[(Z)-1-({3-[(3-Amino­prop­yl)(2-nitro­benz­yl)amino]­prop­yl}imino­meth­yl)naphthalen-2-olato]copper(II) perchlorate

Reza Azadbakht; Hadi Amiri Rudbari; Saeid Menati; Giuseppe Bruno

doi:10.1107/S1600536811045752

. 2011 Nov 12;67(Pt 12):m1748. doi: 10.1107/S1600536811045752

[(Z)-1-({3-[(3-Aminopropyl)(2-nitrobenzyl)amino]propyl}iminomethyl)naphthalen-2-olato]copper(II) perchlorate

Reza Azadbakht ^a,^*, Hadi Amiri Rudbari ^b, Saeid Menati ^c, Giuseppe Bruno ^b

PMCID: PMC3238655 PMID: 22199546

Abstract

In the title compound, [Cu(C₂₄H₂₇N₄O₃)]ClO₄, the Cu^II atom has a distorted square-planar coordination geometry and is surrounded by an N₃O donor set composed of a secondary amine N, a primary amine H, an imino N and a naphthalen-2-olate O atom. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are held together by intermolecular N—H⋯O hydrogen bonds, leading to the formation of a three-dimensional network.

Related literature

For related structures, see: Atkins et al. (1993 ▶); Matsumoto et al. (1989 ▶); Plieger et al. (2004 ▶); Vigato et al. (2007 ▶).

Experimental

Crystal data

[Cu(C₂₄H₂₇N₄O₃)]ClO₄
M _r = 582.50
Monoclinic,
a = 8.1062 (4) Å
b = 19.2907 (8) Å
c = 16.0959 (7) Å
β = 102.072 (2)°
V = 2461.32 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 296 K
0.51 × 0.49 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.706, T _max = 0.747
101979 measured reflections
5377 independent reflections
4605 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.117
S = 1.02
5377 reflections
342 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.52 e Å⁻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: XPW (Siemens, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045752/rk2297sup1.cif

e-67-m1748-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045752/rk2297Isup2.hkl

e-67-m1748-Isup2.hkl^{(258KB, 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
N1—H1⋯O3	0.82 (4)	2.46 (3)	2.948 (4)	119 (3)
N1—H2⋯O4	0.84 (3)	2.39 (4)	3.203 (5)	163 (3)
N1—H2⋯O5	0.84 (3)	2.82 (3)	3.249 (4)	114 (3)
N1—H1⋯O2ⁱ	0.82 (4)	2.51 (3)	3.031 (3)	122 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to Payame Noor University (PNU) for financial support.

supplementary crystallographic information

Comment

Schiff bases have attracted increasing interest owing to their role in the understanding of molecular processes occurring in biochemistry, material science, catalysis, encapsulation, activation, transport and separation phenomena, hydrometallurgy, etc. (Vigato et al., 2007). We report here the crystal structure of the title compound, Cu(C₂₄H₂₇N₄O₃)×ClO₄ consists of discrete [Cu(L)]⁺ cations and perchlorate anions. The closest distance between Cu and O5 of ClO₄ is 3.039 (1)Å that implies a weak coordination of oxygen to copper. The molecular structure of title compound is shown in Fig. 1. The organic ligand, L, coordinates in a tetradentate manner via three nitrogen atoms and one oxygen atom, providing a distorted square–planar arrangement about copper. The two trans angles at the Cu^II atom are about 151.48 (8)° and 158.55 (11)° and the other angles subtended at the Cu^II atom are close to 90°, varying from 86.12 (9)° to 99.07 (9)°. The sum of the angles subtended by the donor atoms at Cu is 369.75°.

Experimental

A solution of NaOH (1.5 mmol) in methanol (10 cm³) was added to a suspension of the appropriate N-(2-nitrobenzyl)-N-(3-aminopropyl)-propane-1,3- diaminetrishydrochloride (0.5 mmol) in methanol (10 cm³). The mixture was stirred at room temperature for a few minutes then filtered, and the precipitate was washed well with methanol (10 cm³). The washings and the filtrate were combined and to this solution, copper perchlorate (0.5 mmol) and 2-hydroxy-1-naphthaldehyde (0.5 mmol) in methanol (50 cm³), was added. The reaction was carried out for 6 h at room temperature. The solution volume was then reduced to 10 cm³ by roto–evaporation and a precipitate formed on addition of a small amount of diethyl ether, which was filtered off, washed with ether, and dried under vacuo.