[1,3-Bis(2-ethoxy­phen­yl)triazenido]chloridomercury(II)

Mohammad Reza Melardi; Yasaman Salemi; Saba Razi Kazemi; Mohammad Kazem Rofouei

doi:10.1107/S160053680900539X

. 2009 Feb 21;65(Pt 3):m302. doi: 10.1107/S160053680900539X

[1,3-Bis(2-ethoxyphenyl)triazenido]chloridomercury(II)

Mohammad Reza Melardi ^a, Yasaman Salemi ^a, Saba Razi Kazemi ^a, Mohammad Kazem Rofouei ^b,^*

PMCID: PMC2968604 PMID: 21582081

Abstract

In the title compound, [Hg(C₁₆H₁₈N₃O₂)Cl], the Hg^II atom is four-coordinated in a tetrahedral geometry by two N atoms from the 1,3-chelating and one O atom of a 1,3-bis(2-ethoxyphenyl)triazenido ligand and one terminal chloride ion. The dihedral angle between the aromatic rings is 1.72 (14)°. In the crystal C—H⋯π stacking interactions occur.

Related literature

For related structures, see: Rofouei et al. 2008 ▶; Melardi et al. 2007 ▶.

Experimental

Crystal data

[Hg(C₁₆H₁₈N₃O₂)Cl]
M _r = 520.37
Monoclinic,
a = 10.1600 (5) Å
b = 7.3802 (4) Å
c = 22.5655 (11) Å
β = 97.817 (1)°
V = 1676.30 (15) Å³
Z = 4
Mo Kα radiation
μ = 9.35 mm⁻¹
T = 100 K
0.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T _min = 0.280, T _max = 0.479
19713 measured reflections
4451 independent reflections
4009 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.021
wR(F ²) = 0.049
S = 1.01
4451 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −1.19 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900539X/pv2138sup1.cif

e-65-0m302-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900539X/pv2138Isup2.hkl

e-65-0m302-Isup2.hkl^{(218.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1ⁱ	0.95	2.87	3.598 (3)	134
C15—H15B⋯Cg1ⁱⁱ	0.99	2.68	3.511 (3)	142

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C1–C6 ring.

supplementary crystallographic information

Comment

Recently we have reported the synthesis and crystal structure of [1,3-bis(2-methoxyphenyl)triazene with Hg^II as ML₂ structure [Rofouei et al., 2008] and [1,3-bis(2-methoxybenzene)triazene with Hg^II as ML structure [Melardi et al., 2007]. In this article we report the synthesis and crystal structure of the title compound, (I).

In the title compound, the Hg^II atom is four-coordinated in a tetrahedral configuration by two N atoms from the chelating (1,3) and one O atom of ethoxyphenyl triazenido ligand and one terminal Cl atom leading to an asymmetric molecule (Fig. 1). There are interesting C—H···π stacking interactions between CH groups and aromatic phenyl rings with C—H···π distances of 2.869 Å for C3—H3A···Cg1 (5/2 - x, 1/2 + y, 1/2 - z) and 2.681 Å for C15—H15B···Cg1 (2 - x, 1 - y, -z) (Cg1 is centroid of C1—C6 ring) as presented in Fig. 2. The unit cell packing of the title compound showing stacking of molecules is presented at Fig. 3.

Experimental

A solution of [1,3-bis(2-ethoxyphenyl)triazene] (1 mmol, 0.285 g) in acetonitril (10 ml) and triethylamin (0.3 ml) was added to a solution of HgCl₂ (1 mmol, 0.271 g) in methanol (10 ml) yielded the title compound. The suitable crystals for X-ray analysis were obtained from a solution of ethyl acetate after one week. m.p. = 449-451 K.