supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m2448    [ doi:10.1107/S1600536807042079 ]

Di-[mu]-methoxido-[kappa]4O:O-bis[bis(3-methyl-5-phenyl-1H-pyrazole-[kappa]N2)copper(II)] bis(perchlorate)

H. He and A. G. Sykes

Abstract top

In the title complex, [Cu(CH3O)2(C40H40N8)](ClO4)2, two copper ions are bridged by two methoxide O atoms. Each CuII is further coordinated by two neutral 3-methyl-5-phenyl-1H-pyrazole ligands and adopts a distorted square-planar geometry. The two perchlorate anions lie on opposite sides of the Cu2O2 plane and there is evidence for interaction between two of the O atoms from each perchlorate anion with the CuII centers.

Comment top

3-methyl-5-phenyl-1H-pyrazole has been widely used as starting material for the preparation of the trispyrazolylborate anion, and as a very good ligand for modeling complexes of several metalloenzymes (Tekeste & Vahrenkamp 2007; Jacobsen & Cohen, 2004; Puerta & Cohen, 2003; Parkin, 2004). However, its interaction with transition metal ions is rare. Reported here is the single-crystal structure of a dicopper(II) complex of this ligand.

In the title compound (I) two methoxide anions hold two copper ions together with O as the bridging atoms. The distance between Cu1 and Cu2 is 2.9583 (7) Å. Each copper ion is further coordinated by two pyrazolyl N atoms. Copper adopts an approximate square planar geometry. Atoms N1, N2, N3, N4, Cu1, and Cu2 are almost coplanar with a torsion angle of 3.4 (3)° between the N1/N2/Cu2 and N3/N4/Cu1 planes. The two bridging methoxyl groups are located on either side of this plane. The torsion angles between the O1/Cu1/Cu2 and O2/Cu1/Cu2 planes and that containing the atoms N1/N2/N3/N4/Cu1/Cu2 are 12.30 (16)° and −12.30 (16)°, respectively. The Cu1/O1/Cu2/O2 ring is also planar with an r.m.s. deviation from the best fit meanplane of 0.0002. The O4, O9 and O3, O8 atoms from the two perchlorate anions point towards the Cu1 and Cu2 centers with distances 2.722 (3), 2.755 (3), 2.790 (3), and 2.869 (3) Å for O3—Cu2, O4—Cu1, O8—Cu2, and O9—Cu1, respectively. This indicates some level of interaction between the perchlorate anions and the CuII cations.

Related literature top

For related literature, see: Jacobsen & Cohen (2004); Parkin (2004); Puerta & Cohen (2003); Tekeste & Vahrenkamp (2007).

Experimental top

3-methyl-5-phenyl-1H-pyrazole (0.16 g, 0.1 mmol), prepared according to the literature (Puerta & Cohen, 2003), was dissolved in dichloromethane (10 ml) at room temperature. To this solution, copper(II) perchlorate hexahydrate (0.18 g, 0.05 mmol) in methanol (2 ml) was added. The resulting blue solution was stirred for two hours. The mixture was filtered and the filtrate kept at room temperature. Blue crystals were obtained after one week by slow evaporation.

Refinement top

H atoms on N5, N6, N7, and N8 are refined while the other hydrogen atoms are geometrically constrained and refined in riding mode as follows: methyl C—H = 0.96 Å, Uiso(H) = 1.5Ueq(C); aromatic C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C). High and increasing temperature factors for the C atoms of the C1···C6 and C31···C36 benzene rings suggested possible disorder but this was not investigated further.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b) and publCIF (Version 1.0_c; Westrip, 2007).

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are drawn as small circles of arbitrary radii.
Di-µ-methoxido-κ4O:O-bis[bis(3-methyl-5-phenyl-1H-pyrazole- κN2)copper(II)] bis(perchlorate) top
Crystal data top
[Cu(CH3O)2(C40H40N8)](ClO4)2F000 = 2104
Mr = 1020.85Dx = 1.392 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9998 reflections
a = 13.8398 (12) Åθ = 1.0–25.5º
b = 17.4607 (16) ŵ = 1.04 mm−1
c = 20.3779 (18) ÅT = 293 (2) K
β = 98.3160 (10)ºBlock, green
V = 4872.6 (8) Å30.15 × 0.13 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		9045 independent reflections
Radiation source: fine-focus sealed tube5370 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.074
T = 293(2) Kθmax = 25.5º
φ and ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		h = −16→16
Tmin = 0.859, Tmax = 0.894k = −21→21
48197 measured reflectionsl = −24→24
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)] = 0.049H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.137  w = 1/[σ2(Fo2) + (0.0637P)2 + 2.32P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.003
9045 reflectionsΔρmax = 0.46 e Å−3
599 parametersΔρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu(CH3O)2(C40H40N8)](ClO4)2V = 4872.6 (8) Å3
Mr = 1020.85Z = 4
Monoclinic, P21/cMo Kα
a = 13.8398 (12) ŵ = 1.04 mm−1
b = 17.4607 (16) ÅT = 293 (2) K
c = 20.3779 (18) Å0.15 × 0.13 × 0.11 mm
β = 98.3160 (10)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		9045 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		5370 reflections with I > 2σ(I)
Tmin = 0.859, Tmax = 0.894Rint = 0.074
48197 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049599 parameters
wR(F2) = 0.137H atoms treated by a mixture of
independent and constrained refinement
S = 1.00Δρmax = 0.46 e Å−3
9045 reflectionsΔρmin = −0.26 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
C11.3406 (6)0.4300 (5)0.5628 (4)0.145 (4)
H11.33180.46110.59850.175*
C21.4292 (6)0.4221 (6)0.5433 (6)0.150 (4)
H21.48130.44900.56640.180*
C31.4469 (5)0.3770 (5)0.4917 (6)0.129 (4)
H31.50930.37260.48020.155*
C41.3675 (4)0.3376 (4)0.4566 (4)0.115 (3)
H41.37660.30790.42010.138*
C51.2766 (4)0.3425 (3)0.4754 (3)0.0762 (17)
C61.2628 (5)0.3900 (5)0.5277 (4)0.116 (3)
H61.20070.39520.53950.139*
C71.1920 (3)0.3031 (3)0.4369 (3)0.0603 (13)
C81.1693 (4)0.2811 (3)0.3721 (3)0.0744 (16)
H81.20950.28580.33950.089*
C91.0756 (4)0.2504 (3)0.3632 (2)0.0599 (13)
C101.0161 (5)0.2209 (4)0.3027 (2)0.100 (2)
H10A1.02880.16720.29820.150*
H10B1.03270.24780.26480.150*
H10C0.94820.22840.30560.150*
C110.6050 (4)0.0721 (4)0.3064 (3)0.104 (2)
H110.61000.11990.32670.125*
C120.5160 (4)0.0492 (4)0.2717 (4)0.138 (3)
H120.46250.08190.26800.165*
C130.5072 (5)−0.0208 (4)0.2432 (4)0.109 (2)
H130.4472−0.03720.22120.130*
C140.5860 (5)−0.0666 (4)0.2469 (3)0.0900 (19)
H140.5808−0.11430.22640.108*
C150.6742 (4)−0.0434 (3)0.2809 (3)0.0735 (16)
H150.7278−0.07600.28330.088*
C160.6847 (3)0.0265 (3)0.3113 (2)0.0541 (12)
C170.7801 (3)0.0507 (2)0.3463 (2)0.0447 (10)
C180.8683 (3)0.0142 (2)0.3584 (2)0.0546 (12)
H180.8818−0.03530.34550.065*
C190.9336 (3)0.0642 (2)0.3935 (2)0.0455 (11)
C201.0388 (3)0.0524 (3)0.4190 (3)0.0712 (15)
H20A1.07740.06640.38540.107*
H20B1.0499−0.00050.43050.107*
H20C1.05690.08360.45760.107*
C211.0570 (4)0.5592 (3)0.7408 (3)0.0678 (14)
H211.00180.58930.74170.081*
C221.1443 (5)0.5828 (3)0.7750 (3)0.0867 (18)
H221.14730.62820.79900.104*
C231.2264 (5)0.5408 (4)0.7742 (3)0.105 (2)
H231.28570.55770.79680.126*
C241.2208 (4)0.4735 (4)0.7399 (4)0.142 (4)
H241.27640.44370.73980.171*
C251.1329 (4)0.4497 (4)0.7052 (4)0.108 (2)
H251.13020.40410.68150.129*
C261.0491 (3)0.4922 (3)0.7051 (2)0.0522 (12)
C270.9549 (3)0.4678 (2)0.6698 (2)0.0463 (11)
C280.8646 (3)0.5012 (3)0.6625 (2)0.0571 (13)
H280.84910.54800.68020.069*
C290.8006 (3)0.4529 (2)0.6241 (2)0.0499 (11)
C300.6931 (3)0.4608 (3)0.6028 (3)0.0749 (16)
H30A0.67570.43740.56010.112*
H30B0.67600.51410.60010.112*
H30C0.65860.43600.63450.112*
C310.3854 (5)0.1563 (5)0.5683 (4)0.138 (3)
H310.37970.18020.60840.166*
C320.3057 (6)0.1176 (7)0.5348 (6)0.156 (4)
H320.24680.11690.55170.187*
C330.3140 (8)0.0807 (6)0.4775 (7)0.166 (5)
H330.26160.05290.45580.199*
C340.3981 (6)0.0844 (6)0.4519 (5)0.176 (4)
H340.40320.06030.41180.211*
C350.4776 (5)0.1240 (5)0.4853 (5)0.140 (3)
H350.53550.12590.46720.168*
C360.4724 (4)0.1602 (4)0.5438 (4)0.0803 (18)
C370.5561 (4)0.2010 (3)0.5797 (3)0.0625 (14)
C380.5858 (4)0.2149 (3)0.6456 (3)0.0786 (17)
H380.55310.20060.68050.094*
C390.6743 (4)0.2547 (3)0.6508 (2)0.0597 (13)
C400.7380 (5)0.2824 (3)0.7117 (2)0.0892 (19)
H40A0.80500.28190.70430.134*
H40B0.73050.24950.74830.134*
H40C0.71960.33370.72160.134*
C410.9313 (4)0.3916 (2)0.4734 (2)0.0634 (13)
H41A0.87260.42100.47290.095*
H41B0.94440.38450.42890.095*
H41C0.98490.41830.49870.095*
C420.8036 (3)0.1299 (2)0.5335 (2)0.0563 (12)
H42A0.76120.10010.50180.084*
H42B0.77470.13540.57330.084*
H42C0.86550.10450.54360.084*
N10.6971 (3)0.2664 (2)0.59041 (17)0.0473 (9)
N20.8477 (2)0.3908 (2)0.60875 (17)0.0466 (9)
N31.0426 (2)0.2502 (2)0.42132 (17)0.0481 (9)
N40.8888 (2)0.12950 (19)0.40318 (17)0.0449 (9)
N50.6243 (3)0.2336 (2)0.5482 (2)0.0530 (11)
N60.9418 (3)0.4019 (2)0.63658 (19)0.0497 (10)
N71.1142 (3)0.2828 (2)0.4645 (2)0.0515 (10)
N80.7954 (3)0.1194 (2)0.3738 (2)0.0487 (11)
O10.91953 (19)0.31904 (14)0.50286 (13)0.0421 (7)
O20.81754 (18)0.20320 (14)0.50649 (13)0.0388 (6)
O30.6912 (2)0.35140 (18)0.44912 (16)0.0700 (10)
O40.7729 (3)0.2916 (2)0.36896 (16)0.0741 (10)
O50.6229 (3)0.3515 (3)0.3371 (2)0.1208 (17)
O60.6324 (3)0.2375 (2)0.39973 (18)0.0806 (11)
O71.1032 (2)0.28455 (17)0.61243 (16)0.0623 (9)
O80.9631 (2)0.22786 (18)0.64244 (15)0.0600 (8)
O91.0497 (2)0.16613 (17)0.56659 (15)0.0612 (9)
O101.1167 (3)0.17362 (19)0.67927 (16)0.0747 (10)
Cl10.67889 (10)0.30902 (7)0.38767 (6)0.0641 (4)
Cl21.05868 (8)0.21234 (6)0.62539 (5)0.0481 (3)
Cu10.92039 (4)0.22382 (3)0.45477 (2)0.04138 (16)
Cu20.81615 (4)0.29804 (3)0.55465 (2)0.04131 (16)
H431.107 (3)0.283 (3)0.502 (2)0.056 (16)*
H440.983 (3)0.372 (2)0.6319 (17)0.026 (11)*
H450.762 (3)0.149 (2)0.3770 (19)0.028 (13)*
H460.628 (3)0.231 (3)0.512 (2)0.053 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.114 (6)0.194 (9)0.118 (6)−0.086 (6)−0.017 (5)−0.001 (6)
C20.053 (5)0.170 (10)0.214 (12)−0.032 (6)−0.024 (6)0.066 (8)
C30.040 (4)0.101 (6)0.245 (12)0.007 (4)0.016 (6)0.055 (7)
C40.055 (4)0.076 (4)0.217 (9)0.004 (3)0.029 (5)0.039 (5)
C50.044 (3)0.076 (4)0.109 (5)−0.008 (3)0.011 (3)0.027 (4)
C60.079 (5)0.163 (7)0.105 (6)−0.065 (5)0.010 (4)−0.004 (5)
C70.045 (3)0.063 (3)0.077 (4)0.007 (2)0.022 (3)0.018 (3)
C80.088 (4)0.067 (4)0.081 (4)−0.002 (3)0.053 (3)0.008 (3)
C90.086 (4)0.053 (3)0.044 (3)−0.003 (3)0.018 (3)0.005 (2)
C100.163 (6)0.101 (5)0.036 (3)−0.027 (4)0.012 (4)−0.003 (3)
C110.054 (4)0.093 (5)0.156 (6)−0.005 (3)−0.015 (4)−0.068 (4)
C120.057 (4)0.121 (6)0.222 (9)−0.003 (4)−0.025 (5)−0.076 (6)
C130.070 (4)0.119 (6)0.129 (6)−0.034 (4)−0.010 (4)−0.042 (5)
C140.095 (5)0.077 (4)0.094 (5)−0.038 (4)0.000 (4)−0.035 (4)
C150.070 (4)0.069 (4)0.078 (4)−0.017 (3)−0.002 (3)−0.025 (3)
C160.053 (3)0.049 (3)0.059 (3)−0.015 (2)0.001 (2)−0.014 (2)
C170.053 (3)0.037 (2)0.044 (3)−0.007 (2)0.004 (2)−0.007 (2)
C180.060 (3)0.036 (3)0.065 (3)0.004 (2)0.002 (2)−0.012 (2)
C190.044 (3)0.042 (3)0.048 (3)0.005 (2)0.000 (2)−0.006 (2)
C200.057 (3)0.064 (3)0.087 (4)0.017 (3)−0.008 (3)−0.008 (3)
C210.067 (3)0.060 (3)0.075 (4)−0.006 (3)0.006 (3)−0.022 (3)
C220.088 (5)0.078 (4)0.090 (4)−0.023 (4)−0.002 (4)−0.038 (3)
C230.064 (4)0.128 (6)0.118 (5)−0.035 (4)−0.003 (4)−0.054 (5)
C240.049 (4)0.143 (7)0.227 (9)−0.002 (4)−0.007 (5)−0.114 (7)
C250.052 (4)0.099 (5)0.166 (7)−0.002 (3)−0.003 (4)−0.080 (5)
C260.050 (3)0.049 (3)0.058 (3)−0.008 (2)0.008 (2)−0.017 (2)
C270.048 (3)0.042 (3)0.048 (3)−0.002 (2)0.006 (2)−0.009 (2)
C280.056 (3)0.040 (3)0.074 (3)0.009 (2)0.004 (3)−0.019 (2)
C290.049 (3)0.045 (3)0.055 (3)0.007 (2)0.002 (2)−0.005 (2)
C300.059 (3)0.067 (3)0.093 (4)0.016 (3)−0.008 (3)−0.013 (3)
C310.079 (5)0.192 (9)0.146 (7)−0.037 (5)0.028 (5)0.055 (6)
C320.060 (5)0.189 (11)0.216 (12)−0.048 (6)0.007 (7)0.067 (9)
C330.089 (7)0.148 (9)0.246 (14)−0.055 (6)−0.021 (9)0.034 (9)
C340.103 (6)0.212 (11)0.205 (10)−0.082 (7)−0.005 (7)−0.065 (8)
C350.075 (5)0.170 (8)0.174 (8)−0.055 (5)0.012 (5)−0.048 (7)
C360.042 (3)0.082 (4)0.116 (5)−0.010 (3)0.008 (3)0.030 (4)
C370.049 (3)0.068 (3)0.073 (4)−0.001 (3)0.016 (3)0.020 (3)
C380.074 (4)0.095 (4)0.074 (4)0.002 (3)0.032 (3)0.024 (3)
C390.070 (3)0.065 (3)0.045 (3)0.008 (3)0.012 (3)0.009 (2)
C400.125 (5)0.103 (5)0.040 (3)−0.001 (4)0.011 (3)0.006 (3)
C410.071 (3)0.041 (3)0.079 (4)−0.011 (2)0.014 (3)0.004 (2)
C420.061 (3)0.041 (3)0.066 (3)−0.006 (2)0.004 (2)0.006 (2)
N10.048 (2)0.057 (2)0.038 (2)−0.0045 (18)0.0074 (17)−0.0015 (18)
N20.040 (2)0.048 (2)0.050 (2)0.0016 (17)−0.0012 (17)−0.0106 (17)
N30.046 (2)0.058 (2)0.041 (2)−0.0086 (18)0.0082 (18)−0.0062 (18)
N40.035 (2)0.046 (2)0.051 (2)0.0014 (16)−0.0033 (17)−0.0119 (17)
N50.047 (2)0.062 (3)0.050 (3)−0.0082 (19)0.008 (2)0.003 (2)
N60.039 (2)0.041 (2)0.067 (3)0.0070 (19)0.003 (2)−0.0185 (19)
N70.043 (2)0.070 (3)0.043 (3)−0.0155 (19)0.012 (2)−0.002 (2)
N80.039 (2)0.040 (2)0.063 (3)0.0051 (19)−0.0055 (19)−0.017 (2)
O10.0455 (17)0.0345 (16)0.0464 (17)−0.0067 (13)0.0071 (13)−0.0025 (13)
O20.0406 (16)0.0321 (15)0.0427 (16)−0.0039 (12)0.0022 (13)−0.0004 (12)
O30.082 (2)0.060 (2)0.069 (2)0.0104 (18)0.0119 (19)−0.0156 (18)
O40.086 (3)0.087 (3)0.051 (2)0.027 (2)0.0145 (19)−0.0009 (18)
O50.140 (4)0.122 (4)0.089 (3)0.055 (3)−0.020 (3)0.038 (3)
O60.090 (3)0.067 (2)0.078 (3)−0.009 (2)−0.012 (2)−0.009 (2)
O70.068 (2)0.0473 (19)0.070 (2)−0.0116 (16)0.0054 (18)−0.0071 (16)
O80.062 (2)0.070 (2)0.0490 (19)0.0081 (17)0.0131 (16)−0.0004 (16)
O90.075 (2)0.056 (2)0.0518 (19)0.0008 (17)0.0075 (16)−0.0175 (16)
O100.092 (3)0.066 (2)0.059 (2)0.027 (2)−0.0120 (19)−0.0032 (18)
Cl10.0831 (9)0.0561 (8)0.0482 (7)0.0204 (7)−0.0069 (6)0.0045 (6)
Cl20.0587 (7)0.0424 (6)0.0413 (6)0.0062 (5)0.0008 (5)−0.0058 (5)
Cu10.0388 (3)0.0408 (3)0.0432 (3)−0.0056 (2)0.0013 (2)−0.0087 (2)
Cu20.0413 (3)0.0400 (3)0.0414 (3)−0.0044 (2)0.0020 (2)−0.0067 (2)
Geometric parameters (Å, °) top
C1—C21.351 (11)C30—H30B0.9600
C1—C61.391 (8)C30—H30C0.9600
C1—H10.9300C31—C361.372 (8)
C2—C31.363 (12)C31—C321.386 (11)
C2—H20.9300C31—H310.9300
C3—C41.402 (10)C32—C331.353 (13)
C3—H30.9300C32—H320.9300
C4—C51.369 (7)C33—C341.344 (12)
C4—H40.9300C33—H330.9300
C5—C61.386 (9)C34—C351.391 (9)
C5—C71.481 (7)C34—H340.9300
C6—H60.9300C35—C361.360 (9)
C7—N71.334 (6)C35—H350.9300
C7—C81.368 (7)C36—C371.462 (8)
C8—C91.391 (7)C37—N51.343 (6)
C8—H80.9300C37—C381.367 (7)
C9—N31.329 (5)C38—C391.399 (7)
C9—C101.473 (7)C38—H380.9300
C10—H10A0.9600C39—N11.330 (5)
C10—H10B0.9600C39—C401.495 (7)
C10—H10C0.9600C40—H40A0.9600
C11—C161.352 (7)C40—H40B0.9600
C11—C121.388 (7)C40—H40C0.9600
C11—H110.9300C41—O11.421 (5)
C12—C131.350 (9)C41—H41A0.9600
C12—H120.9300C41—H41B0.9600
C13—C141.346 (8)C41—H41C0.9600
C13—H130.9300C42—O21.418 (5)
C14—C151.375 (7)C42—H42A0.9600
C14—H140.9300C42—H42B0.9600
C15—C161.367 (6)C42—H42C0.9600
C15—H150.9300N1—N51.354 (5)
C16—C171.470 (6)N1—Cu21.975 (3)
C17—N81.329 (5)N2—N61.357 (5)
C17—C181.367 (6)N2—Cu21.973 (3)
C18—C191.380 (6)N3—N71.353 (5)
C18—H180.9300N3—Cu11.968 (3)
C19—N41.325 (5)N4—N81.356 (5)
C19—C201.488 (6)N4—Cu11.969 (3)
C20—H20A0.9600N5—H460.75 (4)
C20—H20B0.9600N6—H440.80 (3)
C20—H20C0.9600N7—H430.78 (4)
C21—C221.367 (7)N8—H450.70 (4)
C21—C261.374 (6)O1—Cu11.931 (3)
C21—H210.9300O1—Cu21.932 (3)
C22—C231.354 (8)O2—Cu11.924 (3)
C22—H220.9300O2—Cu21.926 (2)
C23—C241.364 (8)O3—Cl11.443 (3)
C23—H230.9300O3—Cu22.722 (3)
C24—C251.380 (7)O4—Cl11.441 (4)
C24—H240.9300O4—Cu12.755 (3)
C25—C261.376 (6)O5—Cl11.407 (4)
C25—H250.9300O6—Cl11.441 (4)
C26—C271.458 (6)O7—Cl21.444 (3)
C27—N61.334 (5)O8—Cl21.441 (3)
C27—C281.367 (6)O8—Cu22.790 (3)
C28—C291.382 (6)O9—Cl21.435 (3)
C28—H280.9300O9—Cu12.869 (3)
C29—N21.325 (5)O10—Cl21.433 (3)
C29—C301.495 (6)Cu1—Cu22.9583 (7)
C30—H30A0.9600
C2—C1—C6117.7 (9)C31—C36—C37121.0 (7)
C2—C1—H1121.1N5—C37—C38105.2 (5)
C6—C1—H1121.1N5—C37—C36121.8 (5)
C1—C2—C3123.9 (9)C38—C37—C36133.0 (5)
C1—C2—H2118.0C37—C38—C39107.4 (5)
C3—C2—H2118.0C37—C38—H38126.3
C2—C3—C4117.5 (8)C39—C38—H38126.3
C2—C3—H3121.2N1—C39—C38109.1 (5)
C4—C3—H3121.2N1—C39—C40121.8 (5)
C5—C4—C3120.7 (8)C38—C39—C40129.0 (5)
C5—C4—H4119.6C39—C40—H40A109.5
C3—C4—H4119.6C39—C40—H40B109.5
C4—C5—C6119.1 (6)H40A—C40—H40B109.5
C4—C5—C7120.7 (7)C39—C40—H40C109.5
C6—C5—C7120.0 (5)H40A—C40—H40C109.5
C5—C6—C1120.9 (7)H40B—C40—H40C109.5
C5—C6—H6119.5O1—C41—H41A109.5
C1—C6—H6119.5O1—C41—H41B109.5
N7—C7—C8104.2 (5)H41A—C41—H41B109.5
N7—C7—C5121.6 (5)O1—C41—H41C109.5
C8—C7—C5134.1 (5)H41A—C41—H41C109.5
C7—C8—C9108.3 (4)H41B—C41—H41C109.5
C7—C8—H8125.9O2—C42—H42A109.5
C9—C8—H8125.9O2—C42—H42B109.5
N3—C9—C8108.6 (4)H42A—C42—H42B109.5
N3—C9—C10121.6 (5)O2—C42—H42C109.5
C8—C9—C10129.8 (5)H42A—C42—H42C109.5
C9—C10—H10A109.5H42B—C42—H42C109.5
C9—C10—H10B109.5C39—N1—N5105.6 (4)
H10A—C10—H10B109.5C39—N1—Cu2135.0 (3)
C9—C10—H10C109.5N5—N1—Cu2117.9 (3)
H10A—C10—H10C109.5C29—N2—N6105.1 (3)
H10B—C10—H10C109.5C29—N2—Cu2136.6 (3)
C16—C11—C12121.5 (5)N6—N2—Cu2118.2 (3)
C16—C11—H11119.3C9—N3—N7105.4 (4)
C12—C11—H11119.3C9—N3—Cu1137.1 (3)
C13—C12—C11119.8 (6)N7—N3—Cu1117.3 (3)
C13—C12—H12120.1C19—N4—N8105.1 (3)
C11—C12—H12120.1C19—N4—Cu1136.6 (3)
C14—C13—C12119.5 (6)N8—N4—Cu1117.9 (3)
C14—C13—H13120.2C37—N5—N1112.6 (4)
C12—C13—H13120.2C37—N5—H46127 (4)
C13—C14—C15120.4 (6)N1—N5—H46120 (4)
C13—C14—H14119.8C27—N6—N2112.7 (4)
C15—C14—H14119.8C27—N6—H44126 (3)
C16—C15—C14121.3 (6)N2—N6—H44121 (3)
C16—C15—H15119.3C7—N7—N3113.4 (4)
C14—C15—H15119.3C7—N7—H43130 (4)
C11—C16—C15117.4 (5)N3—N7—H43116 (3)
C11—C16—C17122.2 (4)C17—N8—N4112.7 (4)
C15—C16—C17120.4 (5)C17—N8—H45129 (3)
N8—C17—C18105.2 (4)N4—N8—H45118 (3)
N8—C17—C16122.8 (4)C41—O1—Cu1123.0 (3)
C18—C17—C16132.0 (4)C41—O1—Cu2122.6 (3)
C17—C18—C19107.4 (4)Cu1—O1—Cu299.97 (11)
C17—C18—H18126.3C42—O2—Cu1122.3 (2)
C19—C18—H18126.3C42—O2—Cu2124.5 (3)
N4—C19—C18109.6 (4)Cu1—O2—Cu2100.42 (11)
N4—C19—C20121.5 (4)Cl1—O3—Cu2119.47 (17)
C18—C19—C20128.9 (4)Cl1—O4—Cu1122.49 (18)
C19—C20—H20A109.5Cl2—O8—Cu2122.50 (16)
C19—C20—H20B109.5Cl2—O9—Cu1115.77 (17)
H20A—C20—H20B109.5O5—Cl1—O4109.9 (2)
C19—C20—H20C109.5O5—Cl1—O6111.7 (3)
H20A—C20—H20C109.5O4—Cl1—O6107.7 (2)
H20B—C20—H20C109.5O5—Cl1—O3110.4 (3)
C22—C21—C26121.6 (5)O4—Cl1—O3109.9 (2)
C22—C21—H21119.2O6—Cl1—O3107.2 (2)
C26—C21—H21119.2O10—Cl2—O9110.2 (2)
C23—C22—C21120.8 (5)O10—Cl2—O8109.6 (2)
C23—C22—H22119.6O9—Cl2—O8109.57 (19)
C21—C22—H22119.6O10—Cl2—O7110.2 (2)
C22—C23—C24119.1 (5)O9—Cl2—O7109.0 (2)
C22—C23—H23120.4O8—Cl2—O7108.08 (19)
C24—C23—H23120.4O2—Cu1—O179.85 (11)
C23—C24—C25120.2 (6)O2—Cu1—N3167.14 (13)
C23—C24—H24119.9O1—Cu1—N392.45 (13)
C25—C24—H24119.9O2—Cu1—N490.65 (13)
C26—C25—C24121.3 (5)O1—Cu1—N4166.97 (13)
C26—C25—H25119.4N3—Cu1—N498.42 (14)
C24—C25—H25119.4O2—Cu1—O483.65 (11)
C21—C26—C25117.1 (4)O1—Cu1—O483.90 (11)
C21—C26—C27120.5 (4)N3—Cu1—O4105.91 (13)
C25—C26—C27122.5 (4)N4—Cu1—O486.20 (12)
N6—C27—C28104.9 (4)O2—Cu1—O985.70 (10)
N6—C27—C26123.2 (4)O1—Cu1—O987.03 (10)
C28—C27—C26131.8 (4)N3—Cu1—O983.62 (12)
C27—C28—C29107.6 (4)N4—Cu1—O9101.25 (12)
C27—C28—H28126.2O4—Cu1—O9167.07 (9)
C29—C28—H28126.2O2—Cu1—Cu239.82 (7)
N2—C29—C28109.6 (4)O1—Cu1—Cu240.03 (8)
N2—C29—C30120.6 (4)N3—Cu1—Cu2131.67 (10)
C28—C29—C30129.7 (4)N4—Cu1—Cu2129.88 (10)
C29—C30—H30A109.5O4—Cu1—Cu281.86 (7)
C29—C30—H30B109.5O9—Cu1—Cu285.27 (6)
H30A—C30—H30B109.5O2—Cu2—O179.76 (11)
C29—C30—H30C109.5O2—Cu2—N2166.64 (13)
H30A—C30—H30C109.5O1—Cu2—N291.59 (13)
H30B—C30—H30C109.5O2—Cu2—N191.03 (13)
C36—C31—C32121.5 (9)O1—Cu2—N1168.03 (13)
C36—C31—H31119.3N2—Cu2—N198.78 (14)
C32—C31—H31119.3O2—Cu2—O386.78 (10)
C33—C32—C31119.8 (10)O1—Cu2—O386.53 (11)
C33—C32—H32120.1N2—Cu2—O3102.96 (12)
C31—C32—H32120.1N1—Cu2—O385.33 (13)
C34—C33—C32119.9 (11)O2—Cu2—O883.63 (10)
C34—C33—H33120.1O1—Cu2—O884.54 (10)
C32—C33—H33120.1N2—Cu2—O885.44 (12)
C33—C34—C35120.2 (10)N1—Cu2—O8102.14 (12)
C33—C34—H34119.9O3—Cu2—O8167.91 (9)
C35—C34—H34119.9O2—Cu2—Cu139.76 (8)
C36—C35—C34121.4 (8)O1—Cu2—Cu140.00 (8)
C36—C35—H35119.3N2—Cu2—Cu1130.82 (10)
C34—C35—H35119.3N1—Cu2—Cu1130.35 (10)
C35—C36—C31117.2 (7)O3—Cu2—Cu185.62 (7)
C35—C36—C37121.8 (6)O8—Cu2—Cu182.30 (6)
Acknowledgements top

This work was supported by NSF–EPSCoR (grant No. EPS-0554609), including the purchase of a Bruker APEXII X-ray diffractometer.

references
References top

Bruker (2006). APEX2 (Version 2.1), SAINT-NT (Version 6.0) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Jacobsen, F. E. & Cohen, S. M. (2004). Inorg. Chem. 43, 3038–3047.

Parkin, G. (2004). Chem. Rev. 104, 699–767.

Puerta, D. T. & Cohen, S. M. (2003). Inorg. Chem. 42, 3423–3430.

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

Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Tekeste, T. & Vahrenkamp, H. (2007). Inorg. Chim. Acta, 360, 1523–1528.

Westrip, S. P. (2007). publCIF. In preparation.