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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1339–m1340.
Published online 2008 September 27. doi:  10.1107/S160053680803081X
PMCID: PMC2959289

(4,7-Diphenyl-1,10-phenanthroline-κ2 N,N′)diiodidomercury(II)

Abstract

In the mol­ecule of the title compound, [HgI2(C24H16N2)], the HgII atom is four-coordinated in a distorted tetra­hedral configuration by two N atoms from the bidentate 4,7-diphenyl-1,10-phenanthroline and two iodide ligands. There is a π–π contact between the pyridine and phenyl rings [centroid-to-centroid distance = 4.2387 (4) Å].

Related literature

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

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Object name is e-64-m1339-scheme1.jpg

Experimental

Crystal data

  • [HgI2(C24H16N2)]
  • M r = 786.78
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1339-efi1.jpg
  • a = 16.673 (3) Å
  • b = 8.8964 (18) Å
  • c = 16.823 (3) Å
  • β = 109.26 (3)°
  • V = 2355.7 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 9.17 mm−1
  • T = 298 (2) K
  • 0.50 × 0.48 × 0.28 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005 [triangle])T min = 0.016, T max = 0.080
  • 19129 measured reflections
  • 6340 independent reflections
  • 5356 reflections with I > 2σ(I)
  • R int = 0.094

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.183
  • S = 1.23
  • 6340 reflections
  • 263 parameters
  • H-atom parameters constrained
  • Δρmax = 1.49 e Å−3
  • Δρmin = −1.10 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/S160053680803081X/hk2540sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803081X/hk2540Isup2.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, Abedi et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)2]n, (IV), (Ahmadi, Khalighi et al., 2008), [Hg(5,5'-dmbpy)I2], (V), (Tadayon Pour et al., 2008), [In(4,4'-dmbpy)Cl3(DMSO)], (VI), (Ahmadi, Kalateh, Ebadi et al., 2008), [Cu(5,5'-dcbpy)(en)(H2O)2].2.5H2O, (VII), (Yousefi, Khalighi et al., 2008), [Au(dmphen)Cl2][AuCl4], (VIII), (Ahmadi, Amani et al., 2008), and {[HgCl(dm4bt)]2(µ-Cl)2}, (IX), (Khavasi 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'-bi- pyridine, DMSO is dimethyl sulfoxide, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-di- carboxylate, en is ethylenediamine, dmphen is 4,7-diphenyl-1,10- phenanthroline and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are several HgII complexes, with formula, [HgI2(N—N)], such as [HgI2(bipy)], (X), [HgI2(phen)], (XI) and [HgI2(2,9-dmphen)], (XII), (Freire et al., 1999), [HgI2(bipy)][HgI2], (XIII), (Chen et al., 2006), [HgI2(4,4'-dmbpy)], (XIV), (Yousefi, Tadayon Pour et al., 2008) and [HgI2(TMDA)], (XV), (Htoon & Ladd, 1976) [where bipy is 2,2'-bipyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthroline and TMDA is tetramethylethylenediamine] 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 4,7-diphenyl-1,10-phenanthroline and two I atoms. The Hg—I and Hg—N bond lengths and angles (Table 1) are within normal ranges, as in (X), (XI) and (XIV).

In the crystal structure, the π–π contact (Fig. 2) between the pyridine and phenyl rings, Cg3···Cg4i [symmetry code: (i) 3/2 - x, -1/2 + y, 1/2 - z, where Cg3 and Cg4 are centroids of the rings (N1/C1–C3/C10/C24) and (C4–C9), respectively] may stabilize the structure, with centroid–centroid distance of 4.2387 (4) Å.

Experimental

For the preparation of the title compound, a solution of 4,7-diphenyl-1,10-phenanthroline (0.36 g, 1.10 mmol) in acetonitrile (20 ml) was added to a solution of HgI2 (0.50 g, 1.10 mmol) in methanol (20 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield; 0.62 g, 71.6%).

Refinement

H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H 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 partial packing diagram of the title compound.

Crystal data

[HgI2(C24H16N2)]F(000) = 1440
Mr = 786.78Dx = 2.218 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2356 reflections
a = 16.673 (3) Åθ = 2.1–29.3°
b = 8.8964 (18) ŵ = 9.17 mm1
c = 16.823 (3) ÅT = 298 K
β = 109.26 (3)°Block, colourless
V = 2355.7 (9) Å30.50 × 0.48 × 0.28 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer6340 independent reflections
Radiation source: fine-focus sealed tube5356 reflections with I > 2σ(I)
graphiteRint = 0.094
[var phi] and ω scansθmax = 29.3°, θmin = 2.1°
Absorption correction: numerical shape of crystal determined opticallyh = −22→19
Tmin = 0.016, Tmax = 0.080k = −12→12
19129 measured reflectionsl = −22→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.183w = 1/[σ2(Fo2) + (0.085P)2 + 4.523P] where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max = 0.009
6340 reflectionsΔρmax = 1.49 e Å3
263 parametersΔρmin = −1.11 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: 0.0086 (6)

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
Hg10.35746 (2)0.27882 (4)0.10505 (2)0.05561 (16)
I10.29465 (5)0.55290 (7)0.06892 (4)0.0694 (2)
I20.32177 (5)−0.00283 (7)0.05316 (5)0.0736 (2)
N10.5115 (5)0.2845 (9)0.1529 (4)0.0545 (17)
N20.4136 (4)0.2750 (8)0.2559 (5)0.0495 (14)
C10.5583 (7)0.2946 (13)0.1039 (6)0.065 (2)
H10.53140.30980.04660.078*
C20.6448 (7)0.2837 (13)0.1335 (6)0.068 (3)
H20.67490.29300.09600.081*
C30.6884 (6)0.2594 (10)0.2172 (6)0.0524 (18)
C40.7831 (6)0.2515 (11)0.2502 (7)0.0550 (19)
C50.8260 (8)0.1623 (13)0.2086 (9)0.076 (3)
H50.79630.11180.15920.091*
C60.9151 (9)0.1506 (14)0.2430 (12)0.101 (5)
H60.94420.08690.21820.122*
C70.9601 (9)0.2342 (18)0.3143 (12)0.093 (4)
H71.01900.22740.33620.112*
C80.9178 (7)0.3244 (19)0.3510 (9)0.086 (3)
H80.94770.38150.39760.103*
C90.8304 (6)0.3327 (15)0.3199 (7)0.068 (2)
H90.80240.39480.34670.082*
C100.6399 (5)0.2429 (10)0.2719 (5)0.0487 (16)
C110.6750 (5)0.2082 (11)0.3592 (6)0.0545 (19)
H110.73240.18430.38160.065*
C120.6274 (5)0.2090 (11)0.4100 (5)0.0534 (19)
H120.65270.18550.46670.064*
C130.5399 (5)0.2448 (8)0.3793 (5)0.0411 (14)
C140.4883 (5)0.2524 (9)0.4320 (5)0.0456 (15)
C150.5272 (6)0.2456 (9)0.5252 (5)0.0478 (16)
C160.5965 (6)0.3362 (12)0.5672 (5)0.059 (2)
H160.61760.40410.53700.071*
C170.6343 (7)0.3255 (15)0.6545 (6)0.071 (3)
H170.67980.38750.68240.085*
C180.6042 (9)0.2228 (14)0.6993 (7)0.078 (3)
H180.63000.21400.75730.094*
C190.5350 (9)0.1323 (12)0.6573 (7)0.078 (3)
H190.51500.06220.68730.093*
C200.4958 (8)0.1460 (11)0.5713 (6)0.062 (2)
H200.44820.08810.54410.075*
C210.4019 (6)0.2684 (11)0.3937 (6)0.058 (2)
H210.36640.27430.42610.069*
C220.3682 (5)0.2756 (11)0.3070 (6)0.058 (2)
H220.30940.28140.28300.070*
C230.5005 (5)0.2597 (8)0.2918 (5)0.0420 (14)
C240.5506 (5)0.2610 (9)0.2361 (5)0.0463 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Hg10.0541 (2)0.0529 (2)0.0461 (2)0.00215 (13)−0.00194 (13)0.00031 (12)
I10.0728 (4)0.0484 (3)0.0684 (4)0.0027 (3)−0.0018 (3)−0.0002 (3)
I20.0846 (5)0.0496 (3)0.0714 (4)0.0056 (3)0.0051 (3)−0.0066 (3)
N10.049 (3)0.072 (5)0.036 (3)−0.006 (3)0.006 (3)−0.002 (3)
N20.041 (3)0.054 (4)0.047 (3)0.001 (3)0.006 (3)0.001 (3)
C10.071 (6)0.084 (7)0.037 (4)−0.001 (5)0.012 (4)0.006 (4)
C20.066 (6)0.093 (8)0.051 (5)−0.011 (5)0.028 (4)−0.006 (5)
C30.052 (4)0.057 (4)0.052 (4)−0.005 (4)0.022 (4)−0.006 (4)
C40.051 (4)0.055 (4)0.066 (5)0.000 (3)0.029 (4)0.000 (4)
C50.080 (7)0.059 (5)0.104 (8)−0.012 (5)0.051 (6)−0.017 (6)
C60.086 (8)0.065 (6)0.188 (16)0.005 (6)0.093 (10)0.005 (9)
C70.060 (6)0.107 (10)0.113 (11)0.008 (7)0.028 (7)0.028 (9)
C80.057 (5)0.111 (10)0.085 (8)−0.001 (7)0.017 (5)0.003 (8)
C90.047 (4)0.085 (7)0.069 (6)−0.001 (5)0.015 (4)−0.006 (5)
C100.042 (3)0.052 (4)0.048 (4)−0.004 (3)0.010 (3)−0.002 (3)
C110.038 (3)0.073 (6)0.049 (4)0.005 (3)0.009 (3)0.010 (4)
C120.045 (4)0.071 (5)0.037 (3)0.002 (4)0.004 (3)0.007 (3)
C130.040 (3)0.045 (3)0.037 (3)−0.004 (3)0.011 (3)0.006 (3)
C140.049 (4)0.047 (3)0.041 (3)−0.001 (3)0.015 (3)0.002 (3)
C150.057 (4)0.047 (4)0.040 (4)0.000 (3)0.016 (3)−0.004 (3)
C160.063 (5)0.063 (5)0.048 (4)−0.011 (4)0.013 (4)−0.001 (4)
C170.074 (6)0.079 (6)0.050 (5)−0.003 (5)0.005 (4)−0.019 (5)
C180.104 (9)0.087 (8)0.040 (4)0.004 (7)0.021 (5)0.001 (5)
C190.128 (10)0.060 (5)0.058 (5)−0.010 (6)0.048 (6)−0.008 (5)
C200.091 (7)0.051 (4)0.052 (4)−0.006 (4)0.033 (4)−0.004 (4)
C210.050 (4)0.070 (5)0.057 (5)0.000 (4)0.022 (4)−0.003 (4)
C220.039 (4)0.072 (6)0.057 (5)−0.006 (4)0.008 (3)−0.003 (4)
C230.040 (3)0.042 (3)0.040 (3)−0.001 (3)0.007 (3)−0.001 (3)
C240.047 (4)0.044 (3)0.039 (3)−0.002 (3)0.003 (3)0.007 (3)

Geometric parameters (Å, °)

I1—Hg12.6441 (8)C11—H110.9300
I2—Hg12.6555 (9)C12—C131.415 (11)
N1—Hg12.425 (7)C12—H120.9300
N2—Hg12.399 (7)C13—C231.407 (10)
C1—N11.312 (12)C13—C141.426 (10)
C1—C21.364 (15)C14—C211.379 (12)
C1—H10.9300C14—C151.487 (11)
C2—C31.372 (14)C15—C201.389 (12)
C2—H20.9300C15—C161.394 (12)
C3—C101.420 (12)C16—C171.398 (13)
C3—C41.493 (13)C16—H160.9300
C4—C91.382 (15)C17—C181.380 (18)
C4—C51.401 (14)C17—H170.9300
C5—C61.409 (19)C18—C191.393 (18)
C5—H50.9300C18—H180.9300
C6—C71.40 (2)C19—C201.383 (15)
C6—H60.9300C19—H190.9300
C7—C81.34 (2)C20—H200.9300
C7—H70.9300C21—C221.381 (14)
C8—C91.378 (15)C21—H210.9300
C8—H80.9300C22—N21.320 (12)
C9—H90.9300C22—H220.9300
C10—C241.419 (11)C23—N21.379 (10)
C10—C111.423 (12)C23—C241.447 (11)
C11—C121.345 (13)C24—N11.352 (10)
N2—Hg1—N169.4 (2)C12—C11—C10121.7 (8)
N2—Hg1—I1104.08 (17)C12—C11—H11119.1
N1—Hg1—I1110.65 (19)C10—C11—H11119.1
N2—Hg1—I2107.53 (17)C11—C12—C13121.5 (7)
N1—Hg1—I2103.11 (19)C11—C12—H12119.2
I1—Hg1—I2139.97 (3)C13—C12—H12119.2
C1—N1—C24118.5 (8)C23—C13—C12118.2 (7)
C1—N1—Hg1125.3 (6)C23—C13—C14118.5 (7)
C24—N1—Hg1115.9 (6)C12—C13—C14123.0 (7)
C22—N2—C23117.4 (7)C21—C14—C13117.8 (7)
C22—N2—Hg1125.6 (6)C21—C14—C15121.5 (7)
C23—N2—Hg1116.8 (5)C13—C14—C15120.7 (7)
N1—C1—C2122.9 (8)C20—C15—C16119.2 (8)
N1—C1—H1118.6C20—C15—C14120.0 (8)
C2—C1—H1118.6C16—C15—C14120.8 (8)
C1—C2—C3121.6 (8)C15—C16—C17120.3 (9)
C1—C2—H2119.2C15—C16—H16119.8
C3—C2—H2119.2C17—C16—H16119.8
C2—C3—C10117.4 (8)C18—C17—C16120.0 (11)
C2—C3—C4121.8 (8)C18—C17—H17120.0
C10—C3—C4120.8 (8)C16—C17—H17120.0
C9—C4—C5118.6 (9)C17—C18—C19119.7 (10)
C9—C4—C3121.9 (8)C17—C18—H18120.2
C5—C4—C3119.5 (9)C19—C18—H18120.2
C4—C5—C6118.6 (12)C20—C19—C18120.4 (10)
C4—C5—H5120.7C20—C19—H19119.8
C6—C5—H5120.7C18—C19—H19119.8
C7—C6—C5120.5 (11)C19—C20—C15120.3 (10)
C7—C6—H6119.8C19—C20—H20119.8
C5—C6—H6119.8C15—C20—H20119.8
C8—C7—C6119.7 (12)C14—C21—C22119.8 (8)
C8—C7—H7120.1C14—C21—H21120.1
C6—C7—H7120.1C22—C21—H21120.1
C7—C8—C9120.5 (14)N2—C22—C21124.5 (8)
C7—C8—H8119.8N2—C22—H22117.7
C9—C8—H8119.8C21—C22—H22117.7
C8—C9—C4122.0 (11)N2—C23—C13121.9 (7)
C8—C9—H9119.0N2—C23—C24117.6 (7)
C4—C9—H9119.0C13—C23—C24120.5 (7)
C24—C10—C3117.0 (8)N1—C24—C10122.6 (8)
C24—C10—C11118.7 (7)N1—C24—C23119.2 (7)
C3—C10—C11124.2 (8)C10—C24—C23118.2 (7)
C1—N1—Hg1—N2−177.4 (9)C21—C14—C15—C2051.1 (12)
C24—N1—Hg1—N29.2 (6)C13—C14—C15—C20−129.9 (9)
C1—N1—Hg1—I1−79.6 (9)C21—C14—C15—C16−130.2 (10)
C24—N1—Hg1—I1107.0 (6)C13—C14—C15—C1648.7 (12)
C1—N1—Hg1—I278.6 (9)C20—C15—C16—C170.7 (15)
C24—N1—Hg1—I2−94.9 (6)C14—C15—C16—C17−177.9 (9)
C22—N2—Hg1—N1177.5 (8)C15—C16—C17—C181.3 (17)
C23—N2—Hg1—N1−7.5 (5)C16—C17—C18—C19−1.3 (19)
C22—N2—Hg1—I170.4 (8)C17—C18—C19—C20−0.7 (19)
C23—N2—Hg1—I1−114.6 (5)C18—C19—C20—C152.8 (17)
C22—N2—Hg1—I2−84.7 (7)C16—C15—C20—C19−2.7 (15)
C23—N2—Hg1—I290.3 (6)C14—C15—C20—C19175.9 (9)
N1—C1—C2—C30.8 (19)C13—C14—C21—C220.4 (14)
C1—C2—C3—C101.2 (16)C15—C14—C21—C22179.4 (9)
C1—C2—C3—C4−178.3 (10)C14—C21—C22—N2−3.1 (16)
C2—C3—C4—C9130.8 (11)C12—C13—C23—N2171.4 (8)
C10—C3—C4—C9−48.7 (14)C14—C13—C23—N2−2.7 (11)
C2—C3—C4—C5−47.7 (14)C12—C13—C23—C24−9.3 (11)
C10—C3—C4—C5132.8 (10)C14—C13—C23—C24176.6 (7)
C9—C4—C5—C64.5 (17)C3—C10—C24—N13.7 (13)
C3—C4—C5—C6−177.0 (10)C11—C10—C24—N1−175.7 (8)
C4—C5—C6—C7−4(2)C3—C10—C24—C23−174.0 (7)
C5—C6—C7—C81(2)C11—C10—C24—C236.7 (12)
C6—C7—C8—C91(2)N2—C23—C24—N13.3 (11)
C7—C8—C9—C4−1(2)C13—C23—C24—N1−176.0 (7)
C5—C4—C9—C8−2.2 (18)N2—C23—C24—C10−179.0 (7)
C3—C4—C9—C8179.3 (12)C13—C23—C24—C101.7 (11)
C2—C3—C10—C24−3.3 (13)C21—C22—N2—C232.8 (14)
C4—C3—C10—C24176.3 (8)C21—C22—N2—Hg1177.8 (7)
C2—C3—C10—C11176.0 (9)C13—C23—N2—C220.2 (12)
C4—C3—C10—C11−4.4 (14)C24—C23—N2—C22−179.2 (8)
C24—C10—C11—C12−7.6 (14)C13—C23—N2—Hg1−175.2 (6)
C3—C10—C11—C12173.1 (9)C24—C23—N2—Hg15.5 (9)
C10—C11—C12—C13−0.1 (15)C2—C1—N1—C24−0.6 (16)
C11—C12—C13—C238.6 (13)C2—C1—N1—Hg1−173.9 (9)
C11—C12—C13—C14−177.5 (9)C10—C24—N1—C1−1.7 (14)
C23—C13—C14—C212.3 (12)C23—C24—N1—C1175.9 (9)
C12—C13—C14—C21−171.5 (8)C10—C24—N1—Hg1172.2 (6)
C23—C13—C14—C15−176.7 (7)C23—C24—N1—Hg1−10.2 (10)
C12—C13—C14—C159.5 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2540).

References

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