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hy2148 scheme

Acta Cryst. (2008). E64, m1111-m1112    [ doi:10.1107/S1600536808024252 ]

Bis(2,2'-bipyridine-[kappa]2N,N')(4-methylbenzoato-[kappa]2O,O')copper(II) iodide hemihydrate

C.-M. Tang and G.-H. Deng

Abstract top

The title compound, [Cu(C8H7O2)(C10H8N2)2]I·0.5H2O, was obtained by the hydrothermal reaction of copper(I) iodide, 4-methylbenzoic acid and 2,2'-bipyridine. The initial reactant of CuI was oxidized to CuII. The asymmetric unit contains two independent complex molecules, two I- ions and one water molecule. Each CuII atom is coordinated by two O atoms from a 4-methylbenzoate ligand and four N atoms from two 2,2'-bipyridine ligands, displaying a distorted octahedral geometry. The structure involves O-H...I hydrogen bonds between the water molecule and iodide ions and [pi]-[pi] stacking interactions between the benzene and pyridyl rings [centroid-centroid distance = 3.79 (1) Å] and between the pyridyl rings [centroid-centroid distance = 3.87 (1) Å].

Comment top

As a building block, 4-methylbenzoate ligand is an excellent candidate for the construction of supramolecular complexes (Ma & Deng, 2008; Song et al., 2008a,b,c,d). Recently, we obtained the title mononuclear complex by the hydrothermal reaction of CuI, 4-methylbenzoic acid and 2,2'-bipyridine.

As illustrated in Fig. 1, the asymmetric unit of the title compound contains two independent complex molecules, two I ions and one lattice water molecule. Each CuII atom has a distorted octahedral coordination geometry, involving two carboxylate O atoms from one 4-methylbenzoate ligand, and four N atoms from two 2,2'-bipyridine ligands. One Cu—O distance is distinctly longer than the others for each CuII atom (Table 1), but still within the range of a significant interaction (Mao et al. 2001). Judged from the blue crystals, the initial reactant of CuI was thus oxidated to CuII in the hydrothermal reaction. The structure involves O—H···I hydrogen bonds between the water molecule and I ions (Table 2) and π–π stacking interactions (Fig. 2). The centroid–centroid distances are 3.79 (1)Å between the adjacent phenyl and pyridyl rings, and 3.87 (1)Å between the adjacent pyridyl rings.

Related literature top

For related literature, see: Ma & Deng (2008); Mao et al. (2001); Song et al. (2008a,b,c,d).

Experimental top

A mixture of CuI (0.1 g, 0.5 mmol), 4-methylbenzoic acid (0.068 g, 0.5 mmol), 2,2'-bipyridine (0.078 g, 0.5 mmol) and H2O (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 433 K for 3 d and then cooled to room temperature at a rate of 10 K h-1. Block colorless crystals were obtained.

Refinement top

C-bound H atoms were positioned geometrically and refined as riding, with C—H = 0.93 (CH) and 0.96 (CH3) Å, and with Uiso(H) = 1.2Ueq(C) for CH group or 1.5Ueq(C) for CH3 group. H atoms of water molecule were tentatively located in difference Fourier maps and refined with distance restraints of O–H = 0.84 (1) and H···H = 1.35 (1) Å, and with Uiso(H) = 1.5Ueq(O). The highest residual electron density was 1.14 Å from atom I1 and the deepest hole 0.81 Å from atom I1.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing view of the title compound. Hydrogen bonds are depicted as dashed lines.
Bis(2,2'-bipyridine-κ2N,N')(4-methylbenzoato- κ2O,O')copper(II) iodide hemihydrate top
Crystal data top
[Cu(C8H7O2)(C10H8N2)2]I·0.5H2OZ = 4
Mr = 646.96F000 = 1288
Triclinic, P1Dx = 1.603 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 14.6698 (4) ÅCell parameters from 5300 reflections
b = 15.3588 (4) Åθ = 1.3–28.0º
c = 15.4224 (7) ŵ = 2.00 mm−1
α = 100.943 (2)ºT = 296 (2) K
β = 114.345 (2)ºBlock, blue
γ = 111.996 (2)º0.37 × 0.30 × 0.26 mm
V = 2680.64 (19) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		9564 independent reflections
Radiation source: fine-focus sealed tube6740 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 296(2) Kθmax = 25.2º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.525, Tmax = 0.624k = −18→18
29909 measured reflectionsl = −17→18
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.149  w = 1/[σ2(Fo2) + (0.0774P)2 + 2.4876P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
9564 reflectionsΔρmax = 1.56 e Å−3
660 parametersΔρmin = −1.53 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu(C8H7O2)(C10H8N2)2]I·0.5H2Oγ = 111.996 (2)º
Mr = 646.96V = 2680.64 (19) Å3
Triclinic, P1Z = 4
a = 14.6698 (4) ÅMo Kα
b = 15.3588 (4) ŵ = 2.00 mm−1
c = 15.4224 (7) ÅT = 296 (2) K
α = 100.943 (2)º0.37 × 0.30 × 0.26 mm
β = 114.345 (2)º
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		9564 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6740 reflections with I > 2σ(I)
Tmin = 0.525, Tmax = 0.624Rint = 0.037
29909 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0473 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.03Δρmax = 1.56 e Å−3
9564 reflectionsΔρmin = −1.53 e Å−3
660 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5583 (5)−0.0992 (4)0.8879 (4)0.0588 (14)
H10.6232−0.08840.88440.071*
C20.5284 (6)−0.1583 (5)0.9396 (5)0.0685 (16)
H20.5726−0.18620.97070.082*
C30.4332 (6)−0.1746 (5)0.9441 (5)0.0787 (19)
H30.4115−0.21370.97870.094*
C40.3693 (5)−0.1328 (5)0.8973 (5)0.0698 (17)
H40.3035−0.14390.89920.084*
C50.4036 (4)−0.0738 (4)0.8470 (4)0.0515 (12)
C60.3422 (4)−0.0237 (4)0.7958 (4)0.0543 (13)
C70.2355 (6)−0.0438 (5)0.7799 (6)0.083 (2)
H70.1976−0.09160.79980.099*
C80.1861 (6)0.0083 (7)0.7338 (7)0.100 (3)
H80.1139−0.00470.72210.121*
C90.2416 (7)0.0782 (7)0.7056 (6)0.091 (2)
H90.20950.11510.67670.110*
C100.3481 (5)0.0941 (5)0.7206 (5)0.0719 (17)
H100.38620.14080.69970.086*
C110.3340 (4)−0.0838 (4)0.5409 (4)0.0536 (13)
H110.2900−0.06450.56050.064*
C120.2824 (5)−0.1491 (4)0.4398 (4)0.0617 (15)
H120.2052−0.17260.39130.074*
C130.3469 (5)−0.1793 (4)0.4111 (4)0.0632 (15)
H130.3130−0.22500.34330.076*
C140.4609 (5)−0.1414 (4)0.4830 (4)0.0573 (13)
H140.5056−0.16000.46400.069*
C150.5095 (4)−0.0754 (3)0.5840 (4)0.0441 (11)
C160.6312 (4)−0.0306 (3)0.6684 (4)0.0443 (11)
C170.7116 (5)−0.0489 (4)0.6564 (5)0.0617 (14)
H170.6910−0.08990.59120.074*
C180.8221 (5)−0.0065 (5)0.7407 (5)0.0733 (17)
H180.8765−0.01890.73340.088*
C190.8507 (5)0.0547 (5)0.8365 (5)0.0703 (16)
H190.92420.08300.89500.084*
C200.7693 (4)0.0734 (4)0.8442 (4)0.0595 (14)
H200.78940.11630.90830.071*
C210.6656 (4)0.2547 (4)0.8568 (4)0.0494 (12)
C220.7626 (4)0.3594 (4)0.9370 (4)0.0472 (12)
C230.8244 (5)0.3793 (5)1.0407 (4)0.0666 (16)
H230.80660.32611.06230.080*
C240.9126 (5)0.4775 (5)1.1130 (5)0.0778 (18)
H240.95200.48911.18290.093*
C250.9441 (5)0.5588 (4)1.0854 (5)0.0642 (16)
C260.8836 (5)0.5382 (4)0.9817 (5)0.0664 (16)
H260.90370.59110.96000.080*
C270.7936 (5)0.4407 (4)0.9084 (4)0.0577 (13)
H270.75310.42970.83870.069*
C281.0395 (6)0.6647 (5)1.1648 (6)0.099 (2)
H28A1.00740.70231.18590.148*
H28B1.08010.69921.13530.148*
H28C1.09240.66051.22430.148*
C361.0037 (6)0.3445 (7)0.4202 (7)0.105 (3)
H36A0.99980.30900.35920.158*
H36B1.01050.30800.46440.158*
H36C1.07010.41270.45730.158*
C300.8952 (5)0.3506 (5)0.3882 (5)0.0709 (17)
C310.8731 (6)0.4128 (7)0.3403 (6)0.098 (3)
H310.92830.45400.32880.118*
C320.7725 (5)0.4176 (5)0.3080 (5)0.0744 (18)
H320.76070.46060.27510.089*
C330.6900 (4)0.3575 (4)0.3255 (4)0.0432 (11)
C340.7122 (4)0.2956 (4)0.3758 (4)0.0521 (12)
H340.65800.25510.38860.063*
C350.5819 (4)0.3622 (4)0.2935 (4)0.0461 (11)
C370.6852 (4)0.6225 (4)0.4203 (5)0.0648 (15)
H370.71210.60570.37830.078*
C380.7636 (5)0.6975 (4)0.5194 (5)0.0746 (18)
H380.84240.73180.54380.090*
C390.7249 (5)0.7213 (4)0.5815 (5)0.0669 (16)
H390.77750.76970.65010.080*
C400.6076 (5)0.6734 (4)0.5428 (4)0.0562 (13)
H400.57980.69010.58400.067*
C410.5320 (4)0.6000 (3)0.4412 (4)0.0441 (11)
C420.4036 (4)0.5452 (3)0.3899 (3)0.0417 (11)
C430.3480 (5)0.5727 (4)0.4316 (4)0.0569 (13)
H430.38980.62750.49600.068*
C440.2272 (5)0.5173 (5)0.3759 (5)0.0681 (16)
H440.18670.53580.40150.082*
C450.1691 (5)0.4352 (4)0.2830 (5)0.0627 (15)
H450.08860.39550.24570.075*
C460.2306 (4)0.4124 (4)0.2458 (4)0.0506 (12)
H460.19020.35670.18240.061*
C470.2668 (5)0.2356 (4)0.1058 (5)0.0598 (14)
H470.28490.22710.16780.072*
C480.1841 (5)0.1508 (4)0.0136 (6)0.0715 (17)
H480.14740.08610.01260.086*
C490.1574 (5)0.1646 (5)−0.0771 (6)0.082 (2)
H490.10130.1087−0.14080.098*
C500.2138 (5)0.2621 (5)−0.0742 (4)0.0706 (17)
H500.19660.2717−0.13560.085*
C510.2964 (4)0.3448 (4)0.0223 (4)0.0499 (12)
C520.3624 (4)0.4512 (4)0.0340 (4)0.0481 (12)
C290.8130 (5)0.2930 (4)0.4069 (5)0.0606 (14)
H290.82610.25140.44140.073*
C530.3479 (5)0.4781 (5)−0.0497 (4)0.0609 (14)
H530.29210.4294−0.11770.073*
C540.4170 (6)0.5774 (5)−0.0305 (5)0.0700 (17)
H540.40960.5968−0.08560.084*
C550.4974 (5)0.6486 (5)0.0704 (5)0.0643 (15)
H550.54490.71650.08470.077*
C560.5062 (5)0.6173 (4)0.1499 (4)0.0533 (13)
H560.56040.66550.21830.064*
Cu20.44994 (5)0.45165 (4)0.24535 (4)0.04330 (16)
Cu10.53604 (5)0.04754 (4)0.76873 (5)0.04622 (17)
I10.04839 (6)0.20792 (5)0.62512 (4)0.1112 (2)
I20.98058 (3)0.14574 (3)0.13668 (3)0.07583 (16)
N10.4398 (3)0.5204 (3)0.1327 (3)0.0449 (9)
N20.3228 (3)0.3298 (3)0.1110 (3)0.0483 (10)
N30.3964 (4)0.0430 (3)0.7649 (3)0.0544 (11)
N40.4981 (3)−0.0577 (3)0.8433 (3)0.0498 (10)
N50.4459 (3)−0.0467 (3)0.6130 (3)0.0440 (9)
N60.6613 (3)0.0313 (3)0.7616 (3)0.0479 (10)
N70.3464 (3)0.4665 (3)0.2964 (3)0.0416 (9)
N80.5707 (3)0.5723 (3)0.3818 (3)0.0478 (10)
O10.6478 (3)0.1823 (3)0.8889 (3)0.0568 (9)
O20.6079 (3)0.2405 (3)0.7651 (3)0.0674 (10)
O30.5675 (3)0.4192 (3)0.2437 (3)0.0522 (8)
O40.5122 (3)0.3137 (3)0.3162 (3)0.0597 (9)
O1W0.8745 (9)0.9386 (6)0.5468 (7)0.201 (4)
H2W0.90821.00130.56630.301*
H1W0.89000.91910.50420.301*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.063 (3)0.062 (3)0.066 (4)0.034 (3)0.041 (3)0.030 (3)
C20.075 (4)0.066 (4)0.066 (4)0.034 (3)0.039 (3)0.031 (3)
C30.093 (5)0.070 (4)0.078 (4)0.029 (4)0.062 (4)0.028 (3)
C40.069 (4)0.064 (4)0.067 (4)0.018 (3)0.050 (3)0.011 (3)
C50.049 (3)0.045 (3)0.048 (3)0.015 (2)0.031 (3)0.004 (2)
C60.042 (3)0.056 (3)0.049 (3)0.017 (2)0.027 (3)0.001 (2)
C70.058 (4)0.090 (5)0.097 (5)0.035 (4)0.049 (4)0.020 (4)
C80.060 (4)0.124 (7)0.101 (6)0.050 (5)0.041 (4)0.011 (5)
C90.079 (5)0.106 (6)0.091 (5)0.071 (5)0.034 (4)0.023 (4)
C100.067 (4)0.069 (4)0.076 (4)0.046 (3)0.032 (3)0.013 (3)
C110.049 (3)0.054 (3)0.048 (3)0.023 (2)0.022 (3)0.018 (2)
C120.051 (3)0.065 (4)0.045 (3)0.021 (3)0.016 (3)0.017 (3)
C130.068 (4)0.068 (4)0.043 (3)0.028 (3)0.029 (3)0.015 (3)
C140.065 (4)0.055 (3)0.056 (3)0.030 (3)0.037 (3)0.017 (3)
C150.047 (3)0.040 (2)0.050 (3)0.021 (2)0.029 (2)0.022 (2)
C160.048 (3)0.043 (3)0.053 (3)0.027 (2)0.032 (2)0.022 (2)
C170.059 (3)0.062 (3)0.070 (4)0.034 (3)0.038 (3)0.019 (3)
C180.059 (4)0.083 (4)0.087 (5)0.043 (3)0.042 (4)0.029 (4)
C190.042 (3)0.085 (4)0.070 (4)0.030 (3)0.025 (3)0.021 (3)
C200.041 (3)0.065 (3)0.055 (3)0.022 (3)0.022 (3)0.015 (3)
C210.044 (3)0.054 (3)0.048 (3)0.022 (2)0.031 (3)0.009 (2)
C220.039 (3)0.043 (3)0.049 (3)0.016 (2)0.023 (2)0.008 (2)
C230.060 (4)0.069 (4)0.052 (3)0.019 (3)0.027 (3)0.023 (3)
C240.056 (4)0.084 (5)0.047 (3)0.017 (3)0.014 (3)0.010 (3)
C250.041 (3)0.056 (3)0.067 (4)0.015 (3)0.026 (3)0.000 (3)
C260.054 (3)0.049 (3)0.083 (5)0.021 (3)0.034 (3)0.019 (3)
C270.055 (3)0.054 (3)0.056 (3)0.027 (3)0.026 (3)0.016 (3)
C280.057 (4)0.075 (4)0.098 (5)0.013 (3)0.026 (4)−0.008 (4)
C360.064 (4)0.188 (8)0.124 (6)0.083 (5)0.063 (5)0.107 (7)
C300.055 (3)0.109 (5)0.072 (4)0.048 (3)0.039 (3)0.053 (4)
C310.059 (4)0.168 (7)0.121 (6)0.064 (5)0.062 (4)0.109 (6)
C320.057 (4)0.097 (5)0.088 (5)0.041 (3)0.041 (3)0.061 (4)
C330.038 (3)0.052 (3)0.039 (3)0.022 (2)0.021 (2)0.016 (2)
C340.050 (3)0.056 (3)0.060 (3)0.027 (2)0.037 (3)0.025 (3)
C350.042 (3)0.055 (3)0.031 (2)0.025 (2)0.015 (2)0.006 (2)
C370.041 (3)0.061 (3)0.071 (4)0.022 (3)0.025 (3)0.007 (3)
C380.036 (3)0.057 (3)0.088 (5)0.020 (3)0.015 (3)0.000 (3)
C390.051 (3)0.053 (3)0.058 (3)0.023 (3)0.009 (3)0.003 (3)
C400.053 (3)0.055 (3)0.044 (3)0.024 (3)0.019 (3)0.010 (2)
C410.042 (3)0.039 (2)0.039 (3)0.017 (2)0.015 (2)0.015 (2)
C420.042 (3)0.039 (2)0.039 (3)0.018 (2)0.020 (2)0.017 (2)
C430.056 (3)0.053 (3)0.054 (3)0.021 (3)0.033 (3)0.014 (2)
C440.070 (4)0.066 (4)0.080 (4)0.032 (3)0.054 (4)0.023 (3)
C450.048 (3)0.060 (3)0.075 (4)0.021 (3)0.038 (3)0.018 (3)
C460.042 (3)0.045 (3)0.053 (3)0.015 (2)0.023 (2)0.014 (2)
C470.051 (3)0.051 (3)0.067 (4)0.026 (3)0.029 (3)0.013 (3)
C480.051 (3)0.050 (3)0.084 (5)0.015 (3)0.032 (3)0.005 (3)
C490.044 (3)0.067 (4)0.077 (5)0.011 (3)0.020 (3)−0.015 (3)
C500.049 (3)0.087 (5)0.045 (3)0.026 (3)0.019 (3)0.003 (3)
C510.040 (3)0.061 (3)0.041 (3)0.027 (2)0.020 (2)0.007 (2)
C520.044 (3)0.064 (3)0.043 (3)0.035 (2)0.025 (2)0.016 (2)
C290.062 (3)0.076 (4)0.070 (4)0.045 (3)0.041 (3)0.043 (3)
C530.067 (4)0.084 (4)0.044 (3)0.049 (3)0.029 (3)0.026 (3)
C540.092 (5)0.094 (5)0.062 (4)0.066 (4)0.048 (4)0.046 (4)
C550.081 (4)0.067 (4)0.075 (4)0.046 (3)0.052 (4)0.041 (3)
C560.062 (3)0.053 (3)0.053 (3)0.034 (3)0.032 (3)0.025 (3)
Cu20.0401 (3)0.0434 (3)0.0389 (3)0.0195 (3)0.0192 (3)0.0103 (2)
Cu10.0409 (3)0.0460 (3)0.0491 (4)0.0218 (3)0.0244 (3)0.0136 (3)
I10.1320 (5)0.1664 (6)0.0966 (4)0.1121 (5)0.0670 (4)0.0762 (4)
I20.0619 (3)0.0608 (3)0.0672 (3)0.01033 (19)0.0296 (2)0.0105 (2)
N10.045 (2)0.053 (2)0.040 (2)0.029 (2)0.0223 (19)0.0163 (18)
N20.042 (2)0.043 (2)0.046 (2)0.0190 (18)0.0195 (19)0.0059 (18)
N30.046 (2)0.055 (3)0.054 (3)0.028 (2)0.024 (2)0.009 (2)
N40.046 (2)0.051 (2)0.051 (2)0.021 (2)0.031 (2)0.015 (2)
N50.044 (2)0.039 (2)0.045 (2)0.0182 (18)0.023 (2)0.0153 (17)
N60.042 (2)0.046 (2)0.053 (3)0.0201 (19)0.027 (2)0.017 (2)
N70.040 (2)0.043 (2)0.039 (2)0.0192 (18)0.0207 (18)0.0167 (17)
N80.040 (2)0.049 (2)0.049 (2)0.0215 (19)0.023 (2)0.0126 (19)
O10.058 (2)0.046 (2)0.059 (2)0.0213 (17)0.0337 (19)0.0136 (17)
O20.068 (2)0.065 (2)0.048 (2)0.022 (2)0.029 (2)0.0106 (18)
O30.053 (2)0.060 (2)0.051 (2)0.0343 (17)0.0282 (17)0.0239 (17)
O40.048 (2)0.084 (3)0.058 (2)0.0359 (19)0.0337 (19)0.031 (2)
O1W0.325 (12)0.176 (7)0.233 (9)0.142 (8)0.225 (10)0.116 (7)
Geometric parameters (Å, °) top
C1—N41.322 (6)C31—H310.9300
C1—C21.384 (8)C32—C331.385 (7)
C1—H10.9300C32—H320.9300
C2—C31.357 (9)C33—C341.384 (7)
C2—H20.9300C33—C351.489 (6)
C3—C41.372 (9)C34—C291.372 (7)
C3—H30.9300C34—H340.9300
C4—C51.387 (8)C35—O41.243 (6)
C4—H40.9300C35—O31.289 (6)
C5—N41.341 (6)C37—N81.342 (6)
C5—C61.480 (8)C37—C381.370 (8)
C6—N31.340 (7)C37—H370.9300
C6—C71.377 (8)C38—C391.358 (9)
C7—C81.377 (11)C38—H380.9300
C7—H70.9300C39—C401.377 (8)
C8—C91.348 (11)C39—H390.9300
C8—H80.9300C40—C411.384 (7)
C9—C101.395 (9)C40—H400.9300
C9—H90.9300C41—N81.344 (6)
C10—N31.344 (7)C41—C421.487 (6)
C10—H100.9300C42—N71.351 (6)
C11—N51.346 (6)C42—C431.358 (7)
C11—C121.369 (7)C43—C441.393 (8)
C11—H110.9300C43—H430.9300
C12—C131.380 (8)C44—C451.368 (8)
C12—H120.9300C44—H440.9300
C13—C141.364 (8)C45—C461.360 (7)
C13—H130.9300C45—H450.9300
C14—C151.380 (7)C46—N71.338 (6)
C14—H140.9300C46—H460.9300
C15—N51.357 (6)C47—N21.336 (7)
C15—C161.476 (7)C47—C481.371 (8)
C16—N61.345 (6)C47—H470.9300
C16—C171.384 (7)C48—C491.370 (10)
C17—C181.375 (8)C48—H480.9300
C17—H170.9300C49—C501.394 (9)
C18—C191.382 (9)C49—H490.9300
C18—H180.9300C50—C511.393 (7)
C19—C201.372 (8)C50—H500.9300
C19—H190.9300C51—N21.349 (6)
C20—N61.344 (6)C51—C521.484 (7)
C20—H200.9300C52—N11.339 (6)
C21—O21.233 (6)C52—C531.387 (7)
C21—O11.284 (6)C29—H290.9300
C21—C221.490 (7)C53—C541.366 (8)
C22—C231.373 (7)C53—H530.9300
C22—C271.381 (7)C54—C551.372 (8)
C23—C241.380 (8)C54—H540.9300
C23—H230.9300C55—C561.375 (7)
C24—C251.373 (9)C55—H550.9300
C24—H240.9300C56—N11.336 (6)
C25—C261.369 (8)C56—H560.9300
C25—C281.492 (8)Cu1—O11.976 (4)
C26—C271.381 (8)Cu1—O22.769 (4)
C26—H260.9300Cu1—N61.987 (4)
C27—H270.9300Cu1—N32.000 (4)
C28—H28A0.9600Cu1—N52.060 (4)
C28—H28B0.9600Cu1—N42.192 (4)
C28—H28C0.9600Cu2—O31.974 (3)
C36—C301.506 (8)Cu2—O42.832 (3)
C36—H36A0.9600Cu2—N81.997 (4)
C36—H36B0.9600Cu2—N22.001 (4)
C36—H36C0.9600Cu2—N72.038 (4)
C30—C311.367 (8)Cu2—N12.181 (4)
C30—C291.379 (8)O1W—H2W0.8200
C31—C321.385 (8)O1W—H1W0.8200
N4—C1—C2122.5 (5)C37—C38—H38120.4
N4—C1—H1118.7C38—C39—C40119.8 (5)
C2—C1—H1118.7C38—C39—H39120.1
C3—C2—C1118.7 (6)C40—C39—H39120.1
C3—C2—H2120.6C39—C40—C41118.5 (5)
C1—C2—H2120.6C39—C40—H40120.7
C2—C3—C4119.3 (6)C41—C40—H40120.7
C2—C3—H3120.3N8—C41—C40121.6 (5)
C4—C3—H3120.3N8—C41—C42115.0 (4)
C3—C4—C5119.5 (6)C40—C41—C42123.5 (5)
C3—C4—H4120.2N7—C42—C43122.7 (4)
C5—C4—H4120.2N7—C42—C41113.9 (4)
N4—C5—C4120.7 (5)C43—C42—C41123.4 (4)
N4—C5—C6115.5 (4)C42—C43—C44118.7 (5)
C4—C5—C6123.8 (5)C42—C43—H43120.7
N3—C6—C7121.3 (6)C44—C43—H43120.7
N3—C6—C5116.0 (4)C45—C44—C43118.8 (5)
C7—C6—C5122.8 (6)C45—C44—H44120.6
C6—C7—C8118.7 (7)C43—C44—H44120.6
C6—C7—H7120.7C46—C45—C44119.2 (5)
C8—C7—H7120.7C46—C45—H45120.4
C9—C8—C7120.6 (7)C44—C45—H45120.4
C9—C8—H8119.7N7—C46—C45123.0 (5)
C7—C8—H8119.7N7—C46—H46118.5
C8—C9—C10118.8 (7)C45—C46—H46118.5
C8—C9—H9120.6N2—C47—C48123.2 (6)
C10—C9—H9120.6N2—C47—H47118.4
N3—C10—C9120.8 (7)C48—C47—H47118.4
N3—C10—H10119.6C49—C48—C47117.8 (6)
C9—C10—H10119.6C49—C48—H48121.1
N5—C11—C12122.4 (5)C47—C48—H48121.1
N5—C11—H11118.8C48—C49—C50120.3 (6)
C12—C11—H11118.8C48—C49—H49119.8
C11—C12—C13118.8 (5)C50—C49—H49119.8
C11—C12—H12120.6C51—C50—C49118.7 (6)
C13—C12—H12120.6C51—C50—H50120.6
C14—C13—C12119.5 (5)C49—C50—H50120.6
C14—C13—H13120.3N2—C51—C50120.2 (5)
C12—C13—H13120.3N2—C51—C52116.7 (4)
C13—C14—C15119.7 (5)C50—C51—C52123.0 (5)
C13—C14—H14120.1N1—C52—C53121.9 (5)
C15—C14—H14120.1N1—C52—C51114.6 (4)
N5—C15—C14121.0 (5)C53—C52—C51123.5 (5)
N5—C15—C16114.4 (4)C34—C29—C30121.6 (5)
C14—C15—C16124.6 (5)C34—C29—H29119.2
N6—C16—C17120.4 (5)C30—C29—H29119.2
N6—C16—C15115.3 (4)C54—C53—C52118.8 (5)
C17—C16—C15124.3 (5)C54—C53—H53120.6
C18—C17—C16120.1 (6)C52—C53—H53120.6
C18—C17—H17119.9C53—C54—C55119.7 (5)
C16—C17—H17119.9C53—C54—H54120.1
C17—C18—C19118.7 (6)C55—C54—H54120.1
C17—C18—H18120.7C54—C55—C56118.6 (6)
C19—C18—H18120.7C54—C55—H55120.7
C20—C19—C18119.3 (6)C56—C55—H55120.7
C20—C19—H19120.4N1—C56—C55122.6 (5)
C18—C19—H19120.4N1—C56—H56118.7
N6—C20—C19121.7 (5)C55—C56—H56118.7
N6—C20—H20119.1O1—Cu1—O252.46 (16)
C19—C20—H20119.1O1—Cu1—N692.58 (16)
O2—C21—O1123.2 (5)O1—Cu1—N394.78 (16)
O2—C21—C22120.5 (5)O2—Cu1—N696.13 (16)
O1—C21—C22116.3 (5)O2—Cu1—N390.52 (16)
C23—C22—C27117.5 (5)N6—Cu1—N3172.15 (16)
C23—C22—C21122.2 (5)O1—Cu1—N5152.67 (15)
C27—C22—C21120.3 (5)O2—Cu1—N5101.75 (16)
C22—C23—C24120.7 (6)N6—Cu1—N580.38 (16)
C22—C23—H23119.7N3—Cu1—N594.23 (16)
C24—C23—H23119.7O1—Cu1—N4102.51 (15)
C25—C24—C23122.3 (6)O2—Cu1—N4152.05 (16)
C25—C24—H24118.9N6—Cu1—N497.40 (16)
C23—C24—H24118.9N3—Cu1—N478.34 (17)
C26—C25—C24116.8 (5)N5—Cu1—N4104.56 (15)
C26—C25—C28121.7 (6)O3—Cu2—O451.67 (15)
C24—C25—C28121.6 (6)O3—Cu2—N890.84 (15)
C25—C26—C27121.7 (6)O3—Cu2—N291.78 (15)
C25—C26—H26119.1O4—Cu2—N893.70 (15)
C27—C26—H26119.1O4—Cu2—N286.63 (15)
C26—C27—C22121.0 (5)N8—Cu2—N2176.92 (16)
C26—C27—H27119.5O3—Cu2—N7156.24 (15)
C22—C27—H27119.5O4—Cu2—N7106.46 (15)
C25—C28—H28A109.5N8—Cu2—N780.59 (16)
C25—C28—H28B109.5N2—Cu2—N796.37 (16)
H28A—C28—H28B109.5O3—Cu2—N194.97 (14)
C25—C28—H28C109.5O4—Cu2—N1143.21 (15)
H28A—C28—H28C109.5N8—Cu2—N1102.89 (16)
H28B—C28—H28C109.5N2—Cu2—N178.49 (16)
C30—C36—H36A109.5N7—Cu2—N1108.50 (14)
C30—C36—H36B109.5C56—N1—C52118.4 (4)
H36A—C36—H36B109.5C56—N1—Cu2128.6 (3)
C30—C36—H36C109.5C52—N1—Cu2112.8 (3)
H36A—C36—H36C109.5C47—N2—C51119.7 (4)
H36B—C36—H36C109.5C47—N2—Cu2123.0 (4)
C31—C30—C29116.7 (5)C51—N2—Cu2117.3 (3)
C31—C30—C36122.4 (6)C6—N3—C10119.8 (5)
C29—C30—C36120.9 (6)C6—N3—Cu1117.7 (3)
C30—C31—C32123.3 (6)C10—N3—Cu1122.0 (4)
C30—C31—H31118.4C1—N4—C5119.2 (5)
C32—C31—H31118.4C1—N4—Cu1129.0 (3)
C33—C32—C31119.1 (5)C5—N4—Cu1111.7 (3)
C33—C32—H32120.5C11—N5—C15118.6 (4)
C31—C32—H32120.5C11—N5—Cu1127.7 (3)
C34—C33—C32118.3 (5)C15—N5—Cu1113.7 (3)
C34—C33—C35121.2 (4)C20—N6—C16119.8 (4)
C32—C33—C35120.5 (5)C20—N6—Cu1124.0 (4)
C29—C34—C33121.1 (5)C16—N6—Cu1116.1 (3)
C29—C34—H34119.5C46—N7—C42117.5 (4)
C33—C34—H34119.5C46—N7—Cu2127.8 (3)
O4—C35—O3123.7 (4)C42—N7—Cu2114.5 (3)
O4—C35—C33120.0 (4)C37—N8—C41118.6 (4)
O3—C35—C33116.3 (4)C37—N8—Cu2125.8 (4)
N8—C37—C38122.2 (6)C41—N8—Cu2115.5 (3)
N8—C37—H37118.9C21—O1—Cu1110.0 (3)
C38—C37—H37118.9C35—O3—Cu2111.0 (3)
C39—C38—C37119.2 (5)H2W—O1W—H1W103.5
C39—C38—H38120.4
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···I1i0.823.153.935 (8)161
O1W—H2W···I1ii0.822.763.568 (8)170
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z.
Table 1
Selected geometric parameters (Å) top
Cu1—O11.976 (4)Cu2—O31.974 (3)
Cu1—O22.769 (4)Cu2—O42.832 (3)
Cu1—N61.987 (4)Cu2—N81.997 (4)
Cu1—N32.000 (4)Cu2—N22.001 (4)
Cu1—N52.060 (4)Cu2—N72.038 (4)
Cu1—N42.192 (4)Cu2—N12.181 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···I1i0.823.153.935 (8)161
O1W—H2W···I1ii0.822.763.568 (8)170
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z.
Acknowledgements top

The authors acknowledge South China University of Technology for supporting this work.

references
References top

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

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