trans-Bis[1,3-bis­(2-methoxy­phen­yl)triazenido]dimethano­lcadmium(II)

Mohammad Kazem Rofouei; Mohammad Reza Melardi; Hamid Reza Khalili Ghaydari; Mohammad Barkhi

doi:10.1107/S160053680900676X

. 2009 Feb 28;65(Pt 3):m351. doi: 10.1107/S160053680900676X

trans-Bis[1,3-bis(2-methoxyphenyl)triazenido]dimethanolcadmium(II)

Mohammad Kazem Rofouei ^a,^*, Mohammad Reza Melardi ^b, Hamid Reza Khalili Ghaydari ^b, Mohammad Barkhi ^b

PMCID: PMC2968540 PMID: 21582114

Abstract

In the title compound, [Cd(C₁₄H₁₄N₃O₂)₂(CH₃OH)₂], each cadmium(II) center is six-coordinated by an N atom and an O atom of two 1,3-bis(2-methoxyphenyl)triazene ligands and by the O atoms of two methanol molecules. The distorted octahedral coordination geometry of the Cd atom has two N and two O atoms in the equatorial plane, and two O atoms in axial positions. The complex is stabilized by intramolecular O—H⋯O and O—H⋯N hydrogen bonds. In the crystal structure the complexes are linked into chains via intermolecular C—H⋯π stacking interactions. One of the methanol C atoms is disordered with ouccupancies of 0.7:0.3.

Related literature

For complexes of the title ligand, see: Payehghadr et al. (2006 ▶); Rofouei, Shamsipur et al. (2006 ▶); Rofouei, Melardi et al. (2008 ▶); Rofouei & Hashempur (2008 ▶).

Experimental

Crystal data

[Cd(C₁₄H₁₄N₃O₂)₂(CH₄O)₂]
M _r = 689.05
Orthorhombic,
a = 11.0333 (10) Å
b = 13.1892 (12) Å
c = 21.4784 (17) Å
V = 3125.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 100 K
0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.693, T _max = 0.806
40482 measured reflections
9074 independent reflections
8503 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.132
S = 1.07
9074 reflections
394 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 2.65 e Å⁻³
Δρ_min = −2.09 e Å⁻³
Absolute structure: Flack (1983 ▶), 4009 Friedel pairs
Flack parameter: 0.04 (3)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S160053680900676X/su2094sup1.cif

e-65-0m351-sup1.cif^{(29.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900676X/su2094Isup2.hkl

e-65-0m351-Isup2.hkl^{(443.8KB, 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
O5—H5O⋯N3	0.91	1.88	2.710 (6)	150
O6—H6O⋯O4	0.86	1.92	2.739 (5)	157
C23—H23A⋯Cg1ⁱ	0.95	2.82	3.655 (6)	147

Open in a new tab

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

supplementary crystallographic information

Comment

Recently, we have reported on the crystal structures of silver(I), copper(I), and mercry(II) complexes of the ligand [1,3-di(2-methoxy)benzene]triazene (Payehghadr et al., 2006; Rofouei & Hashempur 2008; Rofouei, Melardi et al., 2008). Here we report on the crystal structure of the cadmium(II) complex of the same ligand.

The molecular structure of the title complex is illustrated in Fig. 1. A view along the a axis of the crystal packing is given in Fig. 2. The title complex crystallizes in the non-centrosymmetric space group P2₁2₁2₁; the Flack X factor is 0.04 (3). Each cadmium(II) center is six-coordinated by an N-atom and an O-atom of two [1,3-di(2-methoxy)benzene]triazene ligands, and by the O-atom of two molecules of methanol. The octahedral coordination geometry of the cadmium atom has two N- and two O-atoms in the equatorial plane, and two O-atoms in axial positions. The Cd—N and Cd—O bond lengths are in the expected range for such coordination bonds.

The complex is stabilized by intramolecular O—H···O and O—H···N hydrogen bonds (Table 1). Another noticeable feature of the title compound is the presence of C—H···π stacking interactions (Fig. 3 and Table 1).

Experimental

The synthesis of the ligand 1,3-bis(2-methoxybenzene)triazene has been reported previously (Rofouei, Shamsipur et al., 2006). For the preparation of the cadmium(II) complex a solution of cadmium acetate monohydrate (248 mg, 1 mmol) in methanol (10 ml) was carefully added to a solution of 1,3-bis(2-methoxybenzene)triazene, (514 mg, 2 mmol) in dichloromethane (20 ml) with stirring at 40 °C. The solution was then cooled to rt and after several days needle-like red crystals of the title compound were isolated (yield; 550 mg, 80%).