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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1111–m1112.
Published online 2008 August 6. doi:  10.1107/S1600536808024252
PMCID: PMC2960663

Bis(2,2′-bipyridine-κ2 N,N′)(4-methyl­benzoato-κ2 O,O′)copper(II) iodide hemihydrate

Abstract

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 π–π 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].

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-m1111-scheme1.jpg

Experimental

Crystal data

  • [Cu(C8H7O2)(C10H8N2)2]I·0.5H2O
  • M r = 646.96
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1111-efi1.jpg
  • a = 14.6698 (4) Å
  • b = 15.3588 (4) Å
  • c = 15.4224 (7) Å
  • α = 100.943 (2)°
  • β = 114.345 (2)°
  • γ = 111.996 (2)°
  • V = 2680.64 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.00 mm−1
  • T = 296 (2) K
  • 0.37 × 0.30 × 0.26 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.525, T max = 0.624
  • 29909 measured reflections
  • 9564 independent reflections
  • 6740 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.149
  • S = 1.03
  • 9564 reflections
  • 660 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 1.55 e Å−3
  • Δρmin = −1.53 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024252/hy2148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024252/hy2148Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.
Fig. 2.
A packing view of the title compound. Hydrogen bonds are depicted as dashed lines.

Crystal data

[Cu(C8H7O2)(C10H8N2)2]I·0.5H2OZ = 4
Mr = 646.96F000 = 1288
Triclinic, P1Dx = 1.603 Mg m3
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 mm1
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

Bruker SMART APEXII CCD area-detector diffractometer9564 independent reflections
Radiation source: fine-focus sealed tube6740 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 296(2) Kθmax = 25.2º
[var phi] 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

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 Å3
660 parametersΔρmin = −1.53 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2148).

References

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  • Mao, Z.-W., Heinemann, F. W., Liehr, G. & van Eldik, R. (2001). J. Chem. Soc. Dalton Trans. pp. 3652–3662.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, W.-D., Gu, C.-S., Hao, X.-M. & Yan, J.-B. (2008a). Acta Cryst. E64, m522. [PMC free article] [PubMed]
  • Song, W.-D., Wang, H. & Ji, L.-L. (2008b). Acta Cryst. E64, m548. [PMC free article] [PubMed]
  • Song, W.-D., Wang, H. & Miao, Y.-L. (2008c). Acta Cryst. E64, m716. [PMC free article] [PubMed]
  • Song, W.-D., Yan, J.-B. & Hao, X.-M. (2008d). Acta Cryst. E64, m919–m920. [PMC free article] [PubMed]

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