(2-{[2-(2-Amino­ethyl­amino)­ethyl­imino]­meth­yl}phenolato-κ4 O,N′,N′′,N′′′)copper(II) perchlorate

Moussa Dieng; Aliou Hamady Barry; Mohamed Gaye; Abdou Salam Sall; Paulo Pérez-Lourido; Laura Valencia-Matarranz

doi:10.1107/S1600536811020095

. 2011 Jun 4;67(Pt 7):m830–m831. doi: 10.1107/S1600536811020095

(2-{[2-(2-Aminoethylamino)ethylimino]methyl}phenolato-κ⁴ O,N′,N′′,N′′′)copper(II) perchlorate

Moussa Dieng ^a, Aliou Hamady Barry ^b, Mohamed Gaye ^a,^*, Abdou Salam Sall ^a, Paulo Pérez-Lourido ^c, Laura Valencia-Matarranz ^c

PMCID: PMC3152086 PMID: 21836840

Abstract

The asymmetric unit of the title complex, [Cu(C₁₁H₁₆N₃O)]ClO₄, consists of two Cu^II ions coordinated by Schiff base ligands and two perchlorate anions. The Schiff base molecules are linked to the Cu^II atoms via three N atoms and one O atom, resulting in a square-planar geometry. Intermolecular hydrogen bonds involving the NH groups as donors and O atoms of the perchlorate anions as acceptors are observed.

Related literature

For related structures, see: Ambrosi et al. (2003 ▶); Jiang et al. (2009 ▶).

Experimental

Crystal data

[Cu(C₁₁H₁₆N₃O)]ClO₄
M _r = 369.26
Triclinic,
a = 10.371 (3) Å
b = 12.615 (3) Å
c = 13.390 (3) Å
α = 108.240 (4)°
β = 105.568 (4)°
γ = 108.154 (4)°
V = 1445.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 293 K
0.14 × 0.12 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
9604 measured reflections
4979 independent reflections
4043 reflections with I > 2σ(I)
R _int = 0.024
2 standard reflections every 167 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.131
S = 1.04
4979 reflections
403 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) ▶; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020095/aa2008sup1.cif

e-67-0m830-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020095/aa2008Isup2.hkl

e-67-0m830-Isup2.hkl^{(238.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—O2	1.891 (3)
Cu1—N6	1.933 (4)
Cu1—N5	2.005 (4)
Cu1—N4	2.006 (4)
Cu2—O1	1.895 (3)
Cu2—N3	1.930 (3)
Cu2—N2	2.010 (4)
Cu2—N1	2.012 (3)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3Pⁱ	0.85 (2)	2.52 (3)	3.188 (5)	136 (4)
N1—H1⋯O3P	0.85 (2)	2.54 (3)	3.208 (5)	136 (4)
N2—H2⋯O9Pⁱⁱ	0.85 (2)	2.30 (3)	3.069 (6)	151 (4)
N2—H3⋯O2	0.86 (2)	2.12 (2)	2.955 (5)	162 (4)
N4—H4⋯O8P	0.86 (2)	2.46 (3)	3.223 (7)	148 (3)
N4—H5⋯O1	0.86 (2)	2.24 (2)	3.084 (5)	168 (4)
N5—H6⋯O6Pⁱⁱⁱ	0.84 (2)	2.47 (4)	3.081 (5)	131 (4)
N5—H6⋯O4P	0.84 (2)	2.51 (3)	3.195 (5)	139 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank the Agence Universitaire de la Francophonie for financial support (AUF-PSCI No. 6314PS804).

supplementary crystallographic information

Comment

The asymmetric unit of the title complex, [C₁₁H₁₆N₃ClO₅Cu]₂, consists of two Cu^II ions coordinated with Schiff base ligands and two perclorate anions. The Schiff base molecules are linked to the Cu^II atoms via three N atoms and one O atom. Each Shiff base ligand exhibits a square-planar geometry about the copper(II) ion. Intermolecular hydrogen bonds involving the NH groups as donors and O atoms as acceptors are observed. The Cu–O distances are 1.891 (3) and 1.895 (3) A° while the Cu–N are in the range 1.930 (3)- 2.011 (3) A ° . These values are lower than those observed for the copper complex obtained from the ligand 4-chloro-6-hydroxymethyl-2-((3-aminopropylimino)methyl)phenol (Jiang et al. , 2009). The sum of the angles around the Cu1 atom is 359.56° and around Cu2 atom the sum is 360.3°. These facts indicate that there are very slight distortions from the square planar geometry around the Cu^II atom. In the two molecules the atoms around Cu are situated in the same plane (dihedral angles N2—Cu1—N1—C8 = 178.4 (3)°, N2—Cu1—N1—C8 =-178.4 (3)° , N5—Cu2—N4—C18 = 178.9 (4)° and O2—Cu2—N4—C19 =-177.4 (3)° ). The structure of the complex is shown at Fig. 1. Intermolecular hydrogen bonding network is shown at Fig. 2.

Experimental

Diethylentriamine (1.0311 g, 10 mmol) and salicylaldehyde (2.4408 g, 20 mmol) were dissolved in 20 ml of ethanol with few drops of glacial acetic acid. The mixture was refluxed for 3 h. On cooling a yellow oil was isolated. In a round bottomed flask, copper perclhorate (0.5249, 2 mmol) dissoveld in 10 ml of methanol was introduced. The resulting ligand (0.4145 g, 2 mmol) dissolved in 10 ml of methanol was added. Immediate color change was observed indicating instant formation of the complex. The mixture was stirred at room tempearture for two hours. The blue solution was filtered off and the filtrate was letf at room temperature. After one month, suitable blue crystals for X-ray analysis were obtained. Yield: 70%. Anal. Calc. for [C₁₁H₁₆N₃ClO₅Cu]₂ (%): C, 35.78; H, 4.37; N, 11.38. Found: C, 35.80; H, 4.35; N, 11.34. Selected IR data (cm^-1, KBr pellet): 3216, 1637, 1600, 1582, 1197, 764.