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Acta Cryst. (2008). E64, m1250-m1251    [ doi:10.1107/S1600536808028134 ]

(Imidazole-[kappa]N3){N-[1-(2-oxidophenyl)ethylidene]-L-valinato-[kappa]3O,N,O'}copper(II)

G.-Q. Zhao, Q.-R. Liu, W.-C. Yang, S.-T. Li and X. Wang

Abstract top

In each of the two independent molecules in the asymmetric unit of the title compound, [Cu(C13H15NO3)(C3H4N2)], the CuII atom is four-coordinated by two O atoms and the N atom of the tridentate Schiff base ligand and one N atom from the imidazole ligand in a distorted square-planar geometry. In the crystal structure, molecules are linked by intermolecular N-H...O hydrogen bonds.

Comment top

In the past decades, significant progress has been achieved in understanding the chemistry of transition metal complexes with Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, and α-amino acids (Vigato & Tamburini, 2004; Ganguly et al., 2008; Casella & Guillotti, 1983). A few stuctural studies have been performed on Schiff base complexes derived from 2-hydroxyacetophenone and animo acids (Usman et al., 2003; Basu Baul et al., 2007; Parekh et al., 2006). We report here the crystal structure of the title CuII complex, (I).

In the title compound (I), the asymmetric unit contains two independent molecules (Fig. 1). The structure consists of discrete monomeric square-planar CuII complex (Table 1). The four 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 imidazole ligand. In the molecules with Cu1 and Cu2, the nitrogen heterocycles are planar and they form the angles of 4.2 (2) and 6.0 (2)° with the C1—C6 and C17–C32 rings, respectively.

The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds (Fig. 2 and Table 2), which the H atom attached to N3 is hydrogen-bonded to the neighboring carboxylate oxygen O6.

Related literature top

For related literature, see: Basu Baul et al. (2007); Casella & Guillotti (1983); Ganguly et al. (2008); Parekh et al. (2006); Plesch et al. (1997); Usman et al. (2003); Vigato & Tamburini (2004).

Experimental top

The title compound was synthesized as described in the literature (Plesch et al., 1997). To L-valine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol was added 2-hydroxyacetophenone (1.00 mmol in 10 ml of methanol) dropwise. The yellow solution was stirred for 2.0 h at 333 K. The resultant mixture was added dropwise to copper(II) acetate monohydrate (1.00 mmol) and imidazole (1.00 mmol) in an aqueous methanolic solution (20 ml, 1:1 v/v), and heated with stirring for 2.0 h at 333 K. The dark blue solution was filtered and left for several days, dark blue crystals had formed that were filtered off, washed with water, and dried under vacuum.

Refinement top

All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 or 0.98 Å (CH) and Uiso(H) = 1.2Ueq(C), with C—H = 0.96 Å (CH3) and Uiso(H) = 1.5Ueq(C), and with N—H = 0.86 Å (NH) and Uiso(H) = 1.2Ueq(N).

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, 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
[Figure 1] Fig. 1. The structure of the title compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. For clarity, H atoms have been omitted.
[Figure 2] Fig. 2. A view of the crystal packing of (I) along the a axis. Hydrogen bonds are shown as dashed lines.
(Imidazole-κN3){N-[1-(2-oxidophenyl)ethylidene]-L-valinato- κ3O,N,O'}copper(II) top
Crystal data top
[Cu(C13H15NO3)(C3H4N2)]F(000) = 1512
Mr = 364.88Dx = 1.484 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4789 reflections
a = 12.2025 (13) Åθ = 2.3–23.6°
b = 13.5248 (14) ŵ = 1.36 mm−1
c = 19.791 (2) ÅT = 296 K
V = 3266.2 (6) Å3Block, dark blue
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		5764 independent reflections
Radiation source: fine-focus sealed tube4619 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.687, Tmax = 0.773k = −14→16
17018 measured reflectionsl = −23→21
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0297P)2 + 1.2486P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5764 reflectionsΔρmax = 0.33 e Å−3
421 parametersΔρmin = −0.50 e Å−3
0 restraintsAbsolute structure: Flack (1983), 2509 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.004 (13)
Crystal data top
[Cu(C13H15NO3)(C3H4N2)]V = 3266.2 (6) Å3
Mr = 364.88Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 12.2025 (13) ŵ = 1.36 mm−1
b = 13.5248 (14) ÅT = 296 K
c = 19.791 (2) Å0.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		5764 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4619 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.773Rint = 0.031
17018 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.33 e Å−3
S = 1.03Δρmin = −0.50 e Å−3
5764 reflectionsAbsolute structure: Flack (1983), 2509 Freidel pairs
421 parametersFlack parameter: 0.004 (13)
0 restraints
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
Cu10.52180 (4)0.63527 (4)0.08491 (2)0.04826 (14)
Cu20.65002 (3)0.85812 (4)0.60823 (2)0.04751 (14)
C10.6063 (3)0.6039 (3)−0.0474 (2)0.0532 (11)
C20.5832 (4)0.5745 (4)−0.1145 (2)0.0655 (13)
H20.51060.5699−0.12840.079*
C30.6650 (5)0.5528 (4)−0.1596 (2)0.0745 (14)
H30.64740.5333−0.20330.089*
C40.7750 (4)0.5597 (4)−0.1401 (3)0.0738 (15)
H40.83100.5448−0.17030.089*
C50.7979 (4)0.5886 (3)−0.0761 (3)0.0624 (12)
H50.87110.5944−0.06370.075*
C60.7169 (3)0.6106 (3)−0.0269 (2)0.0506 (11)
C70.7512 (3)0.6428 (3)0.0404 (2)0.0515 (10)
C80.7081 (3)0.6986 (3)0.1538 (2)0.0490 (10)
H80.78130.67520.16650.059*
C90.6246 (3)0.6621 (3)0.2057 (2)0.0503 (11)
C100.8720 (3)0.6564 (4)0.0537 (2)0.0719 (15)
H10A0.90150.70310.02210.108*
H10B0.90880.59410.04870.108*
H10C0.88240.68050.09890.108*
C110.7088 (4)0.8124 (3)0.1499 (2)0.0636 (13)
H110.75500.82990.11120.076*
C120.5957 (4)0.8557 (4)0.1357 (3)0.0809 (15)
H12A0.54760.84130.17280.121*
H12B0.56670.82700.09510.121*
H12C0.60150.92600.13020.121*
C130.7593 (5)0.8599 (5)0.2100 (3)0.1054 (19)
H13A0.71270.85030.24860.158*
H13B0.76810.92940.20170.158*
H13C0.82960.83060.21850.158*
C140.2976 (3)0.6635 (3)0.1369 (2)0.0558 (12)
H140.32330.68750.17800.067*
C150.1879 (3)0.6175 (3)0.0578 (2)0.0567 (12)
H150.12510.60300.03310.068*
C160.2909 (3)0.6085 (3)0.0364 (2)0.0524 (11)
H160.31200.5863−0.00610.063*
C170.5693 (3)0.8710 (3)0.47462 (19)0.0457 (9)
C180.5908 (3)0.8916 (3)0.4066 (2)0.0539 (11)
H180.66330.89480.39230.065*
C190.5093 (4)0.9074 (3)0.3601 (2)0.0606 (12)
H190.52690.92130.31540.073*
C200.4009 (4)0.9024 (3)0.3801 (3)0.0625 (13)
H200.34490.91500.34940.075*
C210.3770 (3)0.8788 (3)0.4455 (2)0.0584 (12)
H210.30370.87420.45790.070*
C220.4572 (3)0.8610 (3)0.49521 (18)0.0433 (9)
C230.4247 (3)0.8301 (3)0.5626 (2)0.0444 (10)
C240.4742 (3)0.7757 (3)0.67720 (18)0.0465 (9)
H240.39680.78690.68810.056*
C250.5459 (3)0.8289 (3)0.7284 (2)0.0537 (12)
C260.3039 (3)0.8159 (3)0.5762 (2)0.0554 (11)
H26A0.29350.79650.62250.083*
H26B0.27560.76530.54700.083*
H26C0.26570.87670.56790.083*
C270.4998 (3)0.6645 (3)0.6814 (2)0.0556 (11)
H270.48950.64490.72860.067*
C280.6189 (4)0.6388 (4)0.6627 (2)0.0792 (14)
H28A0.63100.56940.66950.119*
H28B0.66810.67580.69090.119*
H28C0.63190.65520.61620.119*
C290.4234 (4)0.6023 (4)0.6399 (3)0.0898 (18)
H29A0.34910.61610.65270.135*
H29B0.43900.53360.64750.135*
H29C0.43330.61740.59290.135*
C300.8785 (3)0.8880 (3)0.5586 (2)0.0519 (11)
H300.85810.89660.51370.062*
C310.9781 (3)0.8710 (3)0.64947 (17)0.0363 (8)
H311.03700.86540.67910.044*
C320.8746 (3)0.8686 (4)0.6653 (2)0.0588 (11)
H320.84920.86080.70930.071*
N10.6788 (2)0.6579 (2)0.08787 (16)0.0469 (8)
N20.3602 (2)0.6369 (3)0.08634 (15)0.0482 (7)
N30.1914 (2)0.6513 (3)0.12130 (17)0.0559 (9)
H3A0.13620.66300.14710.067*
N40.4983 (2)0.8161 (2)0.60987 (17)0.0437 (7)
N50.8097 (2)0.8782 (2)0.61290 (16)0.0478 (8)
N60.9835 (3)0.8827 (3)0.5834 (3)0.0933 (16)
H61.04260.88650.55990.112*
O10.5208 (2)0.6222 (2)−0.00899 (13)0.0623 (8)
O20.52949 (19)0.6399 (2)0.18300 (12)0.0534 (7)
O30.6509 (2)0.6600 (3)0.26604 (14)0.0701 (10)
O40.65434 (19)0.8605 (3)0.51391 (13)0.0631 (8)
O50.6344 (2)0.8681 (3)0.70602 (13)0.0640 (8)
O60.5198 (2)0.8268 (3)0.78876 (14)0.0691 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0364 (2)0.0606 (3)0.0478 (3)0.0005 (3)0.0044 (2)0.0034 (3)
Cu20.0345 (2)0.0625 (3)0.0455 (3)−0.0071 (2)−0.0017 (2)−0.0016 (3)
C10.056 (2)0.056 (3)0.048 (3)0.008 (2)0.010 (2)0.009 (2)
C20.060 (3)0.084 (3)0.053 (3)0.004 (2)0.005 (2)0.008 (3)
C30.099 (4)0.077 (3)0.047 (3)0.001 (3)0.013 (3)0.003 (2)
C40.075 (3)0.075 (4)0.071 (4)0.011 (3)0.028 (3)0.005 (3)
C50.051 (2)0.064 (3)0.072 (3)0.002 (2)0.015 (2)0.007 (3)
C60.045 (2)0.051 (3)0.055 (3)0.0040 (19)0.0146 (19)0.0125 (19)
C70.043 (2)0.051 (3)0.060 (3)0.007 (2)0.0099 (19)0.012 (3)
C80.0331 (19)0.061 (3)0.053 (3)0.0006 (19)0.0002 (18)0.013 (2)
C90.042 (2)0.059 (3)0.050 (3)0.0055 (19)0.0032 (19)0.006 (2)
C100.037 (2)0.109 (4)0.069 (3)0.006 (3)0.015 (2)0.016 (3)
C110.055 (3)0.063 (3)0.072 (3)−0.011 (2)−0.013 (2)0.003 (2)
C120.079 (3)0.057 (3)0.107 (4)0.008 (3)−0.033 (3)−0.003 (3)
C130.117 (5)0.098 (4)0.102 (4)−0.018 (4)−0.044 (4)0.000 (4)
C140.041 (2)0.078 (3)0.049 (2)0.001 (2)0.0043 (19)−0.005 (2)
C150.043 (2)0.080 (3)0.047 (2)0.001 (2)−0.0065 (19)−0.002 (2)
C160.048 (2)0.069 (3)0.040 (2)0.000 (2)−0.0019 (19)−0.002 (2)
C170.043 (2)0.049 (2)0.046 (2)0.003 (2)−0.0036 (18)−0.004 (2)
C180.046 (2)0.069 (3)0.046 (3)0.002 (2)−0.0026 (19)0.000 (2)
C190.066 (3)0.064 (3)0.051 (3)0.001 (2)0.000 (2)0.004 (2)
C200.056 (3)0.076 (3)0.056 (3)0.000 (2)−0.014 (2)0.011 (2)
C210.041 (2)0.071 (3)0.064 (3)0.000 (2)−0.006 (2)0.001 (2)
C220.0382 (19)0.048 (2)0.044 (2)−0.001 (2)−0.0069 (16)−0.003 (2)
C230.0374 (19)0.047 (3)0.049 (2)−0.0028 (17)0.0002 (18)−0.0089 (18)
C240.0325 (18)0.062 (3)0.045 (2)−0.0064 (19)0.0031 (18)−0.0033 (19)
C250.034 (2)0.076 (3)0.050 (3)−0.003 (2)−0.0044 (19)−0.005 (2)
C260.034 (2)0.077 (3)0.054 (3)−0.003 (2)−0.0013 (19)−0.006 (2)
C270.054 (2)0.065 (3)0.048 (2)−0.004 (2)0.0015 (19)0.003 (2)
C280.074 (3)0.082 (3)0.081 (3)0.021 (3)0.018 (3)0.012 (3)
C290.105 (4)0.074 (4)0.091 (4)−0.012 (3)−0.018 (3)−0.003 (3)
C300.041 (2)0.068 (3)0.047 (2)−0.009 (2)−0.0002 (18)−0.006 (2)
C310.0283 (17)0.053 (2)0.0273 (18)−0.003 (2)−0.0090 (15)0.0052 (19)
C320.052 (2)0.075 (3)0.049 (2)−0.013 (3)−0.005 (2)0.016 (3)
N10.0393 (17)0.054 (2)0.0472 (19)−0.0001 (15)0.0052 (15)0.0091 (17)
N20.0408 (16)0.060 (2)0.0439 (18)−0.0004 (18)0.0032 (14)−0.001 (2)
N30.0388 (17)0.076 (3)0.053 (2)0.0006 (19)0.0066 (15)−0.001 (2)
N40.0353 (16)0.0518 (19)0.0440 (18)−0.0038 (14)−0.0009 (14)−0.0054 (15)
N50.0383 (16)0.060 (2)0.0451 (18)−0.0067 (17)0.0001 (15)0.0047 (18)
N60.047 (2)0.083 (3)0.149 (5)−0.002 (2)0.002 (3)−0.024 (3)
O10.0461 (15)0.095 (2)0.0457 (16)0.0086 (19)0.0045 (13)0.0038 (16)
O20.0373 (13)0.0749 (18)0.0479 (15)−0.0075 (18)0.0039 (12)0.0035 (16)
O30.0458 (15)0.115 (3)0.0492 (18)−0.0072 (18)−0.0004 (14)0.0161 (18)
O40.0356 (13)0.107 (2)0.0465 (16)−0.003 (2)−0.0004 (12)−0.0003 (18)
O50.0450 (15)0.096 (2)0.0507 (17)−0.019 (2)−0.0016 (13)−0.0106 (18)
O60.0445 (15)0.121 (3)0.0417 (18)−0.0093 (17)0.0043 (14)−0.0130 (16)
Geometric parameters (Å, °) top
Cu1—O11.867 (3)C15—H150.9300
Cu1—N11.941 (3)C16—N21.356 (5)
Cu1—O21.945 (2)C16—H160.9300
Cu1—N21.972 (3)C17—O41.304 (4)
Cu2—O41.868 (3)C17—C181.399 (5)
Cu2—N41.937 (3)C17—C221.433 (5)
Cu2—O51.949 (3)C18—C191.371 (5)
Cu2—N51.969 (3)C18—H180.9300
C1—O11.314 (5)C19—C201.383 (6)
C1—C61.412 (6)C19—H190.9300
C1—C21.415 (6)C20—C211.363 (6)
C2—C31.371 (6)C20—H200.9300
C2—H20.9300C21—C221.409 (5)
C3—C41.399 (7)C21—H210.9300
C3—H30.9300C22—C231.453 (5)
C4—C51.355 (6)C23—N41.311 (5)
C4—H40.9300C23—C261.511 (5)
C5—C61.419 (6)C24—N41.470 (5)
C5—H50.9300C24—C251.520 (5)
C6—C71.464 (6)C24—C271.539 (6)
C7—N11.305 (4)C24—H240.9800
C7—C101.508 (5)C25—O61.236 (5)
C8—N11.461 (5)C25—O51.282 (4)
C8—C91.528 (5)C26—H26A0.9600
C8—C111.541 (6)C26—H26B0.9600
C8—H80.9800C26—H26C0.9600
C9—O31.237 (5)C27—C291.500 (6)
C9—O21.281 (4)C27—C281.539 (6)
C10—H10A0.9600C27—H270.9800
C10—H10B0.9600C28—H28A0.9600
C10—H10C0.9600C28—H28B0.9600
C11—C131.484 (6)C28—H28C0.9600
C11—C121.526 (6)C29—H29A0.9600
C11—H110.9800C29—H29B0.9600
C12—H12A0.9600C29—H29C0.9600
C12—H12B0.9600C30—N51.370 (5)
C12—H12C0.9600C30—N61.375 (5)
C13—H13A0.9600C30—H300.9300
C13—H13B0.9600C31—C321.302 (5)
C13—H13C0.9600C31—N61.319 (5)
C14—N21.310 (5)C31—H310.9300
C14—N31.343 (5)C32—N51.311 (5)
C14—H140.9300C32—H320.9300
C15—C161.332 (5)N3—H3A0.8600
C15—N31.338 (5)N6—H60.8600
O1—Cu1—N192.94 (13)C19—C18—H18118.6
O1—Cu1—O2175.69 (13)C17—C18—H18118.6
N1—Cu1—O285.25 (12)C18—C19—C20119.6 (4)
O1—Cu1—N290.51 (12)C18—C19—H19120.2
N1—Cu1—N2169.97 (14)C20—C19—H19120.2
O2—Cu1—N291.92 (11)C21—C20—C19119.2 (4)
O4—Cu2—N492.79 (13)C21—C20—H20120.4
O4—Cu2—O5173.64 (14)C19—C20—H20120.4
N4—Cu2—O584.85 (12)C20—C21—C22123.7 (4)
O4—Cu2—N590.96 (12)C20—C21—H21118.2
N4—Cu2—N5170.17 (14)C22—C21—H21118.2
O5—Cu2—N592.32 (12)C21—C22—C17116.6 (3)
O1—C1—C6125.5 (4)C21—C22—C23120.1 (3)
O1—C1—C2116.0 (4)C17—C22—C23123.3 (3)
C6—C1—C2118.5 (4)N4—C23—C22120.7 (3)
C3—C2—C1121.8 (5)N4—C23—C26121.5 (4)
C3—C2—H2119.1C22—C23—C26117.8 (3)
C1—C2—H2119.1N4—C24—C25108.3 (3)
C2—C3—C4120.3 (5)N4—C24—C27111.8 (3)
C2—C3—H3119.9C25—C24—C27108.0 (3)
C4—C3—H3119.9N4—C24—H24109.6
C5—C4—C3118.4 (5)C25—C24—H24109.6
C5—C4—H4120.8C27—C24—H24109.6
C3—C4—H4120.8O6—C25—O5124.1 (4)
C4—C5—C6123.9 (5)O6—C25—C24119.0 (4)
C4—C5—H5118.0O5—C25—C24116.7 (4)
C6—C5—H5118.0C23—C26—H26A109.5
C1—C6—C5117.1 (4)C23—C26—H26B109.5
C1—C6—C7123.6 (4)H26A—C26—H26B109.5
C5—C6—C7119.2 (4)C23—C26—H26C109.5
N1—C7—C6120.6 (3)H26A—C26—H26C109.5
N1—C7—C10121.1 (4)H26B—C26—H26C109.5
C6—C7—C10118.3 (3)C29—C27—C28109.2 (4)
N1—C8—C9108.3 (3)C29—C27—C24113.1 (4)
N1—C8—C11109.5 (3)C28—C27—C24113.6 (4)
C9—C8—C11111.1 (4)C29—C27—H27106.8
N1—C8—H8109.3C28—C27—H27106.8
C9—C8—H8109.3C24—C27—H27106.8
C11—C8—H8109.3C27—C28—H28A109.5
O3—C9—O2124.6 (4)C27—C28—H28B109.5
O3—C9—C8118.9 (4)H28A—C28—H28B109.5
O2—C9—C8116.4 (4)C27—C28—H28C109.5
C7—C10—H10A109.5H28A—C28—H28C109.5
C7—C10—H10B109.5H28B—C28—H28C109.5
H10A—C10—H10B109.5C27—C29—H29A109.5
C7—C10—H10C109.5H29A—C29—H29C109.5
H10A—C10—H10C109.5H29B—C29—H29C109.5
H10B—C10—H10C109.5N5—C30—N6106.6 (4)
C13—C11—C12111.0 (4)N5—C30—H30126.7
C13—C11—C8113.2 (4)N6—C30—H30126.7
C12—C11—C8112.8 (4)C32—C31—N6106.9 (3)
C13—C11—H11106.5C32—C31—H31126.6
C12—C11—H11106.5N6—C31—H31126.6
C8—C11—H11106.5C31—C32—N5113.2 (4)
C11—C12—H12A109.5C31—C32—H32123.4
C11—C12—H12B109.5N5—C32—H32123.4
H12A—C12—H12B109.5C7—N1—C8122.4 (3)
C11—C12—H12C109.5C7—N1—Cu1128.4 (3)
H12A—C12—H12C109.5C8—N1—Cu1109.1 (2)
H12B—C12—H12C109.5C14—N2—C16105.8 (3)
C11—C13—H13A109.5C14—N2—Cu1126.6 (3)
C11—C13—H13B109.5C16—N2—Cu1127.6 (3)
H13A—C13—H13B109.5C15—N3—C14106.8 (3)
C11—C13—H13C109.5C15—N3—H3A126.6
H13A—C13—H13C109.5C14—N3—H3A126.6
H13B—C13—H13C109.5C23—N4—C24124.3 (3)
N2—C14—N3110.7 (4)C23—N4—Cu2126.9 (3)
N2—C14—H14124.7C24—N4—Cu2108.4 (2)
N3—C14—H14124.7C32—N5—C30105.1 (3)
C16—C15—N3107.5 (4)C32—N5—Cu2128.4 (3)
C16—C15—H15126.3C30—N5—Cu2125.6 (3)
N3—C15—H15126.3C31—N6—C30108.3 (4)
C15—C16—N2109.3 (4)C31—N6—H6125.9
C15—C16—H16125.3C30—N6—H6125.9
N2—C16—H16125.3C1—O1—Cu1126.0 (3)
O4—C17—C18116.5 (3)C9—O2—Cu1113.6 (2)
O4—C17—C22125.4 (3)C17—O4—Cu2125.1 (2)
C18—C17—C22118.1 (3)C25—O5—Cu2113.4 (2)
C19—C18—C17122.7 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O6i0.861.912.764 (4)172.
Symmetry codes: (i) x−1/2, −y+3/2, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Cu1—O11.867 (3)Cu2—O41.868 (3)
Cu1—N11.941 (3)Cu2—N41.937 (3)
Cu1—O21.945 (2)Cu2—O51.949 (3)
Cu1—N21.972 (3)Cu2—N51.969 (3)
O1—Cu1—N192.94 (13)O4—Cu2—N492.79 (13)
O1—Cu1—O2175.69 (13)O4—Cu2—O5173.64 (14)
N1—Cu1—O285.25 (12)N4—Cu2—O584.85 (12)
O1—Cu1—N290.51 (12)O4—Cu2—N590.96 (12)
N1—Cu1—N2169.97 (14)N4—Cu2—N5170.17 (14)
O2—Cu1—N291.92 (11)O5—Cu2—N592.32 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O6i0.861.912.764 (4)172.
Symmetry codes: (i) x−1/2, −y+3/2, −z+1.
Acknowledgements top

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

references
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