—C6	123.0 (7)	C17—C16—C15	120.8 (6)
N5—C6—C5	114.9 (6)	C17—C16—H16	119.6
N5—C6—H6A	108.5	C15—C16—H16	119.6
C5—C6—H6A	108.5	C11—C12—C7	120.7 (6)
N5—C6—H6B	108.5	C11—C12—H12	119.6
C5—C6—H6B	108.5	C7—C12—H12	119.6
H6A—C6—H6B	107.5	N3—C21—C22	112.4 (6)
C7—N5—C6	122.8 (6)	N3—C21—H21A	109.1
C7—N5—H5	118.6	C22—C21—H21A	109.1
C6—N5—H5	118.6	N3—C21—H21B	109.1
N5—C7—C12	120.0 (6)	C22—C21—H21B	109.1
N5—C7—C8	121.8 (6)	H21A—C21—H21B	107.9
C12—C7—C8	118.1 (6)	C13—N1—N2	106.8 (5)
N4—Hg1—Cl1	145.19 (16)	C24—C23—C22	119.5 (7)
N4—Hg1—Cl2	99.31 (16)	C24—C23—H23	120.3
Cl1—Hg1—Cl2	114.87 (10)	C22—C23—H23	120.3
N4—Hg1—N3	70.81 (18)	C19—C20—C15	121.1 (6)
Cl1—Hg1—N3	98.44 (13)	C19—C20—H20	119.5
Cl2—Hg1—N3	95.30 (13)	C15—C20—H20	119.5
N4—Hg1—N6ⁱ	86.73 (19)	C5—C4—C3	118.9 (8)
Cl1—Hg1—N6ⁱ	84.60 (15)	C5—C4—H4	120.6
Cl2—Hg1—N6ⁱ	115.31 (15)	C3—C4—H4	120.6
N3—Hg1—N6ⁱ	144.82 (18)	C22—N4—C26	119.0 (6)
C13—O1—C14	103.7 (5)	C22—N4—Hg1	117.2 (4)
C18—N3—C21	120.2 (5)	C26—N4—Hg1	123.8 (5)
C18—N3—Hg1	110.2 (4)	N4—C22—C23	120.9 (7)
C21—N3—Hg1	98.4 (4)	N4—C22—C21	117.1 (6)
C18—N3—H3	109.1	C23—C22—C21	122.0 (6)
C21—N3—H3	109.1	C24—C25—C26	118.6 (7)
Hg1—N3—H3	109.1	C24—C25—H25	120.7
C20—C19—C18	121.1 (6)	C26—C25—H25	120.7
C20—C19—H19	119.5	C16—C17—C18	121.2 (6)
C18—C19—H19	119.5	C16—C17—H17	119.4
N1—C13—O1	111.7 (6)	C18—C17—H17	119.4
N1—C13—C10	128.3 (6)	C2—C3—C4	118.9 (8)
O1—C13—C10	120.0 (6)	C2—C3—H3A	120.6
N2—C14—O1	112.0 (6)	C4—C3—H3A	120.6
N2—C14—C15	130.1 (6)	C9—C8—C7	119.8 (6)
O1—C14—C15	117.8 (5)	C9—C8—H8	120.1
C17—C18—C19	117.8 (6)	C7—C8—H8	120.1
C17—C18—N3	124.0 (6)	N6—C1—C2	124.0 (9)
C19—C18—N3	118.1 (6)	N6—C1—H1	118.0
C10—C9—C8	121.6 (6)	C2—C1—H1	118.0
C10—C9—H9	119.2	C25—C24—C23	119.4 (7)
C8—C9—H9	119.2	C25—C24—H24	120.3
C10—C11—C12	120.9 (6)	C23—C24—H24	120.3
C10—C11—H11	119.5	N4—C26—C25	122.4 (7)
C12—C11—H11	119.5	N4—C26—H26	118.8
C11—C10—C9	118.5 (6)	C25—C26—H26	118.8
C11—C10—C13	120.4 (6)	C3—C2—C1	118.7 (9)
C9—C10—C13	121.0 (6)	C3—C2—H2	120.6
C14—N2—N1	105.8 (5)	C1—C2—H2	120.6

C1—N6—C5—C4	−1.7 (11)	C8—C7—C12—C11	4.7 (11)
C1—N6—C5—C6	177.0 (7)	C18—N3—C21—C22	170.7 (6)
N6—C5—C6—N5	168.7 (6)	Hg1—N3—C21—C22	51.3 (6)
C4—C5—C6—N5	−12.7 (11)	O1—C13—N1—N2	0.0 (8)
C5—C6—N5—C7	−77.9 (9)	C10—C13—N1—N2	−179.9 (7)
C6—N5—C7—C12	−169.2 (7)	C14—N2—N1—C13	−0.4 (8)
C6—N5—C7—C8	11.5 (11)	C18—C19—C20—C15	0.4 (11)
N4—Hg1—N3—C18	−162.2 (4)	C16—C15—C20—C19	3.5 (10)
Cl1—Hg1—N3—C18	52.0 (4)	C14—C15—C20—C19	−176.2 (6)
Cl2—Hg1—N3—C18	−64.2 (4)	N6—C5—C4—C3	−0.4 (11)
N6ⁱ—Hg1—N3—C18	144.6 (4)	C6—C5—C4—C3	−179.0 (7)
N4—Hg1—N3—C21	−35.6 (4)	Cl1—Hg1—N4—C22	93.9 (5)
Cl1—Hg1—N3—C21	178.6 (4)	Cl2—Hg1—N4—C22	−75.3 (5)
Cl2—Hg1—N3—C21	62.4 (4)	N3—Hg1—N4—C22	17.1 (5)
N6ⁱ—Hg1—N3—C21	−88.8 (5)	N6ⁱ—Hg1—N4—C22	169.6 (5)
C14—O1—C13—N1	0.3 (8)	Cl1—Hg1—N4—C26	−86.1 (6)
C14—O1—C13—C10	−179.8 (6)	Cl2—Hg1—N4—C26	104.7 (5)
C13—O1—C14—N2	−0.6 (7)	N3—Hg1—N4—C26	−162.9 (6)
C13—O1—C14—C15	176.6 (6)	N6ⁱ—Hg1—N4—C26	−10.5 (6)
C20—C19—C18—C17	−3.9 (11)	C26—N4—C22—C23	3.9 (10)
C20—C19—C18—N3	173.1 (6)	Hg1—N4—C22—C23	−176.2 (5)
C21—N3—C18—C17	−28.4 (10)	C26—N4—C22—C21	−174.5 (6)
Hg1—N3—C18—C17	84.8 (7)	Hg1—N4—C22—C21	5.4 (8)
C21—N3—C18—C19	154.7 (7)	C24—C23—C22—N4	−1.9 (11)
Hg1—N3—C18—C19	−92.1 (6)	C24—C23—C22—C21	176.4 (7)
C12—C11—C10—C9	−1.6 (11)	N3—C21—C22—N4	−44.7 (9)
C12—C11—C10—C13	178.6 (7)	N3—C21—C22—C23	136.9 (7)
C8—C9—C10—C11	2.0 (11)	C15—C16—C17—C18	0.3 (11)
C8—C9—C10—C13	−178.2 (6)	C19—C18—C17—C16	3.6 (11)
N1—C13—C10—C11	−5.6 (12)	N3—C18—C17—C16	−173.3 (6)
O1—C13—C10—C11	174.5 (6)	C5—C4—C3—C2	3.3 (12)
N1—C13—C10—C9	174.6 (8)	C10—C9—C8—C7	0.9 (11)
O1—C13—C10—C9	−5.3 (10)	N5—C7—C8—C9	175.1 (7)
O1—C14—N2—N1	0.6 (8)	C12—C7—C8—C9	−4.3 (10)
C15—C14—N2—N1	−176.1 (7)	C5—N6—C1—C2	0.9 (13)
N2—C14—C15—C16	−2.9 (12)	C26—C25—C24—C23	0.9 (13)
O1—C14—C15—C16	−179.4 (6)	C22—C23—C24—C25	−0.6 (12)
N2—C14—C15—C20	176.7 (7)	C22—N4—C26—C25	−3.5 (11)
O1—C14—C15—C20	0.2 (9)	Hg1—N4—C26—C25	176.6 (6)
C20—C15—C16—C17	−3.8 (10)	C24—C25—C26—N4	1.1 (12)
C14—C15—C16—C17	175.8 (7)	C4—C3—C2—C1	−4.1 (13)
C10—C11—C12—C7	−1.8 (11)	N6—C1—C2—C3	2.0 (15)
N5—C7—C12—C11	−174.7 (7)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2ⁱⁱ	0.91	2.36	3.191 (8)	152
N5—H5···Cl1ⁱⁱⁱ	0.86	2.68	3.517 (7)	166

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

Experimental details

Crystal data
Chemical formula	[Hg₂Cl₄(C₂₆H₂₂N₆O)₂]
M_r	1411.98
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.5426 (19), 9.945 (2), 16.533 (4)
α, β, γ (°)	83.773 (3), 80.001 (3), 67.671 (2)
V (Å³)	1278.2 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	6.26
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.113, 0.153
No. of measured, independent and observed [I > 2σ(I)] reflections	6681, 4652, 3878
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.118, 1.04
No. of reflections	4652
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.20, −0.84

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Hg1—Cl1	2.373 (2)	Hg1—N4	2.275 (6)
Hg1—Cl2	2.451 (2)	Hg1—N6ⁱ	2.745 (7)
Hg1—N3	2.587 (6)

N4—Hg1—Cl1	145.19 (16)	Cl2—Hg1—N3	95.30 (13)
N4—Hg1—Cl2	99.31 (16)	N4—Hg1—N6ⁱ	86.73 (19)
Cl1—Hg1—Cl2	114.87 (10)	Cl1—Hg1—N6ⁱ	84.60 (15)
N4—Hg1—N3	70.81 (18)	Cl2—Hg1—N6ⁱ	115.31 (15)
Cl1—Hg1—N3	98.44 (13)	N3—Hg1—N6ⁱ	144.82 (18)