PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1407.
Published online 2008 October 15. doi:  10.1107/S1600536808032777
PMCID: PMC2959542

Dichlorido(6-methyl-2,2′-bipyridine-κ2 N,N′)mercury(II)

Abstract

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 π–π contact between the pyridine rings [centroid–centroid distance = 3.9758 (5) Å].

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-m1407-scheme1.jpg

Experimental

Crystal data

  • [HgCl2(C11H10N2)]
  • M r = 441.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1407-efi1.jpg
  • 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 [triangle]) T min = 0.108, T max = 0.307
  • 14334 measured reflections
  • 3263 independent reflections
  • 2925 reflections with I > 2σ(I)
  • R int = 0.100

Refinement

  • R[F 2 > 2σ(F 2)] = 0.092
  • wR(F 2) = 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

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032777/hk2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032777/hk2551Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A partial packing diagram of the title compound.

Crystal data

[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

Bruker SMART CCD area-detector diffractometer3263 independent reflections
Radiation source: fine-focus sealed tube2925 reflections with I > 2σ(I)
graphiteRint = 0.100
[var phi] 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 = −12→11
Tmin = 0.108, Tmax = 0.307k = −22→22
14334 measured reflectionsl = −9→11

Refinement

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) = 0.197w = 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)

Special details

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)

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)

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, °)

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—Cl1−51.3 (8)C5—C6—C7—C8−0.5 (13)
C2—N1—Hg1—Cl275.5 (8)N2—C7—C8—C92.0 (15)
C2—N1—Hg1—N2177.6 (8)C6—C7—C8—C9−176.9 (9)
C6—N1—Hg1—Cl1123.3 (6)C7—C8—C9—C10−0.2 (14)
C6—N1—Hg1—Cl2−109.9 (6)C8—C9—C10—C11−0.7 (14)
C6—N1—Hg1—N2−7.7 (6)C9—C10—C11—N20.0 (15)
C7—N2—Hg1—Cl1−83.2 (8)C3—C2—N1—C6−0.7 (14)
C7—N2—Hg1—Cl2124.8 (7)C1—C2—N1—C6−179.9 (9)
C7—N2—Hg1—N17.6 (7)C3—C2—N1—Hg1173.6 (7)
C11—N2—Hg1—Cl194.0 (7)C1—C2—N1—Hg1−5.7 (13)
C11—N2—Hg1—Cl2−58.0 (7)C5—C6—N1—C20.7 (14)
C11—N2—Hg1—N1−175.2 (8)C7—C6—N1—C2−177.8 (8)
N1—C2—C3—C4−0.7 (16)C5—C6—N1—Hg1−174.0 (7)
C1—C2—C3—C4178.5 (10)C7—C6—N1—Hg17.5 (10)
C2—C3—C4—C52.0 (16)C8—C7—N2—C11−2.7 (14)
C3—C4—C5—C6−2.0 (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—Hg1−6.6 (11)
N1—C6—C7—N2−1.0 (12)C10—C11—N2—C71.7 (14)
C5—C6—C7—N2−179.4 (9)C10—C11—N2—Hg1−175.4 (7)
N1—C6—C7—C8177.9 (9)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2551).

References

  • Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306–m1307. [PMC free article] [PubMed]
  • Ahmadi, R., Kalateh, K., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1266. [PMC free article] [PubMed]
  • Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233. [PMC free article] [PubMed]
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, W. T., Wang, M. S., Liu, X., Guo, G. C. & Huang, J. S. (2006). Cryst. Growth Des.6, 2289–2300.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Kalateh, K., Ahmadi, R., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1353–m1354. [PMC free article] [PubMed]
  • Kalateh, K., Ebadi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1397–m1398. [PMC free article] [PubMed]
  • Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211–m1212. [PMC free article] [PubMed]
  • Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848–1854.
  • Liu, Q. D., Wang, R. & Wang, S. (2004). Dalton Trans. pp. 2073–2079. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2005). X-SHAPE and X-RED Stoe & Cie, Darmstadt, Germany.
  • Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305. [PMC free article] [PubMed]
  • Yousefi, M., Khalighi, A., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1284–m1285. [PMC free article] [PubMed]
  • Yousefi, M., Rashidi Vahid, R., Amani, V., Arab Chamjangali, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m1339–m1340. [PMC free article] [PubMed]
  • Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography