Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010200776X/gd1198sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010200776X/gd1198Isup2.hkl |
CCDC reference: 188600
All chemicals used were obtained commercially. Zinc–tetrakis(4-carboxyphenyl)porphyrin (7.5 mg, 0.01 mmol) was reacted with dibenzo-24-crown-8 (5 mg, 0.01 mmol) in warm methanol (4 ml). Toluene (10 drops) was added to this solution to control solubility. Single crystals of the title compound were then obtained by slow evaporation in open air.
The title compound is a racemic twin. The methyl group of the zinc-bound methanol molecule is orientationally disordered. These features, along with the somewhat high mosaicity of the analyzed crystal and the large number of available data, affected, to some extent, the precision of the crystallographic determination and resulted in somewhat high R factors. Atom H31 (bonded to O31) was located directly from a difference map, with an O—H distance of 0.78 Å; the remaining H atoms were placed in calculated postions, with C—H distances in the range 0.95–0.99 Å and O—H distances in the range 0.93–0.96 Å.
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski, 1985); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
[Zn(C44H28N4O4)]·3C24H32O8·4CH4O | Z = 1 |
Mr = 2215.73 | F(000) = 1174 |
Triclinic, P1 | Dx = 1.339 Mg m−3 |
a = 10.2643 (3) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 13.4878 (4) Å | Cell parameters from 18559 reflections |
c = 21.1227 (8) Å | θ = 1.9–27.8° |
α = 86.2858 (10)° | µ = 0.31 mm−1 |
β = 77.9955 (13)° | T = 110 K |
γ = 73.932 (3)° | Prism, red |
V = 2748.51 (15) Å3 | 0.35 × 0.30 × 0.25 mm |
Nonius KappaCCD diffractometer | 13092 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
Detector resolution: 56 microns pixels mm-1 | h = −11→12 |
0.8° ϕ and ω scans | k = −14→16 |
15453 measured reflections | l = −24→25 |
15453 independent 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)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.167 | w = 1/[σ2(Fo2) + (0.0644P)2 + 4.9932P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.136 |
15453 reflections | Δρmax = 0.96 e Å−3 |
1420 parameters | Δρmin = −0.55 e Å−3 |
4 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.477 (13) |
[Zn(C44H28N4O4)]·3C24H32O8·4CH4O | γ = 73.932 (3)° |
Mr = 2215.73 | V = 2748.51 (15) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.2643 (3) Å | Mo Kα radiation |
b = 13.4878 (4) Å | µ = 0.31 mm−1 |
c = 21.1227 (8) Å | T = 110 K |
α = 86.2858 (10)° | 0.35 × 0.30 × 0.25 mm |
β = 77.9955 (13)° |
Nonius KappaCCD diffractometer | 13092 reflections with I > 2σ(I) |
15453 measured reflections | Rint = 0.000 |
15453 independent reflections |
R[F2 > 2σ(F2)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.167 | (Δ/σ)max = 0.136 |
S = 1.05 | Δρmax = 0.96 e Å−3 |
15453 reflections | Δρmin = −0.55 e Å−3 |
1420 parameters | Absolute structure: Flack (1983) |
4 restraints | Absolute structure parameter: 0.477 (13) |
Experimental. 'Intensity data were measured up to theta=27.84 °. with completeness factor of 0.90, while to theta=25.0 °. the completeness was 94%. Due to the large size of the problem, the emphasis placed on the analysis of intermolecular organization rather than on fine details of the molecular structure, and very weak high-angle intensities, the smaller but more complete shell was used in the least-squares refinement calculations.' |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The compound is a racemic twin. The methyl group of the zinc-bound methanol is orientationally disordered. These features, along with somewhat high mosaicity of the analyzed crystal and the large number of available data, affected to some extent the precision of the crystallographic determination and resulted in somewhat high R-factors. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.7625 (5) | 0.0493 (4) | 0.7037 (2) | 0.0208 (11) | |
N2 | 0.6142 (5) | 0.1550 (4) | 0.8216 (2) | 0.0202 (12) | |
N3 | 0.6011 (5) | −0.0399 (3) | 0.8838 (2) | 0.0171 (11) | |
N4 | 0.7547 (5) | −0.1478 (4) | 0.7662 (2) | 0.0174 (11) | |
C5 | 0.8239 (6) | −0.1825 (4) | 0.7056 (3) | 0.0191 (13) | |
C6 | 0.8670 (6) | −0.1230 (5) | 0.6530 (3) | 0.0223 (14) | |
C7 | 0.8403 (6) | −0.0149 (5) | 0.6516 (3) | 0.0220 (14) | |
C8 | 0.8768 (7) | 0.0476 (5) | 0.5967 (3) | 0.0259 (15) | |
H8 | 0.9274 | 0.0234 | 0.5550 | 0.031* | |
C9 | 0.8262 (7) | 0.1468 (5) | 0.6150 (3) | 0.0263 (15) | |
H9 | 0.8360 | 0.2052 | 0.5887 | 0.032* | |
C10 | 0.7544 (7) | 0.1492 (5) | 0.6818 (3) | 0.0217 (13) | |
C11 | 0.6891 (6) | 0.2375 (4) | 0.7180 (3) | 0.0201 (13) | |
C12 | 0.6243 (6) | 0.2392 (4) | 0.7840 (3) | 0.0181 (12) | |
C13 | 0.5584 (6) | 0.3327 (5) | 0.8217 (3) | 0.0224 (14) | |
H13 | 0.5530 | 0.4014 | 0.8069 | 0.027* | |
C14 | 0.5063 (7) | 0.3031 (4) | 0.8815 (3) | 0.0217 (13) | |
H14 | 0.4572 | 0.3471 | 0.9171 | 0.026* | |
C15 | 0.5397 (6) | 0.1919 (4) | 0.8813 (3) | 0.0191 (13) | |
C16 | 0.4979 (6) | 0.1310 (4) | 0.9344 (3) | 0.0170 (13) | |
C17 | 0.5248 (6) | 0.0235 (5) | 0.9349 (3) | 0.0181 (13) | |
C18 | 0.4766 (6) | −0.0369 (5) | 0.9881 (3) | 0.0200 (13) | |
H18 | 0.4219 | −0.0113 | 1.0288 | 0.024* | |
C19 | 0.5231 (7) | −0.1371 (5) | 0.9700 (3) | 0.0232 (14) | |
H19 | 0.5084 | −0.1950 | 0.9956 | 0.028* | |
C20 | 0.5996 (6) | −0.1388 (4) | 0.9040 (3) | 0.0176 (12) | |
C21 | 0.6602 (6) | −0.2290 (4) | 0.8662 (3) | 0.0202 (13) | |
C22 | 0.7307 (7) | −0.2315 (4) | 0.8024 (3) | 0.0206 (13) | |
C23 | 0.7864 (7) | −0.3234 (5) | 0.7634 (3) | 0.0254 (14) | |
H23 | 0.7829 | −0.3914 | 0.7766 | 0.030* | |
C24 | 0.8450 (7) | −0.2934 (5) | 0.7039 (3) | 0.0233 (14) | |
H24 | 0.8912 | −0.3371 | 0.6679 | 0.028* | |
C25 | 0.9457 (6) | −0.1787 (5) | 0.5921 (3) | 0.0179 (13) | |
C26 | 1.0899 (7) | −0.1963 (5) | 0.5728 (3) | 0.0248 (14) | |
H26 | 1.1383 | −0.1683 | 0.5977 | 0.030* | |
C27 | 1.1617 (7) | −0.2530 (5) | 0.5191 (3) | 0.0283 (15) | |
H27 | 1.2593 | −0.2651 | 0.5073 | 0.034* | |
C28 | 1.0913 (7) | −0.2930 (5) | 0.4818 (3) | 0.0224 (14) | |
C29 | 0.9498 (6) | −0.2752 (5) | 0.4988 (3) | 0.0220 (14) | |
H29 | 0.9017 | −0.3014 | 0.4729 | 0.026* | |
C30 | 0.8778 (7) | −0.2191 (5) | 0.5538 (3) | 0.0211 (13) | |
H30 | 0.7803 | −0.2080 | 0.5656 | 0.025* | |
O31 | 1.1691 (5) | −0.3493 (4) | 0.4285 (2) | 0.0337 (12) | |
H31 | 1.1088 | −0.3702 | 0.4228 | 0.021 (18)* | |
C32 | 0.6900 (6) | 0.3386 (4) | 0.6850 (3) | 0.0184 (13) | |
C33 | 0.5673 (6) | 0.4025 (5) | 0.6679 (3) | 0.0206 (13) | |
H33 | 0.4838 | 0.3822 | 0.6791 | 0.025* | |
C34 | 0.5687 (7) | 0.4939 (5) | 0.6352 (3) | 0.0235 (14) | |
H34 | 0.4862 | 0.5360 | 0.6235 | 0.028* | |
C35 | 0.6881 (7) | 0.5251 (5) | 0.6192 (3) | 0.0234 (14) | |
C36 | 0.8076 (7) | 0.4646 (5) | 0.6367 (3) | 0.0276 (15) | |
H36 | 0.8901 | 0.4863 | 0.6259 | 0.033* | |
C37 | 0.8085 (7) | 0.3728 (5) | 0.6698 (3) | 0.0249 (14) | |
H37 | 0.8912 | 0.3327 | 0.6822 | 0.030* | |
O38 | 0.6968 (5) | 0.6139 (3) | 0.5846 (2) | 0.0337 (11) | |
H38 | 0.6268 | 0.6381 | 0.5587 | 0.09 (4)* | |
C39 | 0.4118 (7) | 0.1851 (4) | 0.9950 (3) | 0.0181 (13) | |
C40 | 0.4715 (6) | 0.2258 (5) | 1.0357 (3) | 0.0200 (13) | |
H40 | 0.5675 | 0.2213 | 1.0244 | 0.024* | |
C41 | 0.3938 (7) | 0.2741 (5) | 1.0938 (3) | 0.0240 (14) | |
H41 | 0.4370 | 0.3002 | 1.1221 | 0.029* | |
C42 | 0.2538 (7) | 0.2828 (5) | 1.1090 (3) | 0.0252 (15) | |
C43 | 0.1903 (7) | 0.2437 (5) | 1.0671 (3) | 0.0267 (14) | |
H43 | 0.0937 | 0.2501 | 1.0771 | 0.032* | |
C44 | 0.2722 (7) | 0.1952 (5) | 1.0104 (3) | 0.0229 (14) | |
H44 | 0.2303 | 0.1685 | 0.9818 | 0.027* | |
O45 | 0.1715 (5) | 0.3315 (4) | 1.1630 (2) | 0.0388 (12) | |
H45 | 0.2277 | 0.3288 | 1.1939 | 0.047* | |
C46 | 0.6494 (6) | −0.3289 (4) | 0.9001 (3) | 0.0191 (13) | |
C47 | 0.7643 (7) | −0.3938 (5) | 0.9192 (3) | 0.0216 (13) | |
H47 | 0.8505 | −0.3776 | 0.9077 | 0.026* | |
C48 | 0.7554 (7) | −0.4840 (5) | 0.9555 (3) | 0.0235 (14) | |
H48 | 0.8348 | −0.5289 | 0.9684 | 0.028* | |
C49 | 0.6280 (7) | −0.5057 (5) | 0.9720 (3) | 0.0234 (14) | |
C50 | 0.5124 (7) | −0.4439 (5) | 0.9517 (3) | 0.0253 (14) | |
H50 | 0.4271 | −0.4617 | 0.9618 | 0.030* | |
C51 | 0.5232 (6) | −0.3545 (5) | 0.9160 (3) | 0.0229 (13) | |
H51 | 0.4441 | −0.3107 | 0.9024 | 0.028* | |
O52 | 0.6124 (5) | −0.5914 (3) | 1.0093 (2) | 0.0300 (10) | |
H52 | 0.6976 | −0.6331 | 1.0187 | 0.036* | |
Zn53 | 0.71368 (6) | 0.00275 (5) | 0.79772 (3) | 0.01856 (17) | |
O54 | 0.9125 (4) | −0.0027 (3) | 0.8144 (2) | 0.0297 (10) | |
H54 | 0.9381 | −0.0061 | 0.8551 | 0.036* | |
C55 | 1.0233 (16) | 0.0404 (12) | 0.7588 (7) | 0.132 (6)* | |
H55A | 1.0477 | −0.0018 | 0.7198 | 0.198* | |
H55B | 1.1069 | 0.0363 | 0.7755 | 0.198* | |
H55C | 0.9808 | 0.1123 | 0.7481 | 0.198* | |
O56 | 1.0016 (5) | 0.2932 (3) | 0.4393 (2) | 0.0285 (10) | |
C57 | 1.0558 (7) | 0.1880 (5) | 0.4347 (3) | 0.0254 (14) | |
C58 | 1.1421 (7) | 0.1298 (6) | 0.4729 (3) | 0.0335 (16) | |
H58 | 1.1696 | 0.1623 | 0.5045 | 0.040* | |
C59 | 1.1890 (8) | 0.0243 (6) | 0.4655 (4) | 0.0387 (18) | |
H59 | 1.2473 | −0.0160 | 0.4926 | 0.046* | |
C60 | 1.1509 (8) | −0.0234 (6) | 0.4181 (4) | 0.046 (2) | |
H60 | 1.1851 | −0.0960 | 0.4126 | 0.055* | |
C61 | 1.0652 (8) | 0.0333 (6) | 0.3799 (4) | 0.0386 (18) | |
H61 | 1.0401 | −0.0001 | 0.3479 | 0.046* | |
C62 | 1.0138 (7) | 0.1403 (5) | 0.3874 (3) | 0.0325 (16) | |
O63 | 0.9258 (5) | 0.2037 (3) | 0.3525 (2) | 0.0303 (11) | |
C64 | 0.8660 (8) | 0.1562 (6) | 0.3108 (3) | 0.0378 (18) | |
H64A | 0.8292 | 0.1009 | 0.3346 | 0.045* | |
H64B | 0.9377 | 0.1249 | 0.2731 | 0.045* | |
C65 | 0.7494 (9) | 0.2384 (7) | 0.2877 (3) | 0.044 (2) | |
H65A | 0.6825 | 0.2034 | 0.2783 | 0.053* | |
H65B | 0.7006 | 0.2857 | 0.3243 | 0.053* | |
O66 | 0.7841 (7) | 0.3004 (5) | 0.2320 (3) | 0.0549 (16) | |
C67 | 0.8443 (9) | 0.3796 (8) | 0.2462 (4) | 0.051 (2) | |
H67A | 0.7834 | 0.4214 | 0.2833 | 0.061* | |
H67B | 0.9354 | 0.3474 | 0.2578 | 0.061* | |
C68 | 0.8599 (10) | 0.4428 (7) | 0.1909 (5) | 0.061 (3) | |
H68A | 0.9292 | 0.4801 | 0.1933 | 0.074* | |
H68B | 0.8936 | 0.3994 | 0.1517 | 0.074* | |
O69 | 0.7327 (5) | 0.5141 (4) | 0.1868 (3) | 0.0435 (13) | |
C70 | 0.7406 (8) | 0.5539 (6) | 0.1211 (4) | 0.0401 (18) | |
H70A | 0.6837 | 0.5252 | 0.0987 | 0.048* | |
H70B | 0.8376 | 0.5326 | 0.0971 | 0.048* | |
C71 | 0.6896 (8) | 0.6694 (5) | 0.1218 (3) | 0.0315 (16) | |
H71A | 0.6863 | 0.6959 | 0.0772 | 0.038* | |
H71B | 0.5949 | 0.6909 | 0.1482 | 0.038* | |
O72 | 0.7804 (5) | 0.7114 (3) | 0.1484 (2) | 0.0271 (10) | |
C73 | 0.7436 (6) | 0.8167 (5) | 0.1545 (3) | 0.0214 (13) | |
C74 | 0.6422 (7) | 0.8835 (5) | 0.1255 (3) | 0.0257 (14) | |
H74 | 0.5949 | 0.8570 | 0.0993 | 0.031* | |
C75 | 0.6107 (7) | 0.9894 (5) | 0.1351 (3) | 0.0313 (16) | |
H75 | 0.5412 | 1.0348 | 0.1156 | 0.038* | |
C76 | 0.6786 (7) | 1.0289 (5) | 0.1724 (3) | 0.0301 (15) | |
H76 | 0.6565 | 1.1013 | 0.1785 | 0.036* | |
C77 | 0.7813 (7) | 0.9616 (5) | 0.2014 (3) | 0.0292 (15) | |
H77 | 0.8286 | 0.9888 | 0.2272 | 0.035* | |
C78 | 0.8137 (6) | 0.8567 (5) | 0.1929 (3) | 0.0229 (14) | |
O79 | 0.9096 (4) | 0.7850 (3) | 0.2208 (2) | 0.0258 (10) | |
C80 | 0.9684 (8) | 0.8243 (6) | 0.2658 (4) | 0.0350 (17) | |
H80A | 0.8947 | 0.8624 | 0.3007 | 0.042* | |
H80B | 1.0221 | 0.8717 | 0.2438 | 0.042* | |
C81 | 1.0634 (8) | 0.7307 (6) | 0.2940 (4) | 0.0399 (18) | |
H81A | 1.1218 | 0.6846 | 0.2584 | 0.048* | |
H81B | 1.1254 | 0.7546 | 0.3160 | 0.048* | |
O82 | 0.9873 (5) | 0.6751 (4) | 0.3384 (2) | 0.0322 (11) | |
C83 | 0.9696 (7) | 0.5840 (5) | 0.3143 (3) | 0.0277 (15) | |
H83A | 1.0573 | 0.5448 | 0.2871 | 0.033* | |
H83B | 0.8975 | 0.6026 | 0.2877 | 0.033* | |
C84 | 0.9274 (7) | 0.5204 (5) | 0.3714 (3) | 0.0276 (15) | |
H84A | 0.8386 | 0.5588 | 0.3980 | 0.033* | |
H84B | 0.9158 | 0.4556 | 0.3568 | 0.033* | |
O85 | 1.0341 (5) | 0.4981 (3) | 0.4081 (2) | 0.0287 (10) | |
C86 | 0.9961 (8) | 0.4590 (5) | 0.4720 (3) | 0.0320 (16) | |
H86A | 0.8941 | 0.4737 | 0.4838 | 0.038* | |
H86B | 1.0264 | 0.4954 | 0.5032 | 0.038* | |
C87 | 1.0589 (7) | 0.3452 (5) | 0.4776 (3) | 0.0285 (15) | |
H87A | 1.1604 | 0.3287 | 0.4625 | 0.034* | |
H87B | 1.0395 | 0.3228 | 0.5233 | 0.034* | |
O88 | 0.3322 (5) | 0.7063 (3) | 0.1582 (2) | 0.0282 (10) | |
C89 | 0.2854 (7) | 0.8117 (5) | 0.1630 (3) | 0.0248 (14) | |
C90 | 0.2027 (7) | 0.8742 (5) | 0.1245 (3) | 0.0324 (16) | |
H90 | 0.1753 | 0.8451 | 0.0913 | 0.039* | |
C91 | 0.1591 (8) | 0.9813 (6) | 0.1346 (4) | 0.0385 (18) | |
H91 | 0.0992 | 1.0245 | 0.1092 | 0.046* | |
C92 | 0.2031 (8) | 1.0241 (5) | 0.1814 (3) | 0.0366 (17) | |
H92 | 0.1776 | 1.0968 | 0.1866 | 0.044* | |
C93 | 0.2836 (7) | 0.9610 (5) | 0.2203 (3) | 0.0324 (16) | |
H93 | 0.3084 | 0.9901 | 0.2543 | 0.039* | |
C94 | 0.3293 (6) | 0.8554 (5) | 0.2105 (3) | 0.0250 (14) | |
O95 | 0.4142 (5) | 0.7880 (3) | 0.2460 (2) | 0.0274 (10) | |
C96 | 0.4787 (7) | 0.8319 (5) | 0.2877 (3) | 0.0303 (15) | |
H96A | 0.4086 | 0.8658 | 0.3252 | 0.036* | |
H96B | 0.5210 | 0.8844 | 0.2636 | 0.036* | |
C97 | 0.5882 (8) | 0.7463 (6) | 0.3108 (3) | 0.0371 (18) | |
H97A | 0.6384 | 0.6996 | 0.2742 | 0.045* | |
H97B | 0.6556 | 0.7767 | 0.3242 | 0.045* | |
O98 | 0.5361 (5) | 0.6860 (4) | 0.3641 (2) | 0.0421 (13) | |
C99 | 0.4943 (8) | 0.5982 (6) | 0.3442 (4) | 0.0365 (17) | |
H99A | 0.4067 | 0.6238 | 0.3282 | 0.044* | |
H99B | 0.5663 | 0.5602 | 0.3087 | 0.044* | |
C100 | 0.4761 (8) | 0.5304 (6) | 0.3993 (3) | 0.0377 (17) | |
H10A | 0.4135 | 0.5702 | 0.4368 | 0.045* | |
H10B | 0.4347 | 0.4768 | 0.3889 | 0.045* | |
O101 | 0.6068 (5) | 0.4840 (4) | 0.4144 (3) | 0.0385 (12) | |
C102 | 0.5971 (8) | 0.4367 (6) | 0.4777 (4) | 0.0396 (18) | |
H10C | 0.4995 | 0.4580 | 0.5009 | 0.047* | |
H10D | 0.6528 | 0.4628 | 0.5023 | 0.047* | |
C103 | 0.6437 (7) | 0.3250 (5) | 0.4767 (3) | 0.0287 (15) | |
H10E | 0.6445 | 0.2980 | 0.5213 | 0.034* | |
H10F | 0.7391 | 0.3025 | 0.4510 | 0.034* | |
O104 | 0.5511 (5) | 0.2840 (3) | 0.4480 (2) | 0.0283 (10) | |
C105 | 0.5931 (7) | 0.1796 (5) | 0.4390 (3) | 0.0229 (14) | |
C106 | 0.6928 (7) | 0.1110 (5) | 0.4671 (3) | 0.0308 (16) | |
H106 | 0.7366 | 0.1359 | 0.4957 | 0.037* | |
C107 | 0.7299 (8) | 0.0060 (5) | 0.4540 (3) | 0.0339 (17) | |
H107 | 0.7991 | −0.0404 | 0.4732 | 0.041* | |
C108 | 0.6655 (8) | −0.0300 (5) | 0.4131 (3) | 0.0351 (17) | |
H108 | 0.6909 | −0.1017 | 0.4041 | 0.042* | |
C109 | 0.5656 (7) | 0.0355 (5) | 0.3851 (3) | 0.0294 (15) | |
H109 | 0.5226 | 0.0086 | 0.3571 | 0.035* | |
C110 | 0.5254 (7) | 0.1418 (5) | 0.3970 (3) | 0.0233 (14) | |
O111 | 0.4294 (5) | 0.2127 (3) | 0.3715 (2) | 0.0264 (10) | |
C112 | 0.3652 (7) | 0.1762 (6) | 0.3261 (3) | 0.0309 (16) | |
H11A | 0.3157 | 0.1260 | 0.3478 | 0.037* | |
H11B | 0.4370 | 0.1411 | 0.2895 | 0.037* | |
C113 | 0.2660 (7) | 0.2660 (6) | 0.3015 (3) | 0.0381 (18) | |
H11C | 0.1999 | 0.2410 | 0.2831 | 0.046* | |
H11D | 0.2126 | 0.3122 | 0.3381 | 0.046* | |
O114 | 0.3359 (5) | 0.3233 (3) | 0.2529 (2) | 0.0325 (11) | |
C115 | 0.3700 (7) | 0.4076 (5) | 0.2751 (3) | 0.0296 (15) | |
H11E | 0.4466 | 0.3828 | 0.2990 | 0.035* | |
H11F | 0.2891 | 0.4511 | 0.3043 | 0.035* | |
C116 | 0.4134 (8) | 0.4680 (6) | 0.2157 (4) | 0.0362 (17) | |
H11G | 0.4391 | 0.5284 | 0.2283 | 0.043* | |
H11H | 0.4947 | 0.4241 | 0.1868 | 0.043* | |
O117 | 0.2995 (4) | 0.5014 (3) | 0.1830 (2) | 0.0255 (10) | |
C118 | 0.3356 (7) | 0.5418 (5) | 0.1198 (3) | 0.0299 (15) | |
H11I | 0.3036 | 0.5074 | 0.0884 | 0.036* | |
H11J | 0.4375 | 0.5275 | 0.1072 | 0.036* | |
C119 | 0.2702 (8) | 0.6575 (5) | 0.1179 (3) | 0.0309 (16) | |
H11K | 0.2868 | 0.6837 | 0.0729 | 0.037* | |
H11L | 0.1691 | 0.6731 | 0.1342 | 0.037* | |
O120 | 0.0446 (5) | −0.2269 (4) | −0.0175 (2) | 0.0349 (11) | |
C121 | 0.0781 (7) | −0.3313 (5) | −0.0301 (4) | 0.0303 (16) | |
C122 | 0.0627 (7) | −0.3985 (6) | 0.0194 (3) | 0.0331 (16) | |
H122 | 0.0268 | −0.3728 | 0.0621 | 0.040* | |
C123 | 0.0976 (7) | −0.5031 (5) | 0.0094 (4) | 0.0354 (16) | |
H123 | 0.0853 | −0.5486 | 0.0451 | 0.042* | |
C124 | 0.1501 (8) | −0.5420 (6) | −0.0518 (4) | 0.0414 (18) | |
H124 | 0.1730 | −0.6142 | −0.0589 | 0.050* | |
C125 | 0.1696 (7) | −0.4740 (6) | −0.1038 (4) | 0.0386 (17) | |
H125 | 0.2080 | −0.5005 | −0.1463 | 0.046* | |
C126 | 0.1338 (7) | −0.3697 (6) | −0.0940 (3) | 0.0329 (16) | |
O127 | 0.1450 (5) | −0.2942 (4) | −0.1406 (2) | 0.0435 (13) | |
C128 | 0.1711 (9) | −0.3312 (6) | −0.2062 (4) | 0.0459 (19) | |
H12A | 0.1050 | −0.3704 | −0.2105 | 0.055* | |
H12B | 0.2663 | −0.3767 | −0.2181 | 0.055* | |
C129 | 0.1530 (8) | −0.2378 (7) | −0.2484 (4) | 0.048 (2) | |
H12C | 0.1495 | −0.2582 | −0.2921 | 0.058* | |
H12D | 0.0628 | −0.1889 | −0.2309 | 0.058* | |
O130 | 0.2599 (6) | −0.1851 (4) | −0.2545 (2) | 0.0465 (13) | |
C131 | 0.3809 (9) | −0.2340 (6) | −0.2961 (4) | 0.050 (2) | |
H13A | 0.3598 | −0.2499 | −0.3374 | 0.060* | |
H13B | 0.4268 | −0.2996 | −0.2765 | 0.060* | |
C132 | 0.4757 (8) | −0.1631 (6) | −0.3087 (4) | 0.0460 (19) | |
H13C | 0.4891 | −0.1418 | −0.2670 | 0.055* | |
H13D | 0.5672 | −0.2000 | −0.3338 | 0.055* | |
O133 | 0.4148 (5) | −0.0727 (4) | −0.3445 (2) | 0.0374 (12) | |
C134 | 0.5083 (8) | −0.0111 (6) | −0.3632 (4) | 0.0446 (19) | |
H13E | 0.5882 | −0.0479 | −0.3960 | 0.053* | |
H13F | 0.5434 | 0.0021 | −0.3252 | 0.053* | |
C135 | 0.4373 (9) | 0.0874 (7) | −0.3904 (4) | 0.049 (2) | |
H13G | 0.5054 | 0.1257 | −0.4102 | 0.059* | |
H13H | 0.3911 | 0.0742 | −0.4245 | 0.059* | |
O136 | 0.3370 (6) | 0.1474 (4) | −0.3400 (2) | 0.0467 (14) | |
C137 | 0.2849 (8) | 0.2518 (6) | −0.3493 (3) | 0.0359 (17) | |
C138 | 0.3075 (9) | 0.3061 (6) | −0.4066 (4) | 0.044 (2) | |
H138 | 0.3633 | 0.2699 | −0.4441 | 0.053* | |
C139 | 0.2521 (8) | 0.4099 (6) | −0.4107 (4) | 0.0423 (19) | |
H139 | 0.2690 | 0.4450 | −0.4508 | 0.051* | |
C140 | 0.1698 (8) | 0.4650 (7) | −0.3556 (4) | 0.049 (2) | |
H140 | 0.1333 | 0.5377 | −0.3576 | 0.059* | |
C141 | 0.1424 (7) | 0.4101 (6) | −0.2971 (4) | 0.0405 (18) | |
H141 | 0.0835 | 0.4460 | −0.2601 | 0.049* | |
C142 | 0.2001 (7) | 0.3048 (5) | −0.2931 (3) | 0.0317 (16) | |
O143 | 0.1702 (5) | 0.2530 (4) | −0.2372 (2) | 0.0346 (11) | |
C144 | 0.2874 (7) | 0.2100 (6) | −0.2057 (3) | 0.0367 (17) | |
H14A | 0.2736 | 0.2485 | −0.1654 | 0.044* | |
H14B | 0.3728 | 0.2189 | −0.2345 | 0.044* | |
C145 | 0.3049 (7) | 0.0976 (5) | −0.1897 (3) | 0.0310 (15) | |
H14C | 0.2991 | 0.0610 | −0.2278 | 0.037* | |
H14D | 0.3971 | 0.0668 | −0.1789 | 0.037* | |
O146 | 0.1991 (5) | 0.0857 (3) | −0.1359 (2) | 0.0302 (10) | |
C147 | 0.2221 (7) | −0.0213 (5) | −0.1162 (3) | 0.0306 (15) | |
H14E | 0.3181 | −0.0494 | −0.1094 | 0.037* | |
H14F | 0.2083 | −0.0623 | −0.1503 | 0.037* | |
C148 | 0.1209 (8) | −0.0283 (6) | −0.0541 (4) | 0.0430 (19) | |
H14G | 0.1497 | −0.0972 | −0.0339 | 0.052* | |
H14H | 0.1202 | 0.0243 | −0.0233 | 0.052* | |
O149 | −0.0146 (5) | −0.0117 (4) | −0.0673 (2) | 0.0360 (12) | |
C150 | −0.1051 (7) | −0.0587 (6) | −0.0196 (3) | 0.0320 (16) | |
H15A | −0.2026 | −0.0209 | −0.0197 | 0.038* | |
H15B | −0.0871 | −0.0522 | 0.0240 | 0.038* | |
C151 | −0.0843 (7) | −0.1692 (5) | −0.0330 (3) | 0.0315 (15) | |
H15C | −0.1607 | −0.1941 | −0.0065 | 0.038* | |
H15D | −0.0836 | −0.1783 | −0.0792 | 0.038* | |
O152 | 0.5288 (6) | 0.6896 (4) | 0.5006 (2) | 0.0449 (13) | |
H152 | 0.5380 | 0.6881 | 0.4554 | 0.054* | |
C153 | 0.5041 (9) | 0.7971 (5) | 0.5042 (4) | 0.0408 (18) | |
H15E | 0.4431 | 0.8218 | 0.5455 | 0.061* | |
H15F | 0.4601 | 0.8304 | 0.4685 | 0.061* | |
H15G | 0.5921 | 0.8142 | 0.5010 | 0.061* | |
O154 | 0.8529 (5) | 0.2933 (4) | 0.0358 (2) | 0.0377 (12) | |
H154 | 0.8971 | 0.2771 | −0.0071 | 0.045* | |
C155 | 0.8330 (9) | 0.2058 (6) | 0.0733 (5) | 0.056 (3) | |
H15H | 0.9120 | 0.1771 | 0.0944 | 0.085* | |
H15I | 0.8252 | 0.1537 | 0.0451 | 0.085* | |
H15J | 0.7481 | 0.2262 | 0.1062 | 0.085* | |
O156 | 0.9785 (5) | 0.2477 (4) | −0.0858 (2) | 0.0425 (13) | |
H156 | 1.0545 | 0.1919 | −0.1033 | 0.051* | |
C157 | 0.8756 (8) | 0.2643 (7) | −0.1250 (4) | 0.049 (2) | |
H15K | 0.8218 | 0.3368 | −0.1225 | 0.074* | |
H15L | 0.8139 | 0.2202 | −0.1092 | 0.074* | |
H15M | 0.9210 | 0.2470 | −0.1700 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.030 (3) | 0.012 (3) | 0.021 (3) | −0.003 (2) | −0.009 (2) | −0.002 (2) |
N2 | 0.034 (3) | 0.012 (3) | 0.016 (3) | −0.005 (2) | −0.007 (2) | −0.005 (2) |
N3 | 0.027 (3) | 0.006 (2) | 0.018 (3) | −0.001 (2) | −0.007 (2) | −0.001 (2) |
N4 | 0.023 (3) | 0.013 (3) | 0.014 (3) | −0.002 (2) | −0.002 (2) | −0.003 (2) |
C5 | 0.028 (4) | 0.017 (3) | 0.011 (3) | −0.003 (2) | −0.005 (2) | −0.002 (2) |
C6 | 0.018 (3) | 0.022 (3) | 0.027 (3) | −0.002 (2) | −0.006 (3) | −0.006 (3) |
C7 | 0.025 (4) | 0.021 (3) | 0.019 (3) | −0.003 (3) | −0.003 (2) | −0.009 (2) |
C8 | 0.044 (4) | 0.021 (4) | 0.011 (3) | −0.007 (3) | −0.004 (3) | −0.001 (2) |
C9 | 0.039 (4) | 0.019 (3) | 0.016 (3) | −0.006 (3) | 0.001 (3) | 0.000 (3) |
C10 | 0.026 (4) | 0.018 (3) | 0.023 (3) | −0.009 (3) | −0.007 (3) | 0.007 (3) |
C11 | 0.027 (4) | 0.017 (3) | 0.017 (3) | −0.004 (3) | −0.009 (3) | 0.000 (2) |
C12 | 0.021 (3) | 0.015 (3) | 0.020 (3) | −0.006 (2) | −0.002 (2) | −0.007 (2) |
C13 | 0.026 (4) | 0.014 (3) | 0.027 (3) | −0.003 (3) | −0.006 (3) | −0.007 (3) |
C14 | 0.034 (4) | 0.012 (3) | 0.017 (3) | −0.002 (3) | −0.006 (3) | −0.003 (2) |
C15 | 0.021 (3) | 0.015 (3) | 0.021 (3) | −0.005 (2) | −0.006 (2) | −0.001 (2) |
C16 | 0.023 (3) | 0.015 (3) | 0.012 (3) | −0.003 (2) | −0.001 (2) | −0.008 (2) |
C17 | 0.024 (3) | 0.020 (3) | 0.011 (3) | −0.006 (2) | −0.007 (2) | 0.001 (2) |
C18 | 0.023 (3) | 0.022 (3) | 0.015 (3) | −0.004 (3) | −0.004 (2) | −0.010 (2) |
C19 | 0.026 (4) | 0.019 (3) | 0.024 (3) | −0.005 (3) | −0.007 (3) | 0.005 (3) |
C20 | 0.020 (3) | 0.012 (3) | 0.021 (3) | −0.003 (2) | −0.006 (2) | 0.001 (2) |
C21 | 0.027 (4) | 0.010 (3) | 0.024 (3) | −0.004 (2) | −0.008 (3) | 0.001 (2) |
C22 | 0.029 (4) | 0.012 (3) | 0.025 (3) | −0.010 (2) | −0.007 (3) | 0.000 (2) |
C23 | 0.028 (4) | 0.014 (3) | 0.037 (4) | −0.005 (3) | −0.011 (3) | −0.002 (3) |
C24 | 0.026 (4) | 0.023 (3) | 0.019 (3) | −0.006 (3) | 0.001 (3) | −0.005 (3) |
C25 | 0.023 (4) | 0.016 (3) | 0.013 (3) | −0.004 (2) | 0.000 (2) | −0.003 (2) |
C26 | 0.033 (4) | 0.026 (4) | 0.019 (3) | −0.011 (3) | −0.008 (3) | −0.003 (3) |
C27 | 0.021 (4) | 0.040 (4) | 0.022 (3) | −0.007 (3) | −0.001 (3) | −0.005 (3) |
C28 | 0.023 (4) | 0.023 (4) | 0.019 (3) | −0.007 (3) | −0.001 (3) | −0.001 (3) |
C29 | 0.023 (4) | 0.026 (4) | 0.019 (3) | −0.006 (3) | −0.007 (3) | −0.008 (3) |
C30 | 0.023 (4) | 0.021 (3) | 0.020 (3) | −0.006 (3) | −0.005 (3) | −0.002 (2) |
O31 | 0.017 (3) | 0.057 (3) | 0.027 (2) | −0.010 (2) | 0.0050 (18) | −0.027 (2) |
C32 | 0.034 (4) | 0.011 (3) | 0.011 (3) | −0.006 (3) | −0.006 (2) | 0.001 (2) |
C33 | 0.025 (4) | 0.018 (3) | 0.021 (3) | −0.010 (3) | −0.004 (2) | 0.002 (2) |
C34 | 0.030 (4) | 0.023 (3) | 0.017 (3) | −0.005 (3) | −0.003 (3) | −0.004 (2) |
C35 | 0.033 (4) | 0.012 (3) | 0.026 (3) | −0.006 (3) | −0.008 (3) | 0.003 (2) |
C36 | 0.033 (4) | 0.027 (4) | 0.026 (3) | −0.016 (3) | −0.004 (3) | −0.001 (3) |
C37 | 0.029 (4) | 0.021 (4) | 0.027 (3) | −0.011 (3) | −0.005 (3) | −0.003 (3) |
O38 | 0.048 (3) | 0.020 (2) | 0.036 (3) | −0.015 (2) | −0.008 (2) | 0.009 (2) |
C39 | 0.027 (4) | 0.013 (3) | 0.015 (3) | −0.007 (2) | −0.005 (3) | 0.000 (2) |
C40 | 0.020 (3) | 0.018 (3) | 0.020 (3) | −0.004 (2) | 0.002 (2) | −0.007 (2) |
C41 | 0.030 (4) | 0.026 (4) | 0.020 (3) | −0.012 (3) | −0.007 (3) | −0.004 (3) |
C42 | 0.034 (4) | 0.024 (4) | 0.013 (3) | −0.006 (3) | 0.004 (3) | −0.007 (3) |
C43 | 0.015 (3) | 0.035 (4) | 0.032 (4) | −0.009 (3) | −0.005 (3) | −0.003 (3) |
C44 | 0.031 (4) | 0.020 (3) | 0.018 (3) | −0.006 (3) | −0.006 (3) | −0.009 (2) |
O45 | 0.028 (3) | 0.069 (4) | 0.022 (2) | −0.019 (2) | 0.003 (2) | −0.020 (2) |
C46 | 0.028 (4) | 0.012 (3) | 0.020 (3) | −0.007 (2) | −0.009 (3) | 0.000 (2) |
C47 | 0.022 (3) | 0.020 (3) | 0.025 (3) | −0.009 (3) | −0.004 (3) | −0.004 (3) |
C48 | 0.029 (4) | 0.014 (3) | 0.027 (3) | −0.006 (3) | −0.006 (3) | 0.001 (3) |
C49 | 0.035 (4) | 0.013 (3) | 0.022 (3) | −0.008 (3) | −0.002 (3) | −0.005 (2) |
C50 | 0.020 (4) | 0.022 (3) | 0.035 (4) | −0.007 (3) | −0.005 (3) | −0.002 (3) |
C51 | 0.024 (4) | 0.020 (3) | 0.029 (3) | −0.008 (3) | −0.011 (3) | −0.001 (3) |
O52 | 0.034 (3) | 0.021 (2) | 0.031 (2) | −0.010 (2) | 0.0020 (19) | 0.0055 (19) |
Zn53 | 0.0215 (4) | 0.0152 (3) | 0.0188 (3) | −0.0046 (3) | −0.0034 (3) | −0.0024 (3) |
O54 | 0.030 (3) | 0.034 (3) | 0.030 (2) | −0.011 (2) | −0.014 (2) | −0.0002 (19) |
O56 | 0.036 (3) | 0.020 (2) | 0.030 (3) | −0.004 (2) | −0.011 (2) | 0.0011 (19) |
C57 | 0.031 (4) | 0.016 (3) | 0.027 (3) | −0.006 (3) | 0.000 (3) | 0.000 (3) |
C58 | 0.029 (4) | 0.034 (4) | 0.034 (4) | −0.008 (3) | 0.001 (3) | 0.009 (3) |
C59 | 0.029 (4) | 0.031 (4) | 0.046 (5) | −0.004 (3) | 0.007 (3) | 0.009 (3) |
C60 | 0.038 (5) | 0.021 (4) | 0.066 (6) | −0.006 (3) | 0.017 (4) | 0.001 (4) |
C61 | 0.034 (4) | 0.028 (4) | 0.050 (5) | −0.013 (3) | 0.010 (3) | −0.007 (3) |
C62 | 0.031 (4) | 0.024 (4) | 0.040 (4) | −0.013 (3) | 0.006 (3) | −0.001 (3) |
O63 | 0.031 (3) | 0.030 (3) | 0.034 (3) | −0.011 (2) | −0.008 (2) | −0.009 (2) |
C64 | 0.040 (5) | 0.053 (5) | 0.027 (4) | −0.028 (4) | 0.007 (3) | −0.020 (3) |
C65 | 0.064 (6) | 0.059 (5) | 0.027 (4) | −0.046 (5) | −0.015 (4) | 0.011 (4) |
O66 | 0.080 (5) | 0.057 (4) | 0.039 (3) | −0.034 (3) | −0.014 (3) | −0.003 (3) |
C67 | 0.041 (5) | 0.078 (7) | 0.039 (4) | −0.027 (4) | −0.002 (4) | −0.018 (4) |
C68 | 0.055 (6) | 0.039 (5) | 0.095 (7) | −0.008 (4) | −0.033 (5) | 0.002 (5) |
O69 | 0.035 (3) | 0.022 (3) | 0.069 (4) | −0.001 (2) | −0.014 (3) | 0.013 (2) |
C70 | 0.048 (5) | 0.030 (4) | 0.038 (4) | −0.017 (3) | 0.010 (3) | −0.006 (3) |
C71 | 0.047 (5) | 0.034 (4) | 0.020 (3) | −0.027 (3) | 0.001 (3) | −0.003 (3) |
O72 | 0.030 (3) | 0.020 (2) | 0.030 (2) | −0.0079 (19) | −0.0033 (19) | −0.0009 (19) |
C73 | 0.024 (4) | 0.022 (4) | 0.016 (3) | −0.009 (3) | 0.005 (2) | 0.000 (2) |
C74 | 0.037 (4) | 0.026 (4) | 0.019 (3) | −0.016 (3) | −0.006 (3) | 0.005 (3) |
C75 | 0.032 (4) | 0.037 (4) | 0.022 (3) | −0.006 (3) | −0.006 (3) | 0.007 (3) |
C76 | 0.035 (4) | 0.023 (4) | 0.033 (4) | −0.011 (3) | −0.006 (3) | 0.004 (3) |
C77 | 0.037 (4) | 0.029 (4) | 0.026 (4) | −0.013 (3) | −0.010 (3) | −0.002 (3) |
C78 | 0.021 (4) | 0.027 (4) | 0.017 (3) | −0.005 (3) | 0.000 (2) | 0.003 (3) |
O79 | 0.022 (2) | 0.031 (3) | 0.025 (2) | −0.0050 (19) | −0.0082 (18) | −0.0005 (19) |
C80 | 0.039 (4) | 0.035 (4) | 0.038 (4) | −0.016 (3) | −0.017 (3) | 0.010 (3) |
C81 | 0.044 (5) | 0.040 (5) | 0.044 (4) | −0.017 (4) | −0.022 (4) | 0.014 (3) |
O82 | 0.051 (3) | 0.031 (3) | 0.020 (2) | −0.020 (2) | −0.010 (2) | 0.0061 (19) |
C83 | 0.039 (4) | 0.026 (4) | 0.022 (3) | −0.007 (3) | −0.014 (3) | −0.006 (3) |
C84 | 0.029 (4) | 0.032 (4) | 0.030 (4) | −0.015 (3) | −0.016 (3) | 0.002 (3) |
O85 | 0.034 (3) | 0.028 (3) | 0.026 (2) | −0.010 (2) | −0.012 (2) | 0.0001 (19) |
C86 | 0.043 (4) | 0.021 (4) | 0.030 (4) | −0.005 (3) | −0.009 (3) | 0.001 (3) |
C87 | 0.033 (4) | 0.030 (4) | 0.027 (4) | −0.012 (3) | −0.014 (3) | 0.004 (3) |
O88 | 0.029 (3) | 0.026 (3) | 0.032 (3) | −0.008 (2) | −0.011 (2) | −0.003 (2) |
C89 | 0.023 (4) | 0.028 (4) | 0.024 (3) | −0.008 (3) | −0.004 (3) | 0.003 (3) |
C90 | 0.042 (4) | 0.022 (4) | 0.032 (4) | −0.005 (3) | −0.009 (3) | 0.000 (3) |
C91 | 0.035 (4) | 0.031 (4) | 0.042 (4) | −0.003 (3) | −0.005 (3) | 0.016 (3) |
C92 | 0.050 (5) | 0.020 (4) | 0.037 (4) | −0.013 (3) | 0.002 (3) | 0.004 (3) |
C93 | 0.031 (4) | 0.033 (4) | 0.035 (4) | −0.013 (3) | −0.003 (3) | −0.005 (3) |
C94 | 0.022 (4) | 0.022 (4) | 0.027 (3) | −0.001 (3) | −0.002 (3) | −0.005 (3) |
O95 | 0.032 (3) | 0.029 (3) | 0.024 (2) | −0.010 (2) | −0.0070 (19) | −0.0029 (19) |
C96 | 0.035 (4) | 0.034 (4) | 0.024 (3) | −0.015 (3) | 0.001 (3) | −0.011 (3) |
C97 | 0.048 (5) | 0.052 (5) | 0.020 (3) | −0.028 (4) | −0.010 (3) | 0.011 (3) |
O98 | 0.046 (3) | 0.048 (3) | 0.033 (3) | −0.014 (3) | −0.007 (2) | −0.009 (2) |
C99 | 0.038 (4) | 0.035 (4) | 0.043 (4) | −0.015 (3) | −0.010 (3) | −0.018 (3) |
C100 | 0.044 (5) | 0.042 (4) | 0.032 (4) | −0.017 (3) | −0.014 (3) | 0.003 (3) |
O101 | 0.025 (3) | 0.029 (3) | 0.059 (3) | −0.004 (2) | −0.009 (2) | 0.007 (2) |
C102 | 0.048 (5) | 0.038 (4) | 0.037 (4) | −0.021 (4) | −0.004 (3) | −0.004 (3) |
C103 | 0.030 (4) | 0.037 (4) | 0.021 (3) | −0.009 (3) | −0.006 (3) | −0.007 (3) |
O104 | 0.036 (3) | 0.024 (3) | 0.025 (2) | −0.009 (2) | −0.005 (2) | −0.0060 (19) |
C105 | 0.030 (4) | 0.019 (3) | 0.017 (3) | −0.006 (3) | −0.001 (3) | 0.002 (2) |
C106 | 0.040 (4) | 0.036 (4) | 0.019 (3) | −0.016 (3) | −0.006 (3) | 0.007 (3) |
C107 | 0.044 (5) | 0.020 (4) | 0.036 (4) | −0.006 (3) | −0.012 (3) | 0.015 (3) |
C108 | 0.049 (5) | 0.018 (4) | 0.038 (4) | −0.009 (3) | −0.008 (3) | 0.003 (3) |
C109 | 0.033 (4) | 0.031 (4) | 0.030 (4) | −0.018 (3) | −0.004 (3) | −0.006 (3) |
C110 | 0.027 (4) | 0.027 (4) | 0.016 (3) | −0.012 (3) | 0.001 (3) | −0.001 (3) |
O111 | 0.029 (3) | 0.023 (3) | 0.028 (2) | −0.0056 (19) | −0.0077 (19) | −0.0049 (19) |
C112 | 0.030 (4) | 0.039 (4) | 0.032 (4) | −0.023 (3) | −0.008 (3) | 0.004 (3) |
C113 | 0.034 (4) | 0.060 (5) | 0.032 (4) | −0.027 (4) | −0.016 (3) | 0.015 (3) |
O114 | 0.054 (3) | 0.028 (3) | 0.021 (2) | −0.019 (2) | −0.009 (2) | −0.0017 (19) |
C115 | 0.032 (4) | 0.036 (4) | 0.026 (3) | −0.012 (3) | −0.014 (3) | 0.000 (3) |
C116 | 0.033 (4) | 0.033 (4) | 0.048 (4) | −0.012 (3) | −0.015 (3) | −0.001 (3) |
O117 | 0.026 (3) | 0.028 (3) | 0.025 (2) | −0.0080 (19) | −0.0091 (18) | 0.0037 (18) |
C118 | 0.041 (4) | 0.028 (4) | 0.022 (3) | −0.012 (3) | −0.006 (3) | −0.002 (3) |
C119 | 0.047 (5) | 0.037 (4) | 0.014 (3) | −0.015 (3) | −0.013 (3) | −0.002 (3) |
O120 | 0.033 (3) | 0.028 (3) | 0.046 (3) | −0.006 (2) | −0.016 (2) | 0.000 (2) |
C121 | 0.024 (4) | 0.019 (4) | 0.052 (4) | −0.007 (3) | −0.017 (3) | 0.003 (3) |
C122 | 0.019 (4) | 0.046 (5) | 0.037 (4) | −0.016 (3) | −0.006 (3) | 0.009 (3) |
C123 | 0.022 (4) | 0.034 (4) | 0.045 (4) | −0.004 (3) | −0.003 (3) | 0.005 (3) |
C124 | 0.033 (4) | 0.032 (4) | 0.056 (5) | −0.008 (3) | −0.004 (3) | 0.004 (4) |
C125 | 0.030 (4) | 0.035 (4) | 0.048 (4) | −0.004 (3) | −0.009 (3) | 0.000 (3) |
C126 | 0.030 (4) | 0.040 (4) | 0.035 (4) | −0.017 (3) | −0.013 (3) | 0.010 (3) |
O127 | 0.046 (3) | 0.041 (3) | 0.044 (3) | −0.011 (2) | −0.008 (2) | −0.006 (2) |
C128 | 0.057 (6) | 0.044 (5) | 0.037 (4) | −0.019 (4) | −0.004 (4) | 0.003 (3) |
C129 | 0.039 (5) | 0.065 (6) | 0.045 (4) | −0.014 (4) | −0.017 (4) | 0.000 (4) |
O130 | 0.053 (4) | 0.041 (3) | 0.045 (3) | −0.015 (3) | −0.004 (3) | −0.003 (2) |
C131 | 0.059 (6) | 0.032 (4) | 0.044 (5) | 0.002 (4) | 0.004 (4) | −0.001 (4) |
C132 | 0.032 (5) | 0.043 (5) | 0.060 (5) | −0.005 (3) | −0.010 (4) | −0.003 (4) |
O133 | 0.030 (3) | 0.038 (3) | 0.044 (3) | −0.006 (2) | −0.009 (2) | −0.002 (2) |
C134 | 0.038 (5) | 0.041 (5) | 0.055 (5) | −0.014 (4) | −0.001 (4) | −0.013 (4) |
C135 | 0.047 (5) | 0.056 (6) | 0.034 (4) | −0.007 (4) | 0.010 (3) | −0.013 (4) |
O136 | 0.060 (4) | 0.031 (3) | 0.037 (3) | −0.002 (2) | 0.007 (2) | 0.000 (2) |
C137 | 0.035 (4) | 0.042 (4) | 0.029 (4) | −0.010 (3) | −0.005 (3) | 0.003 (3) |
C138 | 0.052 (5) | 0.048 (5) | 0.044 (5) | −0.025 (4) | −0.018 (4) | 0.007 (4) |
C139 | 0.041 (5) | 0.048 (5) | 0.046 (5) | −0.024 (4) | −0.017 (4) | 0.022 (4) |
C140 | 0.029 (5) | 0.045 (5) | 0.076 (6) | −0.006 (4) | −0.023 (4) | 0.012 (4) |
C141 | 0.025 (4) | 0.049 (5) | 0.046 (4) | −0.011 (3) | −0.004 (3) | 0.006 (4) |
C142 | 0.027 (4) | 0.033 (4) | 0.038 (4) | −0.009 (3) | −0.010 (3) | −0.003 (3) |
O143 | 0.029 (3) | 0.041 (3) | 0.032 (3) | −0.011 (2) | −0.001 (2) | 0.004 (2) |
C144 | 0.030 (4) | 0.050 (5) | 0.037 (4) | −0.024 (3) | −0.008 (3) | 0.009 (3) |
C145 | 0.028 (4) | 0.040 (4) | 0.024 (3) | −0.009 (3) | −0.008 (3) | 0.006 (3) |
O146 | 0.033 (3) | 0.030 (3) | 0.031 (2) | −0.015 (2) | −0.005 (2) | 0.0041 (19) |
C147 | 0.035 (4) | 0.022 (4) | 0.037 (4) | −0.007 (3) | −0.016 (3) | 0.006 (3) |
C148 | 0.057 (5) | 0.048 (5) | 0.042 (4) | −0.033 (4) | −0.029 (4) | 0.017 (4) |
O149 | 0.038 (3) | 0.041 (3) | 0.038 (3) | −0.018 (2) | −0.019 (2) | 0.013 (2) |
C150 | 0.026 (4) | 0.037 (4) | 0.030 (4) | −0.010 (3) | −0.001 (3) | 0.005 (3) |
C151 | 0.030 (4) | 0.031 (4) | 0.033 (4) | −0.006 (3) | −0.008 (3) | 0.002 (3) |
O152 | 0.060 (4) | 0.034 (3) | 0.040 (3) | −0.011 (2) | −0.012 (3) | 0.006 (2) |
C153 | 0.056 (5) | 0.028 (4) | 0.044 (4) | −0.016 (4) | −0.018 (4) | 0.001 (3) |
O154 | 0.040 (3) | 0.035 (3) | 0.038 (3) | −0.012 (2) | −0.008 (2) | 0.010 (2) |
C155 | 0.052 (6) | 0.045 (5) | 0.085 (7) | −0.023 (4) | −0.042 (5) | 0.040 (5) |
O156 | 0.035 (3) | 0.042 (3) | 0.047 (3) | −0.004 (2) | −0.005 (2) | −0.010 (2) |
C157 | 0.037 (5) | 0.054 (5) | 0.060 (5) | −0.009 (4) | −0.014 (4) | −0.019 (4) |
N1—C10 | 1.381 (8) | C84—H84A | 0.9900 |
N1—C7 | 1.406 (8) | C84—H84B | 0.9900 |
N1—Zn53 | 2.047 (5) | O85—C86 | 1.434 (8) |
N2—C12 | 1.358 (8) | C86—C87 | 1.499 (9) |
N2—C15 | 1.376 (8) | C86—H86A | 0.9900 |
N2—Zn53 | 2.068 (5) | C86—H86B | 0.9899 |
N3—C20 | 1.377 (7) | C87—H87A | 0.9900 |
N3—C17 | 1.380 (7) | C87—H87B | 0.9900 |
N3—Zn53 | 2.081 (5) | O88—C89 | 1.372 (8) |
N4—C5 | 1.370 (7) | O88—C119 | 1.447 (8) |
N4—C22 | 1.373 (7) | C89—C90 | 1.376 (9) |
N4—Zn53 | 2.081 (5) | C89—C94 | 1.403 (9) |
C5—C6 | 1.396 (9) | C90—C91 | 1.405 (10) |
C5—C24 | 1.454 (8) | C90—H90 | 0.9500 |
C6—C7 | 1.405 (8) | C91—C92 | 1.386 (11) |
C6—C25 | 1.494 (8) | C91—H91 | 0.9500 |
C7—C8 | 1.437 (9) | C92—C93 | 1.372 (10) |
C8—C9 | 1.345 (9) | C92—H92 | 0.9500 |
C8—H8 | 0.9500 | C93—C94 | 1.386 (9) |
C9—C10 | 1.447 (9) | C93—H93 | 0.9500 |
C9—H9 | 0.9500 | C94—O95 | 1.377 (8) |
C10—C11 | 1.384 (8) | O95—C96 | 1.446 (8) |
C11—C12 | 1.414 (8) | C96—C97 | 1.507 (10) |
C11—C32 | 1.492 (8) | C96—H96A | 0.9900 |
C12—C13 | 1.454 (8) | C96—H96B | 0.9900 |
C13—C14 | 1.347 (9) | C97—O98 | 1.444 (8) |
C13—H13 | 0.9500 | C97—H97A | 0.9901 |
C14—C15 | 1.444 (8) | C97—H97B | 0.9899 |
C14—H14 | 0.9500 | O98—C99 | 1.478 (8) |
C15—C16 | 1.411 (8) | C99—C100 | 1.448 (11) |
C16—C17 | 1.399 (8) | C99—H99A | 0.9901 |
C16—C39 | 1.499 (8) | C99—H99B | 0.9900 |
C17—C18 | 1.430 (9) | C100—O101 | 1.407 (8) |
C18—C19 | 1.354 (9) | C100—H10A | 0.9899 |
C18—H18 | 0.9500 | C100—H10B | 0.9900 |
C19—C20 | 1.450 (9) | O101—C102 | 1.440 (9) |
C19—H19 | 0.9500 | C102—C103 | 1.449 (10) |
C20—C21 | 1.416 (8) | C102—H10C | 0.9900 |
C21—C22 | 1.388 (9) | C102—H10D | 0.9900 |
C21—C46 | 1.506 (8) | C103—O104 | 1.466 (8) |
C22—C23 | 1.444 (9) | C103—H10E | 0.9900 |
C23—C24 | 1.363 (9) | C103—H10F | 0.9899 |
C23—H23 | 0.9500 | O104—C105 | 1.368 (7) |
C24—H24 | 0.9500 | C105—C106 | 1.383 (9) |
C25—C30 | 1.393 (8) | C105—C110 | 1.428 (9) |
C25—C26 | 1.407 (9) | C106—C107 | 1.390 (10) |
C26—C27 | 1.366 (9) | C106—H106 | 0.9500 |
C26—H26 | 0.9500 | C107—C108 | 1.375 (10) |
C27—C28 | 1.394 (9) | C107—H107 | 0.9500 |
C27—H27 | 0.9500 | C108—C109 | 1.365 (10) |
C28—O31 | 1.373 (7) | C108—H108 | 0.9500 |
C28—C29 | 1.378 (9) | C109—C110 | 1.401 (9) |
C29—C30 | 1.383 (8) | C109—H109 | 0.9500 |
C29—H29 | 0.9500 | C110—O111 | 1.346 (8) |
C30—H30 | 0.9500 | O111—C112 | 1.450 (8) |
O31—H31 | 0.7805 | C112—C113 | 1.494 (10) |
C32—C37 | 1.388 (9) | C112—H11A | 0.9900 |
C32—C33 | 1.417 (8) | C112—H11B | 0.9899 |
C33—C34 | 1.377 (9) | C113—O114 | 1.437 (8) |
C33—H33 | 0.9500 | C113—H11C | 0.9900 |
C34—C35 | 1.374 (9) | C113—H11D | 0.9899 |
C34—H34 | 0.9500 | O114—C115 | 1.411 (8) |
C35—O38 | 1.377 (7) | C115—C116 | 1.507 (10) |
C35—C36 | 1.380 (9) | C115—H11E | 0.9900 |
C36—C37 | 1.380 (9) | C115—H11F | 0.9900 |
C36—H36 | 0.9500 | C116—O117 | 1.432 (8) |
C37—H37 | 0.9500 | C116—H11G | 0.9900 |
O38—H38 | 0.9649 | C116—H11H | 0.9900 |
C39—C44 | 1.371 (9) | O117—C118 | 1.425 (8) |
C39—C40 | 1.372 (8) | C118—C119 | 1.520 (10) |
C40—C41 | 1.405 (9) | C118—H11I | 0.9900 |
C40—H40 | 0.9500 | C118—H11J | 0.9900 |
C41—C42 | 1.379 (9) | C119—H11K | 0.9900 |
C41—H41 | 0.9500 | C119—H11L | 0.9900 |
C42—O45 | 1.354 (7) | O120—C121 | 1.385 (8) |
C42—C43 | 1.407 (9) | O120—C151 | 1.428 (8) |
C43—C44 | 1.394 (9) | C121—C122 | 1.351 (9) |
C43—H43 | 0.9500 | C121—C126 | 1.421 (10) |
C44—H44 | 0.9500 | C122—C123 | 1.375 (10) |
O45—H45 | 0.9505 | C122—H122 | 0.9500 |
C46—C47 | 1.378 (9) | C123—C124 | 1.370 (10) |
C46—C51 | 1.400 (9) | C123—H123 | 0.9500 |
C47—C48 | 1.409 (9) | C124—C125 | 1.404 (10) |
C47—H47 | 0.9500 | C124—H124 | 0.9500 |
C48—C49 | 1.388 (9) | C125—C126 | 1.370 (10) |
C48—H48 | 0.9500 | C125—H125 | 0.9500 |
C49—C50 | 1.379 (9) | C126—O127 | 1.381 (8) |
C49—O52 | 1.383 (7) | O127—C128 | 1.449 (9) |
C50—C51 | 1.398 (9) | C128—C129 | 1.486 (11) |
C50—H50 | 0.9500 | C128—H12A | 0.9900 |
C51—H51 | 0.9500 | C128—H12B | 0.9900 |
O52—H52 | 0.9518 | C129—O130 | 1.446 (10) |
Zn53—O54 | 2.123 (4) | C129—H12C | 0.9901 |
O54—C55 | 1.654 (13) | C129—H12D | 0.9899 |
O54—H54 | 0.9440 | O130—C131 | 1.385 (10) |
C55—H55A | 0.9800 | C131—C132 | 1.519 (12) |
C55—H55B | 0.9800 | C131—H13A | 0.9900 |
C55—H55C | 0.9800 | C131—H13B | 0.9900 |
O56—C57 | 1.375 (8) | C132—O133 | 1.451 (9) |
O56—C87 | 1.411 (8) | C132—H13C | 0.9899 |
C57—C58 | 1.372 (10) | C132—H13D | 0.9900 |
C57—C62 | 1.419 (10) | O133—C134 | 1.418 (9) |
C58—C59 | 1.378 (10) | C134—C135 | 1.472 (12) |
C58—H58 | 0.9500 | C134—H13E | 0.9900 |
C59—C60 | 1.398 (12) | C134—H13F | 0.9900 |
C59—H59 | 0.9500 | C135—O136 | 1.429 (9) |
C60—C61 | 1.362 (12) | C135—H13G | 0.9899 |
C60—H60 | 0.9500 | C135—H13H | 0.9900 |
C61—C62 | 1.400 (10) | O136—C137 | 1.378 (9) |
C61—H61 | 0.9500 | C137—C138 | 1.384 (10) |
C62—O63 | 1.363 (8) | C137—C142 | 1.419 (10) |
O63—C64 | 1.442 (8) | C138—C139 | 1.361 (11) |
C64—C65 | 1.529 (12) | C138—H138 | 0.9500 |
C64—H64A | 0.9900 | C139—C140 | 1.406 (12) |
C64—H64B | 0.9901 | C139—H139 | 0.9500 |
C65—O66 | 1.440 (9) | C140—C141 | 1.417 (11) |
C65—H65A | 0.9900 | C140—H140 | 0.9500 |
C65—H65B | 0.9900 | C141—C142 | 1.383 (10) |
O66—C67 | 1.448 (10) | C141—H141 | 0.9500 |
C67—C68 | 1.409 (13) | C142—O143 | 1.355 (8) |
C67—H67A | 0.9901 | O143—C144 | 1.458 (8) |
C67—H67B | 0.9898 | C144—C145 | 1.502 (10) |
C68—O69 | 1.407 (10) | C144—H14A | 0.9900 |
C68—H68A | 0.9902 | C144—H14B | 0.9900 |
C68—H68B | 0.9905 | C145—O146 | 1.434 (8) |
O69—C70 | 1.451 (9) | C145—H14C | 0.9900 |
C70—C71 | 1.499 (10) | C145—H14D | 0.9900 |
C70—H70A | 0.9900 | O146—C147 | 1.444 (8) |
C70—H70B | 0.9900 | C147—C148 | 1.511 (10) |
C71—O72 | 1.435 (8) | C147—H14E | 0.9900 |
C71—H71A | 0.9900 | C147—H14F | 0.9900 |
C71—H71B | 0.9901 | C148—O149 | 1.430 (9) |
O72—C73 | 1.372 (7) | C148—H14G | 0.9900 |
C73—C74 | 1.395 (9) | C148—H14H | 0.9900 |
C73—C78 | 1.407 (9) | O149—C150 | 1.460 (8) |
C74—C75 | 1.392 (9) | C150—C151 | 1.483 (10) |
C74—H74 | 0.9500 | C150—H15A | 0.9900 |
C75—C76 | 1.370 (10) | C150—H15B | 0.9900 |
C75—H75 | 0.9500 | C151—H15C | 0.9900 |
C76—C77 | 1.407 (10) | C151—H15D | 0.9900 |
C76—H76 | 0.9500 | O152—C153 | 1.406 (8) |
C77—C78 | 1.375 (9) | O152—H152 | 0.9410 |
C77—H77 | 0.9500 | C153—H15E | 0.9800 |
C78—O79 | 1.376 (7) | C153—H15F | 0.9800 |
O79—C80 | 1.425 (8) | C153—H15G | 0.9800 |
C80—C81 | 1.537 (10) | O154—C155 | 1.415 (9) |
C80—H80A | 0.9900 | O154—H154 | 0.9344 |
C80—H80B | 0.9900 | C155—H15H | 0.9800 |
C81—O82 | 1.406 (8) | C155—H15I | 0.9800 |
C81—H81A | 0.9900 | C155—H15J | 0.9800 |
C81—H81B | 0.9900 | O156—C157 | 1.435 (9) |
O82—C83 | 1.430 (8) | O156—H156 | 0.9497 |
C83—C84 | 1.494 (9) | C157—H15K | 0.9800 |
C83—H83A | 0.9900 | C157—H15L | 0.9800 |
C83—H83B | 0.9900 | C157—H15M | 0.9800 |
C84—O85 | 1.426 (7) | ||
C10—N1—C7 | 106.0 (5) | C83—C84—H84B | 110.3 |
C10—N1—Zn53 | 126.7 (4) | H84A—C84—H84B | 108.5 |
C7—N1—Zn53 | 125.8 (4) | C84—O85—C86 | 114.4 (5) |
C12—N2—C15 | 106.2 (5) | O85—C86—C87 | 112.4 (6) |
C12—N2—Zn53 | 126.6 (4) | O85—C86—H86A | 109.1 |
C15—N2—Zn53 | 126.7 (4) | C87—C86—H86A | 109.1 |
C20—N3—C17 | 106.0 (5) | O85—C86—H86B | 109.1 |
C20—N3—Zn53 | 126.6 (4) | C87—C86—H86B | 109.1 |
C17—N3—Zn53 | 127.1 (4) | H86A—C86—H86B | 107.9 |
C5—N4—C22 | 107.5 (5) | O56—C87—C86 | 108.8 (5) |
C5—N4—Zn53 | 124.8 (4) | O56—C87—H87A | 109.9 |
C22—N4—Zn53 | 127.5 (4) | C86—C87—H87A | 109.9 |
N4—C5—C6 | 126.8 (5) | O56—C87—H87B | 109.9 |
N4—C5—C24 | 108.7 (5) | C86—C87—H87B | 109.9 |
C6—C5—C24 | 124.5 (5) | H87A—C87—H87B | 108.3 |
C5—C6—C7 | 126.0 (6) | C89—O88—C119 | 116.6 (5) |
C5—C6—C25 | 117.2 (5) | O88—C89—C90 | 124.6 (6) |
C7—C6—C25 | 116.8 (5) | O88—C89—C94 | 115.4 (5) |
C6—C7—N1 | 124.0 (6) | C90—C89—C94 | 120.0 (6) |
C6—C7—C8 | 126.5 (5) | C89—C90—C91 | 119.6 (6) |
N1—C7—C8 | 109.3 (5) | C89—C90—H90 | 120.2 |
C9—C8—C7 | 107.4 (5) | C91—C90—H90 | 120.2 |
C9—C8—H8 | 126.3 | C92—C91—C90 | 120.2 (7) |
C7—C8—H8 | 126.3 | C92—C91—H91 | 119.9 |
C8—C9—C10 | 108.1 (6) | C90—C91—H91 | 119.9 |
C8—C9—H9 | 125.9 | C93—C92—C91 | 119.7 (7) |
C10—C9—H9 | 125.9 | C93—C92—H92 | 120.1 |
N1—C10—C11 | 125.6 (6) | C91—C92—H92 | 120.1 |
N1—C10—C9 | 109.2 (5) | C92—C93—C94 | 120.8 (6) |
C11—C10—C9 | 125.3 (5) | C92—C93—H93 | 119.6 |
C10—C11—C12 | 125.0 (5) | C94—C93—H93 | 119.6 |
C10—C11—C32 | 117.4 (5) | O95—C94—C93 | 123.9 (6) |
C12—C11—C32 | 117.5 (5) | O95—C94—C89 | 116.5 (5) |
N2—C12—C11 | 125.7 (5) | C93—C94—C89 | 119.6 (6) |
N2—C12—C13 | 110.0 (5) | C94—O95—C96 | 117.4 (5) |
C11—C12—C13 | 124.4 (6) | O95—C96—C97 | 108.4 (5) |
C14—C13—C12 | 106.9 (5) | O95—C96—H96A | 110.0 |
C14—C13—H13 | 126.5 | C97—C96—H96A | 110.0 |
C12—C13—H13 | 126.5 | O95—C96—H96B | 110.0 |
C13—C14—C15 | 106.8 (5) | C97—C96—H96B | 110.0 |
C13—C14—H14 | 126.6 | H96A—C96—H96B | 108.4 |
C15—C14—H14 | 126.6 | O98—C97—C96 | 114.5 (6) |
N2—C15—C16 | 125.5 (5) | O98—C97—H97A | 108.6 |
N2—C15—C14 | 110.0 (5) | C96—C97—H97A | 108.6 |
C16—C15—C14 | 124.5 (5) | O98—C97—H97B | 108.6 |
C17—C16—C15 | 125.6 (5) | C96—C97—H97B | 108.6 |
C17—C16—C39 | 116.3 (5) | H97A—C97—H97B | 107.6 |
C15—C16—C39 | 118.0 (5) | C97—O98—C99 | 114.1 (5) |
N3—C17—C16 | 125.0 (5) | C100—C99—O98 | 108.8 (6) |
N3—C17—C18 | 110.0 (5) | C100—C99—H99A | 109.9 |
C16—C17—C18 | 125.0 (5) | O98—C99—H99A | 109.9 |
C19—C18—C17 | 107.5 (5) | C100—C99—H99B | 109.9 |
C19—C18—H18 | 126.2 | O98—C99—H99B | 109.9 |
C17—C18—H18 | 126.2 | H99A—C99—H99B | 108.3 |
C18—C19—C20 | 106.7 (5) | O101—C100—C99 | 108.0 (6) |
C18—C19—H19 | 126.6 | O101—C100—H10A | 110.1 |
C20—C19—H19 | 126.6 | C99—C100—H10A | 110.1 |
N3—C20—C21 | 125.9 (5) | O101—C100—H10B | 110.1 |
N3—C20—C19 | 109.7 (5) | C99—C100—H10B | 110.1 |
C21—C20—C19 | 124.5 (5) | H10A—C100—H10B | 108.4 |
C22—C21—C20 | 125.1 (5) | C100—O101—C102 | 112.3 (6) |
C22—C21—C46 | 119.0 (5) | O101—C102—C103 | 113.9 (6) |
C20—C21—C46 | 115.8 (5) | O101—C102—H10C | 108.8 |
N4—C22—C21 | 125.7 (5) | C103—C102—H10C | 108.8 |
N4—C22—C23 | 109.7 (5) | O101—C102—H10D | 108.8 |
C21—C22—C23 | 124.6 (5) | C103—C102—H10D | 108.8 |
C24—C23—C22 | 106.6 (5) | H10C—C102—H10D | 107.7 |
C24—C23—H23 | 126.7 | C102—C103—O104 | 109.8 (5) |
C22—C23—H23 | 126.7 | C102—C103—H10E | 109.7 |
C23—C24—C5 | 107.5 (5) | O104—C103—H10E | 109.7 |
C23—C24—H24 | 126.3 | C102—C103—H10F | 109.7 |
C5—C24—H24 | 126.3 | O104—C103—H10F | 109.7 |
C30—C25—C26 | 117.8 (6) | H10E—C103—H10F | 108.2 |
C30—C25—C6 | 120.2 (6) | C105—O104—C103 | 114.6 (5) |
C26—C25—C6 | 121.9 (5) | O104—C105—C106 | 125.3 (6) |
C27—C26—C25 | 121.3 (6) | O104—C105—C110 | 115.2 (5) |
C27—C26—H26 | 119.4 | C106—C105—C110 | 119.5 (6) |
C25—C26—H26 | 119.4 | C105—C106—C107 | 120.9 (6) |
C26—C27—C28 | 119.8 (6) | C105—C106—H106 | 119.5 |
C26—C27—H27 | 120.1 | C107—C106—H106 | 119.5 |
C28—C27—H27 | 120.1 | C108—C107—C106 | 119.4 (6) |
O31—C28—C29 | 122.8 (5) | C108—C107—H107 | 120.3 |
O31—C28—C27 | 117.1 (6) | C106—C107—H107 | 120.3 |
C29—C28—C27 | 120.2 (6) | C109—C108—C107 | 121.1 (7) |
C28—C29—C30 | 119.9 (6) | C109—C108—H108 | 119.4 |
C28—C29—H29 | 120.1 | C107—C108—H108 | 119.4 |
C30—C29—H29 | 120.1 | C108—C109—C110 | 121.2 (6) |
C29—C30—C25 | 121.1 (6) | C108—C109—H109 | 119.4 |
C29—C30—H30 | 119.5 | C110—C109—H109 | 119.4 |
C25—C30—H30 | 119.5 | O111—C110—C109 | 125.8 (6) |
C28—O31—H31 | 94.0 | O111—C110—C105 | 116.3 (5) |
C37—C32—C33 | 118.1 (6) | C109—C110—C105 | 117.8 (6) |
C37—C32—C11 | 122.1 (6) | C110—O111—C112 | 116.9 (5) |
C33—C32—C11 | 119.9 (5) | O111—C112—C113 | 109.0 (6) |
C34—C33—C32 | 120.1 (6) | O111—C112—H11A | 109.9 |
C34—C33—H33 | 119.9 | C113—C112—H11A | 109.9 |
C32—C33—H33 | 119.9 | O111—C112—H11B | 109.9 |
C35—C34—C33 | 120.8 (6) | C113—C112—H11B | 109.9 |
C35—C34—H34 | 119.6 | H11A—C112—H11B | 108.3 |
C33—C34—H34 | 119.6 | O114—C113—C112 | 111.7 (6) |
C34—C35—O38 | 123.3 (6) | O114—C113—H11C | 109.3 |
C34—C35—C36 | 119.6 (6) | C112—C113—H11C | 109.3 |
O38—C35—C36 | 117.1 (6) | O114—C113—H11D | 109.3 |
C35—C36—C37 | 120.6 (6) | C112—C113—H11D | 109.3 |
C35—C36—H36 | 119.7 | H11C—C113—H11D | 107.9 |
C37—C36—H36 | 119.7 | C115—O114—C113 | 116.0 (5) |
C36—C37—C32 | 120.7 (6) | O114—C115—C116 | 106.3 (5) |
C36—C37—H37 | 119.6 | O114—C115—H11E | 110.5 |
C32—C37—H37 | 119.6 | C116—C115—H11E | 110.5 |
C35—O38—H38 | 113.8 | O114—C115—H11F | 110.5 |
C44—C39—C40 | 119.1 (6) | C116—C115—H11F | 110.5 |
C44—C39—C16 | 120.6 (5) | H11E—C115—H11F | 108.7 |
C40—C39—C16 | 120.4 (6) | O117—C116—C115 | 108.1 (6) |
C39—C40—C41 | 121.5 (6) | O117—C116—H11G | 110.1 |
C39—C40—H40 | 119.3 | C115—C116—H11G | 110.1 |
C41—C40—H40 | 119.3 | O117—C116—H11H | 110.1 |
C42—C41—C40 | 118.9 (6) | C115—C116—H11H | 110.1 |
C42—C41—H41 | 120.6 | H11G—C116—H11H | 108.4 |
C40—C41—H41 | 120.6 | C118—O117—C116 | 113.5 (5) |
O45—C42—C41 | 122.2 (6) | O117—C118—C119 | 110.6 (5) |
O45—C42—C43 | 117.4 (6) | O117—C118—H11I | 109.5 |
C41—C42—C43 | 120.4 (6) | C119—C118—H11I | 109.5 |
C44—C43—C42 | 118.6 (6) | O117—C118—H11J | 109.5 |
C44—C43—H43 | 120.7 | C119—C118—H11J | 109.5 |
C42—C43—H43 | 120.7 | H11I—C118—H11J | 108.1 |
C39—C44—C43 | 121.6 (6) | O88—C119—C118 | 107.9 (5) |
C39—C44—H44 | 119.2 | O88—C119—H11K | 110.1 |
C43—C44—H44 | 119.2 | C118—C119—H11K | 110.1 |
C42—O45—H45 | 107.8 | O88—C119—H11L | 110.1 |
C47—C46—C51 | 119.2 (6) | C118—C119—H11L | 110.1 |
C47—C46—C21 | 119.3 (6) | H11K—C119—H11L | 108.4 |
C51—C46—C21 | 121.4 (5) | C121—O120—C151 | 114.1 (5) |
C46—C47—C48 | 120.8 (6) | C122—C121—O120 | 119.6 (7) |
C46—C47—H47 | 119.6 | C122—C121—C126 | 119.3 (6) |
C48—C47—H47 | 119.6 | O120—C121—C126 | 121.1 (6) |
C49—C48—C47 | 118.5 (6) | C121—C122—C123 | 121.7 (7) |
C49—C48—H48 | 120.8 | C121—C122—H122 | 119.2 |
C47—C48—H48 | 120.8 | C123—C122—H122 | 119.2 |
C50—C49—O52 | 117.3 (6) | C124—C123—C122 | 120.2 (7) |
C50—C49—C48 | 121.9 (6) | C124—C123—H123 | 119.9 |
O52—C49—C48 | 120.9 (6) | C122—C123—H123 | 119.9 |
C49—C50—C51 | 118.7 (6) | C123—C124—C125 | 119.2 (7) |
C49—C50—H50 | 120.6 | C123—C124—H124 | 120.4 |
C51—C50—H50 | 120.6 | C125—C124—H124 | 120.4 |
C50—C51—C46 | 120.8 (6) | C126—C125—C124 | 120.5 (7) |
C50—C51—H51 | 119.6 | C126—C125—H125 | 119.7 |
C46—C51—H51 | 119.6 | C124—C125—H125 | 119.7 |
C49—O52—H52 | 112.6 | C125—C126—O127 | 126.7 (7) |
N1—Zn53—N2 | 88.46 (19) | C125—C126—C121 | 119.1 (6) |
N1—Zn53—N4 | 89.46 (18) | O127—C126—C121 | 114.3 (6) |
N2—Zn53—N4 | 162.08 (19) | C126—O127—C128 | 113.6 (6) |
N1—Zn53—N3 | 160.60 (19) | O127—C128—C129 | 106.1 (6) |
N2—Zn53—N3 | 88.18 (19) | O127—C128—H12A | 110.5 |
N4—Zn53—N3 | 87.90 (18) | C129—C128—H12A | 110.5 |
N1—Zn53—O54 | 92.14 (19) | O127—C128—H12B | 110.5 |
N2—Zn53—O54 | 99.05 (19) | C129—C128—H12B | 110.5 |
N4—Zn53—O54 | 98.82 (18) | H12A—C128—H12B | 108.7 |
N3—Zn53—O54 | 107.26 (18) | O130—C129—C128 | 114.8 (6) |
C55—O54—Zn53 | 120.3 (6) | O130—C129—H12C | 108.6 |
C55—O54—H54 | 110.1 | C128—C129—H12C | 108.5 |
Zn53—O54—H54 | 126.4 | O130—C129—H12D | 108.6 |
O54—C55—H55A | 109.5 | C128—C129—H12D | 108.6 |
O54—C55—H55B | 109.5 | H12C—C129—H12D | 107.5 |
H55A—C55—H55B | 109.5 | C131—O130—C129 | 113.0 (6) |
O54—C55—H55C | 109.5 | O130—C131—C132 | 108.6 (6) |
H55A—C55—H55C | 109.5 | O130—C131—H13A | 110.0 |
H55B—C55—H55C | 109.5 | C132—C131—H13A | 110.0 |
C57—O56—C87 | 116.6 (5) | O130—C131—H13B | 110.0 |
C58—C57—O56 | 124.3 (6) | C132—C131—H13B | 110.0 |
C58—C57—C62 | 120.5 (6) | H13A—C131—H13B | 108.3 |
O56—C57—C62 | 115.2 (6) | O133—C132—C131 | 109.5 (6) |
C57—C58—C59 | 120.1 (7) | O133—C132—H13C | 109.8 |
C57—C58—H58 | 119.9 | C131—C132—H13C | 109.8 |
C59—C58—H58 | 119.9 | O133—C132—H13D | 109.8 |
C58—C59—C60 | 120.0 (7) | C131—C132—H13D | 109.8 |
C58—C59—H59 | 120.0 | H13C—C132—H13D | 108.2 |
C60—C59—H59 | 120.0 | C134—O133—C132 | 110.5 (6) |
C61—C60—C59 | 120.6 (7) | O133—C134—C135 | 109.5 (7) |
C61—C60—H60 | 119.7 | O133—C134—H13E | 109.8 |
C59—C60—H60 | 119.7 | C135—C134—H13E | 109.8 |
C60—C61—C62 | 120.5 (8) | O133—C134—H13F | 109.8 |
C60—C61—H61 | 119.8 | C135—C134—H13F | 109.8 |
C62—C61—H61 | 119.8 | H13E—C134—H13F | 108.2 |
O63—C62—C61 | 125.1 (7) | O136—C135—C134 | 109.3 (6) |
O63—C62—C57 | 116.5 (6) | O136—C135—H13G | 109.8 |
C61—C62—C57 | 118.3 (7) | C134—C135—H13G | 109.8 |
C62—O63—C64 | 117.7 (6) | O136—C135—H13H | 109.8 |
O63—C64—C65 | 108.9 (6) | C134—C135—H13H | 109.8 |
O63—C64—H64A | 109.9 | H13G—C135—H13H | 108.3 |
C65—C64—H64A | 109.9 | C137—O136—C135 | 119.5 (6) |
O63—C64—H64B | 109.9 | O136—C137—C138 | 126.4 (7) |
C65—C64—H64B | 109.9 | O136—C137—C142 | 114.1 (6) |
H64A—C64—H64B | 108.3 | C138—C137—C142 | 119.6 (7) |
O66—C65—C64 | 118.6 (7) | C139—C138—C137 | 122.0 (8) |
O66—C65—H65A | 107.7 | C139—C138—H138 | 119.0 |
C64—C65—H65A | 107.7 | C137—C138—H138 | 119.0 |
O66—C65—H65B | 107.7 | C138—C139—C140 | 119.9 (7) |
C64—C65—H65B | 107.7 | C138—C139—H139 | 120.1 |
H65A—C65—H65B | 107.1 | C140—C139—H139 | 120.1 |
C65—O66—C67 | 113.0 (6) | C139—C140—C141 | 118.8 (7) |
C68—C67—O66 | 108.5 (7) | C139—C140—H140 | 120.6 |
C68—C67—H67A | 110.0 | C141—C140—H140 | 120.6 |
O66—C67—H67A | 110.0 | C142—C141—C140 | 120.9 (7) |
C68—C67—H67B | 110.0 | C142—C141—H141 | 119.5 |
O66—C67—H67B | 110.0 | C140—C141—H141 | 119.5 |
H67A—C67—H67B | 108.4 | O143—C142—C141 | 120.2 (6) |
O69—C68—C67 | 110.2 (9) | O143—C142—C137 | 120.9 (6) |
O69—C68—H68A | 109.6 | C141—C142—C137 | 118.8 (7) |
C67—C68—H68A | 109.7 | C142—O143—C144 | 114.4 (5) |
O69—C68—H68B | 109.6 | O143—C144—C145 | 111.9 (5) |
C67—C68—H68B | 109.6 | O143—C144—H14A | 109.2 |
H68A—C68—H68B | 108.1 | C145—C144—H14A | 109.2 |
C68—O69—C70 | 108.4 (7) | O143—C144—H14B | 109.2 |
O69—C70—C71 | 109.9 (5) | C145—C144—H14B | 109.2 |
O69—C70—H70A | 109.7 | H14A—C144—H14B | 107.9 |
C71—C70—H70A | 109.7 | O146—C145—C144 | 109.8 (6) |
O69—C70—H70B | 109.7 | O146—C145—H14C | 109.7 |
C71—C70—H70B | 109.7 | C144—C145—H14C | 109.7 |
H70A—C70—H70B | 108.2 | O146—C145—H14D | 109.7 |
O72—C71—C70 | 109.6 (6) | C144—C145—H14D | 109.7 |
O72—C71—H71A | 109.8 | H14C—C145—H14D | 108.2 |
C70—C71—H71A | 109.8 | C145—O146—C147 | 110.4 (5) |
O72—C71—H71B | 109.8 | O146—C147—C148 | 108.5 (6) |
C70—C71—H71B | 109.8 | O146—C147—H14E | 110.0 |
H71A—C71—H71B | 108.2 | C148—C147—H14E | 110.0 |
C73—O72—C71 | 116.2 (5) | O146—C147—H14F | 110.0 |
O72—C73—C74 | 123.8 (5) | C148—C147—H14F | 110.0 |
O72—C73—C78 | 116.4 (5) | H14E—C147—H14F | 108.4 |
C74—C73—C78 | 119.8 (6) | O149—C148—C147 | 109.8 (5) |
C75—C74—C73 | 119.6 (6) | O149—C148—H14G | 109.7 |
C75—C74—H74 | 120.2 | C147—C148—H14G | 109.7 |
C73—C74—H74 | 120.2 | O149—C148—H14H | 109.7 |
C76—C75—C74 | 120.9 (6) | C147—C148—H14H | 109.7 |
C76—C75—H75 | 119.5 | H14G—C148—H14H | 108.2 |
C74—C75—H75 | 119.5 | C148—O149—C150 | 113.9 (5) |
C75—C76—C77 | 119.5 (6) | O149—C150—C151 | 112.3 (6) |
C75—C76—H76 | 120.2 | O149—C150—H15A | 109.1 |
C77—C76—H76 | 120.2 | C151—C150—H15A | 109.1 |
C78—C77—C76 | 120.6 (6) | O149—C150—H15B | 109.1 |
C78—C77—H77 | 119.7 | C151—C150—H15B | 109.1 |
C76—C77—H77 | 119.7 | H15A—C150—H15B | 107.9 |
C77—C78—O79 | 124.6 (6) | O120—C151—C150 | 108.7 (5) |
C77—C78—C73 | 119.5 (6) | O120—C151—H15C | 110.0 |
O79—C78—C73 | 115.8 (5) | C150—C151—H15C | 110.0 |
C78—O79—C80 | 115.9 (5) | O120—C151—H15D | 110.0 |
O79—C80—C81 | 106.7 (6) | C150—C151—H15D | 110.0 |
O79—C80—H80A | 110.4 | H15C—C151—H15D | 108.3 |
C81—C80—H80A | 110.4 | C153—O152—H152 | 95.4 |
O79—C80—H80B | 110.4 | O152—C153—H15E | 109.5 |
C81—C80—H80B | 110.4 | O152—C153—H15F | 109.5 |
H80A—C80—H80B | 108.6 | H15E—C153—H15F | 109.5 |
O82—C81—C80 | 111.7 (6) | O152—C153—H15G | 109.5 |
O82—C81—H81A | 109.3 | H15E—C153—H15G | 109.5 |
C80—C81—H81A | 109.3 | H15F—C153—H15G | 109.5 |
O82—C81—H81B | 109.3 | C155—O154—H154 | 113.0 |
C80—C81—H81B | 109.3 | O154—C155—H15H | 109.5 |
H81A—C81—H81B | 107.9 | O154—C155—H15I | 109.5 |
C81—O82—C83 | 116.2 (5) | H15H—C155—H15I | 109.5 |
O82—C83—C84 | 107.6 (5) | O154—C155—H15J | 109.5 |
O82—C83—H83A | 110.2 | H15H—C155—H15J | 109.5 |
C84—C83—H83A | 110.2 | H15I—C155—H15J | 109.5 |
O82—C83—H83B | 110.2 | C157—O156—H156 | 108.7 |
C84—C83—H83B | 110.2 | O156—C157—H15K | 109.5 |
H83A—C83—H83B | 108.5 | O156—C157—H15L | 109.5 |
O85—C84—C83 | 107.3 (5) | H15K—C157—H15L | 109.5 |
O85—C84—H84A | 110.3 | O156—C157—H15M | 109.5 |
C83—C84—H84A | 110.3 | H15K—C157—H15M | 109.5 |
O85—C84—H84B | 110.3 | H15L—C157—H15M | 109.5 |
C22—N4—C5—C6 | 179.0 (6) | C5—N4—Zn53—N3 | 175.3 (5) |
Zn53—N4—C5—C6 | −6.5 (9) | C22—N4—Zn53—N3 | −11.2 (5) |
C22—N4—C5—C24 | −0.4 (7) | C5—N4—Zn53—O54 | −77.5 (5) |
Zn53—N4—C5—C24 | 174.1 (4) | C22—N4—Zn53—O54 | 95.9 (5) |
N4—C5—C6—C7 | −3.9 (10) | C20—N3—Zn53—N1 | 94.2 (7) |
C24—C5—C6—C7 | 175.4 (6) | C17—N3—Zn53—N1 | −93.1 (7) |
N4—C5—C6—C25 | 177.8 (6) | C20—N3—Zn53—N2 | 174.3 (5) |
C24—C5—C6—C25 | −2.9 (9) | C17—N3—Zn53—N2 | −13.0 (5) |
C5—C6—C7—N1 | −1.2 (10) | C20—N3—Zn53—N4 | 11.8 (5) |
C25—C6—C7—N1 | 177.1 (6) | C17—N3—Zn53—N4 | −175.5 (5) |
C5—C6—C7—C8 | −175.9 (7) | C20—N3—Zn53—O54 | −86.7 (5) |
C25—C6—C7—C8 | 2.3 (9) | C17—N3—Zn53—O54 | 86.0 (5) |
C10—N1—C7—C6 | −177.0 (6) | N1—Zn53—O54—C55 | 7.2 (7) |
Zn53—N1—C7—C6 | 16.4 (8) | N2—Zn53—O54—C55 | −81.6 (7) |
C10—N1—C7—C8 | −1.5 (7) | N4—Zn53—O54—C55 | 96.9 (7) |
Zn53—N1—C7—C8 | −168.1 (4) | N3—Zn53—O54—C55 | −172.5 (7) |
C6—C7—C8—C9 | 176.9 (6) | C87—O56—C57—C58 | 11.9 (9) |
N1—C7—C8—C9 | 1.5 (7) | C87—O56—C57—C62 | −169.4 (6) |
C7—C8—C9—C10 | −1.0 (8) | O56—C57—C58—C59 | 178.7 (6) |
C7—N1—C10—C11 | −178.6 (6) | C62—C57—C58—C59 | 0.1 (10) |
Zn53—N1—C10—C11 | −12.1 (9) | C57—C58—C59—C60 | 1.3 (11) |
C7—N1—C10—C9 | 0.9 (7) | C58—C59—C60—C61 | −1.4 (11) |
Zn53—N1—C10—C9 | 167.4 (4) | C59—C60—C61—C62 | 0.0 (11) |
C8—C9—C10—N1 | 0.1 (8) | C60—C61—C62—O63 | −178.8 (7) |
C8—C9—C10—C11 | 179.6 (6) | C60—C61—C62—C57 | 1.4 (10) |
N1—C10—C11—C12 | 2.3 (10) | C58—C57—C62—O63 | 178.8 (6) |
C9—C10—C11—C12 | −177.1 (6) | O56—C57—C62—O63 | 0.0 (9) |
N1—C10—C11—C32 | −179.1 (5) | C58—C57—C62—C61 | −1.4 (10) |
C9—C10—C11—C32 | 1.5 (9) | O56—C57—C62—C61 | 179.8 (6) |
C15—N2—C12—C11 | −177.9 (6) | C61—C62—O63—C64 | 8.8 (9) |
Zn53—N2—C12—C11 | 9.7 (9) | C57—C62—O63—C64 | −171.4 (6) |
C15—N2—C12—C13 | 2.1 (7) | C62—O63—C64—C65 | 168.2 (6) |
Zn53—N2—C12—C13 | −170.3 (4) | O63—C64—C65—O66 | 84.7 (7) |
C10—C11—C12—N2 | −1.1 (10) | C64—C65—O66—C67 | −76.1 (9) |
C32—C11—C12—N2 | −179.7 (5) | C65—O66—C67—C68 | −173.5 (8) |
C10—C11—C12—C13 | 178.8 (6) | O66—C67—C68—O69 | 79.5 (9) |
C32—C11—C12—C13 | 0.2 (9) | C67—C68—O69—C70 | −161.9 (7) |
N2—C12—C13—C14 | −1.4 (7) | C68—O69—C70—C71 | −131.6 (7) |
C11—C12—C13—C14 | 178.7 (6) | O69—C70—C71—O72 | 65.0 (7) |
C12—C13—C14—C15 | 0.1 (7) | C70—C71—O72—C73 | −177.6 (5) |
C12—N2—C15—C16 | 176.3 (6) | C71—O72—C73—C74 | −12.9 (8) |
Zn53—N2—C15—C16 | −11.4 (9) | C71—O72—C73—C78 | 166.7 (5) |
C12—N2—C15—C14 | −2.1 (7) | O72—C73—C74—C75 | 179.2 (5) |
Zn53—N2—C15—C14 | 170.3 (4) | C78—C73—C74—C75 | −0.4 (9) |
C13—C14—C15—N2 | 1.3 (7) | C73—C74—C75—C76 | 0.4 (10) |
C13—C14—C15—C16 | −177.1 (6) | C74—C75—C76—C77 | −0.2 (10) |
N2—C15—C16—C17 | −0.4 (10) | C75—C76—C77—C78 | −0.1 (11) |
C14—C15—C16—C17 | 177.8 (6) | C76—C77—C78—O79 | −178.1 (6) |
N2—C15—C16—C39 | −177.4 (5) | C76—C77—C78—C73 | 0.2 (10) |
C14—C15—C16—C39 | 0.7 (9) | O72—C73—C78—C77 | −179.5 (5) |
C20—N3—C17—C16 | −178.8 (6) | C74—C73—C78—C77 | 0.1 (9) |
Zn53—N3—C17—C16 | 7.3 (8) | O72—C73—C78—O79 | −1.1 (8) |
C20—N3—C17—C18 | 0.9 (6) | C74—C73—C78—O79 | 178.5 (5) |
Zn53—N3—C17—C18 | −173.0 (4) | C77—C78—O79—C80 | 5.7 (9) |
C15—C16—C17—N3 | 2.5 (9) | C73—C78—O79—C80 | −172.6 (6) |
C39—C16—C17—N3 | 179.6 (5) | C78—O79—C80—C81 | 176.1 (5) |
C15—C16—C17—C18 | −177.1 (6) | O79—C80—C81—O82 | −74.4 (7) |
C39—C16—C17—C18 | 0.0 (9) | C80—C81—O82—C83 | 99.8 (7) |
N3—C17—C18—C19 | 0.1 (7) | C81—O82—C83—C84 | 162.6 (5) |
C16—C17—C18—C19 | 179.7 (6) | O82—C83—C84—O85 | −58.8 (7) |
C17—C18—C19—C20 | −0.9 (7) | C83—C84—O85—C86 | 165.8 (5) |
C17—N3—C20—C21 | 177.2 (6) | C84—O85—C86—C87 | 104.6 (6) |
Zn53—N3—C20—C21 | −8.8 (8) | C57—O56—C87—C86 | 175.1 (5) |
C17—N3—C20—C19 | −1.4 (6) | O85—C86—C87—O56 | −66.3 (7) |
Zn53—N3—C20—C19 | 172.5 (4) | C119—O88—C89—C90 | −11.3 (9) |
C18—C19—C20—N3 | 1.5 (7) | C119—O88—C89—C94 | 169.6 (6) |
C18—C19—C20—C21 | −177.2 (6) | O88—C89—C90—C91 | 178.9 (6) |
N3—C20—C21—C22 | −0.3 (10) | C94—C89—C90—C91 | −2.1 (10) |
C19—C20—C21—C22 | 178.2 (6) | C89—C90—C91—C92 | 2.3 (11) |
N3—C20—C21—C46 | 177.7 (5) | C90—C91—C92—C93 | −3.4 (11) |
C19—C20—C21—C46 | −3.8 (9) | C91—C92—C93—C94 | 4.3 (11) |
C5—N4—C22—C21 | −178.4 (6) | C92—C93—C94—O95 | 177.6 (6) |
Zn53—N4—C22—C21 | 7.2 (9) | C92—C93—C94—C89 | −4.1 (10) |
C5—N4—C22—C23 | −0.1 (7) | O88—C89—C94—O95 | 0.5 (8) |
Zn53—N4—C22—C23 | −174.4 (4) | C90—C89—C94—O95 | −178.6 (6) |
C20—C21—C22—N4 | 1.1 (10) | O88—C89—C94—C93 | −177.9 (6) |
C46—C21—C22—N4 | −176.8 (5) | C90—C89—C94—C93 | 3.0 (10) |
C20—C21—C22—C23 | −176.9 (6) | C93—C94—O95—C96 | −11.5 (9) |
C46—C21—C22—C23 | 5.2 (9) | C89—C94—O95—C96 | 170.2 (6) |
N4—C22—C23—C24 | 0.6 (7) | C94—O95—C96—C97 | −168.4 (5) |
C21—C22—C23—C24 | 179.0 (6) | O95—C96—C97—O98 | −80.3 (7) |
C22—C23—C24—C5 | −0.9 (7) | C96—C97—O98—C99 | 87.6 (7) |
N4—C5—C24—C23 | 0.8 (7) | C97—O98—C99—C100 | 166.4 (6) |
C6—C5—C24—C23 | −178.6 (6) | O98—C99—C100—O101 | −68.2 (7) |
C5—C6—C25—C30 | 73.2 (8) | C99—C100—O101—C102 | 164.9 (6) |
C7—C6—C25—C30 | −105.3 (7) | C100—O101—C102—C103 | 111.0 (7) |
C5—C6—C25—C26 | −104.0 (7) | O101—C102—C103—O104 | −65.9 (7) |
C7—C6—C25—C26 | 77.6 (8) | C102—C103—O104—C105 | 174.1 (5) |
C30—C25—C26—C27 | −1.4 (9) | C103—O104—C105—C106 | 15.3 (9) |
C6—C25—C26—C27 | 175.8 (6) | C103—O104—C105—C110 | −164.9 (5) |
C25—C26—C27—C28 | 1.1 (10) | O104—C105—C106—C107 | −178.9 (6) |
C26—C27—C28—O31 | −179.9 (6) | C110—C105—C106—C107 | 1.2 (10) |
C26—C27—C28—C29 | 0.2 (10) | C105—C106—C107—C108 | −0.6 (10) |
O31—C28—C29—C30 | 179.0 (6) | C106—C107—C108—C109 | −0.1 (11) |
C27—C28—C29—C30 | −1.2 (10) | C107—C108—C109—C110 | 0.1 (11) |
C28—C29—C30—C25 | 0.9 (10) | C108—C109—C110—O111 | 179.3 (7) |
C26—C25—C30—C29 | 0.4 (9) | C108—C109—C110—C105 | 0.5 (10) |
C6—C25—C30—C29 | −176.9 (6) | O104—C105—C110—O111 | 0.0 (8) |
C10—C11—C32—C37 | −72.7 (7) | C106—C105—C110—O111 | 179.9 (6) |
C12—C11—C32—C37 | 106.0 (7) | O104—C105—C110—C109 | 179.0 (5) |
C10—C11—C32—C33 | 106.7 (7) | C106—C105—C110—C109 | −1.1 (9) |
C12—C11—C32—C33 | −74.6 (7) | C109—C110—O111—C112 | −2.1 (9) |
C37—C32—C33—C34 | 2.1 (8) | C105—C110—O111—C112 | 176.8 (5) |
C11—C32—C33—C34 | −177.3 (5) | C110—O111—C112—C113 | −178.1 (5) |
C32—C33—C34—C35 | −0.6 (9) | O111—C112—C113—O114 | 78.2 (7) |
C33—C34—C35—O38 | 177.7 (6) | C112—C113—O114—C115 | −93.0 (7) |
C33—C34—C35—C36 | −0.7 (9) | C113—O114—C115—C116 | −168.3 (6) |
C34—C35—C36—C37 | 0.4 (10) | O114—C115—C116—O117 | 59.9 (7) |
O38—C35—C36—C37 | −178.1 (6) | C115—C116—O117—C118 | −168.4 (5) |
C35—C36—C37—C32 | 1.2 (9) | C116—O117—C118—C119 | −110.6 (6) |
C33—C32—C37—C36 | −2.4 (9) | C89—O88—C119—C118 | −179.6 (5) |
C11—C32—C37—C36 | 177.0 (6) | O117—C118—C119—O88 | 66.2 (7) |
C17—C16—C39—C44 | −73.8 (7) | C151—O120—C121—C122 | −103.4 (7) |
C15—C16—C39—C44 | 103.5 (7) | C151—O120—C121—C126 | 79.1 (8) |
C17—C16—C39—C40 | 106.6 (7) | O120—C121—C122—C123 | −178.5 (6) |
C15—C16—C39—C40 | −76.1 (7) | C126—C121—C122—C123 | −1.0 (10) |
C44—C39—C40—C41 | 2.4 (9) | C121—C122—C123—C124 | 0.3 (10) |
C16—C39—C40—C41 | −178.0 (6) | C122—C123—C124—C125 | 0.9 (11) |
C39—C40—C41—C42 | −1.8 (9) | C123—C124—C125—C126 | −1.5 (11) |
C40—C41—C42—O45 | −177.6 (6) | C124—C125—C126—O127 | −178.8 (7) |
C40—C41—C42—C43 | 0.2 (10) | C124—C125—C126—C121 | 0.8 (10) |
O45—C42—C43—C44 | 178.6 (6) | C122—C121—C126—C125 | 0.4 (10) |
C41—C42—C43—C44 | 0.6 (10) | O120—C121—C126—C125 | 177.9 (6) |
C40—C39—C44—C43 | −1.5 (9) | C122—C121—C126—O127 | −179.9 (6) |
C16—C39—C44—C43 | 178.9 (6) | O120—C121—C126—O127 | −2.5 (9) |
C42—C43—C44—C39 | 0.0 (10) | C125—C126—O127—C128 | 13.1 (10) |
C22—C21—C46—C47 | 73.6 (8) | C121—C126—O127—C128 | −166.6 (6) |
C20—C21—C46—C47 | −104.5 (7) | C126—O127—C128—C129 | 169.3 (6) |
C22—C21—C46—C51 | −110.2 (7) | O127—C128—C129—O130 | 70.6 (8) |
C20—C21—C46—C51 | 71.8 (7) | C128—C129—O130—C131 | 77.2 (8) |
C51—C46—C47—C48 | −1.3 (9) | C129—O130—C131—C132 | 169.7 (6) |
C21—C46—C47—C48 | 175.0 (5) | O130—C131—C132—O133 | −66.5 (8) |
C46—C47—C48—C49 | −0.4 (9) | C131—C132—O133—C134 | −173.3 (6) |
C47—C48—C49—C50 | 2.6 (9) | C132—O133—C134—C135 | −171.3 (6) |
C47—C48—C49—O52 | −177.9 (5) | O133—C134—C135—O136 | 68.8 (8) |
O52—C49—C50—C51 | 177.6 (5) | C134—C135—O136—C137 | 162.3 (7) |
C48—C49—C50—C51 | −2.9 (9) | C135—O136—C137—C138 | 8.0 (11) |
C49—C50—C51—C46 | 1.1 (9) | C135—O136—C137—C142 | −172.3 (7) |
C47—C46—C51—C50 | 1.0 (9) | O136—C137—C138—C139 | −179.4 (7) |
C21—C46—C51—C50 | −175.3 (6) | C142—C137—C138—C139 | 0.9 (11) |
C10—N1—Zn53—N2 | 14.6 (5) | C137—C138—C139—C140 | 0.3 (12) |
C7—N1—Zn53—N2 | 178.5 (5) | C138—C139—C140—C141 | −2.2 (11) |
C10—N1—Zn53—N4 | 176.8 (5) | C139—C140—C141—C142 | 2.8 (11) |
C7—N1—Zn53—N4 | −19.3 (5) | C140—C141—C142—O143 | −178.4 (7) |
C10—N1—Zn53—N3 | 94.6 (7) | C140—C141—C142—C137 | −1.6 (11) |
C7—N1—Zn53—N3 | −101.4 (7) | O136—C137—C142—O143 | −3.1 (10) |
C10—N1—Zn53—O54 | −84.4 (5) | C138—C137—C142—O143 | 176.5 (7) |
C7—N1—Zn53—O54 | 79.5 (5) | O136—C137—C142—C141 | −180.0 (6) |
C12—N2—Zn53—N1 | −13.5 (5) | C138—C137—C142—C141 | −0.3 (11) |
C15—N2—Zn53—N1 | 175.7 (5) | C141—C142—O143—C144 | −113.9 (7) |
C12—N2—Zn53—N4 | −96.9 (8) | C137—C142—O143—C144 | 69.3 (8) |
C15—N2—Zn53—N4 | 92.2 (8) | C142—O143—C144—C145 | −128.7 (6) |
C12—N2—Zn53—N3 | −174.3 (5) | O143—C144—C145—O146 | −73.6 (7) |
C15—N2—Zn53—N3 | 14.8 (5) | C144—C145—O146—C147 | −174.7 (5) |
C12—N2—Zn53—O54 | 78.5 (5) | C145—O146—C147—C148 | 172.1 (5) |
C15—N2—Zn53—O54 | −92.4 (5) | O146—C147—C148—O149 | 73.6 (7) |
C5—N4—Zn53—N1 | 14.6 (5) | C147—C148—O149—C150 | 154.9 (6) |
C22—N4—Zn53—N1 | −172.0 (5) | C148—O149—C150—C151 | −83.7 (7) |
C5—N4—Zn53—N2 | 97.9 (8) | C121—O120—C151—C150 | −177.9 (6) |
C22—N4—Zn53—N2 | −88.7 (8) | O149—C150—C151—O120 | 72.8 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O31—H31···O85i | 0.78 | 2.18 | 2.878 (7) | 149 |
O31—H31···O82i | 0.78 | 2.34 | 2.875 (6) | 127 |
O38—H38···O152 | 0.96 | 1.74 | 2.688 (7) | 168 |
O45—H45···O114ii | 0.95 | 1.82 | 2.769 (6) | 180 |
O45—H45···O117ii | 0.95 | 2.61 | 3.030 (7) | 107 |
O52—H52···O154iii | 0.95 | 1.73 | 2.677 (7) | 179 |
O54—H54···O149iv | 0.94 | 1.80 | 2.740 (6) | 179 |
O152—H152···O98 | 0.94 | 1.93 | 2.872 (7) | 174 |
O154—H154···O156 | 0.93 | 1.72 | 2.651 (7) | 180 |
O156—H156···O146v | 0.95 | 1.81 | 2.755 (7) | 180 |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z+1; (iii) x, y−1, z+1; (iv) x+1, y, z+1; (v) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C44H28N4O4)]·3C24H32O8·4CH4O |
Mr | 2215.73 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 110 |
a, b, c (Å) | 10.2643 (3), 13.4878 (4), 21.1227 (8) |
α, β, γ (°) | 86.2858 (10), 77.9955 (13), 73.932 (3) |
V (Å3) | 2748.51 (15) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15453, 15453, 13092 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.167, 1.05 |
No. of reflections | 15453 |
No. of parameters | 1420 |
No. of restraints | 4 |
H-atom treatment | H-atom parameters constrained |
(Δ/σ)max | 0.136 |
Δρmax, Δρmin (e Å−3) | 0.96, −0.55 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.477 (13) |
Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski, 1985), DENZO, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.
N1—Zn53 | 2.047 (5) | N4—Zn53 | 2.081 (5) |
N2—Zn53 | 2.068 (5) | Zn53—O54 | 2.123 (4) |
N3—Zn53 | 2.081 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O31—H31···O85i | 0.78 | 2.18 | 2.878 (7) | 149 |
O31—H31···O82i | 0.78 | 2.34 | 2.875 (6) | 127 |
O38—H38···O152 | 0.96 | 1.74 | 2.688 (7) | 168 |
O45—H45···O114ii | 0.95 | 1.82 | 2.769 (6) | 180 |
O45—H45···O117ii | 0.95 | 2.61 | 3.030 (7) | 107 |
O52—H52···O154iii | 0.95 | 1.73 | 2.677 (7) | 179 |
O54—H54···O149iv | 0.94 | 1.80 | 2.740 (6) | 179 |
O152—H152···O98 | 0.94 | 1.93 | 2.872 (7) | 174 |
O154—H154···O156 | 0.93 | 1.72 | 2.651 (7) | 180 |
O156—H156···O146v | 0.95 | 1.81 | 2.755 (7) | 180 |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z+1; (iii) x, y−1, z+1; (iv) x+1, y, z+1; (v) x+1, y, z. |
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The zinc–tetrakis(4-hydroxyphenyl)porphyrin molecule, (I), has been used previously as a potential building block for the supramolecular synthesis of multiporphyrin arrays (Goldberg et al., 1995; Goldberg, 2000). The peripheral OH functional groups provide self-complementary binding sites for a simultaneous lateral association of every building block to several neighboring species by multiple hydrogen bonding. The ZnII ion in the porphyrin center may allow additional coordination in the axial direction to other ligands. A relevant example of such axial coordination of zinc– and manganese–tetraphenylporphyrin to 18-crown-6, via a water ligand bound to the metal ion, has been reported previously (Diskin-Posner et al., 1999). This report describes the extensive hydrogen bonding between the porphyrin moiety and the surrounding dibenzo-24-crown-8 species, (II), either directly or through methanol bridges, in directions parallel to the porphyrin plane, as well as perpendicular to it. The resulting structure represents a fascinating supramolecular lattice composed of three different species and held together by a co-operative array of hydrogen bonds.
The central core of the porphyrin moiety is nearly planar with only a slight puckering, the deviations of the individual atoms from the mean plane of the 24-atom macrocycle being between -0.091 (6) and 0.077 (5) Å. The ZnII ion is five-coordinate, deviating by 0.335 (3) Å from the plane of the four pyrrole N atoms towards the axial methanol ligand coordinated to it, and assuming a square-pyramidal coordination environment (shown in Fig. 3). The hydroxyphenyl rings are oriented in an almost perpendicular manner with respect to the porphyrin macrocycle, the corresponding dihedral angles being 76.2 (2), 73.4 (1), 75.6 (2) and 72.6 (2)°. The coordination bond lengths to the ZnII ion are given in Table 1. The three dibenzo-24-crown-8 species assume a roughly flat conformation (Fig. 1), with some of the methylene groups turned inward to fill the space within the macrocyclic rings. Correspondingly, while a fully open crown structure is characterized by a gauche conformation about the C—C bonds and a trans conformation about the C—O bonds, in this compound, some of the latter are also gauche. All O—C—C—O fragments preserved, however, their gauche arrangement. The molecular geometries of the constituent species are, otherwise, characterized by common features.
The supramolecular structure consists of layers of species interconnected by a network of hydrogen bonds, as shown in Fig. 2. Within a given layer, every porphyrin unit is hydrogen bonded in lateral directions to four different crown-ether moieties, either directly or through bridging methanol molecules. The direct porphyrin–crown ether interaction involves OH31···O82, OH31···O85, OH45···O114, and possibly also OH45···O117 hydrogen bonds on opposite sides of the porphyrin framework (Table 2). In the other directions, one side the porphyrin hydrogen bonds to a third crown-ether species through one methanol molecule (OH38···O152 and OH152···O98), while at the other end, it links through two methanol moieties (OH52···O154, OH154···O156 and OH156···O146; Table 2). The layers formed consist of two different rows (extending in the a-2 b direction) arranged side-by-side in an alternating manner. One row consists of crown-ether molecules only, while the other row contains paired porphyrin–crown-ether assemblies (Fig. 2). These layers are stacked along the a axis of the crystal in an offset manner, which also facilitates additional hydrogen bonding between the layers. The offset is along a-2 b by a half vector translation in order to position the crown-ether ring of one layer above the porphyrin-coordinated axial methanol ligand of another layer, and optimize the interlayer hydrogen bond, OH54···O149 (Table 2). Figs. 3 and 4 illustrate the stacking arrangement along the a axis of the crystal. The resulting structure thus contains columns of alternating porphyrin and crown-ether species, as well as separate stacks of the other crown-ether moieties (Fig. 4), all of which are interconnected to each other by the methanol bridges. The efficient intermolecular hydrogen bonding yielded a relatively well packed chiral (though the analyzed crystal represents a racemic twin) and polar structure of previously unknown supramolecular features. These results are particularly significant in the context of the crystal engineering of new supramolecular materials.