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The structure of the title compound, [Cu2(C8H6NO4)4(C4H5N3)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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100017455/de1163sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100017455/de1163Isup2.hkl
Contains datablock I

CCDC reference: 159982

Comment top

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.

Related literature top

For related literature, see: Smith et al. (1996).

Experimental top

Complex (I) was prepared as per the literature procedure (Smith et al., 1996).

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom-numbering scheme showing 30% probability ellipsoids.
'Bis(µ-2-aminopyrimidine-N1) tetrakis[µ-(4-nitrophenyl)acetato-O:O'] dicopper(II)' top
Crystal data top
[Cu2(C4H5N3)2(C8H6NO4)4]Dx = 1.616 Mg m3
Mr = 1037.85Melting point: 465-467 K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.134 (5) ÅCell parameters from 8113 reflections
b = 18.9575 (8) Åθ = 2.9–27.5°
c = 14.0859 (6) ŵ = 1.08 mm1
β = 111.159 (3)°T = 150 K
V = 4266.9 (13) Å3Plate, green
Z = 40.50 × 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 anode3921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.127
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 2121
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 2424
Tmin = 0.613, Tmax = 0.979l = 1818
21389 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H 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 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
[Cu2(C4H5N3)2(C8H6NO4)4]V = 4266.9 (13) Å3
Mr = 1037.85Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.134 (5) ŵ = 1.08 mm1
b = 18.9575 (8) ÅT = 150 K
c = 14.0859 (6) Å0.50 × 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 = 0.979Rint = 0.127
21389 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.51 e Å3
9074 reflectionsΔρmin = 0.54 e Å3
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
xyzUiso*/Ueq
Cu10.81174 (3)0.70652 (4)0.02487 (5)0.0285 (2)
Cu20.67440 (3)0.78285 (4)0.00720 (5)0.0290 (2)
C1A0.9219 (3)0.8986 (3)0.1005 (5)0.0375 (16)
C11A0.8309 (3)0.9052 (4)0.1115 (6)0.060 (2)
H11A0.82510.94730.07300.075*
H12A0.79720.91380.18420.075*
C12A0.7940 (3)0.8432 (4)0.0763 (4)0.0385 (16)
O12A0.8316 (2)0.7852 (2)0.0596 (3)0.0347 (10)
O13A0.7257 (2)0.8558 (2)0.0632 (3)0.0371 (10)
C2A0.9851 (4)0.9100 (3)0.0075 (5)0.0433 (17)
H2A0.97140.91680.05150.054*
C3A1.0676 (3)0.9115 (4)0.0008 (5)0.0421 (17)
H3A1.11120.92120.06390.053*
C4A1.0842 (3)0.8985 (4)0.0854 (5)0.0430 (17)
N41A1.1714 (4)0.9027 (4)0.0800 (6)0.075 (2)
O41A1.2194 (3)0.9406 (4)0.0186 (5)0.099 (2)
O42A1.1889 (3)0.8638 (4)0.1418 (5)0.122 (3)
C5A1.0234 (4)0.8831 (4)0.1776 (5)0.0485 (18)
H5A1.03750.87180.23510.061*
C6A0.9418 (4)0.8846 (3)0.1844 (5)0.0445 (17)
H6A0.89840.87580.24800.056*
C1B0.9525 (3)0.8627 (3)0.2863 (4)0.0312 (14)
C11B0.8614 (3)0.8521 (4)0.2695 (4)0.0454 (18)
H11B0.83450.89870.26630.057*
H12B0.85670.82600.32800.057*
C12B0.8154 (3)0.8118 (3)0.1726 (4)0.0341 (15)
O12B0.8567 (2)0.7685 (2)0.1420 (3)0.0357 (10)
O13B0.7376 (2)0.8235 (2)0.1287 (3)0.0389 (11)
C2B1.0089 (3)0.8071 (4)0.3211 (4)0.0410 (16)
H2B0.99050.76340.33860.051*
C3B1.0919 (3)0.8152 (4)0.3304 (5)0.0423 (16)
H3B1.13020.77730.35450.053*
C4B1.1176 (3)0.8772 (4)0.3050 (4)0.0350 (15)
N41B1.2043 (3)0.8842 (3)0.3093 (4)0.0472 (15)
O41B1.2527 (3)0.8355 (3)0.3447 (4)0.0650 (15)
O42B1.2231 (2)0.9400 (3)0.2756 (4)0.0590 (14)
C5B1.0652 (3)0.9345 (4)0.2751 (4)0.0415 (16)
H5B1.08510.97860.26110.052*
C6B0.9817 (3)0.9259 (4)0.2660 (4)0.0400 (16)
H6B0.94450.96480.24530.050*
C1C0.5635 (3)0.5901 (3)0.1254 (5)0.0394 (16)
C11C0.6544 (3)0.5923 (4)0.1405 (6)0.066 (2)
H11C0.66790.54780.11300.082*
H12C0.68630.59210.21480.082*
C12C0.6873 (3)0.6521 (3)0.0955 (4)0.0330 (15)
O12C0.7621 (2)0.6460 (2)0.1032 (3)0.0338 (10)
O13C0.6395 (2)0.7025 (2)0.0547 (3)0.0371 (10)
C2C0.5015 (3)0.5893 (3)0.0290 (5)0.0408 (16)
H2C0.51660.59580.02900.051*
C3C0.4183 (3)0.5794 (3)0.0158 (5)0.0393 (16)
H3C0.37610.57760.05020.049*
C4C0.3989 (3)0.5723 (3)0.1027 (5)0.0382 (16)
N41C0.3114 (3)0.5574 (3)0.0917 (5)0.0483 (15)
O41C0.2610 (3)0.5471 (3)0.0063 (4)0.0680 (16)
O42C0.2946 (3)0.5561 (3)0.1684 (4)0.0688 (16)
C5C0.4574 (3)0.5748 (4)0.1980 (5)0.0421 (16)
H5C0.44160.56990.25580.053*
C6C0.5406 (3)0.5847 (3)0.2100 (5)0.0397 (16)
H6C0.58210.58780.27640.050*
C1D0.5350 (3)0.6485 (3)0.2842 (4)0.0282 (13)
C11D0.6248 (3)0.6259 (3)0.2390 (4)0.0331 (15)
H11D0.65020.62870.29190.041*
H12D0.62740.57620.21670.041*
C12D0.6751 (3)0.6716 (3)0.1485 (4)0.0284 (14)
O12D0.7472 (2)0.6501 (2)0.0936 (3)0.0335 (10)
O13D0.64227 (19)0.7275 (2)0.1335 (3)0.0341 (10)
C2D0.5135 (3)0.7100 (3)0.3384 (4)0.0315 (14)
H2D0.55570.73650.35150.039*
C3D0.4329 (3)0.7344 (3)0.3742 (4)0.0359 (15)
H3D0.41880.77710.41180.045*
C4D0.3726 (3)0.6953 (3)0.3545 (4)0.0353 (15)
N41D0.2860 (3)0.7225 (3)0.3915 (4)0.0464 (14)
O41D0.2728 (3)0.7813 (3)0.4273 (4)0.0719 (16)
O42D0.2320 (3)0.6841 (3)0.3821 (4)0.0747 (17)
C5D0.3903 (3)0.6323 (3)0.3033 (4)0.0393 (16)
H5D0.34740.60540.29260.049*
C6D0.4725 (3)0.6090 (3)0.2678 (4)0.0363 (15)
H6D0.48640.56550.23200.045*
N1E0.9359 (2)0.6676 (3)0.0511 (3)0.0271 (11)
C2E0.9602 (3)0.6025 (3)0.0363 (4)0.0293 (14)
N21E0.9021 (2)0.5522 (3)0.0039 (4)0.0366 (13)
H21E0.84940.56210.00720.046*
H22E0.91650.50910.00640.046*
N3E1.0397 (2)0.5837 (3)0.0524 (3)0.0334 (12)
C4E1.0966 (3)0.6339 (3)0.0828 (5)0.0385 (16)
H4E1.15300.62210.09350.048*
C5E1.0787 (3)0.7025 (3)0.0998 (4)0.0393 (16)
H5E1.12080.73770.12270.049*
C6E0.9961 (3)0.7165 (3)0.0816 (4)0.0363 (15)
H6E0.98080.76340.09110.045*
N1F0.5507 (2)0.8270 (3)0.0538 (3)0.0280 (11)
C2F0.5313 (3)0.8931 (3)0.0339 (4)0.0308 (14)
N21F0.5929 (2)0.9401 (3)0.0040 (3)0.0358 (13)
H21F0.64510.92780.01560.045*
H22F0.58130.98340.01730.045*
N3F0.4528 (2)0.9169 (3)0.0500 (3)0.0332 (12)
C4F0.3916 (3)0.8703 (4)0.0912 (4)0.0366 (16)
H4F0.33580.88440.10190.046*
C5F0.4045 (3)0.8033 (3)0.1189 (4)0.0349 (15)
H5F0.35940.77210.15130.044*
C6F0.4866 (3)0.7837 (3)0.0971 (4)0.0327 (14)
H6F0.49790.73720.11390.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0208 (3)0.0278 (4)0.0385 (4)0.0001 (3)0.0128 (3)0.0047 (4)
Cu20.0209 (3)0.0274 (5)0.0397 (4)0.0010 (3)0.0121 (3)0.0040 (4)
C1A0.026 (3)0.026 (4)0.061 (4)0.002 (3)0.017 (3)0.015 (3)
C11A0.035 (4)0.047 (5)0.100 (6)0.008 (3)0.027 (4)0.044 (4)
C12A0.026 (3)0.045 (5)0.036 (4)0.002 (3)0.002 (3)0.003 (3)
O12A0.030 (2)0.031 (3)0.047 (2)0.0008 (19)0.0180 (18)0.001 (2)
O13A0.023 (2)0.031 (3)0.057 (3)0.0018 (18)0.0151 (19)0.003 (2)
C2A0.046 (4)0.045 (5)0.043 (4)0.005 (3)0.021 (3)0.011 (3)
C3A0.028 (3)0.046 (5)0.050 (4)0.003 (3)0.011 (3)0.003 (3)
C4A0.031 (3)0.041 (5)0.062 (5)0.005 (3)0.023 (3)0.010 (4)
N41A0.038 (4)0.101 (7)0.091 (6)0.007 (4)0.028 (4)0.011 (5)
O41A0.037 (3)0.102 (6)0.145 (6)0.029 (3)0.016 (3)0.003 (4)
O42A0.069 (4)0.167 (8)0.154 (6)0.010 (4)0.069 (4)0.047 (6)
C5A0.055 (4)0.050 (5)0.045 (4)0.004 (3)0.023 (4)0.003 (4)
C6A0.041 (4)0.040 (5)0.048 (4)0.001 (3)0.011 (3)0.004 (3)
C1B0.030 (3)0.035 (4)0.031 (3)0.003 (3)0.013 (3)0.008 (3)
C11B0.031 (3)0.062 (5)0.042 (4)0.005 (3)0.012 (3)0.018 (4)
C12B0.028 (3)0.032 (4)0.041 (4)0.003 (3)0.012 (3)0.000 (3)
O12B0.027 (2)0.038 (3)0.042 (2)0.0008 (18)0.0128 (18)0.014 (2)
O13B0.031 (2)0.042 (3)0.043 (3)0.0006 (19)0.0119 (19)0.015 (2)
C2B0.039 (3)0.039 (4)0.042 (4)0.010 (3)0.011 (3)0.001 (3)
C3B0.031 (3)0.044 (5)0.047 (4)0.000 (3)0.009 (3)0.001 (3)
C4B0.023 (3)0.038 (4)0.039 (4)0.007 (3)0.006 (3)0.006 (3)
N41B0.035 (3)0.055 (5)0.047 (4)0.011 (3)0.009 (3)0.012 (3)
O41B0.034 (3)0.073 (4)0.083 (4)0.012 (3)0.015 (2)0.004 (3)
O42B0.046 (3)0.058 (4)0.082 (4)0.017 (2)0.033 (3)0.007 (3)
C5B0.043 (4)0.037 (4)0.046 (4)0.010 (3)0.017 (3)0.002 (3)
C6B0.030 (3)0.042 (5)0.044 (4)0.002 (3)0.009 (3)0.004 (3)
C1C0.030 (3)0.034 (4)0.053 (4)0.003 (3)0.013 (3)0.012 (3)
C11C0.035 (4)0.059 (6)0.104 (6)0.006 (3)0.024 (4)0.046 (5)
C12C0.030 (3)0.034 (4)0.033 (4)0.003 (3)0.008 (3)0.000 (3)
O12C0.023 (2)0.036 (3)0.043 (2)0.0041 (18)0.0119 (17)0.006 (2)
O13C0.027 (2)0.035 (3)0.054 (3)0.0041 (19)0.0189 (18)0.011 (2)
C2C0.039 (3)0.045 (5)0.046 (4)0.001 (3)0.025 (3)0.004 (3)
C3C0.024 (3)0.048 (5)0.044 (4)0.001 (3)0.009 (3)0.004 (3)
C4C0.029 (3)0.029 (4)0.057 (5)0.003 (3)0.017 (3)0.005 (3)
N41C0.034 (3)0.043 (4)0.069 (4)0.004 (3)0.019 (3)0.014 (3)
O41C0.035 (3)0.082 (4)0.077 (4)0.013 (3)0.009 (3)0.013 (3)
O42C0.054 (3)0.089 (5)0.080 (4)0.008 (3)0.045 (3)0.021 (3)
C5C0.041 (4)0.043 (5)0.046 (4)0.002 (3)0.021 (3)0.001 (3)
C6C0.029 (3)0.039 (4)0.045 (4)0.004 (3)0.006 (3)0.007 (3)
C1D0.029 (3)0.028 (4)0.029 (3)0.002 (3)0.012 (2)0.003 (3)
C11D0.029 (3)0.039 (4)0.034 (3)0.004 (3)0.015 (3)0.006 (3)
C12D0.025 (3)0.031 (4)0.032 (3)0.004 (3)0.014 (3)0.001 (3)
O12D0.024 (2)0.031 (3)0.044 (2)0.0007 (17)0.0105 (18)0.009 (2)
O13D0.0235 (19)0.036 (3)0.041 (2)0.0053 (18)0.0085 (17)0.010 (2)
C2D0.026 (3)0.035 (4)0.037 (3)0.005 (3)0.016 (3)0.004 (3)
C3D0.040 (3)0.031 (4)0.040 (4)0.005 (3)0.018 (3)0.005 (3)
C4D0.025 (3)0.039 (4)0.042 (4)0.005 (3)0.012 (3)0.003 (3)
N41D0.029 (3)0.051 (4)0.056 (4)0.010 (3)0.011 (3)0.007 (3)
O41D0.043 (3)0.067 (4)0.100 (4)0.020 (3)0.020 (3)0.037 (4)
O42D0.030 (2)0.062 (4)0.134 (5)0.002 (2)0.033 (3)0.005 (3)
C5D0.034 (3)0.038 (4)0.050 (4)0.005 (3)0.020 (3)0.001 (3)
C6D0.024 (3)0.032 (4)0.054 (4)0.002 (3)0.016 (3)0.006 (3)
N1E0.021 (2)0.026 (3)0.036 (3)0.001 (2)0.011 (2)0.007 (2)
C2E0.029 (3)0.027 (4)0.033 (4)0.003 (3)0.013 (3)0.006 (3)
N21E0.022 (2)0.022 (3)0.070 (4)0.003 (2)0.021 (2)0.008 (3)
N3E0.018 (2)0.033 (3)0.048 (3)0.006 (2)0.010 (2)0.001 (3)
C4E0.022 (3)0.040 (4)0.057 (4)0.001 (3)0.019 (3)0.001 (3)
C5E0.024 (3)0.038 (4)0.059 (4)0.001 (3)0.018 (3)0.007 (3)
C6E0.032 (3)0.023 (4)0.052 (4)0.002 (3)0.013 (3)0.007 (3)
N1F0.023 (2)0.025 (3)0.036 (3)0.002 (2)0.011 (2)0.002 (2)
C2F0.028 (3)0.032 (4)0.032 (3)0.007 (3)0.010 (3)0.006 (3)
N21F0.020 (2)0.027 (3)0.057 (3)0.005 (2)0.009 (2)0.006 (3)
N3F0.024 (2)0.037 (3)0.042 (3)0.007 (2)0.016 (2)0.003 (3)
C4F0.023 (3)0.050 (5)0.042 (4)0.001 (3)0.019 (3)0.002 (3)
C5F0.024 (3)0.041 (4)0.039 (4)0.004 (3)0.012 (3)0.006 (3)
C6F0.029 (3)0.025 (4)0.046 (4)0.004 (3)0.016 (3)0.003 (3)
Geometric parameters (Å, º) top
Cu1—O12B1.943 (4)C12C—O13C1.255 (7)
Cu1—O12D1.955 (4)C2C—C3C1.382 (7)
Cu1—O12C1.983 (4)C2C—H2C0.9500
Cu1—O12A2.012 (4)C3C—C4C1.386 (8)
Cu1—N1E2.154 (4)C3C—H3C0.9500
Cu1—Cu22.6586 (10)C4C—C5C1.356 (8)
Cu2—O13A1.951 (4)C4C—N41C1.477 (7)
Cu2—O13C1.954 (4)N41C—O42C1.214 (6)
Cu2—O13D1.966 (4)N41C—O41C1.217 (6)
Cu2—O13B1.984 (4)C5C—C6C1.387 (7)
Cu2—N1F2.150 (4)C5C—H5C0.9500
C1A—C6A1.369 (8)C6C—H6C0.9500
C1A—C2A1.382 (8)C1D—C2D1.370 (8)
C1A—C11A1.517 (7)C1D—C6D1.392 (7)
C11A—C12A1.502 (8)C1D—C11D1.499 (7)
C11A—H11A0.9900C11D—C12D1.526 (7)
C11A—H12A0.9900C11D—H11D0.9900
C12A—O12A1.253 (7)C11D—H12D0.9900
C12A—O13A1.271 (6)C12D—O13D1.252 (7)
C2A—C3A1.376 (7)C12D—O12D1.265 (6)
C2A—H2A0.9500C2D—C3D1.369 (7)
C3A—C4A1.366 (8)C2D—H2D0.9500
C3A—H3A0.9500C3D—C4D1.378 (7)
C4A—C5A1.372 (8)C3D—H3D0.9500
C4A—N41A1.470 (8)C4D—C5D1.372 (8)
N41A—O41A1.195 (8)C4D—N41D1.476 (7)
N41A—O42A1.257 (9)N41D—O41D1.211 (7)
C5A—C6A1.366 (7)N41D—O42D1.222 (6)
C5A—H5A0.9500C5D—C6D1.387 (7)
C6A—H6A0.9500C5D—H5D0.9500
C1B—C6B1.367 (8)C6D—H6D0.9500
C1B—C2B1.395 (8)N1E—C6E1.338 (7)
C1B—C11B1.505 (7)N1E—C2E1.343 (7)
C11B—C12B1.513 (8)C2E—N21E1.335 (7)
C11B—H11B0.9900C2E—N3E1.344 (6)
C11B—H12B0.9900N21E—H21E0.8800
C12B—O12B1.257 (6)N21E—H22E0.8800
C12B—O13B1.271 (6)N3E—C4E1.319 (7)
C2B—C3B1.387 (7)C4E—C5E1.375 (8)
C2B—H2B0.9500C4E—H4E0.9500
C3B—C4B1.349 (8)C5E—C6E1.370 (7)
C3B—H3B0.9500C5E—H5E0.9500
C4B—C5B1.374 (8)C6E—H6E0.9500
C4B—N41B1.470 (7)N1F—C6F1.329 (7)
N41B—O41B1.221 (7)N1F—C2F1.350 (7)
N41B—O42B1.249 (7)C2F—N21F1.337 (7)
C5B—C6B1.398 (7)C2F—N3F1.359 (6)
C5B—H5B0.9500N21F—H21F0.8800
C6B—H6B0.9500N21F—H22F0.8800
C1C—C6C1.387 (8)N3F—C4F1.332 (7)
C1C—C2C1.389 (8)C4F—C5F1.370 (8)
C1C—C11C1.494 (7)C4F—H4F0.9500
C11C—C12C1.504 (8)C5F—C6F1.378 (7)
C11C—H11C0.9900C5F—H5F0.9500
C11C—H12C0.9900C6F—H6F0.9500
C12C—O12C1.253 (6)
O12B—Cu1—O12D169.82 (14)C1C—C11C—H11C107.5
O12B—Cu1—O12C89.73 (16)C12C—C11C—H11C107.5
O12D—Cu1—O12C86.24 (16)C1C—C11C—H12C107.5
O12B—Cu1—O12A87.39 (16)C12C—C11C—H12C107.5
O12D—Cu1—O12A93.72 (16)H11C—C11C—H12C107.0
O12C—Cu1—O12A162.86 (15)O12C—C12C—O13C126.0 (5)
O12B—Cu1—N1E89.86 (15)O12C—C12C—C11C115.0 (5)
O12D—Cu1—N1E100.26 (16)O13C—C12C—C11C119.0 (5)
O12C—Cu1—N1E107.56 (16)C12C—O12C—Cu1122.0 (4)
O12A—Cu1—N1E89.34 (16)C12C—O13C—Cu2122.9 (3)
O12B—Cu1—Cu282.54 (11)C3C—C2C—C1C121.4 (5)
O12D—Cu1—Cu287.69 (10)C3C—C2C—H2C119.3
O12C—Cu1—Cu283.00 (10)C1C—C2C—H2C119.3
O12A—Cu1—Cu279.87 (10)C2C—C3C—C4C117.3 (5)
N1E—Cu1—Cu2167.04 (13)C2C—C3C—H3C121.4
O13A—Cu2—O13C171.28 (15)C4C—C3C—H3C121.4
O13A—Cu2—O13D91.85 (17)C5C—C4C—C3C123.0 (5)
O13C—Cu2—O13D87.55 (17)C5C—C4C—N41C118.0 (6)
O13A—Cu2—O13B86.92 (16)C3C—C4C—N41C118.9 (5)
O13C—Cu2—O13B91.16 (17)O42C—N41C—O41C124.3 (5)
O13D—Cu2—O13B163.36 (14)O42C—N41C—C4C118.0 (6)
O13A—Cu2—N1F98.00 (16)O41C—N41C—C4C117.8 (6)
O13C—Cu2—N1F90.71 (16)C4C—C5C—C6C119.0 (6)
O13D—Cu2—N1F90.49 (15)C4C—C5C—H5C120.5
O13B—Cu2—N1F106.12 (16)C6C—C5C—H5C120.5
O13A—Cu2—Cu187.38 (11)C1C—C6C—C5C120.2 (6)
O13C—Cu2—Cu183.97 (11)C1C—C6C—H6C119.9
O13D—Cu2—Cu178.74 (10)C5C—C6C—H6C119.9
O13B—Cu2—Cu184.62 (11)C2D—C1D—C6D118.9 (5)
N1F—Cu2—Cu1168.15 (13)C2D—C1D—C11D120.5 (5)
C6A—C1A—C2A119.7 (5)C6D—C1D—C11D120.6 (5)
C6A—C1A—C11A119.7 (6)C1D—C11D—C12D112.1 (5)
C2A—C1A—C11A120.6 (6)C1D—C11D—H11D109.2
C12A—C11A—C1A116.2 (5)C12D—C11D—H11D109.2
C12A—C11A—H11A108.2C1D—C11D—H12D109.2
C1A—C11A—H11A108.2C12D—C11D—H12D109.2
C12A—C11A—H12A108.2H11D—C11D—H12D107.9
C1A—C11A—H12A108.2O13D—C12D—O12D124.7 (5)
H11A—C11A—H12A107.4O13D—C12D—C11D117.9 (5)
O12A—C12A—O13A125.1 (6)O12D—C12D—C11D117.4 (5)
O12A—C12A—C11A120.0 (5)C12D—O12D—Cu1118.1 (4)
O13A—C12A—C11A114.9 (6)C12D—O13D—Cu2127.4 (4)
C12A—O12A—Cu1125.2 (4)C3D—C2D—C1D121.6 (5)
C12A—O13A—Cu2119.9 (4)C3D—C2D—H2D119.2
C3A—C2A—C1A120.8 (6)C1D—C2D—H2D119.2
C3A—C2A—H2A119.6C2D—C3D—C4D118.4 (6)
C1A—C2A—H2A119.6C2D—C3D—H3D120.8
C4A—C3A—C2A117.3 (6)C4D—C3D—H3D120.8
C4A—C3A—H3A121.4C5D—C4D—C3D122.3 (5)
C2A—C3A—H3A121.4C5D—C4D—N41D119.5 (5)
C3A—C4A—C5A123.3 (5)C3D—C4D—N41D118.2 (6)
C3A—C4A—N41A118.6 (6)O41D—N41D—O42D123.9 (5)
C5A—C4A—N41A118.1 (6)O41D—N41D—C4D118.8 (5)
O41A—N41A—O42A125.5 (7)O42D—N41D—C4D117.3 (6)
O41A—N41A—C4A119.4 (7)C4D—C5D—C6D118.0 (5)
O42A—N41A—C4A115.2 (7)C4D—C5D—H5D121.0
C6A—C5A—C4A118.0 (6)C6D—C5D—H5D121.0
C6A—C5A—H5A121.0C5D—C6D—C1D120.7 (6)
C4A—C5A—H5A121.0C5D—C6D—H6D119.7
C5A—C6A—C1A120.7 (6)C1D—C6D—H6D119.7
C5A—C6A—H6A119.6C6E—N1E—C2E116.1 (4)
C1A—C6A—H6A119.6C6E—N1E—Cu1114.6 (4)
C6B—C1B—C2B118.4 (5)C2E—N1E—Cu1129.1 (4)
C6B—C1B—C11B121.5 (6)N21E—C2E—N1E118.3 (5)
C2B—C1B—C11B120.1 (6)N21E—C2E—N3E117.0 (5)
C1B—C11B—C12B112.5 (5)N1E—C2E—N3E124.7 (5)
C1B—C11B—H11B109.1C2E—N21E—H21E120.0
C12B—C11B—H11B109.1C2E—N21E—H22E120.0
C1B—C11B—H12B109.1H21E—N21E—H22E120.0
C12B—C11B—H12B109.1C4E—N3E—C2E116.6 (5)
H11B—C11B—H12B107.8N3E—C4E—C5E123.7 (5)
O12B—C12B—O13B124.6 (5)N3E—C4E—H4E118.2
O12B—C12B—C11B117.7 (5)C5E—C4E—H4E118.2
O13B—C12B—C11B117.7 (5)C6E—C5E—C4E115.5 (5)
C12B—O12B—Cu1125.9 (3)C6E—C5E—H5E122.2
C12B—O13B—Cu2120.8 (4)C4E—C5E—H5E122.2
C3B—C2B—C1B120.5 (6)N1E—C6E—C5E123.4 (6)
C3B—C2B—H2B119.8N1E—C6E—H6E118.3
C1B—C2B—H2B119.8C5E—C6E—H6E118.3
C4B—C3B—C2B119.5 (6)C6F—N1F—C2F116.3 (5)
C4B—C3B—H3B120.3C6F—N1F—Cu2117.4 (4)
C2B—C3B—H3B120.3C2F—N1F—Cu2125.9 (4)
C3B—C4B—C5B122.0 (5)N21F—C2F—N1F119.0 (5)
C3B—C4B—N41B119.3 (6)N21F—C2F—N3F115.9 (5)
C5B—C4B—N41B118.7 (6)N1F—C2F—N3F125.2 (5)
O41B—N41B—O42B124.4 (5)C2F—N21F—H21F120.0
O41B—N41B—C4B118.5 (6)C2F—N21F—H22F120.0
O42B—N41B—C4B117.1 (6)H21F—N21F—H22F120.0
C4B—C5B—C6B118.0 (6)C4F—N3F—C2F115.3 (5)
C4B—C5B—H5B121.0N3F—C4F—C5F123.8 (5)
C6B—C5B—H5B121.0N3F—C4F—H4F118.1
C1B—C6B—C5B121.5 (6)C5F—C4F—H4F118.1
C1B—C6B—H6B119.2C4F—C5F—C6F116.4 (5)
C5B—C6B—H6B119.2C4F—C5F—H5F121.8
C6C—C1C—C2C119.0 (5)C6F—C5F—H5F121.8
C6C—C1C—C11C118.9 (6)N1F—C6F—C5F122.9 (6)
C2C—C1C—C11C122.0 (6)N1F—C6F—H6F118.6
C1C—C11C—C12C119.4 (5)C5F—C6F—H6F118.6
O12B—Cu1—Cu2—O13A78.98 (17)N1E—Cu1—O12C—C12C173.5 (4)
O12D—Cu1—Cu2—O13A103.88 (16)Cu2—Cu1—O12C—C12C14.2 (4)
O12C—Cu1—Cu2—O13A169.63 (16)O12C—C12C—O13C—Cu20.6 (8)
O12A—Cu1—Cu2—O13A9.69 (16)C11C—C12C—O13C—Cu2179.5 (5)
N1E—Cu1—Cu2—O13A24.4 (5)O13A—Cu2—O13C—C12C0.7 (13)
O12B—Cu1—Cu2—O13C99.92 (17)O13D—Cu2—O13C—C12C86.9 (4)
O12D—Cu1—Cu2—O13C77.22 (16)O13B—Cu2—O13C—C12C76.5 (4)
O12C—Cu1—Cu2—O13C9.27 (16)N1F—Cu2—O13C—C12C177.3 (4)
O12A—Cu1—Cu2—O13C171.41 (16)Cu1—Cu2—O13C—C12C7.9 (4)
N1E—Cu1—Cu2—O13C154.5 (5)C6C—C1C—C2C—C3C3.7 (10)
O12B—Cu1—Cu2—O13D171.39 (17)C11C—C1C—C2C—C3C172.7 (6)
O12D—Cu1—Cu2—O13D11.48 (16)C1C—C2C—C3C—C4C1.8 (10)
O12C—Cu1—Cu2—O13D97.97 (16)C2C—C3C—C4C—C5C0.2 (10)
O12A—Cu1—Cu2—O13D82.72 (16)C2C—C3C—C4C—N41C176.4 (5)
N1E—Cu1—Cu2—O13D116.8 (5)C5C—C4C—N41C—O42C8.1 (9)
O12B—Cu1—Cu2—O13B8.18 (17)C3C—C4C—N41C—O42C175.1 (6)
O12D—Cu1—Cu2—O13B168.96 (16)C5C—C4C—N41C—O41C171.8 (6)
O12C—Cu1—Cu2—O13B82.47 (16)C3C—C4C—N41C—O41C5.0 (9)
O12A—Cu1—Cu2—O13B96.84 (16)C3C—C4C—C5C—C6C0.3 (10)
N1E—Cu1—Cu2—O13B62.8 (5)N41C—C4C—C5C—C6C176.4 (6)
O12B—Cu1—Cu2—N1F163.6 (6)C2C—C1C—C6C—C5C3.5 (10)
O12D—Cu1—Cu2—N1F13.5 (6)C11C—C1C—C6C—C5C173.0 (6)
O12C—Cu1—Cu2—N1F73.0 (6)C4C—C5C—C6C—C1C1.6 (9)
O12A—Cu1—Cu2—N1F107.7 (6)C2D—C1D—C11D—C12D71.7 (7)
N1E—Cu1—Cu2—N1F141.8 (8)C6D—C1D—C11D—C12D105.5 (6)
C6A—C1A—C11A—C12A103.4 (7)C1D—C11D—C12D—O13D11.9 (7)
C2A—C1A—C11A—C12A79.8 (9)C1D—C11D—C12D—O12D167.8 (5)
C1A—C11A—C12A—O12A14.3 (10)O13D—C12D—O12D—Cu11.3 (7)
C1A—C11A—C12A—O13A163.9 (6)C11D—C12D—O12D—Cu1178.4 (3)
O13A—C12A—O12A—Cu117.1 (8)O12B—Cu1—O12D—C12D25.6 (12)
C11A—C12A—O12A—Cu1160.9 (5)O12C—Cu1—O12D—C12D92.5 (4)
O12B—Cu1—O12A—C12A66.4 (4)O12A—Cu1—O12D—C12D70.4 (4)
O12D—Cu1—O12A—C12A103.4 (4)N1E—Cu1—O12D—C12D160.4 (4)
O12C—Cu1—O12A—C12A14.1 (8)Cu2—Cu1—O12D—C12D9.3 (4)
N1E—Cu1—O12A—C12A156.3 (4)O12D—C12D—O13D—Cu218.4 (8)
Cu2—Cu1—O12A—C12A16.4 (4)C11D—C12D—O13D—Cu2161.3 (4)
O12A—C12A—O13A—Cu23.0 (8)O13A—Cu2—O13D—C12D105.8 (4)
C11A—C12A—O13A—Cu2175.1 (4)O13C—Cu2—O13D—C12D65.5 (4)
O13C—Cu2—O13A—C12A14.5 (13)O13B—Cu2—O13D—C12D20.4 (9)
O13D—Cu2—O13A—C12A71.4 (4)N1F—Cu2—O13D—C12D156.2 (4)
O13B—Cu2—O13A—C12A92.0 (4)Cu1—Cu2—O13D—C12D18.8 (4)
N1F—Cu2—O13A—C12A162.2 (4)C6D—C1D—C2D—C3D1.9 (8)
Cu1—Cu2—O13A—C12A7.2 (4)C11D—C1D—C2D—C3D175.3 (5)
C6A—C1A—C2A—C3A3.9 (10)C1D—C2D—C3D—C4D0.0 (8)
C11A—C1A—C2A—C3A172.9 (6)C2D—C3D—C4D—C5D2.1 (9)
C1A—C2A—C3A—C4A2.6 (10)C2D—C3D—C4D—N41D178.8 (5)
C2A—C3A—C4A—C5A1.1 (10)C5D—C4D—N41D—O41D172.6 (6)
C2A—C3A—C4A—N41A177.5 (6)C3D—C4D—N41D—O41D8.3 (9)
C3A—C4A—N41A—O41A27.8 (11)C5D—C4D—N41D—O42D6.0 (9)
C5A—C4A—N41A—O41A151.0 (7)C3D—C4D—N41D—O42D173.1 (6)
C3A—C4A—N41A—O42A151.2 (8)C3D—C4D—C5D—C6D2.2 (9)
C5A—C4A—N41A—O42A30.1 (10)N41D—C4D—C5D—C6D178.8 (5)
C3A—C4A—C5A—C6A3.6 (11)C4D—C5D—C6D—C1D0.2 (9)
N41A—C4A—C5A—C6A175.1 (6)C2D—C1D—C6D—C5D1.8 (9)
C4A—C5A—C6A—C1A2.3 (10)C11D—C1D—C6D—C5D175.4 (5)
C2A—C1A—C6A—C5A1.3 (10)O12B—Cu1—N1E—C6E38.3 (4)
C11A—C1A—C6A—C5A175.5 (6)O12D—Cu1—N1E—C6E142.8 (4)
C6B—C1B—C11B—C12B102.0 (7)O12C—Cu1—N1E—C6E127.9 (4)
C2B—C1B—C11B—C12B76.5 (7)O12A—Cu1—N1E—C6E49.1 (4)
C1B—C11B—C12B—O12B29.0 (8)Cu2—Cu1—N1E—C6E15.6 (8)
C1B—C11B—C12B—O13B152.0 (5)O12B—Cu1—N1E—C2E145.5 (5)
O13B—C12B—O12B—Cu12.6 (9)O12D—Cu1—N1E—C2E33.5 (5)
C11B—C12B—O12B—Cu1176.3 (4)O12C—Cu1—N1E—C2E55.8 (5)
O12D—Cu1—O12B—C12B7.9 (13)O12A—Cu1—N1E—C2E127.1 (5)
O12C—Cu1—O12B—C12B74.4 (5)Cu2—Cu1—N1E—C2E160.6 (4)
O12A—Cu1—O12B—C12B88.6 (5)C6E—N1E—C2E—N21E178.7 (5)
N1E—Cu1—O12B—C12B178.0 (5)Cu1—N1E—C2E—N21E2.5 (8)
Cu2—Cu1—O12B—C12B8.5 (5)C6E—N1E—C2E—N3E1.8 (8)
O12B—C12B—O13B—Cu28.8 (8)Cu1—N1E—C2E—N3E178.0 (4)
C11B—C12B—O13B—Cu2172.3 (4)N21E—C2E—N3E—C4E178.9 (5)
O13A—Cu2—O13B—C12B76.5 (4)N1E—C2E—N3E—C4E1.5 (8)
O13C—Cu2—O13B—C12B94.9 (4)C2E—N3E—C4E—C5E1.1 (9)
O13D—Cu2—O13B—C12B9.6 (9)N3E—C4E—C5E—C6E0.9 (9)
N1F—Cu2—O13B—C12B174.0 (4)C2E—N1E—C6E—C5E1.6 (8)
Cu1—Cu2—O13B—C12B11.1 (4)Cu1—N1E—C6E—C5E178.4 (4)
C6B—C1B—C2B—C3B2.8 (9)C4E—C5E—C6E—N1E1.2 (9)
C11B—C1B—C2B—C3B175.7 (5)O13A—Cu2—N1F—C6F133.5 (4)
C1B—C2B—C3B—C4B0.3 (9)O13C—Cu2—N1F—C6F46.0 (4)
C2B—C3B—C4B—C5B3.6 (9)O13D—Cu2—N1F—C6F41.6 (4)
C2B—C3B—C4B—N41B176.4 (5)O13B—Cu2—N1F—C6F137.4 (4)
C3B—C4B—N41B—O41B6.6 (8)Cu1—Cu2—N1F—C6F17.1 (9)
C5B—C4B—N41B—O41B173.3 (6)O13A—Cu2—N1F—C2F53.7 (5)
C3B—C4B—N41B—O42B173.1 (6)O13C—Cu2—N1F—C2F126.9 (5)
C5B—C4B—N41B—O42B7.0 (8)O13D—Cu2—N1F—C2F145.6 (4)
C3B—C4B—C5B—C6B3.5 (9)O13B—Cu2—N1F—C2F35.4 (5)
N41B—C4B—C5B—C6B176.5 (5)Cu1—Cu2—N1F—C2F170.1 (4)
C2B—C1B—C6B—C5B2.9 (9)C6F—N1F—C2F—N21F176.0 (5)
C11B—C1B—C6B—C5B175.7 (5)Cu2—N1F—C2F—N21F11.1 (7)
C4B—C5B—C6B—C1B0.2 (9)C6F—N1F—C2F—N3F3.5 (8)
C6C—C1C—C11C—C12C125.8 (7)Cu2—N1F—C2F—N3F169.4 (4)
C2C—C1C—C11C—C12C57.8 (10)N21F—C2F—N3F—C4F177.7 (5)
C1C—C11C—C12C—O12C173.2 (6)N1F—C2F—N3F—C4F1.8 (8)
C1C—C11C—C12C—O13C6.9 (10)C2F—N3F—C4F—C5F1.8 (8)
O13C—C12C—O12C—Cu113.5 (8)N3F—C4F—C5F—C6F3.3 (9)
C11C—C12C—O12C—Cu1166.6 (5)C2F—N1F—C6F—C5F1.7 (8)
O12B—Cu1—O12C—C12C96.7 (4)Cu2—N1F—C6F—C5F171.8 (4)
O12D—Cu1—O12C—C12C73.9 (4)C4F—C5F—C6F—N1F1.5 (8)
O12A—Cu1—O12C—C12C16.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21E—H21E···O12D0.882.413.121 (6)139
N21E—H22E···N3Ei0.882.102.971 (7)168
N21F—H21F···O13A0.882.473.190 (6)139
N21F—H22F···N3Fii0.882.082.958 (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]
Mr1037.85
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)17.134 (5), 18.9575 (8), 14.0859 (6)
β (°) 111.159 (3)
V3)4266.9 (13)
Z4
Radiation typeMo Kα
µ (mm1)1.08
Crystal size (mm)0.50 × 0.10 × 0.02
Data collection
DiffractometerEnraf Nonius KappaCCD area detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.613, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
21389, 9074, 3921
Rint0.127
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.149, 0.92
No. of reflections9074
No. of parameters613
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21E—H21E···O12D0.882.413.121 (6)138.6
N21E—H22E···N3Ei0.882.102.971 (7)168.2
N21F—H21F···O13A0.882.473.190 (6)139.2
N21F—H22F···N3Fii0.882.082.958 (7)176.4
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+2, z.
 

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