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In the structure of the title compound, (NH4)8[Cu4(C2O4)8(H2O)2]·4H2O, isolated tetramers of [Cu(ox)2]2+ (ox is oxalate) are present. Each CuII ion coordinates to four O atoms in two oxalate ligands and to two more distant O atoms in a neighbouring oxalate ligand or a water molecule. An extensive hydrogen-bonding network connects the tetramers to two unique solvent water molecules and four ammonium ions.
Supporting information
CCDC reference: 608521
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.061
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu2 - O17 .. 14.03 su
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - C3 .. 5.06 su
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.55 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C4 ... 1.55 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C5 - C6 ... 1.54 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C8 ... 1.56 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22 .. O16 .. 2.63 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
O8 -CU1 -O1 -C1 58.10 1.60 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6
O5 -CU1 -O4 -C2 140.30 1.90 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9
O4 -CU1 -O5 -C3 39.00 2.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10
O1 -CU1 -O8 -C4 124.70 1.50 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14
O16 -CU2 -O9 -C5 106.30 0.90 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18
O13 -CU2 -O12 -C6 -84.40 0.80 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19
O12 -CU2 -O13 -C7 -106.50 0.80 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23
O9 -CU2 -O16 -C8 78.20 0.90 1.555 1.555 1.555 1.555
PLAT732_ALERT_1_C Angle Calc 104(4), Rep 103.5(17) ...... 2.35 su-Rat
H191 -O19 -H192 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6
H2 O
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C16 H44 Cu4 N8 O38
Atom count from _chemical_formula_moiety:C16 H52 Cu4 O38
ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.630 0.790
Tmin and Tmax expected: 0.603 0.898
RR = 1.186
Please check that your absorption correction is appropriate.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
10 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003) and SHELXL97.
Octaammonium diaquahexa-µ
2-oxalato-dioxalatotetracopper(II) tetrahydrate
top
Crystal data top
(NH4)8[Cu4(C2O4)8(H2O)2]·4H2O | F(000) = 1232 |
Mr = 1210.76 | Dx = 1.944 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 44987 reflections |
a = 11.1364 (6) Å | θ = 1.0–33.4° |
b = 11.2806 (6) Å | µ = 2.16 mm−1 |
c = 17.1470 (12) Å | T = 293 K |
β = 106.235 (5)° | Plate, light_blue |
V = 2068.2 (2) Å3 | 0.50 × 0.20 × 0.05 mm |
Z = 2 | |
Data collection top
Oxford Xcalibur-3 κ- diffractometer with Sapphire-III CCD detector | 6003 independent reflections |
Radiation source: fine-focus sealed tube | 2994 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
Detector resolution: 12 pixels mm-1 | θmax = 30.0°, θmin = 3.8° |
ω scans at different φ | h = −15→15 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | k = −15→15 |
Tmin = 0.63, Tmax = 0.79 | l = −24→24 |
37577 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)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.061 | Only H-atom coordinates refined |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0199P)2] where P = (Fo2 + 2Fc2)/3 |
6003 reflections | (Δ/σ)max = 0.001 |
366 parameters | Δρmax = 0.40 e Å−3 |
49 restraints | Δρmin = −0.36 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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.40803 (3) | 0.41798 (3) | 0.41453 (2) | 0.02631 (10) | |
Cu2 | 0.07726 (3) | 0.37175 (3) | 0.35794 (2) | 0.02753 (10) | |
O1 | 0.43841 (16) | 0.26045 (15) | 0.38414 (10) | 0.0292 (4) | |
O2 | 0.41019 (18) | 0.07420 (17) | 0.41938 (11) | 0.0374 (5) | |
O3 | 0.28188 (16) | 0.16242 (15) | 0.52262 (11) | 0.0336 (5) | |
O4 | 0.31815 (15) | 0.34460 (16) | 0.48334 (10) | 0.0267 (4) | |
O5 | 0.49268 (16) | 0.49588 (16) | 0.34431 (10) | 0.0296 (5) | |
O6 | 0.51588 (16) | 0.67863 (16) | 0.30121 (11) | 0.0349 (5) | |
O7 | 0.41022 (16) | 0.76258 (15) | 0.41640 (10) | 0.0288 (4) | |
O8 | 0.38175 (15) | 0.57528 (15) | 0.45030 (10) | 0.0255 (4) | |
O9 | 0.11539 (15) | 0.21517 (15) | 0.32515 (10) | 0.0269 (4) | |
O10 | 0.07831 (16) | 0.02648 (16) | 0.35055 (11) | 0.0325 (5) | |
O11 | −0.05758 (16) | 0.10621 (16) | 0.45064 (11) | 0.0339 (5) | |
O12 | −0.00105 (15) | 0.29047 (16) | 0.42988 (10) | 0.0281 (4) | |
O13 | 0.17223 (16) | 0.45002 (16) | 0.29365 (10) | 0.0279 (4) | |
O14 | 0.20329 (16) | 0.63328 (16) | 0.25489 (11) | 0.0339 (5) | |
O15 | 0.08867 (16) | 0.71733 (17) | 0.36737 (12) | 0.0380 (5) | |
O16 | 0.05399 (16) | 0.52916 (15) | 0.39616 (10) | 0.0282 (4) | |
C1 | 0.3978 (2) | 0.1807 (3) | 0.42437 (16) | 0.0239 (6) | |
C2 | 0.3260 (2) | 0.2312 (2) | 0.48273 (15) | 0.0228 (6) | |
C3 | 0.4811 (2) | 0.6090 (2) | 0.34496 (16) | 0.0240 (6) | |
C4 | 0.4184 (2) | 0.6553 (3) | 0.40898 (16) | 0.0216 (6) | |
C5 | 0.0694 (2) | 0.1333 (3) | 0.36031 (15) | 0.0211 (6) | |
C6 | −0.0041 (2) | 0.1783 (3) | 0.41861 (15) | 0.0237 (6) | |
C7 | 0.1627 (2) | 0.5634 (3) | 0.29584 (16) | 0.0238 (6) | |
C8 | 0.0957 (2) | 0.6102 (3) | 0.35851 (16) | 0.0255 (7) | |
O17 | −0.1406 (2) | 0.38073 (18) | 0.25935 (12) | 0.0414 (6) | |
H171 | −0.142 (3) | 0.3242 (15) | 0.2384 (16) | 0.062* | |
H172 | −0.131 (3) | 0.4251 (19) | 0.2295 (15) | 0.062* | |
N1 | 0.11360 (19) | 0.36813 (19) | 0.12100 (13) | 0.0319 (6) | |
H11 | 0.0578 (15) | 0.3114 (14) | 0.1168 (12) | 0.048* | |
H12 | 0.0788 (17) | 0.4298 (12) | 0.0939 (11) | 0.048* | |
H13 | 0.1471 (17) | 0.3848 (17) | 0.1719 (6) | 0.048* | |
H14 | 0.1714 (15) | 0.3415 (17) | 0.0992 (11) | 0.048* | |
O18 | 0.23648 (19) | 1.1407 (2) | 0.20398 (12) | 0.0480 (6) | |
H181 | 0.214 (3) | 1.148 (3) | 0.2395 (14) | 0.072* | |
H182 | 0.3029 (16) | 1.157 (3) | 0.2166 (18) | 0.072* | |
N2 | 0.2001 (2) | 0.9684 (2) | 0.07376 (14) | 0.0419 (7) | |
H21 | 0.1333 (13) | 0.9505 (19) | 0.0365 (10) | 0.063* | |
H22 | 0.185 (2) | 1.0101 (17) | 0.1130 (10) | 0.063* | |
H23 | 0.2422 (18) | 0.9049 (13) | 0.0942 (12) | 0.063* | |
H24 | 0.2491 (17) | 1.0119 (17) | 0.0527 (12) | 0.063* | |
O19 | 0.31953 (19) | 0.7411 (2) | 0.13825 (14) | 0.0494 (6) | |
H191 | 0.3872 (14) | 0.734 (3) | 0.1467 (19) | 0.074* | |
H192 | 0.303 (3) | 0.702 (3) | 0.1683 (18) | 0.074* | |
N3 | 0.5835 (2) | 0.42278 (19) | 0.21013 (13) | 0.0369 (6) | |
H31 | 0.5661 (19) | 0.4744 (15) | 0.1699 (10) | 0.055* | |
H32 | 0.5538 (19) | 0.4488 (18) | 0.2484 (10) | 0.055* | |
H33 | 0.6656 (9) | 0.4164 (19) | 0.2282 (12) | 0.055* | |
H34 | 0.5521 (18) | 0.3545 (11) | 0.1920 (12) | 0.055* | |
N4 | 0.2672 (2) | 0.59639 (19) | −0.01195 (14) | 0.0376 (6) | |
H41 | 0.1925 (11) | 0.5846 (18) | −0.0438 (11) | 0.056* | |
H42 | 0.263 (2) | 0.6267 (18) | 0.0341 (8) | 0.056* | |
H43 | 0.3095 (17) | 0.5313 (12) | −0.0036 (12) | 0.056* | |
H44 | 0.3052 (18) | 0.6487 (15) | −0.0352 (12) | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.03291 (19) | 0.0217 (2) | 0.0301 (2) | −0.00016 (16) | 0.01826 (16) | 0.00014 (16) |
Cu2 | 0.0356 (2) | 0.0214 (2) | 0.0313 (2) | −0.00111 (16) | 0.01861 (16) | −0.00058 (16) |
O1 | 0.0395 (11) | 0.0217 (11) | 0.0345 (11) | −0.0001 (9) | 0.0235 (9) | −0.0011 (9) |
O2 | 0.0577 (13) | 0.0178 (12) | 0.0454 (13) | 0.0017 (11) | 0.0284 (10) | −0.0013 (10) |
O3 | 0.0423 (11) | 0.0272 (12) | 0.0406 (12) | −0.0050 (9) | 0.0267 (10) | 0.0037 (10) |
O4 | 0.0319 (11) | 0.0209 (12) | 0.0326 (11) | −0.0009 (8) | 0.0176 (9) | −0.0020 (9) |
O5 | 0.0440 (12) | 0.0192 (11) | 0.0349 (12) | 0.0017 (9) | 0.0265 (10) | 0.0003 (9) |
O6 | 0.0454 (12) | 0.0282 (12) | 0.0405 (12) | 0.0034 (9) | 0.0275 (10) | 0.0124 (10) |
O7 | 0.0400 (11) | 0.0173 (12) | 0.0338 (12) | 0.0033 (9) | 0.0183 (9) | 0.0001 (9) |
O8 | 0.0338 (10) | 0.0197 (11) | 0.0283 (11) | 0.0012 (9) | 0.0172 (9) | 0.0020 (9) |
O9 | 0.0334 (10) | 0.0215 (11) | 0.0310 (11) | −0.0017 (8) | 0.0174 (9) | 0.0003 (9) |
O10 | 0.0387 (11) | 0.0183 (12) | 0.0451 (13) | −0.0011 (9) | 0.0192 (10) | −0.0037 (10) |
O11 | 0.0422 (12) | 0.0275 (12) | 0.0393 (12) | −0.0044 (9) | 0.0235 (10) | 0.0035 (9) |
O12 | 0.0374 (11) | 0.0220 (11) | 0.0312 (11) | 0.0027 (9) | 0.0198 (9) | 0.0012 (9) |
O13 | 0.0344 (11) | 0.0222 (11) | 0.0323 (11) | −0.0017 (9) | 0.0181 (9) | 0.0000 (9) |
O14 | 0.0404 (11) | 0.0301 (12) | 0.0339 (12) | −0.0029 (10) | 0.0151 (10) | 0.0078 (10) |
O15 | 0.0448 (12) | 0.0203 (12) | 0.0544 (14) | 0.0007 (10) | 0.0230 (11) | −0.0037 (10) |
O16 | 0.0358 (11) | 0.0224 (11) | 0.0319 (12) | −0.0007 (9) | 0.0186 (9) | −0.0003 (9) |
C1 | 0.0251 (15) | 0.0231 (18) | 0.0243 (16) | −0.0021 (13) | 0.0084 (13) | −0.0025 (14) |
C2 | 0.0222 (15) | 0.0249 (19) | 0.0225 (15) | −0.0028 (13) | 0.0079 (12) | −0.0011 (13) |
C3 | 0.0215 (14) | 0.0261 (19) | 0.0243 (16) | 0.0027 (12) | 0.0062 (12) | 0.0013 (13) |
C4 | 0.0189 (14) | 0.0210 (17) | 0.0233 (16) | 0.0015 (12) | 0.0029 (12) | 0.0000 (13) |
C5 | 0.0180 (13) | 0.0254 (18) | 0.0191 (14) | 0.0002 (13) | 0.0041 (11) | 0.0010 (14) |
C6 | 0.0257 (15) | 0.0234 (18) | 0.0213 (16) | 0.0031 (13) | 0.0055 (12) | 0.0034 (13) |
C7 | 0.0199 (14) | 0.0259 (18) | 0.0229 (16) | −0.0017 (13) | 0.0018 (12) | 0.0025 (14) |
C8 | 0.0198 (15) | 0.027 (2) | 0.0266 (16) | 0.0011 (13) | 0.0020 (12) | −0.0012 (14) |
O17 | 0.0618 (14) | 0.0262 (12) | 0.0388 (13) | −0.0047 (13) | 0.0185 (12) | −0.0007 (10) |
N1 | 0.0355 (13) | 0.0307 (14) | 0.0336 (14) | 0.0070 (11) | 0.0164 (11) | 0.0016 (12) |
O18 | 0.0420 (13) | 0.0593 (16) | 0.0491 (15) | −0.0021 (13) | 0.0234 (11) | −0.0075 (13) |
N2 | 0.0379 (15) | 0.0567 (18) | 0.0352 (15) | −0.0056 (13) | 0.0172 (13) | 0.0038 (13) |
O19 | 0.0382 (12) | 0.0708 (18) | 0.0418 (15) | −0.0038 (13) | 0.0156 (11) | 0.0005 (12) |
N3 | 0.0547 (16) | 0.0268 (14) | 0.0361 (15) | −0.0026 (13) | 0.0242 (13) | −0.0041 (12) |
N4 | 0.0417 (15) | 0.0297 (15) | 0.0483 (17) | −0.0014 (12) | 0.0240 (13) | −0.0035 (13) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9085 (17) | O16—C8 | 1.279 (3) |
Cu1—O8 | 1.9262 (17) | C1—C2 | 1.554 (3) |
Cu1—O4 | 1.9338 (17) | C3—C4 | 1.547 (3) |
Cu1—O5 | 1.9353 (17) | C5—C6 | 1.545 (3) |
Cu1—O8i | 2.7971 (17) | C7—C8 | 1.562 (4) |
Cu1—O13 | 2.8779 (18) | O17—H171 | 0.730 (14) |
Cu2—O12 | 1.9300 (17) | O17—H172 | 0.744 (15) |
Cu2—O16 | 1.9348 (17) | N1—H11 | 0.880 (9) |
Cu2—O9 | 1.9365 (17) | N1—H12 | 0.866 (9) |
Cu2—O13 | 1.9403 (17) | N1—H13 | 0.868 (9) |
Cu2—O17 | 2.542 (2) | N1—H14 | 0.882 (10) |
Cu2—O4 | 2.9481 (17) | O18—H181 | 0.725 (15) |
O1—C1 | 1.290 (3) | O18—H182 | 0.733 (15) |
O2—C1 | 1.215 (3) | N2—H21 | 0.858 (10) |
O3—C2 | 1.224 (3) | N2—H22 | 0.877 (10) |
O4—C2 | 1.283 (3) | N2—H23 | 0.874 (10) |
O5—C3 | 1.284 (3) | N2—H24 | 0.882 (10) |
O6—C3 | 1.221 (3) | O19—H191 | 0.731 (15) |
O7—C4 | 1.223 (3) | O19—H192 | 0.739 (15) |
O8—C4 | 1.283 (3) | N3—H31 | 0.882 (10) |
O9—C5 | 1.285 (3) | N3—H32 | 0.865 (10) |
O10—C5 | 1.225 (3) | N3—H33 | 0.882 (10) |
O11—C6 | 1.225 (3) | N3—H34 | 0.867 (10) |
O12—C6 | 1.278 (3) | N4—H41 | 0.868 (9) |
O13—C7 | 1.285 (3) | N4—H42 | 0.874 (10) |
O14—C7 | 1.223 (3) | N4—H43 | 0.863 (10) |
O15—C8 | 1.223 (3) | N4—H44 | 0.883 (10) |
| | | |
O1—Cu1—O8 | 177.34 (8) | O11—C6—C5 | 118.9 (2) |
O1—Cu1—O4 | 85.96 (7) | O12—C6—C5 | 115.2 (2) |
O8—Cu1—O4 | 92.83 (7) | O14—C7—O13 | 125.3 (2) |
O1—Cu1—O5 | 95.65 (7) | O14—C7—C8 | 120.1 (3) |
O8—Cu1—O5 | 85.62 (7) | O13—C7—C8 | 114.6 (2) |
O4—Cu1—O5 | 177.74 (8) | O15—C8—O16 | 126.8 (3) |
O12—Cu2—O16 | 95.29 (7) | O15—C8—C7 | 118.6 (3) |
O12—Cu2—O9 | 85.82 (7) | O16—C8—C7 | 114.6 (2) |
O16—Cu2—O9 | 175.08 (7) | H171—O17—H172 | 103.5 (17) |
O12—Cu2—O13 | 174.14 (7) | H11—N1—H12 | 109.9 (12) |
O16—Cu2—O13 | 85.46 (7) | H11—N1—H13 | 109.5 (12) |
O9—Cu2—O13 | 92.95 (7) | H12—N1—H13 | 111.5 (12) |
C1—O1—Cu1 | 112.83 (16) | H11—N1—H14 | 107.5 (12) |
C2—O4—Cu1 | 111.96 (15) | H12—N1—H14 | 108.5 (12) |
C3—O5—Cu1 | 112.24 (15) | H13—N1—H14 | 109.8 (12) |
C4—O8—Cu1 | 111.88 (16) | H181—O18—H182 | 106.3 (18) |
C5—O9—Cu2 | 111.76 (17) | H21—N2—H22 | 112.4 (13) |
C6—O12—Cu2 | 111.80 (16) | H21—N2—H23 | 111.3 (13) |
C7—O13—Cu2 | 111.94 (16) | H22—N2—H23 | 109.2 (12) |
C8—O16—Cu2 | 112.53 (17) | H21—N2—H24 | 109.4 (12) |
O2—C1—O1 | 126.1 (2) | H22—N2—H24 | 107.0 (12) |
O2—C1—C2 | 119.8 (2) | H23—N2—H24 | 107.3 (12) |
O1—C1—C2 | 114.2 (2) | H191—O19—H192 | 103.5 (17) |
O3—C2—O4 | 126.1 (2) | H31—N3—H32 | 108.8 (12) |
O3—C2—C1 | 119.1 (2) | H31—N3—H33 | 108.1 (12) |
O4—C2—C1 | 114.8 (2) | H32—N3—H33 | 109.9 (12) |
O6—C3—O5 | 125.7 (2) | H31—N3—H34 | 109.1 (12) |
O6—C3—C4 | 120.2 (2) | H32—N3—H34 | 111.9 (13) |
O5—C3—C4 | 114.1 (2) | H33—N3—H34 | 109.0 (12) |
O7—C4—O8 | 126.5 (2) | H41—N4—H42 | 109.8 (12) |
O7—C4—C3 | 118.0 (2) | H41—N4—H43 | 111.0 (13) |
O8—C4—C3 | 115.5 (2) | H42—N4—H43 | 110.5 (12) |
O10—C5—O9 | 125.8 (2) | H41—N4—H44 | 108.2 (12) |
O10—C5—C6 | 119.3 (2) | H42—N4—H44 | 107.6 (12) |
O9—C5—C6 | 114.9 (2) | H43—N4—H44 | 109.7 (12) |
O11—C6—O12 | 125.8 (2) | | |
| | | |
O8—Cu1—O1—C1 | 58.1 (16) | O2—C1—C2—O3 | −0.5 (4) |
O4—Cu1—O1—C1 | −4.89 (17) | O1—C1—C2—O3 | 178.7 (2) |
O5—Cu1—O1—C1 | 176.69 (17) | O2—C1—C2—O4 | −179.9 (2) |
O1—Cu1—O4—C2 | 4.48 (16) | O1—C1—C2—O4 | −0.7 (3) |
O8—Cu1—O4—C2 | −173.15 (16) | Cu1—O5—C3—O6 | −173.4 (2) |
O5—Cu1—O4—C2 | 140.3 (19) | Cu1—O5—C3—C4 | 7.5 (2) |
O1—Cu1—O5—C3 | 174.69 (16) | Cu1—O8—C4—O7 | 177.8 (2) |
O8—Cu1—O5—C3 | −7.65 (16) | Cu1—O8—C4—C3 | −3.5 (2) |
O4—Cu1—O5—C3 | 39 (2) | O6—C3—C4—O7 | −3.1 (4) |
O1—Cu1—O8—C4 | 124.7 (15) | O5—C3—C4—O7 | 176.1 (2) |
O4—Cu1—O8—C4 | −172.38 (16) | O6—C3—C4—O8 | 178.0 (2) |
O5—Cu1—O8—C4 | 5.97 (16) | O5—C3—C4—O8 | −2.8 (3) |
O12—Cu2—O9—C5 | 3.06 (16) | Cu2—O9—C5—O10 | 179.5 (2) |
O16—Cu2—O9—C5 | 106.3 (9) | Cu2—O9—C5—C6 | 0.3 (3) |
O13—Cu2—O9—C5 | 177.32 (16) | Cu2—O12—C6—O11 | −173.4 (2) |
O16—Cu2—O12—C6 | 178.47 (16) | Cu2—O12—C6—C5 | 7.9 (3) |
O9—Cu2—O12—C6 | −6.33 (16) | O10—C5—C6—O11 | −3.8 (4) |
O13—Cu2—O12—C6 | −84.4 (8) | O9—C5—C6—O11 | 175.5 (2) |
O12—Cu2—O13—C7 | −106.5 (8) | O10—C5—C6—O12 | 175.0 (2) |
O16—Cu2—O13—C7 | −8.81 (16) | O9—C5—C6—O12 | −5.7 (3) |
O9—Cu2—O13—C7 | 175.85 (16) | Cu2—O13—C7—O14 | −172.8 (2) |
O12—Cu2—O16—C8 | −178.91 (16) | Cu2—O13—C7—C8 | 8.7 (2) |
O9—Cu2—O16—C8 | 78.2 (9) | Cu2—O16—C8—O15 | 176.5 (2) |
O13—Cu2—O16—C8 | 6.93 (16) | Cu2—O16—C8—C7 | −4.0 (2) |
Cu1—O1—C1—O2 | −176.5 (2) | O14—C7—C8—O15 | −2.4 (4) |
Cu1—O1—C1—C2 | 4.3 (3) | O13—C7—C8—O15 | 176.2 (2) |
Cu1—O4—C2—O3 | 177.4 (2) | O14—C7—C8—O16 | 178.1 (2) |
Cu1—O4—C2—C1 | −3.3 (3) | O13—C7—C8—O16 | −3.3 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O17—H171···O14ii | 0.73 (2) | 2.27 (2) | 2.870 (3) | 140 (2) |
O17—H171···O15ii | 0.73 (2) | 2.38 (2) | 3.025 (3) | 147 (2) |
O17—H172···O10iii | 0.74 (2) | 2.00 (2) | 2.733 (3) | 169 (2) |
N1—H11···O15ii | 0.88 (2) | 2.03 (2) | 2.873 (3) | 161 (2) |
N1—H12···O11iii | 0.87 (2) | 2.12 (2) | 2.948 (3) | 159 (2) |
N1—H12···O10iii | 0.87 (2) | 2.47 (2) | 2.930 (3) | 114 (2) |
N1—H12···O11iv | 0.87 (2) | 2.54 (2) | 3.023 (3) | 117 (2) |
N1—H13···O13 | 0.87 (2) | 2.16 (2) | 2.993 (3) | 162 (2) |
N1—H14···O3iv | 0.88 (2) | 2.04 (2) | 2.871 (3) | 158 (2) |
O18—H181···O9v | 0.72 (2) | 2.20 (2) | 2.900 (3) | 162 (2) |
O18—H182···O6vi | 0.73 (2) | 2.14 (2) | 2.816 (3) | 154 (2) |
N2—H21···O16vii | 0.86 (2) | 2.33 (2) | 3.025 (3) | 138 (2) |
N2—H21···O12iii | 0.86 (2) | 2.50 (2) | 2.977 (3) | 116 (2) |
N2—H22···O18 | 0.88 (2) | 2.10 (2) | 2.901 (3) | 151 (2) |
N2—H22···O16iii | 0.88 (2) | 2.63 (2) | 3.093 (3) | 114 (2) |
N2—H23···O19 | 0.87 (2) | 2.09 (2) | 2.958 (3) | 172 (2) |
N2—H24···O4vii | 0.88 (2) | 2.27 (2) | 3.118 (3) | 162 (2) |
O19—H191···O1vi | 0.73 (2) | 2.17 (2) | 2.835 (3) | 151 (2) |
O19—H192···O14 | 0.74 (2) | 2.23 (2) | 2.933 (3) | 160 (2) |
N3—H31···O2vi | 0.88 (2) | 1.98 (2) | 2.819 (3) | 159 (2) |
N3—H32···O5 | 0.86 (2) | 2.03 (2) | 2.880 (3) | 175 (2) |
N3—H33···O17viii | 0.88 (2) | 2.11 (2) | 2.989 (3) | 172 (2) |
N3—H34···O6ix | 0.87 (2) | 2.14 (2) | 2.953 (3) | 157 (2) |
N3—H34···O7ix | 0.87 (2) | 2.27 (2) | 2.838 (3) | 124 (2) |
N4—H41···O10iv | 0.87 (2) | 2.28 (2) | 3.020 (3) | 143 (2) |
N4—H42···O19 | 0.87 (2) | 2.15 (2) | 2.965 (3) | 155 (2) |
N4—H42···O11iii | 0.87 (2) | 2.38 (2) | 2.818 (3) | 111 (2) |
N4—H43···O3iv | 0.87 (2) | 2.27 (2) | 2.975 (3) | 139 (2) |
N4—H43···O2iv | 0.86 (2) | 2.29 (2) | 2.945 (3) | 133 (2) |
N4—H44···O7vii | 0.88 (2) | 1.90 (2) | 2.769 (3) | 169 (2) |
Symmetry codes: (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) x, y+1, z; (vi) −x+1, y+1/2, −z+1/2; (vii) x, −y+3/2, z−1/2; (viii) x+1, y, z; (ix) −x+1, y−1/2, −z+1/2. |
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