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Acta Cryst. (2007). E63, m2514    [ doi:10.1107/S1600536807043607 ]

(N-Salicylidene-[beta]-alanine)[1,1-bis(3,5-dimethylpyrazol-1-yl)methane]copper(II)

G.-Q. Zhao, C.-J. Hao, X.-J. Lu, J.-M. Xie and Y.-Z. Song

Abstract top

In the title compound, [Cu(C10H9NO3)(C11H16N4)], the CuII atom is five-coordinated in a distorted square-pyramidal geometry. The basal positions are occupied by three donor atoms from the tridentate Schiff base ligand and by one N atom from a 1,1-bis(3,5-dimethylpyrazol-1-yl)methane ligand. The apical position is occupied by the other N atom of this ligand. The asymmetric unit contains two molecules. There are only van der Waals contacts in the crystal packing.

Comment top

Considerable efforts have been devoted to copper(II) complexes of tridentate Schiff base ligands of the N-alkylidene or N-arylidene aminoacidato type due to their structural richness and electrochemical properties as well as their use as a potential model for a number of important biological systems (Raso et al., 1996, 1999). Several stuctural studies have been performed on Schiff base copper(II) complexes derived from salicylaldehyde and animo acids (Reddy et al., 2002; Wang et al., 2005; Warda, 1997, 1998a,b,c). We report here the crystal structure of the title CuII complex.

The structure consists of discrete monomeric square-pyramidal CuII complex (Fig. 1 and Table 1). The basal positions are occupied by three donor atoms from the tridentate Schiff base ligand, which furnishes an ONO donor set, with the fourth position occupied by one N atom from the 1,1-bis(3,5-dimethylprazol-l-yl)methane ligand. The apical position is occupied by the other N atom of this igand.

The two nitrogen heterocycles are planar and lie at angles of 63.87 (10)° and 59.53 (7)° to the plane of the tridentate Schiff base. The two nitrogen heterocycles form a dihedral angle of 58.71 (14)° with each other. There are only van der Waals contacts in the crystal packing.

Related literature top

For related literature, see: Plesch et al. (1997); Raso et al. (1996, 1999); Wang et al. (2005); Warda (1997, 1998a,b,c); Reddy et al. (2002).

Experimental top

The title compound was synthesized as described in the literature (Plesch et al., 1997). To β-alanine (1.0 mmol) and lithium hydroxide monohydrate (1.0 mmol) in 10 ml of methanol was added salicylaldehyde (1.0 mmol in 10 ml of methanol). The yellow solution was stirred for 1 h at room temperature prior to cooling in an ice bath. The resultant mixture was added dropwise to copper(II) acetate monohydrate (1.0 mmol) and 1,1-bis(3,5-dimethylprazol-l-yl)methane (1.0 mmol) in an aqueous methanol solution (20 ml, 1;1 v/v), and heated with stirring for 2 h at 333 K. The dark green solution was filtered and left for several days; the resulting dark blue crystals were filtered off, washed with water, and dried under vacuum. Analysis found: C 54.95, H 5.49, N 15.26%; calculated: C 54.82, H 5.35, N 14.71%.

Refinement top

All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å (CH) or 0.97 Å (CH2) and Uiso(H) = 1.2Ueq(C), and with C—H = 0.96 Å (CH3) and Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted.
[Figure 2] Fig. 2. A view of the crystal packing along the a axis.
(N-Salicylidene-β-alanine)[1,1-bis(3,5-dimethylpyrazol-1-yl)methane] copper(II) top
Crystal data top
[Cu(C10H9NO3)(C11H16N4)]Z = 4
Mr = 459.00F000 = 956
Triclinic, P1Dx = 1.458 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.1395 (9) ÅCell parameters from 4237 reflections
b = 14.3894 (16) Åθ = 2.3–26.4º
c = 19.271 (2) ŵ = 1.08 mm−1
α = 71.760 (1)ºT = 273 (2) K
β = 79.411 (1)ºBlock, dark green
γ = 79.966 (1)º0.30 × 0.30 × 0.25 mm
V = 2090.6 (4) Å3
Data collection top
Bruker SMART CCD
diffractometer		7278 independent reflections
Radiation source: fine-focus sealed tube5692 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 273(2) Kθmax = 25.1º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.738, Tmax = 0.774k = −16→17
10962 measured reflectionsl = −21→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.099  w = 1/[σ2(Fo2) + (0.0416P)2 + 1.188P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
7278 reflectionsΔρmax = 0.28 e Å−3
549 parametersΔρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu(C10H9NO3)(C11H16N4)]γ = 79.966 (1)º
Mr = 459.00V = 2090.6 (4) Å3
Triclinic, P1Z = 4
a = 8.1395 (9) ÅMo Kα
b = 14.3894 (16) ŵ = 1.08 mm−1
c = 19.271 (2) ÅT = 273 (2) K
α = 71.760 (1)º0.30 × 0.30 × 0.25 mm
β = 79.411 (1)º
Data collection top
Bruker SMART CCD
diffractometer		7278 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5692 reflections with I > 2σ(I)
Tmin = 0.738, Tmax = 0.774Rint = 0.021
10962 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038549 parameters
wR(F2) = 0.099H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å−3
7278 reflectionsΔρmin = −0.32 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
xyzUiso*/Ueq
Cu10.58096 (4)0.58610 (3)0.174452 (19)0.03384 (11)
O10.4334 (3)0.53347 (16)0.26219 (12)0.0476 (6)
O20.6849 (3)0.64875 (15)0.07478 (11)0.0416 (5)
O30.9243 (3)0.6862 (2)0.00468 (14)0.0688 (8)
N10.6090 (3)0.69887 (17)0.20759 (13)0.0343 (5)
N20.8122 (3)0.46820 (18)0.20680 (13)0.0370 (6)
N30.8477 (3)0.39843 (18)0.16911 (13)0.0351 (6)
N40.5103 (3)0.49029 (17)0.12917 (13)0.0333 (5)
N50.6220 (3)0.42616 (17)0.09848 (13)0.0332 (5)
C10.4029 (4)0.5579 (2)0.32336 (16)0.0385 (7)
C20.3138 (4)0.4978 (2)0.38614 (18)0.0502 (9)
H20.27840.44120.38320.060*
C30.2780 (5)0.5211 (3)0.45176 (19)0.0582 (10)
H30.22050.47940.49260.070*
C40.3261 (5)0.6054 (3)0.45813 (19)0.0610 (10)
H40.30060.62060.50270.073*
C50.4110 (4)0.6656 (3)0.39841 (18)0.0483 (8)
H50.44270.72250.40260.058*
C60.4524 (3)0.6442 (2)0.33040 (16)0.0355 (7)
C70.5474 (4)0.7100 (2)0.27160 (16)0.0371 (7)
H70.56680.76690.28030.045*
C80.7002 (4)0.7775 (2)0.15535 (17)0.0395 (7)
H8A0.73130.81740.18200.047*
H8B0.62660.81970.12060.047*
C90.8570 (4)0.7367 (2)0.11345 (17)0.0403 (7)
H9A0.92380.68880.14860.048*
H9B0.92350.79000.08680.048*
C100.8223 (4)0.6881 (2)0.05944 (17)0.0399 (7)
C110.8719 (4)0.4232 (2)0.27010 (17)0.0410 (7)
C120.9458 (4)0.3281 (2)0.27292 (18)0.0491 (8)
H120.99840.28330.31120.059*
C130.9267 (4)0.3126 (2)0.20848 (17)0.0423 (7)
C140.8011 (3)0.4254 (2)0.09625 (15)0.0356 (7)
H14A0.86270.37890.07060.043*
H14B0.83220.49030.06880.043*
C150.5418 (4)0.3773 (2)0.06804 (15)0.0359 (7)
C160.3739 (4)0.4101 (2)0.07960 (17)0.0403 (7)
H160.28670.39020.06470.048*
C170.3592 (3)0.4794 (2)0.11823 (16)0.0345 (7)
C180.2039 (4)0.5365 (3)0.1456 (2)0.0518 (9)
H18A0.17350.50670.19740.078*
H18B0.11370.53650.11970.078*
H18C0.22420.60310.13720.078*
C190.6310 (4)0.3002 (2)0.03268 (18)0.0513 (9)
H19A0.73000.32340.00080.077*
H19B0.55750.28660.00440.077*
H19C0.66290.24100.07020.077*
C200.9746 (5)0.2231 (2)0.1821 (2)0.0609 (10)
H20A0.87460.19800.17970.091*
H20B1.04060.17350.21570.091*
H20C1.03940.24020.13400.091*
C210.8604 (5)0.4779 (3)0.32599 (19)0.0625 (10)
H21A0.86390.54690.30120.094*
H21B0.95340.45280.35370.094*
H21C0.75660.46900.35880.094*
Cu20.21027 (4)0.07442 (3)0.707187 (19)0.03530 (11)
O40.1065 (3)0.00959 (16)0.80327 (12)0.0508 (6)
O50.3530 (3)0.14150 (15)0.61784 (12)0.0445 (5)
O60.3500 (4)0.1832 (2)0.49747 (15)0.0931 (10)
N60.0558 (3)0.19775 (18)0.70325 (14)0.0384 (6)
N70.3991 (3)−0.04190 (17)0.72357 (13)0.0359 (6)
N80.4269 (3)−0.10560 (17)0.68146 (13)0.0354 (6)
N90.0951 (3)−0.00214 (19)0.64183 (14)0.0412 (6)
N100.2008 (3)−0.06555 (18)0.60895 (14)0.0408 (6)
C22−0.0234 (4)0.0411 (2)0.84367 (17)0.0419 (7)
C23−0.0794 (4)−0.0222 (3)0.91284 (19)0.0548 (9)
H23−0.0241−0.08590.92800.066*
C24−0.2142 (5)0.0080 (3)0.95840 (19)0.0603 (10)
H24−0.2479−0.03551.00400.072*
C25−0.3012 (4)0.1020 (3)0.9380 (2)0.0607 (10)
H25−0.39250.12160.96930.073*
C26−0.2507 (4)0.1650 (3)0.8713 (2)0.0504 (9)
H26−0.30850.22820.85750.061*
C27−0.1127 (4)0.1372 (2)0.82239 (17)0.0397 (7)
C28−0.0660 (4)0.2086 (2)0.75413 (18)0.0422 (7)
H28−0.13100.27000.74550.051*
C290.0811 (4)0.2820 (2)0.63729 (18)0.0485 (8)
H29A0.17410.31370.64060.058*
H29B−0.01940.32980.63510.058*
C300.1183 (4)0.2501 (2)0.56744 (18)0.0491 (8)
H30A0.02990.21300.56700.059*
H30B0.11500.30850.52520.059*
C310.2861 (4)0.1879 (2)0.5588 (2)0.0490 (8)
C320.4749 (4)−0.0889 (2)0.78276 (16)0.0400 (7)
C330.5498 (4)−0.1817 (2)0.77863 (17)0.0458 (8)
H330.6106−0.22850.81320.055*
C340.5175 (4)−0.1916 (2)0.71435 (17)0.0421 (7)
C350.3806 (4)−0.0713 (2)0.60784 (16)0.0399 (7)
H35A0.4391−0.11580.58000.048*
H35B0.4158−0.00660.58310.048*
C360.1155 (5)−0.1129 (3)0.57916 (18)0.0500 (8)
C37−0.0493 (5)−0.0793 (3)0.59379 (19)0.0563 (10)
H37−0.1395−0.09790.58010.068*
C38−0.0586 (4)−0.0117 (2)0.63313 (17)0.0460 (8)
C390.4752 (5)−0.0416 (3)0.84147 (19)0.0584 (10)
H39A0.3668−0.04190.87130.088*
H39B0.49910.02510.81910.088*
H39C0.5599−0.07770.87190.088*
C400.5618 (5)−0.2776 (3)0.6837 (2)0.0649 (11)
H40A0.6226−0.25720.63490.097*
H40B0.4606−0.30170.68170.097*
H40C0.6307−0.32890.71480.097*
C41−0.2082 (4)0.0455 (3)0.6650 (2)0.0626 (10)
H41A−0.19360.11420.64890.094*
H41B−0.21950.02210.71790.094*
H41C−0.30780.03700.64870.094*
C420.2024 (6)−0.1860 (3)0.5398 (2)0.0785 (13)
H42A0.1201−0.21350.52500.118*
H42B0.2682−0.23770.57210.118*
H42C0.2750−0.15380.49690.118*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0376 (2)0.0323 (2)0.0349 (2)−0.00795 (15)0.00134 (15)−0.01615 (16)
O10.0608 (14)0.0458 (13)0.0427 (13)−0.0227 (11)0.0148 (10)−0.0259 (11)
O20.0507 (13)0.0455 (13)0.0336 (11)−0.0191 (10)−0.0007 (10)−0.0145 (10)
O30.0617 (16)0.097 (2)0.0567 (16)−0.0254 (15)0.0212 (13)−0.0440 (15)
N10.0346 (13)0.0295 (13)0.0404 (14)−0.0034 (10)−0.0027 (11)−0.0139 (11)
N20.0356 (13)0.0414 (15)0.0385 (14)−0.0040 (11)−0.0030 (11)−0.0194 (12)
N30.0348 (13)0.0370 (14)0.0362 (14)−0.0029 (11)−0.0027 (11)−0.0165 (11)
N40.0323 (13)0.0340 (14)0.0376 (14)−0.0051 (10)−0.0006 (10)−0.0177 (11)
N50.0357 (13)0.0326 (14)0.0345 (13)−0.0035 (11)−0.0020 (10)−0.0163 (11)
C10.0379 (16)0.0374 (18)0.0406 (18)−0.0018 (13)0.0015 (14)−0.0174 (14)
C20.063 (2)0.0390 (19)0.048 (2)−0.0130 (16)0.0105 (17)−0.0192 (16)
C30.077 (3)0.050 (2)0.041 (2)−0.0127 (19)0.0141 (18)−0.0141 (17)
C40.086 (3)0.061 (2)0.038 (2)−0.011 (2)0.0102 (19)−0.0263 (18)
C50.059 (2)0.047 (2)0.045 (2)−0.0056 (16)−0.0029 (16)−0.0253 (16)
C60.0333 (15)0.0375 (17)0.0376 (17)0.0010 (13)−0.0021 (13)−0.0183 (14)
C70.0384 (16)0.0320 (17)0.0451 (18)−0.0022 (13)−0.0041 (14)−0.0192 (14)
C80.0465 (18)0.0308 (17)0.0442 (18)−0.0072 (14)−0.0024 (14)−0.0161 (14)
C90.0390 (17)0.0402 (18)0.0432 (18)−0.0116 (14)−0.0002 (14)−0.0136 (14)
C100.0428 (18)0.0358 (18)0.0390 (18)−0.0015 (14)−0.0019 (14)−0.0118 (14)
C110.0400 (17)0.048 (2)0.0357 (17)−0.0046 (14)−0.0038 (14)−0.0143 (15)
C120.053 (2)0.046 (2)0.0403 (19)−0.0016 (16)−0.0098 (16)−0.0029 (15)
C130.0433 (18)0.0354 (18)0.0437 (19)−0.0035 (14)−0.0004 (14)−0.0091 (14)
C140.0330 (15)0.0406 (18)0.0350 (16)−0.0060 (13)0.0026 (12)−0.0170 (14)
C150.0515 (19)0.0305 (16)0.0286 (15)−0.0108 (14)−0.0057 (13)−0.0096 (13)
C160.0460 (18)0.0378 (18)0.0428 (18)−0.0151 (14)−0.0135 (14)−0.0102 (14)
C170.0350 (16)0.0322 (16)0.0351 (16)−0.0086 (12)−0.0045 (13)−0.0060 (13)
C180.0338 (17)0.056 (2)0.065 (2)−0.0071 (15)0.0011 (16)−0.0211 (18)
C190.068 (2)0.045 (2)0.049 (2)−0.0092 (17)−0.0047 (17)−0.0255 (17)
C200.077 (3)0.037 (2)0.065 (2)0.0064 (18)−0.012 (2)−0.0153 (18)
C210.075 (3)0.070 (3)0.048 (2)0.003 (2)−0.0165 (19)−0.0269 (19)
Cu20.0369 (2)0.0303 (2)0.0386 (2)−0.00238 (15)−0.00030 (16)−0.01353 (16)
O40.0543 (14)0.0409 (13)0.0459 (13)0.0047 (10)0.0116 (11)−0.0128 (11)
O50.0414 (12)0.0387 (13)0.0503 (14)−0.0092 (10)0.0020 (10)−0.0107 (11)
O60.110 (2)0.100 (2)0.0443 (17)0.0131 (19)0.0170 (16)−0.0155 (16)
N60.0402 (14)0.0340 (14)0.0420 (15)−0.0008 (11)−0.0076 (12)−0.0136 (12)
N70.0374 (13)0.0344 (14)0.0367 (14)−0.0028 (11)0.0001 (11)−0.0152 (11)
N80.0386 (13)0.0309 (14)0.0357 (14)−0.0014 (11)0.0007 (11)−0.0134 (11)
N90.0398 (14)0.0406 (15)0.0460 (16)−0.0069 (12)−0.0022 (12)−0.0174 (13)
N100.0486 (15)0.0388 (15)0.0401 (15)−0.0072 (12)−0.0071 (12)−0.0172 (12)
C220.0420 (18)0.0465 (19)0.0405 (18)−0.0009 (15)−0.0019 (14)−0.0221 (15)
C230.059 (2)0.054 (2)0.045 (2)0.0020 (17)0.0024 (17)−0.0157 (17)
C240.063 (2)0.073 (3)0.041 (2)−0.005 (2)0.0063 (17)−0.0198 (19)
C250.047 (2)0.086 (3)0.054 (2)−0.001 (2)0.0048 (17)−0.037 (2)
C260.0385 (18)0.060 (2)0.060 (2)0.0059 (16)−0.0076 (16)−0.0344 (19)
C270.0355 (16)0.0443 (19)0.0461 (19)−0.0036 (14)−0.0057 (14)−0.0236 (15)
C280.0411 (17)0.0375 (18)0.052 (2)0.0031 (14)−0.0102 (15)−0.0210 (15)
C290.054 (2)0.0316 (18)0.055 (2)−0.0013 (15)−0.0068 (16)−0.0094 (15)
C300.058 (2)0.044 (2)0.0414 (19)−0.0116 (16)−0.0104 (16)−0.0027 (15)
C310.058 (2)0.0383 (19)0.049 (2)−0.0148 (16)0.0031 (17)−0.0115 (16)
C320.0394 (17)0.0414 (18)0.0370 (17)−0.0038 (14)−0.0010 (14)−0.0113 (14)
C330.0531 (19)0.0360 (18)0.0392 (18)0.0032 (15)−0.0052 (15)−0.0036 (14)
C340.0483 (18)0.0292 (17)0.0415 (18)−0.0023 (14)0.0059 (15)−0.0081 (14)
C350.0447 (18)0.0381 (18)0.0370 (17)−0.0035 (14)0.0024 (14)−0.0164 (14)
C360.069 (2)0.046 (2)0.0407 (19)−0.0137 (18)−0.0169 (17)−0.0115 (16)
C370.070 (3)0.053 (2)0.055 (2)−0.0258 (19)−0.0263 (19)−0.0087 (18)
C380.0466 (19)0.044 (2)0.0429 (19)−0.0168 (15)−0.0091 (15)0.0009 (15)
C390.075 (3)0.056 (2)0.049 (2)−0.0026 (19)−0.0186 (19)−0.0198 (18)
C400.090 (3)0.038 (2)0.061 (2)0.0075 (19)−0.002 (2)−0.0203 (18)
C410.043 (2)0.072 (3)0.070 (3)−0.0163 (18)−0.0062 (18)−0.013 (2)
C420.111 (4)0.074 (3)0.072 (3)−0.012 (3)−0.021 (3)−0.046 (2)
Geometric parameters (Å, °) top
Cu1—O11.909 (2)Cu2—O41.905 (2)
Cu1—O21.950 (2)Cu2—O51.965 (2)
Cu1—N11.981 (2)Cu2—N61.977 (2)
Cu1—N42.051 (2)Cu2—N72.053 (2)
Cu1—N22.338 (2)Cu2—N92.311 (2)
O1—C11.302 (3)O4—C221.296 (3)
O2—C101.286 (4)O5—C311.289 (4)
O3—C101.221 (3)O6—C311.218 (4)
N1—C71.291 (4)N6—C281.286 (4)
N1—C81.466 (4)N6—C291.468 (4)
N2—C111.325 (4)N7—C321.330 (4)
N2—N31.377 (3)N7—N81.370 (3)
N3—C131.353 (4)N8—C341.357 (4)
N3—C141.439 (4)N8—C351.446 (4)
N4—C171.329 (3)N9—C381.328 (4)
N4—N51.371 (3)N9—N101.365 (3)
N5—C151.350 (3)N10—C361.353 (4)
N5—C141.449 (3)N10—C351.448 (4)
C1—C21.407 (4)C22—C231.406 (5)
C1—C61.422 (4)C22—C271.418 (4)
C2—C31.375 (4)C23—C241.372 (4)
C2—H20.930C23—H230.930
C3—C41.384 (5)C24—C251.386 (5)
C3—H30.930C24—H240.930
C4—C51.359 (5)C25—C261.358 (5)
C4—H40.930C25—H250.930
C5—C61.408 (4)C26—C271.415 (4)
C5—H50.930C26—H260.930
C6—C71.429 (4)C27—C281.427 (4)
C7—H70.930C28—H280.930
C8—C91.511 (4)C29—C301.518 (4)
C8—H8A0.970C29—H29A0.970
C8—H8B0.970C29—H29B0.970
C9—C101.511 (4)C30—C311.509 (5)
C9—H9A0.970C30—H30A0.970
C9—H9B0.970C30—H30B0.970
C11—C121.385 (4)C32—C331.388 (4)
C11—C211.502 (4)C32—C391.492 (4)
C12—C131.368 (4)C33—C341.367 (4)
C12—H120.930C33—H330.930
C13—C201.494 (4)C34—C401.494 (4)
C14—H14A0.970C35—H35A0.970
C14—H14B0.970C35—H35B0.970
C15—C161.367 (4)C36—C371.353 (5)
C15—C191.495 (4)C36—C421.492 (5)
C16—C171.397 (4)C37—C381.394 (5)
C16—H160.930C37—H370.930
C17—C181.489 (4)C38—C411.493 (5)
C18—H18A0.960C39—H39A0.960
C18—H18B0.960C39—H39B0.960
C18—H18C0.960C39—H39C0.960
C19—H19A0.960C40—H40A0.960
C19—H19B0.960C40—H40B0.960
C19—H19C0.960C40—H40C0.960
C20—H20A0.960C41—H41A0.960
C20—H20B0.960C41—H41B0.960
C20—H20C0.960C41—H41C0.960
C21—H21A0.960C42—H42A0.960
C21—H21B0.960C42—H42B0.960
C21—H21C0.960C42—H42C0.960
O1—Cu1—O2167.05 (10)O4—Cu2—O5169.07 (10)
O1—Cu1—N192.36 (9)O4—Cu2—N692.37 (10)
O2—Cu1—N191.07 (9)O5—Cu2—N690.98 (10)
O1—Cu1—N488.32 (9)O4—Cu2—N786.25 (9)
O2—Cu1—N485.65 (9)O5—Cu2—N788.24 (9)
N1—Cu1—N4167.45 (9)N6—Cu2—N7167.58 (10)
O1—Cu1—N295.31 (9)O4—Cu2—N997.73 (10)
O2—Cu1—N295.79 (9)O5—Cu2—N991.56 (9)
N1—Cu1—N2105.47 (9)N6—Cu2—N9103.91 (9)
N4—Cu1—N286.93 (9)N7—Cu2—N988.50 (9)
C1—O1—Cu1128.68 (19)C22—O4—Cu2129.5 (2)
C10—O2—Cu1124.47 (19)C31—O5—Cu2119.3 (2)
C7—N1—C8117.1 (2)C28—N6—C29118.0 (3)
C7—N1—Cu1124.5 (2)C28—N6—Cu2124.4 (2)
C8—N1—Cu1118.30 (18)C29—N6—Cu2117.6 (2)
C11—N2—N3104.3 (2)C32—N7—N8105.7 (2)
C11—N2—Cu1133.2 (2)C32—N7—Cu2130.5 (2)
N3—N2—Cu1114.78 (16)N8—N7—Cu2120.62 (18)
C13—N3—N2111.9 (2)C34—N8—N7111.1 (2)
C13—N3—C14129.8 (2)C34—N8—C35128.9 (2)
N2—N3—C14118.2 (2)N7—N8—C35119.4 (2)
C17—N4—N5105.5 (2)C38—N9—N10105.1 (2)
C17—N4—Cu1130.58 (19)C38—N9—Cu2136.6 (2)
N5—N4—Cu1123.80 (17)N10—N9—Cu2117.74 (18)
C15—N5—N4111.2 (2)C36—N10—N9111.8 (3)
C15—N5—C14129.2 (2)C36—N10—C35129.4 (3)
N4—N5—C14119.4 (2)N9—N10—C35118.8 (2)
O1—C1—C2119.3 (3)O4—C22—C23118.9 (3)
O1—C1—C6123.5 (3)O4—C22—C27123.6 (3)
C2—C1—C6117.2 (3)C23—C22—C27117.4 (3)
C3—C2—C1121.3 (3)C24—C23—C22121.3 (3)
C3—C2—H2119.4C24—C23—H23119.3
C1—C2—H2119.4C22—C23—H23119.3
C2—C3—C4121.2 (3)C23—C24—C25121.4 (4)
C2—C3—H3119.4C23—C24—H24119.3
C4—C3—H3119.4C25—C24—H24119.3
C5—C4—C3119.1 (3)C26—C25—C24118.8 (3)
C5—C4—H4120.4C26—C25—H25120.6
C3—C4—H4120.4C24—C25—H25120.6
C4—C5—C6121.7 (3)C25—C26—C27121.9 (3)
C4—C5—H5119.1C25—C26—H26119.0
C6—C5—H5119.1C27—C26—H26119.0
C5—C6—C1119.5 (3)C26—C27—C22119.1 (3)
C5—C6—C7117.6 (3)C26—C27—C28118.2 (3)
C1—C6—C7122.9 (3)C22—C27—C28122.6 (3)
N1—C7—C6126.8 (3)N6—C28—C27127.4 (3)
N1—C7—H7116.6N6—C28—H28116.3
C6—C7—H7116.6C27—C28—H28116.3
N1—C8—C9111.8 (2)N6—C29—C30111.4 (3)
N1—C8—H8A109.2N6—C29—H29A109.3
C9—C8—H8A109.2C30—C29—H29A109.3
N1—C8—H8B109.2N6—C29—H29B109.3
C9—C8—H8B109.2C30—C29—H29B109.3
H8A—C8—H8B107.9H29A—C29—H29B108.0
C8—C9—C10114.0 (3)C31—C30—C29114.4 (3)
C8—C9—H9A108.7C31—C30—H30A108.7
C10—C9—H9A108.7C29—C30—H30A108.7
C8—C9—H9B108.7C31—C30—H30B108.7
C10—C9—H9B108.7C29—C30—H30B108.7
H9A—C9—H9B107.6H30A—C30—H30B107.6
O3—C10—O2123.0 (3)O6—C31—O5123.6 (3)
O3—C10—C9119.9 (3)O6—C31—C30119.1 (3)
O2—C10—C9117.1 (3)O5—C31—C30117.3 (3)
N2—C11—C12111.3 (3)N7—C32—C33110.0 (3)
N2—C11—C21120.0 (3)N7—C32—C39121.5 (3)
C12—C11—C21128.7 (3)C33—C32—C39128.5 (3)
C13—C12—C11106.8 (3)C34—C33—C32107.2 (3)
C13—C12—H12126.6C34—C33—H33126.4
C11—C12—H12126.6C32—C33—H33126.4
N3—C13—C12105.7 (3)N8—C34—C33106.0 (3)
N3—C13—C20123.4 (3)N8—C34—C40123.9 (3)
C12—C13—C20130.9 (3)C33—C34—C40130.0 (3)
N3—C14—N5111.7 (2)N8—C35—N10111.8 (2)
N3—C14—H14A109.3N8—C35—H35A109.3
N5—C14—H14A109.3N10—C35—H35A109.3
N3—C14—H14B109.3N8—C35—H35B109.3
N5—C14—H14B109.3N10—C35—H35B109.3
H14A—C14—H14B107.9H35A—C35—H35B107.9
N5—C15—C16106.6 (2)N10—C36—C37105.8 (3)
N5—C15—C19123.1 (3)N10—C36—C42122.2 (3)
C16—C15—C19130.3 (3)C37—C36—C42131.9 (3)
C15—C16—C17106.4 (3)C36—C37—C38107.3 (3)
C15—C16—H16126.8C36—C37—H37126.3
C17—C16—H16126.8C38—C37—H37126.3
N4—C17—C16110.2 (3)N9—C38—C37109.9 (3)
N4—C17—C18121.1 (3)N9—C38—C41119.8 (3)
C16—C17—C18128.6 (3)C37—C38—C41130.3 (3)
C17—C18—H18A109.5C32—C39—H39A109.5
C17—C18—H18B109.5C32—C39—H39B109.5
H18A—C18—H18B109.5H39A—C39—H39B109.5
C17—C18—H18C109.5C32—C39—H39C109.5
H18A—C18—H18C109.5H39A—C39—H39C109.5
H18B—C18—H18C109.5H39B—C39—H39C109.5
C15—C19—H19A109.5C34—C40—H40A109.5
C15—C19—H19B109.5C34—C40—H40B109.5
H19A—C19—H19B109.5H40A—C40—H40B109.5
C15—C19—H19C109.5C34—C40—H40C109.5
H19A—C19—H19C109.5H40A—C40—H40C109.5
H19B—C19—H19C109.5H40B—C40—H40C109.5
C13—C20—H20A109.5C38—C41—H41A109.5
C13—C20—H20B109.5C38—C41—H41B109.5
H20A—C20—H20B109.5H41A—C41—H41B109.5
C13—C20—H20C109.5C38—C41—H41C109.5
H20A—C20—H20C109.5H41A—C41—H41C109.5
H20B—C20—H20C109.5H41B—C41—H41C109.5
C11—C21—H21A109.5C36—C42—H42A109.5
C11—C21—H21B109.5C36—C42—H42B109.5
H21A—C21—H21B109.5H42A—C42—H42B109.5
C11—C21—H21C109.5C36—C42—H42C109.5
H21A—C21—H21C109.5H42A—C42—H42C109.5
H21B—C21—H21C109.5H42B—C42—H42C109.5
Table 1
Selected geometric parameters (Å, °) top
Cu1—O11.909 (2)Cu1—N42.051 (2)
Cu1—O21.950 (2)Cu1—N22.338 (2)
Cu1—N11.981 (2)
O1—Cu1—O2167.05 (10)N1—Cu1—N4167.45 (9)
O1—Cu1—N192.36 (9)O1—Cu1—N295.31 (9)
O2—Cu1—N191.07 (9)O2—Cu1—N295.79 (9)
O1—Cu1—N488.32 (9)N1—Cu1—N2105.47 (9)
O2—Cu1—N485.65 (9)N4—Cu1—N286.93 (9)
Acknowledgements top

This research was supported by the National Sciences Foundation of China (grant No. 20676057).

references
References top

Bruker (2000). SMART (Version 5.625) and SAINT (Version 6.3). Bruker AXS Inc., Madison, Wisconsin, USA.

Plesch, G., Friebel, C., Warda, S. A., Sivý, J. & Švajlenová, O. (1997). Transition Met. Chem. 22, 433–440.

Raso, A. G., Fiol, J. J., Badenas, F. & Quiros, M. (1996). Polyhedron, 18, 4407–4413.

Raso, A. G., Fiol, J. J., Zafra, A. L., Cabrero, A., Mata, I. & Molins, E. (1999). Polyhedron, 18, 871–878.

Reddy, P. A. N., Nethaji, M. & Chakravarty, A. R. (2002). Inorg. Chim. Acta, 337, 450–458.

Sheldrick, G. M. (1996). SADABS. Version 2.10. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Sheldrick, G. M. (2000). SHELXTL. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Wang, M. Z., Cai, G. L., Meng, Z. X. & Liu, B. L. (2005). J. Chem. Cryst. 35, 43–47.

Warda, S. A. (1997). Acta Cryst. C53, 1759–1761.

Warda, S. A. (1998a). Acta Cryst. C54, 187–189.

Warda, S. A. (1998b). Acta Cryst. C54, 768–770.

Warda, S. A. (1998c). Acta Cryst. C54, 1754–1755.