metal-organic compounds
Tetrakis(5,7-dimethylquinolin-8-olato-κ2N,O)zirconium(IV) dimethylformamide disolvate
aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
*Correspondence e-mail: steynm@ufs.ac.za
In the title compound, [Zr(C11H10NO)4]·2C3H7NO, the ZrIV ion is coordinated by four bidentate 5,7-dimethylquinolin-8-olate ligands in a slightly distorted square-antiprismatic coordination environment. The also contains two N,N′-dimethylformamide (DMF) solvent molecules. In the crystal, a weak C—H⋯O hydrogen bond links the complex molecule to a solvent molecule and weak π–π stacking interactions [centroid–centroid distance = 3.671 (3) Å] also occur. One of the DMF solvent molecules was refined as disordered over three sets of sites, with refined occupancies in the ratio of 0.391 (9):0.342 (10):0.267 (7).
Related literature
For N,O- and O,O′-bidentate ligand complexes of zirconium and hafnium, see: Calderazzo et al. (1998); Demakopoulos et al. (1995); Steyn et al. (2008, 2011); Viljoen et al. (2008, 2009a,b; 2010a,b); Zherikova et al. (2005, 2006, 2008). For our ongoing research of structure reactivity relationships in catalysis, separation chemistry and other industrial reaction mechanisms, see: Roodt et al. (2011); Schutte et al. (2011); Brink et al. (2010); Ferreira et al. (2007); Haumann et al. (2004).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812042092/lh5537sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042092/lh5537Isup2.hkl
Chemicals were purchased from Sigma-Aldrich and used as received. ZrCl4 (101.3 mg, 0.435 mmol) and 5,7-Dimethyl-8-quinolinol (diMeOxH) (228.2 mg, 1.317 mmol) was separately dissolved in DMF (2.5 ml ea) and heated to 60°C. The diMeOxH solution as added drop-wise to the zirconium solution and stirred at 333 K for 30 minutes. The reaction solution was removed from heating, covered and left to stand. Red cuboid crystals, suitable for single X-Ray diffraction, formed after 10 days. (Yield: 203 mg, 79%).
H atoms were placed inidealized positions (C—H = 0.93–0.96Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2–1.5Ueq(C). The highest residual electron density was located 0.95 Å from O102. One of the DMF solvent molecules was refined as disordered over three sets of sites with refined occupancies in a ratio of 0.391 (9):0.342 (10):0.267 (7).
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).[Zr(C11H10NO)4]·2C3H7NO | F(000) = 1936 |
Mr = 926.21 | Dx = 1.332 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 9914 reflections |
a = 15.572 (5) Å | θ = 2.6–24.6° |
b = 18.706 (5) Å | µ = 0.29 mm−1 |
c = 15.853 (5) Å | T = 100 K |
V = 4618 (2) Å3 | Cuboid, red |
Z = 4 | 0.26 × 0.14 × 0.13 mm |
Bruker APEXII CCD diffractometer | 11142 independent reflections |
Radiation source: sealed tube | 8497 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ϕ and ω scans | θmax = 28°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −20→20 |
Tmin = 0.928, Tmax = 0.963 | k = −22→24 |
61276 measured reflections | l = −20→20 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.3005P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
11142 reflections | Δρmax = 0.42 e Å−3 |
671 parameters | Δρmin = −0.39 e Å−3 |
299 restraints | Absolute structure: Flack (1983), 5375 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (3) |
[Zr(C11H10NO)4]·2C3H7NO | V = 4618 (2) Å3 |
Mr = 926.21 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 15.572 (5) Å | µ = 0.29 mm−1 |
b = 18.706 (5) Å | T = 100 K |
c = 15.853 (5) Å | 0.26 × 0.14 × 0.13 mm |
Bruker APEXII CCD diffractometer | 11142 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 8497 reflections with I > 2σ(I) |
Tmin = 0.928, Tmax = 0.963 | Rint = 0.064 |
61276 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.099 | Δρmax = 0.42 e Å−3 |
S = 1.02 | Δρmin = −0.39 e Å−3 |
11142 reflections | Absolute structure: Flack (1983), 5375 Friedel pairs |
671 parameters | Absolute structure parameter: −0.01 (3) |
299 restraints |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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) | |
Zr01 | 0.966490 (14) | 0.144904 (13) | 0.35471 (2) | 0.02304 (7) | |
N102 | 0.96042 (15) | 0.03648 (14) | 0.43981 (17) | 0.0262 (6) | |
O101 | 0.89103 (13) | 0.17184 (11) | 0.46024 (13) | 0.0297 (5) | |
O104 | 1.02836 (11) | 0.19244 (11) | 0.24980 (13) | 0.0271 (5) | |
N104 | 0.87759 (15) | 0.23775 (13) | 0.29748 (17) | 0.0262 (6) | |
O103 | 0.85773 (12) | 0.09319 (11) | 0.30675 (14) | 0.0279 (5) | |
N101 | 1.01720 (16) | 0.25663 (13) | 0.41574 (17) | 0.0294 (6) | |
N103 | 1.01035 (15) | 0.04558 (13) | 0.26899 (16) | 0.0251 (6) | |
O102 | 1.08748 (12) | 0.12297 (11) | 0.40715 (14) | 0.0271 (5) | |
C116 | 1.1890 (2) | 0.04673 (17) | 0.4780 (2) | 0.0326 (7) | |
C128 | 0.79960 (18) | 0.25709 (16) | 0.3227 (2) | 0.0295 (7) | |
H128 | 0.7761 | 0.2349 | 0.3698 | 0.035* | |
C110 | 0.8931 (2) | −0.00201 (18) | 0.4599 (2) | 0.0339 (8) | |
H110 | 0.8392 | 0.0135 | 0.4427 | 0.041* | |
C122 | 0.95422 (19) | −0.05997 (17) | 0.1978 (2) | 0.0260 (7) | |
C107 | 0.8621 (2) | 0.23826 (18) | 0.5857 (2) | 0.0352 (8) | |
C125 | 0.79013 (19) | −0.00990 (18) | 0.2458 (2) | 0.0363 (8) | |
C121 | 1.03962 (19) | −0.07799 (19) | 0.1757 (2) | 0.0320 (8) | |
H121 | 1.0504 | −0.1193 | 0.1448 | 0.038* | |
C118 | 1.03964 (18) | 0.01552 (17) | 0.46759 (19) | 0.0247 (6) | |
C111 | 0.8992 (2) | −0.0659 (2) | 0.5063 (2) | 0.0423 (9) | |
H111 | 0.8502 | −0.0922 | 0.519 | 0.051* | |
C109 | 0.97617 (19) | 0.27293 (17) | 0.4900 (2) | 0.0291 (7) | |
C120 | 1.1060 (2) | −0.03520 (18) | 0.1995 (2) | 0.0352 (8) | |
H120 | 1.1621 | −0.0464 | 0.1841 | 0.042* | |
C114 | 1.1373 (2) | −0.06654 (18) | 0.5408 (2) | 0.0332 (8) | |
C117 | 1.10771 (19) | 0.06285 (17) | 0.4490 (2) | 0.0278 (7) | |
C129 | 0.75120 (19) | 0.30983 (17) | 0.2808 (2) | 0.0348 (8) | |
H129 | 0.6965 | 0.3216 | 0.2997 | 0.042* | |
C119 | 1.0886 (2) | 0.02635 (18) | 0.2479 (2) | 0.0307 (7) | |
H119 | 1.1344 | 0.0545 | 0.2657 | 0.037* | |
C134 | 1.03493 (19) | 0.27832 (19) | 0.1369 (2) | 0.0355 (8) | |
C127 | 0.94307 (19) | 0.00394 (16) | 0.2438 (2) | 0.0251 (7) | |
C135 | 0.9944 (2) | 0.24636 (17) | 0.2046 (2) | 0.0270 (7) | |
C131 | 0.8681 (2) | 0.32476 (19) | 0.1829 (2) | 0.0343 (7) | |
C112 | 0.9788 (2) | −0.0889 (2) | 0.5328 (2) | 0.0389 (9) | |
H112 | 0.9837 | −0.1313 | 0.563 | 0.047* | |
C115 | 1.2008 (2) | −0.01833 (18) | 0.5218 (2) | 0.0381 (8) | |
H115 | 1.2562 | −0.0294 | 0.5391 | 0.046* | |
C101 | 1.0838 (2) | 0.29617 (16) | 0.3917 (2) | 0.0341 (8) | |
H101 | 1.1107 | 0.2859 | 0.3407 | 0.041* | |
C113 | 1.0527 (2) | −0.04862 (17) | 0.5143 (2) | 0.0296 (7) | |
C102 | 1.1149 (2) | 0.35297 (18) | 0.4411 (3) | 0.0429 (9) | |
H102 | 1.1621 | 0.3794 | 0.4231 | 0.051* | |
C104 | 1.0026 (2) | 0.32912 (19) | 0.5431 (3) | 0.0400 (9) | |
C136 | 0.91150 (19) | 0.27068 (17) | 0.2282 (2) | 0.0294 (7) | |
C14B | 1.1235 (2) | 0.2566 (2) | 0.1106 (2) | 0.0412 (9) | |
H14A | 1.165 | 0.2818 | 0.1441 | 0.062* | |
H14B | 1.1318 | 0.268 | 0.0521 | 0.062* | |
H14C | 1.1304 | 0.2061 | 0.1187 | 0.062* | |
C133 | 0.9898 (3) | 0.3325 (2) | 0.0928 (3) | 0.0465 (10) | |
H133 | 1.0169 | 0.3534 | 0.0467 | 0.056* | |
C126 | 0.86090 (18) | 0.03010 (16) | 0.2668 (2) | 0.0272 (7) | |
C12A | 1.1540 (2) | −0.13471 (18) | 0.5890 (2) | 0.0427 (9) | |
H12A | 1.2146 | −0.1402 | 0.5978 | 0.064* | |
H12B | 1.1327 | −0.1747 | 0.5572 | 0.064* | |
H12C | 1.1252 | −0.1327 | 0.6425 | 0.064* | |
C124 | 0.8028 (2) | −0.07534 (18) | 0.2024 (2) | 0.0428 (9) | |
H124 | 0.7545 | −0.1024 | 0.1897 | 0.051* | |
C108 | 0.9078 (2) | 0.22615 (17) | 0.5113 (2) | 0.0302 (7) | |
C103 | 1.0751 (2) | 0.36913 (19) | 0.5161 (3) | 0.0460 (10) | |
H103 | 1.0957 | 0.4064 | 0.5492 | 0.055* | |
C13A | 0.8899 (2) | −0.17105 (18) | 0.1312 (3) | 0.0425 (9) | |
H13A | 0.8342 | −0.1914 | 0.1216 | 0.064* | |
H13B | 0.924 | −0.2035 | 0.164 | 0.064* | |
H13C | 0.9176 | −0.1625 | 0.078 | 0.064* | |
C106 | 0.8905 (2) | 0.2956 (2) | 0.6375 (2) | 0.0469 (10) | |
H106 | 0.8612 | 0.303 | 0.6878 | 0.056* | |
C11B | 0.7879 (2) | 0.1918 (2) | 0.6073 (2) | 0.0416 (9) | |
H11A | 0.7388 | 0.206 | 0.5747 | 0.062* | |
H11B | 0.775 | 0.1966 | 0.6663 | 0.062* | |
H11C | 0.8018 | 0.143 | 0.595 | 0.062* | |
C105 | 0.9568 (3) | 0.3407 (2) | 0.6200 (3) | 0.0506 (12) | |
C13B | 0.7013 (2) | 0.0169 (2) | 0.2666 (3) | 0.0574 (12) | |
H13D | 0.6854 | 0.001 | 0.322 | 0.086* | |
H13E | 0.6611 | −0.0014 | 0.2261 | 0.086* | |
H13F | 0.7008 | 0.0682 | 0.2649 | 0.086* | |
C12B | 1.2621 (2) | 0.09893 (19) | 0.4674 (3) | 0.0428 (9) | |
H12D | 1.2882 | 0.092 | 0.4131 | 0.064* | |
H12E | 1.304 | 0.091 | 0.5108 | 0.064* | |
H12F | 1.2406 | 0.1469 | 0.4714 | 0.064* | |
C14A | 0.8651 (3) | 0.4165 (3) | 0.0639 (3) | 0.0684 (14) | |
H14D | 0.9045 | 0.4356 | 0.0231 | 0.103* | |
H14E | 0.848 | 0.4536 | 0.1022 | 0.103* | |
H14F | 0.8154 | 0.398 | 0.0356 | 0.103* | |
C130 | 0.7850 (2) | 0.34339 (18) | 0.2126 (2) | 0.0377 (8) | |
H130 | 0.7536 | 0.3787 | 0.1852 | 0.045* | |
C123 | 0.8805 (2) | −0.10150 (17) | 0.1781 (2) | 0.0328 (8) | |
C132 | 0.9089 (3) | 0.3563 (2) | 0.1132 (3) | 0.0496 (10) | |
C11A | 0.9852 (3) | 0.3981 (3) | 0.6804 (3) | 0.0790 (17) | |
H11D | 0.976 | 0.4442 | 0.6553 | 0.119* | |
H11E | 1.0451 | 0.3922 | 0.6929 | 0.119* | |
H11F | 0.9525 | 0.3946 | 0.7316 | 0.119* | |
N201 | 0.5982 (2) | 0.0128 (2) | 0.8446 (3) | 0.0738 (11) | |
C202 | 0.5442 (3) | −0.0454 (3) | 0.8137 (3) | 0.0685 (13) | |
H20A | 0.5562 | −0.0537 | 0.7551 | 0.103* | |
H20B | 0.4848 | −0.0326 | 0.8202 | 0.103* | |
H20C | 0.5559 | −0.088 | 0.8453 | 0.103* | |
C203 | 0.5743 (5) | 0.0405 (5) | 0.9247 (5) | 0.144 (3) | |
H20D | 0.6092 | 0.0813 | 0.9377 | 0.216* | |
H20E | 0.5824 | 0.0045 | 0.9671 | 0.216* | |
H20F | 0.515 | 0.0545 | 0.9235 | 0.216* | |
C201 | 0.6631 (3) | 0.0338 (3) | 0.7986 (5) | 0.0925 (18) | |
H201 | 0.696 | 0.0695 | 0.8237 | 0.111* | |
O201 | 0.6878 (2) | 0.0165 (2) | 0.7320 (3) | 0.0958 (13) | |
N31 | 0.372 (2) | 0.2574 (12) | 0.8644 (9) | 0.142 (6) | 0.342 (10) |
C31A | 0.464 (2) | 0.2579 (16) | 0.8591 (10) | 0.141 (8) | 0.342 (10) |
H31A | 0.485 | 0.2097 | 0.8564 | 0.211* | 0.342 (10) |
H31B | 0.4875 | 0.2811 | 0.908 | 0.211* | 0.342 (10) |
H31C | 0.4815 | 0.2833 | 0.8093 | 0.211* | 0.342 (10) |
C31B | 0.331 (2) | 0.3202 (14) | 0.8686 (13) | 0.158 (9) | 0.342 (10) |
H31D | 0.3721 | 0.3585 | 0.8649 | 0.237* | 0.342 (10) |
H31E | 0.3009 | 0.3234 | 0.9212 | 0.237* | 0.342 (10) |
H31F | 0.2911 | 0.3237 | 0.8228 | 0.237* | 0.342 (10) |
C31C | 0.3383 (19) | 0.1890 (12) | 0.8670 (13) | 0.151 (6) | 0.342 (10) |
H31J | 0.2808 | 0.1767 | 0.874 | 0.181* | 0.342 (10) |
O31 | 0.4022 (14) | 0.1459 (8) | 0.8578 (11) | 0.169 (7) | 0.342 (10) |
N32 | 0.5527 (18) | 0.2747 (12) | 0.8555 (18) | 0.163 (8) | 0.267 (7) |
C32B | 0.476 (2) | 0.3148 (16) | 0.848 (3) | 0.171 (10) | 0.267 (7) |
H32A | 0.489 | 0.3627 | 0.8307 | 0.257* | 0.267 (7) |
H32B | 0.4464 | 0.3157 | 0.9011 | 0.257* | 0.267 (7) |
H32C | 0.4392 | 0.2929 | 0.8062 | 0.257* | 0.267 (7) |
C32C | 0.546 (2) | 0.2060 (11) | 0.8783 (12) | 0.169 (10) | 0.267 (7) |
H32D | 0.4869 | 0.1931 | 0.8826 | 0.253* | 0.267 (7) |
H32E | 0.5738 | 0.1992 | 0.932 | 0.253* | 0.267 (7) |
H32F | 0.5738 | 0.1765 | 0.8368 | 0.253* | 0.267 (7) |
C32A | 0.6322 (19) | 0.3019 (16) | 0.841 (2) | 0.198 (11) | 0.267 (7) |
H32J | 0.6379 | 0.3497 | 0.8257 | 0.238* | 0.267 (7) |
O32 | 0.6989 (19) | 0.2633 (15) | 0.8475 (15) | 0.237 (12) | 0.267 (7) |
N33 | 0.3685 (14) | 0.2750 (9) | 0.8788 (12) | 0.127 (5) | 0.391 (9) |
C33A | 0.4579 (15) | 0.2793 (11) | 0.8624 (16) | 0.112 (6) | 0.391 (9) |
H33A | 0.4857 | 0.2372 | 0.8836 | 0.167* | 0.391 (9) |
H33B | 0.4811 | 0.3207 | 0.8899 | 0.167* | 0.391 (9) |
H33C | 0.4672 | 0.2829 | 0.8027 | 0.167* | 0.391 (9) |
C33C | 0.3514 (15) | 0.2052 (7) | 0.9044 (9) | 0.122 (6) | 0.391 (9) |
H33D | 0.4044 | 0.1812 | 0.9166 | 0.183* | 0.391 (9) |
H33E | 0.3217 | 0.1803 | 0.8603 | 0.183* | 0.391 (9) |
H33F | 0.3163 | 0.2061 | 0.9542 | 0.183* | 0.391 (9) |
C33B | 0.3106 (17) | 0.3250 (11) | 0.8571 (17) | 0.130 (6) | 0.391 (9) |
H33J | 0.3285 | 0.3643 | 0.8258 | 0.156* | 0.391 (9) |
O33 | 0.2314 (12) | 0.3201 (7) | 0.8785 (8) | 0.142 (6) | 0.391 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zr01 | 0.01669 (11) | 0.02212 (12) | 0.03031 (13) | 0.00031 (10) | −0.00125 (16) | −0.00248 (17) |
N102 | 0.0214 (13) | 0.0287 (15) | 0.0285 (15) | 0.0003 (11) | 0.0024 (11) | −0.0051 (12) |
O101 | 0.0275 (11) | 0.0256 (11) | 0.0360 (13) | 0.0039 (9) | 0.0014 (9) | −0.0050 (10) |
O104 | 0.0177 (10) | 0.0272 (11) | 0.0365 (12) | −0.0001 (8) | −0.0009 (9) | −0.0015 (10) |
N104 | 0.0174 (11) | 0.0264 (13) | 0.0347 (15) | 0.0011 (10) | −0.0020 (10) | −0.0047 (12) |
O103 | 0.0164 (9) | 0.0280 (11) | 0.0393 (12) | 0.0005 (8) | −0.0008 (9) | −0.0068 (10) |
N101 | 0.0253 (13) | 0.0243 (13) | 0.0387 (16) | 0.0033 (10) | −0.0082 (11) | −0.0033 (12) |
N103 | 0.0167 (12) | 0.0252 (14) | 0.0335 (15) | 0.0006 (10) | 0.0018 (11) | −0.0004 (12) |
O102 | 0.0196 (10) | 0.0249 (11) | 0.0370 (12) | 0.0015 (8) | −0.0035 (9) | −0.0004 (10) |
C116 | 0.0258 (16) | 0.0304 (18) | 0.0415 (19) | 0.0009 (13) | −0.0038 (14) | 0.0018 (15) |
C128 | 0.0205 (14) | 0.0276 (16) | 0.0403 (17) | 0.0005 (12) | 0.0012 (12) | −0.0038 (13) |
C110 | 0.0227 (16) | 0.042 (2) | 0.0371 (19) | 0.0007 (14) | 0.0033 (14) | 0.0016 (16) |
C122 | 0.0219 (15) | 0.0226 (16) | 0.0334 (17) | 0.0000 (12) | −0.0004 (13) | −0.0030 (14) |
C107 | 0.0315 (17) | 0.041 (2) | 0.0326 (18) | 0.0204 (15) | −0.0063 (14) | −0.0057 (16) |
C125 | 0.0208 (15) | 0.0357 (19) | 0.052 (2) | −0.0039 (13) | 0.0038 (14) | −0.0126 (17) |
C121 | 0.0267 (17) | 0.032 (2) | 0.037 (2) | 0.0015 (14) | 0.0043 (14) | −0.0106 (16) |
C118 | 0.0213 (15) | 0.0269 (16) | 0.0258 (16) | 0.0031 (12) | 0.0046 (13) | −0.0007 (13) |
C111 | 0.0301 (18) | 0.044 (2) | 0.053 (2) | −0.0066 (16) | 0.0078 (17) | 0.0118 (19) |
C109 | 0.0299 (17) | 0.0240 (17) | 0.0334 (18) | 0.0102 (13) | −0.0109 (14) | −0.0072 (14) |
C120 | 0.0206 (15) | 0.040 (2) | 0.045 (2) | 0.0000 (14) | 0.0039 (14) | −0.0122 (17) |
C114 | 0.0279 (16) | 0.0340 (19) | 0.0377 (19) | 0.0061 (14) | −0.0001 (14) | 0.0048 (16) |
C117 | 0.0276 (15) | 0.0256 (17) | 0.0300 (16) | 0.0041 (13) | 0.0012 (13) | −0.0007 (14) |
C129 | 0.0192 (15) | 0.0328 (18) | 0.053 (2) | 0.0029 (13) | −0.0028 (15) | −0.0011 (17) |
C119 | 0.0221 (15) | 0.0333 (19) | 0.0368 (19) | −0.0022 (13) | 0.0018 (14) | −0.0028 (15) |
C134 | 0.0251 (16) | 0.044 (2) | 0.0375 (18) | −0.0005 (15) | −0.0014 (14) | 0.0034 (16) |
C127 | 0.0203 (14) | 0.0277 (17) | 0.0274 (17) | −0.0025 (13) | 0.0007 (12) | −0.0033 (14) |
C135 | 0.0213 (14) | 0.0269 (18) | 0.0328 (17) | 0.0000 (13) | −0.0055 (13) | −0.0013 (14) |
C131 | 0.0293 (16) | 0.0392 (19) | 0.0346 (19) | 0.0025 (14) | −0.0048 (14) | 0.0047 (16) |
C112 | 0.0347 (19) | 0.034 (2) | 0.048 (2) | 0.0044 (15) | 0.0082 (16) | 0.0074 (17) |
C115 | 0.0284 (16) | 0.038 (2) | 0.048 (2) | 0.0093 (15) | −0.0040 (15) | 0.0039 (17) |
C101 | 0.0267 (16) | 0.0250 (16) | 0.050 (2) | 0.0008 (13) | −0.0088 (14) | −0.0022 (15) |
C113 | 0.0319 (17) | 0.0268 (18) | 0.0302 (18) | 0.0027 (14) | 0.0051 (14) | −0.0002 (15) |
C102 | 0.0318 (17) | 0.0267 (18) | 0.070 (3) | 0.0012 (14) | −0.0184 (18) | −0.0057 (18) |
C104 | 0.0320 (17) | 0.0313 (18) | 0.057 (2) | 0.0131 (16) | −0.0177 (17) | −0.0137 (18) |
C136 | 0.0231 (15) | 0.0304 (18) | 0.0346 (18) | −0.0037 (13) | −0.0023 (13) | −0.0026 (15) |
C14B | 0.0279 (16) | 0.052 (2) | 0.043 (2) | 0.0004 (15) | 0.0011 (15) | 0.0115 (18) |
C133 | 0.041 (2) | 0.060 (3) | 0.039 (2) | 0.008 (2) | 0.0059 (19) | 0.019 (2) |
C126 | 0.0219 (14) | 0.0234 (16) | 0.0363 (18) | −0.0006 (12) | 0.0017 (13) | −0.0039 (14) |
C12A | 0.0377 (19) | 0.039 (2) | 0.052 (2) | 0.0090 (16) | −0.0012 (17) | 0.0084 (18) |
C124 | 0.0273 (17) | 0.038 (2) | 0.063 (2) | −0.0136 (15) | −0.0015 (16) | −0.0142 (19) |
C108 | 0.0289 (16) | 0.0291 (17) | 0.0324 (17) | 0.0119 (13) | −0.0084 (14) | −0.0044 (15) |
C103 | 0.0329 (19) | 0.034 (2) | 0.071 (3) | 0.0071 (15) | −0.0234 (19) | −0.0204 (19) |
C13A | 0.0358 (19) | 0.0308 (18) | 0.061 (2) | −0.0058 (15) | −0.0002 (17) | −0.0134 (18) |
C106 | 0.041 (2) | 0.062 (3) | 0.037 (2) | 0.029 (2) | −0.0102 (16) | −0.0189 (19) |
C11B | 0.0334 (18) | 0.056 (2) | 0.0352 (19) | 0.0199 (17) | −0.0002 (15) | −0.0069 (18) |
C105 | 0.044 (2) | 0.054 (3) | 0.054 (3) | 0.0193 (19) | −0.020 (2) | −0.031 (2) |
C13B | 0.0236 (17) | 0.056 (2) | 0.093 (3) | −0.0054 (16) | −0.0032 (19) | −0.030 (2) |
C12B | 0.0256 (16) | 0.043 (2) | 0.060 (2) | −0.0029 (15) | −0.0115 (16) | 0.0133 (19) |
C14A | 0.056 (3) | 0.089 (4) | 0.061 (3) | 0.032 (2) | 0.006 (2) | 0.033 (3) |
C130 | 0.0277 (16) | 0.040 (2) | 0.045 (2) | 0.0102 (14) | −0.0068 (15) | 0.0014 (17) |
C123 | 0.0296 (16) | 0.0275 (18) | 0.041 (2) | −0.0038 (14) | 0.0031 (14) | −0.0047 (15) |
C132 | 0.041 (2) | 0.062 (3) | 0.046 (2) | 0.0135 (19) | 0.0007 (18) | 0.017 (2) |
C11A | 0.056 (3) | 0.092 (4) | 0.089 (4) | 0.020 (3) | −0.021 (3) | −0.064 (3) |
N201 | 0.0424 (18) | 0.081 (2) | 0.098 (3) | 0.0171 (18) | 0.001 (2) | 0.007 (3) |
C202 | 0.041 (2) | 0.080 (3) | 0.084 (3) | 0.003 (2) | −0.001 (2) | 0.010 (3) |
C203 | 0.094 (5) | 0.185 (8) | 0.154 (7) | 0.070 (5) | −0.007 (5) | −0.073 (6) |
C201 | 0.049 (3) | 0.090 (4) | 0.138 (5) | 0.010 (3) | 0.004 (3) | 0.013 (4) |
O201 | 0.0446 (19) | 0.112 (3) | 0.131 (4) | 0.0012 (19) | 0.018 (2) | 0.028 (3) |
N31 | 0.285 (12) | 0.108 (10) | 0.034 (7) | 0.057 (10) | 0.031 (9) | −0.024 (9) |
C31A | 0.296 (17) | 0.070 (15) | 0.055 (11) | −0.019 (14) | 0.002 (15) | 0.018 (12) |
C31B | 0.310 (19) | 0.106 (14) | 0.058 (13) | 0.036 (16) | −0.054 (15) | −0.004 (12) |
C31C | 0.301 (14) | 0.100 (11) | 0.052 (10) | 0.057 (11) | 0.030 (12) | 0.010 (11) |
O31 | 0.293 (19) | 0.149 (12) | 0.064 (7) | 0.061 (12) | 0.002 (15) | 0.001 (10) |
N32 | 0.31 (2) | 0.136 (15) | 0.047 (9) | 0.014 (16) | 0.053 (16) | 0.010 (12) |
C32B | 0.34 (2) | 0.13 (2) | 0.045 (13) | −0.03 (2) | 0.010 (19) | −0.013 (18) |
C32C | 0.38 (3) | 0.095 (15) | 0.032 (11) | 0.051 (19) | 0.061 (15) | 0.000 (10) |
C32A | 0.35 (2) | 0.17 (2) | 0.071 (15) | 0.027 (19) | 0.043 (19) | 0.029 (15) |
O32 | 0.39 (3) | 0.26 (3) | 0.061 (11) | 0.14 (2) | −0.011 (18) | 0.060 (16) |
N33 | 0.261 (11) | 0.078 (8) | 0.043 (7) | 0.057 (9) | 0.005 (8) | −0.020 (7) |
C33A | 0.243 (15) | 0.049 (12) | 0.043 (10) | −0.032 (11) | 0.019 (12) | −0.018 (9) |
C33C | 0.307 (17) | 0.030 (7) | 0.029 (7) | 0.007 (9) | −0.020 (10) | −0.005 (6) |
C33B | 0.267 (14) | 0.083 (9) | 0.040 (7) | 0.059 (11) | −0.025 (11) | −0.009 (9) |
O33 | 0.236 (15) | 0.097 (8) | 0.094 (10) | 0.040 (11) | −0.001 (10) | 0.003 (7) |
Zr01—O103 | 2.093 (2) | C12A—H12A | 0.96 |
Zr01—O102 | 2.100 (2) | C12A—H12B | 0.96 |
Zr01—O101 | 2.106 (2) | C12A—H12C | 0.96 |
Zr01—O104 | 2.118 (2) | C124—C123 | 1.360 (4) |
Zr01—N104 | 2.399 (2) | C124—H124 | 0.93 |
Zr01—N103 | 2.401 (3) | C103—H103 | 0.93 |
Zr01—N101 | 2.435 (3) | C13A—C123 | 1.505 (5) |
Zr01—N102 | 2.438 (3) | C13A—H13A | 0.96 |
N102—C110 | 1.310 (4) | C13A—H13B | 0.96 |
N102—C118 | 1.367 (4) | C13A—H13C | 0.96 |
O101—C108 | 1.325 (4) | C106—C105 | 1.361 (6) |
O104—C135 | 1.345 (4) | C106—H106 | 0.93 |
N104—C128 | 1.329 (4) | C11B—H11A | 0.96 |
N104—C136 | 1.365 (4) | C11B—H11B | 0.96 |
O103—C126 | 1.340 (4) | C11B—H11C | 0.96 |
N101—C101 | 1.330 (4) | C105—C11A | 1.506 (6) |
N101—C109 | 1.374 (4) | C13B—H13D | 0.96 |
N103—C119 | 1.314 (4) | C13B—H13E | 0.96 |
N103—C127 | 1.365 (4) | C13B—H13F | 0.96 |
O102—C117 | 1.343 (4) | C12B—H12D | 0.96 |
C116—C117 | 1.380 (4) | C12B—H12E | 0.96 |
C116—C115 | 1.413 (5) | C12B—H12F | 0.96 |
C116—C12B | 1.510 (4) | C14A—C132 | 1.531 (5) |
C128—C129 | 1.408 (4) | C14A—H14D | 0.96 |
C128—H128 | 0.93 | C14A—H14E | 0.96 |
C110—C111 | 1.407 (5) | C14A—H14F | 0.96 |
C110—H110 | 0.93 | C130—H130 | 0.93 |
C122—C127 | 1.412 (4) | C11A—H11D | 0.96 |
C122—C121 | 1.416 (4) | C11A—H11E | 0.96 |
C122—C123 | 1.421 (4) | C11A—H11F | 0.96 |
C107—C108 | 1.395 (5) | N201—C201 | 1.307 (7) |
C107—C106 | 1.422 (5) | N201—C203 | 1.422 (8) |
C107—C11B | 1.486 (5) | N201—C202 | 1.461 (6) |
C125—C126 | 1.373 (4) | C202—H20A | 0.96 |
C125—C124 | 1.418 (5) | C202—H20B | 0.96 |
C125—C13B | 1.508 (4) | C202—H20C | 0.96 |
C121—C120 | 1.361 (4) | C203—H20D | 0.96 |
C121—H121 | 0.93 | C203—H20E | 0.96 |
C118—C117 | 1.412 (4) | C203—H20F | 0.96 |
C118—C113 | 1.424 (5) | C201—O201 | 1.169 (7) |
C111—C112 | 1.377 (5) | C201—H201 | 0.93 |
C111—H111 | 0.93 | N31—C31B | 1.341 (17) |
C109—C104 | 1.408 (5) | N31—C31C | 1.387 (17) |
C109—C108 | 1.419 (5) | N31—C31A | 1.430 (16) |
C120—C119 | 1.410 (5) | C31A—H31A | 0.96 |
C120—H120 | 0.93 | C31A—H31B | 0.96 |
C114—C115 | 1.372 (4) | C31A—H31C | 0.96 |
C114—C113 | 1.424 (4) | C31B—H31D | 0.96 |
C114—C12A | 1.509 (5) | C31B—H31E | 0.96 |
C129—C130 | 1.356 (5) | C31B—H31F | 0.96 |
C129—H129 | 0.93 | C31C—O31 | 1.29 (2) |
C119—H119 | 0.93 | C31C—H31J | 0.93 |
C134—C135 | 1.381 (5) | N32—C32C | 1.338 (17) |
C134—C133 | 1.417 (5) | N32—C32A | 1.359 (18) |
C134—C14B | 1.497 (4) | N32—C32B | 1.422 (18) |
C127—C126 | 1.417 (4) | C32B—H32A | 0.96 |
C135—C136 | 1.419 (4) | C32B—H32B | 0.96 |
C131—C132 | 1.405 (5) | C32B—H32C | 0.96 |
C131—C136 | 1.413 (4) | C32C—H32D | 0.96 |
C131—C130 | 1.421 (4) | C32C—H32E | 0.96 |
C112—C113 | 1.406 (5) | C32C—H32F | 0.96 |
C112—H112 | 0.93 | C32A—O32 | 1.27 (2) |
C115—H115 | 0.93 | C32A—H32J | 0.93 |
C101—C102 | 1.406 (5) | N33—C33B | 1.343 (16) |
C101—H101 | 0.93 | N33—C33C | 1.392 (15) |
C102—C103 | 1.375 (6) | N33—C33A | 1.418 (15) |
C102—H102 | 0.93 | C33A—H33A | 0.96 |
C104—C103 | 1.421 (6) | C33A—H33B | 0.96 |
C104—C105 | 1.428 (6) | C33A—H33C | 0.96 |
C14B—H14A | 0.96 | C33C—H33D | 0.96 |
C14B—H14B | 0.96 | C33C—H33E | 0.96 |
C14B—H14C | 0.96 | C33C—H33F | 0.96 |
C133—C132 | 1.374 (5) | C33B—O33 | 1.28 (2) |
C133—H133 | 0.93 | C33B—H33J | 0.93 |
O103—Zr01—O102 | 141.21 (8) | H12A—C12A—H12B | 109.5 |
O103—Zr01—O101 | 87.00 (8) | C114—C12A—H12C | 109.5 |
O102—Zr01—O101 | 103.47 (9) | H12A—C12A—H12C | 109.5 |
O103—Zr01—O104 | 106.07 (8) | H12B—C12A—H12C | 109.5 |
O102—Zr01—O104 | 89.13 (8) | C123—C124—C125 | 124.9 (3) |
O101—Zr01—O104 | 141.02 (8) | C123—C124—H124 | 117.5 |
O103—Zr01—N104 | 74.36 (8) | C125—C124—H124 | 117.5 |
O102—Zr01—N104 | 143.99 (8) | O101—C108—C107 | 122.7 (3) |
O101—Zr01—N104 | 78.77 (9) | O101—C108—C109 | 118.3 (3) |
O104—Zr01—N104 | 70.22 (8) | C107—C108—C109 | 118.9 (3) |
O103—Zr01—N103 | 70.55 (8) | C102—C103—C104 | 120.3 (3) |
O102—Zr01—N103 | 79.49 (8) | C102—C103—H103 | 119.9 |
O101—Zr01—N103 | 142.52 (8) | C104—C103—H103 | 119.9 |
O104—Zr01—N103 | 75.58 (8) | C123—C13A—H13A | 109.5 |
N104—Zr01—N103 | 120.68 (9) | C123—C13A—H13B | 109.5 |
O103—Zr01—N101 | 143.46 (8) | H13A—C13A—H13B | 109.5 |
O102—Zr01—N101 | 73.70 (8) | C123—C13A—H13C | 109.5 |
O101—Zr01—N101 | 70.11 (9) | H13A—C13A—H13C | 109.5 |
O104—Zr01—N101 | 78.70 (9) | H13B—C13A—H13C | 109.5 |
N104—Zr01—N101 | 73.50 (8) | C105—C106—C107 | 125.9 (4) |
N103—Zr01—N101 | 142.84 (8) | C105—C106—H106 | 117.1 |
O103—Zr01—N102 | 77.60 (8) | C107—C106—H106 | 117.1 |
O102—Zr01—N102 | 69.70 (8) | C107—C11B—H11A | 109.5 |
O101—Zr01—N102 | 74.80 (8) | C107—C11B—H11B | 109.5 |
O104—Zr01—N102 | 143.28 (8) | H11A—C11B—H11B | 109.5 |
N104—Zr01—N102 | 142.11 (8) | C107—C11B—H11C | 109.5 |
N103—Zr01—N102 | 71.36 (8) | H11A—C11B—H11C | 109.5 |
N101—Zr01—N102 | 120.46 (9) | H11B—C11B—H11C | 109.5 |
C110—N102—C118 | 119.1 (3) | C106—C105—C104 | 117.3 (4) |
C110—N102—Zr01 | 128.5 (2) | C106—C105—C11A | 122.3 (4) |
C118—N102—Zr01 | 112.45 (19) | C104—C105—C11A | 120.3 (4) |
C108—O101—Zr01 | 124.0 (2) | C125—C13B—H13D | 109.5 |
C135—O104—Zr01 | 123.64 (18) | C125—C13B—H13E | 109.5 |
C128—N104—C136 | 118.2 (3) | H13D—C13B—H13E | 109.5 |
C128—N104—Zr01 | 127.7 (2) | C125—C13B—H13F | 109.5 |
C136—N104—Zr01 | 114.05 (18) | H13D—C13B—H13F | 109.5 |
C126—O103—Zr01 | 123.28 (17) | H13E—C13B—H13F | 109.5 |
C101—N101—C109 | 119.0 (3) | C116—C12B—H12D | 109.5 |
C101—N101—Zr01 | 128.1 (2) | C116—C12B—H12E | 109.5 |
C109—N101—Zr01 | 112.3 (2) | H12D—C12B—H12E | 109.5 |
C119—N103—C127 | 118.8 (3) | C116—C12B—H12F | 109.5 |
C119—N103—Zr01 | 128.3 (2) | H12D—C12B—H12F | 109.5 |
C127—N103—Zr01 | 112.86 (19) | H12E—C12B—H12F | 109.5 |
C117—O102—Zr01 | 124.72 (18) | C132—C14A—H14D | 109.5 |
C117—C116—C115 | 118.1 (3) | C132—C14A—H14E | 109.5 |
C117—C116—C12B | 120.9 (3) | H14D—C14A—H14E | 109.5 |
C115—C116—C12B | 120.9 (3) | C132—C14A—H14F | 109.5 |
N104—C128—C129 | 122.6 (3) | H14D—C14A—H14F | 109.5 |
N104—C128—H128 | 118.7 | H14E—C14A—H14F | 109.5 |
C129—C128—H128 | 118.7 | C129—C130—C131 | 120.3 (3) |
N102—C110—C111 | 122.7 (3) | C129—C130—H130 | 119.9 |
N102—C110—H110 | 118.7 | C131—C130—H130 | 119.9 |
C111—C110—H110 | 118.7 | C124—C123—C122 | 117.3 (3) |
C127—C122—C121 | 116.4 (3) | C124—C123—C13A | 122.5 (3) |
C127—C122—C123 | 118.5 (3) | C122—C123—C13A | 120.1 (3) |
C121—C122—C123 | 125.1 (3) | C133—C132—C131 | 117.6 (3) |
C108—C107—C106 | 116.8 (3) | C133—C132—C14A | 121.8 (4) |
C108—C107—C11B | 119.8 (3) | C131—C132—C14A | 120.6 (3) |
C106—C107—C11B | 123.4 (3) | C105—C11A—H11D | 109.5 |
C126—C125—C124 | 118.4 (3) | C105—C11A—H11E | 109.5 |
C126—C125—C13B | 120.1 (3) | H11D—C11A—H11E | 109.5 |
C124—C125—C13B | 121.4 (3) | C105—C11A—H11F | 109.5 |
C120—C121—C122 | 120.3 (3) | H11D—C11A—H11F | 109.5 |
C120—C121—H121 | 119.8 | H11E—C11A—H11F | 109.5 |
C122—C121—H121 | 119.8 | C201—N201—C203 | 126.3 (6) |
N102—C118—C117 | 115.5 (3) | C201—N201—C202 | 118.9 (5) |
N102—C118—C113 | 122.5 (3) | C203—N201—C202 | 114.9 (5) |
C117—C118—C113 | 122.0 (3) | N201—C202—H20A | 109.5 |
C112—C111—C110 | 119.0 (3) | N201—C202—H20B | 109.5 |
C112—C111—H111 | 120.5 | H20A—C202—H20B | 109.5 |
C110—C111—H111 | 120.5 | N201—C202—H20C | 109.5 |
N101—C109—C104 | 122.8 (3) | H20A—C202—H20C | 109.5 |
N101—C109—C108 | 114.6 (3) | H20B—C202—H20C | 109.5 |
C104—C109—C108 | 122.5 (3) | N201—C203—H20D | 109.5 |
C121—C120—C119 | 119.0 (3) | N201—C203—H20E | 109.5 |
C121—C120—H120 | 120.5 | H20D—C203—H20E | 109.5 |
C119—C120—H120 | 120.5 | N201—C203—H20F | 109.5 |
C115—C114—C113 | 116.5 (3) | H20D—C203—H20F | 109.5 |
C115—C114—C12A | 122.9 (3) | H20E—C203—H20F | 109.5 |
C113—C114—C12A | 120.5 (3) | O201—C201—N201 | 132.4 (7) |
O102—C117—C116 | 124.3 (3) | O201—C201—H201 | 113.8 |
O102—C117—C118 | 116.9 (3) | N201—C201—H201 | 113.8 |
C116—C117—C118 | 118.8 (3) | C31B—N31—C31C | 129 (2) |
C130—C129—C128 | 119.5 (3) | C31B—N31—C31A | 118.4 (19) |
C130—C129—H129 | 120.2 | C31C—N31—C31A | 113.1 (16) |
C128—C129—H129 | 120.2 | N31—C31A—H31A | 109.5 |
N103—C119—C120 | 122.7 (3) | N31—C31A—H31B | 109.5 |
N103—C119—H119 | 118.6 | H31A—C31A—H31B | 109.5 |
C120—C119—H119 | 118.6 | N31—C31A—H31C | 109.5 |
C135—C134—C133 | 117.8 (3) | H31A—C31A—H31C | 109.5 |
C135—C134—C14B | 121.3 (3) | H31B—C31A—H31C | 109.5 |
C133—C134—C14B | 120.9 (3) | N31—C31B—H31D | 109.5 |
N103—C127—C122 | 122.7 (3) | N31—C31B—H31E | 109.5 |
N103—C127—C126 | 114.9 (3) | H31D—C31B—H31E | 109.5 |
C122—C127—C126 | 122.4 (3) | N31—C31B—H31F | 109.5 |
O104—C135—C134 | 124.0 (3) | H31D—C31B—H31F | 109.5 |
O104—C135—C136 | 117.2 (3) | H31E—C31B—H31F | 109.5 |
C134—C135—C136 | 118.8 (3) | O31—C31C—N31 | 106.0 (18) |
C132—C131—C136 | 119.0 (3) | O31—C31C—H31J | 127 |
C132—C131—C130 | 124.7 (3) | N31—C31C—H31J | 127 |
C136—C131—C130 | 116.3 (3) | C32C—N32—C32A | 118.3 (18) |
C111—C112—C113 | 120.4 (4) | C32C—N32—C32B | 117.8 (19) |
C111—C112—H112 | 119.8 | C32A—N32—C32B | 123.9 (19) |
C113—C112—H112 | 119.8 | N32—C32B—H32A | 109.5 |
C114—C115—C116 | 125.5 (3) | N32—C32B—H32B | 109.5 |
C114—C115—H115 | 117.2 | H32A—C32B—H32B | 109.5 |
C116—C115—H115 | 117.2 | N32—C32B—H32C | 109.5 |
N101—C101—C102 | 122.0 (3) | H32A—C32B—H32C | 109.5 |
N101—C101—H101 | 119 | H32B—C32B—H32C | 109.5 |
C102—C101—H101 | 119 | N32—C32C—H32D | 109.5 |
C112—C113—C114 | 124.7 (3) | N32—C32C—H32E | 109.5 |
C112—C113—C118 | 116.3 (3) | H32D—C32C—H32E | 109.5 |
C114—C113—C118 | 118.9 (3) | N32—C32C—H32F | 109.5 |
C103—C102—C101 | 119.5 (3) | H32D—C32C—H32F | 109.5 |
C103—C102—H102 | 120.3 | H32E—C32C—H32F | 109.5 |
C101—C102—H102 | 120.3 | O32—C32A—N32 | 121 (3) |
C109—C104—C103 | 116.4 (3) | O32—C32A—H32J | 119.4 |
C109—C104—C105 | 118.5 (4) | N32—C32A—H32J | 119.4 |
C103—C104—C105 | 125.1 (3) | C33B—N33—C33C | 126.8 (17) |
N104—C136—C131 | 123.2 (3) | C33B—N33—C33A | 124.9 (17) |
N104—C136—C135 | 114.8 (3) | C33C—N33—C33A | 107.1 (14) |
C131—C136—C135 | 122.0 (3) | N33—C33A—H33A | 109.5 |
C134—C14B—H14A | 109.5 | N33—C33A—H33B | 109.5 |
C134—C14B—H14B | 109.5 | H33A—C33A—H33B | 109.5 |
H14A—C14B—H14B | 109.5 | N33—C33A—H33C | 109.5 |
C134—C14B—H14C | 109.5 | H33A—C33A—H33C | 109.5 |
H14A—C14B—H14C | 109.5 | H33B—C33A—H33C | 109.5 |
H14B—C14B—H14C | 109.5 | N33—C33C—H33D | 109.5 |
C132—C133—C134 | 124.8 (4) | N33—C33C—H33E | 109.5 |
C132—C133—H133 | 117.6 | H33D—C33C—H33E | 109.5 |
C134—C133—H133 | 117.6 | N33—C33C—H33F | 109.5 |
O103—C126—C125 | 124.4 (3) | H33D—C33C—H33F | 109.5 |
O103—C126—C127 | 117.3 (2) | H33E—C33C—H33F | 109.5 |
C125—C126—C127 | 118.3 (3) | O33—C33B—N33 | 122 (2) |
C114—C12A—H12A | 109.5 | O33—C33B—H33J | 119.1 |
C114—C12A—H12B | 109.5 | N33—C33B—H33J | 119.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
C14A—H14E···O201i | 0.96 | 2.43 | 3.358 (7) | 161 |
Symmetry code: (i) −x+3/2, y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zr(C11H10NO)4]·2C3H7NO |
Mr | 926.21 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 100 |
a, b, c (Å) | 15.572 (5), 18.706 (5), 15.853 (5) |
V (Å3) | 4618 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.26 × 0.14 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.928, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 61276, 11142, 8497 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.099, 1.02 |
No. of reflections | 11142 |
No. of parameters | 671 |
No. of restraints | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.39 |
Absolute structure | Flack (1983), 5375 Friedel pairs |
Absolute structure parameter | −0.01 (3) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C14A—H14E···O201i | 0.96 | 2.43 | 3.358 (7) | 161.3 |
Symmetry code: (i) −x+3/2, y+1/2, z−1/2. |
Acknowledgements
Financial assistance from the Advanced Metals Initiative (AMI) and the Department of Science and Technology (DST) of South Africa, as well as the New Metals Development Network (NMDN) and the South African Nuclear Energy Corporation Limited (Necsa), is gratefully acknowledged.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
This study forms part of our ongoing research of structure reactivity relationships in catalysis, separation chemistry and other industrial reaction mechanisms including radio pharmacy (Roodt et al. 2011; Schutte et al. 2011; Brink et al. 2010; Ferreira et al. 2007; Haumann et al. 2004; Steyn et al. 2008, 2011; Viljoen et al. 2008, 2009a,b, 2010a,b).
The asymmetric unit of the title compound, [Zr(C10H11NO)4].2C3H7NO, with C10H11NO (diMeOx) = 5,7-Dimethyl-8-quinolinol, consists of a ZrIV ion coordinated to four bidentate ligands (diMeOx), as well as two N,N'-dimethylformamide (DMF) solvent molecules. In the complex molecule (Fig. 1) the ZrIV ion lies at the centre of an approximate square antiprismatic coordination polyhedron of the N,O-coordination ligand atoms, with a small distortion towards dodecahedral geometry. The Zr—N and Zr—O bond distances range from 2.094 (2) to 2.117 (2) Å and 2.398 (2) to 2.438 (2) Å, respectively. The N—Zr—O bite angles range from 69.70 (8)° to 70.55 (8)°.
In the crystal, a weak C—H···O hydrogen bond connects the complex molecule to a solvent molecule (Table 1). In addition, weak π–π interactions exist between the pyridine rings of the diMeOx ligand and symmetry related molecules (1 - x, 1 - y, 1/2 + z) , with interplanar and centroid-to-centroid distances of 3.433 (4) Å and 3.671 (3) Å, respectively (Figure 2).