The structure of the title compound, [Cu
2(C
8H
6NO
4)
4(C
4H
5N
3)
2], comprises individual units of tetra-μ-carboxylato-
O:
O′-dicopper(II) end-capped with two 2-aminopyrimidine molecules. These pyrimidines then form dimers across a typical N—H
N association, thus producing linear hydrogen-bonded polymer chains.
Supporting information
CCDC reference: 159982
Complex (I) was prepared as per the literature procedure (Smith et al.,
1996).
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.
'Bis(µ-2-aminopyrimidine-N
1) tetrakis[µ-(4-nitrophenyl)acetato-O:
O']
dicopper(II)'
top
Crystal data top
[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 | |
Data collection top
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 top
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 |
Crystal data top
[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)° | |
Data collection top
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 | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
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.