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ISSN: 2056-9890

Di­chlorido(6-methyl-2,2′-bi­pyridine-κ2N,N′)mercury(II)

aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, bDepartment of Chemistry, Islamic Azad University, Kazeroon Branch, Kazeroon, Fars, Iran, and cIslamic Azad University, Izeh Branch, Izeh, Khozestan, Iran
*Correspondence e-mail: v_amani2002@yahoo.com

(Received 10 October 2008; accepted 10 October 2008; online 15 October 2008)

In the mol­ecule of the title compound, [HgCl2(C11H10N2)], the HgII atom is four-coordinated in a distorted tetra­hedral configuration by two N atoms from a 6-methyl-2,2′-bipyridine ligand and two Cl atoms. There is a ππ contact between the pyridine rings [centroid–centroid distance = 3.9758 (5) Å].

Related literature

For related literature, see: Ahmadi, Kalateh, Ebadi et al. (2008[Ahmadi, R., Kalateh, K., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1266.]); Ahmadi, Khalighi et al. (2008[Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.]); Ahmadi, Kalateh, Abedi et al. (2008[Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306-m1307.]); Kalateh, Ahmadi et al. (2008[Kalateh, K., Ahmadi, R., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1353-m1354.]); Kalateh, Ebadi et al. (2008[Kalateh, K., Ebadi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1397-m1398.]); Khalighi et al. (2008[Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211-m1212.]); Khavasi et al. (2008[Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848-1854.]); Tadayon Pour et al. (2008[Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.]); Yousefi, Rashidi Vahid et al. (2008[Yousefi, M., Rashidi Vahid, R., Amani, V., Arab Chamjangali, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m1339-m1340.]); Yousefi, Tadayon Pour et al. (2008[Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259.]); Yousefi, Khalighi et al. (2008[Yousefi, M., Khalighi, A., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1284-m1285.]). For related structures, see: Chen et al. (2006[Chen, W. T., Wang, M. S., Liu, X., Guo, G. C. & Huang, J. S. (2006). Cryst. Growth Des. 6, 2289-2300.]); Liu et al. (2004[Liu, Q. D., Wang, R. & Wang, S. (2004). Dalton Trans. pp. 2073-2079.]).

[Scheme 1]

Experimental

Crystal data
  • [HgCl2(C11H10N2)]

  • Mr = 441.70

  • Monoclinic, P 21 /c

  • a = 9.4742 (19) Å

  • b = 16.164 (3) Å

  • c = 8.2107 (16) Å

  • β = 105.70 (3)°

  • V = 1210.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 13.13 mm−1

  • T = 120 (2) K

  • 0.50 × 0.15 × 0.09 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: numerical via shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005[Stoe & Cie (2005). X-SHAPE and X-RED. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.108, Tmax = 0.307

  • 14334 measured reflections

  • 3263 independent reflections

  • 2925 reflections with I > 2σ(I)

  • Rint = 0.100

Refinement
  • R[F2 > 2σ(F2)] = 0.092

  • wR(F2) = 0.197

  • S = 1.14

  • 3263 reflections

  • 147 parameters

  • H-atom parameters constrained

  • Δρmax = 1.39 e Å−3

  • Δρmin = −1.12 e Å−3

Table 1
Selected geometric parameters (Å, °)

Cl1—Hg1 2.438 (2)
Cl2—Hg1 2.423 (3)
N1—Hg1 2.394 (9)
N2—Hg1 2.297 (10)
Cl2—Hg1—Cl1 112.32 (10)
N1—Hg1—Cl1 103.4 (2)
N1—Hg1—Cl2 121.1 (2)
N2—Hg1—Cl1 132.8 (2)
N2—Hg1—Cl2 109.8 (2)
N2—Hg1—N1 71.0 (3)

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Recently, we reported the syntheses and crystal structures of [Zn(5,5'-dmbpy)Cl2], (II), (Khalighi et al., 2008), [Zn(6-mbpy)Cl2], (III), (Ahmadi, Kalateh, Ebadi et al., 2008), [HgI2(4,4'-dmbpy)], (IV), (Yousefi, Tadayon Pour et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)2]n, (V), (Ahmadi, Khalighi et al., 2008), [Hg(5,5'-dmbpy)I2], (VI), (Tadayon Pour et al., 2008), [Cu(5,5'-dcbpy)(en)(H2O)2].2.5H2O, (VII), (Yousefi, Khalighi et al., 2008), [Hg(dmphen)I2], (VIII), (Yousefi, Rashidi Vahid et al., 2008), [In(4,4'-dmbpy)Cl3(DMSO)], (IX), (Ahmadi, Kalateh, Abedi et al., 2008), [In(5,5'-dmbpy)Cl3(MeOH)], (X), (Kalateh, Ahmadi et al., 2008), {[HgCl(dm4bt)]2(µ-Cl)2}, (XI), (Khavasi et al., 2008) and {[HgBr(4,4'-dmbpy)]2(µ-Br)2}, (XII), (Kalateh, Ebadi et al., 2008) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2'-bipyridine, 4,4'-dmbpy is 4,4'-dimethyl-2,2' -bipyridine, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-dicarboxylate, en is ethylene- diamine, dmphen is 4,7-diphenyl-1,10-phenanthroline, DMSO is dimethyl sulfoxide and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are several HgII complexes, with formula, [HgCl2(N—N)], such as [HgCl2(bipy)], (XIII) and [HgCl2(bipy)][HgCl2], (XIV), (Chen et al., 2006) and [HgCl2(dpdmbip)].CH2Cl2, (XV), (Liu et al., 2004) [where bipy is 2,2'-bipyridine and dpdmbip is 4,4'-diphenyl-6,6'-dimethyl-2,2'-bipyrimidine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (I), (Fig. 1), the HgII atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 6-methyl-2,2'-bipyridine and two Cl atoms. The Hg—Cl and Hg—N bond lengths and angles (Table 1) are within normal ranges, as in (XIV) and (XV).

In the crystal structure, the π-π contact (Fig. 2) between the pyridine rings, Cg2—Cg3i [symmetry code: (i) x, 1/2 - y, -1/2 + z, where Cg2 and Cg3 are centroids of the rings (N1/C2-C6) and (N2/C7-C11), respectively] may stabilize the structure, with centroid-centroid distance of 3.9758 (5) Å.

Related literature top

For related literature, see: Ahmadi, Kalateh, Ebadi et al. (2008); Ahmadi, Khalighi et al. (2008); Ahmadi, Kalateh, Abedi et al. (2008); Kalateh, Ahmadi et al. (2008); Kalateh, Ebadi et al. (2008); Khalighi et al. (2008); Khavasi et al. (2008); Tadayon Pour et al. (2008); Yousefi, Rashidi Vahid et al. (2008); Yousefi, Tadayon Pour et al. (2008); Yousefi, Khalighi et al. (2008). For related structures, see: Chen et al. (2006); Liu et al. (2004).

Experimental top

For the preparation of the title compound, (I), a solution of 6-methyl-2,2'-bipyridine (0.15 g, 0.88 mmol) in methanol (10 ml) was added to a solution of HgCl2 (0.24 g, 0.88 mmol) in acetonitrile (30 ml) and the resulting colorless solution was stirred for 20 min at 313 K. Then, it was left to evaporate slowly at room temperature. After one week, colorless needle crystals of the title compound were isolated (yield; 0.28 g, 72.03%).

Refinement top

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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound.
Dichlorido(6-methyl-2,2'-bipyridine-κ2N,N')mercury(II) top
Crystal data top
[HgCl2(C11H10N2)]F(000) = 816
Mr = 441.70Dx = 2.424 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1234 reflections
a = 9.4742 (19) Åθ = 2.2–29.2°
b = 16.164 (3) ŵ = 13.13 mm1
c = 8.2107 (16) ÅT = 120 K
β = 105.70 (3)°Needle, colorless
V = 1210.4 (4) Å30.50 × 0.15 × 0.09 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3263 independent reflections
Radiation source: fine-focus sealed tube2925 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
ϕ and ω scansθmax = 29.2°, θmin = 2.2°
Absorption correction: numerical
via shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)
h = 1211
Tmin = 0.108, Tmax = 0.307k = 2222
14334 measured reflectionsl = 911
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.092H-atom parameters constrained
wR(F2) = 0.197 w = 1/[σ2(Fo2) + (0.1638P)2 + 3.9978P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.005
3263 reflectionsΔρmax = 1.39 e Å3
147 parametersΔρmin = 1.12 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (2)
Crystal data top
[HgCl2(C11H10N2)]V = 1210.4 (4) Å3
Mr = 441.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.4742 (19) ŵ = 13.13 mm1
b = 16.164 (3) ÅT = 120 K
c = 8.2107 (16) Å0.50 × 0.15 × 0.09 mm
β = 105.70 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3263 independent reflections
Absorption correction: numerical
via shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)
2925 reflections with I > 2σ(I)
Tmin = 0.108, Tmax = 0.307Rint = 0.100
14334 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0920 restraints
wR(F2) = 0.197H-atom parameters constrained
S = 1.14Δρmax = 1.39 e Å3
3263 reflectionsΔρmin = 1.12 e Å3
147 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
Hg10.81647 (4)0.05913 (2)0.29276 (5)0.0248 (3)
Cl10.8330 (3)0.00698 (17)0.5642 (3)0.0244 (5)
Cl20.7288 (3)0.03469 (19)0.0569 (4)0.0299 (6)
N10.6912 (9)0.1861 (5)0.3103 (11)0.0187 (16)
N20.9427 (10)0.1664 (6)0.2138 (11)0.0227 (18)
C10.4897 (12)0.1134 (9)0.3776 (14)0.032 (2)
H1A0.44930.08730.27000.048*
H1B0.41230.12610.42850.048*
H1C0.55850.07670.45000.048*
C20.5650 (11)0.1903 (7)0.3534 (13)0.024 (2)
C30.5077 (11)0.2686 (8)0.3770 (14)0.030 (2)
H30.41960.27250.40580.036*
C40.5820 (12)0.3385 (8)0.3573 (14)0.029 (2)
H40.54570.39000.37640.034*
C50.7106 (11)0.3335 (6)0.3093 (15)0.024 (2)
H50.76010.38110.29240.028*
C60.7649 (11)0.2543 (6)0.2868 (11)0.0175 (17)
C70.9018 (10)0.2430 (6)0.2327 (11)0.0175 (17)
C80.9819 (11)0.3114 (7)0.2004 (15)0.025 (2)
H80.95220.36480.21810.030*
C91.1063 (13)0.2995 (8)0.1417 (14)0.031 (2)
H91.16090.34370.11910.037*
C101.1450 (11)0.2146 (8)0.1183 (13)0.028 (2)
H101.22580.20290.07840.033*
C111.0615 (10)0.1513 (7)0.1553 (12)0.0211 (19)
H111.08700.09690.13990.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.0291 (4)0.0223 (4)0.0234 (4)0.00241 (12)0.0075 (2)0.00050 (12)
Cl10.0251 (11)0.0254 (12)0.0226 (10)0.0004 (9)0.0061 (8)0.0033 (9)
Cl20.0307 (13)0.0297 (13)0.0264 (12)0.0031 (11)0.0032 (10)0.0077 (11)
N10.012 (3)0.021 (4)0.020 (4)0.001 (3)0.000 (3)0.003 (3)
N20.022 (4)0.032 (5)0.014 (3)0.001 (3)0.004 (3)0.007 (3)
C10.019 (4)0.050 (7)0.023 (5)0.005 (5)0.002 (4)0.002 (5)
C20.014 (4)0.034 (5)0.023 (5)0.002 (4)0.001 (3)0.002 (4)
C30.015 (4)0.044 (7)0.026 (5)0.001 (4)0.003 (4)0.012 (5)
C40.025 (5)0.039 (6)0.020 (4)0.005 (4)0.003 (4)0.004 (4)
C50.018 (4)0.018 (4)0.031 (5)0.003 (3)0.000 (4)0.005 (4)
C60.025 (4)0.014 (4)0.008 (3)0.000 (3)0.005 (3)0.001 (3)
C70.018 (4)0.023 (4)0.009 (3)0.002 (3)0.000 (3)0.004 (3)
C80.018 (4)0.030 (5)0.025 (5)0.006 (4)0.003 (3)0.000 (4)
C90.025 (5)0.042 (7)0.018 (4)0.004 (4)0.008 (4)0.017 (5)
C100.017 (4)0.045 (7)0.019 (4)0.004 (4)0.001 (3)0.004 (5)
C110.019 (4)0.027 (5)0.017 (4)0.008 (4)0.003 (3)0.009 (4)
Geometric parameters (Å, º) top
Cl1—Hg12.438 (2)C5—C61.410 (13)
Cl2—Hg12.423 (3)C5—H50.9300
N1—Hg12.394 (9)C6—N11.347 (13)
N2—Hg12.297 (10)C6—C71.492 (14)
C1—C21.473 (17)C7—N21.319 (14)
C1—H1A0.9600C7—C81.406 (14)
C1—H1B0.9600C8—C91.402 (17)
C1—H1C0.9600C8—H80.9300
C2—N11.338 (13)C9—C101.446 (18)
C2—C31.411 (17)C9—H90.9300
C3—C41.363 (18)C10—C111.377 (16)
C3—H30.9300C10—H100.9300
C4—C51.381 (16)C11—N21.360 (13)
C4—H40.9300C11—H110.9300
Cl2—Hg1—Cl1112.32 (10)C3—C4—C5120.6 (11)
N1—Hg1—Cl1103.4 (2)C3—C4—H4119.7
N1—Hg1—Cl2121.1 (2)C5—C4—H4119.7
N2—Hg1—Cl1132.8 (2)C4—C5—C6118.1 (10)
N2—Hg1—Cl2109.8 (2)C4—C5—H5121.0
N2—Hg1—N171.0 (3)C6—C5—H5121.0
C2—N1—Hg1123.6 (7)N1—C6—C5120.3 (10)
C2—N1—C6122.1 (9)N1—C6—C7117.9 (9)
C6—N1—Hg1114.1 (6)C5—C6—C7121.8 (9)
C7—N2—Hg1118.9 (7)N2—C7—C8121.7 (9)
C7—N2—C11120.4 (10)N2—C7—C6117.2 (9)
C11—N2—Hg1120.6 (8)C8—C7—C6121.1 (9)
C2—C1—H1A109.5C9—C8—C7120.2 (11)
C2—C1—H1B109.5C9—C8—H8119.9
H1A—C1—H1B109.5C7—C8—H8119.9
C2—C1—H1C109.5C8—C9—C10116.3 (11)
H1A—C1—H1C109.5C8—C9—H9121.8
H1B—C1—H1C109.5C10—C9—H9121.8
N1—C2—C3119.1 (10)C11—C10—C9119.6 (10)
N1—C2—C1119.5 (10)C11—C10—H10120.2
C3—C2—C1121.3 (10)C9—C10—H10120.2
C4—C3—C2119.8 (11)N2—C11—C10121.7 (10)
C4—C3—H3120.1N2—C11—H11119.2
C2—C3—H3120.1C10—C11—H11119.2
C2—N1—Hg1—Cl151.3 (8)C5—C6—C7—C80.5 (13)
C2—N1—Hg1—Cl275.5 (8)N2—C7—C8—C92.0 (15)
C2—N1—Hg1—N2177.6 (8)C6—C7—C8—C9176.9 (9)
C6—N1—Hg1—Cl1123.3 (6)C7—C8—C9—C100.2 (14)
C6—N1—Hg1—Cl2109.9 (6)C8—C9—C10—C110.7 (14)
C6—N1—Hg1—N27.7 (6)C9—C10—C11—N20.0 (15)
C7—N2—Hg1—Cl183.2 (8)C3—C2—N1—C60.7 (14)
C7—N2—Hg1—Cl2124.8 (7)C1—C2—N1—C6179.9 (9)
C7—N2—Hg1—N17.6 (7)C3—C2—N1—Hg1173.6 (7)
C11—N2—Hg1—Cl194.0 (7)C1—C2—N1—Hg15.7 (13)
C11—N2—Hg1—Cl258.0 (7)C5—C6—N1—C20.7 (14)
C11—N2—Hg1—N1175.2 (8)C7—C6—N1—C2177.8 (8)
N1—C2—C3—C40.7 (16)C5—C6—N1—Hg1174.0 (7)
C1—C2—C3—C4178.5 (10)C7—C6—N1—Hg17.5 (10)
C2—C3—C4—C52.0 (16)C8—C7—N2—C112.7 (14)
C3—C4—C5—C62.0 (16)C6—C7—N2—C11176.2 (8)
C4—C5—C6—N10.6 (14)C8—C7—N2—Hg1174.5 (7)
C4—C5—C6—C7179.1 (9)C6—C7—N2—Hg16.6 (11)
N1—C6—C7—N21.0 (12)C10—C11—N2—C71.7 (14)
C5—C6—C7—N2179.4 (9)C10—C11—N2—Hg1175.4 (7)
N1—C6—C7—C8177.9 (9)

Experimental details

Crystal data
Chemical formula[HgCl2(C11H10N2)]
Mr441.70
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)9.4742 (19), 16.164 (3), 8.2107 (16)
β (°) 105.70 (3)
V3)1210.4 (4)
Z4
Radiation typeMo Kα
µ (mm1)13.13
Crystal size (mm)0.50 × 0.15 × 0.09
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionNumerical
via shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)
Tmin, Tmax0.108, 0.307
No. of measured, independent and
observed [I > 2σ(I)] reflections
14334, 3263, 2925
Rint0.100
(sin θ/λ)max1)0.686
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.092, 0.197, 1.14
No. of reflections3263
No. of parameters147
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.39, 1.12

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Cl1—Hg12.438 (2)N1—Hg12.394 (9)
Cl2—Hg12.423 (3)N2—Hg12.297 (10)
Cl2—Hg1—Cl1112.32 (10)N2—Hg1—Cl1132.8 (2)
N1—Hg1—Cl1103.4 (2)N2—Hg1—Cl2109.8 (2)
N1—Hg1—Cl2121.1 (2)N2—Hg1—N171.0 (3)
 

Acknowledgements

The authors are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

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