metal-organic compounds
(μ-5-Carboxybenzene-1,3-dicarboxylato-κ2O1:O3)bis[bis(2,2′-bipyridine-κ2N,N′)copper(II)] 5-carboxybenzene-1,3-dicarboxylate 2,2′-bipyridine solvate tridecahydrate
aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, Křížkovského 10, CZ-771 47 Olomouc, Czech Republic, and bLaboratory of Functional Genomics and Proteomics, Institute of Experimental Biology, Faculty of Science, Masaryk University, Kamenice 5, CZ-625 00 Brno, Czech Republic
*Correspondence e-mail: zdenek.travnicek@upol.cz
The 2(C9H4O6)(C10H8N2)4](C9H4O6)·C10H8N2·13H2O, comprises two formula units. The two CuII centres are bridged by a 5-carboxybenzene-1,3-dicarboxylate (Hbtc) ligand. Each of the metal centres is bonded to four N atoms of two bidentate 2,2′-bipyridine ligands (bpy) and one O atom of the Hbtc ligand in a highly distorted square-pyramidal geometry. The secondary structure is stabilized by a variety of O—H⋯O hydrogen bonds and π–π stacking interactions connecting the complex cations, Hbtc anions, bpy and water molecules of crystallization. Three water molecules are disordered over two positions, with site occupancy factors of ca 0.8 and 0.2.
of the title complex, [CuRelated literature
For related literature, see: Allen (2002); Pech & Pickardt (1988); Chui et al. (1999); Holmes et al. (2004); Wang et al. (2005); Cooper et al. (2005).
Experimental
Crystal data
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808001852/pk2079sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001852/pk2079Isup2.hkl
The title complex was prepared in a quest to synthesize a trinuclear copperII complex in which three metal centres would be connected via a benzene-1,3,5-tricarboxylato anion as a bridging ligand. Specifically: an aqueous solution (20 ml) of benzene-1,3,5-tricarboxylic acid (1 mmol) was added to a suspension of Cu(OH)2 (3 mmol) in water (40 ml). The reaction mixture was refluxed for 3 hrs. During this time period, an ethanolic solution of 2,2'-bipyridine (6 mmol) was added drop-wise to the reaction mixture while stirring. Then, the resulting solution was filtered and left to stand at room temperature. Blue crystals, suitable for single-crystal X-ray analysis, were obtained by slow evaporation of the solvents used over a period of several weeks.
Some atoms of water molecules of crystallization (namely O atoms O75, O82 and O83) were refined as disordered between two positions [the site occupancy factors were refined to 0.788 (4) and 0.212 (4)], where the major positions were refined anisotropically and the minor ones isotropically. C-bound H-atoms were included in the riding model approximation with C—H distances of 0.93 Å, and with Uiso(H) values of 1.2Ueq(Caromatic). The O-bound H atoms were refined, with the O—H distances restrained to 0.85 (2) Å and with Uiso(H) values of 1.5Ueq(Owater); distances are given in Table 1. The maximum and minimum residual electron density peaks were located with distances 1.10 and 0.80 Å from the O24 atom.
A profile of a few (namely 7) low angle reflections has been strongly influenced by shielding by the beam-stopper, therefore these reflextions were excluded from the refinement.
0 - 1 3 5.03 10904.80 27.38 0.175 7.61 0 1 3 6.91 10664.59 27.30 0.173 7.61 1 2 1 55.69 2770.42 20.50 0.088 7.52 1 - 2 1 51.02 2605.64 20.14 0.085 7.52 - 1 -2 2 121.31 1069.63 13.08 0.055 7.09 - 1 -1 3 59.74 743.37 11.72 0.046 7.17 0 3 1 3202.81 5675.92 7.91 0.126 6.36
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title complex. The non-H atoms are drawn as 40% probability displacement ellipsoids. Some of atom labels are omitted for clarity. | |
Fig. 2. Part of the crystal structure showing the formation of O—H···O hydrogen bonds. Most of the water molecules of crystallization, and free Hbtc anions and bpy molecules have been omitted for clarity. | |
Fig. 3. Part of the crystal structure showing the formation of π-π stacking interactions of the C···Cii and C···Nii type connecting free and coordinated bpy molecules [C84···C125ii = 3.544 (5) Å, C92···C61ii = 3.563 (5) Å, C96···C65ii = 3.425 (5) Å, C82···N18ii = 3.526 (6) Å and N15···C63ii = 3.510 (4) Å. Symmetry code: (ii) -x + 1, y + 1/2, -z]. The water molecules and Hbtc anions of crystallization have been omitted for clarity. |
[Cu2(C9H4O6)(C10H8N2)4](C9H4O6)·C10H8N2·13H2O | F(000) = 3240 |
Mr = 1558.45 | Dx = 1.465 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 32974 reflections |
a = 14.4638 (2) Å | θ = 2.6–32.0° |
b = 19.7448 (2) Å | µ = 0.69 mm−1 |
c = 25.0638 (3) Å | T = 120 K |
β = 99.2051 (14)° | Prism, blue |
V = 7065.66 (15) Å3 | 0.3 × 0.3 × 0.25 mm |
Z = 4 |
Oxford Diffraction Xcalibur2+ CCD diffractometer | 23598 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 21012 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 8.3611 pixels mm-1 | θmax = 25.1°, θmin = 2.7° |
rotation method ω scans | h = −17→13 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −22→23 |
Tmin = 0.823, Tmax = 0.840 | l = −29→29 |
41227 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0475P)2 + 5P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
23591 reflections | Δρmax = 0.81 e Å−3 |
2053 parameters | Δρmin = −0.62 e Å−3 |
62 restraints | Absolute structure: Flack (1983), 10782 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.105 (6) |
[Cu2(C9H4O6)(C10H8N2)4](C9H4O6)·C10H8N2·13H2O | V = 7065.66 (15) Å3 |
Mr = 1558.45 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 14.4638 (2) Å | µ = 0.69 mm−1 |
b = 19.7448 (2) Å | T = 120 K |
c = 25.0638 (3) Å | 0.3 × 0.3 × 0.25 mm |
β = 99.2051 (14)° |
Oxford Diffraction Xcalibur2+ CCD diffractometer | 23598 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 21012 reflections with I > 2σ(I) |
Tmin = 0.823, Tmax = 0.840 | Rint = 0.016 |
41227 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | Δρmax = 0.81 e Å−3 |
S = 0.99 | Δρmin = −0.62 e Å−3 |
23591 reflections | Absolute structure: Flack (1983), 10782 Friedel pairs |
2053 parameters | Absolute structure parameter: 0.105 (6) |
62 restraints |
Experimental. Absorption correction (full details): CrysAlis RED (Oxford Diffraction, 2006) Version 1.171.31.7 (release 18–10-2006 CrysAlis171. NET) (compiled Oct 18 2006,16:28:17). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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 > 2σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.31137 (2) | 0.177710 (17) | 0.498235 (14) | 0.01341 (8) | |
Cu2 | 0.18062 (2) | 0.700682 (18) | 0.498203 (14) | 0.01502 (9) | |
Cu3 | 0.17641 (2) | 0.189610 (17) | −0.009072 (14) | 0.01460 (9) | |
Cu4 | 0.32895 (2) | 0.712859 (19) | 0.021961 (15) | 0.01744 (9) | |
O1 | 0.33861 (14) | 0.26860 (11) | 0.46507 (8) | 0.0160 (5) | |
O2 | 0.26838 (15) | 0.30763 (11) | 0.53194 (9) | 0.0191 (5) | |
O3 | 0.21388 (15) | 0.61479 (11) | 0.46425 (8) | 0.0165 (5) | |
O4 | 0.14569 (15) | 0.55112 (11) | 0.52073 (9) | 0.0203 (5) | |
O5 | 0.33234 (18) | 0.52434 (12) | 0.31428 (10) | 0.0289 (6) | |
H5W | 0.357 (3) | 0.535 (2) | 0.2860 (12) | 0.043* | |
O6 | 0.34549 (17) | 0.41255 (12) | 0.30032 (9) | 0.0268 (5) | |
O7 | 0.15079 (15) | 0.28225 (11) | 0.01932 (9) | 0.0189 (5) | |
O8 | 0.22196 (15) | 0.32671 (11) | −0.04501 (9) | 0.0212 (5) | |
O9 | 0.29559 (15) | 0.62361 (11) | 0.05025 (9) | 0.0197 (5) | |
O10 | 0.36466 (16) | 0.56616 (12) | −0.00937 (9) | 0.0234 (5) | |
O11 | 0.1500 (2) | 0.39334 (13) | 0.18856 (11) | 0.0408 (7) | |
H11V | 0.138 (3) | 0.395 (2) | 0.2209 (10) | 0.061* | |
O12 | 0.1995 (2) | 0.49851 (14) | 0.20408 (10) | 0.0433 (7) | |
O13 | 0.48939 (16) | 0.27095 (12) | 0.25271 (10) | 0.0275 (5) | |
O14 | 0.55947 (15) | 0.17417 (11) | 0.23701 (9) | 0.0236 (5) | |
O15 | 0.81789 (16) | 0.48517 (12) | 0.26154 (9) | 0.0266 (5) | |
O16 | 0.66177 (16) | 0.48743 (11) | 0.23960 (10) | 0.0263 (5) | |
O17 | 0.98334 (17) | 0.26919 (13) | 0.25050 (11) | 0.0338 (6) | |
O18 | 0.90396 (16) | 0.17284 (12) | 0.24242 (9) | 0.0261 (5) | |
H18V | 0.957 (2) | 0.152 (2) | 0.2449 (19) | 0.053 (14)* | |
O19 | −0.01066 (18) | 1.02929 (14) | 0.25877 (13) | 0.0455 (7) | |
O20 | 0.05922 (16) | 1.12236 (12) | 0.23636 (10) | 0.0282 (5) | |
O21 | 0.48534 (18) | 1.02573 (13) | 0.26211 (12) | 0.0389 (6) | |
O22 | 0.40450 (18) | 1.12089 (13) | 0.24599 (11) | 0.0336 (6) | |
H22V | 0.459 (2) | 1.134 (3) | 0.240 (2) | 0.069 (17)* | |
O23 | 0.1576 (2) | 0.81674 (15) | 0.29295 (15) | 0.0640 (10) | |
O24 | 0.3095 (2) | 0.81320 (16) | 0.28853 (19) | 0.0825 (13) | |
H96W | 0.363 (3) | 0.812 (4) | 0.2307 (14) | 0.124* | |
N1 | 0.19855 (17) | 0.16962 (14) | 0.44222 (10) | 0.0162 (6) | |
N2 | 0.22886 (18) | 0.12282 (13) | 0.54098 (10) | 0.0153 (6) | |
N3 | 0.42266 (17) | 0.18089 (13) | 0.55566 (9) | 0.0145 (5) | |
N4 | 0.40706 (17) | 0.11554 (13) | 0.46193 (10) | 0.0134 (5) | |
N5 | 0.27994 (19) | 0.76810 (14) | 0.47087 (11) | 0.0211 (6) | |
N6 | 0.28802 (18) | 0.69145 (15) | 0.55868 (10) | 0.0214 (6) | |
N7 | 0.07151 (17) | 0.71179 (14) | 0.44082 (9) | 0.0148 (5) | |
N8 | 0.09715 (17) | 0.75529 (13) | 0.54096 (10) | 0.0136 (5) | |
N9 | 0.29242 (17) | 0.18288 (14) | 0.04450 (10) | 0.0177 (6) | |
N10 | 0.25432 (18) | 0.13091 (13) | −0.05250 (10) | 0.0164 (6) | |
N11 | 0.06172 (17) | 0.18895 (14) | −0.06423 (10) | 0.0161 (5) | |
N12 | 0.08538 (18) | 0.12943 (13) | 0.03232 (10) | 0.0150 (6) | |
N13 | 0.24614 (19) | 0.78209 (14) | 0.06155 (12) | 0.0224 (6) | |
N14 | 0.21206 (18) | 0.71632 (15) | −0.03157 (10) | 0.0222 (6) | |
N15 | 0.40951 (18) | 0.76683 (14) | −0.02380 (10) | 0.0164 (6) | |
N16 | 0.44576 (17) | 0.71712 (14) | 0.07413 (10) | 0.0166 (6) | |
N17 | 0.7504 (2) | 0.41281 (17) | 0.06410 (11) | 0.0314 (7) | |
N18 | 0.7371 (2) | 0.49218 (16) | −0.06644 (11) | 0.0285 (7) | |
N19 | 0.7651 (2) | 0.48036 (14) | 0.55385 (11) | 0.0244 (6) | |
N20 | 0.7330 (2) | 0.39145 (15) | 0.42675 (11) | 0.0263 (7) | |
C1 | 0.28239 (19) | 0.38173 (15) | 0.45829 (12) | 0.0139 (6) | |
C2 | 0.2410 (2) | 0.43563 (15) | 0.48184 (12) | 0.0142 (6) | |
H2 | 0.2232 | 0.4302 | 0.5156 | 0.017* | |
C3 | 0.22635 (19) | 0.49735 (15) | 0.45522 (12) | 0.0135 (6) | |
C4 | 0.2508 (2) | 0.50419 (15) | 0.40398 (12) | 0.0153 (6) | |
H4 | 0.2398 | 0.5450 | 0.3856 | 0.018* | |
C5 | 0.2916 (2) | 0.45069 (15) | 0.37996 (12) | 0.0159 (6) | |
C6 | 0.30695 (19) | 0.38950 (15) | 0.40747 (12) | 0.0156 (6) | |
H6 | 0.3339 | 0.3535 | 0.3916 | 0.019* | |
C7 | 0.2982 (2) | 0.31530 (16) | 0.48793 (12) | 0.0137 (6) | |
C8 | 0.1907 (2) | 0.55794 (17) | 0.48279 (12) | 0.0148 (7) | |
C9 | 0.3247 (2) | 0.46001 (16) | 0.32702 (12) | 0.0197 (7) | |
C10 | 0.1911 (2) | 0.19425 (16) | 0.39166 (12) | 0.0183 (7) | |
H10 | 0.2419 | 0.2169 | 0.3815 | 0.022* | |
C11 | 0.1105 (2) | 0.18690 (17) | 0.35450 (13) | 0.0245 (7) | |
H11 | 0.1074 | 0.2034 | 0.3195 | 0.029* | |
C12 | 0.0343 (2) | 0.15459 (18) | 0.37027 (14) | 0.0250 (8) | |
H12 | −0.0211 | 0.1498 | 0.3460 | 0.030* | |
C13 | 0.0409 (2) | 0.12944 (17) | 0.42230 (13) | 0.0220 (7) | |
H13 | −0.0098 | 0.1078 | 0.4336 | 0.026* | |
C14 | 0.1252 (2) | 0.13729 (15) | 0.45743 (12) | 0.0149 (7) | |
C15 | 0.1420 (2) | 0.11020 (16) | 0.51299 (13) | 0.0165 (7) | |
C16 | 0.0764 (2) | 0.07340 (17) | 0.53608 (14) | 0.0220 (7) | |
H16 | 0.0171 | 0.0652 | 0.5167 | 0.026* | |
C17 | 0.1004 (2) | 0.04914 (18) | 0.58816 (14) | 0.0260 (8) | |
H17 | 0.0571 | 0.0247 | 0.6041 | 0.031* | |
C18 | 0.1883 (2) | 0.06134 (17) | 0.61621 (13) | 0.0242 (7) | |
H18 | 0.2053 | 0.0452 | 0.6513 | 0.029* | |
C19 | 0.2521 (2) | 0.09849 (16) | 0.59123 (13) | 0.0186 (7) | |
H19 | 0.3120 | 0.1064 | 0.6100 | 0.022* | |
C20 | 0.4272 (2) | 0.21637 (16) | 0.60201 (12) | 0.0182 (7) | |
H20 | 0.3739 | 0.2390 | 0.6088 | 0.022* | |
C21 | 0.5071 (2) | 0.22035 (17) | 0.63955 (13) | 0.0215 (7) | |
H21 | 0.5078 | 0.2450 | 0.6712 | 0.026* | |
C22 | 0.5866 (2) | 0.18704 (18) | 0.62942 (12) | 0.0224 (7) | |
H22 | 0.6419 | 0.1895 | 0.6541 | 0.027* | |
C23 | 0.5831 (2) | 0.15025 (17) | 0.58247 (12) | 0.0186 (7) | |
H23 | 0.6362 | 0.1278 | 0.5750 | 0.022* | |
C24 | 0.4995 (2) | 0.14680 (16) | 0.54614 (12) | 0.0144 (6) | |
C25 | 0.4881 (2) | 0.10732 (15) | 0.49526 (13) | 0.0138 (7) | |
C26 | 0.5565 (2) | 0.06204 (17) | 0.48350 (14) | 0.0194 (7) | |
H26 | 0.6127 | 0.0570 | 0.5070 | 0.023* | |
C27 | 0.5387 (2) | 0.02481 (17) | 0.43599 (13) | 0.0218 (7) | |
H27 | 0.5829 | −0.0058 | 0.4273 | 0.026* | |
C28 | 0.4554 (2) | 0.03353 (17) | 0.40192 (13) | 0.0216 (7) | |
H28 | 0.4421 | 0.0090 | 0.3699 | 0.026* | |
C29 | 0.3915 (2) | 0.07969 (17) | 0.41623 (13) | 0.0189 (7) | |
H29 | 0.3352 | 0.0860 | 0.3930 | 0.023* | |
C30 | 0.2724 (3) | 0.80565 (17) | 0.42646 (16) | 0.0289 (8) | |
H30 | 0.2159 | 0.8054 | 0.4027 | 0.035* | |
C31 | 0.3464 (3) | 0.84595 (19) | 0.41382 (18) | 0.0395 (10) | |
H31 | 0.3393 | 0.8721 | 0.3826 | 0.047* | |
C32 | 0.4287 (3) | 0.8452 (2) | 0.44894 (19) | 0.0413 (11) | |
H32 | 0.4788 | 0.8711 | 0.4415 | 0.050* | |
C33 | 0.4387 (3) | 0.80710 (18) | 0.49486 (18) | 0.0351 (10) | |
H33 | 0.4951 | 0.8067 | 0.5186 | 0.042* | |
C34 | 0.3628 (2) | 0.76860 (17) | 0.50557 (15) | 0.0245 (8) | |
C35 | 0.3669 (2) | 0.72547 (17) | 0.55386 (14) | 0.0234 (8) | |
C36 | 0.4469 (2) | 0.7193 (2) | 0.59260 (15) | 0.0310 (9) | |
H36 | 0.5011 | 0.7432 | 0.5892 | 0.037* | |
C37 | 0.4445 (3) | 0.6771 (2) | 0.63621 (15) | 0.0374 (10) | |
H37 | 0.4977 | 0.6717 | 0.6622 | 0.045* | |
C38 | 0.3641 (3) | 0.6430 (2) | 0.64131 (15) | 0.0363 (9) | |
H38 | 0.3614 | 0.6152 | 0.6710 | 0.044* | |
C39 | 0.2868 (2) | 0.65089 (18) | 0.60137 (13) | 0.0250 (8) | |
H39 | 0.2322 | 0.6272 | 0.6043 | 0.030* | |
C40 | 0.0657 (2) | 0.68812 (17) | 0.39047 (12) | 0.0200 (7) | |
H40 | 0.1173 | 0.6662 | 0.3806 | 0.024* | |
C41 | −0.0141 (2) | 0.69505 (18) | 0.35280 (12) | 0.0239 (7) | |
H41 | −0.0162 | 0.6781 | 0.3180 | 0.029* | |
C42 | −0.0912 (2) | 0.72764 (17) | 0.36742 (13) | 0.0222 (7) | |
H42 | −0.1461 | 0.7324 | 0.3427 | 0.027* | |
C43 | −0.0856 (2) | 0.75303 (16) | 0.41935 (13) | 0.0184 (7) | |
H43 | −0.1365 | 0.7750 | 0.4300 | 0.022* | |
C44 | −0.0027 (2) | 0.74520 (16) | 0.45529 (12) | 0.0144 (6) | |
C45 | 0.0126 (2) | 0.77124 (15) | 0.51142 (12) | 0.0135 (6) | |
C46 | −0.0515 (2) | 0.81177 (16) | 0.53207 (13) | 0.0162 (7) | |
H46 | −0.1088 | 0.8223 | 0.5113 | 0.019* | |
C47 | −0.0283 (2) | 0.83638 (17) | 0.58449 (13) | 0.0210 (7) | |
H47 | −0.0705 | 0.8631 | 0.5994 | 0.025* | |
C48 | 0.0578 (2) | 0.82089 (17) | 0.61413 (13) | 0.0196 (7) | |
H48 | 0.0752 | 0.8377 | 0.6490 | 0.023* | |
C49 | 0.1176 (2) | 0.77982 (16) | 0.59080 (12) | 0.0181 (7) | |
H49 | 0.1752 | 0.7687 | 0.6111 | 0.022* | |
C51 | 0.2132 (2) | 0.39246 (15) | 0.03421 (12) | 0.0155 (6) | |
C52 | 0.2586 (2) | 0.44886 (15) | 0.01607 (12) | 0.0155 (6) | |
H52 | 0.2758 | 0.4484 | −0.0181 | 0.019* | |
C53 | 0.27799 (19) | 0.50543 (15) | 0.04904 (12) | 0.0146 (6) | |
C54 | 0.2547 (2) | 0.50496 (15) | 0.10099 (12) | 0.0157 (6) | |
H54 | 0.2684 | 0.5424 | 0.1234 | 0.019* | |
C55 | 0.2111 (2) | 0.44889 (16) | 0.11945 (12) | 0.0166 (6) | |
C56 | 0.1904 (2) | 0.39272 (16) | 0.08594 (12) | 0.0169 (6) | |
H56 | 0.1612 | 0.3552 | 0.0983 | 0.020* | |
C57 | 0.1935 (2) | 0.33025 (17) | −0.00082 (13) | 0.0161 (7) | |
C58 | 0.3175 (2) | 0.56947 (17) | 0.02816 (13) | 0.0177 (7) | |
C59 | 0.1858 (2) | 0.44967 (16) | 0.17488 (13) | 0.0203 (7) | |
C60 | 0.3033 (2) | 0.20850 (17) | 0.09471 (12) | 0.0192 (7) | |
H60 | 0.2542 | 0.2325 | 0.1056 | 0.023* | |
C61 | 0.3850 (2) | 0.20020 (18) | 0.13051 (13) | 0.0249 (7) | |
H61 | 0.3907 | 0.2178 | 0.1653 | 0.030* | |
C62 | 0.4587 (2) | 0.16523 (18) | 0.11405 (14) | 0.0256 (8) | |
H62 | 0.5150 | 0.1600 | 0.1374 | 0.031* | |
C63 | 0.4475 (2) | 0.13816 (18) | 0.06249 (14) | 0.0233 (8) | |
H63 | 0.4960 | 0.1142 | 0.0509 | 0.028* | |
C64 | 0.3629 (2) | 0.14723 (16) | 0.02837 (13) | 0.0159 (7) | |
C65 | 0.3415 (2) | 0.11790 (16) | −0.02593 (13) | 0.0166 (7) | |
C66 | 0.4039 (2) | 0.07867 (17) | −0.04936 (13) | 0.0217 (7) | |
H66 | 0.4638 | 0.0702 | −0.0307 | 0.026* | |
C67 | 0.3768 (3) | 0.05244 (18) | −0.10018 (14) | 0.0278 (8) | |
H67 | 0.4179 | 0.0260 | −0.1162 | 0.033* | |
C68 | 0.2875 (2) | 0.06586 (18) | −0.12723 (13) | 0.0264 (8) | |
H68 | 0.2678 | 0.0489 | −0.1618 | 0.032* | |
C69 | 0.2284 (2) | 0.10487 (16) | −0.10186 (13) | 0.0195 (7) | |
H69 | 0.1681 | 0.1134 | −0.1198 | 0.023* | |
C70 | 0.0536 (2) | 0.22199 (17) | −0.11147 (13) | 0.0200 (7) | |
H70 | 0.1035 | 0.2485 | −0.1184 | 0.024* | |
C71 | −0.0253 (2) | 0.21824 (18) | −0.15004 (13) | 0.0230 (7) | |
H71 | −0.0283 | 0.2408 | −0.1829 | 0.028* | |
C72 | −0.1001 (2) | 0.18010 (18) | −0.13877 (12) | 0.0219 (7) | |
H72 | −0.1546 | 0.1769 | −0.1640 | 0.026* | |
C73 | −0.0933 (2) | 0.14699 (17) | −0.08997 (13) | 0.0205 (7) | |
H73 | −0.1435 | 0.1219 | −0.0817 | 0.025* | |
C74 | −0.0111 (2) | 0.15145 (16) | −0.05340 (12) | 0.0154 (7) | |
C75 | 0.0042 (2) | 0.11586 (17) | −0.00025 (13) | 0.0155 (7) | |
C76 | −0.0607 (2) | 0.07034 (18) | 0.01542 (14) | 0.0219 (8) | |
H76 | −0.1169 | 0.0615 | −0.0072 | 0.026* | |
C77 | −0.0399 (2) | 0.03881 (19) | 0.06496 (14) | 0.0266 (8) | |
H77 | −0.0816 | 0.0077 | 0.0757 | 0.032* | |
C78 | 0.0428 (2) | 0.05361 (18) | 0.09859 (13) | 0.0237 (7) | |
H78 | 0.0573 | 0.0333 | 0.1324 | 0.028* | |
C79 | 0.1035 (2) | 0.09946 (17) | 0.08082 (12) | 0.0189 (7) | |
H79 | 0.1591 | 0.1099 | 0.1034 | 0.023* | |
C80 | 0.2676 (3) | 0.81166 (17) | 0.10991 (14) | 0.0268 (8) | |
H80 | 0.3270 | 0.8047 | 0.1296 | 0.032* | |
C81 | 0.2059 (3) | 0.8519 (2) | 0.13192 (18) | 0.0407 (10) | |
H81 | 0.2232 | 0.8717 | 0.1657 | 0.049* | |
C82 | 0.1182 (3) | 0.8621 (2) | 0.10295 (18) | 0.0431 (11) | |
H82 | 0.0750 | 0.8888 | 0.1172 | 0.052* | |
C83 | 0.0942 (3) | 0.8329 (2) | 0.05288 (18) | 0.0384 (10) | |
H83 | 0.0352 | 0.8397 | 0.0327 | 0.046* | |
C84 | 0.1605 (2) | 0.79250 (18) | 0.03275 (15) | 0.0262 (8) | |
C85 | 0.1430 (2) | 0.75727 (19) | −0.01989 (15) | 0.0273 (9) | |
C86 | 0.0596 (3) | 0.7634 (2) | −0.05619 (16) | 0.0386 (10) | |
H86 | 0.0118 | 0.7914 | −0.0482 | 0.046* | |
C87 | 0.0489 (3) | 0.7277 (3) | −0.10390 (18) | 0.0518 (14) | |
H87 | −0.0057 | 0.7323 | −0.1289 | 0.062* | |
C88 | 0.1194 (3) | 0.6849 (2) | −0.11476 (15) | 0.0450 (12) | |
H88 | 0.1124 | 0.6596 | −0.1464 | 0.054* | |
C89 | 0.2004 (3) | 0.6809 (2) | −0.07726 (14) | 0.0338 (9) | |
H89 | 0.2484 | 0.6525 | −0.0842 | 0.041* | |
C90 | 0.3852 (2) | 0.79141 (17) | −0.07358 (13) | 0.0197 (7) | |
H90 | 0.3260 | 0.7812 | −0.0922 | 0.024* | |
C91 | 0.4435 (2) | 0.83120 (18) | −0.09883 (13) | 0.0239 (8) | |
H91 | 0.4241 | 0.8470 | −0.1338 | 0.029* | |
C92 | 0.5317 (2) | 0.84730 (18) | −0.07097 (13) | 0.0223 (7) | |
H92 | 0.5723 | 0.8746 | −0.0866 | 0.027* | |
C93 | 0.5575 (2) | 0.82168 (17) | −0.01930 (13) | 0.0174 (7) | |
H93 | 0.6164 | 0.8313 | 0.0000 | 0.021* | |
C94 | 0.4959 (2) | 0.78182 (16) | 0.00354 (13) | 0.0170 (7) | |
C95 | 0.5169 (2) | 0.75253 (16) | 0.05826 (12) | 0.0154 (7) | |
C96 | 0.6020 (2) | 0.75975 (17) | 0.09243 (13) | 0.0184 (7) | |
H96 | 0.6504 | 0.7843 | 0.0813 | 0.022* | |
C97 | 0.6140 (2) | 0.73017 (18) | 0.14300 (13) | 0.0239 (8) | |
H97 | 0.6709 | 0.7342 | 0.1660 | 0.029* | |
C98 | 0.5412 (2) | 0.69455 (18) | 0.15920 (12) | 0.0245 (7) | |
H98 | 0.5477 | 0.6750 | 0.1934 | 0.029* | |
C99 | 0.4581 (2) | 0.68863 (18) | 0.12335 (12) | 0.0220 (7) | |
H99 | 0.4092 | 0.6640 | 0.1338 | 0.026* | |
C101 | 0.6516 (2) | 0.27466 (16) | 0.24506 (12) | 0.0181 (7) | |
C102 | 0.6532 (2) | 0.34534 (16) | 0.24653 (12) | 0.0176 (7) | |
H102 | 0.5976 | 0.3690 | 0.2466 | 0.021* | |
C103 | 0.7364 (2) | 0.38087 (17) | 0.24787 (11) | 0.0184 (7) | |
C104 | 0.8185 (2) | 0.34460 (16) | 0.24774 (12) | 0.0194 (7) | |
H104 | 0.8747 | 0.3678 | 0.2488 | 0.023* | |
C105 | 0.8185 (2) | 0.27361 (16) | 0.24606 (12) | 0.0180 (6) | |
C106 | 0.7344 (2) | 0.23852 (17) | 0.24439 (11) | 0.0189 (7) | |
H106 | 0.7335 | 0.1915 | 0.2428 | 0.023* | |
C107 | 0.5593 (2) | 0.23822 (16) | 0.24485 (12) | 0.0200 (7) | |
C108 | 0.7384 (2) | 0.45697 (17) | 0.24959 (12) | 0.0213 (7) | |
C109 | 0.9096 (2) | 0.23831 (16) | 0.24654 (12) | 0.0206 (7) | |
C111 | 0.1526 (2) | 1.02452 (17) | 0.25587 (13) | 0.0241 (7) | |
C112 | 0.2361 (2) | 1.05803 (17) | 0.25242 (12) | 0.0217 (7) | |
H112 | 0.2357 | 1.1043 | 0.2456 | 0.026* | |
C113 | 0.3201 (2) | 1.02259 (17) | 0.25911 (13) | 0.0250 (7) | |
C114 | 0.3199 (3) | 0.95301 (17) | 0.26913 (14) | 0.0289 (8) | |
H114 | 0.3759 | 0.9290 | 0.2733 | 0.035* | |
C115 | 0.2363 (3) | 0.91900 (18) | 0.27289 (16) | 0.0356 (9) | |
C116 | 0.1534 (3) | 0.95499 (18) | 0.26585 (15) | 0.0329 (9) | |
H116 | 0.0975 | 0.9326 | 0.2678 | 0.039* | |
C117 | 0.0606 (2) | 1.06102 (18) | 0.24976 (13) | 0.0263 (8) | |
C118 | 0.4105 (2) | 1.05721 (18) | 0.25579 (13) | 0.0246 (8) | |
C119 | 0.2339 (3) | 0.8434 (2) | 0.2850 (2) | 0.0547 (13) | |
C121 | 0.8128 (3) | 0.4034 (2) | 0.10910 (15) | 0.0397 (10) | |
H121 | 0.7936 | 0.3795 | 0.1373 | 0.048* | |
C122 | 0.9034 (3) | 0.4269 (2) | 0.11615 (15) | 0.0369 (9) | |
H122 | 0.9442 | 0.4192 | 0.1482 | 0.044* | |
C123 | 0.9320 (3) | 0.4624 (2) | 0.07414 (16) | 0.0323 (9) | |
H123 | 0.9927 | 0.4792 | 0.0774 | 0.039* | |
C124 | 0.8693 (2) | 0.47241 (18) | 0.02750 (15) | 0.0272 (8) | |
H124 | 0.8874 | 0.4957 | −0.0014 | 0.033* | |
C125 | 0.7792 (2) | 0.44778 (17) | 0.02378 (13) | 0.0224 (7) | |
C126 | 0.7083 (2) | 0.45810 (17) | −0.02582 (13) | 0.0213 (7) | |
C127 | 0.6175 (3) | 0.43349 (18) | −0.02908 (15) | 0.0283 (8) | |
H127 | 0.5988 | 0.4112 | 0.0001 | 0.034* | |
C128 | 0.5554 (3) | 0.4428 (2) | −0.07660 (16) | 0.0353 (9) | |
H128 | 0.4942 | 0.4268 | −0.0798 | 0.042* | |
C129 | 0.5851 (3) | 0.4758 (2) | −0.11905 (16) | 0.0369 (9) | |
H129 | 0.5455 | 0.4817 | −0.1518 | 0.044* | |
C130 | 0.6759 (3) | 0.5001 (2) | −0.11146 (14) | 0.0342 (9) | |
H130 | 0.6954 | 0.5237 | −0.1398 | 0.041* | |
C131 | 0.8305 (3) | 0.48761 (17) | 0.59765 (15) | 0.0297 (8) | |
H131 | 0.8148 | 0.5119 | 0.6267 | 0.036* | |
C132 | 0.9202 (3) | 0.46121 (18) | 0.60242 (16) | 0.0334 (9) | |
H132 | 0.9630 | 0.4671 | 0.6339 | 0.040* | |
C133 | 0.9440 (3) | 0.42613 (19) | 0.55923 (16) | 0.0317 (9) | |
H133 | 1.0039 | 0.4083 | 0.5608 | 0.038* | |
C134 | 0.8777 (2) | 0.41781 (18) | 0.51340 (14) | 0.0248 (7) | |
H134 | 0.8925 | 0.3946 | 0.4836 | 0.030* | |
C135 | 0.7886 (2) | 0.44463 (16) | 0.51249 (14) | 0.0199 (7) | |
C136 | 0.7143 (2) | 0.43522 (16) | 0.46460 (13) | 0.0199 (7) | |
C137 | 0.6293 (2) | 0.46906 (18) | 0.46000 (14) | 0.0266 (8) | |
H137 | 0.6175 | 0.4981 | 0.4873 | 0.032* | |
C138 | 0.5628 (3) | 0.45949 (19) | 0.41503 (15) | 0.0316 (9) | |
H138 | 0.5062 | 0.4828 | 0.4110 | 0.038* | |
C139 | 0.5816 (3) | 0.4147 (2) | 0.37602 (14) | 0.0331 (9) | |
H139 | 0.5377 | 0.4067 | 0.3453 | 0.040* | |
C140 | 0.6666 (3) | 0.3821 (2) | 0.38345 (14) | 0.0331 (9) | |
H140 | 0.6788 | 0.3519 | 0.3570 | 0.040* | |
O74W | 0.6909 (2) | 0.71543 (17) | 0.28672 (11) | 0.0425 (7) | |
H74V | 0.728 (3) | 0.721 (3) | 0.2648 (16) | 0.064* | |
H74W | 0.643 (2) | 0.741 (2) | 0.281 (2) | 0.064* | |
O75W | 0.7064 (3) | 0.90647 (19) | 0.22531 (14) | 0.0431 (10) | 0.788 (4) |
O75V | 0.6244 (13) | 0.8963 (10) | 0.1900 (8) | 0.080 (6)* | 0.212 (4) |
O76W | 0.8487 (3) | 0.86935 (19) | 0.31107 (15) | 0.0671 (10) | |
H76W | 0.867 (4) | 0.902 (2) | 0.3375 (19) | 0.101* | |
H76V | 0.793 (3) | 0.880 (3) | 0.288 (2) | 0.101* | |
O77W | 0.6843 (3) | 0.0412 (2) | 0.11924 (14) | 0.0834 (13) | |
H77W | 0.686 (3) | −0.0053 (10) | 0.119 (3) | 0.125* | |
H77V | 0.659 (4) | 0.035 (3) | 0.0849 (8) | 0.125* | |
O78W | 0.6635 (2) | 0.04126 (19) | 0.22631 (14) | 0.0594 (9) | |
H78W | 0.675 (4) | 0.0062 (11) | 0.2092 (14) | 0.089* | |
H78V | 0.608 (2) | 0.049 (2) | 0.233 (2) | 0.089* | |
O79W | 0.9755 (2) | 0.82287 (15) | 0.25278 (11) | 0.0400 (7) | |
H79W | 1.0384 (17) | 0.811 (2) | 0.2663 (18) | 0.060* | |
H79V | 0.939 (3) | 0.835 (2) | 0.2757 (16) | 0.060* | |
O80W | 0.90325 (19) | 0.59599 (14) | 0.21980 (11) | 0.0367 (7) | |
H80V | 0.867 (3) | 0.573 (2) | 0.2350 (18) | 0.055* | |
H80W | 0.9638 (15) | 0.589 (2) | 0.2304 (18) | 0.055* | |
O81W | 0.08620 (19) | 0.56713 (14) | 0.26830 (11) | 0.0351 (6) | |
H81W | 0.124 (3) | 0.545 (2) | 0.2526 (17) | 0.053* | |
H81V | 0.112 (3) | 0.6042 (14) | 0.2737 (19) | 0.053* | |
O82W | 0.6504 (2) | 0.89441 (15) | 0.38290 (11) | 0.0296 (8) | 0.788 (4) |
O82V | 0.5513 (10) | 0.9154 (7) | 0.3335 (6) | 0.049 (4)* | 0.212 (4) |
O83W | 0.5955 (3) | 0.83319 (17) | 0.28187 (13) | 0.0370 (9) | 0.788 (4) |
O83V | 0.5183 (10) | 0.8217 (7) | 0.2550 (5) | 0.045 (4)* | 0.212 (4) |
O84W | 0.1864 (2) | 0.47151 (16) | 0.61512 (12) | 0.0518 (8) | |
H84W | 0.172 (4) | 0.5093 (19) | 0.6353 (14) | 0.078* | |
H84V | 0.169 (4) | 0.506 (2) | 0.5918 (19) | 0.078* | |
O85W | 0.42569 (17) | 0.56689 (13) | 0.24212 (10) | 0.0294 (6) | |
H85W | 0.447 (3) | 0.5410 (19) | 0.2198 (14) | 0.044* | |
H85V | 0.4769 (19) | 0.583 (2) | 0.2578 (16) | 0.044* | |
O86W | 0.10880 (18) | 0.37182 (13) | 0.28346 (10) | 0.0291 (5) | |
H86W | 0.074 (3) | 0.3391 (16) | 0.2757 (17) | 0.044* | |
H86V | 0.075 (2) | 0.3997 (18) | 0.2960 (16) | 0.044* | |
O87W | 0.38519 (19) | 0.37109 (15) | 0.19668 (11) | 0.0371 (6) | |
H87V | 0.416 (3) | 0.3382 (18) | 0.2124 (17) | 0.056* | |
H87W | 0.372 (3) | 0.383 (2) | 0.2266 (12) | 0.056* | |
O88W | 0.1715 (2) | 0.21905 (17) | 0.18647 (11) | 0.0437 (7) | |
H88W | 0.209 (3) | 0.241 (2) | 0.2127 (15) | 0.066* | |
H88V | 0.137 (3) | 0.191 (2) | 0.2014 (18) | 0.066* | |
O89W | 0.2289 (2) | 0.41587 (16) | −0.12879 (11) | 0.0439 (7) | |
H89V | 0.243 (3) | 0.389 (2) | −0.1008 (14) | 0.066* | |
H89W | 0.1676 (16) | 0.422 (3) | −0.1432 (18) | 0.066* | |
O90W | 0.3005 (2) | 0.26278 (16) | 0.28825 (14) | 0.0529 (8) | |
H90W | 0.3632 (15) | 0.256 (3) | 0.2881 (18) | 0.079* | |
H90V | 0.302 (3) | 0.3081 (9) | 0.296 (2) | 0.079* | |
O91W | 0.82975 (19) | 0.72420 (14) | 0.22237 (11) | 0.0364 (6) | |
H91V | 0.855 (3) | 0.6846 (14) | 0.2226 (19) | 0.055* | |
H91W | 0.879 (2) | 0.749 (2) | 0.2318 (19) | 0.055* | |
O92W | 0.19026 (18) | 0.67920 (14) | 0.29282 (10) | 0.0303 (6) | |
H92W | 0.173 (3) | 0.7211 (12) | 0.2901 (18) | 0.046* | |
H92V | 0.234 (2) | 0.673 (2) | 0.2761 (15) | 0.046* | |
O93W | 0.49044 (18) | 0.47794 (14) | 0.17466 (10) | 0.0324 (6) | |
H93V | 0.5431 (19) | 0.474 (2) | 0.1945 (15) | 0.049* | |
H93W | 0.460 (3) | 0.4440 (16) | 0.1819 (18) | 0.049* | |
O94W | 0.1747 (2) | 0.55864 (17) | 0.69522 (11) | 0.0474 (7) | |
H94W | 0.141 (2) | 0.540 (2) | 0.7173 (18) | 0.071* | |
H94V | 0.207 (2) | 0.547 (3) | 0.7268 (13) | 0.071* | |
O95W | 0.0492 (2) | 0.42768 (15) | 0.82155 (12) | 0.0420 (7) | |
H95W | 0.043 (3) | 0.3924 (17) | 0.8016 (17) | 0.063* | |
H95V | 0.054 (3) | 0.459 (2) | 0.7967 (16) | 0.063* | |
O96W | 0.4212 (3) | 0.7970 (2) | 0.22134 (15) | 0.0695 (10) | |
O97W | 0.60019 (18) | 0.59495 (13) | 0.29311 (10) | 0.0304 (6) | |
H97V | 0.624 (3) | 0.5638 (17) | 0.2757 (16) | 0.046* | |
H97W | 0.629 (3) | 0.6323 (15) | 0.2858 (17) | 0.046* | |
O98W | 0.99812 (17) | 0.46804 (13) | 0.31891 (10) | 0.0293 (6) | |
H98W | 1.022 (3) | 0.5047 (14) | 0.3134 (17) | 0.044* | |
H98V | 0.9443 (16) | 0.473 (2) | 0.3033 (16) | 0.044* | |
O99W | 0.31100 (18) | 0.67711 (14) | 0.21588 (10) | 0.0314 (6) | |
H99W | 0.337 (3) | 0.6392 (14) | 0.2242 (18) | 0.047* | |
H99V | 0.329 (3) | 0.7176 (12) | 0.2229 (18) | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.01105 (18) | 0.0151 (2) | 0.01389 (18) | 0.00045 (14) | 0.00131 (14) | 0.00101 (14) |
Cu2 | 0.01315 (18) | 0.0166 (2) | 0.01539 (17) | 0.00278 (15) | 0.00244 (14) | −0.00345 (15) |
Cu3 | 0.01326 (18) | 0.0163 (2) | 0.01438 (17) | −0.00076 (14) | 0.00261 (14) | −0.00261 (14) |
Cu4 | 0.01484 (19) | 0.0204 (2) | 0.01707 (19) | −0.00415 (15) | 0.00242 (15) | 0.00289 (16) |
O1 | 0.0160 (11) | 0.0128 (11) | 0.0195 (11) | 0.0012 (9) | 0.0032 (9) | 0.0018 (9) |
O2 | 0.0173 (11) | 0.0208 (12) | 0.0207 (12) | 0.0019 (9) | 0.0076 (9) | 0.0056 (9) |
O3 | 0.0192 (11) | 0.0140 (11) | 0.0166 (11) | 0.0046 (9) | 0.0043 (9) | −0.0014 (9) |
O4 | 0.0199 (11) | 0.0224 (12) | 0.0202 (12) | 0.0024 (9) | 0.0083 (10) | −0.0016 (9) |
O5 | 0.0427 (15) | 0.0241 (13) | 0.0233 (13) | 0.0011 (11) | 0.0162 (11) | 0.0039 (10) |
O6 | 0.0357 (14) | 0.0242 (13) | 0.0233 (12) | 0.0048 (10) | 0.0132 (11) | −0.0039 (10) |
O7 | 0.0169 (11) | 0.0171 (12) | 0.0232 (12) | −0.0008 (9) | 0.0051 (9) | −0.0050 (9) |
O8 | 0.0240 (12) | 0.0230 (12) | 0.0184 (12) | −0.0024 (10) | 0.0083 (10) | −0.0054 (9) |
O9 | 0.0204 (12) | 0.0183 (12) | 0.0212 (12) | −0.0032 (9) | 0.0056 (9) | −0.0011 (9) |
O10 | 0.0222 (12) | 0.0271 (13) | 0.0219 (12) | −0.0067 (10) | 0.0065 (10) | −0.0022 (10) |
O11 | 0.070 (2) | 0.0287 (15) | 0.0314 (15) | −0.0088 (13) | 0.0308 (14) | −0.0031 (12) |
O12 | 0.070 (2) | 0.0368 (16) | 0.0274 (14) | −0.0198 (14) | 0.0202 (14) | −0.0128 (12) |
O13 | 0.0227 (13) | 0.0228 (13) | 0.0366 (14) | −0.0035 (10) | 0.0031 (11) | 0.0047 (10) |
O14 | 0.0255 (12) | 0.0183 (12) | 0.0249 (12) | −0.0049 (9) | −0.0021 (9) | 0.0015 (9) |
O15 | 0.0297 (13) | 0.0210 (12) | 0.0289 (13) | −0.0064 (10) | 0.0038 (11) | 0.0006 (10) |
O16 | 0.0240 (13) | 0.0195 (12) | 0.0346 (14) | −0.0014 (10) | 0.0026 (11) | 0.0038 (10) |
O17 | 0.0241 (14) | 0.0295 (14) | 0.0473 (16) | −0.0034 (11) | 0.0041 (12) | −0.0045 (12) |
O18 | 0.0249 (13) | 0.0250 (14) | 0.0299 (13) | 0.0003 (10) | 0.0091 (10) | −0.0018 (10) |
O19 | 0.0269 (14) | 0.0354 (16) | 0.075 (2) | −0.0094 (12) | 0.0116 (14) | −0.0016 (14) |
O20 | 0.0288 (13) | 0.0269 (14) | 0.0297 (13) | −0.0024 (11) | 0.0075 (11) | −0.0016 (10) |
O21 | 0.0316 (15) | 0.0267 (14) | 0.0599 (18) | 0.0024 (12) | 0.0121 (13) | 0.0047 (12) |
O22 | 0.0250 (14) | 0.0253 (14) | 0.0494 (16) | −0.0025 (11) | 0.0025 (12) | 0.0108 (12) |
O23 | 0.058 (2) | 0.0338 (18) | 0.090 (3) | −0.0193 (15) | −0.0196 (18) | 0.0213 (17) |
O24 | 0.050 (2) | 0.0294 (18) | 0.154 (4) | −0.0003 (15) | −0.027 (2) | 0.016 (2) |
N1 | 0.0140 (13) | 0.0182 (14) | 0.0161 (13) | 0.0016 (11) | 0.0018 (10) | −0.0027 (11) |
N2 | 0.0133 (14) | 0.0142 (13) | 0.0192 (14) | −0.0006 (11) | 0.0053 (11) | −0.0027 (11) |
N3 | 0.0156 (13) | 0.0131 (13) | 0.0153 (12) | −0.0013 (11) | 0.0037 (10) | 0.0026 (11) |
N4 | 0.0144 (13) | 0.0141 (13) | 0.0118 (12) | −0.0004 (10) | 0.0022 (10) | 0.0030 (10) |
N5 | 0.0205 (15) | 0.0147 (14) | 0.0306 (16) | 0.0019 (11) | 0.0117 (12) | −0.0035 (12) |
N6 | 0.0169 (13) | 0.0237 (16) | 0.0234 (14) | 0.0085 (12) | 0.0027 (11) | −0.0109 (12) |
N7 | 0.0157 (13) | 0.0153 (14) | 0.0139 (12) | 0.0002 (11) | 0.0039 (10) | −0.0018 (11) |
N8 | 0.0131 (13) | 0.0144 (14) | 0.0135 (13) | −0.0002 (10) | 0.0030 (10) | 0.0000 (10) |
N9 | 0.0167 (13) | 0.0171 (14) | 0.0201 (13) | −0.0032 (11) | 0.0053 (10) | −0.0016 (11) |
N10 | 0.0170 (14) | 0.0172 (15) | 0.0155 (13) | −0.0027 (11) | 0.0039 (11) | −0.0025 (11) |
N11 | 0.0174 (13) | 0.0153 (14) | 0.0168 (12) | 0.0008 (11) | 0.0063 (10) | −0.0026 (11) |
N12 | 0.0147 (13) | 0.0166 (14) | 0.0149 (13) | 0.0007 (11) | 0.0057 (11) | −0.0027 (10) |
N13 | 0.0204 (15) | 0.0174 (15) | 0.0307 (16) | −0.0009 (12) | 0.0076 (12) | 0.0063 (12) |
N14 | 0.0162 (14) | 0.0281 (16) | 0.0213 (14) | −0.0096 (12) | 0.0003 (11) | 0.0052 (13) |
N15 | 0.0142 (13) | 0.0191 (14) | 0.0159 (13) | 0.0010 (11) | 0.0021 (11) | 0.0018 (11) |
N16 | 0.0160 (13) | 0.0158 (14) | 0.0187 (13) | −0.0011 (11) | 0.0045 (10) | 0.0003 (11) |
N17 | 0.0364 (18) | 0.0425 (19) | 0.0158 (14) | −0.0088 (15) | 0.0055 (13) | 0.0038 (13) |
N18 | 0.0327 (17) | 0.0318 (17) | 0.0218 (15) | −0.0002 (13) | 0.0066 (13) | 0.0015 (13) |
N19 | 0.0261 (16) | 0.0214 (15) | 0.0258 (16) | −0.0026 (12) | 0.0041 (13) | 0.0006 (12) |
N20 | 0.0318 (17) | 0.0295 (17) | 0.0195 (15) | 0.0072 (13) | 0.0097 (13) | 0.0025 (12) |
C1 | 0.0095 (14) | 0.0159 (15) | 0.0158 (15) | −0.0024 (11) | 0.0005 (12) | −0.0002 (12) |
C2 | 0.0092 (14) | 0.0175 (16) | 0.0163 (15) | −0.0044 (11) | 0.0037 (12) | −0.0018 (12) |
C3 | 0.0077 (14) | 0.0153 (15) | 0.0173 (15) | −0.0010 (11) | 0.0010 (12) | −0.0045 (12) |
C4 | 0.0146 (15) | 0.0149 (16) | 0.0160 (15) | −0.0006 (12) | 0.0013 (12) | 0.0018 (12) |
C5 | 0.0136 (15) | 0.0195 (16) | 0.0134 (15) | −0.0026 (12) | −0.0009 (12) | −0.0007 (12) |
C6 | 0.0105 (14) | 0.0148 (15) | 0.0219 (16) | 0.0011 (11) | 0.0038 (12) | −0.0058 (12) |
C7 | 0.0098 (15) | 0.0127 (16) | 0.0183 (15) | −0.0025 (12) | 0.0008 (12) | 0.0004 (12) |
C8 | 0.0108 (15) | 0.0163 (18) | 0.0164 (16) | 0.0014 (12) | −0.0008 (12) | −0.0003 (13) |
C9 | 0.0216 (16) | 0.0210 (17) | 0.0163 (16) | −0.0020 (13) | 0.0029 (13) | −0.0001 (13) |
C10 | 0.0223 (16) | 0.0168 (17) | 0.0160 (14) | 0.0016 (13) | 0.0035 (12) | 0.0013 (13) |
C11 | 0.0301 (18) | 0.0247 (19) | 0.0179 (15) | 0.0030 (15) | 0.0016 (13) | −0.0003 (14) |
C12 | 0.0197 (17) | 0.0290 (19) | 0.0235 (18) | 0.0024 (14) | −0.0057 (14) | −0.0079 (14) |
C13 | 0.0178 (17) | 0.0229 (19) | 0.0251 (18) | −0.0012 (14) | 0.0026 (14) | −0.0115 (14) |
C14 | 0.0141 (16) | 0.0115 (16) | 0.0191 (16) | 0.0020 (12) | 0.0024 (13) | −0.0038 (12) |
C15 | 0.0131 (16) | 0.0140 (17) | 0.0233 (17) | 0.0032 (12) | 0.0053 (13) | −0.0029 (13) |
C16 | 0.0187 (17) | 0.0214 (18) | 0.0271 (18) | −0.0047 (14) | 0.0074 (14) | −0.0052 (14) |
C17 | 0.0295 (19) | 0.026 (2) | 0.0260 (18) | −0.0045 (15) | 0.0141 (15) | −0.0034 (15) |
C18 | 0.0326 (19) | 0.0218 (18) | 0.0189 (17) | −0.0022 (15) | 0.0061 (15) | 0.0023 (14) |
C19 | 0.0157 (16) | 0.0208 (18) | 0.0192 (17) | 0.0014 (13) | 0.0024 (13) | 0.0011 (13) |
C20 | 0.0167 (16) | 0.0189 (17) | 0.0196 (16) | 0.0003 (13) | 0.0050 (12) | 0.0001 (13) |
C21 | 0.0220 (17) | 0.0258 (19) | 0.0166 (16) | −0.0052 (14) | 0.0029 (13) | −0.0004 (13) |
C22 | 0.0167 (15) | 0.032 (2) | 0.0163 (15) | −0.0044 (14) | −0.0050 (12) | 0.0043 (14) |
C23 | 0.0119 (16) | 0.0265 (18) | 0.0167 (16) | −0.0004 (13) | 0.0001 (12) | 0.0072 (13) |
C24 | 0.0127 (15) | 0.0155 (16) | 0.0153 (15) | −0.0048 (12) | 0.0032 (12) | 0.0080 (12) |
C25 | 0.0138 (16) | 0.0095 (16) | 0.0189 (16) | −0.0014 (12) | 0.0055 (13) | 0.0071 (12) |
C26 | 0.0147 (16) | 0.0194 (18) | 0.0253 (18) | 0.0035 (13) | 0.0061 (13) | 0.0029 (14) |
C27 | 0.0218 (17) | 0.0198 (18) | 0.0266 (18) | 0.0051 (14) | 0.0129 (14) | 0.0024 (14) |
C28 | 0.0246 (18) | 0.0212 (18) | 0.0207 (17) | 0.0008 (14) | 0.0093 (14) | −0.0021 (13) |
C29 | 0.0178 (16) | 0.0228 (18) | 0.0167 (16) | −0.0034 (13) | 0.0041 (13) | 0.0013 (13) |
C30 | 0.0269 (19) | 0.0186 (18) | 0.045 (2) | 0.0008 (14) | 0.0164 (17) | 0.0002 (16) |
C31 | 0.046 (3) | 0.022 (2) | 0.058 (3) | 0.0045 (18) | 0.031 (2) | 0.0001 (18) |
C32 | 0.029 (2) | 0.027 (2) | 0.072 (3) | −0.0032 (17) | 0.024 (2) | −0.009 (2) |
C33 | 0.0216 (19) | 0.0213 (19) | 0.066 (3) | −0.0018 (15) | 0.0167 (19) | −0.0153 (19) |
C34 | 0.0162 (17) | 0.0188 (18) | 0.040 (2) | 0.0037 (14) | 0.0079 (15) | −0.0161 (15) |
C35 | 0.0164 (17) | 0.0249 (19) | 0.0284 (18) | 0.0053 (14) | 0.0024 (14) | −0.0148 (14) |
C36 | 0.0177 (17) | 0.034 (2) | 0.039 (2) | 0.0061 (15) | −0.0006 (15) | −0.0231 (18) |
C37 | 0.027 (2) | 0.054 (3) | 0.0269 (19) | 0.0171 (19) | −0.0075 (15) | −0.0204 (19) |
C38 | 0.041 (2) | 0.044 (2) | 0.0229 (19) | 0.0173 (19) | 0.0004 (17) | −0.0114 (17) |
C39 | 0.0271 (19) | 0.030 (2) | 0.0169 (17) | 0.0104 (15) | 0.0008 (14) | −0.0057 (14) |
C40 | 0.0222 (16) | 0.0220 (18) | 0.0169 (15) | 0.0043 (14) | 0.0068 (12) | −0.0026 (14) |
C41 | 0.0307 (18) | 0.0258 (19) | 0.0156 (15) | 0.0019 (15) | 0.0052 (13) | −0.0035 (14) |
C42 | 0.0233 (17) | 0.0255 (19) | 0.0165 (16) | 0.0014 (14) | −0.0003 (13) | 0.0027 (13) |
C43 | 0.0140 (16) | 0.0187 (17) | 0.0230 (17) | 0.0014 (13) | 0.0041 (13) | −0.0021 (13) |
C44 | 0.0142 (16) | 0.0132 (16) | 0.0160 (15) | −0.0042 (12) | 0.0031 (12) | −0.0024 (12) |
C45 | 0.0143 (16) | 0.0116 (16) | 0.0152 (15) | −0.0029 (12) | 0.0041 (12) | 0.0013 (12) |
C46 | 0.0131 (16) | 0.0164 (17) | 0.0191 (16) | 0.0020 (13) | 0.0030 (13) | −0.0024 (13) |
C47 | 0.0186 (17) | 0.0244 (18) | 0.0214 (17) | 0.0070 (14) | 0.0079 (14) | −0.0053 (14) |
C48 | 0.0215 (17) | 0.0222 (18) | 0.0155 (16) | 0.0002 (14) | 0.0044 (13) | −0.0058 (13) |
C49 | 0.0185 (16) | 0.0192 (17) | 0.0162 (16) | −0.0007 (13) | 0.0011 (13) | −0.0004 (13) |
C51 | 0.0099 (14) | 0.0175 (16) | 0.0193 (16) | 0.0015 (12) | 0.0030 (12) | −0.0045 (12) |
C52 | 0.0124 (15) | 0.0196 (16) | 0.0143 (16) | 0.0025 (12) | 0.0016 (13) | 0.0028 (12) |
C53 | 0.0074 (14) | 0.0167 (16) | 0.0191 (15) | 0.0027 (11) | 0.0002 (12) | 0.0024 (12) |
C54 | 0.0145 (15) | 0.0143 (15) | 0.0175 (15) | −0.0006 (12) | −0.0002 (12) | −0.0012 (12) |
C55 | 0.0138 (15) | 0.0215 (17) | 0.0134 (15) | 0.0028 (12) | −0.0017 (12) | −0.0010 (12) |
C56 | 0.0116 (15) | 0.0192 (16) | 0.0202 (16) | 0.0008 (12) | 0.0033 (12) | 0.0022 (12) |
C57 | 0.0091 (15) | 0.0176 (18) | 0.0213 (17) | 0.0032 (12) | 0.0014 (13) | −0.0041 (13) |
C58 | 0.0124 (15) | 0.0212 (18) | 0.0182 (17) | −0.0021 (13) | −0.0014 (13) | 0.0032 (14) |
C59 | 0.0201 (16) | 0.0212 (17) | 0.0188 (16) | −0.0006 (13) | 0.0007 (13) | −0.0003 (13) |
C60 | 0.0222 (16) | 0.0196 (17) | 0.0165 (15) | −0.0032 (14) | 0.0055 (12) | −0.0043 (14) |
C61 | 0.0258 (17) | 0.0286 (19) | 0.0184 (15) | −0.0050 (15) | −0.0018 (13) | −0.0011 (15) |
C62 | 0.0219 (18) | 0.028 (2) | 0.0247 (18) | −0.0006 (14) | −0.0047 (14) | 0.0006 (14) |
C63 | 0.0164 (17) | 0.027 (2) | 0.0252 (18) | 0.0000 (14) | −0.0006 (14) | 0.0038 (15) |
C64 | 0.0162 (16) | 0.0128 (16) | 0.0204 (16) | −0.0031 (13) | 0.0079 (13) | 0.0033 (13) |
C65 | 0.0139 (16) | 0.0144 (16) | 0.0221 (17) | −0.0020 (13) | 0.0050 (13) | 0.0042 (13) |
C66 | 0.0170 (17) | 0.0247 (19) | 0.0245 (18) | 0.0049 (14) | 0.0071 (14) | 0.0044 (14) |
C67 | 0.034 (2) | 0.025 (2) | 0.0279 (19) | 0.0089 (16) | 0.0157 (16) | −0.0045 (15) |
C68 | 0.035 (2) | 0.0275 (19) | 0.0164 (17) | 0.0044 (16) | 0.0043 (15) | −0.0080 (14) |
C69 | 0.0194 (17) | 0.0214 (18) | 0.0174 (16) | 0.0010 (13) | 0.0022 (13) | 0.0003 (13) |
C70 | 0.0222 (17) | 0.0196 (18) | 0.0200 (16) | 0.0003 (13) | 0.0087 (13) | 0.0010 (13) |
C71 | 0.0245 (17) | 0.0279 (19) | 0.0165 (16) | 0.0054 (14) | 0.0034 (13) | 0.0022 (14) |
C72 | 0.0176 (15) | 0.0278 (19) | 0.0187 (15) | 0.0062 (14) | −0.0017 (12) | −0.0062 (14) |
C73 | 0.0189 (17) | 0.0234 (18) | 0.0196 (17) | 0.0020 (14) | 0.0042 (13) | −0.0058 (14) |
C74 | 0.0131 (15) | 0.0153 (16) | 0.0182 (16) | 0.0015 (12) | 0.0037 (12) | −0.0067 (12) |
C75 | 0.0151 (16) | 0.0182 (17) | 0.0142 (15) | −0.0009 (13) | 0.0048 (12) | −0.0057 (13) |
C76 | 0.0160 (17) | 0.0258 (19) | 0.0246 (18) | −0.0046 (14) | 0.0053 (14) | −0.0013 (15) |
C77 | 0.0240 (19) | 0.030 (2) | 0.0278 (19) | −0.0049 (15) | 0.0112 (15) | 0.0023 (15) |
C78 | 0.0273 (18) | 0.0271 (19) | 0.0178 (17) | 0.0004 (15) | 0.0067 (14) | −0.0005 (14) |
C79 | 0.0188 (17) | 0.0255 (18) | 0.0123 (15) | 0.0033 (13) | 0.0026 (13) | −0.0028 (13) |
C80 | 0.038 (2) | 0.0184 (18) | 0.0267 (19) | −0.0058 (15) | 0.0115 (16) | −0.0012 (14) |
C81 | 0.056 (3) | 0.025 (2) | 0.048 (2) | −0.0038 (19) | 0.031 (2) | −0.0028 (18) |
C82 | 0.056 (3) | 0.025 (2) | 0.057 (3) | 0.0088 (19) | 0.036 (2) | 0.0039 (19) |
C83 | 0.026 (2) | 0.035 (2) | 0.059 (3) | 0.0102 (17) | 0.0206 (19) | 0.023 (2) |
C84 | 0.0232 (18) | 0.0238 (19) | 0.034 (2) | −0.0031 (14) | 0.0109 (15) | 0.0145 (15) |
C85 | 0.0151 (17) | 0.034 (2) | 0.032 (2) | −0.0070 (15) | 0.0038 (15) | 0.0205 (17) |
C86 | 0.023 (2) | 0.055 (3) | 0.037 (2) | −0.0095 (18) | 0.0024 (17) | 0.026 (2) |
C87 | 0.029 (2) | 0.074 (3) | 0.046 (3) | −0.025 (2) | −0.0123 (19) | 0.038 (2) |
C88 | 0.050 (3) | 0.060 (3) | 0.0224 (18) | −0.030 (2) | −0.0036 (17) | 0.0150 (19) |
C89 | 0.037 (2) | 0.040 (2) | 0.0225 (18) | −0.0148 (18) | −0.0006 (15) | 0.0078 (17) |
C90 | 0.0197 (17) | 0.0225 (18) | 0.0167 (16) | 0.0016 (14) | 0.0019 (13) | −0.0003 (13) |
C91 | 0.0231 (18) | 0.033 (2) | 0.0157 (16) | 0.0005 (15) | 0.0033 (14) | 0.0064 (14) |
C92 | 0.0221 (18) | 0.0255 (19) | 0.0215 (17) | −0.0059 (14) | 0.0103 (14) | 0.0051 (14) |
C93 | 0.0124 (16) | 0.0223 (18) | 0.0177 (16) | −0.0019 (13) | 0.0034 (13) | −0.0004 (13) |
C94 | 0.0176 (16) | 0.0174 (17) | 0.0158 (16) | 0.0025 (13) | 0.0015 (13) | −0.0004 (13) |
C95 | 0.0163 (16) | 0.0161 (16) | 0.0148 (15) | 0.0000 (13) | 0.0058 (13) | −0.0002 (12) |
C96 | 0.0165 (16) | 0.0191 (17) | 0.0196 (16) | −0.0004 (13) | 0.0024 (13) | 0.0019 (13) |
C97 | 0.0196 (17) | 0.029 (2) | 0.0206 (17) | −0.0017 (14) | −0.0027 (13) | −0.0017 (14) |
C98 | 0.0279 (17) | 0.029 (2) | 0.0151 (15) | −0.0020 (15) | −0.0006 (13) | 0.0070 (14) |
C99 | 0.0218 (16) | 0.0262 (19) | 0.0196 (15) | −0.0019 (14) | 0.0078 (13) | 0.0062 (14) |
C101 | 0.0213 (17) | 0.0219 (17) | 0.0106 (14) | −0.0050 (13) | 0.0007 (12) | 0.0023 (12) |
C102 | 0.0212 (17) | 0.0197 (17) | 0.0107 (15) | −0.0027 (13) | −0.0008 (12) | 0.0010 (12) |
C103 | 0.0280 (18) | 0.0206 (17) | 0.0058 (14) | −0.0028 (13) | 0.0003 (12) | 0.0017 (12) |
C104 | 0.0252 (18) | 0.0214 (17) | 0.0118 (15) | −0.0073 (14) | 0.0037 (13) | −0.0006 (12) |
C105 | 0.0209 (16) | 0.0239 (17) | 0.0098 (14) | −0.0013 (13) | 0.0037 (12) | 0.0016 (12) |
C106 | 0.0286 (18) | 0.0182 (16) | 0.0092 (14) | −0.0052 (13) | 0.0006 (12) | 0.0008 (11) |
C107 | 0.0213 (17) | 0.0221 (18) | 0.0143 (16) | −0.0055 (14) | −0.0041 (13) | 0.0027 (13) |
C108 | 0.0279 (19) | 0.0237 (18) | 0.0133 (16) | −0.0089 (15) | 0.0066 (14) | 0.0017 (13) |
C109 | 0.0278 (18) | 0.0219 (18) | 0.0121 (15) | −0.0038 (14) | 0.0029 (13) | 0.0001 (12) |
C111 | 0.0300 (19) | 0.0223 (18) | 0.0192 (17) | −0.0068 (14) | 0.0013 (14) | −0.0021 (13) |
C112 | 0.0322 (19) | 0.0173 (17) | 0.0139 (16) | 0.0008 (14) | −0.0012 (14) | 0.0001 (12) |
C113 | 0.0313 (19) | 0.0224 (18) | 0.0193 (17) | −0.0021 (15) | −0.0022 (14) | −0.0013 (13) |
C114 | 0.0294 (19) | 0.0185 (18) | 0.034 (2) | 0.0030 (15) | −0.0095 (16) | −0.0018 (15) |
C115 | 0.043 (2) | 0.0178 (18) | 0.039 (2) | −0.0045 (16) | −0.0150 (18) | 0.0059 (16) |
C116 | 0.031 (2) | 0.028 (2) | 0.037 (2) | −0.0125 (16) | −0.0037 (17) | 0.0036 (16) |
C117 | 0.035 (2) | 0.0235 (19) | 0.0208 (17) | −0.0075 (16) | 0.0055 (15) | −0.0044 (14) |
C118 | 0.033 (2) | 0.0253 (19) | 0.0143 (16) | 0.0077 (16) | 0.0003 (14) | −0.0040 (14) |
C119 | 0.043 (3) | 0.033 (2) | 0.079 (3) | 0.000 (2) | −0.018 (2) | 0.021 (2) |
C121 | 0.044 (2) | 0.054 (3) | 0.0213 (19) | −0.010 (2) | 0.0064 (17) | 0.0076 (17) |
C122 | 0.044 (2) | 0.040 (2) | 0.0235 (19) | 0.0019 (19) | −0.0038 (17) | 0.0035 (17) |
C123 | 0.027 (2) | 0.033 (2) | 0.036 (2) | 0.0006 (16) | 0.0014 (16) | 0.0020 (17) |
C124 | 0.0277 (19) | 0.026 (2) | 0.0294 (19) | 0.0030 (15) | 0.0090 (16) | 0.0014 (15) |
C125 | 0.0290 (19) | 0.0209 (18) | 0.0182 (17) | 0.0012 (14) | 0.0065 (14) | −0.0031 (13) |
C126 | 0.0308 (19) | 0.0167 (17) | 0.0177 (17) | 0.0031 (14) | 0.0075 (15) | −0.0051 (13) |
C127 | 0.032 (2) | 0.0231 (19) | 0.031 (2) | −0.0033 (15) | 0.0067 (16) | 0.0053 (15) |
C128 | 0.029 (2) | 0.034 (2) | 0.040 (2) | −0.0038 (16) | −0.0053 (17) | 0.0027 (17) |
C129 | 0.045 (2) | 0.032 (2) | 0.029 (2) | 0.0045 (18) | −0.0056 (17) | −0.0016 (16) |
C130 | 0.042 (2) | 0.040 (2) | 0.0217 (19) | 0.0005 (18) | 0.0077 (17) | 0.0059 (16) |
C131 | 0.038 (2) | 0.0200 (18) | 0.0296 (19) | 0.0021 (15) | 0.0016 (16) | −0.0039 (14) |
C132 | 0.035 (2) | 0.023 (2) | 0.038 (2) | 0.0021 (16) | −0.0086 (17) | −0.0001 (16) |
C133 | 0.0249 (19) | 0.024 (2) | 0.045 (2) | −0.0002 (15) | 0.0019 (17) | −0.0014 (17) |
C134 | 0.0237 (18) | 0.0209 (18) | 0.0297 (19) | 0.0032 (14) | 0.0035 (15) | −0.0004 (14) |
C135 | 0.0253 (17) | 0.0103 (16) | 0.0257 (18) | −0.0025 (13) | 0.0087 (15) | 0.0041 (13) |
C136 | 0.0207 (17) | 0.0181 (17) | 0.0228 (17) | −0.0013 (13) | 0.0094 (14) | 0.0059 (13) |
C137 | 0.0280 (19) | 0.0222 (19) | 0.0295 (19) | 0.0023 (15) | 0.0040 (16) | −0.0077 (15) |
C138 | 0.0268 (19) | 0.031 (2) | 0.036 (2) | 0.0073 (16) | 0.0027 (16) | −0.0016 (16) |
C139 | 0.036 (2) | 0.040 (2) | 0.0224 (18) | 0.0062 (17) | −0.0002 (16) | 0.0022 (16) |
C140 | 0.043 (2) | 0.038 (2) | 0.0191 (18) | 0.0087 (18) | 0.0073 (16) | −0.0032 (15) |
O74W | 0.0464 (18) | 0.052 (2) | 0.0296 (14) | −0.0208 (15) | 0.0070 (13) | −0.0018 (14) |
O75W | 0.052 (2) | 0.052 (2) | 0.0281 (19) | −0.0023 (18) | 0.0150 (17) | 0.0097 (16) |
O76W | 0.086 (3) | 0.057 (2) | 0.060 (2) | 0.015 (2) | 0.016 (2) | −0.0009 (18) |
O77W | 0.131 (4) | 0.081 (3) | 0.0348 (19) | 0.018 (3) | 0.003 (2) | 0.0087 (19) |
O78W | 0.0385 (18) | 0.082 (3) | 0.055 (2) | 0.0281 (17) | −0.0011 (15) | −0.0207 (18) |
O79W | 0.0447 (18) | 0.0396 (17) | 0.0369 (16) | −0.0110 (14) | 0.0100 (13) | −0.0030 (13) |
O80W | 0.0329 (15) | 0.0383 (16) | 0.0360 (16) | −0.0142 (13) | −0.0038 (13) | 0.0110 (12) |
O81W | 0.0341 (16) | 0.0323 (15) | 0.0417 (16) | −0.0113 (12) | 0.0148 (12) | −0.0080 (12) |
O82W | 0.047 (2) | 0.0215 (16) | 0.0208 (16) | 0.0057 (14) | 0.0082 (14) | −0.0008 (12) |
O83W | 0.046 (2) | 0.0302 (19) | 0.0344 (19) | −0.0058 (15) | 0.0050 (16) | 0.0009 (15) |
O84W | 0.076 (2) | 0.0434 (19) | 0.0380 (17) | 0.0052 (17) | 0.0149 (16) | 0.0052 (14) |
O85W | 0.0243 (13) | 0.0348 (15) | 0.0298 (14) | −0.0044 (11) | 0.0066 (11) | 0.0041 (11) |
O86W | 0.0278 (14) | 0.0285 (14) | 0.0330 (14) | −0.0046 (10) | 0.0112 (11) | −0.0018 (11) |
O87W | 0.0288 (14) | 0.0471 (17) | 0.0363 (15) | 0.0039 (12) | 0.0082 (12) | 0.0198 (13) |
O88W | 0.0409 (17) | 0.056 (2) | 0.0364 (16) | −0.0109 (14) | 0.0119 (13) | 0.0012 (14) |
O89W | 0.0492 (17) | 0.0523 (19) | 0.0280 (15) | 0.0020 (15) | 0.0001 (13) | 0.0090 (13) |
O90W | 0.0528 (19) | 0.0460 (19) | 0.066 (2) | −0.0088 (16) | 0.0295 (17) | −0.0074 (16) |
O91W | 0.0362 (16) | 0.0374 (16) | 0.0331 (14) | −0.0107 (12) | −0.0024 (12) | −0.0003 (12) |
O92W | 0.0289 (14) | 0.0291 (14) | 0.0348 (14) | −0.0035 (12) | 0.0107 (11) | −0.0086 (12) |
O93W | 0.0294 (14) | 0.0406 (16) | 0.0282 (14) | −0.0071 (12) | 0.0072 (11) | 0.0049 (12) |
O94W | 0.0515 (18) | 0.058 (2) | 0.0343 (16) | 0.0157 (16) | 0.0124 (14) | −0.0052 (14) |
O95W | 0.0461 (17) | 0.0419 (18) | 0.0387 (17) | 0.0065 (14) | 0.0084 (14) | −0.0027 (13) |
O96W | 0.068 (3) | 0.075 (3) | 0.063 (2) | 0.002 (2) | 0.0051 (19) | 0.0061 (19) |
O97W | 0.0291 (14) | 0.0279 (15) | 0.0335 (15) | 0.0012 (11) | 0.0030 (11) | −0.0036 (11) |
O98W | 0.0262 (14) | 0.0350 (15) | 0.0275 (14) | −0.0017 (12) | 0.0071 (11) | 0.0004 (11) |
O99W | 0.0298 (14) | 0.0338 (15) | 0.0298 (13) | 0.0040 (12) | 0.0023 (11) | 0.0028 (12) |
Cu1—N3 | 1.981 (2) | C55—C59 | 1.492 (4) |
Cu1—N1 | 1.982 (2) | C56—H56 | 0.9300 |
Cu1—N2 | 2.039 (3) | C60—C61 | 1.374 (4) |
Cu1—O1 | 2.043 (2) | C60—H60 | 0.9300 |
Cu1—N4 | 2.157 (3) | C61—C62 | 1.388 (5) |
Cu2—N7 | 1.970 (2) | C61—H61 | 0.9300 |
Cu2—O3 | 1.991 (2) | C62—C63 | 1.384 (5) |
Cu2—N6 | 1.998 (3) | C62—H62 | 0.9300 |
Cu2—N8 | 2.045 (2) | C63—C64 | 1.388 (5) |
Cu2—N5 | 2.149 (3) | C63—H63 | 0.9300 |
Cu3—N9 | 1.979 (2) | C64—C65 | 1.466 (4) |
Cu3—N11 | 1.982 (2) | C65—C66 | 1.390 (5) |
Cu3—O7 | 2.018 (2) | C66—C67 | 1.373 (5) |
Cu3—N10 | 2.047 (3) | C66—H66 | 0.9300 |
Cu3—N12 | 2.158 (3) | C67—C68 | 1.385 (5) |
Cu4—N16 | 1.966 (3) | C67—H67 | 0.9300 |
Cu4—N14 | 1.984 (3) | C68—C69 | 1.379 (5) |
Cu4—O9 | 1.987 (2) | C68—H68 | 0.9300 |
Cu4—N15 | 2.058 (3) | C69—H69 | 0.9300 |
Cu4—N13 | 2.161 (3) | C70—C71 | 1.375 (4) |
O1—C7 | 1.276 (4) | C70—H70 | 0.9300 |
O2—C7 | 1.256 (4) | C71—C72 | 1.384 (5) |
O3—C8 | 1.280 (4) | C71—H71 | 0.9300 |
O4—C8 | 1.243 (4) | C72—C73 | 1.376 (5) |
O5—C9 | 1.319 (4) | C72—H72 | 0.9300 |
O5—H5W | 0.87 (4) | C73—C74 | 1.383 (4) |
O6—C9 | 1.217 (4) | C73—H73 | 0.9300 |
O7—C57 | 1.279 (4) | C74—C75 | 1.491 (4) |
O8—C57 | 1.244 (4) | C75—C76 | 1.400 (5) |
O9—C58 | 1.267 (4) | C76—C77 | 1.378 (5) |
O10—C58 | 1.249 (4) | C76—H76 | 0.9300 |
O11—C59 | 1.296 (4) | C77—C78 | 1.380 (5) |
O11—H11V | 0.859 (19) | C77—H77 | 0.9300 |
O12—C59 | 1.208 (4) | C78—C79 | 1.384 (5) |
O13—C107 | 1.241 (4) | C78—H78 | 0.9300 |
O14—C107 | 1.280 (4) | C79—H79 | 0.9300 |
O15—C108 | 1.269 (4) | C80—C81 | 1.374 (5) |
O16—C108 | 1.251 (4) | C80—H80 | 0.9300 |
O17—C109 | 1.218 (4) | C81—C82 | 1.373 (6) |
O18—C109 | 1.298 (4) | C81—H81 | 0.9300 |
O18—H18V | 0.870 (19) | C82—C83 | 1.374 (6) |
O19—C117 | 1.258 (4) | C82—H82 | 0.9300 |
O20—C117 | 1.256 (4) | C83—C84 | 1.401 (5) |
O21—C118 | 1.236 (4) | C83—H83 | 0.9300 |
O22—C118 | 1.281 (4) | C84—C85 | 1.477 (5) |
O22—H22V | 0.86 (2) | C85—C86 | 1.396 (5) |
O23—C119 | 1.268 (6) | C86—C87 | 1.376 (7) |
O24—C119 | 1.235 (6) | C86—H86 | 0.9300 |
N1—C14 | 1.344 (4) | C87—C88 | 1.384 (7) |
N1—C10 | 1.345 (4) | C87—H87 | 0.9300 |
N2—C19 | 1.340 (4) | C88—C89 | 1.382 (5) |
N2—C15 | 1.361 (4) | C88—H88 | 0.9300 |
N3—C20 | 1.349 (4) | C89—H89 | 0.9300 |
N3—C24 | 1.353 (4) | C90—C91 | 1.378 (5) |
N4—C29 | 1.335 (4) | C90—H90 | 0.9300 |
N4—C25 | 1.336 (4) | C91—C92 | 1.390 (5) |
N5—C30 | 1.327 (5) | C91—H91 | 0.9300 |
N5—C34 | 1.363 (4) | C92—C93 | 1.385 (5) |
N6—C39 | 1.339 (4) | C92—H92 | 0.9300 |
N6—C35 | 1.346 (4) | C93—C94 | 1.380 (5) |
N7—C40 | 1.336 (4) | C93—H93 | 0.9300 |
N7—C44 | 1.357 (4) | C94—C95 | 1.475 (4) |
N8—C49 | 1.328 (4) | C95—C96 | 1.390 (4) |
N8—C45 | 1.361 (4) | C96—C97 | 1.381 (5) |
N9—C60 | 1.342 (4) | C96—H96 | 0.9300 |
N9—C64 | 1.353 (4) | C97—C98 | 1.381 (5) |
N10—C69 | 1.337 (4) | C97—H97 | 0.9300 |
N10—C65 | 1.353 (4) | C98—C99 | 1.386 (4) |
N11—C70 | 1.340 (4) | C98—H98 | 0.9300 |
N11—C74 | 1.350 (4) | C99—H99 | 0.9300 |
N12—C79 | 1.340 (4) | C101—C102 | 1.396 (4) |
N12—C75 | 1.346 (4) | C101—C106 | 1.397 (4) |
N13—C80 | 1.336 (5) | C101—C107 | 1.516 (4) |
N13—C84 | 1.346 (4) | C102—C103 | 1.389 (4) |
N14—C89 | 1.329 (5) | C102—H102 | 0.9300 |
N14—C85 | 1.353 (5) | C103—C104 | 1.387 (5) |
N15—C90 | 1.332 (4) | C103—C108 | 1.503 (5) |
N15—C94 | 1.357 (4) | C104—C105 | 1.402 (5) |
N16—C99 | 1.342 (4) | C104—H104 | 0.9300 |
N16—C95 | 1.355 (4) | C105—C106 | 1.394 (4) |
N17—C121 | 1.340 (5) | C105—C109 | 1.490 (5) |
N17—C125 | 1.344 (4) | C106—H106 | 0.9300 |
N18—C130 | 1.327 (5) | C111—C112 | 1.392 (5) |
N18—C126 | 1.341 (4) | C111—C116 | 1.395 (5) |
N19—C131 | 1.337 (5) | C111—C117 | 1.499 (5) |
N19—C135 | 1.342 (4) | C112—C113 | 1.389 (5) |
N20—C140 | 1.342 (5) | C112—H112 | 0.9300 |
N20—C136 | 1.342 (4) | C113—C114 | 1.397 (5) |
C1—C6 | 1.385 (4) | C113—C118 | 1.490 (5) |
C1—C2 | 1.397 (4) | C114—C115 | 1.399 (5) |
C1—C7 | 1.507 (4) | C114—H114 | 0.9300 |
C2—C3 | 1.389 (4) | C115—C116 | 1.381 (5) |
C2—H2 | 0.9300 | C115—C119 | 1.525 (6) |
C3—C4 | 1.392 (4) | C116—H116 | 0.9300 |
C3—C8 | 1.513 (4) | C121—C122 | 1.375 (5) |
C4—C5 | 1.392 (4) | C121—H121 | 0.9300 |
C4—H4 | 0.9300 | C122—C123 | 1.382 (5) |
C5—C6 | 1.391 (4) | C122—H122 | 0.9300 |
C5—C9 | 1.492 (4) | C123—C124 | 1.375 (5) |
C6—H6 | 0.9300 | C123—H123 | 0.9300 |
C10—C11 | 1.379 (4) | C124—C125 | 1.380 (5) |
C10—H10 | 0.9300 | C124—H124 | 0.9300 |
C11—C12 | 1.384 (5) | C125—C126 | 1.493 (5) |
C11—H11 | 0.9300 | C126—C127 | 1.391 (5) |
C12—C13 | 1.384 (5) | C127—C128 | 1.385 (5) |
C12—H12 | 0.9300 | C127—H127 | 0.9300 |
C13—C14 | 1.394 (4) | C128—C129 | 1.375 (6) |
C13—H13 | 0.9300 | C128—H128 | 0.9300 |
C14—C15 | 1.475 (4) | C129—C130 | 1.382 (6) |
C15—C16 | 1.392 (5) | C129—H129 | 0.9300 |
C16—C17 | 1.382 (5) | C130—H130 | 0.9300 |
C16—H16 | 0.9300 | C131—C132 | 1.385 (5) |
C17—C18 | 1.373 (5) | C131—H131 | 0.9300 |
C17—H17 | 0.9300 | C132—C133 | 1.375 (5) |
C18—C19 | 1.402 (5) | C132—H132 | 0.9300 |
C18—H18 | 0.9300 | C133—C134 | 1.383 (5) |
C19—H19 | 0.9300 | C133—H133 | 0.9300 |
C20—C21 | 1.371 (4) | C134—C135 | 1.390 (5) |
C20—H20 | 0.9300 | C134—H134 | 0.9300 |
C21—C22 | 1.384 (5) | C135—C136 | 1.489 (5) |
C21—H21 | 0.9300 | C136—C137 | 1.388 (5) |
C22—C23 | 1.377 (5) | C137—C138 | 1.373 (5) |
C22—H22 | 0.9300 | C137—H137 | 0.9300 |
C23—C24 | 1.394 (4) | C138—C139 | 1.377 (5) |
C23—H23 | 0.9300 | C138—H138 | 0.9300 |
C24—C25 | 1.481 (4) | C139—C140 | 1.373 (5) |
C25—C26 | 1.400 (4) | C139—H139 | 0.9300 |
C26—C27 | 1.388 (5) | C140—H140 | 0.9300 |
C26—H26 | 0.9300 | O74W—H74V | 0.83 (2) |
C27—C28 | 1.372 (5) | O74W—H74W | 0.845 (19) |
C27—H27 | 0.9300 | O75W—O75V | 1.376 (19) |
C28—C29 | 1.386 (5) | O76W—H76W | 0.93 (5) |
C28—H28 | 0.9300 | O76W—H76V | 0.93 (5) |
C29—H29 | 0.9300 | O77W—H77W | 0.919 (19) |
C30—C31 | 1.410 (5) | O77W—H77V | 0.887 (19) |
C30—H30 | 0.9300 | O78W—H78W | 0.846 (19) |
C31—C32 | 1.363 (6) | O78W—H78V | 0.860 (17) |
C31—H31 | 0.9300 | O79W—H79W | 0.948 (19) |
C32—C33 | 1.363 (6) | O79W—H79V | 0.87 (4) |
C32—H32 | 0.9300 | O80W—H80V | 0.83 (4) |
C33—C34 | 1.397 (5) | O80W—H80W | 0.885 (19) |
C33—H33 | 0.9300 | O81W—H81W | 0.85 (4) |
C34—C35 | 1.473 (5) | O81W—H81V | 0.825 (19) |
C35—C36 | 1.392 (5) | O82W—O82V | 1.785 (14) |
C36—C37 | 1.380 (6) | O83W—O83V | 1.229 (14) |
C36—H36 | 0.9300 | O83V—O96W | 1.596 (14) |
C37—C38 | 1.367 (6) | O84W—H84W | 0.94 (4) |
C37—H37 | 0.9300 | O84W—H84V | 0.90 (2) |
C38—C39 | 1.386 (5) | O85W—H85W | 0.85 (4) |
C38—H38 | 0.9300 | O85W—H85V | 0.847 (19) |
C39—H39 | 0.9300 | O86W—H86W | 0.82 (4) |
C40—C41 | 1.376 (4) | O86W—H86V | 0.834 (19) |
C40—H40 | 0.9300 | O87W—H87V | 0.85 (4) |
C41—C42 | 1.388 (5) | O87W—H87W | 0.838 (19) |
C41—H41 | 0.9300 | O88W—H88W | 0.90 (2) |
C42—C43 | 1.385 (5) | O88W—H88V | 0.87 (4) |
C42—H42 | 0.9300 | O89W—H89V | 0.88 (2) |
C43—C44 | 1.389 (4) | O89W—H89W | 0.909 (19) |
C43—H43 | 0.9300 | O90W—H90W | 0.918 (18) |
C44—C45 | 1.481 (4) | O90W—H90V | 0.912 (16) |
C45—C46 | 1.386 (4) | O91W—H91V | 0.863 (19) |
C46—C47 | 1.391 (4) | O91W—H91W | 0.87 (4) |
C46—H46 | 0.9300 | O92W—H92W | 0.862 (19) |
C47—C48 | 1.378 (5) | O92W—H92V | 0.829 (19) |
C47—H47 | 0.9300 | O93W—H93V | 0.843 (19) |
C48—C49 | 1.381 (4) | O93W—H93W | 0.84 (4) |
C48—H48 | 0.9300 | O94W—H94W | 0.88 (4) |
C49—H49 | 0.9300 | O94W—H94V | 0.884 (18) |
C51—C56 | 1.388 (4) | O95W—H95W | 0.85 (4) |
C51—C52 | 1.405 (4) | O95W—H95V | 0.88 (2) |
C51—C57 | 1.510 (4) | O96W—H96W | 0.96 (5) |
C52—C53 | 1.391 (4) | O97W—H97V | 0.86 (4) |
C52—H52 | 0.9300 | O97W—H97W | 0.879 (19) |
C53—C54 | 1.396 (4) | O98W—H98W | 0.823 (19) |
C53—C58 | 1.515 (4) | O98W—H98V | 0.819 (19) |
C54—C55 | 1.389 (4) | O99W—H99W | 0.847 (19) |
C54—H54 | 0.9300 | O99W—H99V | 0.851 (19) |
C55—C56 | 1.394 (4) | ||
N3—Cu1—N1 | 176.92 (12) | O8—C57—C51 | 120.3 (3) |
N3—Cu1—N2 | 96.37 (10) | O7—C57—C51 | 115.6 (3) |
N1—Cu1—N2 | 81.06 (11) | O10—C58—O9 | 125.3 (3) |
N3—Cu1—O1 | 94.62 (9) | O10—C58—C53 | 119.9 (3) |
N1—Cu1—O1 | 88.45 (10) | O9—C58—C53 | 114.7 (3) |
N2—Cu1—O1 | 148.02 (9) | O12—C59—O11 | 124.0 (3) |
N3—Cu1—N4 | 79.80 (10) | O12—C59—C55 | 122.1 (3) |
N1—Cu1—N4 | 99.58 (10) | O11—C59—C55 | 113.9 (3) |
N2—Cu1—N4 | 112.84 (10) | N9—C60—C61 | 121.8 (3) |
O1—Cu1—N4 | 98.61 (9) | N9—C60—H60 | 119.1 |
N7—Cu2—O3 | 90.17 (10) | C61—C60—H60 | 119.1 |
N7—Cu2—N6 | 177.44 (10) | C60—C61—C62 | 119.1 (3) |
O3—Cu2—N6 | 92.00 (10) | C60—C61—H61 | 120.4 |
N7—Cu2—N8 | 81.53 (10) | C62—C61—H61 | 120.4 |
O3—Cu2—N8 | 151.22 (10) | C63—C62—C61 | 119.3 (3) |
N6—Cu2—N8 | 95.91 (10) | C63—C62—H62 | 120.3 |
N7—Cu2—N5 | 101.33 (11) | C61—C62—H62 | 120.3 |
O3—Cu2—N5 | 99.90 (10) | C62—C63—C64 | 119.0 (3) |
N6—Cu2—N5 | 79.64 (11) | C62—C63—H63 | 120.5 |
N8—Cu2—N5 | 108.73 (10) | C64—C63—H63 | 120.5 |
N9—Cu3—N11 | 175.57 (12) | N9—C64—C63 | 121.0 (3) |
N9—Cu3—O7 | 90.30 (10) | N9—C64—C65 | 115.2 (3) |
N11—Cu3—O7 | 94.10 (10) | C63—C64—C65 | 123.7 (3) |
N9—Cu3—N10 | 81.01 (10) | N10—C65—C66 | 121.0 (3) |
N11—Cu3—N10 | 95.50 (10) | N10—C65—C64 | 115.1 (3) |
O7—Cu3—N10 | 148.03 (10) | C66—C65—C64 | 123.9 (3) |
N9—Cu3—N12 | 98.81 (10) | C67—C66—C65 | 119.6 (3) |
N11—Cu3—N12 | 79.91 (10) | C67—C66—H66 | 120.2 |
O7—Cu3—N12 | 99.73 (9) | C65—C66—H66 | 120.2 |
N10—Cu3—N12 | 111.96 (10) | C66—C67—C68 | 119.2 (3) |
N16—Cu4—N14 | 175.50 (13) | C66—C67—H67 | 120.4 |
N16—Cu4—O9 | 91.86 (10) | C68—C67—H67 | 120.4 |
N14—Cu4—O9 | 92.44 (10) | C69—C68—C67 | 118.7 (3) |
N16—Cu4—N15 | 81.11 (10) | C69—C68—H68 | 120.7 |
N14—Cu4—N15 | 95.88 (10) | C67—C68—H68 | 120.7 |
O9—Cu4—N15 | 148.13 (10) | N10—C69—C68 | 122.6 (3) |
N16—Cu4—N13 | 98.51 (11) | N10—C69—H69 | 118.7 |
N14—Cu4—N13 | 79.27 (11) | C68—C69—H69 | 118.7 |
O9—Cu4—N13 | 102.30 (10) | N11—C70—C71 | 122.7 (3) |
N15—Cu4—N13 | 109.46 (11) | N11—C70—H70 | 118.7 |
C7—O1—Cu1 | 108.67 (18) | C71—C70—H70 | 118.7 |
C8—O3—Cu2 | 119.78 (19) | C70—C71—C72 | 118.3 (3) |
C9—O5—H5W | 119 (3) | C70—C71—H71 | 120.8 |
C57—O7—Cu3 | 113.90 (19) | C72—C71—H71 | 120.8 |
C58—O9—Cu4 | 120.0 (2) | C73—C72—C71 | 119.5 (3) |
C59—O11—H11V | 111 (3) | C73—C72—H72 | 120.2 |
C109—O18—H18V | 115 (3) | C71—C72—H72 | 120.2 |
C118—O22—H22V | 107 (4) | C72—C73—C74 | 119.3 (3) |
C14—N1—C10 | 119.4 (3) | C72—C73—H73 | 120.3 |
C14—N1—Cu1 | 115.8 (2) | C74—C73—H73 | 120.3 |
C10—N1—Cu1 | 124.8 (2) | N11—C74—C73 | 121.2 (3) |
C19—N2—C15 | 119.4 (3) | N11—C74—C75 | 115.4 (3) |
C19—N2—Cu1 | 127.2 (2) | C73—C74—C75 | 123.4 (3) |
C15—N2—Cu1 | 113.4 (2) | N12—C75—C76 | 121.1 (3) |
C20—N3—C24 | 118.8 (3) | N12—C75—C74 | 116.0 (3) |
C20—N3—Cu1 | 124.3 (2) | C76—C75—C74 | 122.9 (3) |
C24—N3—Cu1 | 116.8 (2) | C77—C76—C75 | 118.9 (3) |
C29—N4—C25 | 118.9 (3) | C77—C76—H76 | 120.6 |
C29—N4—Cu1 | 129.2 (2) | C75—C76—H76 | 120.6 |
C25—N4—Cu1 | 111.3 (2) | C76—C77—C78 | 119.8 (3) |
C30—N5—C34 | 118.5 (3) | C76—C77—H77 | 120.1 |
C30—N5—Cu2 | 130.1 (2) | C78—C77—H77 | 120.1 |
C34—N5—Cu2 | 111.4 (2) | C77—C78—C79 | 118.4 (3) |
C39—N6—C35 | 119.4 (3) | C77—C78—H78 | 120.8 |
C39—N6—Cu2 | 123.5 (2) | C79—C78—H78 | 120.8 |
C35—N6—Cu2 | 117.0 (2) | N12—C79—C78 | 122.6 (3) |
C40—N7—C44 | 119.3 (3) | N12—C79—H79 | 118.7 |
C40—N7—Cu2 | 124.9 (2) | C78—C79—H79 | 118.7 |
C44—N7—Cu2 | 115.73 (19) | N13—C80—C81 | 123.0 (4) |
C49—N8—C45 | 118.2 (3) | N13—C80—H80 | 118.5 |
C49—N8—Cu2 | 128.6 (2) | C81—C80—H80 | 118.5 |
C45—N8—Cu2 | 113.0 (2) | C82—C81—C80 | 118.5 (4) |
C60—N9—C64 | 119.7 (3) | C82—C81—H81 | 120.7 |
C60—N9—Cu3 | 124.8 (2) | C80—C81—H81 | 120.7 |
C64—N9—Cu3 | 115.5 (2) | C81—C82—C83 | 119.8 (4) |
C69—N10—C65 | 118.9 (3) | C81—C82—H82 | 120.1 |
C69—N10—Cu3 | 127.8 (2) | C83—C82—H82 | 120.1 |
C65—N10—Cu3 | 113.2 (2) | C82—C83—C84 | 118.7 (4) |
C70—N11—C74 | 118.9 (3) | C82—C83—H83 | 120.6 |
C70—N11—Cu3 | 123.9 (2) | C84—C83—H83 | 120.6 |
C74—N11—Cu3 | 117.1 (2) | N13—C84—C83 | 121.2 (4) |
C79—N12—C75 | 119.2 (3) | N13—C84—C85 | 114.7 (3) |
C79—N12—Cu3 | 129.3 (2) | C83—C84—C85 | 124.1 (3) |
C75—N12—Cu3 | 111.0 (2) | N14—C85—C86 | 120.2 (4) |
C80—N13—C84 | 118.7 (3) | N14—C85—C84 | 116.6 (3) |
C80—N13—Cu4 | 128.9 (2) | C86—C85—C84 | 123.2 (4) |
C84—N13—Cu4 | 112.4 (2) | C87—C86—C85 | 119.1 (4) |
C89—N14—C85 | 120.3 (3) | C87—C86—H86 | 120.4 |
C89—N14—Cu4 | 122.8 (3) | C85—C86—H86 | 120.4 |
C85—N14—Cu4 | 116.9 (2) | C86—C87—C88 | 120.0 (4) |
C90—N15—C94 | 118.5 (3) | C86—C87—H87 | 120.0 |
C90—N15—Cu4 | 128.5 (2) | C88—C87—H87 | 120.0 |
C94—N15—Cu4 | 112.9 (2) | C89—C88—C87 | 118.2 (4) |
C99—N16—C95 | 119.4 (3) | C89—C88—H88 | 120.9 |
C99—N16—Cu4 | 124.6 (2) | C87—C88—H88 | 120.9 |
C95—N16—Cu4 | 116.0 (2) | N14—C89—C88 | 122.2 (4) |
C121—N17—C125 | 117.2 (3) | N14—C89—H89 | 118.9 |
C130—N18—C126 | 117.3 (3) | C88—C89—H89 | 118.9 |
C131—N19—C135 | 117.2 (3) | N15—C90—C91 | 123.3 (3) |
C140—N20—C136 | 117.4 (3) | N15—C90—H90 | 118.4 |
C6—C1—C2 | 119.6 (3) | C91—C90—H90 | 118.4 |
C6—C1—C7 | 120.6 (3) | C90—C91—C92 | 118.6 (3) |
C2—C1—C7 | 119.8 (3) | C90—C91—H91 | 120.7 |
C3—C2—C1 | 120.5 (3) | C92—C91—H91 | 120.7 |
C3—C2—H2 | 119.7 | C93—C92—C91 | 118.4 (3) |
C1—C2—H2 | 119.7 | C93—C92—H92 | 120.8 |
C2—C3—C4 | 119.1 (3) | C91—C92—H92 | 120.8 |
C2—C3—C8 | 120.8 (3) | C94—C93—C92 | 120.0 (3) |
C4—C3—C8 | 120.0 (3) | C94—C93—H93 | 120.0 |
C3—C4—C5 | 120.8 (3) | C92—C93—H93 | 120.0 |
C3—C4—H4 | 119.6 | N15—C94—C93 | 121.2 (3) |
C5—C4—H4 | 119.6 | N15—C94—C95 | 114.8 (3) |
C6—C5—C4 | 119.3 (3) | C93—C94—C95 | 124.0 (3) |
C6—C5—C9 | 119.9 (3) | N16—C95—C96 | 120.8 (3) |
C4—C5—C9 | 120.6 (3) | N16—C95—C94 | 115.0 (3) |
C1—C6—C5 | 120.5 (3) | C96—C95—C94 | 124.3 (3) |
C1—C6—H6 | 119.7 | C97—C96—C95 | 119.4 (3) |
C5—C6—H6 | 119.7 | C97—C96—H96 | 120.3 |
O2—C7—O1 | 123.6 (3) | C95—C96—H96 | 120.3 |
O2—C7—C1 | 119.4 (3) | C98—C97—C96 | 119.7 (3) |
O1—C7—C1 | 116.9 (3) | C98—C97—H97 | 120.1 |
O4—C8—O3 | 124.9 (3) | C96—C97—H97 | 120.1 |
O4—C8—C3 | 121.5 (3) | C97—C98—C99 | 118.4 (3) |
O3—C8—C3 | 113.6 (3) | C97—C98—H98 | 120.8 |
O6—C9—O5 | 124.8 (3) | C99—C98—H98 | 120.8 |
O6—C9—C5 | 122.5 (3) | N16—C99—C98 | 122.4 (3) |
O5—C9—C5 | 112.7 (3) | N16—C99—H99 | 118.8 |
N1—C10—C11 | 122.0 (3) | C98—C99—H99 | 118.8 |
N1—C10—H10 | 119.0 | C102—C101—C106 | 120.0 (3) |
C11—C10—H10 | 119.0 | C102—C101—C107 | 119.0 (3) |
C10—C11—C12 | 118.8 (3) | C106—C101—C107 | 121.0 (3) |
C10—C11—H11 | 120.6 | C103—C102—C101 | 121.1 (3) |
C12—C11—H11 | 120.6 | C103—C102—H102 | 119.5 |
C13—C12—C11 | 119.8 (3) | C101—C102—H102 | 119.5 |
C13—C12—H12 | 120.1 | C104—C103—C102 | 118.6 (3) |
C11—C12—H12 | 120.1 | C104—C103—C108 | 120.2 (3) |
C12—C13—C14 | 118.4 (3) | C102—C103—C108 | 121.2 (3) |
C12—C13—H13 | 120.8 | C103—C104—C105 | 121.4 (3) |
C14—C13—H13 | 120.8 | C103—C104—H104 | 119.3 |
N1—C14—C13 | 121.6 (3) | C105—C104—H104 | 119.3 |
N1—C14—C15 | 115.0 (3) | C106—C105—C104 | 119.6 (3) |
C13—C14—C15 | 123.4 (3) | C106—C105—C109 | 122.3 (3) |
N2—C15—C16 | 121.1 (3) | C104—C105—C109 | 118.1 (3) |
N2—C15—C14 | 114.8 (3) | C105—C106—C101 | 119.4 (3) |
C16—C15—C14 | 124.2 (3) | C105—C106—H106 | 120.3 |
C17—C16—C15 | 119.3 (3) | C101—C106—H106 | 120.3 |
C17—C16—H16 | 120.4 | O13—C107—O14 | 124.1 (3) |
C15—C16—H16 | 120.4 | O13—C107—C101 | 119.4 (3) |
C18—C17—C16 | 119.7 (3) | O14—C107—C101 | 116.5 (3) |
C18—C17—H17 | 120.2 | O16—C108—O15 | 125.2 (3) |
C16—C17—H17 | 120.2 | O16—C108—C103 | 117.5 (3) |
C17—C18—C19 | 119.0 (3) | O15—C108—C103 | 117.3 (3) |
C17—C18—H18 | 120.5 | O17—C109—O18 | 123.3 (3) |
C19—C18—H18 | 120.5 | O17—C109—C105 | 121.9 (3) |
N2—C19—C18 | 121.5 (3) | O18—C109—C105 | 114.9 (3) |
N2—C19—H19 | 119.2 | C112—C111—C116 | 119.7 (3) |
C18—C19—H19 | 119.2 | C112—C111—C117 | 122.0 (3) |
N3—C20—C21 | 122.7 (3) | C116—C111—C117 | 118.3 (3) |
N3—C20—H20 | 118.7 | C113—C112—C111 | 120.3 (3) |
C21—C20—H20 | 118.7 | C113—C112—H112 | 119.9 |
C20—C21—C22 | 118.8 (3) | C111—C112—H112 | 119.9 |
C20—C21—H21 | 120.6 | C112—C113—C114 | 119.3 (3) |
C22—C21—H21 | 120.6 | C112—C113—C118 | 121.4 (3) |
C23—C22—C21 | 119.3 (3) | C114—C113—C118 | 119.3 (3) |
C23—C22—H22 | 120.4 | C113—C114—C115 | 120.8 (3) |
C21—C22—H22 | 120.4 | C113—C114—H114 | 119.6 |
C22—C23—C24 | 119.6 (3) | C115—C114—H114 | 119.6 |
C22—C23—H23 | 120.2 | C116—C115—C114 | 119.1 (3) |
C24—C23—H23 | 120.2 | C116—C115—C119 | 118.9 (4) |
N3—C24—C23 | 120.8 (3) | C114—C115—C119 | 122.0 (4) |
N3—C24—C25 | 115.6 (3) | C115—C116—C111 | 120.8 (3) |
C23—C24—C25 | 123.7 (3) | C115—C116—H116 | 119.6 |
N4—C25—C26 | 121.7 (3) | C111—C116—H116 | 119.6 |
N4—C25—C24 | 116.1 (3) | O20—C117—O19 | 123.3 (3) |
C26—C25—C24 | 122.1 (3) | O20—C117—C111 | 117.9 (3) |
C27—C26—C25 | 118.6 (3) | O19—C117—C111 | 118.8 (3) |
C27—C26—H26 | 120.7 | O21—C118—O22 | 123.3 (3) |
C25—C26—H26 | 120.7 | O21—C118—C113 | 121.4 (3) |
C28—C27—C26 | 119.4 (3) | O22—C118—C113 | 115.3 (3) |
C28—C27—H27 | 120.3 | O24—C119—O23 | 124.8 (4) |
C26—C27—H27 | 120.3 | O24—C119—C115 | 116.0 (4) |
C27—C28—C29 | 118.5 (3) | O23—C119—C115 | 119.1 (4) |
C27—C28—H28 | 120.7 | N17—C121—C122 | 124.1 (4) |
C29—C28—H28 | 120.7 | N17—C121—H121 | 117.9 |
N4—C29—C28 | 122.9 (3) | C122—C121—H121 | 117.9 |
N4—C29—H29 | 118.6 | C121—C122—C123 | 117.9 (3) |
C28—C29—H29 | 118.6 | C121—C122—H122 | 121.0 |
N5—C30—C31 | 122.7 (4) | C123—C122—H122 | 121.0 |
N5—C30—H30 | 118.7 | C124—C123—C122 | 118.9 (4) |
C31—C30—H30 | 118.7 | C124—C123—H123 | 120.5 |
C32—C31—C30 | 117.7 (4) | C122—C123—H123 | 120.5 |
C32—C31—H31 | 121.1 | C123—C124—C125 | 119.6 (3) |
C30—C31—H31 | 121.1 | C123—C124—H124 | 120.2 |
C31—C32—C33 | 121.0 (4) | C125—C124—H124 | 120.2 |
C31—C32—H32 | 119.5 | N17—C125—C124 | 122.2 (3) |
C33—C32—H32 | 119.5 | N17—C125—C126 | 116.2 (3) |
C32—C33—C34 | 118.8 (4) | C124—C125—C126 | 121.5 (3) |
C32—C33—H33 | 120.6 | N18—C126—C127 | 122.4 (3) |
C34—C33—H33 | 120.6 | N18—C126—C125 | 116.4 (3) |
N5—C34—C33 | 121.3 (4) | C127—C126—C125 | 121.2 (3) |
N5—C34—C35 | 115.8 (3) | C128—C127—C126 | 118.8 (3) |
C33—C34—C35 | 122.9 (3) | C128—C127—H127 | 120.6 |
N6—C35—C36 | 121.1 (3) | C126—C127—H127 | 120.6 |
N6—C35—C34 | 116.0 (3) | C129—C128—C127 | 119.2 (4) |
C36—C35—C34 | 122.9 (3) | C129—C128—H128 | 120.4 |
C37—C36—C35 | 118.8 (4) | C127—C128—H128 | 120.4 |
C37—C36—H36 | 120.6 | C128—C129—C130 | 117.8 (4) |
C35—C36—H36 | 120.6 | C128—C129—H129 | 121.1 |
C38—C37—C36 | 120.1 (3) | C130—C129—H129 | 121.1 |
C38—C37—H37 | 120.0 | N18—C130—C129 | 124.4 (4) |
C36—C37—H37 | 120.0 | N18—C130—H130 | 117.8 |
C37—C38—C39 | 118.6 (4) | C129—C130—H130 | 117.8 |
C37—C38—H38 | 120.7 | N19—C131—C132 | 124.1 (3) |
C39—C38—H38 | 120.7 | N19—C131—H131 | 118.0 |
N6—C39—C38 | 122.1 (4) | C132—C131—H131 | 118.0 |
N6—C39—H39 | 118.9 | C133—C132—C131 | 118.1 (3) |
C38—C39—H39 | 118.9 | C133—C132—H132 | 120.9 |
N7—C40—C41 | 122.1 (3) | C131—C132—H132 | 120.9 |
N7—C40—H40 | 118.9 | C132—C133—C134 | 119.0 (3) |
C41—C40—H40 | 118.9 | C132—C133—H133 | 120.5 |
C40—C41—C42 | 119.1 (3) | C134—C133—H133 | 120.5 |
C40—C41—H41 | 120.4 | C133—C134—C135 | 119.1 (3) |
C42—C41—H41 | 120.4 | C133—C134—H134 | 120.4 |
C43—C42—C41 | 119.1 (3) | C135—C134—H134 | 120.4 |
C43—C42—H42 | 120.4 | N19—C135—C134 | 122.4 (3) |
C41—C42—H42 | 120.4 | N19—C135—C136 | 116.7 (3) |
C42—C43—C44 | 119.0 (3) | C134—C135—C136 | 120.9 (3) |
C42—C43—H43 | 120.5 | N20—C136—C137 | 121.8 (3) |
C44—C43—H43 | 120.5 | N20—C136—C135 | 116.7 (3) |
N7—C44—C43 | 121.2 (3) | C137—C136—C135 | 121.5 (3) |
N7—C44—C45 | 114.7 (3) | C138—C137—C136 | 119.8 (3) |
C43—C44—C45 | 124.1 (3) | C138—C137—H137 | 120.1 |
N8—C45—C46 | 121.8 (3) | C136—C137—H137 | 120.1 |
N8—C45—C44 | 114.9 (3) | C137—C138—C139 | 118.6 (3) |
C46—C45—C44 | 123.2 (3) | C137—C138—H138 | 120.7 |
C45—C46—C47 | 118.7 (3) | C139—C138—H138 | 120.7 |
C45—C46—H46 | 120.7 | C140—C139—C138 | 118.6 (3) |
C47—C46—H46 | 120.7 | C140—C139—H139 | 120.7 |
C48—C47—C46 | 119.5 (3) | C138—C139—H139 | 120.7 |
C48—C47—H47 | 120.3 | N20—C140—C139 | 123.7 (3) |
C46—C47—H47 | 120.3 | N20—C140—H140 | 118.1 |
C47—C48—C49 | 118.3 (3) | C139—C140—H140 | 118.1 |
C47—C48—H48 | 120.8 | H74V—O74W—H74W | 114 (5) |
C49—C48—H48 | 120.8 | H76W—O76W—H76V | 114 (6) |
N8—C49—C48 | 123.5 (3) | H77W—O77W—H77V | 83 (5) |
N8—C49—H49 | 118.2 | H78W—O78W—H78V | 121 (6) |
C48—C49—H49 | 118.2 | H79W—O79W—H79V | 119 (4) |
C56—C51—C52 | 119.5 (3) | H80V—O80W—H80W | 116 (5) |
C56—C51—C57 | 119.7 (3) | H81W—O81W—H81V | 102 (4) |
C52—C51—C57 | 120.7 (3) | O83W—O83V—O96W | 172.9 (12) |
C53—C52—C51 | 120.3 (3) | H84W—O84W—H84V | 72 (4) |
C53—C52—H52 | 119.9 | H85W—O85W—H85V | 99 (4) |
C51—C52—H52 | 119.9 | H86W—O86W—H86V | 103 (4) |
C52—C53—C54 | 119.5 (3) | H87V—O87W—H87W | 89 (4) |
C52—C53—C58 | 121.1 (3) | H88W—O88W—H88V | 108 (5) |
C54—C53—C58 | 119.2 (3) | H89V—O89W—H89W | 119 (4) |
C55—C54—C53 | 120.4 (3) | H90W—O90W—H90V | 99 (4) |
C55—C54—H54 | 119.8 | H91V—O91W—H91W | 101 (4) |
C53—C54—H54 | 119.8 | H92W—O92W—H92V | 110 (4) |
C54—C55—C56 | 119.9 (3) | H93V—O93W—H93W | 104 (4) |
C54—C55—C59 | 119.6 (3) | H94W—O94W—H94V | 65 (3) |
C56—C55—C59 | 120.6 (3) | H95W—O95W—H95V | 100 (4) |
C51—C56—C55 | 120.4 (3) | O83V—O96W—H96W | 121 (4) |
C51—C56—H56 | 119.8 | H97V—O97W—H97W | 104 (4) |
C55—C56—H56 | 119.8 | H98W—O98W—H98V | 102 (4) |
O8—C57—O7 | 124.0 (3) | H99W—O99W—H99V | 132 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5W···O85W | 0.87 (4) | 1.72 (2) | 2.565 (3) | 165 (4) |
O85W—H85V···O97W | 0.85 (2) | 1.87 (2) | 2.698 (4) | 164 (4) |
O85W—H85W···O93W | 0.85 (4) | 1.86 (2) | 2.707 (4) | 175 (4) |
O93W—H93V···O16 | 0.84 (2) | 1.92 (2) | 2.745 (3) | 166 (5) |
O93W—H93W···O87W | 0.84 (4) | 1.88 (2) | 2.710 (4) | 176 (5) |
O97W—H97V···O16 | 0.86 (4) | 1.88 (2) | 2.735 (3) | 171 (4) |
O97W—H97W···O74W | 0.88 (2) | 1.87 (2) | 2.733 (4) | 167 (4) |
O87W—H87W···O6 | 0.84 (2) | 2.03 (2) | 2.868 (4) | 177 (5) |
O87W—H87V···O13 | 0.85 (4) | 1.89 (2) | 2.734 (4) | 174 (5) |
O74W—H74V···O91W | 0.83 (2) | 1.96 (2) | 2.776 (4) | 170 (5) |
O74W—H74W···O83W | 0.85 (2) | 1.95 (3) | 2.696 (5) | 146 (5) |
O91W—H91V···O80W | 0.86 (2) | 1.89 (2) | 2.750 (4) | 176 (5) |
O91W—H91W···O79W | 0.87 (4) | 2.03 (2) | 2.882 (4) | 169 (4) |
O80W—H80V···O15 | 0.83 (4) | 2.03 (3) | 2.796 (3) | 154 (5) |
O80W—H80W···O81Wi | 0.89 (2) | 1.92 (2) | 2.788 (4) | 167 (4) |
O98W—H98V···O15 | 0.82 (2) | 1.97 (2) | 2.789 (3) | 176 (4) |
O98W—H98W···O81Wi | 0.82 (2) | 2.00 (3) | 2.753 (4) | 152 (4) |
O81W—H81W···O12 | 0.85 (4) | 1.98 (2) | 2.820 (4) | 170 (5) |
O81W—H81V···O92W | 0.83 (2) | 1.88 (2) | 2.692 (4) | 169 (5) |
O92W—H92W···O23 | 0.86 (2) | 1.91 (2) | 2.757 (4) | 169 (4) |
O92W—H92V···O99W | 0.83 (2) | 2.01 (2) | 2.801 (4) | 159 (4) |
O99W—H99W···O85W | 0.85 (2) | 1.93 (2) | 2.752 (4) | 164 (4) |
O99W—H99V···O96W | 0.85 (2) | 2.06 (3) | 2.845 (5) | 153 (4) |
O96W—H96W···O24 | 0.96 (5) | 1.75 (4) | 2.533 (6) | 137 (3) |
O22—H22V···O14ii | 0.86 (2) | 1.67 (2) | 2.518 (3) | 167 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C9H4O6)(C10H8N2)4](C9H4O6)·C10H8N2·13H2O |
Mr | 1558.45 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 120 |
a, b, c (Å) | 14.4638 (2), 19.7448 (2), 25.0638 (3) |
β (°) | 99.2051 (14) |
V (Å3) | 7065.66 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.3 × 0.3 × 0.25 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur2+ CCD diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.823, 0.840 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41227, 23598, 21012 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.086, 0.99 |
No. of reflections | 23591 |
No. of parameters | 2053 |
No. of restraints | 62 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.81, −0.62 |
Absolute structure | Flack (1983), 10782 Friedel pairs |
Absolute structure parameter | 0.105 (6) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5W···O85W | 0.87 (4) | 1.72 (2) | 2.565 (3) | 165 (4) |
O85W—H85V···O97W | 0.847 (19) | 1.87 (2) | 2.698 (4) | 164 (4) |
O85W—H85W···O93W | 0.85 (4) | 1.86 (2) | 2.707 (4) | 175 (4) |
O93W—H93V···O16 | 0.843 (19) | 1.92 (2) | 2.745 (3) | 166 (5) |
O93W—H93W···O87W | 0.84 (4) | 1.88 (2) | 2.710 (4) | 176 (5) |
O97W—H97V···O16 | 0.86 (4) | 1.88 (2) | 2.735 (3) | 171 (4) |
O97W—H97W···O74W | 0.879 (19) | 1.87 (2) | 2.733 (4) | 167 (4) |
O87W—H87W···O6 | 0.838 (19) | 2.03 (2) | 2.868 (4) | 177 (5) |
O87W—H87V···O13 | 0.85 (4) | 1.89 (2) | 2.734 (4) | 174 (5) |
O74W—H74V···O91W | 0.83 (2) | 1.96 (2) | 2.776 (4) | 170 (5) |
O74W—H74W···O83W | 0.845 (19) | 1.95 (3) | 2.696 (5) | 146 (5) |
O91W—H91V···O80W | 0.863 (19) | 1.89 (2) | 2.750 (4) | 176 (5) |
O91W—H91W···O79W | 0.87 (4) | 2.03 (2) | 2.882 (4) | 169 (4) |
O80W—H80V···O15 | 0.83 (4) | 2.03 (3) | 2.796 (3) | 154 (5) |
O80W—H80W···O81Wi | 0.885 (19) | 1.92 (2) | 2.788 (4) | 167 (4) |
O98W—H98V···O15 | 0.819 (19) | 1.97 (2) | 2.789 (3) | 176 (4) |
O98W—H98W···O81Wi | 0.823 (19) | 2.00 (3) | 2.753 (4) | 152 (4) |
O81W—H81W···O12 | 0.85 (4) | 1.98 (2) | 2.820 (4) | 170 (5) |
O81W—H81V···O92W | 0.825 (19) | 1.88 (2) | 2.692 (4) | 169 (5) |
O92W—H92W···O23 | 0.862 (19) | 1.91 (2) | 2.757 (4) | 169 (4) |
O92W—H92V···O99W | 0.829 (19) | 2.01 (2) | 2.801 (4) | 159 (4) |
O99W—H99W···O85W | 0.847 (19) | 1.93 (2) | 2.752 (4) | 164 (4) |
O99W—H99V···O96W | 0.851 (19) | 2.06 (3) | 2.845 (5) | 153 (4) |
O96W—H96W···O24 | 0.96 (5) | 1.75 (4) | 2.533 (6) | 137 (3) |
O22—H22V···O14ii | 0.86 (2) | 1.67 (2) | 2.518 (3) | 167 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z. |
Acknowledgements
Financial support of this work by the Ministry of Education, Youth and Sports of the Czech Republic (grant Nos. MSM6198959218 and MSM0021622415) is gratefully acknowledged.
References
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The structure of the title complex (Fig. 1) comprises two crystallographically independent dinuclear CuII dications, two 1,3,5-carbotricarboxylate dianions (Hbtc), two 2,2'-bipyridine (bpy) and 26 water molecules of crystallization. The two CuII metal centres are bridged by one Hbtc anion in which two carboxylato groups are coordinated to two copper atoms in a monodentate fashion. Each of the metal centres is bonded to four N atoms of two bpy ligands and one O atom of the Hbtc ligand in a highly distorted square-pyramidal geometry (τ = 0.48 for Cu1, τ = 0.44 for Cu2, τ = 0.46 for Cu3 and τ = 0.46 for Cu4). The Cu—N distances vary from 1.966 (3) to 2.161 (3) Å, while those of Cu—O range from 1.987 (2) to 2.043 (2) Å. The atoms forming the Cu2(btc) moiety deviate from planarity with dihedral angles between the bridging benzene ring and the peripheral 4-membered C–O–Cu–O rings being in the range 18.02 (8)° to 28.20 (8)° (Brandenburg, 2006). The distance between the two CuII cations is 10.4977 (5) Å for Cu1···Cu2, and 10.5670 (5) Å for Cu3···Cu4. For comparison, the Cu···Cu separations in recently published Cu-complexes involving the Cu2(btc) moiety with one uncoordinated carboxylato group that are included in the CSD (Cambridge Structural Database, Version 5.28.1; Allen, 2002) are 9.5245 (5) Å (Pech & Pickardt, 1988), 9.6328 (10) Å (Chui et al., 1999), 9.2316 (3) Å (Holmes et al., 2004), 8.067 (7) and 8.207 (7) Å (Wang et al., 2005), and 8.5541 (9) Å (Cooper et al., 2005).
The secondary structure is stabilized by a variety of O—H···O hydrogen bonds (Table 1, Fig. 2) and π-π stacking interactions (Fig. 3), connecting the cations, Hbtc anions, and bpy and water molecules of crystallization.