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

Mohammad Yousefi; Rabin Rashidi Vahid; Vahid Amani; Mansour Arab Chamjangali; Hamid Reza Khavasi

doi:10.1107/S160053680803081X

. 2008 Sep 27;64(Pt 10):m1339–m1340. doi: 10.1107/S160053680803081X

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

Mohammad Yousefi ^a, Rabin Rashidi Vahid ^a, Vahid Amani ^a,^*, Mansour Arab Chamjangali ^b, Hamid Reza Khavasi ^c

PMCID: PMC2959289 PMID: 21201072

Abstract

In the molecule of the title compound, [HgI₂(C₂₄H₁₆N₂)], the Hg^II 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 ▶); Ahmadi, Kalateh, Ebadi et al. (2008 ▶); Ahmadi, Kalateh, Abedi et al. (2008 ▶); Ahmadi, Khalighi et al. (2008 ▶); Khalighi et al. (2008 ▶); Khavasi et al. (2008 ▶); Tadayon Pour et al. (2008 ▶); Yousefi, Khalighi et al. (2008 ▶). For related structures, see: Chen et al. (2006 ▶); Freire et al. (1999 ▶); Htoon & Ladd (1976 ▶); Yousefi, Tadayon Pour et al. (2008 ▶).

Experimental

Crystal data

[HgI₂(C₂₄H₁₆N₂)]
M _r = 786.78
Monoclinic,
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 ▶)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
Δρ_max = 1.49 e Å⁻³
Δρ_min = −1.10 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803081X/hk2540sup1.cif

e-64-m1339-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803081X/hk2540Isup2.hkl

e-64-m1339-Isup2.hkl^{(304.1KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

I1—Hg1	2.6441 (8)
I2—Hg1	2.6555 (9)
N1—Hg1	2.425 (7)
N2—Hg1	2.399 (7)

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N2—Hg1—N1	69.4 (2)
N2—Hg1—I1	104.08 (17)
N1—Hg1—I1	110.65 (19)
N2—Hg1—I2	107.53 (17)
N1—Hg1—I2	103.11 (19)
I1—Hg1—I2	139.97 (3)

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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 Hg^II 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 Hg^II 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%).