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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m169.
Published online 2007 December 12. doi:  10.1107/S1600536807065713
PMCID: PMC2915105

Poly[[di-μ4-4,4′-oxydiphthalato-tetrakis[μ2-1,1′-(p-phenyl­enedimethyl­ene)di-1H-imidazole]tetra­copper(II)] monohydrate]

Abstract

In the title compound, {[Cu4(C16H6O9)2(C14H14N4)4]·H2O}n, the water mol­ecule is disordered over two positions; site-occupancy factors were fixed at 0.25. The CuII atom exhibits a square-planar coordination geometry with two O atoms of the two 4,4′-oxydiphthalate ligands and two N atoms of the two 1,4-bis­(imidazol-1-ylmeth­yl)benzene groups. A three-dimensional honeycomb framework structure is formed. Aromatic π–π stacking inter­actions are observed, with a centroid–centroid distance of 3.373 (5) Å.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m169-scheme1.jpg

Experimental

Crystal data

  • [Cu4(C16H6O9)2(C14H14N4)4]·H2O
  • M r = 1909.76
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m169-efi1.jpg
  • a = 18.750 (3) Å
  • b = 10.3283 (17) Å
  • c = 22.386 (4) Å
  • β = 97.388 (3)°
  • V = 4299.1 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.06 mm−1
  • T = 294 (2) K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 18013 measured reflections
  • 7404 independent reflections
  • 4497 reflections with I > 2σ(I)
  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.169
  • S = 1.02
  • 7404 reflections
  • 586 parameters
  • H-atom parameters constrained
  • Δρmax = 0.75 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2005 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065713/hk2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065713/hk2401Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Henan Administration of Science and Technology (grant No. 0111030700).

supplementary crystallographic information

Comment

As part of our ongoing studies, we synthesized the title compound, (I), and report herein its crystal structure.

In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). When the crystal structure was solved, the water molecule was found to be disordered.

The CuII atom exhibits a square-planar coordination geometry with two O atoms of the two 4,4'-oxydiphthalic acid (H4ODPA) and two N atoms of the two 1,4-bis(imidazol-1-yl-methyl)benzene (BIX) groups, respectively. Four carboxylic O atoms of H4ODPA coordinate four different Cu ion and a three-dimensional honeycomb framework built from Cu ion and H4ODPA (Figs. 2 and 3) joined by BIX groups (Fig. 4).

The π-π stacking interactions between aromatic rings of Cg1 and Cg2 [Cg1 and Cg2 are (N7,N8,C16—C18) and (N3i,N4i,C31i—C33i) ring centroids, respectively, symmetry code: (i) 2 - x, 1 - y, 1 - z] are observed, with a centroid-centroid distance of 3.373 (5) Å.

Experimental

The compound, (I), was synthesized hydrothermally in a Teflon-lined autoclave (23 ml) by heating a mixture of H4ODPA (0.1 mmol), BIX (0.1 mmol), Cu(NO3)2.4H2O (0.2 mmol) and one drop of Et3N (pH ~ 8–9) in water (10 ml) at 393 K for 3 d. Blue single crystals were collected in 55% yield based on Cu(NO3)2.4H2O.

Refinement

When the crystal structure was solved, the water molecule was found to be disordered. During refinement, the occupancies of disordered O and H atoms were kept fixed as 0.25. H atoms were positioned geometrically, with O—H = 0.85 Å (for H2O) and C—H = 0.93 and 0.97 Å for aromatic and methylene H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,O).

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.
Fig. 2.
The three-dimensional framework built from Cu ion and H4ODPA.
Fig. 3.
The three-dimensional framework built from Cu ion and H4ODPA, viewed along the a axis.
Fig. 4.
The crystal structure of (I), viewed along the b axis.

Crystal data

[Cu4(C16H6O9)2(C14H14N4)4]·H2OF000 = 1956
Mr = 1909.76Dx = 1.475 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2326 reflections
a = 18.750 (3) Åθ = 4.8–40.6º
b = 10.3283 (17) ŵ = 1.06 mm1
c = 22.386 (4) ÅT = 294 (2) K
β = 97.388 (3)ºBlock, blue
V = 4299.1 (13) Å30.22 × 0.18 × 0.16 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer4497 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.068
Monochromator: graphiteθmax = 25.0º
T = 294(2) Kθmin = 2.2º
[var phi] and ω scansh = −21→22
Absorption correction: nonek = −12→11
18013 measured reflectionsl = −26→21
7404 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.169  w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
7404 reflectionsΔρmax = 0.75 e Å3
586 parametersΔρmin = −0.45 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/UeqOcc. (<1)
Cu10.89629 (4)0.53392 (7)0.32168 (3)0.0318 (2)
Cu20.76895 (4)0.45820 (7)0.61410 (3)0.0365 (2)
O10.2712 (2)0.0667 (5)0.2379 (2)0.0592 (14)
O20.3459 (2)0.1096 (4)0.17161 (17)0.0389 (10)
O30.4802 (2)−0.0241 (4)0.25179 (18)0.0470 (11)
O40.53069 (19)0.1398 (3)0.20835 (17)0.0356 (10)
O50.4896 (2)0.4422 (4)0.39105 (18)0.0486 (12)
O60.81238 (19)0.4642 (4)0.35422 (17)0.0369 (10)
O70.8091 (2)0.6633 (4)0.3895 (2)0.0621 (14)
O80.7925 (2)0.4500 (5)0.49595 (19)0.0681 (16)
O90.7022 (2)0.5057 (4)0.54384 (17)0.0391 (10)
N10.6103 (4)0.1859 (7)0.6206 (3)0.087 (2)
N20.7097 (4)0.2996 (6)0.6185 (3)0.0688 (19)
N30.8023 (2)0.6380 (4)0.6258 (2)0.0314 (11)
N40.8525 (3)0.8122 (5)0.6697 (2)0.0401 (13)
N51.2382 (3)0.9385 (5)0.6755 (2)0.0461 (14)
N61.3302 (3)0.9248 (5)0.7477 (2)0.0404 (13)
N70.9593 (2)0.4597 (4)0.3892 (2)0.0292 (11)
N80.9949 (3)0.3544 (4)0.4721 (2)0.0340 (12)
C10.3260 (3)0.1165 (6)0.2242 (3)0.0349 (14)
C20.3741 (3)0.1944 (5)0.2689 (2)0.0293 (13)
C30.3417 (3)0.2817 (6)0.3037 (3)0.0464 (17)
H30.29170.28530.29970.056*
C40.3806 (3)0.3634 (6)0.3439 (3)0.0465 (18)
H40.35750.42090.36700.056*
C50.4546 (3)0.3585 (6)0.3493 (3)0.0358 (15)
C60.4879 (3)0.2719 (6)0.3161 (2)0.0326 (14)
H60.53780.26790.32070.039*
C70.4484 (3)0.1900 (5)0.2756 (2)0.0280 (13)
C80.4889 (3)0.0921 (6)0.2425 (2)0.0308 (14)
C90.5605 (3)0.4739 (6)0.3875 (3)0.0356 (14)
C100.6079 (3)0.4676 (6)0.4391 (2)0.0344 (14)
H100.59130.44420.47500.041*
C110.6802 (3)0.4953 (5)0.4390 (2)0.0305 (14)
C120.7040 (3)0.5312 (5)0.3850 (2)0.0310 (13)
C130.6548 (3)0.5428 (6)0.3346 (3)0.0430 (16)
H130.67040.57070.29900.052*
C140.5830 (3)0.5145 (6)0.3348 (3)0.0435 (16)
H140.55050.52290.29990.052*
C150.7821 (3)0.5590 (6)0.3789 (3)0.0369 (15)
C160.9387 (3)0.3942 (5)0.4348 (2)0.0312 (14)
H160.89110.37840.44000.037*
C171.0338 (3)0.4608 (5)0.3990 (3)0.0347 (14)
H171.06370.50010.37430.042*
C181.0554 (3)0.3968 (6)0.4493 (3)0.0407 (15)
H181.10280.38300.46610.049*
C190.9927 (4)0.2740 (6)0.5262 (3)0.0477 (17)
H19A0.94860.29170.54310.057*
H19B1.03280.29700.55620.057*
C200.9965 (4)0.1321 (6)0.5124 (3)0.0426 (16)
C211.0591 (4)0.0760 (7)0.4987 (3)0.0533 (19)
H211.09970.12700.49730.064*
C220.9378 (4)0.0547 (6)0.5130 (3)0.0498 (18)
H220.89480.09070.52150.060*
C230.7299 (3)0.4818 (6)0.4961 (3)0.0380 (15)
C240.4858 (6)0.1297 (12)0.5001 (5)0.124 (4)
H240.47660.21820.49920.149*
C250.5183 (5)0.0706 (10)0.5526 (4)0.094 (3)
C260.5323 (6)−0.0552 (11)0.5505 (5)0.121 (4)
H260.5556−0.09480.58490.145*
C270.5349 (5)0.1519 (10)0.6110 (4)0.107 (3)
H27A0.50600.23010.60770.128*
H27B0.52270.10250.64510.128*
C280.6384 (5)0.2971 (8)0.6047 (3)0.069 (2)
H280.61150.36490.58610.082*
C290.6657 (6)0.1172 (11)0.6487 (5)0.104 (3)
H290.66320.03610.66640.125*
C300.7242 (6)0.1869 (9)0.6463 (4)0.096 (3)
H300.77020.16050.66210.115*
C310.8442 (3)0.6847 (6)0.6730 (3)0.0341 (14)
H310.86540.63420.70480.041*
C320.7838 (3)0.7438 (6)0.5905 (3)0.0455 (17)
H320.75410.74230.55380.055*
C330.8146 (4)0.8496 (7)0.6164 (3)0.0502 (18)
H330.81090.93340.60110.060*
C340.8975 (3)0.8937 (7)0.7129 (3)0.0510 (18)
H34A0.90390.85100.75180.061*
H34B0.87290.97510.71740.061*
C350.9698 (3)0.9209 (6)0.6940 (3)0.0388 (15)
C361.0180 (3)0.8213 (6)0.6928 (3)0.0466 (17)
H361.00550.73850.70410.056*
C371.0846 (4)0.8426 (6)0.6749 (3)0.0508 (18)
H371.11610.77370.67290.061*
C381.1049 (3)0.9674 (7)0.6599 (3)0.0428 (16)
C391.0563 (4)1.0655 (6)0.6628 (3)0.0463 (17)
H391.06881.14960.65330.056*
C400.9896 (4)1.0418 (6)0.6793 (3)0.0443 (16)
H400.95741.10990.68050.053*
C411.1763 (4)0.9926 (7)0.6379 (3)0.0539 (19)
H41A1.17480.95710.59760.065*
H41B1.18301.08540.63510.065*
C421.2778 (3)0.9996 (6)0.7212 (3)0.0423 (17)
H421.26951.08410.73290.051*
C431.2665 (4)0.8178 (7)0.6734 (3)0.056 (2)
H431.25000.75270.64640.067*
C441.3231 (3)0.8088 (7)0.7177 (3)0.0507 (18)
H441.35210.73630.72630.061*
O1W0.7029 (11)0.8502 (19)0.4349 (8)0.078 (6)0.25
H1WA0.66790.84010.40720.094*0.25
H1WB0.69810.92390.45080.094*0.25
O2W0.2753 (15)0.958 (3)0.5136 (11)0.132 (10)0.25
H2WA0.25090.88980.50570.158*0.25
H2WB0.31300.93780.53700.158*0.25

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0238 (4)0.0364 (4)0.0365 (4)−0.0029 (3)0.0080 (3)0.0031 (3)
Cu20.0295 (4)0.0462 (5)0.0309 (4)0.0004 (4)−0.0069 (3)0.0008 (4)
O10.036 (3)0.081 (4)0.061 (3)−0.020 (3)0.012 (2)−0.026 (3)
O20.027 (2)0.057 (3)0.030 (2)−0.004 (2)−0.0077 (19)−0.006 (2)
O30.050 (3)0.043 (3)0.049 (3)0.002 (2)0.010 (2)−0.002 (2)
O40.026 (2)0.037 (2)0.048 (3)0.0025 (18)0.020 (2)−0.0085 (19)
O50.018 (2)0.084 (3)0.043 (3)−0.006 (2)0.001 (2)−0.032 (2)
O60.022 (2)0.045 (3)0.045 (2)−0.008 (2)0.0082 (19)0.005 (2)
O70.042 (3)0.051 (3)0.096 (4)−0.021 (2)0.017 (3)−0.021 (3)
O80.021 (3)0.142 (5)0.038 (3)0.015 (3)−0.005 (2)−0.008 (3)
O90.030 (2)0.061 (3)0.025 (2)−0.004 (2)−0.0029 (19)0.0044 (19)
N10.086 (6)0.090 (5)0.077 (5)−0.041 (5)−0.023 (4)0.017 (4)
N20.079 (5)0.043 (4)0.072 (4)−0.005 (3)−0.035 (4)0.012 (3)
N30.020 (3)0.040 (3)0.034 (3)0.001 (2)0.001 (2)0.000 (2)
N40.030 (3)0.046 (4)0.042 (3)0.007 (2)−0.002 (3)−0.004 (3)
N50.038 (3)0.053 (4)0.047 (3)−0.011 (3)0.003 (3)−0.007 (3)
N60.028 (3)0.052 (4)0.042 (3)−0.002 (3)0.007 (3)−0.010 (3)
N70.023 (3)0.029 (3)0.035 (3)0.003 (2)0.002 (2)0.005 (2)
N80.039 (3)0.028 (3)0.034 (3)0.000 (2)0.002 (3)−0.001 (2)
C10.019 (3)0.041 (4)0.042 (4)0.007 (3)−0.006 (3)−0.005 (3)
C20.023 (3)0.038 (3)0.027 (3)−0.002 (3)0.001 (3)−0.004 (3)
C30.015 (3)0.070 (5)0.054 (4)−0.003 (3)0.002 (3)−0.021 (4)
C40.024 (4)0.064 (5)0.051 (4)0.002 (3)0.005 (3)−0.029 (4)
C50.022 (3)0.055 (4)0.030 (3)−0.002 (3)0.001 (3)−0.012 (3)
C60.018 (3)0.050 (4)0.030 (3)0.001 (3)0.003 (3)−0.005 (3)
C70.024 (3)0.037 (3)0.024 (3)0.005 (3)0.006 (3)0.000 (3)
C80.020 (3)0.039 (4)0.030 (3)0.001 (3)−0.010 (3)−0.007 (3)
C90.021 (3)0.049 (4)0.035 (4)0.003 (3)−0.001 (3)−0.015 (3)
C100.026 (3)0.054 (4)0.024 (3)−0.005 (3)0.007 (3)−0.007 (3)
C110.024 (3)0.040 (4)0.026 (3)−0.002 (3)−0.002 (3)−0.007 (3)
C120.023 (3)0.038 (3)0.032 (3)−0.001 (3)0.002 (3)−0.003 (3)
C130.032 (4)0.069 (5)0.029 (3)−0.004 (3)0.006 (3)0.002 (3)
C140.035 (4)0.063 (5)0.028 (3)0.000 (3)−0.012 (3)−0.003 (3)
C150.028 (4)0.049 (4)0.032 (3)−0.003 (3)0.001 (3)0.006 (3)
C160.029 (3)0.032 (3)0.035 (3)−0.002 (3)0.009 (3)−0.007 (3)
C170.031 (4)0.033 (3)0.040 (4)0.000 (3)0.007 (3)0.000 (3)
C180.028 (4)0.035 (4)0.058 (4)0.005 (3)0.002 (3)−0.003 (3)
C190.069 (5)0.038 (4)0.035 (4)−0.004 (3)0.003 (3)0.000 (3)
C200.059 (5)0.038 (4)0.028 (3)0.003 (4)−0.004 (3)0.004 (3)
C210.047 (5)0.048 (5)0.064 (5)−0.010 (3)0.003 (4)0.002 (4)
C220.048 (4)0.043 (4)0.059 (4)0.008 (4)0.011 (4)−0.003 (3)
C230.027 (4)0.054 (4)0.033 (4)−0.008 (3)0.003 (3)0.001 (3)
C240.128 (4)0.122 (4)0.123 (4)−0.004 (2)0.015 (2)0.002 (2)
C250.095 (3)0.093 (3)0.092 (3)−0.005 (2)0.007 (2)0.000 (2)
C260.123 (4)0.120 (4)0.118 (4)−0.001 (2)0.012 (2)0.001 (2)
C270.108 (4)0.107 (4)0.106 (4)−0.006 (2)0.014 (2)0.002 (2)
C280.074 (6)0.061 (5)0.067 (5)−0.024 (5)−0.009 (5)0.011 (4)
C290.105 (4)0.102 (4)0.104 (4)−0.002 (2)0.009 (2)0.004 (2)
C300.095 (3)0.093 (3)0.097 (3)−0.001 (2)0.008 (2)0.002 (2)
C310.027 (4)0.039 (4)0.036 (4)0.008 (3)0.002 (3)0.000 (3)
C320.045 (4)0.052 (4)0.036 (4)−0.001 (3)−0.007 (3)0.000 (3)
C330.052 (5)0.038 (4)0.059 (5)0.009 (3)0.003 (4)0.010 (4)
C340.052 (5)0.052 (4)0.047 (4)−0.001 (4)0.001 (4)−0.022 (3)
C350.036 (4)0.046 (4)0.031 (3)0.000 (3)−0.007 (3)−0.013 (3)
C360.043 (4)0.038 (4)0.057 (4)−0.007 (3)−0.004 (4)−0.009 (3)
C370.048 (5)0.041 (4)0.059 (5)0.000 (3)−0.007 (4)−0.011 (3)
C380.042 (4)0.049 (4)0.034 (3)−0.007 (4)−0.010 (3)−0.002 (3)
C390.056 (5)0.041 (4)0.037 (4)−0.006 (3)−0.011 (4)0.001 (3)
C400.048 (4)0.042 (4)0.039 (4)0.002 (3)−0.009 (3)−0.009 (3)
C410.050 (5)0.067 (5)0.040 (4)−0.011 (4)−0.014 (4)0.001 (3)
C420.040 (4)0.048 (4)0.039 (4)−0.003 (3)0.005 (3)−0.012 (3)
C430.043 (4)0.054 (5)0.068 (5)−0.004 (4)−0.003 (4)−0.027 (4)
C440.035 (4)0.047 (4)0.071 (5)0.002 (3)0.007 (4)−0.014 (4)
O1W0.103 (14)0.074 (12)0.067 (11)−0.033 (11)0.046 (11)−0.003 (10)
O2W0.136 (17)0.177 (18)0.097 (14)0.039 (14)0.068 (13)0.054 (14)

Geometric parameters (Å, °)

Cu1—O4i1.939 (3)C12—C151.516 (8)
Cu1—N71.951 (4)C13—C141.379 (8)
Cu1—O61.954 (4)C13—H130.9300
Cu1—N6ii1.983 (5)C14—H140.9300
Cu2—O2iii1.937 (4)C16—H160.9300
Cu2—O91.943 (4)C17—C181.324 (8)
Cu2—N31.966 (5)C17—H170.9300
Cu2—N21.989 (6)C18—H180.9300
N1—C281.331 (9)C19—C201.502 (8)
N1—C291.346 (11)C19—H19A0.9700
N1—C271.445 (10)C19—H19B0.9700
N2—C301.332 (10)C20—C221.361 (8)
N2—C281.333 (9)C20—C211.379 (9)
N3—C311.324 (7)C21—C22vii1.377 (9)
N3—C321.367 (7)C21—H210.9300
N4—C311.329 (7)C22—C21vii1.377 (9)
N4—C331.362 (7)C22—H220.9300
N4—C341.465 (7)C24—C26viii1.375 (12)
N5—C421.341 (7)C24—C251.393 (12)
N5—C431.358 (8)C24—H240.9300
N5—C411.455 (8)C25—C261.328 (12)
N6—C421.329 (7)C25—C271.552 (12)
N6—C441.372 (7)C26—C24viii1.375 (12)
N6—Cu1iv1.983 (5)C26—H260.9300
N7—C161.324 (7)C27—H27A0.9700
N7—C171.386 (7)C27—H27B0.9700
N8—C161.323 (7)C28—H280.9300
N8—C181.374 (7)C29—C301.319 (12)
N8—C191.474 (7)C29—H290.9300
O1—C11.224 (7)C30—H300.9300
O2—C11.281 (7)C31—H310.9300
O2—Cu2v1.937 (4)C32—C331.334 (8)
O3—C81.233 (7)C32—H320.9300
O4—C81.262 (6)C33—H330.9300
O4—Cu1vi1.939 (3)C34—C351.498 (8)
O5—C51.376 (6)C34—H34A0.9700
O5—C91.382 (6)C34—H34B0.9700
O6—C151.291 (7)C35—C401.355 (8)
O7—C151.201 (7)C35—C361.371 (8)
O8—C231.219 (7)C36—C371.377 (8)
O9—C231.271 (7)C36—H360.9300
C1—C21.494 (7)C37—C381.398 (8)
C2—C71.382 (7)C37—H370.9300
C2—C31.383 (7)C38—C391.369 (9)
C3—C41.373 (8)C38—C411.508 (9)
C3—H30.9300C39—C401.372 (9)
C4—C51.378 (8)C39—H390.9300
C4—H40.9300C40—H400.9300
C5—C61.364 (7)C41—H41A0.9700
C6—C71.383 (7)C41—H41B0.9700
C6—H60.9300C42—H420.9300
C7—C81.515 (7)C43—C441.360 (8)
C9—C101.364 (8)C43—H430.9300
C9—C141.369 (8)C44—H440.9300
C10—C111.387 (7)O1W—H1WA0.8506
C10—H100.9300O1W—H1WB0.8499
C11—C121.390 (7)O2W—H2WA0.8504
C11—C231.488 (8)O2W—H2WB0.8500
C12—C131.367 (8)
O4i—Cu1—N796.09 (17)N8—C18—H18126.3
O4i—Cu1—O6167.24 (17)N8—C19—C20111.9 (5)
N7—Cu1—O690.15 (17)N8—C19—H19A109.2
O4i—Cu1—N6ii88.99 (18)C20—C19—H19A109.2
N7—Cu1—N6ii169.2 (2)N8—C19—H19B109.2
O6—Cu1—N6ii86.79 (18)C20—C19—H19B109.2
O2iii—Cu2—O9167.58 (17)H19A—C19—H19B107.9
O2iii—Cu2—N393.20 (18)C22—C20—C21117.9 (6)
O9—Cu2—N391.71 (18)C22—C20—C19120.8 (6)
O2iii—Cu2—N292.5 (2)C21—C20—C19121.3 (6)
O9—Cu2—N286.7 (2)C22vii—C21—C20120.8 (6)
N3—Cu2—N2160.3 (2)C22vii—C21—H21119.6
C28—N1—C29105.8 (8)C20—C21—H21119.6
C28—N1—C27125.6 (8)C20—C22—C21vii121.3 (6)
C29—N1—C27128.6 (8)C20—C22—H22119.4
C30—N2—C28103.3 (7)C21vii—C22—H22119.4
C30—N2—Cu2131.3 (6)O8—C23—O9123.5 (6)
C28—N2—Cu2123.7 (5)O8—C23—C11121.3 (5)
C31—N3—C32104.5 (5)O9—C23—C11115.3 (5)
C31—N3—Cu2126.6 (4)C26viii—C24—C25119.0 (11)
C32—N3—Cu2128.7 (4)C26viii—C24—H24120.5
C31—N4—C33106.2 (5)C25—C24—H24120.5
C31—N4—C34126.4 (5)C26—C25—C24117.8 (10)
C33—N4—C34127.3 (6)C26—C25—C27122.6 (10)
C42—N5—C43106.1 (6)C24—C25—C27119.5 (10)
C42—N5—C41125.6 (6)C25—C26—C24viii123.2 (11)
C43—N5—C41128.2 (6)C25—C26—H26118.4
C42—N6—C44105.6 (5)C24viii—C26—H26118.4
C42—N6—Cu1iv126.5 (4)N1—C27—C25110.1 (8)
C44—N6—Cu1iv127.4 (5)N1—C27—H27A109.6
C16—N7—C17105.7 (5)C25—C27—H27A109.6
C16—N7—Cu1126.2 (4)N1—C27—H27B109.6
C17—N7—Cu1128.1 (4)C25—C27—H27B109.6
C16—N8—C18107.2 (5)H27A—C27—H27B108.2
C16—N8—C19126.1 (5)N1—C28—N2112.0 (8)
C18—N8—C19126.6 (5)N1—C28—H28124.0
C1—O2—Cu2v110.5 (4)N2—C28—H28124.0
C8—O4—Cu1vi120.7 (4)C30—C29—N1106.8 (10)
C5—O5—C9119.2 (4)C30—C29—H29126.6
C15—O6—Cu1107.4 (4)N1—C29—H29126.6
C23—O9—Cu2110.0 (4)C29—C30—N2112.0 (10)
O1—C1—O2124.1 (6)C29—C30—H30124.0
O1—C1—C2120.9 (5)N2—C30—H30124.0
O2—C1—C2115.0 (5)N3—C31—N4112.2 (5)
C7—C2—C3118.1 (5)N3—C31—H31123.9
C7—C2—C1124.6 (5)N4—C31—H31123.9
C3—C2—C1117.2 (5)C33—C32—N3109.8 (6)
C4—C3—C2122.3 (5)C33—C32—H32125.1
C4—C3—H3118.9N3—C32—H32125.1
C2—C3—H3118.9C32—C33—N4107.3 (6)
C3—C4—C5118.7 (5)C32—C33—H33126.4
C3—C4—H4120.7N4—C33—H33126.4
C5—C4—H4120.7N4—C34—C35112.7 (5)
C6—C5—O5124.8 (5)N4—C34—H34A109.1
C6—C5—C4120.1 (5)C35—C34—H34A109.1
O5—C5—C4115.0 (5)N4—C34—H34B109.1
C5—C6—C7121.0 (5)C35—C34—H34B109.1
C5—C6—H6119.5H34A—C34—H34B107.8
C7—C6—H6119.5C40—C35—C36119.0 (6)
C2—C7—C6119.8 (5)C40—C35—C34121.8 (6)
C2—C7—C8122.1 (5)C36—C35—C34119.2 (6)
C6—C7—C8118.0 (5)C35—C36—C37120.7 (6)
O3—C8—O4126.0 (5)C35—C36—H36119.7
O3—C8—C7118.8 (5)C37—C36—H36119.7
O4—C8—C7115.2 (5)C36—C37—C38120.2 (6)
C10—C9—C14120.3 (5)C36—C37—H37119.9
C10—C9—O5117.8 (5)C38—C37—H37119.9
C14—C9—O5121.8 (5)C39—C38—C37117.9 (6)
C9—C10—C11121.3 (5)C39—C38—C41120.8 (6)
C9—C10—H10119.4C37—C38—C41121.3 (6)
C11—C10—H10119.4C38—C39—C40121.0 (6)
C10—C11—C12118.6 (5)C38—C39—H39119.5
C10—C11—C23118.9 (5)C40—C39—H39119.5
C12—C11—C23122.5 (5)C35—C40—C39121.2 (6)
C13—C12—C11118.9 (5)C35—C40—H40119.4
C13—C12—C15117.7 (5)C39—C40—H40119.4
C11—C12—C15123.4 (5)N5—C41—C38114.9 (5)
C12—C13—C14122.3 (5)N5—C41—H41A108.6
C12—C13—H13118.8C38—C41—H41A108.6
C14—C13—H13118.8N5—C41—H41B108.6
C9—C14—C13118.4 (6)C38—C41—H41B108.6
C9—C14—H14120.8H41A—C41—H41B107.5
C13—C14—H14120.8N6—C42—N5111.9 (6)
O7—C15—O6124.6 (6)N6—C42—H42124.1
O7—C15—C12122.6 (6)N5—C42—H42124.1
O6—C15—C12112.2 (5)N5—C43—C44108.0 (6)
N8—C16—N7111.0 (5)N5—C43—H43126.0
N8—C16—H16124.5C44—C43—H43126.0
N7—C16—H16124.5C43—C44—N6108.4 (6)
C18—C17—N7108.8 (5)C43—C44—H44125.8
C18—C17—H17125.6N6—C44—H44125.8
N7—C17—H17125.6H1WA—O1W—H1WB107.7
C17—C18—N8107.4 (5)H2WA—O2W—H2WB107.7
C17—C18—H18126.3
O2iii—Cu2—N2—C30−6.4 (8)C17—N7—C16—N8−0.2 (6)
O9—Cu2—N2—C30161.2 (8)Cu1—N7—C16—N8178.3 (3)
N3—Cu2—N2—C30−113.0 (9)C16—N7—C17—C180.2 (6)
O2iii—Cu2—N2—C28156.5 (6)Cu1—N7—C17—C18−178.3 (4)
O9—Cu2—N2—C28−35.9 (6)N7—C17—C18—N8−0.1 (7)
N3—Cu2—N2—C2849.9 (10)C16—N8—C18—C170.0 (6)
O2iii—Cu2—N3—C31−21.3 (4)C19—N8—C18—C17177.2 (5)
O9—Cu2—N3—C31170.1 (4)C16—N8—C19—C2090.6 (7)
N2—Cu2—N3—C3185.2 (8)C18—N8—C19—C20−86.1 (7)
O2iii—Cu2—N3—C32164.4 (5)N8—C19—C20—C22−108.8 (7)
O9—Cu2—N3—C32−4.2 (5)N8—C19—C20—C2171.3 (8)
N2—Cu2—N3—C32−89.1 (8)C22—C20—C21—C22vii−1.0 (11)
O4i—Cu1—N7—C16167.2 (4)C19—C20—C21—C22vii178.9 (6)
O6—Cu1—N7—C16−1.6 (5)C21—C20—C22—C21vii1.0 (11)
N6ii—Cu1—N7—C16−75.0 (11)C19—C20—C22—C21vii−178.9 (6)
O4i—Cu1—N7—C17−14.6 (5)Cu2—O9—C23—O8−8.9 (8)
O6—Cu1—N7—C17176.5 (5)Cu2—O9—C23—C11171.2 (4)
N6ii—Cu1—N7—C17103.1 (10)C10—C11—C23—O8148.2 (6)
O4i—Cu1—O6—C15−16.0 (9)C12—C11—C23—O8−30.0 (9)
N7—Cu1—O6—C15103.5 (4)C10—C11—C23—O9−31.9 (8)
N6ii—Cu1—O6—C15−86.9 (4)C12—C11—C23—O9149.9 (6)
O2iii—Cu2—O9—C23−15.4 (10)C26viii—C24—C25—C262.2 (18)
N3—Cu2—O9—C2397.9 (4)C26viii—C24—C25—C27−176.4 (9)
N2—Cu2—O9—C23−101.8 (4)C24—C25—C26—C24viii−2.3 (19)
Cu2v—O2—C1—O111.7 (8)C27—C25—C26—C24viii176.2 (10)
Cu2v—O2—C1—C2−166.8 (4)C28—N1—C27—C2596.3 (11)
O1—C1—C2—C7139.2 (6)C29—N1—C27—C25−86.4 (12)
O2—C1—C2—C7−42.3 (8)C26—C25—C27—N180.0 (12)
O1—C1—C2—C3−44.3 (8)C24—C25—C27—N1−101.5 (11)
O2—C1—C2—C3134.2 (6)C29—N1—C28—N23.2 (10)
C7—C2—C3—C40.4 (9)C27—N1—C28—N2−178.9 (8)
C1—C2—C3—C4−176.4 (6)C30—N2—C28—N1−2.7 (10)
C2—C3—C4—C50.5 (10)Cu2—N2—C28—N1−169.6 (5)
C9—O5—C5—C621.9 (9)C28—N1—C29—C30−2.4 (11)
C9—O5—C5—C4−160.5 (6)C27—N1—C29—C30179.8 (9)
C3—C4—C5—C6−1.4 (10)N1—C29—C30—N20.8 (12)
C3—C4—C5—O5−179.2 (6)C28—N2—C30—C291.1 (11)
O5—C5—C6—C7179.0 (5)Cu2—N2—C30—C29166.6 (7)
C4—C5—C6—C71.6 (9)C32—N3—C31—N40.5 (6)
C3—C2—C7—C6−0.3 (8)Cu2—N3—C31—N4−174.9 (4)
C1—C2—C7—C6176.2 (5)C33—N4—C31—N3−1.2 (6)
C3—C2—C7—C8176.1 (5)C34—N4—C31—N3−177.4 (5)
C1—C2—C7—C8−7.4 (9)C31—N3—C32—C330.4 (7)
C5—C6—C7—C2−0.7 (8)Cu2—N3—C32—C33175.7 (4)
C5—C6—C7—C8−177.2 (5)N3—C32—C33—N4−1.1 (7)
Cu1vi—O4—C8—O3−13.5 (8)C31—N4—C33—C321.3 (7)
Cu1vi—O4—C8—C7164.6 (3)C34—N4—C33—C32177.5 (5)
C2—C7—C8—O3−61.2 (7)C31—N4—C34—C3596.8 (7)
C6—C7—C8—O3115.3 (6)C33—N4—C34—C35−78.6 (8)
C2—C7—C8—O4120.6 (6)N4—C34—C35—C40114.0 (6)
C6—C7—C8—O4−63.0 (7)N4—C34—C35—C36−67.6 (8)
C5—O5—C9—C10−132.2 (6)C40—C35—C36—C37−2.3 (9)
C5—O5—C9—C1449.9 (8)C34—C35—C36—C37179.3 (6)
C14—C9—C10—C11−3.4 (9)C35—C36—C37—C382.4 (10)
O5—C9—C10—C11178.6 (5)C36—C37—C38—C39−1.0 (9)
C9—C10—C11—C120.6 (9)C36—C37—C38—C41−177.5 (6)
C9—C10—C11—C23−177.6 (5)C37—C38—C39—C40−0.5 (9)
C10—C11—C12—C132.5 (8)C41—C38—C39—C40176.0 (6)
C23—C11—C12—C13−179.3 (6)C36—C35—C40—C390.8 (9)
C10—C11—C12—C15−177.7 (6)C34—C35—C40—C39179.2 (5)
C23—C11—C12—C150.5 (9)C38—C39—C40—C350.6 (9)
C11—C12—C13—C14−3.0 (9)C42—N5—C41—C38−91.1 (7)
C15—C12—C13—C14177.3 (6)C43—N5—C41—C3886.8 (8)
C10—C9—C14—C133.0 (9)C39—C38—C41—N5132.6 (6)
O5—C9—C14—C13−179.1 (6)C37—C38—C41—N5−50.9 (8)
C12—C13—C14—C90.2 (10)C44—N6—C42—N5−0.8 (7)
Cu1—O6—C15—O7−13.0 (7)Cu1iv—N6—C42—N5−173.7 (4)
Cu1—O6—C15—C12158.9 (4)C43—N5—C42—N60.8 (7)
C13—C12—C15—O794.4 (8)C41—N5—C42—N6179.1 (5)
C11—C12—C15—O7−85.4 (8)C42—N5—C43—C44−0.5 (7)
C13—C12—C15—O6−77.7 (7)C41—N5—C43—C44−178.7 (6)
C11—C12—C15—O6102.5 (6)N5—C43—C44—N60.0 (8)
C18—N8—C16—N70.1 (6)C42—N6—C44—C430.5 (7)
C19—N8—C16—N7−177.1 (5)Cu1iv—N6—C44—C43173.3 (4)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) x−1/2, −y+1/2, z−1/2; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+2, −y, −z+1; (viii) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2401).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, S1–19.
  • Bruker (2005). SHELXTL, APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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