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metal-organic compounds
The Cu atoms in the two independent cations of the title compound, [Cu(C2H3O2)(C10H8N2)2]2(C9H6O5)·6H2O, show square-pyramidal coordination, with one N atom of a chelating heterocycle occupying the apical site. The anions interact, via hydrogen bonds, with the solvent water molecules to form sheets, and the cations occupy the spaces between the sheets.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402327X/su6144sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680402327X/su6144Isup2.hkl |
CCDC reference: 252790
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.106
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.490 0.851 Tmin' and Tmax expected: 0.706 0.847 RR' = 0.690 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.69 PLAT417_ALERT_2_B Short Inter D-H..H-D H3W2 .. H3W2 .. 1.58 Ang.
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 10.64 Cell volume su given = 7.00 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N6 - C34 .. 5.31 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O9 - C53 .. 5.26 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C23 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 N3 -CU1 -N1 -C3 70.90 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N3 -CU1 -N1 -C7 -107.70 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 26 N1 -CU1 -N3 -C17 -2.10 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 30 N1 -CU1 -N3 -C13 -178.00 41.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42 N7 -CU2 -N5 -C29 151.40 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 46 N7 -CU2 -N5 -C25 -26.80 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 58 N5 -CU2 -N7 -C39 -43.70 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 62 N5 -CU2 -N7 -C35 128.40 0.60 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.840(10) ...... 3.00 su-Rat O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Rat O3W -H3W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.840(10) ...... 4.00 su-Rat O4W -H4W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat O5W -H5W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O5W -H5W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O6W -H6W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O6W -H6W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H2# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.840(10) ...... 3.00 su-Rat O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Rat O3W -H5# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.840(10) ...... 4.00 su-Rat O4W -H7# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat O5W -H9# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O5W -H10# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O6W -H11# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O6W -H12# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.91(3), Rep 1.900(10) ...... 3.00 su-Rat H2# -O5 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.08(3), Rep 2.080(10) ...... 3.00 su-Rat H1# -O3W 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.00(3), Rep 2.000(10) ...... 3.00 su-Rat H5# -O9 1.555 1.556 PLAT736_ALERT_1_C H...A Calc 1.95(4), Rep 1.950(10) ...... 4.00 su-Rat H10# -O1W 1.555 2.666 PLAT736_ALERT_1_C H...A Calc 1.91(3), Rep 1.910(10) ...... 3.00 su-Rat H11# -O9 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.97(4), Rep 1.970(10) ...... 4.00 su-Rat H12# -O2W 1.555 1.554
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 41 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 25 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 9 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu(C2H3O2)(C10H8N2)2]2(C9H6O5).6H2O | Z = 2 |
Mr = 1172.14 | F(000) = 1216 |
Triclinic, P1 | Dx = 1.462 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 14.385 (2) Å | Cell parameters from 24035 reflections |
b = 14.605 (2) Å | θ = 3.3–27.4° |
c = 14.655 (2) Å | µ = 0.88 mm−1 |
α = 86.95 (3)° | T = 295 K |
β = 67.22 (3)° | Prism, colorless |
γ = 70.38 (3)° | 0.39 × 0.26 × 0.19 mm |
V = 2663.5 (7) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 11950 independent reflections |
Radiation source: fine-focus sealed tube | 7589 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
Tmin = 0.490, Tmax = 0.851 | k = −18→18 |
25444 measured reflections | l = −16→18 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0562P)2] where P = (Fo2 + 2Fc2)/3 |
11950 reflections | (Δ/σ)max = 0.001 |
741 parameters | Δρmax = 0.36 e Å−3 |
18 restraints | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.34160 (2) | 0.15188 (2) | 0.23992 (2) | 0.03732 (10) | |
Cu2 | 0.15910 (2) | 0.37476 (2) | 0.73343 (2) | 0.03987 (10) | |
O1 | 0.39016 (16) | 0.01175 (13) | 0.26043 (13) | 0.0497 (5) | |
O2 | 0.48471 (18) | 0.05024 (17) | 0.33051 (15) | 0.0673 (6) | |
O3 | 0.11679 (16) | 0.51769 (14) | 0.74172 (13) | 0.0528 (5) | |
O4 | 0.04669 (18) | 0.50305 (17) | 0.63510 (15) | 0.0686 (6) | |
O5 | 0.18415 (17) | 0.82297 (17) | 0.88636 (13) | 0.0676 (6) | |
O6 | 0.06630 (16) | 0.91883 (15) | 0.82880 (13) | 0.0554 (5) | |
O7 | 0.17930 (16) | 0.83757 (15) | 0.64672 (12) | 0.0565 (5) | |
O8 | 0.46961 (18) | 0.61600 (19) | 0.21591 (15) | 0.0793 (7) | |
O9 | 0.32143 (19) | 0.69885 (16) | 0.19503 (14) | 0.0692 (6) | |
O1w | 0.38179 (18) | 0.68106 (18) | 0.84137 (16) | 0.0669 (6) | |
H1w1 | 0.389 (2) | 0.657 (3) | 0.8930 (16) | 0.100* | |
H1w2 | 0.3167 (13) | 0.718 (2) | 0.856 (2) | 0.100* | |
O2w | 0.0358 (2) | 0.88652 (17) | 1.07831 (15) | 0.0785 (7) | |
H2w1 | 0.079 (3) | 0.871 (2) | 1.0178 (12) | 0.118* | |
H2w2 | 0.006 (3) | 0.9481 (8) | 1.088 (3) | 0.118* | |
O3w | 0.4522 (3) | 0.6069 (2) | 0.99971 (17) | 0.0984 (9) | |
H3w1 | 0.413 (3) | 0.636 (3) | 1.0569 (16) | 0.148* | |
H3w2 | 0.454 (4) | 0.5477 (12) | 0.999 (3) | 0.148* | |
O4w | −0.0390 (2) | 0.99179 (19) | 0.67893 (17) | 0.0721 (6) | |
H4w1 | 0.000 (3) | 0.956 (2) | 0.707 (2) | 0.108* | |
H4w2 | −0.071 (3) | 1.0484 (12) | 0.710 (2) | 0.108* | |
O5w | 0.6052 (3) | 0.4695 (2) | 0.27852 (19) | 0.0919 (8) | |
H5w1 | 0.565 (3) | 0.5218 (16) | 0.266 (3) | 0.138* | |
H5w2 | 0.613 (3) | 0.4218 (18) | 0.242 (3) | 0.138* | |
O6w | 0.1158 (2) | 0.8171 (2) | 0.22408 (15) | 0.0730 (7) | |
H6w1 | 0.1800 (14) | 0.779 (2) | 0.209 (3) | 0.110* | |
H6w2 | 0.105 (3) | 0.835 (3) | 0.1721 (17) | 0.110* | |
N1 | 0.47087 (16) | 0.13618 (15) | 0.11385 (14) | 0.0385 (5) | |
N2 | 0.28090 (16) | 0.13669 (15) | 0.12746 (14) | 0.0376 (5) | |
N3 | 0.21190 (16) | 0.17997 (15) | 0.36695 (14) | 0.0383 (5) | |
N4 | 0.30879 (16) | 0.29761 (15) | 0.26840 (14) | 0.0358 (5) | |
N5 | 0.02072 (17) | 0.38103 (16) | 0.84684 (16) | 0.0455 (6) | |
N6 | 0.20416 (17) | 0.36082 (15) | 0.86259 (14) | 0.0395 (5) | |
N7 | 0.28905 (17) | 0.35918 (16) | 0.60729 (15) | 0.0411 (5) | |
N8 | 0.19630 (16) | 0.23346 (15) | 0.69031 (14) | 0.0382 (5) | |
C1 | 0.4515 (2) | −0.0086 (2) | 0.30718 (18) | 0.0481 (7) | |
C2 | 0.4833 (3) | −0.1125 (2) | 0.3354 (3) | 0.0761 (10) | |
H2a | 0.5601 | −0.1399 | 0.3122 | 0.114* | |
H2b | 0.4579 | −0.1507 | 0.3057 | 0.114* | |
H2c | 0.4522 | −0.1126 | 0.4064 | 0.114* | |
C3 | 0.5646 (2) | 0.1347 (2) | 0.1120 (2) | 0.0512 (7) | |
H3 | 0.5716 | 0.1388 | 0.1720 | 0.061* | |
C4 | 0.6519 (2) | 0.1273 (2) | 0.0247 (2) | 0.0580 (8) | |
H4 | 0.7161 | 0.1274 | 0.0257 | 0.070* | |
C5 | 0.6418 (2) | 0.1198 (2) | −0.0632 (2) | 0.0573 (8) | |
H5 | 0.6997 | 0.1139 | −0.1231 | 0.069* | |
C6 | 0.5454 (2) | 0.1212 (2) | −0.06268 (19) | 0.0510 (7) | |
H6 | 0.5374 | 0.1169 | −0.1222 | 0.061* | |
C7 | 0.4604 (2) | 0.12889 (17) | 0.02731 (17) | 0.0384 (6) | |
C8 | 0.3553 (2) | 0.12765 (17) | 0.03446 (17) | 0.0371 (6) | |
C9 | 0.3335 (3) | 0.1168 (2) | −0.0476 (2) | 0.0522 (7) | |
H9 | 0.3853 | 0.1116 | −0.1113 | 0.063* | |
C10 | 0.2347 (3) | 0.1137 (2) | −0.0341 (2) | 0.0598 (8) | |
H10 | 0.2189 | 0.1064 | −0.0885 | 0.072* | |
C11 | 0.1597 (2) | 0.1214 (2) | 0.0605 (2) | 0.0589 (8) | |
H11 | 0.0923 | 0.1192 | 0.0713 | 0.071* | |
C12 | 0.1857 (2) | 0.1322 (2) | 0.1392 (2) | 0.0473 (7) | |
H12 | 0.1348 | 0.1367 | 0.2034 | 0.057* | |
C13 | 0.1668 (2) | 0.1138 (2) | 0.41031 (19) | 0.0489 (7) | |
H13 | 0.1933 | 0.0517 | 0.3781 | 0.059* | |
C14 | 0.0814 (2) | 0.1358 (2) | 0.5022 (2) | 0.0560 (8) | |
H14 | 0.0504 | 0.0893 | 0.5308 | 0.067* | |
C15 | 0.0437 (2) | 0.2265 (2) | 0.5500 (2) | 0.0550 (8) | |
H15 | −0.0121 | 0.2417 | 0.6124 | 0.066* | |
C16 | 0.0887 (2) | 0.2959 (2) | 0.50530 (18) | 0.0460 (7) | |
H16 | 0.0632 | 0.3583 | 0.5366 | 0.055* | |
C17 | 0.17323 (19) | 0.26990 (19) | 0.41218 (16) | 0.0363 (6) | |
C18 | 0.22528 (19) | 0.33838 (18) | 0.35559 (17) | 0.0346 (6) | |
C19 | 0.1934 (2) | 0.4354 (2) | 0.3864 (2) | 0.0480 (7) | |
H19 | 0.1360 | 0.4622 | 0.4463 | 0.058* | |
C20 | 0.2481 (2) | 0.4924 (2) | 0.3268 (2) | 0.0562 (8) | |
H20 | 0.2279 | 0.5581 | 0.3464 | 0.067* | |
C21 | 0.3322 (2) | 0.4518 (2) | 0.2386 (2) | 0.0529 (7) | |
H21 | 0.3694 | 0.4894 | 0.1975 | 0.063* | |
C22 | 0.3605 (2) | 0.35490 (19) | 0.21194 (18) | 0.0425 (6) | |
H22 | 0.4180 | 0.3275 | 0.1522 | 0.051* | |
C23 | 0.0688 (2) | 0.5525 (2) | 0.6836 (2) | 0.0508 (7) | |
C24 | 0.0398 (3) | 0.6609 (2) | 0.6770 (3) | 0.0787 (11) | |
H24a | 0.0710 | 0.6738 | 0.6089 | 0.118* | |
H24b | 0.0667 | 0.6871 | 0.7161 | 0.118* | |
H24c | −0.0368 | 0.6908 | 0.7016 | 0.118* | |
C25 | −0.0678 (2) | 0.3869 (2) | 0.8328 (2) | 0.0612 (8) | |
H25 | −0.0663 | 0.3912 | 0.7688 | 0.073* | |
C26 | −0.1603 (3) | 0.3869 (2) | 0.9097 (3) | 0.0749 (11) | |
H26 | −0.2201 | 0.3892 | 0.8980 | 0.090* | |
C27 | −0.1625 (3) | 0.3834 (3) | 1.0041 (3) | 0.0790 (12) | |
H27 | −0.2246 | 0.3840 | 1.0575 | 0.095* | |
C28 | −0.0736 (3) | 0.3789 (2) | 1.0199 (2) | 0.0641 (9) | |
H28 | −0.0753 | 0.3776 | 1.0840 | 0.077* | |
C29 | 0.0194 (2) | 0.37646 (18) | 0.93924 (19) | 0.0428 (6) | |
C30 | 0.1201 (2) | 0.37077 (18) | 0.94878 (17) | 0.0412 (6) | |
C31 | 0.1283 (3) | 0.3763 (2) | 1.0393 (2) | 0.0552 (8) | |
H31 | 0.0690 | 0.3835 | 1.0984 | 0.066* | |
C32 | 0.2238 (3) | 0.3711 (2) | 1.0410 (2) | 0.0649 (9) | |
H32 | 0.2302 | 0.3739 | 1.1014 | 0.078* | |
C33 | 0.3102 (3) | 0.3619 (2) | 0.9541 (2) | 0.0603 (8) | |
H33 | 0.3757 | 0.3592 | 0.9541 | 0.072* | |
C34 | 0.2969 (2) | 0.35683 (19) | 0.8658 (2) | 0.0479 (7) | |
H34 | 0.3553 | 0.3503 | 0.8062 | 0.058* | |
C35 | 0.3294 (2) | 0.4295 (2) | 0.5694 (2) | 0.0560 (8) | |
H35 | 0.3032 | 0.4885 | 0.6074 | 0.067* | |
C36 | 0.4088 (2) | 0.4166 (2) | 0.4756 (3) | 0.0648 (9) | |
H36 | 0.4357 | 0.4664 | 0.4506 | 0.078* | |
C37 | 0.4476 (2) | 0.3303 (2) | 0.4197 (2) | 0.0545 (8) | |
H37 | 0.5002 | 0.3212 | 0.3557 | 0.065* | |
C38 | 0.4086 (2) | 0.2566 (2) | 0.45850 (18) | 0.0457 (7) | |
H38 | 0.4350 | 0.1968 | 0.4220 | 0.055* | |
C39 | 0.32882 (19) | 0.27381 (19) | 0.55341 (17) | 0.0361 (6) | |
C40 | 0.28102 (19) | 0.19929 (18) | 0.60240 (17) | 0.0365 (6) | |
C41 | 0.3191 (2) | 0.1042 (2) | 0.56409 (19) | 0.0491 (7) | |
H41 | 0.3780 | 0.0825 | 0.5041 | 0.059* | |
C42 | 0.2684 (3) | 0.0410 (2) | 0.6161 (2) | 0.0606 (9) | |
H42 | 0.2928 | −0.0237 | 0.5913 | 0.073* | |
C43 | 0.1817 (2) | 0.0749 (2) | 0.7048 (2) | 0.0572 (8) | |
H43 | 0.1462 | 0.0336 | 0.7405 | 0.069* | |
C44 | 0.1486 (2) | 0.1704 (2) | 0.73972 (19) | 0.0467 (7) | |
H44 | 0.0905 | 0.1927 | 0.8002 | 0.056* | |
C45 | 0.1498 (2) | 0.8526 (2) | 0.81959 (19) | 0.0439 (7) | |
C46 | 0.2226 (2) | 0.7971 (2) | 0.71766 (18) | 0.0520 (7) | |
H46a | 0.2937 | 0.8012 | 0.6978 | 0.062* | |
H46b | 0.2291 | 0.7289 | 0.7210 | 0.062* | |
C47 | 0.2327 (2) | 0.7949 (2) | 0.55087 (18) | 0.0457 (7) | |
C48 | 0.3258 (2) | 0.7155 (2) | 0.51860 (19) | 0.0548 (8) | |
H48 | 0.3571 | 0.6863 | 0.5625 | 0.066* | |
C49 | 0.3724 (2) | 0.6796 (2) | 0.41917 (19) | 0.0505 (7) | |
H49 | 0.4368 | 0.6273 | 0.3967 | 0.061* | |
C50 | 0.3259 (2) | 0.7192 (2) | 0.35294 (18) | 0.0435 (7) | |
C51 | 0.2322 (2) | 0.7991 (2) | 0.38747 (19) | 0.0545 (8) | |
H51 | 0.1998 | 0.8277 | 0.3441 | 0.065* | |
C52 | 0.1860 (2) | 0.8372 (2) | 0.4853 (2) | 0.0544 (8) | |
H52 | 0.1234 | 0.8913 | 0.5072 | 0.065* | |
C53 | 0.3767 (3) | 0.6756 (2) | 0.2458 (2) | 0.0510 (8) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03765 (18) | 0.03884 (19) | 0.02918 (15) | −0.01282 (15) | −0.00619 (13) | −0.00247 (12) |
Cu2 | 0.04063 (19) | 0.0417 (2) | 0.03410 (16) | −0.01322 (15) | −0.01143 (14) | −0.00238 (13) |
O1 | 0.0598 (13) | 0.0413 (11) | 0.0439 (10) | −0.0116 (10) | −0.0209 (10) | 0.0023 (8) |
O2 | 0.0810 (16) | 0.0682 (15) | 0.0562 (12) | −0.0306 (13) | −0.0246 (12) | −0.0069 (11) |
O3 | 0.0703 (14) | 0.0430 (12) | 0.0397 (10) | −0.0109 (10) | −0.0225 (10) | −0.0020 (8) |
O4 | 0.0721 (15) | 0.0719 (16) | 0.0612 (13) | −0.0200 (13) | −0.0277 (12) | −0.0102 (11) |
O5 | 0.0666 (14) | 0.0772 (16) | 0.0367 (10) | 0.0026 (12) | −0.0191 (10) | −0.0057 (10) |
O6 | 0.0496 (12) | 0.0553 (13) | 0.0416 (10) | −0.0044 (11) | −0.0086 (9) | −0.0002 (9) |
O7 | 0.0601 (13) | 0.0563 (13) | 0.0353 (9) | 0.0066 (10) | −0.0208 (9) | −0.0123 (9) |
O8 | 0.0575 (15) | 0.103 (2) | 0.0529 (12) | −0.0139 (14) | −0.0039 (11) | −0.0249 (13) |
O9 | 0.0887 (17) | 0.0710 (16) | 0.0402 (11) | −0.0139 (13) | −0.0276 (12) | −0.0040 (10) |
O1w | 0.0569 (14) | 0.0707 (17) | 0.0650 (13) | −0.0200 (12) | −0.0156 (11) | −0.0070 (12) |
O2w | 0.0969 (19) | 0.0670 (16) | 0.0381 (11) | −0.0113 (15) | −0.0058 (11) | −0.0005 (10) |
O3w | 0.115 (2) | 0.108 (2) | 0.0470 (13) | −0.030 (2) | −0.0106 (14) | −0.0155 (14) |
O4w | 0.0751 (17) | 0.0704 (17) | 0.0736 (15) | −0.0192 (14) | −0.0359 (13) | −0.0014 (13) |
O5w | 0.136 (3) | 0.0674 (17) | 0.0767 (17) | −0.0403 (19) | −0.0411 (17) | −0.0020 (14) |
O6w | 0.0731 (16) | 0.093 (2) | 0.0480 (11) | −0.0253 (15) | −0.0203 (11) | −0.0051 (12) |
N1 | 0.0369 (12) | 0.0379 (12) | 0.0350 (11) | −0.0139 (10) | −0.0065 (9) | −0.0041 (9) |
N2 | 0.0383 (12) | 0.0352 (12) | 0.0356 (10) | −0.0119 (10) | −0.0109 (9) | 0.0013 (9) |
N3 | 0.0402 (12) | 0.0429 (13) | 0.0304 (10) | −0.0184 (11) | −0.0085 (9) | −0.0003 (9) |
N4 | 0.0391 (12) | 0.0378 (12) | 0.0312 (10) | −0.0159 (10) | −0.0120 (9) | 0.0011 (9) |
N5 | 0.0383 (13) | 0.0439 (14) | 0.0480 (13) | −0.0129 (11) | −0.0094 (10) | −0.0112 (10) |
N6 | 0.0416 (12) | 0.0392 (13) | 0.0371 (11) | −0.0145 (10) | −0.0145 (10) | 0.0047 (9) |
N7 | 0.0377 (12) | 0.0416 (13) | 0.0449 (12) | −0.0168 (11) | −0.0142 (10) | 0.0023 (10) |
N8 | 0.0404 (12) | 0.0408 (12) | 0.0316 (10) | −0.0149 (10) | −0.0114 (9) | 0.0032 (9) |
C1 | 0.0515 (17) | 0.0465 (17) | 0.0318 (13) | −0.0076 (15) | −0.0082 (13) | −0.0055 (12) |
C2 | 0.089 (3) | 0.062 (2) | 0.084 (2) | −0.018 (2) | −0.049 (2) | 0.0208 (19) |
C3 | 0.0444 (17) | 0.0519 (18) | 0.0509 (16) | −0.0160 (14) | −0.0107 (13) | −0.0112 (14) |
C4 | 0.0394 (16) | 0.0507 (19) | 0.072 (2) | −0.0193 (15) | −0.0046 (15) | −0.0093 (15) |
C5 | 0.0512 (18) | 0.0496 (18) | 0.0510 (17) | −0.0223 (15) | 0.0059 (14) | −0.0040 (14) |
C6 | 0.0599 (19) | 0.0467 (17) | 0.0336 (13) | −0.0219 (15) | −0.0013 (13) | −0.0025 (12) |
C7 | 0.0465 (15) | 0.0266 (13) | 0.0357 (13) | −0.0129 (12) | −0.0084 (11) | −0.0025 (10) |
C8 | 0.0462 (15) | 0.0286 (13) | 0.0330 (12) | −0.0112 (12) | −0.0128 (11) | 0.0008 (10) |
C9 | 0.067 (2) | 0.0516 (18) | 0.0387 (14) | −0.0220 (16) | −0.0203 (14) | 0.0037 (13) |
C10 | 0.077 (2) | 0.060 (2) | 0.0575 (18) | −0.0239 (18) | −0.0411 (17) | 0.0047 (15) |
C11 | 0.0501 (18) | 0.057 (2) | 0.077 (2) | −0.0180 (16) | −0.0325 (17) | 0.0023 (16) |
C12 | 0.0416 (16) | 0.0445 (17) | 0.0503 (15) | −0.0129 (13) | −0.0136 (13) | 0.0010 (13) |
C13 | 0.0498 (17) | 0.0502 (18) | 0.0446 (15) | −0.0225 (15) | −0.0121 (13) | 0.0062 (13) |
C14 | 0.0524 (18) | 0.069 (2) | 0.0469 (16) | −0.0323 (17) | −0.0108 (14) | 0.0138 (15) |
C15 | 0.0474 (17) | 0.075 (2) | 0.0356 (14) | −0.0242 (17) | −0.0053 (12) | 0.0011 (14) |
C16 | 0.0412 (15) | 0.0557 (18) | 0.0352 (13) | −0.0147 (14) | −0.0092 (12) | −0.0059 (12) |
C17 | 0.0316 (13) | 0.0483 (16) | 0.0290 (11) | −0.0140 (12) | −0.0113 (10) | 0.0006 (11) |
C18 | 0.0315 (13) | 0.0387 (15) | 0.0334 (12) | −0.0099 (11) | −0.0139 (10) | −0.0014 (11) |
C19 | 0.0435 (16) | 0.0441 (17) | 0.0489 (15) | −0.0105 (14) | −0.0128 (13) | −0.0083 (13) |
C20 | 0.0587 (19) | 0.0394 (17) | 0.0704 (19) | −0.0199 (15) | −0.0221 (16) | 0.0001 (14) |
C21 | 0.0528 (18) | 0.0460 (18) | 0.0589 (17) | −0.0244 (15) | −0.0149 (14) | 0.0075 (14) |
C22 | 0.0403 (15) | 0.0438 (16) | 0.0392 (13) | −0.0163 (13) | −0.0098 (12) | 0.0025 (12) |
C23 | 0.0484 (17) | 0.0545 (19) | 0.0372 (14) | −0.0115 (15) | −0.0091 (13) | 0.0008 (14) |
C24 | 0.099 (3) | 0.056 (2) | 0.088 (2) | −0.019 (2) | −0.050 (2) | 0.0152 (19) |
C25 | 0.0460 (18) | 0.058 (2) | 0.077 (2) | −0.0154 (16) | −0.0200 (16) | −0.0162 (16) |
C26 | 0.0422 (19) | 0.058 (2) | 0.114 (3) | −0.0207 (17) | −0.0138 (19) | −0.011 (2) |
C27 | 0.048 (2) | 0.065 (2) | 0.097 (3) | −0.0244 (18) | 0.003 (2) | 0.017 (2) |
C28 | 0.057 (2) | 0.060 (2) | 0.0522 (17) | −0.0197 (17) | 0.0012 (15) | 0.0134 (15) |
C29 | 0.0469 (16) | 0.0292 (14) | 0.0429 (14) | −0.0131 (12) | −0.0076 (12) | 0.0008 (11) |
C30 | 0.0528 (17) | 0.0318 (14) | 0.0338 (13) | −0.0136 (13) | −0.0126 (12) | 0.0028 (11) |
C31 | 0.076 (2) | 0.0447 (18) | 0.0367 (14) | −0.0166 (16) | −0.0171 (15) | 0.0033 (12) |
C32 | 0.098 (3) | 0.049 (2) | 0.0537 (18) | −0.0141 (19) | −0.046 (2) | 0.0054 (15) |
C33 | 0.074 (2) | 0.0467 (19) | 0.076 (2) | −0.0180 (17) | −0.0479 (19) | 0.0085 (16) |
C34 | 0.0518 (17) | 0.0388 (16) | 0.0527 (16) | −0.0156 (14) | −0.0204 (14) | 0.0077 (13) |
C35 | 0.0457 (17) | 0.0444 (18) | 0.073 (2) | −0.0186 (15) | −0.0156 (15) | 0.0012 (15) |
C36 | 0.0456 (18) | 0.060 (2) | 0.085 (2) | −0.0272 (17) | −0.0157 (17) | 0.0184 (18) |
C37 | 0.0356 (15) | 0.072 (2) | 0.0518 (16) | −0.0229 (16) | −0.0100 (13) | 0.0146 (16) |
C38 | 0.0363 (15) | 0.0564 (18) | 0.0404 (14) | −0.0152 (14) | −0.0109 (12) | 0.0019 (13) |
C39 | 0.0307 (13) | 0.0418 (15) | 0.0391 (13) | −0.0143 (12) | −0.0155 (11) | 0.0046 (11) |
C40 | 0.0367 (14) | 0.0386 (15) | 0.0349 (12) | −0.0129 (12) | −0.0144 (11) | −0.0003 (11) |
C41 | 0.0485 (17) | 0.0470 (17) | 0.0412 (14) | −0.0151 (14) | −0.0066 (12) | −0.0053 (13) |
C42 | 0.069 (2) | 0.0404 (17) | 0.0616 (18) | −0.0197 (16) | −0.0120 (16) | −0.0061 (14) |
C43 | 0.065 (2) | 0.0480 (19) | 0.0570 (17) | −0.0267 (16) | −0.0163 (15) | 0.0088 (14) |
C44 | 0.0482 (16) | 0.0511 (18) | 0.0375 (13) | −0.0203 (14) | −0.0111 (12) | 0.0072 (12) |
C45 | 0.0460 (17) | 0.0433 (17) | 0.0366 (14) | −0.0146 (14) | −0.0104 (12) | 0.0013 (12) |
C46 | 0.0548 (18) | 0.0534 (18) | 0.0356 (13) | −0.0021 (15) | −0.0182 (13) | −0.0037 (13) |
C47 | 0.0509 (17) | 0.0459 (16) | 0.0340 (13) | −0.0094 (14) | −0.0150 (12) | −0.0059 (12) |
C48 | 0.0548 (18) | 0.0561 (19) | 0.0409 (14) | −0.0014 (15) | −0.0205 (13) | 0.0006 (13) |
C49 | 0.0482 (17) | 0.0459 (17) | 0.0413 (14) | −0.0049 (14) | −0.0096 (13) | −0.0042 (13) |
C50 | 0.0520 (17) | 0.0429 (16) | 0.0349 (13) | −0.0207 (14) | −0.0120 (12) | −0.0015 (12) |
C51 | 0.0607 (19) | 0.060 (2) | 0.0416 (14) | −0.0080 (16) | −0.0287 (14) | −0.0037 (14) |
C52 | 0.0549 (18) | 0.0512 (19) | 0.0458 (15) | 0.0026 (15) | −0.0241 (14) | −0.0089 (13) |
C53 | 0.062 (2) | 0.0496 (18) | 0.0363 (14) | −0.0280 (17) | −0.0053 (14) | −0.0026 (13) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.976 (2) | C13—C14 | 1.387 (4) |
Cu1—N1 | 2.006 (2) | C13—H13 | 0.9300 |
Cu1—N2 | 2.193 (2) | C14—C15 | 1.364 (4) |
Cu1—N4 | 2.048 (2) | C14—H14 | 0.9300 |
Cu1—N3 | 1.998 (2) | C15—C16 | 1.385 (4) |
Cu2—O3 | 1.964 (2) | C15—H15 | 0.9300 |
Cu2—N5 | 2.016 (2) | C16—C17 | 1.395 (3) |
Cu2—N6 | 2.206 (2) | C16—H16 | 0.9300 |
Cu2—N7 | 2.012 (2) | C17—C18 | 1.477 (3) |
Cu2—N8 | 2.020 (2) | C18—C19 | 1.376 (4) |
O1—C1 | 1.267 (3) | C19—C20 | 1.380 (4) |
O2—C1 | 1.232 (3) | C19—H19 | 0.9300 |
O3—C23 | 1.278 (4) | C20—C21 | 1.369 (4) |
O4—C23 | 1.230 (3) | C20—H20 | 0.9300 |
O5—C45 | 1.255 (3) | C21—C22 | 1.367 (4) |
O6—C45 | 1.227 (3) | C21—H21 | 0.9300 |
O7—C47 | 1.374 (3) | C22—H22 | 0.9300 |
O7—C46 | 1.416 (3) | C23—C24 | 1.503 (4) |
O8—C53 | 1.241 (4) | C24—H24a | 0.9600 |
O9—C53 | 1.245 (4) | C24—H24b | 0.9600 |
O1w—H1w1 | 0.84 (1) | C24—H24c | 0.9600 |
O1w—H1w2 | 0.86 (1) | C25—C26 | 1.371 (4) |
O2w—H2w1 | 0.85 (1) | C25—H25 | 0.9300 |
O2w—H2w2 | 0.85 (1) | C26—C27 | 1.370 (5) |
O3w—H3w1 | 0.84 (1) | C26—H26 | 0.9300 |
O3w—H3w2 | 0.86 (1) | C27—C28 | 1.365 (5) |
O4w—H4w1 | 0.84 (1) | C27—H27 | 0.9300 |
O4w—H4w2 | 0.85 (1) | C28—C29 | 1.391 (4) |
O5w—H5w1 | 0.86 (1) | C28—H28 | 0.9300 |
O5w—H5w2 | 0.85 (1) | C29—C30 | 1.484 (4) |
O6w—H6w1 | 0.85 (1) | C30—C31 | 1.385 (4) |
O6w—H6w2 | 0.85 (1) | C31—C32 | 1.360 (4) |
N1—C3 | 1.332 (3) | C31—H31 | 0.9300 |
N1—C7 | 1.348 (3) | C32—C33 | 1.365 (4) |
N2—C12 | 1.337 (3) | C32—H32 | 0.9300 |
N2—C8 | 1.347 (3) | C33—C34 | 1.389 (4) |
N3—C17 | 1.338 (3) | C33—H33 | 0.9300 |
N3—C13 | 1.340 (3) | C34—H34 | 0.9300 |
N4—C22 | 1.344 (3) | C35—C36 | 1.378 (4) |
N4—C18 | 1.357 (3) | C35—H35 | 0.9300 |
N5—C29 | 1.345 (3) | C36—C37 | 1.362 (4) |
N5—C25 | 1.340 (4) | C36—H36 | 0.9300 |
N6—C34 | 1.335 (3) | C37—C38 | 1.374 (4) |
N6—C30 | 1.341 (3) | C37—H37 | 0.9300 |
N7—C39 | 1.335 (3) | C38—C39 | 1.386 (3) |
N7—C35 | 1.337 (3) | C38—H38 | 0.9300 |
N8—C44 | 1.347 (3) | C39—C40 | 1.487 (3) |
N8—C40 | 1.356 (3) | C40—C41 | 1.371 (4) |
C1—C2 | 1.515 (4) | C41—C42 | 1.381 (4) |
C2—H2a | 0.9600 | C41—H41 | 0.9300 |
C2—H2b | 0.9600 | C42—C43 | 1.374 (4) |
C2—H2c | 0.9600 | C42—H42 | 0.9300 |
C3—C4 | 1.380 (4) | C43—C44 | 1.370 (4) |
C3—H3 | 0.9300 | C43—H43 | 0.9300 |
C4—C5 | 1.364 (4) | C44—H44 | 0.9300 |
C4—H4 | 0.9300 | C45—C46 | 1.527 (3) |
C5—C6 | 1.378 (4) | C46—H46a | 0.9700 |
C5—H5 | 0.9300 | C46—H46b | 0.9700 |
C6—C7 | 1.386 (3) | C47—C48 | 1.373 (4) |
C6—H6 | 0.9300 | C47—C52 | 1.383 (4) |
C7—C8 | 1.480 (4) | C48—C49 | 1.392 (4) |
C8—C9 | 1.384 (4) | C48—H48 | 0.9300 |
C9—C10 | 1.374 (4) | C49—C50 | 1.381 (4) |
C9—H9 | 0.9300 | C49—H49 | 0.9300 |
C10—C11 | 1.369 (4) | C50—C51 | 1.384 (4) |
C10—H10 | 0.9300 | C50—C53 | 1.520 (4) |
C11—C12 | 1.375 (4) | C51—C52 | 1.381 (4) |
C11—H11 | 0.9300 | C51—H51 | 0.9300 |
C12—H12 | 0.9300 | C52—H52 | 0.9300 |
O1—Cu1—N1 | 92.96 (9) | C18—C19—H19 | 120.5 |
O1—Cu1—N2 | 96.28 (8) | C20—C19—H19 | 120.5 |
O1—Cu1—N3 | 91.67 (9) | C21—C20—C19 | 119.7 (3) |
O1—Cu1—N4 | 155.77 (8) | C21—C20—H20 | 120.2 |
N1—Cu1—N2 | 78.46 (8) | C19—C20—H20 | 120.2 |
N1—Cu1—N3 | 174.85 (8) | C22—C21—C20 | 118.9 (2) |
N1—Cu1—N4 | 94.85 (9) | C22—C21—H21 | 120.6 |
N2—Cu1—N3 | 103.30 (8) | C20—C21—H21 | 120.6 |
N2—Cu1—N4 | 107.74 (8) | N4—C22—C21 | 122.8 (2) |
N3—Cu1—N4 | 80.00 (9) | N4—C22—H22 | 118.6 |
O3—Cu2—N5 | 91.58 (9) | C21—C22—H22 | 118.6 |
O3—Cu2—N6 | 93.97 (8) | O4—C23—O3 | 124.0 (3) |
O3—Cu2—N7 | 92.38 (9) | O4—C23—C24 | 120.5 (3) |
O3—Cu2—N8 | 164.46 (8) | O3—C23—C24 | 115.5 (3) |
N5—Cu2—N6 | 77.76 (9) | C23—C24—H24a | 109.5 |
N5—Cu2—N7 | 171.03 (9) | C23—C24—H24b | 109.5 |
N5—Cu2—N8 | 93.70 (9) | H24a—C24—H24b | 109.5 |
N6—Cu2—N7 | 109.96 (8) | C23—C24—H24c | 109.5 |
N6—Cu2—N8 | 101.42 (9) | H24a—C24—H24c | 109.5 |
N7—Cu2—N8 | 80.48 (9) | H24b—C24—H24c | 109.5 |
C1—O1—Cu1 | 112.64 (18) | N5—C25—C26 | 122.3 (3) |
C23—O3—Cu2 | 110.21 (19) | N5—C25—H25 | 118.9 |
C47—O7—C46 | 118.1 (2) | C26—C25—H25 | 118.9 |
H1w1—O1w—H1w2 | 110 (2) | C25—C26—C27 | 118.4 (3) |
H2w1—O2w—H2w2 | 109 (2) | C25—C26—H26 | 120.8 |
H3w1—O3w—H3w2 | 110 (2) | C27—C26—H26 | 120.8 |
H4w1—O4w—H4w2 | 110 (2) | C28—C27—C26 | 120.1 (3) |
H5w1—O5w—H5w2 | 109 (2) | C28—C27—H27 | 119.9 |
H6w1—O6w—H6w2 | 110 (2) | C26—C27—H27 | 119.9 |
C3—N1—C7 | 119.1 (2) | C27—C28—C29 | 119.4 (3) |
C3—N1—Cu1 | 123.25 (18) | C27—C28—H28 | 120.3 |
C7—N1—Cu1 | 117.61 (17) | C29—C28—H28 | 120.3 |
C12—N2—C8 | 118.4 (2) | N5—C29—C28 | 120.2 (3) |
C12—N2—Cu1 | 129.57 (18) | N5—C29—C30 | 116.4 (2) |
C8—N2—Cu1 | 111.96 (16) | C28—C29—C30 | 123.4 (3) |
C17—N3—C13 | 119.6 (2) | N6—C30—C31 | 121.5 (3) |
C17—N3—Cu1 | 116.09 (15) | N6—C30—C29 | 115.1 (2) |
C13—N3—Cu1 | 124.20 (18) | C31—C30—C29 | 123.4 (2) |
C22—N4—C18 | 118.1 (2) | C32—C31—C30 | 119.4 (3) |
C22—N4—Cu1 | 127.62 (17) | C32—C31—H31 | 120.3 |
C18—N4—Cu1 | 114.32 (16) | C30—C31—H31 | 120.3 |
C29—N5—C25 | 119.6 (2) | C31—C32—C33 | 120.2 (3) |
C29—N5—Cu2 | 117.98 (18) | C31—C32—H32 | 119.9 |
C25—N5—Cu2 | 122.4 (2) | C33—C32—H32 | 119.9 |
C34—N6—C30 | 118.2 (2) | C32—C33—C34 | 117.7 (3) |
C34—N6—Cu2 | 128.82 (18) | C32—C33—H33 | 121.1 |
C30—N6—Cu2 | 112.33 (17) | C34—C33—H33 | 121.1 |
C39—N7—C35 | 118.9 (2) | N6—C34—C33 | 123.0 (3) |
C39—N7—Cu2 | 115.07 (16) | N6—C34—H34 | 118.5 |
C35—N7—Cu2 | 125.58 (19) | C33—C34—H34 | 118.5 |
C44—N8—C40 | 117.5 (2) | N7—C35—C36 | 121.6 (3) |
C44—N8—Cu2 | 127.50 (17) | N7—C35—H35 | 119.2 |
C40—N8—Cu2 | 114.95 (16) | C36—C35—H35 | 119.2 |
O2—C1—O1 | 124.1 (3) | C37—C36—C35 | 119.5 (3) |
O2—C1—C2 | 119.7 (3) | C37—C36—H36 | 120.3 |
O1—C1—C2 | 116.1 (3) | C35—C36—H36 | 120.3 |
C1—C2—H2a | 109.5 | C36—C37—C38 | 119.5 (3) |
C1—C2—H2b | 109.5 | C36—C37—H37 | 120.3 |
H2a—C2—H2b | 109.5 | C38—C37—H37 | 120.3 |
C1—C2—H2c | 109.5 | C37—C38—C39 | 118.4 (3) |
H2a—C2—H2c | 109.5 | C37—C38—H38 | 120.8 |
H2b—C2—H2c | 109.5 | C39—C38—H38 | 120.8 |
N1—C3—C4 | 122.7 (3) | N7—C39—C38 | 122.1 (2) |
N1—C3—H3 | 118.7 | N7—C39—C40 | 115.1 (2) |
C4—C3—H3 | 118.7 | C38—C39—C40 | 122.8 (2) |
C5—C4—C3 | 118.5 (3) | N8—C40—C41 | 122.4 (2) |
C5—C4—H4 | 120.7 | N8—C40—C39 | 113.8 (2) |
C3—C4—H4 | 120.7 | C41—C40—C39 | 123.8 (2) |
C4—C5—C6 | 119.6 (3) | C40—C41—C42 | 118.9 (2) |
C4—C5—H5 | 120.2 | C40—C41—H41 | 120.5 |
C6—C5—H5 | 120.2 | C42—C41—H41 | 120.5 |
C5—C6—C7 | 119.4 (3) | C43—C42—C41 | 119.3 (3) |
C5—C6—H6 | 120.3 | C43—C42—H42 | 120.3 |
C7—C6—H6 | 120.3 | C41—C42—H42 | 120.3 |
N1—C7—C6 | 120.7 (3) | C44—C43—C42 | 118.9 (3) |
N1—C7—C8 | 116.5 (2) | C44—C43—H43 | 120.6 |
C6—C7—C8 | 122.9 (2) | C42—C43—H43 | 120.6 |
N2—C8—C9 | 121.3 (2) | N8—C44—C43 | 122.9 (2) |
N2—C8—C7 | 115.4 (2) | N8—C44—H44 | 118.5 |
C9—C8—C7 | 123.3 (2) | C43—C44—H44 | 118.5 |
C10—C9—C8 | 119.5 (3) | O6—C45—O5 | 127.0 (2) |
C10—C9—H9 | 120.3 | O6—C45—C46 | 119.0 (3) |
C8—C9—H9 | 120.3 | O5—C45—C46 | 113.9 (3) |
C11—C10—C9 | 119.2 (3) | O7—C46—C45 | 109.9 (2) |
C11—C10—H10 | 120.4 | O7—C46—H46a | 109.7 |
C9—C10—H10 | 120.4 | C45—C46—H46a | 109.7 |
C10—C11—C12 | 118.8 (3) | O7—C46—H46b | 109.7 |
C10—C11—H11 | 120.6 | C45—C46—H46b | 109.7 |
C12—C11—H11 | 120.6 | H46a—C46—H46b | 108.2 |
N2—C12—C11 | 122.8 (3) | O7—C47—C48 | 124.5 (3) |
N2—C12—H12 | 118.6 | O7—C47—C52 | 115.4 (2) |
C11—C12—H12 | 118.6 | C48—C47—C52 | 120.1 (2) |
N3—C13—C14 | 121.5 (3) | C47—C48—C49 | 118.9 (3) |
N3—C13—H13 | 119.2 | C47—C48—H48 | 120.5 |
C14—C13—H13 | 119.2 | C49—C48—H48 | 120.5 |
C15—C14—C13 | 119.2 (3) | C50—C49—C48 | 122.0 (3) |
C15—C14—H14 | 120.4 | C50—C49—H49 | 119.0 |
C13—C14—H14 | 120.4 | C48—C49—H49 | 119.0 |
C14—C15—C16 | 119.9 (2) | C49—C50—C51 | 117.8 (2) |
C14—C15—H15 | 120.1 | C49—C50—C53 | 120.6 (3) |
C16—C15—H15 | 120.1 | C51—C50—C53 | 121.6 (3) |
C15—C16—C17 | 118.3 (3) | C52—C51—C50 | 121.0 (3) |
C15—C16—H16 | 120.9 | C52—C51—H51 | 119.5 |
C17—C16—H16 | 120.9 | C50—C51—H51 | 119.5 |
N3—C17—C16 | 121.5 (2) | C47—C52—C51 | 120.1 (3) |
N3—C17—C18 | 115.11 (19) | C47—C52—H52 | 119.9 |
C16—C17—C18 | 123.4 (2) | C51—C52—H52 | 119.9 |
N4—C18—C19 | 121.7 (2) | O8—C53—O9 | 124.3 (3) |
N4—C18—C17 | 114.1 (2) | O8—C53—C50 | 117.5 (3) |
C19—C18—C17 | 124.2 (2) | O9—C53—C50 | 118.2 (3) |
C18—C19—C20 | 118.9 (2) | ||
N3—Cu1—O1—C1 | −90.72 (18) | C17—N3—C13—C14 | −1.0 (4) |
N1—Cu1—O1—C1 | 87.00 (18) | Cu1—N3—C13—C14 | 175.3 (2) |
N4—Cu1—O1—C1 | −21.7 (3) | N3—C13—C14—C15 | −0.9 (5) |
N2—Cu1—O1—C1 | 165.71 (17) | C13—C14—C15—C16 | 1.8 (5) |
N7—Cu2—O3—C23 | 80.11 (19) | C14—C15—C16—C17 | −0.8 (4) |
N5—Cu2—O3—C23 | −91.84 (19) | C13—N3—C17—C16 | 2.0 (4) |
N8—Cu2—O3—C23 | 18.1 (4) | Cu1—N3—C17—C16 | −174.5 (2) |
N6—Cu2—O3—C23 | −169.68 (18) | C13—N3—C17—C18 | −177.0 (2) |
O1—Cu1—N1—C3 | −82.9 (2) | Cu1—N3—C17—C18 | 6.4 (3) |
N3—Cu1—N1—C3 | 70.9 (11) | C15—C16—C17—N3 | −1.1 (4) |
N4—Cu1—N1—C3 | 74.2 (2) | C15—C16—C17—C18 | 177.8 (3) |
N2—Cu1—N1—C3 | −178.7 (2) | C22—N4—C18—C19 | 0.0 (4) |
O1—Cu1—N1—C7 | 98.54 (19) | Cu1—N4—C18—C19 | 179.4 (2) |
N3—Cu1—N1—C7 | −107.7 (10) | C22—N4—C18—C17 | 179.7 (2) |
N4—Cu1—N1—C7 | −104.41 (18) | Cu1—N4—C18—C17 | −0.9 (3) |
N2—Cu1—N1—C7 | 2.73 (17) | N3—C17—C18—N4 | −3.5 (3) |
O1—Cu1—N2—C12 | 84.2 (2) | C16—C17—C18—N4 | 177.5 (2) |
N3—Cu1—N2—C12 | −9.0 (2) | N3—C17—C18—C19 | 176.1 (2) |
N1—Cu1—N2—C12 | 175.9 (2) | C16—C17—C18—C19 | −2.9 (4) |
N4—Cu1—N2—C12 | −92.6 (2) | N4—C18—C19—C20 | 0.0 (4) |
O1—Cu1—N2—C8 | −93.44 (17) | C17—C18—C19—C20 | −179.7 (3) |
N3—Cu1—N2—C8 | 173.35 (16) | C18—C19—C20—C21 | 0.3 (5) |
N1—Cu1—N2—C8 | −1.69 (16) | C19—C20—C21—C22 | −0.5 (5) |
N4—Cu1—N2—C8 | 89.76 (17) | C18—N4—C22—C21 | −0.3 (4) |
O1—Cu1—N3—C17 | 151.72 (19) | Cu1—N4—C22—C21 | −179.5 (2) |
N1—Cu1—N3—C17 | −2.1 (11) | C20—C21—C22—N4 | 0.5 (5) |
N4—Cu1—N3—C17 | −5.39 (18) | Cu2—O3—C23—O4 | 4.4 (3) |
N2—Cu1—N3—C17 | −111.42 (18) | Cu2—O3—C23—C24 | −175.4 (2) |
O1—Cu1—N3—C13 | −24.6 (2) | C29—N5—C25—C26 | −1.1 (4) |
N1—Cu1—N3—C13 | −178 (41) | Cu2—N5—C25—C26 | 177.1 (2) |
N4—Cu1—N3—C13 | 178.2 (2) | N5—C25—C26—C27 | 1.8 (5) |
N2—Cu1—N3—C13 | 72.2 (2) | C25—C26—C27—C28 | −0.7 (5) |
O1—Cu1—N4—C22 | 111.2 (2) | C26—C27—C28—C29 | −1.0 (5) |
N3—Cu1—N4—C22 | −177.4 (2) | C25—N5—C29—C28 | −0.7 (4) |
N1—Cu1—N4—C22 | 2.9 (2) | Cu2—N5—C29—C28 | −179.0 (2) |
N2—Cu1—N4—C22 | −76.5 (2) | C25—N5—C29—C30 | −179.6 (2) |
O1—Cu1—N4—C18 | −68.0 (3) | Cu2—N5—C29—C30 | 2.1 (3) |
N3—Cu1—N4—C18 | 3.30 (17) | C27—C28—C29—N5 | 1.7 (4) |
N1—Cu1—N4—C18 | −176.40 (17) | C27—C28—C29—C30 | −179.5 (3) |
N2—Cu1—N4—C18 | 104.19 (17) | C34—N6—C30—C31 | −0.3 (4) |
O3—Cu2—N5—C29 | −92.4 (2) | Cu2—N6—C30—C31 | −172.1 (2) |
N7—Cu2—N5—C29 | 151.4 (5) | C34—N6—C30—C29 | 178.9 (2) |
N8—Cu2—N5—C29 | 102.2 (2) | Cu2—N6—C30—C29 | 7.2 (3) |
N6—Cu2—N5—C29 | 1.30 (18) | N5—C29—C30—N6 | −6.5 (3) |
O3—Cu2—N5—C25 | 89.4 (2) | C28—C29—C30—N6 | 174.6 (2) |
N7—Cu2—N5—C25 | −26.8 (7) | N5—C29—C30—C31 | 172.7 (2) |
N8—Cu2—N5—C25 | −76.0 (2) | C28—C29—C30—C31 | −6.1 (4) |
N6—Cu2—N5—C25 | −176.9 (2) | N6—C30—C31—C32 | −0.3 (4) |
O3—Cu2—N6—C34 | −84.7 (2) | C29—C30—C31—C32 | −179.5 (3) |
N7—Cu2—N6—C34 | 9.3 (2) | C30—C31—C32—C33 | 0.9 (5) |
N5—Cu2—N6—C34 | −175.4 (2) | C31—C32—C33—C34 | −0.9 (5) |
N8—Cu2—N6—C34 | 93.2 (2) | C30—N6—C34—C33 | 0.4 (4) |
O3—Cu2—N6—C30 | 85.95 (18) | Cu2—N6—C34—C33 | 170.5 (2) |
N7—Cu2—N6—C30 | 179.94 (16) | C32—C33—C34—N6 | 0.2 (4) |
N5—Cu2—N6—C30 | −4.81 (17) | C39—N7—C35—C36 | 1.6 (4) |
N8—Cu2—N6—C30 | −96.16 (18) | Cu2—N7—C35—C36 | −170.3 (2) |
O3—Cu2—N7—C39 | −159.86 (19) | N7—C35—C36—C37 | −0.1 (5) |
N5—Cu2—N7—C39 | −43.7 (7) | C35—C36—C37—C38 | −1.4 (5) |
N8—Cu2—N7—C39 | 6.26 (18) | C36—C37—C38—C39 | 1.2 (4) |
N6—Cu2—N7—C39 | 105.05 (19) | C35—N7—C39—C38 | −1.7 (4) |
O3—Cu2—N7—C35 | 12.3 (2) | Cu2—N7—C39—C38 | 171.0 (2) |
N5—Cu2—N7—C35 | 128.4 (6) | C35—N7—C39—C40 | 178.6 (2) |
N8—Cu2—N7—C35 | 178.4 (3) | Cu2—N7—C39—C40 | −8.7 (3) |
N6—Cu2—N7—C35 | −82.8 (2) | C37—C38—C39—N7 | 0.3 (4) |
O3—Cu2—N8—C44 | −120.7 (3) | C37—C38—C39—C40 | −180.0 (3) |
N7—Cu2—N8—C44 | 175.8 (2) | C44—N8—C40—C41 | −0.7 (4) |
N5—Cu2—N8—C44 | −11.1 (2) | Cu2—N8—C40—C41 | 177.7 (2) |
N6—Cu2—N8—C44 | 67.2 (2) | C44—N8—C40—C39 | −179.8 (2) |
O3—Cu2—N8—C40 | 61.0 (4) | Cu2—N8—C40—C39 | −1.3 (3) |
N7—Cu2—N8—C40 | −2.45 (18) | N7—C39—C40—N8 | 6.6 (3) |
N5—Cu2—N8—C40 | 170.68 (19) | C38—C39—C40—N8 | −173.1 (2) |
N6—Cu2—N8—C40 | −111.07 (18) | N7—C39—C40—C41 | −172.4 (3) |
Cu1—O1—C1—O2 | −5.6 (3) | C38—C39—C40—C41 | 7.9 (4) |
Cu1—O1—C1—C2 | 173.9 (2) | N8—C40—C41—C42 | 0.9 (4) |
C7—N1—C3—C4 | 0.9 (4) | C39—C40—C41—C42 | 179.9 (3) |
Cu1—N1—C3—C4 | −177.7 (2) | C40—C41—C42—C43 | −0.2 (5) |
N1—C3—C4—C5 | −0.9 (5) | C41—C42—C43—C44 | −0.7 (5) |
C3—C4—C5—C6 | 0.8 (4) | C40—N8—C44—C43 | −0.2 (4) |
C4—C5—C6—C7 | −0.8 (4) | Cu2—N8—C44—C43 | −178.4 (2) |
C3—N1—C7—C6 | −0.8 (4) | C42—C43—C44—N8 | 0.9 (5) |
Cu1—N1—C7—C6 | 177.85 (19) | C47—O7—C46—C45 | −178.1 (2) |
C3—N1—C7—C8 | 178.0 (2) | O6—C45—C46—O7 | 2.3 (4) |
Cu1—N1—C7—C8 | −3.3 (3) | O5—C45—C46—O7 | −178.1 (2) |
C5—C6—C7—N1 | 0.7 (4) | C46—O7—C47—C48 | −0.3 (4) |
C5—C6—C7—C8 | −178.0 (3) | C46—O7—C47—C52 | 179.5 (3) |
C12—N2—C8—C9 | 1.8 (4) | O7—C47—C48—C49 | −179.5 (3) |
Cu1—N2—C8—C9 | 179.7 (2) | C52—C47—C48—C49 | 0.7 (5) |
C12—N2—C8—C7 | −177.4 (2) | C47—C48—C49—C50 | −2.3 (5) |
Cu1—N2—C8—C7 | 0.5 (3) | C48—C49—C50—C51 | 2.4 (4) |
N1—C7—C8—N2 | 1.7 (3) | C48—C49—C50—C53 | −177.6 (3) |
C6—C7—C8—N2 | −179.5 (2) | C49—C50—C51—C52 | −0.9 (4) |
N1—C7—C8—C9 | −177.4 (2) | C53—C50—C51—C52 | 179.0 (3) |
C6—C7—C8—C9 | 1.3 (4) | O7—C47—C52—C51 | −179.1 (3) |
N2—C8—C9—C10 | −1.0 (4) | C48—C47—C52—C51 | 0.7 (5) |
C7—C8—C9—C10 | 178.2 (3) | C50—C51—C52—C47 | −0.6 (5) |
C8—C9—C10—C11 | −0.1 (5) | C49—C50—C53—O8 | −12.8 (4) |
C9—C10—C11—C12 | 0.2 (5) | C51—C50—C53—O8 | 167.3 (3) |
C8—N2—C12—C11 | −1.7 (4) | C49—C50—C53—O9 | 164.5 (3) |
Cu1—N2—C12—C11 | −179.2 (2) | C51—C50—C53—O9 | −15.4 (4) |
C10—C11—C12—N2 | 0.7 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w2···O5 | 0.86 (1) | 1.90 (1) | 2.748 (3) | 168 (4) |
O1w—H1w1···O3w | 0.84 (1) | 2.08 (1) | 2.898 (4) | 162 (3) |
O2w—H2w1···O5 | 0.85 (1) | 1.91 (1) | 2.762 (3) | 174 (4) |
O2w—H2w2···O6i | 0.85 (1) | 2.07 (2) | 2.855 (3) | 154 (4) |
O3w—H3w1···O9ii | 0.84 (1) | 2.00 (1) | 2.843 (3) | 178 (4) |
O3w—H3w2···O3wiii | 0.86 (1) | 2.21 (3) | 2.959 (7) | 146 (5) |
O4w—H4w1···O6 | 0.84 (1) | 2.30 (2) | 3.081 (3) | 155 (3) |
O4w—H4w2···O6wiv | 0.85 (1) | 2.02 (1) | 2.858 (4) | 168 (4) |
O5w—H5w1···O8 | 0.86 (1) | 1.92 (2) | 2.757 (4) | 165 (4) |
O5w—H5w2···O1wv | 0.85 (1) | 1.95 (1) | 2.799 (3) | 175 (4) |
O6w—H6w1···O9 | 0.85 (1) | 1.91 (1) | 2.754 (4) | 171 (4) |
O6w—H6w2···O2wvi | 0.85 (1) | 1.97 (1) | 2.794 (4) | 163 (3) |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+2, −z+1; (v) −x+1, −y+1, −z+1; (vi) x, y, z−1. |
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