Bis{2-[2-(isopropyl­ammonio)ethyl­imino­meth­yl]-5-methoxy­phenolato}copper(II) bis­(perchlorate)

Wang, C.-Y.; Cao, F.; Wang, P.; Wu, X.; Yuan, C.-J.

doi:10.1107/S1600536810017472

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages m669-m670

https://doi.org/10.1107/S1600536810017472

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Bis{2-[2-(isopropylammonio)ethyliminomethyl]-5-methoxyphenolato}copper(II) bis(perchlorate)

Chen-Yi Wang,^a ^* Feng Cao,^a Ping Wang,^b Xiang Wu ^a and Cai-Jun Yuan ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China, and ^bCollege of Chemical Engineering, Nanjing Forestry University, Nangjing 210037, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 18 April 2010; accepted 12 May 2010; online 19 May 2010)

In the title compound, [Cu(C₁₃H₂₀N₂O₂)₂](ClO₄)₂, the Cu^II atom in the complex dication is chelated by two phenolate O atoms and two imine N atoms from two zwitterionic 2-[2-(isopropylammonio)ethyliminomethyl]-5-methoxyphenolate ligands, forming a distorted square-planar geometry. One of the perchlorate anions is disordered over two sites with occupancies of 0.611 (15) and 0.389 (15). Intramolecular N—H⋯O hydrogen bonds are observed in the complex dication. In the crystal structure, the perchlorate anions are linked to complex dications by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to Cu^II complexes, see: Collinson & Fenton (1996 ); Hossain et al. (1996 ); Tarafder et al. (2002 ); Musie et al. (2003 ); García-Raso et al. (2003 ); Reddy et al. (2000 ); Ray et al. (2003 ); Arnold et al. (2003 ); Raptopoulou et al. (1998 ). For related structures, see: Wang et al. (2009a ,b , 2010 ); Wang (2009 ). For bond lengths and angles in related Cu^II complexes, see: Hebbachi & Benali-Cherif (2005 ); Butcher et al. (2003 ); Elmali et al. (2000 ); Warda et al. (1997 ).

Experimental

Crystal data

[Cu(C₁₃H₂₀N₂O₂)₂](ClO₄)₂
M_r = 735.06
Orthorhombic, P b c a
a = 17.4415 (13) Å
b = 14.009 (1) Å
c = 26.350 (2) Å
V = 6438.2 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.839, T_max = 0.861
36964 measured reflections
7004 independent reflections
3260 reflections with I > 2σ(I)
R_int = 0.117

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.182
S = 1.01
7004 reflections
449 parameters
94 restraints
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.925 (3)
Cu1—O3	1.933 (3)
Cu1—N3	1.969 (4)
Cu1—N1	1.970 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O1	0.90	1.86	2.705 (5)	156
N4—H4A⋯O12	0.90	2.04	2.930 (13)	171
N2—H2B⋯O3	0.90	2.23	2.849 (5)	125
N2—H2A⋯O6	0.90	2.20	3.070 (9)	163

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810017472/ci5083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017472/ci5083Isup2.hkl

checkCIF report

Comment top

In recent years, copper(II) complexes have received much attention for their interesting biological activities and versatile structures (Collinson & Fenton, 1996; Hossain et al., 1996; Tarafder et al., 2002; Musie et al., 2003; García-Raso et al., 2003). Considerable effort has been made to construct a variety of copper(II) complexes in an attempt to model the physical and chemical behaviour of copper-containing metalloenzymes (Reddy et al., 2000). The peculiarity of copper lies in its ability to form complexes with coordination number four, five, and six (Ray et al., 2003; Arnold et al., 2003; Raptopoulou et al., 1998). As part of our investigations into novel urease inhibitors (Wang et al., 2009a,b,2010; Wang, 2009), the title compound, a new Cu^II complex, has been synthesized, and its crystal structure is reported here.

The asymmetric units contains one mononuclear copper(II) complex dication, and two perchlorate anions (Fig. 1). The Cu^II atom in the dication is chelated by two phenolate O atoms and two imine N atoms from two 2-[(2-isopropylammonioethylimino)methyl]-5-methoxyphenolate ligands, forming a square-planar geometry. The coordinate bond lengths (Table 1) and angles are typical and are comparable with those observed in other related copper(II) complexes (Hebbachi & Benali-Cherif, 2005; Butcher et al., 2003; Elmali et al., 2000; Warda et al., 1997). There are two intramolecular N—H···O hydrogen bonds in the complex dication.

In the crystal structure, the perchlorate anions are linked to the complex dications by intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2).

Related literature top

For general background to Cu^II complexes, see: Collinson & Fenton (1996); Hossain et al. (1996); Tarafder et al. (2002); Musie et al. (2003); García-Raso et al. (2003); Reddy et al. (2000); Ray et al. (2003); Arnold et al. (2003); Raptopoulou et al. (1998). For related structures, see: Wang et al. (2009a,b, 2010); Wang (2009). For bond lengths and angles in related Cu^II complexes, see: Hebbachi & Benali-Cherif (2005); Butcher et al. (2003); Elmali et al. (2000); Warda et al. (1997).

Experimental top

4-Methoxysalicylaldehyde (1.0 mmol, 152 mg), N-isopropyl-1,2-diaminoethane (1.0 mmol, 102 mg) and Cu(ClO₄)₂.6H₂O (1.0 mmol, 370 mg) were dissolved in methanol (80 ml). The mixture was stirred at room temperature for about 1 h to give a blue solution. After keeping the solution in air for a few days, blue block-like crystals were formed.

Structure description top

In the crystal structure, the perchlorate anions are linked to the complex dications by intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2).

For general background to Cu^II complexes, see: Collinson & Fenton (1996); Hossain et al. (1996); Tarafder et al. (2002); Musie et al. (2003); García-Raso et al. (2003); Reddy et al. (2000); Ray et al. (2003); Arnold et al. (2003); Raptopoulou et al. (1998). For related structures, see: Wang et al. (2009a,b, 2010); Wang (2009). For bond lengths and angles in related Cu^II complexes, see: Hebbachi & Benali-Cherif (2005); Butcher et al. (2003); Elmali et al. (2000); Warda et al. (1997).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title complex, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. C-bound H atoms have been omitted for clarity. Only the major disorder component of one of the perchlorate anions is shown.
	Fig. 2. The crystal packing of the title compound. Intermolecular N—H···O hydrogen bonds are drawn as dashed lines.

Bis{2-[2-(isopropylammonio)ethyliminomethyl]-5-methoxyphenolato}copper(II) bis(perchlorate) top

Crystal data top

[Cu(C₁₃H₂₀N₂O₂)₂](ClO₄)₂	F(000) = 3064
M_r = 735.06	D_x = 1.517 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2387 reflections
a = 17.4415 (13) Å	θ = 2.4–24.5°
b = 14.009 (1) Å	µ = 0.91 mm⁻¹
c = 26.350 (2) Å	T = 298 K
V = 6438.2 (8) Å³	Block, blue
Z = 8	0.20 × 0.18 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7004 independent reflections
Radiation source: fine-focus sealed tube	3260 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.117
ω scan	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→20
T_min = 0.839, T_max = 0.861	k = −17→17
36964 measured reflections	l = −29→33

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0802P)² + 0.2786P] where P = (F_o² + 2F_c²)/3
7004 reflections	(Δ/σ)_max = 0.001
449 parameters	Δρ_max = 0.67 e Å⁻³
94 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cu(C₁₃H₂₀N₂O₂)₂](ClO₄)₂	V = 6438.2 (8) Å³
M_r = 735.06	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.4415 (13) Å	µ = 0.91 mm⁻¹
b = 14.009 (1) Å	T = 298 K
c = 26.350 (2) Å	0.20 × 0.18 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7004 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3260 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.861	R_int = 0.117
36964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	94 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.01	Δρ_max = 0.67 e Å⁻³
7004 reflections	Δρ_min = −0.39 e Å⁻³
449 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > σ(F²) 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	Occ. (<1)
Cu1	0.20772 (3)	0.30739 (5)	0.29436 (2)	0.0430 (2)
Cl1	0.35617 (10)	0.50449 (12)	0.29759 (6)	0.0669 (5)
N1	0.2829 (2)	0.2199 (3)	0.32521 (16)	0.0443 (11)
N2	0.3178 (3)	0.3382 (3)	0.41567 (18)	0.0574 (13)
H2A	0.3298	0.3618	0.3849	0.069*
H2B	0.2676	0.3497	0.4207	0.069*
N3	0.1097 (2)	0.3435 (3)	0.26267 (15)	0.0417 (10)
N4	0.1766 (2)	0.4031 (3)	0.15898 (16)	0.0528 (12)
H4A	0.1910	0.3676	0.1321	0.063*
H4B	0.2056	0.3851	0.1856	0.063*
O1	0.2543 (2)	0.2985 (3)	0.22831 (13)	0.0514 (10)
O2	0.4443 (2)	0.2600 (3)	0.10520 (15)	0.0643 (11)
O3	0.17867 (19)	0.3576 (2)	0.35993 (12)	0.0444 (9)
O4	0.0587 (2)	0.5763 (3)	0.47332 (14)	0.0559 (10)
O5	0.3648 (3)	0.5847 (5)	0.3286 (3)	0.147 (2)
O6	0.3925 (4)	0.4248 (5)	0.3208 (3)	0.159 (3)
O7	0.3923 (3)	0.5183 (5)	0.2529 (2)	0.148 (2)
O8	0.2780 (3)	0.4867 (4)	0.2923 (3)	0.135 (2)
Cl2'	0.17958 (9)	0.25224 (11)	0.03722 (6)	0.0601 (4)	0.389 (15)
O9'	0.1570 (12)	0.2204 (11)	0.0869 (4)	0.129 (7)	0.389 (15)
O10'	0.2039 (11)	0.1768 (11)	0.0069 (7)	0.122 (8)	0.389 (15)
O11'	0.1144 (9)	0.3020 (11)	0.0192 (8)	0.141 (8)	0.389 (15)
O12'	0.2391 (10)	0.3202 (14)	0.0434 (8)	0.132 (10)	0.389 (15)
Cl2	0.17958 (9)	0.25224 (11)	0.03722 (6)	0.0601 (4)	0.611 (15)
O9	0.1079 (6)	0.2451 (11)	0.0606 (6)	0.164 (6)	0.611 (15)
O10	0.2095 (8)	0.1581 (7)	0.0317 (6)	0.145 (6)	0.611 (15)
O11	0.1749 (9)	0.2871 (9)	−0.0129 (3)	0.157 (6)	0.611 (15)
O12	0.2292 (6)	0.3064 (10)	0.0667 (5)	0.133 (6)	0.611 (15)
C1	0.3633 (3)	0.2031 (3)	0.2500 (2)	0.0433 (13)
C2	0.3208 (3)	0.2609 (4)	0.21648 (19)	0.0419 (12)
C3	0.3518 (3)	0.2759 (4)	0.1675 (2)	0.0496 (14)
H3	0.3243	0.3121	0.1441	0.060*
C4	0.4217 (3)	0.2383 (4)	0.1535 (2)	0.0466 (13)
C5	0.4627 (3)	0.1818 (4)	0.1865 (2)	0.0510 (14)
H5	0.5096	0.1557	0.1769	0.061*
C6	0.4335 (3)	0.1650 (4)	0.2330 (2)	0.0510 (15)
H6	0.4611	0.1262	0.2550	0.061*
C7	0.3393 (3)	0.1828 (4)	0.3006 (2)	0.0447 (13)
H7	0.3678	0.1372	0.3180	0.054*
C8	0.2723 (3)	0.1865 (4)	0.3781 (2)	0.0536 (15)
H8A	0.2791	0.1178	0.3793	0.064*
H8B	0.2205	0.2008	0.3890	0.064*
C9	0.3286 (4)	0.2335 (4)	0.4139 (2)	0.0597 (16)
H9A	0.3220	0.2073	0.4477	0.072*
H9B	0.3805	0.2194	0.4029	0.072*
C10	0.3603 (4)	0.3919 (5)	0.4532 (3)	0.084 (2)
H10	0.3401	0.3683	0.4856	0.101*
C11	0.4435 (4)	0.3724 (7)	0.4567 (4)	0.151 (4)
H11A	0.4674	0.3862	0.4247	0.182*
H11B	0.4515	0.3065	0.4651	0.182*
H11C	0.4657	0.4120	0.4826	0.182*
C12	0.3397 (4)	0.4960 (4)	0.4536 (3)	0.085 (2)
H12A	0.3656	0.5271	0.4812	0.102*
H12B	0.2853	0.5028	0.4578	0.102*
H12C	0.3551	0.5247	0.4222	0.102*
C13	0.5160 (3)	0.2259 (5)	0.0871 (3)	0.0691 (18)
H13A	0.5554	0.2416	0.1111	0.083*
H13B	0.5274	0.2552	0.0551	0.083*
H13C	0.5136	0.1579	0.0830	0.083*
C14	0.0646 (3)	0.4398 (4)	0.33394 (18)	0.0391 (12)
C15	0.1234 (3)	0.4187 (4)	0.36975 (19)	0.0397 (12)
C16	0.1200 (3)	0.4628 (4)	0.41700 (19)	0.0416 (13)
H16	0.1566	0.4472	0.4413	0.050*
C17	0.0644 (3)	0.5287 (4)	0.4289 (2)	0.0457 (13)
C18	0.0072 (3)	0.5516 (4)	0.3937 (2)	0.0482 (14)
H18	−0.0299	0.5971	0.4012	0.058*
C19	0.0073 (3)	0.5055 (4)	0.3478 (2)	0.0472 (14)
H19	−0.0321	0.5181	0.3250	0.057*
C20	0.0594 (3)	0.3960 (4)	0.28523 (19)	0.0438 (13)
H20	0.0140	0.4065	0.2675	0.053*
C21	0.0873 (3)	0.3067 (4)	0.2121 (2)	0.0573 (16)
H21A	0.0345	0.2853	0.2134	0.069*
H21B	0.1191	0.2520	0.2039	0.069*
C22	0.0957 (3)	0.3814 (5)	0.1706 (2)	0.0640 (18)
H22A	0.0706	0.3586	0.1401	0.077*
H22B	0.0701	0.4395	0.1812	0.077*
C23	0.1938 (4)	0.5072 (4)	0.1473 (2)	0.0620 (17)
H23	0.1742	0.5462	0.1753	0.074*
C24	0.2780 (4)	0.5209 (5)	0.1442 (3)	0.093 (2)
H24A	0.3018	0.4941	0.1738	0.112*
H24B	0.2894	0.5878	0.1424	0.112*
H24C	0.2973	0.4895	0.1144	0.112*
C25	0.1517 (4)	0.5364 (5)	0.0988 (2)	0.082 (2)
H25A	0.1738	0.5037	0.0703	0.098*
H25B	0.1564	0.6041	0.0940	0.098*
H25C	0.0985	0.5198	0.1017	0.098*
C26	0.1108 (4)	0.5532 (4)	0.5135 (2)	0.0648 (17)
H26A	0.1047	0.4873	0.5226	0.078*
H26B	0.1001	0.5927	0.5424	0.078*
H26C	0.1624	0.5640	0.5023	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0412 (4)	0.0492 (4)	0.0387 (4)	0.0057 (3)	−0.0002 (3)	0.0029 (3)
Cl1	0.0691 (11)	0.0669 (11)	0.0649 (11)	−0.0151 (9)	0.0239 (9)	−0.0104 (9)
N1	0.053 (3)	0.037 (2)	0.043 (3)	0.003 (2)	−0.005 (2)	0.005 (2)
N2	0.051 (3)	0.063 (3)	0.058 (3)	0.015 (2)	−0.012 (2)	−0.012 (2)
N3	0.039 (2)	0.049 (3)	0.037 (3)	−0.001 (2)	0.000 (2)	0.001 (2)
N4	0.051 (3)	0.074 (4)	0.034 (3)	0.017 (3)	−0.001 (2)	0.006 (2)
O1	0.046 (2)	0.064 (3)	0.044 (2)	0.019 (2)	0.0036 (18)	0.0074 (18)
O2	0.057 (3)	0.074 (3)	0.061 (3)	0.010 (2)	0.015 (2)	0.002 (2)
O3	0.041 (2)	0.051 (2)	0.041 (2)	0.0093 (18)	−0.0017 (16)	0.0019 (17)
O4	0.062 (3)	0.059 (3)	0.046 (2)	0.002 (2)	0.005 (2)	−0.0064 (19)
O5	0.115 (4)	0.140 (5)	0.186 (6)	−0.023 (4)	0.009 (4)	−0.075 (5)
O6	0.172 (6)	0.147 (5)	0.159 (6)	0.045 (5)	0.010 (5)	0.046 (5)
O7	0.124 (4)	0.236 (6)	0.083 (4)	0.000 (4)	0.044 (3)	0.022 (4)
O8	0.081 (4)	0.112 (4)	0.211 (6)	−0.031 (3)	0.039 (4)	−0.051 (4)
Cl2'	0.0687 (10)	0.0550 (10)	0.0566 (10)	−0.0030 (9)	−0.0040 (8)	0.0000 (8)
O9'	0.144 (11)	0.142 (10)	0.100 (9)	0.017 (8)	0.020 (8)	0.043 (8)
O10'	0.141 (11)	0.119 (11)	0.105 (10)	0.003 (8)	0.013 (8)	−0.047 (8)
O11'	0.116 (11)	0.145 (11)	0.161 (12)	0.028 (8)	−0.040 (9)	0.030 (8)
O12'	0.128 (12)	0.126 (12)	0.142 (13)	−0.047 (8)	0.004 (9)	−0.015 (9)
Cl2	0.0687 (10)	0.0550 (10)	0.0566 (10)	−0.0030 (9)	−0.0040 (8)	0.0000 (8)
O9	0.108 (8)	0.204 (10)	0.179 (10)	−0.006 (7)	0.050 (7)	−0.008 (8)
O10	0.188 (9)	0.102 (7)	0.144 (9)	0.044 (6)	−0.028 (8)	−0.011 (6)
O11	0.179 (10)	0.187 (10)	0.105 (8)	−0.003 (7)	−0.018 (7)	0.049 (6)
O12	0.082 (7)	0.208 (14)	0.109 (10)	−0.044 (7)	−0.002 (7)	−0.089 (9)
C1	0.043 (3)	0.039 (3)	0.047 (3)	0.005 (3)	−0.006 (3)	−0.003 (3)
C2	0.038 (3)	0.043 (3)	0.045 (3)	0.005 (3)	−0.003 (2)	−0.003 (2)
C3	0.046 (3)	0.057 (4)	0.046 (3)	0.014 (3)	−0.002 (3)	−0.002 (3)
C4	0.046 (3)	0.050 (3)	0.044 (3)	−0.007 (3)	0.005 (3)	−0.006 (3)
C5	0.039 (3)	0.050 (4)	0.064 (4)	0.007 (3)	0.002 (3)	−0.008 (3)
C6	0.045 (3)	0.052 (4)	0.056 (4)	0.013 (3)	−0.010 (3)	−0.004 (3)
C7	0.057 (3)	0.035 (3)	0.042 (3)	0.004 (3)	−0.011 (3)	0.000 (2)
C8	0.072 (4)	0.040 (3)	0.049 (3)	0.008 (3)	−0.001 (3)	0.011 (3)
C9	0.073 (4)	0.062 (4)	0.045 (3)	0.013 (3)	−0.009 (3)	0.007 (3)
C10	0.084 (5)	0.103 (6)	0.065 (5)	−0.010 (5)	−0.020 (4)	−0.003 (4)
C11	0.112 (6)	0.167 (8)	0.175 (8)	0.016 (6)	−0.071 (6)	−0.036 (6)
C12	0.094 (5)	0.077 (5)	0.084 (5)	−0.018 (4)	0.006 (4)	−0.024 (4)
C13	0.050 (4)	0.077 (5)	0.080 (5)	−0.003 (3)	0.021 (3)	−0.015 (4)
C14	0.038 (3)	0.046 (3)	0.033 (3)	0.002 (3)	0.007 (2)	0.004 (2)
C15	0.043 (3)	0.038 (3)	0.038 (3)	−0.003 (2)	0.006 (2)	0.009 (2)
C16	0.041 (3)	0.050 (3)	0.034 (3)	−0.004 (3)	−0.002 (2)	0.007 (2)
C17	0.053 (3)	0.042 (3)	0.042 (3)	−0.005 (3)	0.012 (3)	0.003 (3)
C18	0.043 (3)	0.044 (3)	0.058 (4)	0.008 (3)	0.008 (3)	0.001 (3)
C19	0.036 (3)	0.054 (4)	0.052 (4)	0.003 (3)	0.006 (3)	0.011 (3)
C20	0.032 (3)	0.059 (4)	0.041 (3)	−0.004 (3)	−0.002 (2)	0.013 (3)
C21	0.044 (3)	0.081 (4)	0.047 (4)	−0.006 (3)	−0.009 (3)	−0.006 (3)
C22	0.053 (4)	0.105 (5)	0.034 (3)	0.016 (4)	−0.010 (3)	0.002 (3)
C23	0.078 (5)	0.059 (4)	0.049 (4)	0.017 (4)	−0.003 (3)	−0.002 (3)
C24	0.095 (6)	0.078 (5)	0.107 (6)	−0.004 (4)	−0.007 (5)	0.019 (4)
C25	0.110 (6)	0.079 (5)	0.056 (4)	0.033 (4)	−0.004 (4)	0.012 (4)
C26	0.081 (5)	0.068 (4)	0.045 (4)	0.004 (4)	0.003 (3)	−0.008 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.925 (3)	C8—H8B	0.97
Cu1—O3	1.933 (3)	C9—H9A	0.97
Cu1—N3	1.969 (4)	C9—H9B	0.97
Cu1—N1	1.970 (4)	C10—C11	1.479 (7)
Cl1—O7	1.349 (5)	C10—C12	1.502 (6)
Cl1—O8	1.393 (5)	C10—H10	0.98
Cl1—O5	1.398 (6)	C11—H11A	0.96
Cl1—O6	1.422 (6)	C11—H11B	0.96
N1—C7	1.287 (6)	C11—H11C	0.96
N1—C8	1.481 (6)	C12—H12A	0.96
N2—C10	1.447 (7)	C12—H12B	0.96
N2—C9	1.480 (7)	C12—H12C	0.96
N2—H2A	0.90	C13—H13A	0.96
N2—H2B	0.90	C13—H13B	0.96
N3—C20	1.290 (6)	C13—H13C	0.96
N3—C21	1.480 (6)	C14—C19	1.407 (7)
N4—C22	1.476 (7)	C14—C15	1.424 (7)
N4—C23	1.520 (7)	C14—C20	1.426 (7)
N4—H4A	0.90	C15—C16	1.391 (7)
N4—H4B	0.90	C16—C17	1.375 (7)
O1—C2	1.312 (6)	C16—H16	0.93
O2—C4	1.366 (6)	C17—C18	1.400 (7)
O2—C13	1.421 (6)	C18—C19	1.370 (7)
O3—C15	1.315 (6)	C18—H18	0.93
O4—C17	1.351 (6)	C19—H19	0.93
O4—C26	1.431 (6)	C20—H20	0.93
Cl2'—O10'	1.391 (8)	C21—C22	1.521 (8)
Cl2'—O11'	1.416 (8)	C21—H21A	0.97
Cl2'—O12'	1.418 (9)	C21—H21B	0.97
Cl2'—O9'	1.437 (8)	C22—H22A	0.97
C1—C2	1.409 (7)	C22—H22B	0.97
C1—C6	1.410 (7)	C23—C24	1.484 (8)
C1—C7	1.427 (7)	C23—C25	1.529 (8)
C2—C3	1.416 (7)	C23—H23	0.98
C3—C4	1.379 (7)	C24—H24A	0.96
C3—H3	0.93	C24—H24B	0.96
C4—C5	1.376 (7)	C24—H24C	0.96
C5—C6	1.348 (7)	C25—H25A	0.96
C5—H5	0.93	C25—H25B	0.96
C6—H6	0.93	C25—H25C	0.96
C7—H7	0.93	C26—H26A	0.96
C8—C9	1.513 (8)	C26—H26B	0.96
C8—H8A	0.97	C26—H26C	0.96

O1—Cu1—O3	160.46 (15)	C11—C10—H10	103.6
O1—Cu1—N3	89.97 (16)	C12—C10—H10	103.6
O3—Cu1—N3	93.31 (16)	C10—C11—H11A	109.5
O1—Cu1—N1	92.98 (16)	C10—C11—H11B	109.5
O3—Cu1—N1	91.84 (16)	H11A—C11—H11B	109.5
N3—Cu1—N1	155.90 (17)	C10—C11—H11C	109.5
O7—Cl1—O8	113.3 (4)	H11A—C11—H11C	109.5
O7—Cl1—O5	110.2 (5)	H11B—C11—H11C	109.5
O8—Cl1—O5	107.9 (4)	C10—C12—H12A	109.5
O7—Cl1—O6	106.2 (4)	C10—C12—H12B	109.5
O8—Cl1—O6	109.8 (4)	H12A—C12—H12B	109.5
O5—Cl1—O6	109.4 (5)	C10—C12—H12C	109.5
C7—N1—C8	116.1 (4)	H12A—C12—H12C	109.5
C7—N1—Cu1	123.5 (4)	H12B—C12—H12C	109.5
C8—N1—Cu1	120.1 (3)	O2—C13—H13A	109.5
C10—N2—C9	118.1 (5)	O2—C13—H13B	109.5
C10—N2—H2A	107.8	H13A—C13—H13B	109.5
C9—N2—H2A	107.8	O2—C13—H13C	109.5
C10—N2—H2B	107.8	H13A—C13—H13C	109.5
C9—N2—H2B	107.8	H13B—C13—H13C	109.5
H2A—N2—H2B	107.1	C19—C14—C15	118.4 (5)
C20—N3—C21	115.7 (4)	C19—C14—C20	118.0 (5)
C20—N3—Cu1	122.8 (3)	C15—C14—C20	123.6 (5)
C21—N3—Cu1	121.4 (3)	O3—C15—C16	119.7 (5)
C22—N4—C23	115.3 (5)	O3—C15—C14	122.2 (5)
C22—N4—H4A	108.4	C16—C15—C14	118.1 (5)
C23—N4—H4A	108.4	C17—C16—C15	122.1 (5)
C22—N4—H4B	108.4	C17—C16—H16	118.9
C23—N4—H4B	108.4	C15—C16—H16	118.9
H4A—N4—H4B	107.5	O4—C17—C16	125.5 (5)
C2—O1—Cu1	127.9 (3)	O4—C17—C18	114.1 (5)
C4—O2—C13	119.4 (5)	C16—C17—C18	120.4 (5)
C15—O3—Cu1	127.2 (3)	C19—C18—C17	118.4 (5)
C17—O4—C26	118.8 (4)	C19—C18—H18	120.8
O10'—Cl2'—O11'	115.3 (10)	C17—C18—H18	120.8
O10'—Cl2'—O12'	110.6 (10)	C18—C19—C14	122.5 (5)
O11'—Cl2'—O12'	107.2 (11)	C18—C19—H19	118.7
O10'—Cl2'—O9'	111.7 (10)	C14—C19—H19	118.7
O11'—Cl2'—O9'	103.8 (9)	N3—C20—C14	128.1 (5)
O12'—Cl2'—O9'	107.7 (10)	N3—C20—H20	116.0
C2—C1—C6	118.4 (5)	C14—C20—H20	116.0
C2—C1—C7	123.2 (5)	N3—C21—C22	112.4 (5)
C6—C1—C7	118.5 (5)	N3—C21—H21A	109.1
O1—C2—C1	123.1 (5)	C22—C21—H21A	109.1
O1—C2—C3	119.7 (5)	N3—C21—H21B	109.1
C1—C2—C3	117.2 (5)	C22—C21—H21B	109.1
C4—C3—C2	121.6 (5)	H21A—C21—H21B	107.8
C4—C3—H3	119.2	N4—C22—C21	112.6 (4)
C2—C3—H3	119.2	N4—C22—H22A	109.1
O2—C4—C5	124.5 (5)	C21—C22—H22A	109.1
O2—C4—C3	114.7 (5)	N4—C22—H22B	109.1
C5—C4—C3	120.7 (5)	C21—C22—H22B	109.1
C6—C5—C4	118.6 (5)	H22A—C22—H22B	107.8
C6—C5—H5	120.7	C24—C23—N4	109.2 (5)
C4—C5—H5	120.7	C24—C23—C25	113.2 (6)
C5—C6—C1	123.5 (5)	N4—C23—C25	109.3 (5)
C5—C6—H6	118.3	C24—C23—H23	108.3
C1—C6—H6	118.3	N4—C23—H23	108.3
N1—C7—C1	127.8 (5)	C25—C23—H23	108.3
N1—C7—H7	116.1	C23—C24—H24A	109.5
C1—C7—H7	116.1	C23—C24—H24B	109.5
N1—C8—C9	111.6 (5)	H24A—C24—H24B	109.5
N1—C8—H8A	109.3	C23—C24—H24C	109.5
C9—C8—H8A	109.3	H24A—C24—H24C	109.5
N1—C8—H8B	109.3	H24B—C24—H24C	109.5
C9—C8—H8B	109.3	C23—C25—H25A	109.5
H8A—C8—H8B	108.0	C23—C25—H25B	109.5
N2—C9—C8	111.6 (4)	H25A—C25—H25B	109.5
N2—C9—H9A	109.3	C23—C25—H25C	109.5
C8—C9—H9A	109.3	H25A—C25—H25C	109.5
N2—C9—H9B	109.3	H25B—C25—H25C	109.5
C8—C9—H9B	109.3	O4—C26—H26A	109.5
H9A—C9—H9B	108.0	O4—C26—H26B	109.5
N2—C10—C11	116.8 (6)	H26A—C26—H26B	109.5
N2—C10—C12	112.8 (5)	O4—C26—H26C	109.5
C11—C10—C12	114.4 (7)	H26A—C26—H26C	109.5
N2—C10—H10	103.6	H26B—C26—H26C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1	0.90	1.86	2.705 (5)	156
N4—H4A···O12	0.90	2.04	2.930 (13)	171
N2—H2B···O3	0.90	2.23	2.849 (5)	125
N2—H2A···O6	0.90	2.20	3.070 (9)	163

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₂₀N₂O₂)₂](ClO₄)₂
M_r	735.06
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	17.4415 (13), 14.009 (1), 26.350 (2)
V (Å³)	6438.2 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.839, 0.861
No. of measured, independent and observed [I > 2σ(I)] reflections	36964, 7004, 3260
R_int	0.117
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.182, 1.01
No. of reflections	7004
No. of parameters	449
No. of restraints	94
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.39

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.925 (3)	Cu1—N3	1.969 (4)
Cu1—O3	1.933 (3)	Cu1—N1	1.970 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1	0.90	1.86	2.705 (5)	156
N4—H4A···O12	0.90	2.04	2.930 (13)	171
N2—H2B···O3	0.90	2.23	2.849 (5)	125
N2—H2A···O6	0.90	2.20	3.070 (9)	163

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (grant No. 30771696), the Zhejiang Provincial Natural Science Foundation of China (grant No. Y407318), and the Science and Technology Plan of Huzhou (grant No. 2009 GG06).

References

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Volume 66| Part 6| June 2010| Pages m669-m670

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

Bis{2-[2-(iso­propyl­ammonio)ethyl­imino­meth­yl]-5-meth­oxy­phenolato}copper(II) bis­­(perchlorate)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{2-[2-(isopropylammonio)ethyliminomethyl]-5-methoxyphenolato}copper(II) bis(perchlorate)