metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bis(μ-N,N′,N′′-tri-3-pyridylpyridine-1,3,5-tricarboxamide-κ2N:N′)bis­­[di­chloridomercury(II)] methanol disolvate

aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China, and bCollege of Chemical Engineering and Food Science, Zhongzhou University, Zhengzhou 450044, People's Republic of China
*Correspondence e-mail: wujie@zzu.edu.cn

(Received 17 May 2011; accepted 28 May 2011; online 4 June 2011)

The title dinuclear centrosymmetric complex, [Hg2Cl4(C24H18N6O3)2]·2CH3OH, comprises HgII atoms coordinated by two Cl atoms and two N atoms from ligands in a distorted tetra­hedral geometry. The solvent mol­ecules are linked by hydrogen bonds.

Related literature

For general background, see: Fortner et al. (2005[Fortner, K. C., Bigi, J. P. & Brown, S. N. (2005). Inorg. Chem. 44, 2803-2814.]). For a related structure, see: Qin et al. (2003[Qin, Z., Jennings, M. C. & Puddephatt, R. J. (2003). Inorg. Chem. 42, 1956-1965.]).

[Scheme 1]

Experimental

Crystal data
  • [Hg2Cl4(C24H18N6O3)2]·2CH4O

  • Mr = 1483.95

  • Triclinic, [P \overline 1]

  • a = 8.6772 (17) Å

  • b = 12.243 (2) Å

  • c = 13.530 (3) Å

  • α = 66.81 (3)°

  • β = 84.66 (3)°

  • γ = 86.40 (3)°

  • V = 1315.0 (4) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 6.10 mm−1

  • T = 293 K

  • 0.20 × 0.18 × 0.16 mm

Data collection
  • Rigaku Saturn724 diffractometer

  • Absorption correction: numerical (CrystalClear; Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.738, Tmax = 1.000

  • 14489 measured reflections

  • 5170 independent reflections

  • 4461 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.074

  • S = 1.10

  • 5170 reflections

  • 345 parameters

  • H-atom parameters constrained

  • Δρmax = 0.66 e Å−3

  • Δρmin = −0.65 e Å−3

Table 1
Selected bond lengths (Å)

Hg1—Cl1 2.3574 (15)
Hg1—Cl2 2.3687 (19)
Hg1—N3i 2.385 (4)
Hg1—N1 2.400 (4)
Symmetry code: (i) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4⋯N6ii 0.82 1.94 2.740 (6) 167
N5—H5A⋯O1iv 0.86 2.42 3.141 (6) 142
Symmetry codes: (ii) x+1, y-1, z-1; (iii) -x, -y+3, -z+1; (iv) -x+1, -y+2, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In recent years the rapid progress in supramolecular chemistry has contributed to discovery of special novel structures being of significance for functional materials (Fortner et al. 2005). To control the topology of molecular assemblies, tripodal ligands are proved promising and useful in this area. For example, N,N',N'',-tris(3-pyridinyl)-1,3,5-benzenetricarboxamide (Z (Qin et al. 2003) has been selected as an excellent tripodal ligand and many intriguing complexes have been successfully accomplished with this ligand. In this work, we selected this ligand as linker, generating a new coordination complex, [Hg~2~(C~24~H~18Ñ~6Õ~3~)~2~Cl~4~]2(CH~3ÕH), (I), which is reported here. In the compound, HgII atom is four-coordinated by two N atoms from two ligands and two Cl atoms in a distorted tetrahedral coordination sphere (Fig. 1, Table 1). The two HgII atoms are bridged with two ligands to form a microporous MOFs with 28-number ring. The Hg(II)—N distances are 2.385 (4) Å and 2.400 (4) Å, respectively. The Hg···Hg distance in the ring is 13.568 (5) Å. In the crystal structure, intermolecular hydrogen bonds N2—H—Cl1, N5—H—O1, and the O4—H—N6 (arising from the CH3OH and ligand) generate the three-dimensional network (Fig. 2, Table 2).

Related literature top

For related literature, see: Fortner et al. (2005); Qin et al. (2003).

Experimental top

The ligand N,N',N''-tris(3-pyridinyl)-1,3,5-benzenetricarboxamide (0.1 mmol, 0.044 g) in DMF (1 mL) was added dropwise to a solution of HgCl2 (0.05 mmol, 0.014 g) in methanol (5 mL). The precipitate was filtered and the resulting solution was allowed to stand at room temperature in the dark. After one week good quality colourless crystals were obtained, separated from a filtrate and dried in air.

Refinement top

H atoms were generated geometrically, with C-H = 0.96, 0.86 and 0.93Å for methyl, N and aromatic H, respectively, and constrained to ride their parent atoms with Uiso(H) = x times Ueq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title complex showing the labeling of the non-H atoms. H atoms have been omitted. Symmetry code used to generate the complete molecule: 1-x, 2-y, 1-z.
[Figure 2] Fig. 2. View of the crystal packing along the a axis. Hydrogen bonds are shown as dashed lines.
Bis(µ-N,N',N''-tri-3-pyridylpyridine-1,3,5- tricarboxamide-κ2N:N')bis[dichloridomercury(II)] methanol disolvate top
Crystal data top
[Hg2Cl4(C24H18N6O3)2]·2CH4OZ = 1
Mr = 1483.95F(000) = 720
Triclinic, P1Dx = 1.874 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6772 (17) ÅCell parameters from 3621 reflections
b = 12.243 (2) Åθ = 2.8–26.0°
c = 13.530 (3) ŵ = 6.10 mm1
α = 66.81 (3)°T = 293 K
β = 84.66 (3)°Prism, colorless
γ = 86.40 (3)°0.20 × 0.18 × 0.16 mm
V = 1315.0 (4) Å3
Data collection top
Rigaku Saturn724
diffractometer
5170 independent reflections
Radiation source: fine-focus sealed tube4461 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 28.5714 pixels mm-1θmax = 26.0°, θmin = 2.8°
dtprofit.ref scansh = 1010
Absorption correction: numerical
(CrystalClear; Rigaku/MSC, 2006)
k = 1515
Tmin = 0.738, Tmax = 1.000l = 1616
14489 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0211P)2 + 1.2163P]
where P = (Fo2 + 2Fc2)/3
5170 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.65 e Å3
Crystal data top
[Hg2Cl4(C24H18N6O3)2]·2CH4Oγ = 86.40 (3)°
Mr = 1483.95V = 1315.0 (4) Å3
Triclinic, P1Z = 1
a = 8.6772 (17) ÅMo Kα radiation
b = 12.243 (2) ŵ = 6.10 mm1
c = 13.530 (3) ÅT = 293 K
α = 66.81 (3)°0.20 × 0.18 × 0.16 mm
β = 84.66 (3)°
Data collection top
Rigaku Saturn724
diffractometer
5170 independent reflections
Absorption correction: numerical
(CrystalClear; Rigaku/MSC, 2006)
4461 reflections with I > 2σ(I)
Tmin = 0.738, Tmax = 1.000Rint = 0.044
14489 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.10Δρmax = 0.66 e Å3
5170 reflectionsΔρmin = 0.65 e Å3
345 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
xyzUiso*/Ueq
Hg10.06417 (3)1.50692 (2)0.291708 (18)0.04562 (9)
Cl10.01030 (19)1.70597 (13)0.26971 (13)0.0578 (4)
Cl20.0589 (2)1.32182 (15)0.35590 (16)0.0730 (5)
O10.6022 (4)1.1328 (4)0.6921 (3)0.0588 (12)
O20.0476 (5)1.1393 (4)1.0191 (3)0.0609 (13)
O30.5110 (4)0.6889 (3)1.1175 (3)0.0447 (10)
O40.5046 (4)0.2218 (4)0.2685 (3)0.0502 (11)
H40.59390.19500.27460.075*
N10.2878 (5)1.4403 (4)0.3940 (3)0.0388 (11)
N20.3666 (5)1.2240 (4)0.6615 (3)0.0328 (10)
H2A0.27431.22540.69040.039*
N30.8189 (5)0.4833 (4)0.8782 (3)0.0396 (11)
N40.5735 (5)0.6980 (4)0.9476 (3)0.0370 (11)
H4A0.55600.73940.88150.044*
N50.1166 (5)0.9886 (4)1.1696 (3)0.0383 (11)
H5A0.18400.93161.19330.046*
N60.2183 (5)1.0971 (4)1.2982 (4)0.0440 (12)
C10.4282 (7)1.4747 (5)0.3503 (4)0.0470 (15)
H10.43921.53310.28090.056*
C20.5569 (7)1.4272 (5)0.4037 (5)0.0519 (16)
H20.65431.45130.36990.062*
C30.5436 (6)1.3435 (5)0.5077 (4)0.0431 (14)
H30.63101.31130.54540.052*
C40.3975 (6)1.3086 (4)0.5546 (4)0.0324 (12)
C50.2711 (6)1.3585 (5)0.4947 (4)0.0356 (13)
H50.17221.33430.52530.043*
C60.4667 (6)1.1419 (4)0.7223 (4)0.0321 (12)
C70.4036 (5)1.0577 (4)0.8305 (4)0.0267 (11)
C80.2881 (5)1.0880 (4)0.8931 (4)0.0282 (11)
H80.23881.16250.86630.034*
C90.2452 (5)1.0064 (4)0.9972 (4)0.0269 (11)
C100.3142 (5)0.8937 (4)1.0355 (4)0.0283 (11)
H100.28390.83931.10420.034*
C110.4282 (5)0.8615 (4)0.9720 (4)0.0267 (11)
C120.4739 (5)0.9443 (4)0.8704 (4)0.0299 (12)
H120.55220.92410.82840.036*
C130.1274 (6)1.0525 (5)1.0623 (4)0.0329 (12)
C140.0080 (5)1.0042 (4)1.2477 (4)0.0298 (12)
C150.1147 (6)1.0857 (4)1.2230 (4)0.0342 (12)
H150.12571.13451.15110.041*
C160.1994 (7)1.0275 (5)1.3999 (5)0.0476 (15)
H160.26821.03721.45300.057*
C170.0839 (6)0.9419 (5)1.4314 (4)0.0427 (14)
H170.07820.89231.50360.051*
C180.0221 (6)0.9311 (5)1.3551 (4)0.0366 (13)
H180.10320.87521.37470.044*
C190.5064 (6)0.7406 (4)1.0210 (4)0.0291 (11)
C200.6681 (6)0.5949 (4)0.9664 (4)0.0325 (12)
C210.7074 (6)0.5125 (5)1.0650 (4)0.0408 (14)
H210.67100.52141.12840.049*
C220.8021 (7)0.4163 (5)1.0679 (4)0.0463 (15)
H220.83000.35971.13370.056*
C230.8552 (6)0.4041 (5)0.9739 (4)0.0416 (14)
H230.91820.33860.97730.050*
C240.7266 (6)0.5763 (5)0.8752 (4)0.0429 (15)
H240.70030.63140.80830.051*
C250.4092 (7)0.1503 (6)0.3571 (5)0.0653 (19)
H25A0.43940.15530.42170.098*
H25B0.41960.06930.36350.098*
H25C0.30340.17740.34690.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.05767 (17)0.03596 (14)0.03701 (14)0.01382 (10)0.00540 (11)0.00942 (10)
Cl10.0633 (10)0.0361 (8)0.0662 (11)0.0097 (7)0.0067 (8)0.0158 (8)
Cl20.0673 (11)0.0461 (10)0.0887 (14)0.0063 (9)0.0155 (10)0.0055 (9)
O10.040 (2)0.053 (3)0.044 (3)0.016 (2)0.011 (2)0.017 (2)
O20.078 (3)0.046 (3)0.035 (2)0.040 (2)0.006 (2)0.003 (2)
O30.066 (3)0.031 (2)0.024 (2)0.0152 (19)0.0028 (19)0.0008 (17)
O40.048 (2)0.056 (3)0.038 (2)0.023 (2)0.003 (2)0.012 (2)
N10.049 (3)0.034 (3)0.021 (2)0.003 (2)0.005 (2)0.001 (2)
N20.028 (2)0.034 (2)0.021 (2)0.0056 (19)0.0017 (18)0.0043 (19)
N30.046 (3)0.037 (3)0.032 (3)0.016 (2)0.004 (2)0.012 (2)
N40.043 (3)0.032 (2)0.026 (2)0.018 (2)0.005 (2)0.003 (2)
N50.045 (3)0.030 (2)0.027 (2)0.020 (2)0.005 (2)0.002 (2)
N60.041 (3)0.047 (3)0.038 (3)0.008 (2)0.001 (2)0.012 (2)
C10.056 (4)0.037 (3)0.028 (3)0.003 (3)0.011 (3)0.005 (3)
C20.043 (4)0.051 (4)0.042 (4)0.003 (3)0.009 (3)0.000 (3)
C30.036 (3)0.040 (3)0.037 (3)0.004 (3)0.005 (3)0.002 (3)
C40.038 (3)0.027 (3)0.025 (3)0.001 (2)0.001 (2)0.002 (2)
C50.035 (3)0.036 (3)0.026 (3)0.004 (2)0.001 (2)0.002 (2)
C60.029 (3)0.028 (3)0.031 (3)0.000 (2)0.002 (2)0.004 (2)
C70.028 (3)0.023 (3)0.023 (3)0.002 (2)0.004 (2)0.002 (2)
C80.027 (3)0.023 (3)0.031 (3)0.006 (2)0.005 (2)0.006 (2)
C90.031 (3)0.026 (3)0.021 (3)0.005 (2)0.003 (2)0.007 (2)
C100.030 (3)0.025 (3)0.025 (3)0.001 (2)0.001 (2)0.005 (2)
C110.026 (3)0.025 (3)0.026 (3)0.008 (2)0.006 (2)0.007 (2)
C120.028 (3)0.029 (3)0.028 (3)0.000 (2)0.004 (2)0.007 (2)
C130.034 (3)0.028 (3)0.032 (3)0.004 (2)0.001 (2)0.009 (2)
C140.026 (3)0.029 (3)0.035 (3)0.003 (2)0.000 (2)0.014 (2)
C150.037 (3)0.031 (3)0.026 (3)0.003 (2)0.003 (2)0.003 (2)
C160.045 (4)0.057 (4)0.036 (3)0.009 (3)0.008 (3)0.017 (3)
C170.050 (4)0.046 (4)0.028 (3)0.009 (3)0.003 (3)0.012 (3)
C180.037 (3)0.032 (3)0.035 (3)0.010 (2)0.006 (3)0.008 (3)
C190.031 (3)0.024 (3)0.028 (3)0.002 (2)0.002 (2)0.007 (2)
C200.034 (3)0.025 (3)0.034 (3)0.007 (2)0.001 (2)0.008 (2)
C210.053 (4)0.036 (3)0.022 (3)0.009 (3)0.001 (3)0.002 (2)
C220.058 (4)0.031 (3)0.033 (3)0.013 (3)0.000 (3)0.002 (3)
C230.047 (3)0.029 (3)0.040 (3)0.015 (3)0.005 (3)0.005 (3)
C240.051 (4)0.040 (3)0.029 (3)0.021 (3)0.004 (3)0.007 (3)
C250.060 (4)0.072 (5)0.053 (4)0.014 (4)0.004 (4)0.016 (4)
Geometric parameters (Å, º) top
Hg1—Cl12.3574 (15)C5—H50.9300
Hg1—Cl22.3687 (19)C6—C71.496 (6)
Hg1—N3i2.385 (4)C7—C81.380 (6)
Hg1—N12.400 (4)C7—C121.399 (6)
O1—C61.221 (6)C8—C91.401 (6)
O2—C131.203 (6)C8—H80.9300
O3—C191.209 (6)C9—C101.386 (6)
O4—C251.404 (7)C9—C131.513 (7)
O4—H40.8200C10—C111.390 (6)
N1—C11.321 (7)C10—H100.9300
N1—C51.336 (6)C11—C121.388 (6)
N2—C61.347 (6)C11—C191.509 (6)
N2—C41.421 (6)C12—H120.9300
N2—H2A0.8600C14—C151.382 (7)
N3—C231.329 (6)C14—C181.387 (7)
N3—C241.340 (6)C15—H150.9300
N3—Hg1i2.385 (4)C16—C171.371 (7)
N4—C191.363 (6)C16—H160.9300
N4—C201.410 (6)C17—C181.358 (7)
N4—H4A0.8600C17—H170.9300
N5—C131.348 (6)C18—H180.9300
N5—C141.411 (6)C20—C211.377 (7)
N5—H5A0.8600C20—C241.386 (7)
N6—C161.322 (7)C21—C221.383 (7)
N6—C151.338 (6)C21—H210.9300
C1—C21.359 (8)C22—C231.372 (7)
C1—H10.9300C22—H220.9300
C2—C31.375 (7)C23—H230.9300
C2—H20.9300C24—H240.9300
C3—C41.377 (7)C25—H25A0.9600
C3—H30.9300C25—H25B0.9600
C4—C51.387 (7)C25—H25C0.9600
Cl1—Hg1—Cl2140.17 (6)C9—C10—H10119.8
Cl1—Hg1—N3i105.41 (12)C11—C10—H10119.8
Cl2—Hg1—N3i101.24 (13)C12—C11—C10119.1 (4)
Cl1—Hg1—N1107.24 (12)C12—C11—C19122.8 (4)
Cl2—Hg1—N197.44 (12)C10—C11—C19117.9 (4)
N3i—Hg1—N198.31 (15)C11—C12—C7120.8 (4)
C25—O4—H4109.5C11—C12—H12119.6
C1—N1—C5119.3 (5)C7—C12—H12119.6
C1—N1—Hg1121.6 (4)O2—C13—N5123.2 (5)
C5—N1—Hg1118.9 (4)O2—C13—C9121.0 (5)
C6—N2—C4126.8 (4)N5—C13—C9115.7 (4)
C6—N2—H2A116.6C15—C14—C18118.0 (4)
C4—N2—H2A116.6C15—C14—N5123.7 (5)
C23—N3—C24118.1 (4)C18—C14—N5118.2 (4)
C23—N3—Hg1i125.5 (3)N6—C15—C14122.7 (5)
C24—N3—Hg1i115.6 (3)N6—C15—H15118.6
C19—N4—C20128.3 (4)C14—C15—H15118.6
C19—N4—H4A115.9N6—C16—C17123.6 (5)
C20—N4—H4A115.9N6—C16—H16118.2
C13—N5—C14127.8 (4)C17—C16—H16118.2
C13—N5—H5A116.1C18—C17—C16118.8 (5)
C14—N5—H5A116.1C18—C17—H17120.6
C16—N6—C15117.5 (5)C16—C17—H17120.6
N1—C1—C2121.9 (5)C17—C18—C14119.3 (5)
N1—C1—H1119.1C17—C18—H18120.4
C2—C1—H1119.1C14—C18—H18120.4
C1—C2—C3120.3 (5)O3—C19—N4124.0 (4)
C1—C2—H2119.9O3—C19—C11121.6 (4)
C3—C2—H2119.9N4—C19—C11114.3 (4)
C2—C3—C4118.2 (5)C21—C20—C24117.7 (5)
C2—C3—H3120.9C21—C20—N4126.6 (5)
C4—C3—H3120.9C24—C20—N4115.7 (4)
C3—C4—C5118.7 (5)C20—C21—C22118.6 (5)
C3—C4—N2124.2 (5)C20—C21—H21120.7
C5—C4—N2117.1 (4)C22—C21—H21120.7
N1—C5—C4121.7 (5)C23—C22—C21120.2 (5)
N1—C5—H5119.1C23—C22—H22119.9
C4—C5—H5119.1C21—C22—H22119.9
O1—C6—N2123.2 (5)N3—C23—C22121.8 (5)
O1—C6—C7120.1 (4)N3—C23—H23119.1
N2—C6—C7116.7 (4)C22—C23—H23119.1
C8—C7—C12119.6 (4)N3—C24—C20123.6 (5)
C8—C7—C6123.8 (4)N3—C24—H24118.2
C12—C7—C6116.5 (4)C20—C24—H24118.2
C7—C8—C9119.9 (4)O4—C25—H25A109.5
C7—C8—H8120.1O4—C25—H25B109.5
C9—C8—H8120.1H25A—C25—H25B109.5
C10—C9—C8120.0 (4)O4—C25—H25C109.5
C10—C9—C13124.5 (4)H25A—C25—H25C109.5
C8—C9—C13115.4 (4)H25B—C25—H25C109.5
C9—C10—C11120.5 (4)
Cl1—Hg1—N1—C174.8 (4)C6—C7—C12—C11177.1 (4)
Cl2—Hg1—N1—C1136.9 (4)C14—N5—C13—O25.0 (9)
N3i—Hg1—N1—C134.3 (4)C14—N5—C13—C9173.5 (5)
Cl1—Hg1—N1—C5111.1 (4)C10—C9—C13—O2163.7 (5)
Cl2—Hg1—N1—C537.2 (4)C8—C9—C13—O218.9 (8)
N3i—Hg1—N1—C5139.8 (4)C10—C9—C13—N514.9 (8)
C5—N1—C1—C21.7 (9)C8—C9—C13—N5162.6 (5)
Hg1—N1—C1—C2172.4 (5)C13—N5—C14—C154.9 (9)
N1—C1—C2—C32.2 (10)C13—N5—C14—C18177.3 (5)
C1—C2—C3—C41.0 (9)C16—N6—C15—C140.7 (8)
C2—C3—C4—C50.6 (8)C18—C14—C15—N60.7 (8)
C2—C3—C4—N2179.4 (5)N5—C14—C15—N6178.5 (5)
C6—N2—C4—C320.0 (8)C15—N6—C16—C172.7 (9)
C6—N2—C4—C5160.0 (5)N6—C16—C17—C183.3 (10)
C1—N1—C5—C40.0 (8)C16—C17—C18—C141.8 (9)
Hg1—N1—C5—C4174.2 (4)C15—C14—C18—C170.0 (8)
C3—C4—C5—N11.1 (8)N5—C14—C18—C17178.0 (5)
N2—C4—C5—N1178.9 (5)C20—N4—C19—O35.2 (9)
C4—N2—C6—O12.2 (9)C20—N4—C19—C11172.9 (5)
C4—N2—C6—C7176.4 (5)C12—C11—C19—O3150.9 (5)
O1—C6—C7—C8148.0 (5)C10—C11—C19—O323.8 (7)
N2—C6—C7—C833.4 (7)C12—C11—C19—N427.2 (7)
O1—C6—C7—C1228.5 (7)C10—C11—C19—N4158.1 (4)
N2—C6—C7—C12150.0 (5)C19—N4—C20—C212.8 (9)
C12—C7—C8—C91.8 (7)C19—N4—C20—C24177.1 (5)
C6—C7—C8—C9174.6 (5)C24—C20—C21—C220.1 (8)
C7—C8—C9—C102.7 (7)N4—C20—C21—C22180.0 (5)
C7—C8—C9—C13174.9 (4)C20—C21—C22—C230.0 (9)
C8—C9—C10—C111.2 (7)C24—N3—C23—C220.7 (9)
C13—C9—C10—C11176.1 (5)Hg1i—N3—C23—C22168.6 (4)
C9—C10—C11—C121.0 (7)C21—C22—C23—N30.4 (9)
C9—C10—C11—C19176.0 (4)C23—N3—C24—C200.6 (9)
C10—C11—C12—C71.9 (7)Hg1i—N3—C24—C20169.7 (4)
C19—C11—C12—C7176.5 (5)C21—C20—C24—N30.2 (9)
C8—C7—C12—C110.4 (8)N4—C20—C24—N3179.7 (5)
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N6ii0.821.942.740 (6)167
N2—H2A···Cl1iii0.862.643.465 (4)162
N5—H5A···O1iv0.862.423.141 (6)142
Symmetry codes: (ii) x+1, y1, z1; (iii) x, y+3, z+1; (iv) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formula[Hg2Cl4(C24H18N6O3)2]·2CH4O
Mr1483.95
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.6772 (17), 12.243 (2), 13.530 (3)
α, β, γ (°)66.81 (3), 84.66 (3), 86.40 (3)
V3)1315.0 (4)
Z1
Radiation typeMo Kα
µ (mm1)6.10
Crystal size (mm)0.20 × 0.18 × 0.16
Data collection
DiffractometerRigaku Saturn724
diffractometer
Absorption correctionNumerical
(CrystalClear; Rigaku/MSC, 2006)
Tmin, Tmax0.738, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14489, 5170, 4461
Rint0.044
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.074, 1.10
No. of reflections5170
No. of parameters345
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.65

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Hg1—Cl12.3574 (15)Hg1—N3i2.385 (4)
Hg1—Cl22.3687 (19)Hg1—N12.400 (4)
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N6ii0.821.942.740 (6)166.7
N2—H2A···Cl1iii0.862.643.465 (4)162.4
N5—H5A···O1iv0.862.423.141 (6)141.8
Symmetry codes: (ii) x+1, y1, z1; (iii) x, y+3, z+1; (iv) x+1, y+2, z+2.
 

Acknowledgements

We gratefully acknowledge financial support by the Student Innovative Pilot Project of Zhengzhou University (grant No. 2010cxsy095).

References

First citationFortner, K. C., Bigi, J. P. & Brown, S. N. (2005). Inorg. Chem. 44, 2803–2814.  Web of Science CrossRef PubMed CAS Google Scholar
First citationQin, Z., Jennings, M. C. & Puddephatt, R. J. (2003). Inorg. Chem. 42, 1956–1965.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationRigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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