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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1305.
Published online 2008 September 20. doi:  10.1107/S160053680802953X
PMCID: PMC2959332

(5,5′-Dimethyl-2,2′-bipyridine-κ2 N,N′)diiodidomercury(II)

Abstract

In the mol­ecule of the title compound, [HgI2(C12H12N2)], the HgII atom is four-coordinated in a distorted tetra­hedral configuration by two N atoms from 5,5′-dimethyl-2,2′-bipyridine and two I atoms. There is a π–π contact between pyridine rings of adjacent molecules [centroid–centroid distance = 3.723 (5) Å].

Related literature

For related literature, see: Ahmadi, Kalateh et al. (2008 [triangle]); Ahmadi, Khalighi et al. (2008 [triangle]); Chen et al. (2006 [triangle]); Freire et al. (1999 [triangle]); Htoon & Ladd (1976 [triangle]); Khalighi et al. (2008 [triangle]); Khavasi et al. (2008 [triangle]); Yousefi, Khalighi, et al. (2008 [triangle]); Yousefi, Tadayon Pour et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1305-scheme1.jpg

Experimental

Crystal data

  • [HgI2(C12H12N2)]
  • M r = 638.63
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1305-efi1.jpg
  • a = 15.0325 (8) Å
  • b = 15.0654 (8) Å
  • c = 14.0579 (10) Å
  • V = 3183.7 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 13.53 mm−1
  • T = 298 (2) K
  • 0.35 × 0.31 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005) [triangle]] T min = 0.015, T max = 0.075
  • 23007 measured reflections
  • 4306 independent reflections
  • 3418 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.124
  • S = 1.19
  • 4306 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 1.44 e Å−3
  • Δρmin = −1.51 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. DOI: 10.1107/S160053680802953X/hk2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802953X/hk2531Isup2.hkl

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

Acknowledgments

We 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 et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)2]n, (IV), (Ahmadi, Khalighi et al., 2008), [Cu(5,5'-dcbpy)(en)(H2O)2].2.5H2O, (V), (Yousefi, Khalighi et al., 2008) and {[HgCl(dm4bt)]2(µ-Cl)2}, (VI), (Khavasi et al., 2008) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2' -bipyridine, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-dicarboxylate, en is ethylene- diamine and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are several HgII complexes, with formula, [HgI2(N—N)], such as [HgI2(bipy)], (VII), [HgI2(phen)], (VIII) and [HgI2(2,9-dmphen)], (IX), (Freire et al., 1999), [HgI2(bipy)][HgI2], (X), (Chen et al., 2006), [HgI2(4,4'-dmbpy)], (XI), (Yousefi, Tadayon Pour et al., 2008) and [HgI2(TMDA)], (XII), (Htoon & Ladd, 1976) [where bipy is 2,2'-bipyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthroline, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine and TMDA is tetramethylethylene- diamine] 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, (Fig. 1), the HgII atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 5,5'-dimethyl-2,2'-bi- pyridine and two I atoms. The Hg—I and Hg—N bond lengths and angles (Table 1) are within normal ranges, as in (VII), (VIII) and (XI).

In the crystal structure, the π-π contact (Fig. 2) between the pyridine rings, Cg2···Cg3i [symmetry code: (i) x, 1 - y, 1 - z, where Cg2 and Cg3 are centroids of the rings (N1/C1/C2/C4-C6) and (N2/C7-C10/C12), respectively] may stabilize the structure, with centroid-centroid distance of 3.723 (5) Å.

Experimental

For the preparation of the title compound, (I), a solution of 5,5'-dimethyl -2,2'-bipyridine (0.25 g, 1.33 mmol) in methanol (10 ml) was added to a solution of HgI2 (0.61 g, 1.33 mmol) in methanol (5 ml) at room temperature. The suitable crystals for X-ray analysis were isolated after one week by methanol diffusion to a colorless solution in DMSO (yield; 0.62 g, 72.9%).

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) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
A packing diagram of the title compound.

Crystal data

[HgI2(C12H12N2)]F(000) = 2272
Mr = 638.63Dx = 2.665 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1768 reflections
a = 15.0325 (8) Åθ = 2.4–29.3°
b = 15.0654 (8) ŵ = 13.53 mm1
c = 14.0579 (10) ÅT = 298 K
V = 3183.7 (3) Å3Prism, colorless
Z = 80.35 × 0.31 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer4306 independent reflections
Radiation source: fine-focus sealed tube3418 reflections with I > 2σ(I)
graphiteRint = 0.083
[var phi] and ω scansθmax = 29.3°, θmin = 2.4°
Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED32; Stoe& Cie, 2005)h = −20→19
Tmin = 0.015, Tmax = 0.075k = −20→17
23007 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.19w = 1/[σ2(Fo2) + (0.0347P)2 + 17.4498P] where P = (Fo2 + 2Fc2)/3
4306 reflections(Δ/σ)max = 0.010
154 parametersΔρmax = 1.44 e Å3
0 restraintsΔρmin = −1.51 e Å3

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
Hg10.11964 (2)0.71065 (2)0.60202 (3)0.05197 (12)
I10.00810 (7)0.80915 (5)0.50004 (7)0.0859 (3)
I20.25140 (5)0.76000 (5)0.71769 (6)0.0687 (2)
N10.1696 (4)0.5812 (5)0.5214 (5)0.0403 (14)
N20.0387 (4)0.5836 (4)0.6554 (5)0.0381 (13)
C10.2371 (5)0.5833 (6)0.4598 (6)0.0463 (18)
H10.26330.63770.44600.056*
C20.2697 (6)0.5082 (7)0.4155 (6)0.049 (2)
C30.3485 (8)0.5156 (9)0.3481 (9)0.077 (3)
H3A0.39860.53990.38160.093*
H3B0.33330.55380.29590.093*
H3C0.36350.45780.32430.093*
C40.2299 (7)0.4279 (7)0.4391 (8)0.063 (3)
H40.25060.37550.41210.076*
C50.1604 (7)0.4257 (6)0.5019 (7)0.053 (2)
H50.13240.37230.51620.063*
C60.1322 (5)0.5044 (5)0.5440 (5)0.0387 (16)
C70.0586 (5)0.5057 (5)0.6156 (5)0.0378 (15)
C80.0140 (6)0.4291 (6)0.6412 (7)0.054 (2)
H80.02700.37540.61180.065*
C9−0.0503 (6)0.4341 (6)0.7113 (7)0.054 (2)
H9−0.08050.38290.72970.065*
C10−0.0703 (6)0.5135 (6)0.7542 (6)0.0477 (19)
C11−0.1370 (7)0.5206 (8)0.8337 (8)0.069 (3)
H11A−0.18310.56150.81590.083*
H11B−0.10780.54170.89010.083*
H11C−0.16250.46330.84580.083*
C12−0.0244 (5)0.5873 (6)0.7226 (6)0.0465 (18)
H12−0.03790.64220.74920.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Hg10.0544 (2)0.04113 (17)0.0603 (2)0.00092 (15)0.00422 (17)−0.00082 (14)
I10.0978 (6)0.0521 (4)0.1078 (7)0.0131 (4)−0.0354 (5)0.0050 (4)
I20.0660 (4)0.0555 (4)0.0845 (5)0.0031 (3)−0.0154 (4)−0.0110 (3)
N10.039 (3)0.044 (3)0.037 (3)0.001 (3)0.003 (3)−0.002 (3)
N20.035 (3)0.039 (3)0.041 (3)0.002 (3)0.000 (3)0.001 (3)
C10.040 (4)0.053 (5)0.046 (4)−0.002 (4)0.009 (3)−0.006 (4)
C20.041 (4)0.072 (6)0.035 (4)0.012 (4)0.000 (3)−0.002 (4)
C30.061 (6)0.098 (9)0.073 (7)0.016 (6)0.029 (6)−0.004 (6)
C40.070 (7)0.058 (6)0.062 (6)0.019 (5)0.001 (5)−0.020 (5)
C50.058 (5)0.045 (4)0.056 (5)0.003 (4)0.004 (4)−0.002 (4)
C60.038 (4)0.038 (4)0.040 (4)0.001 (3)−0.004 (3)−0.002 (3)
C70.039 (4)0.040 (4)0.035 (4)0.003 (3)−0.009 (3)−0.001 (3)
C80.057 (5)0.047 (5)0.058 (5)−0.009 (4)−0.004 (4)−0.002 (4)
C90.051 (5)0.051 (5)0.062 (6)−0.016 (4)0.003 (4)0.007 (4)
C100.038 (4)0.057 (5)0.048 (5)−0.001 (4)−0.005 (3)0.010 (4)
C110.059 (6)0.080 (7)0.067 (6)−0.001 (5)0.031 (5)0.000 (5)
C120.042 (4)0.048 (4)0.050 (5)0.003 (4)0.009 (4)−0.003 (4)

Geometric parameters (Å, °)

Hg1—I12.6587 (9)C6—N11.325 (10)
Hg1—I22.6684 (8)C6—C71.496 (11)
Hg1—N12.377 (7)C7—N21.335 (10)
Hg1—N22.389 (6)C7—C81.382 (12)
C1—N11.335 (10)C8—C91.384 (14)
C1—C21.380 (13)C8—H80.9300
C1—H10.9300C9—C101.373 (13)
C2—C41.390 (15)C9—H90.9300
C2—C31.521 (13)C10—C121.382 (12)
C3—H3A0.9600C10—C111.505 (13)
C3—H3B0.9600C11—H11A0.9600
C3—H3C0.9600C11—H11B0.9600
C4—C51.368 (14)C11—H11C0.9600
C4—H40.9300C12—N21.339 (10)
C5—C61.392 (11)C12—H120.9300
C5—H50.9300
I1—Hg1—I2129.89 (3)C4—C5—C6119.1 (9)
N1—Hg1—I1113.59 (16)C4—C5—H5120.5
N1—Hg1—N269.7 (2)C6—C5—H5120.5
N1—Hg1—I2106.53 (16)N1—C6—C5120.9 (8)
N2—Hg1—I1107.15 (15)N1—C6—C7117.6 (7)
N2—Hg1—I2114.22 (15)C5—C6—C7121.5 (7)
C1—N1—Hg1122.0 (6)N2—C7—C8121.1 (8)
C6—N1—Hg1117.9 (5)N2—C7—C6117.4 (7)
C6—N1—C1119.9 (7)C8—C7—C6121.5 (7)
C7—N2—Hg1117.3 (5)C7—C8—C9118.7 (9)
C7—N2—C12119.4 (7)C7—C8—H8120.7
C12—N2—Hg1123.3 (5)C9—C8—H8120.7
N1—C1—C2122.9 (9)C10—C9—C8120.8 (8)
N1—C1—H1118.5C10—C9—H9119.6
C2—C1—H1118.5C8—C9—H9119.6
C1—C2—C4116.9 (8)C9—C10—C12116.8 (8)
C1—C2—C3119.9 (10)C9—C10—C11122.3 (9)
C4—C2—C3123.2 (9)C12—C10—C11120.9 (9)
C2—C3—H3A109.5C10—C11—H11A109.5
C2—C3—H3B109.5C10—C11—H11B109.5
H3A—C3—H3B109.5H11A—C11—H11B109.5
C2—C3—H3C109.5C10—C11—H11C109.5
H3A—C3—H3C109.5H11A—C11—H11C109.5
H3B—C3—H3C109.5H11B—C11—H11C109.5
C5—C4—C2120.3 (9)N2—C12—C10123.2 (8)
C5—C4—H4119.8N2—C12—H12118.4
C2—C4—H4119.8C10—C12—H12118.4
I1—Hg1—N1—C182.9 (6)C5—C6—N1—C1−2.1 (12)
I1—Hg1—N1—C6−101.5 (5)C7—C6—N1—C1178.3 (7)
I2—Hg1—N1—C1−66.4 (6)C5—C6—N1—Hg1−177.8 (6)
I2—Hg1—N1—C6109.2 (5)C7—C6—N1—Hg12.6 (9)
N2—Hg1—N1—C1−176.7 (7)N1—C6—C7—N2−3.3 (11)
N2—Hg1—N1—C6−1.1 (5)C5—C6—C7—N2177.1 (8)
I1—Hg1—N2—C7108.7 (5)N1—C6—C7—C8178.0 (8)
I1—Hg1—N2—C12−71.7 (6)C5—C6—C7—C8−1.6 (12)
I2—Hg1—N2—C7−100.3 (5)C8—C7—N2—C121.4 (12)
I2—Hg1—N2—C1279.3 (6)C6—C7—N2—C12−177.3 (7)
N1—Hg1—N2—C7−0.8 (5)C8—C7—N2—Hg1−179.0 (6)
N1—Hg1—N2—C12178.9 (7)C6—C7—N2—Hg12.3 (9)
C2—C1—N1—C61.5 (13)N2—C7—C8—C9−1.9 (13)
C2—C1—N1—Hg1177.0 (6)C6—C7—C8—C9176.7 (8)
N1—C1—C2—C4−1.1 (13)C7—C8—C9—C100.6 (15)
N1—C1—C2—C3−178.3 (9)C8—C9—C10—C121.2 (14)
C1—C2—C4—C51.4 (14)C8—C9—C10—C11−177.2 (9)
C3—C2—C4—C5178.5 (10)C9—C10—C12—N2−1.8 (13)
C2—C4—C5—C6−2.1 (15)C11—C10—C12—N2176.6 (9)
C4—C5—C6—N12.5 (14)C10—C12—N2—C70.6 (13)
C4—C5—C6—C7−178.0 (8)C10—C12—N2—Hg1−179.1 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2531).

References

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