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

Azadbakht, R.; Amiri Rudbari, H.; Menati, S.; Bruno, G.

doi:10.1107/S1600536811045752

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1748

https://doi.org/10.1107/S1600536811045752

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[(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 and Giuseppe Bruno ^b

^aDepartment of Chemistry, Payame Noor University, Hamedan, Iran, ^bDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Universita di Messina 98166 Messina, Italy, and ^cDepartment of Chemistry, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran
^*Correspondence e-mail: r_azadbakht@yahoo.com

(Received 21 August 2011; accepted 31 October 2011; online 12 November 2011)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.039
wR(F²) = 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

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)
Symmetry code: (i) -x+1, -y+2, -z+1.

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045752/rk2297sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045752/rk2297Isup2.hkl

checkCIF report

Comment top

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°.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. Perspective view of the title molecule with numbering of the atoms. Displacement ellipsoids are drawn at 30% probability level. The H atoms are shown as small spheres of arbitrary radius. The H2 atom is overlapped by N1 ellipsoid.

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

Crystal data top

[Cu(C₂₄H₂₇N₄O₃)]ClO₄	F(000) = 1204
M_r = 582.50	D_x = 1.572 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9603 reflections
a = 8.1062 (4) Å	θ = 2.6–29.2°
b = 19.2907 (8) Å	µ = 1.05 mm⁻¹
c = 16.0959 (7) Å	T = 296 K
β = 102.072 (2)°	Block, black
V = 2461.32 (19) Å³	0.51 × 0.49 × 0.32 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5377 independent reflections
Radiation source: fine–focus sealed tube	4605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
φ and ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.706, T_max = 0.747	k = −24→24
101979 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0736P)² + 1.1383P] where P = (F_o² + 2F_c²)/3
5377 reflections	(Δ/σ)_max = 0.001
342 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Cu(C₂₄H₂₇N₄O₃)]ClO₄	V = 2461.32 (19) Å³
M_r = 582.50	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1062 (4) Å	µ = 1.05 mm⁻¹
b = 19.2907 (8) Å	T = 296 K
c = 16.0959 (7) Å	0.51 × 0.49 × 0.32 mm
β = 102.072 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5377 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4605 reflections with I > 2σ(I)
T_min = 0.706, T_max = 0.747	R_int = 0.061
101979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.59 e Å⁻³
5377 reflections	Δρ_min = −0.52 e Å⁻³
342 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F², conventional R–factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σF² is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F² are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu	0.32009 (3)	0.856784 (13)	0.361933 (15)	0.03852 (11)
N1	0.4800 (3)	0.84797 (14)	0.47232 (15)	0.0544 (5)
C1	0.6353 (4)	0.80578 (18)	0.4829 (2)	0.0719 (8)
H1A	0.6069	0.7573	0.4879	0.086*
H1B	0.7120	0.8192	0.5351	0.086*
C2	0.7232 (4)	0.81433 (19)	0.4092 (2)	0.0741 (8)
H2A	0.7419	0.8633	0.4013	0.089*
H2B	0.8327	0.7920	0.4236	0.089*
C3	0.6275 (4)	0.78479 (16)	0.3269 (2)	0.0660 (7)
H3A	0.7051	0.7797	0.2889	0.079*
H3B	0.5894	0.7387	0.3380	0.079*
N2	0.4785 (2)	0.82515 (10)	0.28176 (12)	0.0464 (4)
C4	0.3820 (4)	0.78081 (14)	0.21083 (17)	0.0600 (6)
H4A	0.3279	0.8106	0.1645	0.072*
H4B	0.4607	0.7511	0.1897	0.072*
C5	0.2511 (4)	0.73681 (13)	0.23789 (18)	0.0627 (7)
H5A	0.2944	0.7203	0.2952	0.075*
H5B	0.2288	0.6967	0.2009	0.075*
C6	0.0886 (3)	0.77510 (13)	0.23556 (17)	0.0546 (6)
H6A	0.0303	0.7812	0.1769	0.065*
H6B	0.0167	0.7477	0.2640	0.065*
N3	0.1174 (2)	0.84326 (9)	0.27678 (11)	0.0406 (4)
C7	0.0059 (3)	0.89113 (11)	0.25349 (13)	0.0399 (4)
H7	−0.0785	0.8818	0.2061	0.048*
C8	−0.0007 (3)	0.95679 (11)	0.29327 (13)	0.0390 (4)
C17	−0.1169 (3)	1.00936 (11)	0.25241 (14)	0.0407 (4)
C16	−0.2083 (3)	1.00439 (14)	0.16799 (15)	0.0498 (5)
H16	−0.1943	0.9656	0.1358	0.060*
C15	−0.3186 (3)	1.05619 (15)	0.13210 (17)	0.0569 (6)
H15	−0.3781	1.0516	0.0764	0.068*
C14	−0.3413 (3)	1.11485 (15)	0.1783 (2)	0.0608 (7)
H14	−0.4162	1.1492	0.1537	0.073*
C13	−0.2539 (3)	1.12185 (14)	0.25950 (19)	0.0559 (6)
H13	−0.2695	1.1613	0.2902	0.067*
C12	−0.1396 (3)	1.07032 (12)	0.29802 (16)	0.0465 (5)
C11	−0.0439 (3)	1.07871 (13)	0.38245 (17)	0.0535 (6)
H11	−0.0606	1.1180	0.4131	0.064*
C10	0.0696 (3)	1.03129 (13)	0.41882 (15)	0.0514 (5)
H10	0.1313	1.0390	0.4736	0.062*
C9	0.0979 (3)	0.96920 (12)	0.37529 (14)	0.0422 (5)
O1	0.2131 (2)	0.92738 (9)	0.41511 (10)	0.0530 (4)
C18	0.5462 (3)	0.88515 (14)	0.23958 (15)	0.0494 (5)
H18A	0.5944	0.8674	0.1935	0.059*
H18B	0.6367	0.9066	0.2805	0.059*
C19	0.4182 (3)	0.94026 (13)	0.20450 (14)	0.0457 (5)
C24	0.3379 (4)	0.93601 (15)	0.11856 (16)	0.0585 (6)
H24	0.3629	0.8988	0.0866	0.070*
C23	0.2235 (4)	0.98488 (18)	0.07963 (18)	0.0684 (8)
H23	0.1709	0.9796	0.0228	0.082*
C22	0.1872 (4)	1.04122 (17)	0.1245 (2)	0.0702 (8)
H22	0.1095	1.0741	0.0985	0.084*
C21	0.2654 (4)	1.04867 (14)	0.2073 (2)	0.0623 (7)
H21	0.2421	1.0871	0.2378	0.075*
C20	0.3800 (3)	0.99919 (12)	0.24637 (15)	0.0479 (5)
N4	0.4641 (3)	1.01508 (12)	0.33436 (14)	0.0576 (5)
O3	0.5511 (3)	0.97071 (12)	0.37640 (13)	0.0770 (6)
O2	0.4446 (4)	1.07214 (12)	0.36190 (16)	0.0890 (7)
Cl	0.19969 (9)	0.70592 (4)	0.51751 (4)	0.06081 (18)
O4	0.2496 (4)	0.76098 (17)	0.57398 (17)	0.1104 (10)
O5	0.2004 (5)	0.72505 (17)	0.43448 (15)	0.1153 (11)
O6	0.0406 (7)	0.6830 (4)	0.5193 (3)	0.240 (4)
O7	0.3086 (9)	0.6533 (2)	0.5438 (3)	0.216 (3)
H1	0.517 (4)	0.8868 (19)	0.487 (2)	0.068 (10)*
H2	0.419 (4)	0.8333 (18)	0.504 (2)	0.064 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.04088 (16)	0.03732 (16)	0.03504 (15)	0.00157 (9)	0.00268 (11)	−0.00284 (9)
N1	0.0597 (13)	0.0547 (13)	0.0434 (11)	0.0018 (10)	−0.0021 (10)	0.0004 (10)
C1	0.0653 (17)	0.0725 (19)	0.0671 (17)	0.0133 (14)	−0.0109 (14)	0.0159 (14)
C2	0.0511 (15)	0.085 (2)	0.080 (2)	0.0195 (14)	−0.0004 (14)	0.0092 (17)
C3	0.0604 (16)	0.0568 (15)	0.0821 (19)	0.0214 (13)	0.0182 (14)	0.0061 (14)
N2	0.0489 (10)	0.0414 (10)	0.0487 (10)	0.0063 (8)	0.0097 (8)	−0.0082 (8)
C4	0.0767 (17)	0.0516 (14)	0.0525 (14)	0.0014 (12)	0.0156 (12)	−0.0157 (11)
C5	0.0880 (19)	0.0361 (12)	0.0606 (15)	−0.0022 (12)	0.0082 (14)	−0.0118 (11)
C6	0.0595 (14)	0.0393 (12)	0.0583 (14)	−0.0091 (10)	−0.0028 (11)	−0.0071 (10)
N3	0.0423 (9)	0.0380 (9)	0.0398 (9)	−0.0053 (7)	0.0051 (7)	−0.0034 (7)
C7	0.0350 (10)	0.0452 (11)	0.0384 (10)	−0.0032 (8)	0.0054 (8)	0.0007 (8)
C8	0.0372 (10)	0.0418 (11)	0.0399 (10)	−0.0015 (8)	0.0124 (8)	0.0008 (8)
C17	0.0364 (10)	0.0428 (11)	0.0456 (11)	−0.0014 (8)	0.0147 (8)	0.0067 (9)
C16	0.0475 (12)	0.0529 (13)	0.0498 (12)	0.0025 (10)	0.0120 (10)	0.0054 (10)
C15	0.0500 (13)	0.0642 (16)	0.0556 (14)	0.0036 (11)	0.0090 (11)	0.0163 (12)
C14	0.0560 (14)	0.0513 (14)	0.0769 (18)	0.0111 (11)	0.0180 (13)	0.0212 (13)
C13	0.0568 (14)	0.0421 (12)	0.0725 (17)	0.0059 (11)	0.0221 (13)	0.0081 (11)
C12	0.0455 (11)	0.0411 (11)	0.0572 (13)	0.0003 (9)	0.0205 (10)	0.0062 (10)
C11	0.0610 (14)	0.0434 (12)	0.0595 (14)	0.0028 (10)	0.0206 (11)	−0.0075 (10)
C10	0.0573 (13)	0.0536 (14)	0.0444 (12)	0.0003 (11)	0.0132 (10)	−0.0089 (10)
C9	0.0416 (11)	0.0454 (11)	0.0417 (11)	0.0015 (9)	0.0131 (8)	−0.0012 (9)
O1	0.0584 (10)	0.0587 (10)	0.0380 (8)	0.0146 (8)	0.0013 (7)	−0.0091 (7)
C18	0.0466 (12)	0.0594 (14)	0.0459 (12)	0.0032 (10)	0.0183 (10)	−0.0025 (10)
C19	0.0483 (12)	0.0503 (12)	0.0419 (11)	−0.0017 (10)	0.0171 (9)	0.0020 (9)
C24	0.0666 (16)	0.0669 (16)	0.0443 (12)	0.0028 (13)	0.0168 (11)	0.0004 (11)
C23	0.0700 (17)	0.083 (2)	0.0499 (14)	0.0015 (15)	0.0079 (13)	0.0171 (14)
C22	0.0640 (17)	0.0654 (18)	0.083 (2)	0.0069 (13)	0.0186 (15)	0.0270 (16)
C21	0.0673 (16)	0.0453 (13)	0.0804 (19)	0.0004 (12)	0.0294 (14)	0.0091 (13)
C20	0.0533 (12)	0.0439 (12)	0.0516 (12)	−0.0081 (10)	0.0221 (10)	0.0020 (10)
N4	0.0713 (14)	0.0498 (12)	0.0566 (12)	−0.0154 (10)	0.0244 (11)	−0.0069 (10)
O3	0.1088 (17)	0.0651 (13)	0.0520 (11)	−0.0091 (12)	0.0052 (11)	−0.0036 (10)
O2	0.122 (2)	0.0594 (13)	0.0867 (16)	−0.0078 (13)	0.0250 (14)	−0.0305 (12)
Cl	0.0796 (4)	0.0619 (4)	0.0372 (3)	−0.0102 (3)	0.0036 (3)	0.0037 (2)
O4	0.142 (3)	0.103 (2)	0.0761 (16)	0.0126 (18)	−0.0001 (16)	−0.0345 (15)
O5	0.172 (3)	0.122 (2)	0.0487 (12)	−0.050 (2)	0.0170 (15)	0.0102 (13)
O6	0.198 (5)	0.412 (9)	0.109 (3)	−0.198 (6)	0.029 (3)	0.016 (4)
O7	0.366 (8)	0.121 (3)	0.116 (3)	0.115 (4)	−0.054 (4)	−0.030 (2)

Geometric parameters (Å, º) top

Cu—O1	1.9104 (16)	C16—C15	1.384 (3)
Cu—N3	1.9245 (18)	C16—H16	0.9300
Cu—N1	1.976 (2)	C15—C14	1.387 (4)
Cu—N2	2.0925 (19)	C15—H15	0.9300
N1—C1	1.479 (4)	C14—C13	1.357 (4)
N1—H1	0.82 (4)	C14—H14	0.9300
N1—H2	0.84 (3)	C13—C12	1.411 (3)
C1—C2	1.515 (5)	C13—H13	0.9300
C1—H1A	0.9700	C12—C11	1.426 (4)
C1—H1B	0.9700	C11—C10	1.342 (4)
C2—C3	1.500 (5)	C11—H11	0.9300
C2—H2A	0.9700	C10—C9	1.430 (3)
C2—H2B	0.9700	C10—H10	0.9300
C3—N2	1.492 (3)	C9—O1	1.297 (3)
C3—H3A	0.9700	C18—C19	1.510 (3)
C3—H3B	0.9700	C18—H18A	0.9700
N2—C18	1.503 (3)	C18—H18B	0.9700
N2—C4	1.508 (3)	C19—C20	1.389 (3)
C4—C5	1.493 (4)	C19—C24	1.402 (3)
C4—H4A	0.9700	C24—C23	1.378 (4)
C4—H4B	0.9700	C24—H24	0.9300
C5—C6	1.504 (4)	C23—C22	1.371 (5)
C5—H5A	0.9700	C23—H23	0.9300
C5—H5B	0.9700	C22—C21	1.358 (4)
C6—N3	1.469 (3)	C22—H22	0.9300
C6—H6A	0.9700	C21—C20	1.388 (4)
C6—H6B	0.9700	C21—H21	0.9300
N3—C7	1.292 (3)	C20—N4	1.470 (3)
C7—C8	1.425 (3)	N4—O2	1.209 (3)
C7—H7	0.9300	N4—O3	1.220 (3)
C8—C9	1.413 (3)	Cl—O7	1.354 (4)
C8—C17	1.445 (3)	Cl—O6	1.369 (4)
C17—C16	1.408 (3)	Cl—O5	1.388 (2)
C17—C12	1.419 (3)	Cl—O4	1.402 (3)

O1—Cu—N3	90.91 (7)	C7—C8—C17	120.07 (19)
O1—Cu—N1	86.12 (9)	C16—C17—C12	117.2 (2)
N3—Cu—N1	158.55 (11)	C16—C17—C8	123.6 (2)
O1—Cu—N2	151.48 (8)	C12—C17—C8	119.3 (2)
N3—Cu—N2	93.65 (8)	C15—C16—C17	121.1 (2)
N1—Cu—N2	99.07 (9)	C15—C16—H16	119.4
C1—N1—Cu	122.3 (2)	C17—C16—H16	119.4
C1—N1—H1	103 (2)	C16—C15—C14	120.8 (2)
Cu—N1—H1	108 (2)	C16—C15—H15	119.6
C1—N1—H2	110 (2)	C14—C15—H15	119.6
Cu—N1—H2	103 (2)	C13—C14—C15	119.7 (2)
H1—N1—H2	111 (3)	C13—C14—H14	120.1
N1—C1—C2	112.2 (2)	C15—C14—H14	120.1
N1—C1—H1A	109.2	C14—C13—C12	121.1 (3)
C2—C1—H1A	109.2	C14—C13—H13	119.5
N1—C1—H1B	109.2	C12—C13—H13	119.5
C2—C1—H1B	109.2	C13—C12—C17	120.1 (2)
H1A—C1—H1B	107.9	C13—C12—C11	121.0 (2)
C3—C2—C1	114.1 (3)	C17—C12—C11	118.9 (2)
C3—C2—H2A	108.7	C10—C11—C12	121.7 (2)
C1—C2—H2A	108.7	C10—C11—H11	119.2
C3—C2—H2B	108.7	C12—C11—H11	119.2
C1—C2—H2B	108.7	C11—C10—C9	121.5 (2)
H2A—C2—H2B	107.6	C11—C10—H10	119.2
N2—C3—C2	116.6 (2)	C9—C10—H10	119.2
N2—C3—H3A	108.1	O1—C9—C8	124.3 (2)
C2—C3—H3A	108.1	O1—C9—C10	116.8 (2)
N2—C3—H3B	108.1	C8—C9—C10	118.8 (2)
C2—C3—H3B	108.1	C9—O1—Cu	124.70 (14)
H3A—C3—H3B	107.3	N2—C18—C19	115.07 (18)
C3—N2—C18	106.7 (2)	N2—C18—H18A	108.5
C3—N2—C4	108.2 (2)	C19—C18—H18A	108.5
C18—N2—C4	105.99 (19)	N2—C18—H18B	108.5
C3—N2—Cu	112.97 (17)	C19—C18—H18B	108.5
C18—N2—Cu	112.54 (13)	H18A—C18—H18B	107.5
C4—N2—Cu	110.16 (16)	C20—C19—C24	115.0 (2)
C5—C4—N2	112.9 (2)	C20—C19—C18	126.9 (2)
C5—C4—H4A	109.0	C24—C19—C18	117.9 (2)
N2—C4—H4A	109.0	C23—C24—C19	122.5 (3)
C5—C4—H4B	109.0	C23—C24—H24	118.7
N2—C4—H4B	109.0	C19—C24—H24	118.7
H4A—C4—H4B	107.8	C22—C23—C24	120.1 (3)
C4—C5—C6	112.7 (2)	C22—C23—H23	120.0
C4—C5—H5A	109.1	C24—C23—H23	120.0
C6—C5—H5A	109.1	C21—C22—C23	119.6 (3)
C4—C5—H5B	109.1	C21—C22—H22	120.2
C6—C5—H5B	109.1	C23—C22—H22	120.2
H5A—C5—H5B	107.8	C22—C21—C20	120.2 (3)
N3—C6—C5	111.9 (2)	C22—C21—H21	119.9
N3—C6—H6A	109.2	C20—C21—H21	119.9
C5—C6—H6A	109.2	C21—C20—C19	122.6 (2)
N3—C6—H6B	109.2	C21—C20—N4	115.2 (2)
C5—C6—H6B	109.2	C19—C20—N4	122.2 (2)
H6A—C6—H6B	107.9	O2—N4—O3	122.7 (3)
C7—N3—C6	118.23 (19)	O2—N4—C20	118.3 (3)
C7—N3—Cu	123.45 (15)	O3—N4—C20	119.1 (2)
C6—N3—Cu	118.33 (15)	O7—Cl—O6	107.8 (5)
N3—C7—C8	126.47 (19)	O7—Cl—O5	111.5 (3)
N3—C7—H7	116.8	O6—Cl—O5	107.4 (2)
C8—C7—H7	116.8	O7—Cl—O4	106.5 (2)
C9—C8—C7	120.22 (19)	O6—Cl—O4	112.2 (3)
C9—C8—C17	119.6 (2)	O5—Cl—O4	111.4 (2)

O1—Cu—N1—C1	−170.5 (3)	C16—C15—C14—C13	0.4 (4)
N3—Cu—N1—C1	106.9 (3)	C15—C14—C13—C12	0.0 (4)
N2—Cu—N1—C1	−18.7 (3)	C14—C13—C12—C17	−1.2 (4)
Cu—N1—C1—C2	41.3 (4)	C14—C13—C12—C11	178.1 (2)
N1—C1—C2—C3	−67.9 (4)	C16—C17—C12—C13	1.9 (3)
C1—C2—C3—N2	75.1 (4)	C8—C17—C12—C13	−179.3 (2)
C2—C3—N2—C18	77.0 (3)	C16—C17—C12—C11	−177.4 (2)
C2—C3—N2—C4	−169.4 (3)	C8—C17—C12—C11	1.4 (3)
C2—C3—N2—Cu	−47.2 (3)	C13—C12—C11—C10	−177.6 (2)
O1—Cu—N2—C3	118.2 (2)	C17—C12—C11—C10	1.7 (4)
N3—Cu—N2—C3	−143.12 (18)	C12—C11—C10—C9	−1.3 (4)
N1—Cu—N2—C3	19.6 (2)	C7—C8—C9—O1	8.8 (3)
O1—Cu—N2—C18	−2.7 (2)	C17—C8—C9—O1	−175.4 (2)
N3—Cu—N2—C18	96.00 (16)	C7—C8—C9—C10	−170.5 (2)
N1—Cu—N2—C18	−101.32 (17)	C17—C8—C9—C10	5.2 (3)
O1—Cu—N2—C4	−120.71 (19)	C11—C10—C9—O1	178.4 (2)
N3—Cu—N2—C4	−22.04 (17)	C11—C10—C9—C8	−2.2 (4)
N1—Cu—N2—C4	140.64 (18)	C8—C9—O1—Cu	19.6 (3)
C3—N2—C4—C5	89.5 (3)	C10—C9—O1—Cu	−161.05 (17)
C18—N2—C4—C5	−156.4 (2)	N3—Cu—O1—C9	−32.2 (2)
Cu—N2—C4—C5	−34.4 (3)	N1—Cu—O1—C9	169.1 (2)
N2—C4—C5—C6	83.4 (3)	N2—Cu—O1—C9	67.2 (3)
C4—C5—C6—N3	−47.7 (3)	C3—N2—C18—C19	−168.7 (2)
C5—C6—N3—C7	154.6 (2)	C4—N2—C18—C19	76.2 (2)
C5—C6—N3—Cu	−25.0 (3)	Cu—N2—C18—C19	−44.3 (2)
O1—Cu—N3—C7	26.90 (18)	N2—C18—C19—C20	91.4 (3)
N1—Cu—N3—C7	108.6 (3)	N2—C18—C19—C24	−94.6 (3)
N2—Cu—N3—C7	−124.94 (18)	C20—C19—C24—C23	−3.0 (4)
O1—Cu—N3—C6	−153.60 (18)	C18—C19—C24—C23	−177.8 (3)
N1—Cu—N3—C6	−71.9 (3)	C19—C24—C23—C22	1.6 (5)
N2—Cu—N3—C6	54.57 (18)	C24—C23—C22—C21	0.4 (5)
C6—N3—C7—C8	170.9 (2)	C23—C22—C21—C20	−0.7 (4)
Cu—N3—C7—C8	−9.6 (3)	C22—C21—C20—C19	−1.0 (4)
N3—C7—C8—C9	−14.2 (3)	C22—C21—C20—N4	176.4 (2)
N3—C7—C8—C17	170.1 (2)	C24—C19—C20—C21	2.7 (3)
C9—C8—C17—C16	173.8 (2)	C18—C19—C20—C21	176.9 (2)
C7—C8—C17—C16	−10.4 (3)	C24—C19—C20—N4	−174.5 (2)
C9—C8—C17—C12	−4.9 (3)	C18—C19—C20—N4	−0.3 (4)
C7—C8—C17—C12	170.84 (19)	C21—C20—N4—O2	−9.1 (3)
C12—C17—C16—C15	−1.5 (3)	C19—C20—N4—O2	168.3 (2)
C8—C17—C16—C15	179.7 (2)	C21—C20—N4—O3	171.4 (2)
C17—C16—C15—C14	0.4 (4)	C19—C20—N4—O3	−11.2 (3)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₄H₂₇N₄O₃)]ClO₄
M_r	582.50
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.1062 (4), 19.2907 (8), 16.0959 (7)
β (°)	102.072 (2)
V (Å³)	2461.32 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.51 × 0.49 × 0.32

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.706, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	101979, 5377, 4605
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.02
No. of reflections	5377
No. of parameters	342
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.52

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XPW (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

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

References

Atkins, A. J., Blake, A. J. & Schröder, M. (1993). J. Chem. Soc. Chem. Commun. pp. 1662–1664. CrossRef Web of Science Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Matsumoto, N., Inoue, K., Okawa, H. & Kida, S. (1989). Chem. Lett. pp. 1251–1254. CrossRef Web of Science Google Scholar
Plieger, P. G., Downard, A. J., Moubaraki, B., Murray, K. S. & Brooker, S. (2004). Dalton Trans. pp. 2157–2165. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XPW. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Vigato, P. A., Tamburini, S. & Bertolo, L. (2007). Coord. Chem. Rev. 251, 1311–1492. Web of Science CrossRef CAS Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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