Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100017455/de1163sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100017455/de1163Isup2.hkl |
CCDC reference: 159982
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to either 0.95 Å (Ar—H) or 0.99 Å (CH2) and N—H set to 0.88 Å.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. Molecular configuration and atom-numbering scheme showing 30% probability ellipsoids. |
[Cu2(C4H5N3)2(C8H6NO4)4] | Dx = 1.616 Mg m−3 |
Mr = 1037.85 | Melting point: 465-467 K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.134 (5) Å | Cell parameters from 8113 reflections |
b = 18.9575 (8) Å | θ = 2.9–27.5° |
c = 14.0859 (6) Å | µ = 1.08 mm−1 |
β = 111.159 (3)° | T = 150 K |
V = 4266.9 (13) Å3 | Plate, green |
Z = 4 | 0.50 × 0.10 × 0.02 mm |
F(000) = 2120 |
Enraf Nonius KappaCCD area detector diffractometer | 9074 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 3921 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.127 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −21→21 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −24→24 |
Tmin = 0.613, Tmax = 0.979 | l = −18→18 |
21389 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0357P)2] where P = (Fo2 + 2Fc2)/3 |
9074 reflections | (Δ/σ)max = 0.001 |
613 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
[Cu2(C4H5N3)2(C8H6NO4)4] | V = 4266.9 (13) Å3 |
Mr = 1037.85 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.134 (5) Å | µ = 1.08 mm−1 |
b = 18.9575 (8) Å | T = 150 K |
c = 14.0859 (6) Å | 0.50 × 0.10 × 0.02 mm |
β = 111.159 (3)° |
Enraf Nonius KappaCCD area detector diffractometer | 9074 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 3921 reflections with I > 2σ(I) |
Tmin = 0.613, Tmax = 0.979 | Rint = 0.127 |
21389 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 0.51 e Å−3 |
9074 reflections | Δρmin = −0.54 e Å−3 |
613 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.81174 (3) | 0.70652 (4) | 0.02487 (5) | 0.0285 (2) | |
Cu2 | 0.67440 (3) | 0.78285 (4) | −0.00720 (5) | 0.0290 (2) | |
C1A | 0.9219 (3) | 0.8986 (3) | −0.1005 (5) | 0.0375 (16) | |
C11A | 0.8309 (3) | 0.9052 (4) | −0.1115 (6) | 0.060 (2) | |
H11A | 0.8251 | 0.9473 | −0.0730 | 0.075* | |
H12A | 0.7972 | 0.9138 | −0.1842 | 0.075* | |
C12A | 0.7940 (3) | 0.8432 (4) | −0.0763 (4) | 0.0385 (16) | |
O12A | 0.8316 (2) | 0.7852 (2) | −0.0596 (3) | 0.0347 (10) | |
O13A | 0.7257 (2) | 0.8558 (2) | −0.0632 (3) | 0.0371 (10) | |
C2A | 0.9851 (4) | 0.9100 (3) | −0.0075 (5) | 0.0433 (17) | |
H2A | 0.9714 | 0.9168 | 0.0515 | 0.054* | |
C3A | 1.0676 (3) | 0.9115 (4) | 0.0008 (5) | 0.0421 (17) | |
H3A | 1.1112 | 0.9212 | 0.0639 | 0.053* | |
C4A | 1.0842 (3) | 0.8985 (4) | −0.0854 (5) | 0.0430 (17) | |
N41A | 1.1714 (4) | 0.9027 (4) | −0.0800 (6) | 0.075 (2) | |
O41A | 1.2194 (3) | 0.9406 (4) | −0.0186 (5) | 0.099 (2) | |
O42A | 1.1889 (3) | 0.8638 (4) | −0.1418 (5) | 0.122 (3) | |
C5A | 1.0234 (4) | 0.8831 (4) | −0.1776 (5) | 0.0485 (18) | |
H5A | 1.0375 | 0.8718 | −0.2351 | 0.061* | |
C6A | 0.9418 (4) | 0.8846 (3) | −0.1844 (5) | 0.0445 (17) | |
H6A | 0.8984 | 0.8758 | −0.2480 | 0.056* | |
C1B | 0.9525 (3) | 0.8627 (3) | 0.2863 (4) | 0.0312 (14) | |
C11B | 0.8614 (3) | 0.8521 (4) | 0.2695 (4) | 0.0454 (18) | |
H11B | 0.8345 | 0.8987 | 0.2663 | 0.057* | |
H12B | 0.8567 | 0.8260 | 0.3280 | 0.057* | |
C12B | 0.8154 (3) | 0.8118 (3) | 0.1726 (4) | 0.0341 (15) | |
O12B | 0.8567 (2) | 0.7685 (2) | 0.1420 (3) | 0.0357 (10) | |
O13B | 0.7376 (2) | 0.8235 (2) | 0.1287 (3) | 0.0389 (11) | |
C2B | 1.0089 (3) | 0.8071 (4) | 0.3211 (4) | 0.0410 (16) | |
H2B | 0.9905 | 0.7634 | 0.3386 | 0.051* | |
C3B | 1.0919 (3) | 0.8152 (4) | 0.3304 (5) | 0.0423 (16) | |
H3B | 1.1302 | 0.7773 | 0.3545 | 0.053* | |
C4B | 1.1176 (3) | 0.8772 (4) | 0.3050 (4) | 0.0350 (15) | |
N41B | 1.2043 (3) | 0.8842 (3) | 0.3093 (4) | 0.0472 (15) | |
O41B | 1.2527 (3) | 0.8355 (3) | 0.3447 (4) | 0.0650 (15) | |
O42B | 1.2231 (2) | 0.9400 (3) | 0.2756 (4) | 0.0590 (14) | |
C5B | 1.0652 (3) | 0.9345 (4) | 0.2751 (4) | 0.0415 (16) | |
H5B | 1.0851 | 0.9786 | 0.2611 | 0.052* | |
C6B | 0.9817 (3) | 0.9259 (4) | 0.2660 (4) | 0.0400 (16) | |
H6B | 0.9445 | 0.9648 | 0.2453 | 0.050* | |
C1C | 0.5635 (3) | 0.5901 (3) | 0.1254 (5) | 0.0394 (16) | |
C11C | 0.6544 (3) | 0.5923 (4) | 0.1405 (6) | 0.066 (2) | |
H11C | 0.6679 | 0.5478 | 0.1130 | 0.082* | |
H12C | 0.6863 | 0.5921 | 0.2148 | 0.082* | |
C12C | 0.6873 (3) | 0.6521 (3) | 0.0955 (4) | 0.0330 (15) | |
O12C | 0.7621 (2) | 0.6460 (2) | 0.1032 (3) | 0.0338 (10) | |
O13C | 0.6395 (2) | 0.7025 (2) | 0.0547 (3) | 0.0371 (10) | |
C2C | 0.5015 (3) | 0.5893 (3) | 0.0290 (5) | 0.0408 (16) | |
H2C | 0.5166 | 0.5958 | −0.0290 | 0.051* | |
C3C | 0.4183 (3) | 0.5794 (3) | 0.0158 (5) | 0.0393 (16) | |
H3C | 0.3761 | 0.5776 | −0.0502 | 0.049* | |
C4C | 0.3989 (3) | 0.5723 (3) | 0.1027 (5) | 0.0382 (16) | |
N41C | 0.3114 (3) | 0.5574 (3) | 0.0917 (5) | 0.0483 (15) | |
O41C | 0.2610 (3) | 0.5471 (3) | 0.0063 (4) | 0.0680 (16) | |
O42C | 0.2946 (3) | 0.5561 (3) | 0.1684 (4) | 0.0688 (16) | |
C5C | 0.4574 (3) | 0.5748 (4) | 0.1980 (5) | 0.0421 (16) | |
H5C | 0.4416 | 0.5699 | 0.2558 | 0.053* | |
C6C | 0.5406 (3) | 0.5847 (3) | 0.2100 (5) | 0.0397 (16) | |
H6C | 0.5821 | 0.5878 | 0.2764 | 0.050* | |
C1D | 0.5350 (3) | 0.6485 (3) | −0.2842 (4) | 0.0282 (13) | |
C11D | 0.6248 (3) | 0.6259 (3) | −0.2390 (4) | 0.0331 (15) | |
H11D | 0.6502 | 0.6287 | −0.2919 | 0.041* | |
H12D | 0.6274 | 0.5762 | −0.2167 | 0.041* | |
C12D | 0.6751 (3) | 0.6716 (3) | −0.1485 (4) | 0.0284 (14) | |
O12D | 0.7472 (2) | 0.6501 (2) | −0.0936 (3) | 0.0335 (10) | |
O13D | 0.64227 (19) | 0.7275 (2) | −0.1335 (3) | 0.0341 (10) | |
C2D | 0.5135 (3) | 0.7100 (3) | −0.3384 (4) | 0.0315 (14) | |
H2D | 0.5557 | 0.7365 | −0.3515 | 0.039* | |
C3D | 0.4329 (3) | 0.7344 (3) | −0.3742 (4) | 0.0359 (15) | |
H3D | 0.4188 | 0.7771 | −0.4118 | 0.045* | |
C4D | 0.3726 (3) | 0.6953 (3) | −0.3545 (4) | 0.0353 (15) | |
N41D | 0.2860 (3) | 0.7225 (3) | −0.3915 (4) | 0.0464 (14) | |
O41D | 0.2728 (3) | 0.7813 (3) | −0.4273 (4) | 0.0719 (16) | |
O42D | 0.2320 (3) | 0.6841 (3) | −0.3821 (4) | 0.0747 (17) | |
C5D | 0.3903 (3) | 0.6323 (3) | −0.3033 (4) | 0.0393 (16) | |
H5D | 0.3474 | 0.6054 | −0.2926 | 0.049* | |
C6D | 0.4725 (3) | 0.6090 (3) | −0.2678 (4) | 0.0363 (15) | |
H6D | 0.4864 | 0.5655 | −0.2320 | 0.045* | |
N1E | 0.9359 (2) | 0.6676 (3) | 0.0511 (3) | 0.0271 (11) | |
C2E | 0.9602 (3) | 0.6025 (3) | 0.0363 (4) | 0.0293 (14) | |
N21E | 0.9021 (2) | 0.5522 (3) | 0.0039 (4) | 0.0366 (13) | |
H21E | 0.8494 | 0.5621 | −0.0072 | 0.046* | |
H22E | 0.9165 | 0.5091 | −0.0064 | 0.046* | |
N3E | 1.0397 (2) | 0.5837 (3) | 0.0524 (3) | 0.0334 (12) | |
C4E | 1.0966 (3) | 0.6339 (3) | 0.0828 (5) | 0.0385 (16) | |
H4E | 1.1530 | 0.6221 | 0.0935 | 0.048* | |
C5E | 1.0787 (3) | 0.7025 (3) | 0.0998 (4) | 0.0393 (16) | |
H5E | 1.1208 | 0.7377 | 0.1227 | 0.049* | |
C6E | 0.9961 (3) | 0.7165 (3) | 0.0816 (4) | 0.0363 (15) | |
H6E | 0.9808 | 0.7634 | 0.0911 | 0.045* | |
N1F | 0.5507 (2) | 0.8270 (3) | −0.0538 (3) | 0.0280 (11) | |
C2F | 0.5313 (3) | 0.8931 (3) | −0.0339 (4) | 0.0308 (14) | |
N21F | 0.5929 (2) | 0.9401 (3) | 0.0040 (3) | 0.0358 (13) | |
H21F | 0.6451 | 0.9278 | 0.0156 | 0.045* | |
H22F | 0.5813 | 0.9834 | 0.0173 | 0.045* | |
N3F | 0.4528 (2) | 0.9169 (3) | −0.0500 (3) | 0.0332 (12) | |
C4F | 0.3916 (3) | 0.8703 (4) | −0.0912 (4) | 0.0366 (16) | |
H4F | 0.3358 | 0.8844 | −0.1019 | 0.046* | |
C5F | 0.4045 (3) | 0.8033 (3) | −0.1189 (4) | 0.0349 (15) | |
H5F | 0.3594 | 0.7721 | −0.1513 | 0.044* | |
C6F | 0.4866 (3) | 0.7837 (3) | −0.0971 (4) | 0.0327 (14) | |
H6F | 0.4979 | 0.7372 | −0.1139 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0208 (3) | 0.0278 (4) | 0.0385 (4) | 0.0001 (3) | 0.0128 (3) | −0.0047 (4) |
Cu2 | 0.0209 (3) | 0.0274 (5) | 0.0397 (4) | 0.0010 (3) | 0.0121 (3) | −0.0040 (4) |
C1A | 0.026 (3) | 0.026 (4) | 0.061 (4) | 0.002 (3) | 0.017 (3) | 0.015 (3) |
C11A | 0.035 (4) | 0.047 (5) | 0.100 (6) | 0.008 (3) | 0.027 (4) | 0.044 (4) |
C12A | 0.026 (3) | 0.045 (5) | 0.036 (4) | −0.002 (3) | 0.002 (3) | 0.003 (3) |
O12A | 0.030 (2) | 0.031 (3) | 0.047 (2) | 0.0008 (19) | 0.0180 (18) | 0.001 (2) |
O13A | 0.023 (2) | 0.031 (3) | 0.057 (3) | 0.0018 (18) | 0.0151 (19) | 0.003 (2) |
C2A | 0.046 (4) | 0.045 (5) | 0.043 (4) | 0.005 (3) | 0.021 (3) | 0.011 (3) |
C3A | 0.028 (3) | 0.046 (5) | 0.050 (4) | −0.003 (3) | 0.011 (3) | 0.003 (3) |
C4A | 0.031 (3) | 0.041 (5) | 0.062 (5) | 0.005 (3) | 0.023 (3) | 0.010 (4) |
N41A | 0.038 (4) | 0.101 (7) | 0.091 (6) | 0.007 (4) | 0.028 (4) | 0.011 (5) |
O41A | 0.037 (3) | 0.102 (6) | 0.145 (6) | −0.029 (3) | 0.016 (3) | 0.003 (4) |
O42A | 0.069 (4) | 0.167 (8) | 0.154 (6) | −0.010 (4) | 0.069 (4) | −0.047 (6) |
C5A | 0.055 (4) | 0.050 (5) | 0.045 (4) | 0.004 (3) | 0.023 (4) | −0.003 (4) |
C6A | 0.041 (4) | 0.040 (5) | 0.048 (4) | 0.001 (3) | 0.011 (3) | 0.004 (3) |
C1B | 0.030 (3) | 0.035 (4) | 0.031 (3) | −0.003 (3) | 0.013 (3) | −0.008 (3) |
C11B | 0.031 (3) | 0.062 (5) | 0.042 (4) | −0.005 (3) | 0.012 (3) | −0.018 (4) |
C12B | 0.028 (3) | 0.032 (4) | 0.041 (4) | −0.003 (3) | 0.012 (3) | 0.000 (3) |
O12B | 0.027 (2) | 0.038 (3) | 0.042 (2) | −0.0008 (18) | 0.0128 (18) | −0.014 (2) |
O13B | 0.031 (2) | 0.042 (3) | 0.043 (3) | 0.0006 (19) | 0.0119 (19) | −0.015 (2) |
C2B | 0.039 (3) | 0.039 (4) | 0.042 (4) | −0.010 (3) | 0.011 (3) | −0.001 (3) |
C3B | 0.031 (3) | 0.044 (5) | 0.047 (4) | 0.000 (3) | 0.009 (3) | 0.001 (3) |
C4B | 0.023 (3) | 0.038 (4) | 0.039 (4) | −0.007 (3) | 0.006 (3) | −0.006 (3) |
N41B | 0.035 (3) | 0.055 (5) | 0.047 (4) | −0.011 (3) | 0.009 (3) | −0.012 (3) |
O41B | 0.034 (3) | 0.073 (4) | 0.083 (4) | 0.012 (3) | 0.015 (2) | 0.004 (3) |
O42B | 0.046 (3) | 0.058 (4) | 0.082 (4) | −0.017 (2) | 0.033 (3) | −0.007 (3) |
C5B | 0.043 (4) | 0.037 (4) | 0.046 (4) | −0.010 (3) | 0.017 (3) | 0.002 (3) |
C6B | 0.030 (3) | 0.042 (5) | 0.044 (4) | 0.002 (3) | 0.009 (3) | −0.004 (3) |
C1C | 0.030 (3) | 0.034 (4) | 0.053 (4) | 0.003 (3) | 0.013 (3) | 0.012 (3) |
C11C | 0.035 (4) | 0.059 (6) | 0.104 (6) | 0.006 (3) | 0.024 (4) | 0.046 (5) |
C12C | 0.030 (3) | 0.034 (4) | 0.033 (4) | −0.003 (3) | 0.008 (3) | 0.000 (3) |
O12C | 0.023 (2) | 0.036 (3) | 0.043 (2) | 0.0041 (18) | 0.0119 (17) | 0.006 (2) |
O13C | 0.027 (2) | 0.035 (3) | 0.054 (3) | 0.0041 (19) | 0.0189 (18) | 0.011 (2) |
C2C | 0.039 (3) | 0.045 (5) | 0.046 (4) | −0.001 (3) | 0.025 (3) | 0.004 (3) |
C3C | 0.024 (3) | 0.048 (5) | 0.044 (4) | 0.001 (3) | 0.009 (3) | 0.004 (3) |
C4C | 0.029 (3) | 0.029 (4) | 0.057 (5) | −0.003 (3) | 0.017 (3) | 0.005 (3) |
N41C | 0.034 (3) | 0.043 (4) | 0.069 (4) | 0.004 (3) | 0.019 (3) | 0.014 (3) |
O41C | 0.035 (3) | 0.082 (4) | 0.077 (4) | −0.013 (3) | 0.009 (3) | 0.013 (3) |
O42C | 0.054 (3) | 0.089 (5) | 0.080 (4) | 0.008 (3) | 0.045 (3) | 0.021 (3) |
C5C | 0.041 (4) | 0.043 (5) | 0.046 (4) | 0.002 (3) | 0.021 (3) | 0.001 (3) |
C6C | 0.029 (3) | 0.039 (4) | 0.045 (4) | 0.004 (3) | 0.006 (3) | 0.007 (3) |
C1D | 0.029 (3) | 0.028 (4) | 0.029 (3) | −0.002 (3) | 0.012 (2) | −0.003 (3) |
C11D | 0.029 (3) | 0.039 (4) | 0.034 (3) | −0.004 (3) | 0.015 (3) | −0.006 (3) |
C12D | 0.025 (3) | 0.031 (4) | 0.032 (3) | −0.004 (3) | 0.014 (3) | −0.001 (3) |
O12D | 0.024 (2) | 0.031 (3) | 0.044 (2) | 0.0007 (17) | 0.0105 (18) | −0.009 (2) |
O13D | 0.0235 (19) | 0.036 (3) | 0.041 (2) | 0.0053 (18) | 0.0085 (17) | −0.010 (2) |
C2D | 0.026 (3) | 0.035 (4) | 0.037 (3) | −0.005 (3) | 0.016 (3) | −0.004 (3) |
C3D | 0.040 (3) | 0.031 (4) | 0.040 (4) | 0.005 (3) | 0.018 (3) | 0.005 (3) |
C4D | 0.025 (3) | 0.039 (4) | 0.042 (4) | 0.005 (3) | 0.012 (3) | 0.003 (3) |
N41D | 0.029 (3) | 0.051 (4) | 0.056 (4) | 0.010 (3) | 0.011 (3) | 0.007 (3) |
O41D | 0.043 (3) | 0.067 (4) | 0.100 (4) | 0.020 (3) | 0.020 (3) | 0.037 (4) |
O42D | 0.030 (2) | 0.062 (4) | 0.134 (5) | 0.002 (2) | 0.033 (3) | 0.005 (3) |
C5D | 0.034 (3) | 0.038 (4) | 0.050 (4) | −0.005 (3) | 0.020 (3) | 0.001 (3) |
C6D | 0.024 (3) | 0.032 (4) | 0.054 (4) | 0.002 (3) | 0.016 (3) | 0.006 (3) |
N1E | 0.021 (2) | 0.026 (3) | 0.036 (3) | −0.001 (2) | 0.011 (2) | −0.007 (2) |
C2E | 0.029 (3) | 0.027 (4) | 0.033 (4) | −0.003 (3) | 0.013 (3) | 0.006 (3) |
N21E | 0.022 (2) | 0.022 (3) | 0.070 (4) | 0.003 (2) | 0.021 (2) | −0.008 (3) |
N3E | 0.018 (2) | 0.033 (3) | 0.048 (3) | 0.006 (2) | 0.010 (2) | 0.001 (3) |
C4E | 0.022 (3) | 0.040 (4) | 0.057 (4) | 0.001 (3) | 0.019 (3) | −0.001 (3) |
C5E | 0.024 (3) | 0.038 (4) | 0.059 (4) | 0.001 (3) | 0.018 (3) | −0.007 (3) |
C6E | 0.032 (3) | 0.023 (4) | 0.052 (4) | 0.002 (3) | 0.013 (3) | −0.007 (3) |
N1F | 0.023 (2) | 0.025 (3) | 0.036 (3) | −0.002 (2) | 0.011 (2) | 0.002 (2) |
C2F | 0.028 (3) | 0.032 (4) | 0.032 (3) | 0.007 (3) | 0.010 (3) | 0.006 (3) |
N21F | 0.020 (2) | 0.027 (3) | 0.057 (3) | 0.005 (2) | 0.009 (2) | −0.006 (3) |
N3F | 0.024 (2) | 0.037 (3) | 0.042 (3) | 0.007 (2) | 0.016 (2) | −0.003 (3) |
C4F | 0.023 (3) | 0.050 (5) | 0.042 (4) | 0.001 (3) | 0.019 (3) | 0.002 (3) |
C5F | 0.024 (3) | 0.041 (4) | 0.039 (4) | −0.004 (3) | 0.012 (3) | −0.006 (3) |
C6F | 0.029 (3) | 0.025 (4) | 0.046 (4) | 0.004 (3) | 0.016 (3) | −0.003 (3) |
Cu1—O12B | 1.943 (4) | C12C—O13C | 1.255 (7) |
Cu1—O12D | 1.955 (4) | C2C—C3C | 1.382 (7) |
Cu1—O12C | 1.983 (4) | C2C—H2C | 0.9500 |
Cu1—O12A | 2.012 (4) | C3C—C4C | 1.386 (8) |
Cu1—N1E | 2.154 (4) | C3C—H3C | 0.9500 |
Cu1—Cu2 | 2.6586 (10) | C4C—C5C | 1.356 (8) |
Cu2—O13A | 1.951 (4) | C4C—N41C | 1.477 (7) |
Cu2—O13C | 1.954 (4) | N41C—O42C | 1.214 (6) |
Cu2—O13D | 1.966 (4) | N41C—O41C | 1.217 (6) |
Cu2—O13B | 1.984 (4) | C5C—C6C | 1.387 (7) |
Cu2—N1F | 2.150 (4) | C5C—H5C | 0.9500 |
C1A—C6A | 1.369 (8) | C6C—H6C | 0.9500 |
C1A—C2A | 1.382 (8) | C1D—C2D | 1.370 (8) |
C1A—C11A | 1.517 (7) | C1D—C6D | 1.392 (7) |
C11A—C12A | 1.502 (8) | C1D—C11D | 1.499 (7) |
C11A—H11A | 0.9900 | C11D—C12D | 1.526 (7) |
C11A—H12A | 0.9900 | C11D—H11D | 0.9900 |
C12A—O12A | 1.253 (7) | C11D—H12D | 0.9900 |
C12A—O13A | 1.271 (6) | C12D—O13D | 1.252 (7) |
C2A—C3A | 1.376 (7) | C12D—O12D | 1.265 (6) |
C2A—H2A | 0.9500 | C2D—C3D | 1.369 (7) |
C3A—C4A | 1.366 (8) | C2D—H2D | 0.9500 |
C3A—H3A | 0.9500 | C3D—C4D | 1.378 (7) |
C4A—C5A | 1.372 (8) | C3D—H3D | 0.9500 |
C4A—N41A | 1.470 (8) | C4D—C5D | 1.372 (8) |
N41A—O41A | 1.195 (8) | C4D—N41D | 1.476 (7) |
N41A—O42A | 1.257 (9) | N41D—O41D | 1.211 (7) |
C5A—C6A | 1.366 (7) | N41D—O42D | 1.222 (6) |
C5A—H5A | 0.9500 | C5D—C6D | 1.387 (7) |
C6A—H6A | 0.9500 | C5D—H5D | 0.9500 |
C1B—C6B | 1.367 (8) | C6D—H6D | 0.9500 |
C1B—C2B | 1.395 (8) | N1E—C6E | 1.338 (7) |
C1B—C11B | 1.505 (7) | N1E—C2E | 1.343 (7) |
C11B—C12B | 1.513 (8) | C2E—N21E | 1.335 (7) |
C11B—H11B | 0.9900 | C2E—N3E | 1.344 (6) |
C11B—H12B | 0.9900 | N21E—H21E | 0.8800 |
C12B—O12B | 1.257 (6) | N21E—H22E | 0.8800 |
C12B—O13B | 1.271 (6) | N3E—C4E | 1.319 (7) |
C2B—C3B | 1.387 (7) | C4E—C5E | 1.375 (8) |
C2B—H2B | 0.9500 | C4E—H4E | 0.9500 |
C3B—C4B | 1.349 (8) | C5E—C6E | 1.370 (7) |
C3B—H3B | 0.9500 | C5E—H5E | 0.9500 |
C4B—C5B | 1.374 (8) | C6E—H6E | 0.9500 |
C4B—N41B | 1.470 (7) | N1F—C6F | 1.329 (7) |
N41B—O41B | 1.221 (7) | N1F—C2F | 1.350 (7) |
N41B—O42B | 1.249 (7) | C2F—N21F | 1.337 (7) |
C5B—C6B | 1.398 (7) | C2F—N3F | 1.359 (6) |
C5B—H5B | 0.9500 | N21F—H21F | 0.8800 |
C6B—H6B | 0.9500 | N21F—H22F | 0.8800 |
C1C—C6C | 1.387 (8) | N3F—C4F | 1.332 (7) |
C1C—C2C | 1.389 (8) | C4F—C5F | 1.370 (8) |
C1C—C11C | 1.494 (7) | C4F—H4F | 0.9500 |
C11C—C12C | 1.504 (8) | C5F—C6F | 1.378 (7) |
C11C—H11C | 0.9900 | C5F—H5F | 0.9500 |
C11C—H12C | 0.9900 | C6F—H6F | 0.9500 |
C12C—O12C | 1.253 (6) | ||
O12B—Cu1—O12D | 169.82 (14) | C1C—C11C—H11C | 107.5 |
O12B—Cu1—O12C | 89.73 (16) | C12C—C11C—H11C | 107.5 |
O12D—Cu1—O12C | 86.24 (16) | C1C—C11C—H12C | 107.5 |
O12B—Cu1—O12A | 87.39 (16) | C12C—C11C—H12C | 107.5 |
O12D—Cu1—O12A | 93.72 (16) | H11C—C11C—H12C | 107.0 |
O12C—Cu1—O12A | 162.86 (15) | O12C—C12C—O13C | 126.0 (5) |
O12B—Cu1—N1E | 89.86 (15) | O12C—C12C—C11C | 115.0 (5) |
O12D—Cu1—N1E | 100.26 (16) | O13C—C12C—C11C | 119.0 (5) |
O12C—Cu1—N1E | 107.56 (16) | C12C—O12C—Cu1 | 122.0 (4) |
O12A—Cu1—N1E | 89.34 (16) | C12C—O13C—Cu2 | 122.9 (3) |
O12B—Cu1—Cu2 | 82.54 (11) | C3C—C2C—C1C | 121.4 (5) |
O12D—Cu1—Cu2 | 87.69 (10) | C3C—C2C—H2C | 119.3 |
O12C—Cu1—Cu2 | 83.00 (10) | C1C—C2C—H2C | 119.3 |
O12A—Cu1—Cu2 | 79.87 (10) | C2C—C3C—C4C | 117.3 (5) |
N1E—Cu1—Cu2 | 167.04 (13) | C2C—C3C—H3C | 121.4 |
O13A—Cu2—O13C | 171.28 (15) | C4C—C3C—H3C | 121.4 |
O13A—Cu2—O13D | 91.85 (17) | C5C—C4C—C3C | 123.0 (5) |
O13C—Cu2—O13D | 87.55 (17) | C5C—C4C—N41C | 118.0 (6) |
O13A—Cu2—O13B | 86.92 (16) | C3C—C4C—N41C | 118.9 (5) |
O13C—Cu2—O13B | 91.16 (17) | O42C—N41C—O41C | 124.3 (5) |
O13D—Cu2—O13B | 163.36 (14) | O42C—N41C—C4C | 118.0 (6) |
O13A—Cu2—N1F | 98.00 (16) | O41C—N41C—C4C | 117.8 (6) |
O13C—Cu2—N1F | 90.71 (16) | C4C—C5C—C6C | 119.0 (6) |
O13D—Cu2—N1F | 90.49 (15) | C4C—C5C—H5C | 120.5 |
O13B—Cu2—N1F | 106.12 (16) | C6C—C5C—H5C | 120.5 |
O13A—Cu2—Cu1 | 87.38 (11) | C1C—C6C—C5C | 120.2 (6) |
O13C—Cu2—Cu1 | 83.97 (11) | C1C—C6C—H6C | 119.9 |
O13D—Cu2—Cu1 | 78.74 (10) | C5C—C6C—H6C | 119.9 |
O13B—Cu2—Cu1 | 84.62 (11) | C2D—C1D—C6D | 118.9 (5) |
N1F—Cu2—Cu1 | 168.15 (13) | C2D—C1D—C11D | 120.5 (5) |
C6A—C1A—C2A | 119.7 (5) | C6D—C1D—C11D | 120.6 (5) |
C6A—C1A—C11A | 119.7 (6) | C1D—C11D—C12D | 112.1 (5) |
C2A—C1A—C11A | 120.6 (6) | C1D—C11D—H11D | 109.2 |
C12A—C11A—C1A | 116.2 (5) | C12D—C11D—H11D | 109.2 |
C12A—C11A—H11A | 108.2 | C1D—C11D—H12D | 109.2 |
C1A—C11A—H11A | 108.2 | C12D—C11D—H12D | 109.2 |
C12A—C11A—H12A | 108.2 | H11D—C11D—H12D | 107.9 |
C1A—C11A—H12A | 108.2 | O13D—C12D—O12D | 124.7 (5) |
H11A—C11A—H12A | 107.4 | O13D—C12D—C11D | 117.9 (5) |
O12A—C12A—O13A | 125.1 (6) | O12D—C12D—C11D | 117.4 (5) |
O12A—C12A—C11A | 120.0 (5) | C12D—O12D—Cu1 | 118.1 (4) |
O13A—C12A—C11A | 114.9 (6) | C12D—O13D—Cu2 | 127.4 (4) |
C12A—O12A—Cu1 | 125.2 (4) | C3D—C2D—C1D | 121.6 (5) |
C12A—O13A—Cu2 | 119.9 (4) | C3D—C2D—H2D | 119.2 |
C3A—C2A—C1A | 120.8 (6) | C1D—C2D—H2D | 119.2 |
C3A—C2A—H2A | 119.6 | C2D—C3D—C4D | 118.4 (6) |
C1A—C2A—H2A | 119.6 | C2D—C3D—H3D | 120.8 |
C4A—C3A—C2A | 117.3 (6) | C4D—C3D—H3D | 120.8 |
C4A—C3A—H3A | 121.4 | C5D—C4D—C3D | 122.3 (5) |
C2A—C3A—H3A | 121.4 | C5D—C4D—N41D | 119.5 (5) |
C3A—C4A—C5A | 123.3 (5) | C3D—C4D—N41D | 118.2 (6) |
C3A—C4A—N41A | 118.6 (6) | O41D—N41D—O42D | 123.9 (5) |
C5A—C4A—N41A | 118.1 (6) | O41D—N41D—C4D | 118.8 (5) |
O41A—N41A—O42A | 125.5 (7) | O42D—N41D—C4D | 117.3 (6) |
O41A—N41A—C4A | 119.4 (7) | C4D—C5D—C6D | 118.0 (5) |
O42A—N41A—C4A | 115.2 (7) | C4D—C5D—H5D | 121.0 |
C6A—C5A—C4A | 118.0 (6) | C6D—C5D—H5D | 121.0 |
C6A—C5A—H5A | 121.0 | C5D—C6D—C1D | 120.7 (6) |
C4A—C5A—H5A | 121.0 | C5D—C6D—H6D | 119.7 |
C5A—C6A—C1A | 120.7 (6) | C1D—C6D—H6D | 119.7 |
C5A—C6A—H6A | 119.6 | C6E—N1E—C2E | 116.1 (4) |
C1A—C6A—H6A | 119.6 | C6E—N1E—Cu1 | 114.6 (4) |
C6B—C1B—C2B | 118.4 (5) | C2E—N1E—Cu1 | 129.1 (4) |
C6B—C1B—C11B | 121.5 (6) | N21E—C2E—N1E | 118.3 (5) |
C2B—C1B—C11B | 120.1 (6) | N21E—C2E—N3E | 117.0 (5) |
C1B—C11B—C12B | 112.5 (5) | N1E—C2E—N3E | 124.7 (5) |
C1B—C11B—H11B | 109.1 | C2E—N21E—H21E | 120.0 |
C12B—C11B—H11B | 109.1 | C2E—N21E—H22E | 120.0 |
C1B—C11B—H12B | 109.1 | H21E—N21E—H22E | 120.0 |
C12B—C11B—H12B | 109.1 | C4E—N3E—C2E | 116.6 (5) |
H11B—C11B—H12B | 107.8 | N3E—C4E—C5E | 123.7 (5) |
O12B—C12B—O13B | 124.6 (5) | N3E—C4E—H4E | 118.2 |
O12B—C12B—C11B | 117.7 (5) | C5E—C4E—H4E | 118.2 |
O13B—C12B—C11B | 117.7 (5) | C6E—C5E—C4E | 115.5 (5) |
C12B—O12B—Cu1 | 125.9 (3) | C6E—C5E—H5E | 122.2 |
C12B—O13B—Cu2 | 120.8 (4) | C4E—C5E—H5E | 122.2 |
C3B—C2B—C1B | 120.5 (6) | N1E—C6E—C5E | 123.4 (6) |
C3B—C2B—H2B | 119.8 | N1E—C6E—H6E | 118.3 |
C1B—C2B—H2B | 119.8 | C5E—C6E—H6E | 118.3 |
C4B—C3B—C2B | 119.5 (6) | C6F—N1F—C2F | 116.3 (5) |
C4B—C3B—H3B | 120.3 | C6F—N1F—Cu2 | 117.4 (4) |
C2B—C3B—H3B | 120.3 | C2F—N1F—Cu2 | 125.9 (4) |
C3B—C4B—C5B | 122.0 (5) | N21F—C2F—N1F | 119.0 (5) |
C3B—C4B—N41B | 119.3 (6) | N21F—C2F—N3F | 115.9 (5) |
C5B—C4B—N41B | 118.7 (6) | N1F—C2F—N3F | 125.2 (5) |
O41B—N41B—O42B | 124.4 (5) | C2F—N21F—H21F | 120.0 |
O41B—N41B—C4B | 118.5 (6) | C2F—N21F—H22F | 120.0 |
O42B—N41B—C4B | 117.1 (6) | H21F—N21F—H22F | 120.0 |
C4B—C5B—C6B | 118.0 (6) | C4F—N3F—C2F | 115.3 (5) |
C4B—C5B—H5B | 121.0 | N3F—C4F—C5F | 123.8 (5) |
C6B—C5B—H5B | 121.0 | N3F—C4F—H4F | 118.1 |
C1B—C6B—C5B | 121.5 (6) | C5F—C4F—H4F | 118.1 |
C1B—C6B—H6B | 119.2 | C4F—C5F—C6F | 116.4 (5) |
C5B—C6B—H6B | 119.2 | C4F—C5F—H5F | 121.8 |
C6C—C1C—C2C | 119.0 (5) | C6F—C5F—H5F | 121.8 |
C6C—C1C—C11C | 118.9 (6) | N1F—C6F—C5F | 122.9 (6) |
C2C—C1C—C11C | 122.0 (6) | N1F—C6F—H6F | 118.6 |
C1C—C11C—C12C | 119.4 (5) | C5F—C6F—H6F | 118.6 |
O12B—Cu1—Cu2—O13A | 78.98 (17) | N1E—Cu1—O12C—C12C | −173.5 (4) |
O12D—Cu1—Cu2—O13A | −103.88 (16) | Cu2—Cu1—O12C—C12C | 14.2 (4) |
O12C—Cu1—Cu2—O13A | 169.63 (16) | O12C—C12C—O13C—Cu2 | 0.6 (8) |
O12A—Cu1—Cu2—O13A | −9.69 (16) | C11C—C12C—O13C—Cu2 | −179.5 (5) |
N1E—Cu1—Cu2—O13A | 24.4 (5) | O13A—Cu2—O13C—C12C | 0.7 (13) |
O12B—Cu1—Cu2—O13C | −99.92 (17) | O13D—Cu2—O13C—C12C | 86.9 (4) |
O12D—Cu1—Cu2—O13C | 77.22 (16) | O13B—Cu2—O13C—C12C | −76.5 (4) |
O12C—Cu1—Cu2—O13C | −9.27 (16) | N1F—Cu2—O13C—C12C | 177.3 (4) |
O12A—Cu1—Cu2—O13C | 171.41 (16) | Cu1—Cu2—O13C—C12C | 7.9 (4) |
N1E—Cu1—Cu2—O13C | −154.5 (5) | C6C—C1C—C2C—C3C | −3.7 (10) |
O12B—Cu1—Cu2—O13D | 171.39 (17) | C11C—C1C—C2C—C3C | 172.7 (6) |
O12D—Cu1—Cu2—O13D | −11.48 (16) | C1C—C2C—C3C—C4C | 1.8 (10) |
O12C—Cu1—Cu2—O13D | −97.97 (16) | C2C—C3C—C4C—C5C | 0.2 (10) |
O12A—Cu1—Cu2—O13D | 82.72 (16) | C2C—C3C—C4C—N41C | −176.4 (5) |
N1E—Cu1—Cu2—O13D | 116.8 (5) | C5C—C4C—N41C—O42C | 8.1 (9) |
O12B—Cu1—Cu2—O13B | −8.18 (17) | C3C—C4C—N41C—O42C | −175.1 (6) |
O12D—Cu1—Cu2—O13B | 168.96 (16) | C5C—C4C—N41C—O41C | −171.8 (6) |
O12C—Cu1—Cu2—O13B | 82.47 (16) | C3C—C4C—N41C—O41C | 5.0 (9) |
O12A—Cu1—Cu2—O13B | −96.84 (16) | C3C—C4C—C5C—C6C | −0.3 (10) |
N1E—Cu1—Cu2—O13B | −62.8 (5) | N41C—C4C—C5C—C6C | 176.4 (6) |
O12B—Cu1—Cu2—N1F | −163.6 (6) | C2C—C1C—C6C—C5C | 3.5 (10) |
O12D—Cu1—Cu2—N1F | 13.5 (6) | C11C—C1C—C6C—C5C | −173.0 (6) |
O12C—Cu1—Cu2—N1F | −73.0 (6) | C4C—C5C—C6C—C1C | −1.6 (9) |
O12A—Cu1—Cu2—N1F | 107.7 (6) | C2D—C1D—C11D—C12D | 71.7 (7) |
N1E—Cu1—Cu2—N1F | 141.8 (8) | C6D—C1D—C11D—C12D | −105.5 (6) |
C6A—C1A—C11A—C12A | 103.4 (7) | C1D—C11D—C12D—O13D | −11.9 (7) |
C2A—C1A—C11A—C12A | −79.8 (9) | C1D—C11D—C12D—O12D | 167.8 (5) |
C1A—C11A—C12A—O12A | −14.3 (10) | O13D—C12D—O12D—Cu1 | 1.3 (7) |
C1A—C11A—C12A—O13A | 163.9 (6) | C11D—C12D—O12D—Cu1 | −178.4 (3) |
O13A—C12A—O12A—Cu1 | −17.1 (8) | O12B—Cu1—O12D—C12D | 25.6 (12) |
C11A—C12A—O12A—Cu1 | 160.9 (5) | O12C—Cu1—O12D—C12D | 92.5 (4) |
O12B—Cu1—O12A—C12A | −66.4 (4) | O12A—Cu1—O12D—C12D | −70.4 (4) |
O12D—Cu1—O12A—C12A | 103.4 (4) | N1E—Cu1—O12D—C12D | −160.4 (4) |
O12C—Cu1—O12A—C12A | 14.1 (8) | Cu2—Cu1—O12D—C12D | 9.3 (4) |
N1E—Cu1—O12A—C12A | −156.3 (4) | O12D—C12D—O13D—Cu2 | −18.4 (8) |
Cu2—Cu1—O12A—C12A | 16.4 (4) | C11D—C12D—O13D—Cu2 | 161.3 (4) |
O12A—C12A—O13A—Cu2 | 3.0 (8) | O13A—Cu2—O13D—C12D | 105.8 (4) |
C11A—C12A—O13A—Cu2 | −175.1 (4) | O13C—Cu2—O13D—C12D | −65.5 (4) |
O13C—Cu2—O13A—C12A | 14.5 (13) | O13B—Cu2—O13D—C12D | 20.4 (9) |
O13D—Cu2—O13A—C12A | −71.4 (4) | N1F—Cu2—O13D—C12D | −156.2 (4) |
O13B—Cu2—O13A—C12A | 92.0 (4) | Cu1—Cu2—O13D—C12D | 18.8 (4) |
N1F—Cu2—O13A—C12A | −162.2 (4) | C6D—C1D—C2D—C3D | 1.9 (8) |
Cu1—Cu2—O13A—C12A | 7.2 (4) | C11D—C1D—C2D—C3D | −175.3 (5) |
C6A—C1A—C2A—C3A | 3.9 (10) | C1D—C2D—C3D—C4D | 0.0 (8) |
C11A—C1A—C2A—C3A | −172.9 (6) | C2D—C3D—C4D—C5D | −2.1 (9) |
C1A—C2A—C3A—C4A | −2.6 (10) | C2D—C3D—C4D—N41D | 178.8 (5) |
C2A—C3A—C4A—C5A | −1.1 (10) | C5D—C4D—N41D—O41D | 172.6 (6) |
C2A—C3A—C4A—N41A | 177.5 (6) | C3D—C4D—N41D—O41D | −8.3 (9) |
C3A—C4A—N41A—O41A | −27.8 (11) | C5D—C4D—N41D—O42D | −6.0 (9) |
C5A—C4A—N41A—O41A | 151.0 (7) | C3D—C4D—N41D—O42D | 173.1 (6) |
C3A—C4A—N41A—O42A | 151.2 (8) | C3D—C4D—C5D—C6D | 2.2 (9) |
C5A—C4A—N41A—O42A | −30.1 (10) | N41D—C4D—C5D—C6D | −178.8 (5) |
C3A—C4A—C5A—C6A | 3.6 (11) | C4D—C5D—C6D—C1D | −0.2 (9) |
N41A—C4A—C5A—C6A | −175.1 (6) | C2D—C1D—C6D—C5D | −1.8 (9) |
C4A—C5A—C6A—C1A | −2.3 (10) | C11D—C1D—C6D—C5D | 175.4 (5) |
C2A—C1A—C6A—C5A | −1.3 (10) | O12B—Cu1—N1E—C6E | −38.3 (4) |
C11A—C1A—C6A—C5A | 175.5 (6) | O12D—Cu1—N1E—C6E | 142.8 (4) |
C6B—C1B—C11B—C12B | 102.0 (7) | O12C—Cu1—N1E—C6E | −127.9 (4) |
C2B—C1B—C11B—C12B | −76.5 (7) | O12A—Cu1—N1E—C6E | 49.1 (4) |
C1B—C11B—C12B—O12B | 29.0 (8) | Cu2—Cu1—N1E—C6E | 15.6 (8) |
C1B—C11B—C12B—O13B | −152.0 (5) | O12B—Cu1—N1E—C2E | 145.5 (5) |
O13B—C12B—O12B—Cu1 | −2.6 (9) | O12D—Cu1—N1E—C2E | −33.5 (5) |
C11B—C12B—O12B—Cu1 | 176.3 (4) | O12C—Cu1—N1E—C2E | 55.8 (5) |
O12D—Cu1—O12B—C12B | −7.9 (13) | O12A—Cu1—N1E—C2E | −127.1 (5) |
O12C—Cu1—O12B—C12B | −74.4 (5) | Cu2—Cu1—N1E—C2E | −160.6 (4) |
O12A—Cu1—O12B—C12B | 88.6 (5) | C6E—N1E—C2E—N21E | −178.7 (5) |
N1E—Cu1—O12B—C12B | 178.0 (5) | Cu1—N1E—C2E—N21E | −2.5 (8) |
Cu2—Cu1—O12B—C12B | 8.5 (5) | C6E—N1E—C2E—N3E | 1.8 (8) |
O12B—C12B—O13B—Cu2 | −8.8 (8) | Cu1—N1E—C2E—N3E | 178.0 (4) |
C11B—C12B—O13B—Cu2 | 172.3 (4) | N21E—C2E—N3E—C4E | 178.9 (5) |
O13A—Cu2—O13B—C12B | −76.5 (4) | N1E—C2E—N3E—C4E | −1.5 (8) |
O13C—Cu2—O13B—C12B | 94.9 (4) | C2E—N3E—C4E—C5E | 1.1 (9) |
O13D—Cu2—O13B—C12B | 9.6 (9) | N3E—C4E—C5E—C6E | −0.9 (9) |
N1F—Cu2—O13B—C12B | −174.0 (4) | C2E—N1E—C6E—C5E | −1.6 (8) |
Cu1—Cu2—O13B—C12B | 11.1 (4) | Cu1—N1E—C6E—C5E | −178.4 (4) |
C6B—C1B—C2B—C3B | −2.8 (9) | C4E—C5E—C6E—N1E | 1.2 (9) |
C11B—C1B—C2B—C3B | 175.7 (5) | O13A—Cu2—N1F—C6F | 133.5 (4) |
C1B—C2B—C3B—C4B | −0.3 (9) | O13C—Cu2—N1F—C6F | −46.0 (4) |
C2B—C3B—C4B—C5B | 3.6 (9) | O13D—Cu2—N1F—C6F | 41.6 (4) |
C2B—C3B—C4B—N41B | −176.4 (5) | O13B—Cu2—N1F—C6F | −137.4 (4) |
C3B—C4B—N41B—O41B | −6.6 (8) | Cu1—Cu2—N1F—C6F | 17.1 (9) |
C5B—C4B—N41B—O41B | 173.3 (6) | O13A—Cu2—N1F—C2F | −53.7 (5) |
C3B—C4B—N41B—O42B | 173.1 (6) | O13C—Cu2—N1F—C2F | 126.9 (5) |
C5B—C4B—N41B—O42B | −7.0 (8) | O13D—Cu2—N1F—C2F | −145.6 (4) |
C3B—C4B—C5B—C6B | −3.5 (9) | O13B—Cu2—N1F—C2F | 35.4 (5) |
N41B—C4B—C5B—C6B | 176.5 (5) | Cu1—Cu2—N1F—C2F | −170.1 (4) |
C2B—C1B—C6B—C5B | 2.9 (9) | C6F—N1F—C2F—N21F | −176.0 (5) |
C11B—C1B—C6B—C5B | −175.7 (5) | Cu2—N1F—C2F—N21F | 11.1 (7) |
C4B—C5B—C6B—C1B | 0.2 (9) | C6F—N1F—C2F—N3F | 3.5 (8) |
C6C—C1C—C11C—C12C | −125.8 (7) | Cu2—N1F—C2F—N3F | −169.4 (4) |
C2C—C1C—C11C—C12C | 57.8 (10) | N21F—C2F—N3F—C4F | 177.7 (5) |
C1C—C11C—C12C—O12C | −173.2 (6) | N1F—C2F—N3F—C4F | −1.8 (8) |
C1C—C11C—C12C—O13C | 6.9 (10) | C2F—N3F—C4F—C5F | −1.8 (8) |
O13C—C12C—O12C—Cu1 | −13.5 (8) | N3F—C4F—C5F—C6F | 3.3 (9) |
C11C—C12C—O12C—Cu1 | 166.6 (5) | C2F—N1F—C6F—C5F | −1.7 (8) |
O12B—Cu1—O12C—C12C | 96.7 (4) | Cu2—N1F—C6F—C5F | 171.8 (4) |
O12D—Cu1—O12C—C12C | −73.9 (4) | C4F—C5F—C6F—N1F | −1.5 (8) |
O12A—Cu1—O12C—C12C | 16.5 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21E—H21E···O12D | 0.88 | 2.41 | 3.121 (6) | 139 |
N21E—H22E···N3Ei | 0.88 | 2.10 | 2.971 (7) | 168 |
N21F—H21F···O13A | 0.88 | 2.47 | 3.190 (6) | 139 |
N21F—H22F···N3Fii | 0.88 | 2.08 | 2.958 (7) | 176 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C4H5N3)2(C8H6NO4)4] |
Mr | 1037.85 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 17.134 (5), 18.9575 (8), 14.0859 (6) |
β (°) | 111.159 (3) |
V (Å3) | 4266.9 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.08 |
Crystal size (mm) | 0.50 × 0.10 × 0.02 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.613, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21389, 9074, 3921 |
Rint | 0.127 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.149, 0.92 |
No. of reflections | 9074 |
No. of parameters | 613 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −0.54 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N21E—H21E···O12D | 0.88 | 2.41 | 3.121 (6) | 138.6 |
N21E—H22E···N3Ei | 0.88 | 2.10 | 2.971 (7) | 168.2 |
N21F—H21F···O13A | 0.88 | 2.47 | 3.190 (6) | 139.2 |
N21F—H22F···N3Fii | 0.88 | 2.08 | 2.958 (7) | 176.4 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z. |
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Complexes of the copper(II) acetate monohydrate type prepared with the addition of 2-aminopyrimidine are expected to produce arrays of alternating tetra(carboxylato-O,O')bis[copper(II)] and 2-aminopyrimidine units linked by axial Cu—N bonds (Smith et al., 1996). However, the structure of the title compound, (I). comprises individual units of tetra(carboxylato-O,O')-bis[copper(II)] end-capped with two 2-aminopyrimidine molecules, which form a hydrogen-bonded polymer chain via the pyrimidines. The hydrogen-bonding goemetry is listed in Table 1. The eight Cu—O distances are in the range 1.943 (4) Å to 2.012 (4) Å, with an average of 1.969 (4) Å, while the two Cu—N distances are 2.154 (4) and 2.150 (4) Å. The hydrogen-bonding patterns in these types of molecules usually consist of associations from the two amino protons to two adjacent carboxylate O atoms. This is the case in (I) for the two inwardly facing NH's but the two outward amino protons bind to an adjacent outward pyrimidine N, thus forming pyrimidine dimers. With like binding to like (i.e. E—E and F—F) the structure forms an hydrogen-bonded polymer with individual groups of alternating direction. All structures of the copper(II) acetate type made with 2-aminopyrimidine have the potential to exhibit packing similar to (I), but this is the first reported example.