


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812042092/lh5537sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536812042092/lh5537Isup2.hkl |
CCDC reference: 909719
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.041
- wR factor = 0.099
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT214_ALERT_2_C Atom N31 (Anion/Solvent) ADP max/min Ratio 4.1 prola PLAT214_ALERT_2_C Atom C32C (Anion/Solvent) ADP max/min Ratio 4.4 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.2 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of N201 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 11142 Count of symmetry unique reflns 5780 Completeness (_total/calc) 192.77% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 5362 Fraction of Friedel pairs measured 0.928 Are heavy atom types Z>Si present yes PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 15 PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites .... 20 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of N32 PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 50 Perc. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 1 PLAT794_ALERT_5_G Note: Tentative Bond Valency for Zr01 (IV) 4.23 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 299 PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) ... 1
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
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 refinement: 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. |
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).