Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704682X/at2404sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704682X/at2404Isup2.hkl |
CCDC reference: 656318
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.011 Å
- Disorder in main residue
- R factor = 0.040
- wR factor = 0.100
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.08 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.46 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O10 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O12 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C97 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Chen & Cai (2005); Liu et al. (2007); Zhou et al. (2004).
To a stirred solution of 1-naphthylacetic acid (0.5586 g, 3 mmol) and 1,10-phenanthroline monohydrate (0.198 g, 1 mmol) in 30 ml me thanol, and a solution of Pr(NO3)3.6H2O (0.453 g, 1 mmol) in water (10 ml) was added. The mixed solution was heated to 333 K and stirred for 3 h, and then cooled to room temperature. The precipitate was washed with water and then dissolved in DMF. A colorless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution [m.p. 548–549 K].
The space group was uniquely assigned from the systematic absences. All H atoms were located in difference Fourier maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl, formyl), 0.97 Å (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) (aryl, formyl, methylene) or 1.5Ueq(C) (methyl). The NNA ligand bridged to Pr2 were found to be disordered over two sites. The coordinates of these two sites were refined with the occupancies tied to sum to unity, the site occupancies for C50–C60 with attached H atoms and C50'–C60' with attached H atoms refined to 0.565 (17) and 0.435 (17), respectively.
Rare earth complexes with aromatic carboxylic acids are a kind of luminescent materials with good properties (Zhou et al., 2004). Generally, an organic negative ligand acts as the first ligand to the central ion while a neutral secondary ligand acts as to saturate the coordination number of the rare earth ion and also to improve the fluorescence intensity and stability of the complex. Based on this reason, some rare earth complexes with 1-naphthylacetic acid (NNA) and 1,10-phenanthroline (phen) have been synthesized (Chen & Cai, 2005), however, no report on crystal structures of rare earth complexes with NNA and phen can be found in the literature. Here, we report the synthesis and crystal structure of complex, (I).
In(I), the asymmetric unit consists of two half molecule (A and B) and one N, N-dimethylformamide (DMF) solvate. Each half molecule have a symmetric center on the central Pr—Pr bond. Each PrIII ion is nine-coordinated and the stereochemistry each PrIII ion can be described as a distorted monocapped square antiprismatic geometry (Fig. 1). The coordination modes of NNA ligands coordinated to the PrIII ion is consistent with reported Eu complex (Liu et al., 2007). The Pr1—O bond distances are 2.431 (3)–2.619 (4) Å, longer than that 2.423 (4)–2.561 (4) Å of Pr2—O. The dihedral angles between the least square-plane Pr2O2 and naphthyl rings are 42.19 (16)–71.32 (11)° for molecule A and 49.74 (16)–58.51 (16)° for molecule B.
The two molecules of (I) are linked into a chain running parallel to the [011] plane by means of C—H···π hydrogen bond and π···π stacking interaction (Fig. 2 and Table 2). The phen rings (N2C42—C46) in the molecules at (x, y, z) are inclined to one another (N3C85—C89) in the molecules at (1 - x, 1 - y, 1 - z), the separation of the two rings centroids is 3.944 (3) Å, the dihedral angles between the two rings is 2.95°. In the same way, two molecules are linked into two chains parallel to the a axis direction by C—H···O hydrogen bonds (Fig. 3 and Table 2), and these two a chains are linked into sheets parallel to the [011] plane by [011] chain. The DMF solvate molecules lie in between two sheets. However, there are no direction-specific interactions between adjacent sheets.
For related literature, see: Chen & Cai (2005); Liu et al. (2007); Zhou et al. (2004).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
[Pr2(C12H9O2)6(C12H8N2)2]·C3H7NO | Z = 2 |
Mr = 1826.48 | F(000) = 1856 |
Triclinic, P1 | Dx = 1.470 Mg m−3 |
Hall symbol: -P 1 | Melting point: 549 K |
a = 13.0204 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.1379 (19) Å | Cell parameters from 7370 reflections |
c = 20.417 (3) Å | θ = 2.2–28.0° |
α = 66.336 (2)° | µ = 1.24 mm−1 |
β = 81.554 (2)° | T = 298 K |
γ = 85.998 (3)° | Block, colourless |
V = 4127.2 (8) Å3 | 0.49 × 0.45 × 0.22 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 14351 independent reflections |
Radiation source: fine-focus sealed tube | 9934 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.583, Tmax = 0.773 | k = −20→20 |
21619 measured reflections | l = −24→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0262P)2 + 6.9332P] where P = (Fo2 + 2Fc2)/3 |
14351 reflections | (Δ/σ)max = 0.001 |
1174 parameters | Δρmax = 1.56 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
[Pr2(C12H9O2)6(C12H8N2)2]·C3H7NO | γ = 85.998 (3)° |
Mr = 1826.48 | V = 4127.2 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.0204 (12) Å | Mo Kα radiation |
b = 17.1379 (19) Å | µ = 1.24 mm−1 |
c = 20.417 (3) Å | T = 298 K |
α = 66.336 (2)° | 0.49 × 0.45 × 0.22 mm |
β = 81.554 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 14351 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 9934 reflections with I > 2σ(I) |
Tmin = 0.583, Tmax = 0.773 | Rint = 0.023 |
21619 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.56 e Å−3 |
14351 reflections | Δρmin = −0.75 e Å−3 |
1174 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Pr1 | 0.12209 (2) | 0.995948 (16) | 0.050714 (15) | 0.03165 (9) | |
Pr2 | 0.61837 (2) | 0.479311 (17) | 0.559170 (16) | 0.03783 (9) | |
N1 | 0.3126 (3) | 1.0448 (2) | 0.0495 (2) | 0.0357 (10) | |
N2 | 0.2593 (3) | 0.8769 (2) | 0.1157 (2) | 0.0393 (10) | |
N3 | 0.7446 (3) | 0.3471 (3) | 0.6218 (2) | 0.0468 (12) | |
N4 | 0.8110 (3) | 0.5107 (3) | 0.5657 (2) | 0.0432 (11) | |
N5 | 0.1828 (6) | 0.6340 (5) | 0.8451 (4) | 0.099 (2) | |
O1 | 0.0207 (3) | 0.8661 (2) | 0.1040 (2) | 0.0484 (10) | |
O2 | −0.1304 (3) | 0.8736 (2) | 0.06167 (19) | 0.0413 (9) | |
O3 | 0.0595 (2) | 0.9601 (2) | −0.05013 (19) | 0.0415 (9) | |
O4 | 0.2236 (3) | 0.9351 (2) | −0.0366 (2) | 0.0455 (9) | |
O5 | 0.1096 (3) | 1.1156 (2) | 0.0882 (2) | 0.0443 (9) | |
O6 | 0.1111 (3) | 0.9911 (2) | 0.17795 (19) | 0.0497 (10) | |
O7 | 0.6377 (3) | 0.6161 (2) | 0.4558 (2) | 0.0515 (10) | |
O8 | 0.4972 (3) | 0.6407 (2) | 0.3992 (2) | 0.0556 (11) | |
O9 | 0.5565 (3) | 0.4583 (2) | 0.44969 (19) | 0.0449 (9) | |
O10 | 0.7190 (3) | 0.4295 (3) | 0.4650 (2) | 0.0589 (11) | |
O11 | 0.6152 (3) | 0.5839 (2) | 0.6199 (2) | 0.0491 (10) | |
O12 | 0.5853 (3) | 0.4502 (2) | 0.6906 (2) | 0.0561 (10) | |
O13 | 0.0657 (6) | 0.7409 (4) | 0.8256 (4) | 0.138 (3) | |
C1 | −0.0614 (4) | 0.8342 (3) | 0.0990 (3) | 0.0403 (13) | |
C2 | −0.0705 (4) | 0.7390 (3) | 0.1442 (3) | 0.0557 (17) | |
H2A | −0.0168 | 0.7102 | 0.1235 | 0.067* | |
H2B | −0.0552 | 0.7286 | 0.1921 | 0.067* | |
C3 | −0.1725 (4) | 0.6973 (3) | 0.1523 (4) | 0.0511 (16) | |
C4 | −0.2372 (5) | 0.6764 (3) | 0.2155 (4) | 0.0630 (19) | |
H4 | −0.2177 | 0.6882 | 0.2526 | 0.076* | |
C5 | −0.3339 (5) | 0.6369 (4) | 0.2258 (5) | 0.080 (2) | |
H5 | −0.3779 | 0.6235 | 0.2690 | 0.096* | |
C6 | −0.3611 (6) | 0.6190 (4) | 0.1723 (5) | 0.077 (2) | |
H6 | −0.4243 | 0.5929 | 0.1792 | 0.093* | |
C7 | −0.2979 (5) | 0.6383 (4) | 0.1073 (5) | 0.068 (2) | |
C8 | −0.2007 (5) | 0.6772 (3) | 0.0963 (4) | 0.0567 (17) | |
C9 | −0.1370 (6) | 0.6946 (4) | 0.0303 (4) | 0.073 (2) | |
H9 | −0.0733 | 0.7205 | 0.0221 | 0.088* | |
C10 | −0.1679 (8) | 0.6738 (5) | −0.0228 (5) | 0.094 (3) | |
H10 | −0.1245 | 0.6843 | −0.0658 | 0.112* | |
C11 | −0.2634 (8) | 0.6374 (5) | −0.0114 (6) | 0.101 (3) | |
H11 | −0.2850 | 0.6258 | −0.0480 | 0.121* | |
C12 | −0.3264 (7) | 0.6181 (4) | 0.0513 (6) | 0.091 (3) | |
H12 | −0.3891 | 0.5914 | 0.0582 | 0.110* | |
C13 | 0.1470 (4) | 0.9284 (3) | −0.0640 (3) | 0.0352 (12) | |
C14 | 0.1551 (4) | 0.8837 (4) | −0.1148 (3) | 0.0525 (15) | |
H14A | 0.0974 | 0.8449 | −0.1000 | 0.063* | |
H14B | 0.1470 | 0.9261 | −0.1626 | 0.063* | |
C15 | 0.2532 (5) | 0.8346 (4) | −0.1201 (3) | 0.0540 (16) | |
C16 | 0.3254 (5) | 0.8645 (4) | −0.1791 (4) | 0.074 (2) | |
H16 | 0.3132 | 0.9159 | −0.2168 | 0.088* | |
C17 | 0.4196 (6) | 0.8186 (5) | −0.1847 (5) | 0.092 (3) | |
H17 | 0.4679 | 0.8396 | −0.2259 | 0.110* | |
C18 | 0.4380 (7) | 0.7460 (6) | −0.1308 (5) | 0.094 (3) | |
H18 | 0.5009 | 0.7179 | −0.1346 | 0.113* | |
C19 | 0.3683 (6) | 0.7100 (5) | −0.0695 (5) | 0.078 (2) | |
C20 | 0.2743 (5) | 0.7559 (4) | −0.0639 (4) | 0.0601 (17) | |
C21 | 0.2015 (6) | 0.7193 (5) | −0.0014 (4) | 0.083 (2) | |
H21 | 0.1407 | 0.7491 | 0.0042 | 0.100* | |
C22 | 0.2188 (8) | 0.6414 (6) | 0.0507 (5) | 0.115 (3) | |
H22 | 0.1688 | 0.6168 | 0.0903 | 0.138* | |
C23 | 0.3133 (9) | 0.5987 (6) | 0.0437 (6) | 0.121 (3) | |
H23 | 0.3250 | 0.5459 | 0.0798 | 0.145* | |
C24 | 0.3866 (8) | 0.6307 (6) | −0.0124 (6) | 0.105 (3) | |
H24 | 0.4492 | 0.6015 | −0.0142 | 0.126* | |
C25 | 0.1147 (4) | 1.0706 (3) | 0.1537 (3) | 0.0412 (13) | |
C26 | 0.1283 (5) | 1.1189 (4) | 0.1990 (3) | 0.0603 (17) | |
H26A | 0.1867 | 1.1566 | 0.1753 | 0.072* | |
H26B | 0.0671 | 1.1546 | 0.1990 | 0.072* | |
C27 | 0.1455 (5) | 1.0692 (4) | 0.2756 (3) | 0.0552 (16) | |
C28 | 0.0668 (6) | 1.0653 (5) | 0.3276 (4) | 0.078 (2) | |
H28 | 0.0036 | 1.0915 | 0.3147 | 0.094* | |
C29 | 0.0780 (7) | 1.0229 (5) | 0.4002 (4) | 0.100 (3) | |
H29 | 0.0219 | 1.0197 | 0.4351 | 0.120* | |
C30 | 0.1702 (7) | 0.9862 (5) | 0.4208 (4) | 0.096 (3) | |
H30 | 0.1767 | 0.9584 | 0.4696 | 0.115* | |
C31 | 0.2567 (6) | 0.9898 (4) | 0.3686 (4) | 0.0705 (19) | |
C32 | 0.2429 (5) | 1.0310 (3) | 0.2948 (3) | 0.0527 (15) | |
C33 | 0.3289 (5) | 1.0341 (4) | 0.2432 (4) | 0.0626 (17) | |
H33 | 0.3220 | 1.0604 | 0.1944 | 0.075* | |
C34 | 0.4221 (6) | 0.9989 (4) | 0.2640 (4) | 0.080 (2) | |
H34 | 0.4779 | 1.0013 | 0.2292 | 0.095* | |
C35 | 0.4345 (6) | 0.9597 (5) | 0.3363 (5) | 0.085 (2) | |
H35 | 0.4987 | 0.9365 | 0.3497 | 0.102* | |
C36 | 0.3542 (7) | 0.9549 (5) | 0.3873 (4) | 0.085 (2) | |
H36 | 0.3634 | 0.9279 | 0.4357 | 0.102* | |
C37 | 0.3381 (4) | 1.1259 (3) | 0.0189 (3) | 0.0455 (14) | |
H37 | 0.2880 | 1.1657 | −0.0026 | 0.055* | |
C38 | 0.4362 (4) | 1.1552 (4) | 0.0170 (3) | 0.0529 (15) | |
H38 | 0.4508 | 1.2130 | −0.0054 | 0.063* | |
C39 | 0.5104 (4) | 1.0977 (3) | 0.0484 (3) | 0.0493 (15) | |
H39 | 0.5763 | 1.1160 | 0.0477 | 0.059* | |
C40 | 0.4867 (4) | 1.0112 (3) | 0.0818 (3) | 0.0407 (13) | |
C41 | 0.3850 (4) | 0.9869 (3) | 0.0815 (3) | 0.0351 (12) | |
C42 | 0.3580 (4) | 0.8988 (3) | 0.1164 (3) | 0.0361 (12) | |
C43 | 0.4328 (4) | 0.8383 (3) | 0.1496 (3) | 0.0459 (14) | |
C44 | 0.4026 (5) | 0.7529 (4) | 0.1819 (3) | 0.0629 (18) | |
H44 | 0.4493 | 0.7108 | 0.2052 | 0.075* | |
C45 | 0.3067 (5) | 0.7315 (4) | 0.1795 (4) | 0.068 (2) | |
H45 | 0.2871 | 0.6746 | 0.1997 | 0.082* | |
C46 | 0.2364 (4) | 0.7955 (3) | 0.1462 (3) | 0.0555 (16) | |
H46 | 0.1697 | 0.7798 | 0.1456 | 0.067* | |
C47 | 0.5607 (4) | 0.9471 (4) | 0.1153 (3) | 0.0513 (15) | |
H47 | 0.6278 | 0.9628 | 0.1151 | 0.062* | |
C48 | 0.5351 (4) | 0.8657 (4) | 0.1467 (3) | 0.0540 (16) | |
H48 | 0.5851 | 0.8253 | 0.1675 | 0.065* | |
C49 | 0.5690 (5) | 0.6637 (3) | 0.4221 (4) | 0.0569 (17) | |
C50 | 0.5590 (13) | 0.7485 (10) | 0.4309 (9) | 0.056 (4) | 0.565 (17) |
H50A | 0.5266 | 0.7895 | 0.3908 | 0.067* | 0.565 (17) |
H50B | 0.5118 | 0.7405 | 0.4745 | 0.067* | 0.565 (17) |
C51 | 0.6573 (11) | 0.7879 (7) | 0.4350 (10) | 0.066 (5) | 0.565 (17) |
C52 | 0.678 (2) | 0.786 (2) | 0.501 (2) | 0.073 (7) | 0.565 (17) |
H52 | 0.6326 | 0.7588 | 0.5423 | 0.088* | 0.565 (17) |
C53 | 0.767 (4) | 0.823 (3) | 0.504 (3) | 0.086 (9) | 0.565 (17) |
H53 | 0.7814 | 0.8219 | 0.5477 | 0.103* | 0.565 (17) |
C54 | 0.8356 (18) | 0.8634 (11) | 0.4415 (13) | 0.082 (6) | 0.565 (17) |
H54 | 0.8953 | 0.8887 | 0.4437 | 0.098* | 0.565 (17) |
C55 | 0.81 (2) | 0.87 (3) | 0.38 (4) | 0.07 (4) | 0.565 (17) |
C56 | 0.726 (3) | 0.8280 (19) | 0.373 (2) | 0.070 (9) | 0.565 (17) |
C57 | 0.705 (10) | 0.830 (7) | 0.307 (5) | 0.07 (2) | 0.565 (17) |
H57 | 0.6450 | 0.8051 | 0.3049 | 0.089* | 0.565 (17) |
C58 | 0.773 (6) | 0.870 (4) | 0.245 (4) | 0.082 (11) | 0.565 (17) |
H58 | 0.7589 | 0.8719 | 0.2009 | 0.098* | 0.565 (17) |
C59 | 0.862 (2) | 0.9081 (12) | 0.2480 (15) | 0.076 (5) | 0.565 (17) |
H59 | 0.9077 | 0.9349 | 0.2063 | 0.091* | 0.565 (17) |
C60 | 0.883 (6) | 0.906 (5) | 0.314 (5) | 0.079 (15) | 0.565 (17) |
H60 | 0.9426 | 0.9310 | 0.3158 | 0.095* | 0.565 (17) |
C50' | 0.5756 (18) | 0.7602 (14) | 0.3866 (15) | 0.076 (7) | 0.435 (17) |
H50C | 0.5431 | 0.7782 | 0.3430 | 0.091* | 0.435 (17) |
H50D | 0.5322 | 0.7820 | 0.4186 | 0.091* | 0.435 (17) |
C51' | 0.678 (2) | 0.8062 (15) | 0.366 (2) | 0.063 (8) | 0.435 (17) |
C52' | 0.701 (12) | 0.839 (9) | 0.291 (7) | 0.071 (17) | 0.435 (17) |
H52' | 0.6569 | 0.8301 | 0.2636 | 0.085* | 0.435 (17) |
C53' | 0.791 (8) | 0.887 (5) | 0.258 (5) | 0.084 (19) | 0.435 (17) |
H53' | 0.8063 | 0.9090 | 0.2085 | 0.101* | 0.435 (17) |
C54' | 0.857 (7) | 0.901 (7) | 0.300 (7) | 0.08 (2) | 0.435 (17) |
H54' | 0.9168 | 0.9323 | 0.2780 | 0.095* | 0.435 (17) |
C55' | 0.83 (3) | 0.87 (4) | 0.37 (5) | 0.07 (4) | 0.435 (17) |
C56' | 0.744 (3) | 0.820 (2) | 0.4078 (18) | 0.065 (10) | 0.435 (17) |
C57' | 0.721 (3) | 0.787 (3) | 0.482 (2) | 0.071 (9) | 0.435 (17) |
H57' | 0.6608 | 0.7553 | 0.5045 | 0.085* | 0.435 (17) |
C58' | 0.787 (5) | 0.801 (4) | 0.524 (3) | 0.082 (11) | 0.435 (17) |
H58' | 0.7713 | 0.7786 | 0.5741 | 0.099* | 0.435 (17) |
C59' | 0.8764 (18) | 0.8481 (12) | 0.4911 (14) | 0.085 (7) | 0.435 (17) |
H59' | 0.9207 | 0.8575 | 0.5190 | 0.102* | 0.435 (17) |
C60' | 0.900 (2) | 0.8814 (13) | 0.4164 (15) | 0.085 (8) | 0.435 (17) |
H60' | 0.9596 | 0.9131 | 0.3943 | 0.102* | 0.435 (17) |
C61 | 0.6451 (4) | 0.4323 (3) | 0.4321 (3) | 0.0463 (14) | |
C62 | 0.6600 (5) | 0.4080 (4) | 0.3675 (3) | 0.0651 (18) | |
H62A | 0.5921 | 0.4019 | 0.3561 | 0.078* | |
H62B | 0.6943 | 0.4546 | 0.3265 | 0.078* | |
C63 | 0.7217 (6) | 0.3276 (4) | 0.3764 (4) | 0.0670 (18) | |
C64 | 0.8262 (6) | 0.3303 (5) | 0.3708 (4) | 0.087 (2) | |
H64 | 0.8570 | 0.3815 | 0.3621 | 0.104* | |
C65 | 0.8903 (7) | 0.2583 (7) | 0.3776 (5) | 0.107 (3) | |
H65 | 0.9620 | 0.2621 | 0.3741 | 0.129* | |
C66 | 0.8471 (8) | 0.1848 (6) | 0.3891 (5) | 0.104 (3) | |
H66 | 0.8894 | 0.1370 | 0.3953 | 0.125* | |
C67 | 0.7403 (8) | 0.1776 (5) | 0.3919 (4) | 0.086 (2) | |
C68 | 0.6755 (7) | 0.2490 (5) | 0.3873 (4) | 0.076 (2) | |
C69 | 0.5687 (8) | 0.2395 (6) | 0.3915 (5) | 0.103 (3) | |
H69 | 0.5237 | 0.2850 | 0.3885 | 0.124* | |
C70 | 0.5295 (9) | 0.1619 (7) | 0.4000 (5) | 0.123 (3) | |
H70 | 0.4584 | 0.1565 | 0.4022 | 0.148* | |
C71 | 0.5936 (11) | 0.0935 (7) | 0.4051 (6) | 0.131 (4) | |
H71 | 0.5647 | 0.0420 | 0.4126 | 0.157* | |
C72 | 0.6962 (10) | 0.0987 (6) | 0.3997 (5) | 0.115 (3) | |
H72 | 0.7388 | 0.0524 | 0.4008 | 0.138* | |
C73 | 0.5973 (4) | 0.5263 (4) | 0.6812 (3) | 0.0436 (13) | |
C74 | 0.5883 (5) | 0.5483 (4) | 0.7469 (3) | 0.0586 (16) | |
H74A | 0.5219 | 0.5765 | 0.7508 | 0.070* | |
H74B | 0.5884 | 0.4957 | 0.7895 | 0.070* | |
C75 | 0.6728 (5) | 0.6044 (4) | 0.7460 (3) | 0.0579 (16) | |
C76 | 0.6530 (6) | 0.6847 (4) | 0.7422 (4) | 0.079 (2) | |
H76 | 0.5858 | 0.7066 | 0.7378 | 0.095* | |
C77 | 0.7314 (7) | 0.7362 (5) | 0.7448 (5) | 0.096 (3) | |
H77 | 0.7165 | 0.7917 | 0.7405 | 0.115* | |
C78 | 0.8276 (7) | 0.7036 (5) | 0.7533 (4) | 0.093 (3) | |
H78 | 0.8781 | 0.7373 | 0.7565 | 0.111* | |
C79 | 0.8557 (6) | 0.6214 (4) | 0.7578 (4) | 0.073 (2) | |
C80 | 0.7764 (5) | 0.5717 (4) | 0.7524 (3) | 0.0566 (16) | |
C81 | 0.8067 (5) | 0.4909 (4) | 0.7536 (3) | 0.0586 (16) | |
H81 | 0.7573 | 0.4576 | 0.7487 | 0.070* | |
C82 | 0.9048 (6) | 0.4590 (5) | 0.7616 (4) | 0.075 (2) | |
H82 | 0.9215 | 0.4055 | 0.7614 | 0.090* | |
C83 | 0.9794 (6) | 0.5064 (6) | 0.7700 (4) | 0.090 (2) | |
H83 | 1.0458 | 0.4838 | 0.7774 | 0.108* | |
C84 | 0.9566 (6) | 0.5845 (5) | 0.7674 (4) | 0.086 (2) | |
H84 | 1.0083 | 0.6160 | 0.7721 | 0.103* | |
C85 | 0.7135 (5) | 0.2679 (4) | 0.6493 (4) | 0.0624 (18) | |
H85 | 0.6451 | 0.2578 | 0.6472 | 0.075* | |
C86 | 0.7772 (5) | 0.1976 (4) | 0.6817 (4) | 0.073 (2) | |
H86 | 0.7514 | 0.1426 | 0.7009 | 0.088* | |
C87 | 0.8769 (5) | 0.2113 (4) | 0.6845 (4) | 0.0696 (19) | |
H87 | 0.9204 | 0.1654 | 0.7058 | 0.083* | |
C88 | 0.9150 (4) | 0.2937 (4) | 0.6555 (3) | 0.0558 (16) | |
C89 | 0.8441 (4) | 0.3610 (3) | 0.6246 (3) | 0.0457 (14) | |
C90 | 0.8805 (4) | 0.4468 (3) | 0.5951 (3) | 0.0455 (14) | |
C91 | 0.9848 (4) | 0.4636 (4) | 0.5956 (3) | 0.0495 (14) | |
C92 | 1.0153 (5) | 0.5487 (4) | 0.5667 (3) | 0.0596 (17) | |
H92 | 1.0838 | 0.5619 | 0.5658 | 0.072* | |
C93 | 0.9452 (5) | 0.6123 (4) | 0.5399 (3) | 0.0590 (17) | |
H93 | 0.9643 | 0.6691 | 0.5218 | 0.071* | |
C94 | 0.8437 (4) | 0.5901 (4) | 0.5403 (3) | 0.0536 (16) | |
H94 | 0.7963 | 0.6338 | 0.5215 | 0.064* | |
C95 | 1.0201 (5) | 0.3140 (4) | 0.6553 (3) | 0.0650 (18) | |
H95 | 1.0663 | 0.2699 | 0.6759 | 0.078* | |
C96 | 1.0533 (5) | 0.3934 (4) | 0.6267 (3) | 0.0609 (17) | |
H96 | 1.1225 | 0.4038 | 0.6267 | 0.073* | |
C97 | 0.1487 (8) | 0.7123 (6) | 0.8099 (5) | 0.101 (3) | |
H97 | 0.1918 | 0.7480 | 0.7701 | 0.121* | |
C98 | 0.1213 (9) | 0.5751 (7) | 0.9091 (6) | 0.147 (4) | |
H98A | 0.0559 | 0.6013 | 0.9172 | 0.220* | |
H98B | 0.1579 | 0.5606 | 0.9500 | 0.220* | |
H98C | 0.1096 | 0.5243 | 0.9023 | 0.220* | |
C99 | 0.2810 (8) | 0.6042 (6) | 0.8222 (5) | 0.138 (4) | |
H99A | 0.3172 | 0.6505 | 0.7831 | 0.207* | |
H99B | 0.2704 | 0.5600 | 0.8064 | 0.207* | |
H99C | 0.3213 | 0.5821 | 0.8617 | 0.207* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pr1 | 0.02479 (16) | 0.03391 (15) | 0.03961 (18) | −0.00079 (11) | −0.01051 (12) | −0.01585 (13) |
Pr2 | 0.02723 (17) | 0.03939 (17) | 0.0509 (2) | 0.00106 (12) | −0.01346 (14) | −0.01950 (15) |
N1 | 0.026 (2) | 0.036 (2) | 0.044 (3) | −0.0047 (17) | −0.0098 (19) | −0.013 (2) |
N2 | 0.035 (2) | 0.036 (2) | 0.047 (3) | −0.0018 (18) | −0.012 (2) | −0.015 (2) |
N3 | 0.038 (3) | 0.042 (3) | 0.062 (3) | 0.004 (2) | −0.016 (2) | −0.020 (2) |
N4 | 0.032 (2) | 0.047 (3) | 0.054 (3) | 0.000 (2) | −0.015 (2) | −0.021 (2) |
N5 | 0.124 (6) | 0.083 (5) | 0.109 (6) | 0.023 (5) | −0.051 (5) | −0.049 (5) |
O1 | 0.038 (2) | 0.043 (2) | 0.059 (3) | −0.0084 (16) | −0.0179 (18) | −0.0106 (18) |
O2 | 0.038 (2) | 0.0351 (19) | 0.048 (2) | −0.0036 (15) | −0.0131 (18) | −0.0108 (17) |
O3 | 0.026 (2) | 0.049 (2) | 0.057 (2) | 0.0024 (15) | −0.0086 (17) | −0.0282 (19) |
O4 | 0.029 (2) | 0.058 (2) | 0.061 (3) | 0.0034 (16) | −0.0105 (18) | −0.034 (2) |
O5 | 0.047 (2) | 0.040 (2) | 0.049 (2) | 0.0006 (16) | −0.0127 (18) | −0.0182 (18) |
O6 | 0.067 (3) | 0.037 (2) | 0.049 (2) | −0.0036 (18) | −0.010 (2) | −0.0204 (18) |
O7 | 0.038 (2) | 0.046 (2) | 0.069 (3) | −0.0053 (17) | −0.017 (2) | −0.018 (2) |
O8 | 0.050 (2) | 0.043 (2) | 0.073 (3) | −0.0067 (18) | −0.022 (2) | −0.015 (2) |
O9 | 0.032 (2) | 0.052 (2) | 0.059 (3) | 0.0064 (16) | −0.0128 (18) | −0.0296 (19) |
O10 | 0.035 (2) | 0.085 (3) | 0.069 (3) | 0.015 (2) | −0.017 (2) | −0.043 (2) |
O11 | 0.050 (2) | 0.046 (2) | 0.055 (3) | −0.0044 (18) | −0.007 (2) | −0.023 (2) |
O12 | 0.064 (3) | 0.049 (2) | 0.057 (3) | −0.0070 (19) | −0.009 (2) | −0.021 (2) |
O13 | 0.129 (6) | 0.125 (5) | 0.204 (8) | 0.056 (4) | −0.078 (5) | −0.101 (5) |
C1 | 0.033 (3) | 0.038 (3) | 0.048 (3) | −0.005 (2) | −0.005 (3) | −0.015 (3) |
C2 | 0.047 (4) | 0.041 (3) | 0.068 (4) | −0.007 (3) | −0.020 (3) | −0.005 (3) |
C3 | 0.037 (3) | 0.029 (3) | 0.075 (5) | −0.002 (2) | −0.016 (3) | −0.005 (3) |
C4 | 0.055 (4) | 0.041 (3) | 0.077 (5) | −0.001 (3) | −0.011 (4) | −0.006 (3) |
C5 | 0.054 (5) | 0.044 (4) | 0.109 (7) | 0.002 (3) | 0.013 (4) | −0.005 (4) |
C6 | 0.054 (5) | 0.044 (4) | 0.121 (7) | −0.010 (3) | −0.016 (5) | −0.016 (4) |
C7 | 0.062 (5) | 0.035 (3) | 0.102 (6) | −0.004 (3) | −0.034 (4) | −0.013 (4) |
C8 | 0.053 (4) | 0.029 (3) | 0.079 (5) | −0.001 (3) | −0.016 (4) | −0.009 (3) |
C9 | 0.080 (5) | 0.043 (4) | 0.087 (6) | −0.001 (3) | −0.020 (5) | −0.014 (4) |
C10 | 0.120 (8) | 0.060 (5) | 0.091 (6) | 0.006 (5) | −0.027 (6) | −0.016 (4) |
C11 | 0.128 (9) | 0.068 (5) | 0.111 (8) | 0.002 (5) | −0.051 (7) | −0.029 (5) |
C12 | 0.090 (6) | 0.054 (4) | 0.126 (8) | −0.006 (4) | −0.042 (6) | −0.022 (5) |
C13 | 0.030 (3) | 0.038 (3) | 0.042 (3) | 0.000 (2) | −0.005 (2) | −0.021 (2) |
C14 | 0.048 (4) | 0.061 (4) | 0.065 (4) | 0.008 (3) | −0.016 (3) | −0.040 (3) |
C15 | 0.054 (4) | 0.061 (4) | 0.063 (4) | 0.002 (3) | −0.007 (3) | −0.042 (3) |
C16 | 0.073 (5) | 0.067 (4) | 0.083 (5) | −0.002 (4) | 0.012 (4) | −0.040 (4) |
C17 | 0.077 (6) | 0.097 (6) | 0.104 (7) | −0.006 (5) | 0.024 (5) | −0.055 (6) |
C18 | 0.081 (6) | 0.098 (6) | 0.116 (8) | 0.016 (5) | −0.006 (6) | −0.058 (6) |
C19 | 0.084 (6) | 0.080 (5) | 0.086 (6) | 0.015 (4) | −0.027 (5) | −0.048 (5) |
C20 | 0.060 (4) | 0.068 (4) | 0.071 (5) | 0.008 (3) | −0.020 (4) | −0.044 (4) |
C21 | 0.095 (6) | 0.078 (5) | 0.074 (5) | 0.006 (4) | −0.007 (5) | −0.031 (4) |
C22 | 0.137 (9) | 0.113 (7) | 0.082 (7) | 0.009 (7) | −0.006 (6) | −0.030 (6) |
C23 | 0.141 (10) | 0.108 (8) | 0.102 (8) | 0.020 (7) | −0.034 (7) | −0.027 (6) |
C24 | 0.107 (8) | 0.099 (7) | 0.115 (8) | 0.028 (6) | −0.039 (6) | −0.045 (6) |
C25 | 0.036 (3) | 0.043 (3) | 0.052 (4) | 0.006 (2) | −0.012 (3) | −0.025 (3) |
C26 | 0.084 (5) | 0.050 (3) | 0.059 (4) | 0.009 (3) | −0.025 (4) | −0.030 (3) |
C27 | 0.073 (5) | 0.050 (3) | 0.052 (4) | 0.002 (3) | −0.013 (3) | −0.029 (3) |
C28 | 0.083 (5) | 0.089 (5) | 0.065 (5) | 0.012 (4) | −0.010 (4) | −0.035 (4) |
C29 | 0.099 (7) | 0.121 (7) | 0.067 (6) | 0.006 (5) | 0.001 (5) | −0.028 (5) |
C30 | 0.108 (7) | 0.108 (6) | 0.056 (5) | 0.010 (5) | −0.013 (5) | −0.017 (4) |
C31 | 0.081 (5) | 0.070 (4) | 0.061 (5) | 0.004 (4) | −0.017 (4) | −0.024 (4) |
C32 | 0.068 (4) | 0.043 (3) | 0.055 (4) | 0.000 (3) | −0.014 (3) | −0.026 (3) |
C33 | 0.072 (5) | 0.061 (4) | 0.061 (4) | 0.001 (3) | −0.014 (4) | −0.029 (3) |
C34 | 0.079 (6) | 0.077 (5) | 0.087 (6) | 0.004 (4) | −0.005 (5) | −0.040 (5) |
C35 | 0.083 (6) | 0.073 (5) | 0.103 (7) | 0.017 (4) | −0.035 (5) | −0.035 (5) |
C36 | 0.099 (6) | 0.082 (5) | 0.070 (5) | 0.011 (5) | −0.032 (5) | −0.020 (4) |
C37 | 0.040 (3) | 0.039 (3) | 0.055 (4) | −0.006 (2) | −0.007 (3) | −0.015 (3) |
C38 | 0.048 (4) | 0.044 (3) | 0.063 (4) | −0.014 (3) | −0.005 (3) | −0.016 (3) |
C39 | 0.034 (3) | 0.058 (4) | 0.060 (4) | −0.016 (3) | −0.008 (3) | −0.024 (3) |
C40 | 0.031 (3) | 0.049 (3) | 0.048 (3) | −0.002 (2) | −0.009 (2) | −0.024 (3) |
C41 | 0.030 (3) | 0.043 (3) | 0.038 (3) | 0.000 (2) | −0.008 (2) | −0.021 (2) |
C42 | 0.030 (3) | 0.040 (3) | 0.043 (3) | 0.005 (2) | −0.011 (2) | −0.019 (2) |
C43 | 0.037 (3) | 0.046 (3) | 0.052 (4) | 0.006 (2) | −0.009 (3) | −0.017 (3) |
C44 | 0.049 (4) | 0.050 (4) | 0.079 (5) | 0.016 (3) | −0.023 (3) | −0.011 (3) |
C45 | 0.058 (4) | 0.039 (3) | 0.095 (5) | 0.003 (3) | −0.021 (4) | −0.010 (3) |
C46 | 0.045 (3) | 0.038 (3) | 0.077 (4) | −0.004 (3) | −0.019 (3) | −0.012 (3) |
C47 | 0.028 (3) | 0.067 (4) | 0.064 (4) | 0.002 (3) | −0.016 (3) | −0.029 (3) |
C48 | 0.032 (3) | 0.062 (4) | 0.065 (4) | 0.014 (3) | −0.018 (3) | −0.020 (3) |
C49 | 0.047 (4) | 0.041 (3) | 0.081 (5) | −0.006 (3) | −0.011 (3) | −0.019 (3) |
C50 | 0.054 (8) | 0.044 (8) | 0.078 (11) | −0.001 (6) | −0.014 (9) | −0.031 (9) |
C51 | 0.063 (10) | 0.049 (7) | 0.091 (14) | 0.004 (6) | −0.014 (8) | −0.032 (8) |
C52 | 0.064 (17) | 0.058 (9) | 0.092 (19) | 0.001 (12) | −0.004 (13) | −0.026 (11) |
C53 | 0.09 (2) | 0.07 (2) | 0.10 (3) | 0.008 (16) | −0.020 (16) | −0.026 (17) |
C54 | 0.074 (13) | 0.061 (10) | 0.104 (18) | 0.007 (9) | −0.011 (14) | −0.027 (11) |
C55 | 0.06 (9) | 0.05 (3) | 0.10 (4) | 0.00 (7) | −0.02 (9) | −0.03 (3) |
C56 | 0.062 (19) | 0.051 (12) | 0.10 (3) | 0.009 (11) | −0.012 (17) | −0.029 (16) |
C57 | 0.07 (2) | 0.06 (3) | 0.09 (4) | 0.011 (18) | −0.03 (3) | −0.03 (3) |
C58 | 0.08 (3) | 0.06 (2) | 0.10 (3) | 0.011 (17) | −0.016 (19) | −0.030 (15) |
C59 | 0.067 (14) | 0.057 (9) | 0.098 (16) | 0.014 (8) | −0.020 (12) | −0.025 (11) |
C60 | 0.07 (3) | 0.055 (13) | 0.11 (4) | 0.009 (18) | −0.01 (2) | −0.022 (19) |
C50' | 0.064 (13) | 0.056 (11) | 0.101 (19) | 0.002 (9) | −0.023 (15) | −0.021 (15) |
C51' | 0.058 (16) | 0.047 (13) | 0.09 (3) | 0.007 (10) | −0.020 (16) | −0.026 (14) |
C52' | 0.07 (4) | 0.05 (2) | 0.09 (5) | 0.01 (2) | −0.02 (3) | −0.02 (3) |
C53' | 0.08 (4) | 0.06 (3) | 0.10 (4) | 0.01 (3) | −0.01 (3) | −0.024 (19) |
C54' | 0.07 (5) | 0.06 (2) | 0.10 (5) | 0.01 (3) | −0.01 (4) | −0.02 (3) |
C55' | 0.06 (11) | 0.05 (3) | 0.09 (5) | 0.00 (8) | −0.02 (12) | −0.03 (3) |
C56' | 0.06 (2) | 0.048 (14) | 0.09 (3) | 0.001 (13) | −0.016 (19) | −0.031 (18) |
C57' | 0.07 (2) | 0.055 (13) | 0.09 (3) | 0.009 (18) | −0.01 (2) | −0.033 (17) |
C58' | 0.08 (2) | 0.06 (3) | 0.10 (3) | 0.016 (18) | −0.02 (2) | −0.03 (2) |
C59' | 0.083 (15) | 0.068 (12) | 0.104 (19) | 0.010 (11) | −0.028 (15) | −0.030 (12) |
C60' | 0.075 (16) | 0.062 (12) | 0.11 (2) | 0.006 (11) | −0.015 (15) | −0.024 (13) |
C61 | 0.034 (3) | 0.053 (3) | 0.060 (4) | 0.009 (3) | −0.015 (3) | −0.028 (3) |
C62 | 0.060 (4) | 0.082 (5) | 0.068 (4) | 0.023 (3) | −0.021 (3) | −0.044 (4) |
C63 | 0.071 (5) | 0.076 (5) | 0.069 (5) | 0.019 (4) | −0.015 (4) | −0.045 (4) |
C64 | 0.076 (6) | 0.102 (6) | 0.090 (6) | 0.017 (5) | −0.017 (5) | −0.047 (5) |
C65 | 0.089 (7) | 0.128 (8) | 0.101 (7) | 0.033 (6) | −0.020 (5) | −0.043 (7) |
C66 | 0.115 (8) | 0.104 (7) | 0.086 (6) | 0.050 (6) | −0.015 (6) | −0.037 (6) |
C67 | 0.114 (7) | 0.084 (6) | 0.072 (5) | 0.028 (5) | −0.024 (5) | −0.044 (4) |
C68 | 0.091 (6) | 0.084 (5) | 0.067 (5) | 0.020 (4) | −0.018 (4) | −0.044 (4) |
C69 | 0.108 (8) | 0.105 (7) | 0.098 (7) | −0.001 (6) | −0.022 (6) | −0.038 (6) |
C70 | 0.126 (9) | 0.119 (8) | 0.125 (9) | −0.016 (7) | −0.022 (7) | −0.043 (7) |
C71 | 0.161 (12) | 0.108 (8) | 0.123 (9) | −0.007 (9) | −0.028 (9) | −0.041 (7) |
C72 | 0.149 (10) | 0.098 (7) | 0.095 (7) | 0.024 (7) | −0.023 (7) | −0.039 (6) |
C73 | 0.035 (3) | 0.050 (3) | 0.055 (4) | −0.002 (2) | −0.011 (3) | −0.029 (3) |
C74 | 0.053 (4) | 0.072 (4) | 0.059 (4) | −0.004 (3) | −0.004 (3) | −0.035 (3) |
C75 | 0.065 (4) | 0.061 (4) | 0.062 (4) | −0.004 (3) | −0.010 (3) | −0.038 (3) |
C76 | 0.089 (6) | 0.075 (5) | 0.092 (6) | 0.005 (4) | −0.013 (4) | −0.053 (4) |
C77 | 0.116 (8) | 0.073 (5) | 0.126 (8) | −0.001 (5) | −0.025 (6) | −0.064 (5) |
C78 | 0.100 (7) | 0.088 (6) | 0.114 (7) | −0.018 (5) | −0.021 (5) | −0.058 (5) |
C79 | 0.080 (5) | 0.074 (5) | 0.081 (5) | −0.009 (4) | −0.019 (4) | −0.042 (4) |
C80 | 0.064 (4) | 0.058 (4) | 0.058 (4) | −0.015 (3) | −0.015 (3) | −0.030 (3) |
C81 | 0.060 (4) | 0.058 (4) | 0.063 (4) | −0.003 (3) | −0.014 (3) | −0.026 (3) |
C82 | 0.074 (5) | 0.076 (5) | 0.071 (5) | 0.004 (4) | −0.020 (4) | −0.023 (4) |
C83 | 0.076 (6) | 0.098 (6) | 0.093 (6) | 0.004 (5) | −0.024 (5) | −0.031 (5) |
C84 | 0.067 (5) | 0.103 (6) | 0.099 (6) | −0.021 (5) | −0.025 (4) | −0.043 (5) |
C85 | 0.051 (4) | 0.049 (4) | 0.085 (5) | 0.000 (3) | −0.024 (3) | −0.020 (3) |
C86 | 0.072 (5) | 0.044 (4) | 0.096 (6) | 0.010 (3) | −0.021 (4) | −0.017 (4) |
C87 | 0.066 (5) | 0.058 (4) | 0.077 (5) | 0.024 (3) | −0.026 (4) | −0.017 (4) |
C88 | 0.044 (4) | 0.061 (4) | 0.060 (4) | 0.017 (3) | −0.019 (3) | −0.020 (3) |
C89 | 0.038 (3) | 0.053 (3) | 0.052 (4) | 0.006 (3) | −0.015 (3) | −0.025 (3) |
C90 | 0.034 (3) | 0.057 (3) | 0.051 (4) | 0.006 (3) | −0.013 (3) | −0.025 (3) |
C91 | 0.037 (3) | 0.064 (4) | 0.053 (4) | 0.005 (3) | −0.016 (3) | −0.026 (3) |
C92 | 0.039 (4) | 0.080 (5) | 0.069 (4) | −0.009 (3) | −0.013 (3) | −0.036 (4) |
C93 | 0.048 (4) | 0.061 (4) | 0.072 (4) | −0.014 (3) | −0.009 (3) | −0.028 (3) |
C94 | 0.040 (3) | 0.052 (3) | 0.073 (4) | −0.005 (3) | −0.012 (3) | −0.026 (3) |
C95 | 0.049 (4) | 0.077 (5) | 0.066 (4) | 0.022 (3) | −0.028 (3) | −0.022 (4) |
C96 | 0.037 (3) | 0.084 (5) | 0.064 (4) | 0.011 (3) | −0.022 (3) | −0.028 (4) |
C97 | 0.112 (8) | 0.087 (6) | 0.138 (8) | 0.032 (5) | −0.067 (7) | −0.069 (6) |
C98 | 0.169 (11) | 0.124 (9) | 0.143 (10) | 0.008 (8) | −0.041 (9) | −0.043 (8) |
C99 | 0.169 (11) | 0.116 (8) | 0.147 (10) | 0.062 (7) | −0.057 (8) | −0.068 (7) |
Pr1—O3i | 2.431 (3) | C43—C48 | 1.429 (7) |
Pr1—O1 | 2.434 (3) | C44—C45 | 1.339 (8) |
Pr1—O5 | 2.448 (3) | C44—H44 | 0.9300 |
Pr1—O2i | 2.474 (3) | C45—C46 | 1.395 (8) |
Pr1—O6 | 2.548 (4) | C45—H45 | 0.9300 |
Pr1—O4 | 2.574 (4) | C46—H46 | 0.9300 |
Pr1—O3 | 2.619 (4) | C47—C48 | 1.324 (7) |
Pr1—N1 | 2.667 (4) | C47—H47 | 0.9300 |
Pr1—N2 | 2.670 (4) | C48—H48 | 0.9300 |
Pr1—Pr1i | 4.0072 (6) | C49—C50' | 1.52 (2) |
Pr2—O8ii | 2.423 (4) | C49—C50 | 1.529 (16) |
Pr2—O7 | 2.443 (4) | C50—C51 | 1.52 (2) |
Pr2—O9ii | 2.447 (3) | C50—H50A | 0.9700 |
Pr2—O12 | 2.500 (4) | C50—H50B | 0.9700 |
Pr2—O11 | 2.552 (4) | C51—C56 | 1.39 (4) |
Pr2—O10 | 2.561 (4) | C51—C52 | 1.39 (5) |
Pr2—N4 | 2.635 (4) | C52—C53 | 1.39 (7) |
Pr2—O9 | 2.644 (4) | C52—H52 | 0.9300 |
Pr2—N3 | 2.691 (4) | C53—C54 | 1.39 (6) |
Pr2—Pr2ii | 4.0433 (6) | C53—H53 | 0.9300 |
N1—C37 | 1.319 (6) | C54—C55 | 1.4 (6) |
N1—C41 | 1.352 (6) | C54—H54 | 0.9300 |
N2—C46 | 1.315 (6) | C55—C56 | 1.4 (4) |
N2—C42 | 1.367 (6) | C55—C60 | 1.4 (6) |
N3—C85 | 1.311 (7) | C56—C57 | 1.39 (10) |
N3—C89 | 1.348 (6) | C57—C58 | 1.39 (14) |
N4—C94 | 1.322 (6) | C57—H57 | 0.9300 |
N4—C90 | 1.369 (6) | C58—C59 | 1.39 (7) |
N5—C97 | 1.323 (9) | C58—H58 | 0.9300 |
N5—C99 | 1.427 (10) | C59—C60 | 1.39 (10) |
N5—C98 | 1.454 (11) | C59—H59 | 0.9300 |
O1—C1 | 1.269 (6) | C60—H60 | 0.9300 |
O2—C1 | 1.244 (6) | C50'—C51' | 1.51 (4) |
O2—Pr1i | 2.474 (3) | C50'—H50C | 0.9700 |
O3—C13 | 1.272 (5) | C50'—H50D | 0.9700 |
O3—Pr1i | 2.431 (3) | C51'—C52' | 1.39 (13) |
O4—C13 | 1.246 (6) | C51'—C56' | 1.39 (5) |
O5—C25 | 1.256 (6) | C52'—C53' | 1.39 (18) |
O6—C25 | 1.252 (6) | C52'—H52' | 0.9300 |
O7—C49 | 1.252 (7) | C53'—C54' | 1.39 (8) |
O8—C49 | 1.256 (7) | C53'—H53' | 0.9300 |
O8—Pr2ii | 2.423 (4) | C54'—C55' | 1.4 (9) |
O9—C61 | 1.261 (6) | C54'—H54' | 0.9300 |
O9—Pr2ii | 2.447 (3) | C55'—C60' | 1.4 (7) |
O10—C61 | 1.241 (6) | C55'—C56' | 1.4 (5) |
O11—C73 | 1.245 (6) | C56'—C57' | 1.39 (6) |
O12—C73 | 1.258 (6) | C57'—C58' | 1.39 (9) |
O13—C97 | 1.209 (10) | C57'—H57' | 0.9300 |
C1—C2 | 1.521 (7) | C58'—C59' | 1.39 (8) |
C2—C3 | 1.509 (7) | C58'—H58' | 0.9300 |
C2—H2A | 0.9700 | C59'—C60' | 1.39 (4) |
C2—H2B | 0.9700 | C59'—H59' | 0.9300 |
C3—C4 | 1.363 (8) | C60'—H60' | 0.9300 |
C3—C8 | 1.421 (9) | C61—C62 | 1.519 (8) |
C4—C5 | 1.419 (9) | C62—C63 | 1.504 (8) |
C4—H4 | 0.9300 | C62—H62A | 0.9700 |
C5—C6 | 1.346 (10) | C62—H62B | 0.9700 |
C5—H5 | 0.9300 | C63—C64 | 1.351 (9) |
C6—C7 | 1.382 (10) | C63—C68 | 1.436 (10) |
C6—H6 | 0.9300 | C64—C65 | 1.411 (11) |
C7—C8 | 1.418 (8) | C64—H64 | 0.9300 |
C7—C12 | 1.422 (11) | C65—C66 | 1.335 (12) |
C8—C9 | 1.405 (9) | C65—H65 | 0.9300 |
C9—C10 | 1.388 (10) | C66—C67 | 1.395 (12) |
C9—H9 | 0.9300 | C66—H66 | 0.9300 |
C10—C11 | 1.377 (11) | C67—C68 | 1.416 (10) |
C10—H10 | 0.9300 | C67—C72 | 1.447 (12) |
C11—C12 | 1.346 (11) | C68—C69 | 1.398 (11) |
C11—H11 | 0.9300 | C69—C70 | 1.393 (12) |
C12—H12 | 0.9300 | C69—H69 | 0.9300 |
C13—C14 | 1.504 (7) | C70—C71 | 1.369 (13) |
C14—C15 | 1.494 (7) | C70—H70 | 0.9300 |
C14—H14A | 0.9700 | C71—C72 | 1.330 (13) |
C14—H14B | 0.9700 | C71—H71 | 0.9300 |
C15—C16 | 1.356 (8) | C72—H72 | 0.9300 |
C15—C20 | 1.418 (8) | C73—C74 | 1.519 (8) |
C16—C17 | 1.425 (9) | C74—C75 | 1.505 (8) |
C16—H16 | 0.9300 | C74—H74A | 0.9700 |
C17—C18 | 1.323 (10) | C74—H74B | 0.9700 |
C17—H17 | 0.9300 | C75—C76 | 1.354 (8) |
C18—C19 | 1.378 (10) | C75—C80 | 1.428 (8) |
C18—H18 | 0.9300 | C76—C77 | 1.415 (10) |
C19—C20 | 1.423 (9) | C76—H76 | 0.9300 |
C19—C24 | 1.424 (10) | C77—C78 | 1.341 (10) |
C20—C21 | 1.416 (9) | C77—H77 | 0.9300 |
C21—C22 | 1.361 (10) | C78—C79 | 1.401 (10) |
C21—H21 | 0.9300 | C78—H78 | 0.9300 |
C22—C23 | 1.405 (12) | C79—C84 | 1.422 (10) |
C22—H22 | 0.9300 | C79—C80 | 1.427 (8) |
C23—C24 | 1.330 (12) | C80—C81 | 1.404 (8) |
C23—H23 | 0.9300 | C81—C82 | 1.360 (8) |
C24—H24 | 0.9300 | C81—H81 | 0.9300 |
C25—C26 | 1.500 (7) | C82—C83 | 1.380 (10) |
C26—C27 | 1.493 (8) | C82—H82 | 0.9300 |
C26—H26A | 0.9700 | C83—C84 | 1.333 (10) |
C26—H26B | 0.9700 | C83—H83 | 0.9300 |
C27—C28 | 1.348 (8) | C84—H84 | 0.9300 |
C27—C32 | 1.420 (8) | C85—C86 | 1.399 (8) |
C28—C29 | 1.389 (10) | C85—H85 | 0.9300 |
C28—H28 | 0.9300 | C86—C87 | 1.348 (9) |
C29—C30 | 1.357 (10) | C86—H86 | 0.9300 |
C29—H29 | 0.9300 | C87—C88 | 1.389 (8) |
C30—C31 | 1.419 (10) | C87—H87 | 0.9300 |
C30—H30 | 0.9300 | C88—C89 | 1.420 (7) |
C31—C36 | 1.403 (10) | C88—C95 | 1.435 (8) |
C31—C32 | 1.417 (8) | C89—C90 | 1.432 (7) |
C32—C33 | 1.408 (8) | C90—C91 | 1.411 (7) |
C33—C34 | 1.364 (9) | C91—C92 | 1.398 (8) |
C33—H33 | 0.9300 | C91—C96 | 1.432 (8) |
C34—C35 | 1.384 (10) | C92—C93 | 1.359 (8) |
C34—H34 | 0.9300 | C92—H92 | 0.9300 |
C35—C36 | 1.344 (10) | C93—C94 | 1.399 (7) |
C35—H35 | 0.9300 | C93—H93 | 0.9300 |
C36—H36 | 0.9300 | C94—H94 | 0.9300 |
C37—C38 | 1.395 (7) | C95—C96 | 1.323 (8) |
C37—H37 | 0.9300 | C95—H95 | 0.9300 |
C38—C39 | 1.362 (7) | C96—H96 | 0.9300 |
C38—H38 | 0.9300 | C97—H97 | 0.9300 |
C39—C40 | 1.396 (7) | C98—H98A | 0.9600 |
C39—H39 | 0.9300 | C98—H98B | 0.9600 |
C40—C41 | 1.417 (6) | C98—H98C | 0.9600 |
C40—C47 | 1.431 (7) | C99—H99A | 0.9600 |
C41—C42 | 1.431 (6) | C99—H99B | 0.9600 |
C42—C43 | 1.404 (7) | C99—H99C | 0.9600 |
C43—C44 | 1.401 (7) | ||
O3i—Pr1—O1 | 73.37 (11) | C38—C37—H37 | 118.3 |
O3i—Pr1—O5 | 75.11 (11) | C39—C38—C37 | 119.0 (5) |
O1—Pr1—O5 | 127.67 (12) | C39—C38—H38 | 120.5 |
O3i—Pr1—O2i | 78.62 (11) | C37—C38—H38 | 120.5 |
O1—Pr1—O2i | 136.26 (12) | C38—C39—C40 | 119.5 (5) |
O5—Pr1—O2i | 74.03 (12) | C38—C39—H39 | 120.2 |
O3i—Pr1—O6 | 88.75 (12) | C40—C39—H39 | 120.2 |
O1—Pr1—O6 | 86.78 (12) | C39—C40—C41 | 117.9 (5) |
O5—Pr1—O6 | 51.83 (11) | C39—C40—C47 | 122.7 (5) |
O2i—Pr1—O6 | 125.81 (11) | C41—C40—C47 | 119.4 (5) |
O3i—Pr1—O4 | 124.74 (11) | N1—C41—C40 | 121.8 (4) |
O1—Pr1—O4 | 87.98 (12) | N1—C41—C42 | 119.1 (4) |
O5—Pr1—O4 | 144.27 (11) | C40—C41—C42 | 119.1 (4) |
O2i—Pr1—O4 | 81.08 (11) | N2—C42—C43 | 122.4 (4) |
O6—Pr1—O4 | 142.71 (12) | N2—C42—C41 | 118.0 (4) |
O3i—Pr1—O3 | 75.04 (13) | C43—C42—C41 | 119.5 (4) |
O1—Pr1—O3 | 69.56 (12) | C44—C43—C42 | 117.1 (5) |
O5—Pr1—O3 | 137.66 (11) | C44—C43—C48 | 123.6 (5) |
O2i—Pr1—O3 | 71.17 (11) | C42—C43—C48 | 119.3 (5) |
O6—Pr1—O3 | 154.20 (11) | C45—C44—C43 | 120.3 (5) |
O4—Pr1—O3 | 49.77 (10) | C45—C44—H44 | 119.9 |
O3i—Pr1—N1 | 144.07 (12) | C43—C44—H44 | 119.9 |
O1—Pr1—N1 | 138.19 (12) | C44—C45—C46 | 119.2 (5) |
O5—Pr1—N1 | 70.72 (12) | C44—C45—H45 | 120.4 |
O2i—Pr1—N1 | 81.65 (11) | C46—C45—H45 | 120.4 |
O6—Pr1—N1 | 78.89 (12) | N2—C46—C45 | 123.6 (5) |
O4—Pr1—N1 | 80.75 (12) | N2—C46—H46 | 118.2 |
O3—Pr1—N1 | 125.68 (12) | C45—C46—H46 | 118.2 |
O3i—Pr1—N2 | 146.30 (12) | C48—C47—C40 | 120.9 (5) |
O1—Pr1—N2 | 76.77 (12) | C48—C47—H47 | 119.5 |
O5—Pr1—N2 | 112.92 (12) | C40—C47—H47 | 119.5 |
O2i—Pr1—N2 | 134.88 (12) | C47—C48—C43 | 121.8 (5) |
O6—Pr1—N2 | 74.21 (13) | C47—C48—H48 | 119.1 |
O4—Pr1—N2 | 68.65 (12) | C43—C48—H48 | 119.1 |
O3—Pr1—N2 | 108.63 (12) | O7—C49—O8 | 125.7 (5) |
N1—Pr1—N2 | 61.59 (12) | O7—C49—C50' | 124.1 (10) |
O3i—Pr1—Pr1i | 39.15 (8) | O8—C49—C50' | 108.6 (11) |
O1—Pr1—Pr1i | 66.31 (8) | O7—C49—C50 | 112.4 (8) |
O5—Pr1—Pr1i | 109.10 (8) | O8—C49—C50 | 119.4 (8) |
O2i—Pr1—Pr1i | 70.70 (8) | C51—C50—C49 | 117.8 (12) |
O6—Pr1—Pr1i | 125.11 (9) | C51—C50—H50A | 107.8 |
O4—Pr1—Pr1i | 85.62 (8) | C49—C50—H50A | 107.8 |
O3—Pr1—Pr1i | 35.88 (7) | C51—C50—H50B | 107.8 |
N1—Pr1—Pr1i | 150.75 (9) | C49—C50—H50B | 107.8 |
N2—Pr1—Pr1i | 135.52 (9) | H50A—C50—H50B | 107.2 |
O8ii—Pr2—O7 | 135.71 (12) | C56—C51—C52 | 120 (2) |
O8ii—Pr2—O9ii | 74.77 (12) | C56—C51—C50 | 120 (2) |
O7—Pr2—O9ii | 74.62 (12) | C52—C51—C50 | 120.2 (17) |
O8ii—Pr2—O12 | 80.13 (13) | C51—C52—C53 | 120 (3) |
O7—Pr2—O12 | 128.97 (13) | C51—C52—H52 | 120.0 |
O9ii—Pr2—O12 | 87.09 (12) | C53—C52—H52 | 120.0 |
O8ii—Pr2—O11 | 123.85 (13) | C54—C53—C52 | 120 (4) |
O7—Pr2—O11 | 77.91 (13) | C54—C53—H53 | 120.0 |
O9ii—Pr2—O11 | 76.21 (12) | C52—C53—H53 | 120.0 |
O12—Pr2—O11 | 51.34 (12) | C53—C54—C55 | 118 (2) |
O8ii—Pr2—O10 | 90.62 (14) | C53—C54—H54 | 120.0 |
O7—Pr2—O10 | 80.59 (13) | C55—C54—H54 | 120.0 |
O9ii—Pr2—O10 | 123.64 (12) | C56—C55—C60 | 114 (10) |
O12—Pr2—O10 | 144.47 (13) | C56—C55—C54 | 124 (10) |
O11—Pr2—O10 | 145.05 (13) | C60—C55—C54 | 120 (10) |
O8ii—Pr2—N4 | 139.13 (13) | C55—C56—C51 | 117 (10) |
O7—Pr2—N4 | 81.71 (12) | C55—C56—C57 | 124 (10) |
O9ii—Pr2—N4 | 143.02 (13) | C51—C56—C57 | 120 (6) |
O12—Pr2—N4 | 86.18 (13) | C58—C57—C56 | 120 (9) |
O11—Pr2—N4 | 71.27 (13) | C58—C57—H57 | 120.0 |
O10—Pr2—N4 | 78.64 (13) | C56—C57—H57 | 120.0 |
O8ii—Pr2—O9 | 68.76 (12) | C59—C58—C57 | 120 (7) |
O7—Pr2—O9 | 72.88 (12) | C59—C58—H58 | 120.0 |
O9ii—Pr2—O9 | 74.90 (13) | C57—C58—H58 | 120.0 |
O12—Pr2—O9 | 147.08 (12) | C60—C59—C58 | 120 (4) |
O11—Pr2—O9 | 143.23 (11) | C60—C59—H59 | 120.0 |
O10—Pr2—O9 | 49.45 (11) | C58—C59—H59 | 120.0 |
N4—Pr2—O9 | 124.51 (12) | C59—C60—C55 | 120 (10) |
O8ii—Pr2—N3 | 77.85 (13) | C59—C60—H60 | 120.0 |
O7—Pr2—N3 | 135.74 (13) | C55—C60—H60 | 118.0 (2) |
O9ii—Pr2—N3 | 149.46 (12) | C51'—C50'—C49 | 122.3 (18) |
O12—Pr2—N3 | 75.05 (14) | C51'—C50'—H50C | 106.8 |
O11—Pr2—N3 | 109.13 (13) | C49—C50'—H50C | 106.8 |
O10—Pr2—N3 | 69.46 (13) | C51'—C50'—H50D | 106.8 |
N4—Pr2—N3 | 61.41 (13) | C49—C50'—H50D | 106.8 |
O9—Pr2—N3 | 107.33 (12) | H50C—C50'—H50D | 106.6 |
O8ii—Pr2—Pr2ii | 66.68 (9) | C52'—C51'—C56' | 120 (7) |
O7—Pr2—Pr2ii | 69.33 (8) | C52'—C51'—C50' | 109 (8) |
O9ii—Pr2—Pr2ii | 39.15 (9) | C56'—C51'—C50' | 131 (3) |
O12—Pr2—Pr2ii | 121.21 (9) | C51'—C52'—C53' | 120 (10) |
O11—Pr2—Pr2ii | 112.31 (8) | C51'—C52'—H52' | 120.0 |
O10—Pr2—Pr2ii | 84.84 (9) | C53'—C52'—H52' | 120.0 |
N4—Pr2—Pr2ii | 148.64 (9) | C52'—C53'—C54' | 120 (10) |
O9—Pr2—Pr2ii | 35.75 (7) | C52'—C53'—H53' | 120.0 |
N3—Pr2—Pr2ii | 135.73 (10) | C54'—C53'—H53' | 120.0 |
C37—N1—C41 | 118.4 (4) | C53'—C54'—C55' | 118 (2) |
C37—N1—Pr1 | 120.9 (3) | C53'—C54'—H54' | 120.0 |
C41—N1—Pr1 | 120.7 (3) | C55'—C54'—H54' | 123.0 |
C46—N2—C42 | 117.4 (4) | C60'—C55'—C54' | 120 (10) |
C46—N2—Pr1 | 122.0 (3) | C60'—C55'—C56' | 114 (10) |
C42—N2—Pr1 | 120.6 (3) | C54'—C55'—C56' | 127 (10) |
C85—N3—C89 | 117.6 (5) | C57'—C56'—C51' | 120 (4) |
C85—N3—Pr2 | 122.4 (4) | C57'—C56'—C55' | 124 (10) |
C89—N3—Pr2 | 120.0 (3) | C51'—C56'—C55' | 116 (10) |
C94—N4—C90 | 117.6 (5) | C56'—C57'—C58' | 120 (5) |
C94—N4—Pr2 | 120.4 (3) | C56'—C57'—H57' | 120.0 |
C90—N4—Pr2 | 122.0 (3) | C58'—C57'—H57' | 120.0 |
C97—N5—C99 | 121.7 (9) | C57'—C58'—C59' | 120 (5) |
C97—N5—C98 | 120.9 (9) | C57'—C58'—H58' | 120.0 |
C99—N5—C98 | 117.5 (8) | C59'—C58'—H58' | 120.0 |
C1—O1—Pr1 | 142.0 (3) | C60'—C59'—C58' | 120 (4) |
C1—O2—Pr1i | 130.8 (3) | C60'—C59'—H59' | 120.0 |
C13—O3—Pr1i | 161.8 (3) | C58'—C59'—H59' | 120.0 |
C13—O3—Pr1 | 93.1 (3) | C55'—C60'—C59' | 122 (2) |
Pr1i—O3—Pr1 | 104.96 (13) | C55'—C60'—H60' | 118.0 (2) |
C13—O4—Pr1 | 95.9 (3) | C59'—C60'—H60' | 120.0 |
C25—O5—Pr1 | 95.4 (3) | O10—C61—O9 | 121.1 (6) |
C25—O6—Pr1 | 90.8 (3) | O10—C61—C62 | 120.7 (5) |
C49—O7—Pr2 | 129.0 (3) | O9—C61—C62 | 118.2 (5) |
C49—O8—Pr2ii | 137.3 (4) | C63—C62—C61 | 115.9 (5) |
C61—O9—Pr2ii | 160.7 (4) | C63—C62—H62A | 108.3 |
C61—O9—Pr2 | 92.5 (3) | C61—C62—H62A | 108.3 |
Pr2ii—O9—Pr2 | 105.10 (13) | C63—C62—H62B | 108.3 |
C61—O10—Pr2 | 97.0 (3) | C61—C62—H62B | 108.3 |
C73—O11—Pr2 | 92.2 (3) | H62A—C62—H62B | 107.4 |
C73—O12—Pr2 | 94.3 (3) | C64—C63—C68 | 118.1 (7) |
O2—C1—O1 | 125.9 (4) | C64—C63—C62 | 118.5 (7) |
O2—C1—C2 | 120.5 (4) | C68—C63—C62 | 123.3 (7) |
O1—C1—C2 | 113.6 (5) | C63—C64—C65 | 122.4 (8) |
C3—C2—C1 | 117.9 (4) | C63—C64—H64 | 118.8 |
C3—C2—H2A | 107.8 | C65—C64—H64 | 118.8 |
C1—C2—H2A | 107.8 | C66—C65—C64 | 119.3 (9) |
C3—C2—H2B | 107.8 | C66—C65—H65 | 120.3 |
C1—C2—H2B | 107.8 | C64—C65—H65 | 120.3 |
H2A—C2—H2B | 107.2 | C65—C66—C67 | 122.0 (9) |
C4—C3—C8 | 119.7 (6) | C65—C66—H66 | 119.0 |
C4—C3—C2 | 119.0 (6) | C67—C66—H66 | 119.0 |
C8—C3—C2 | 121.3 (6) | C66—C67—C68 | 118.7 (9) |
C3—C4—C5 | 121.1 (7) | C66—C67—C72 | 120.9 (9) |
C3—C4—H4 | 119.5 | C68—C67—C72 | 120.4 (9) |
C5—C4—H4 | 119.5 | C69—C68—C67 | 117.5 (8) |
C6—C5—C4 | 119.1 (7) | C69—C68—C63 | 123.2 (7) |
C6—C5—H5 | 120.4 | C67—C68—C63 | 119.3 (8) |
C4—C5—H5 | 120.4 | C70—C69—C68 | 120.1 (9) |
C5—C6—C7 | 122.0 (7) | C70—C69—H69 | 119.9 |
C5—C6—H6 | 119.0 | C68—C69—H69 | 119.9 |
C7—C6—H6 | 119.0 | C71—C70—C69 | 121.3 (11) |
C6—C7—C8 | 119.7 (8) | C71—C70—H70 | 119.3 |
C6—C7—C12 | 121.8 (7) | C69—C70—H70 | 119.3 |
C8—C7—C12 | 118.5 (8) | C72—C71—C70 | 121.7 (12) |
C9—C8—C7 | 118.6 (7) | C72—C71—H71 | 119.1 |
C9—C8—C3 | 123.0 (6) | C70—C71—H71 | 119.1 |
C7—C8—C3 | 118.4 (7) | C71—C72—C67 | 118.9 (10) |
C10—C9—C8 | 120.9 (7) | C71—C72—H72 | 120.6 |
C10—C9—H9 | 119.5 | C67—C72—H72 | 120.6 |
C8—C9—H9 | 119.5 | O11—C73—O12 | 122.1 (5) |
C11—C10—C9 | 119.5 (9) | O11—C73—C74 | 119.3 (5) |
C11—C10—H10 | 120.2 | O12—C73—C74 | 118.6 (5) |
C9—C10—H10 | 120.2 | C75—C74—C73 | 114.9 (5) |
C12—C11—C10 | 121.7 (9) | C75—C74—H74A | 108.5 |
C12—C11—H11 | 119.1 | C73—C74—H74A | 108.5 |
C10—C11—H11 | 119.1 | C75—C74—H74B | 108.5 |
C11—C12—C7 | 120.7 (8) | C73—C74—H74B | 108.5 |
C11—C12—H12 | 119.7 | H74A—C74—H74B | 107.5 |
C7—C12—H12 | 119.7 | C76—C75—C80 | 118.4 (6) |
O4—C13—O3 | 120.5 (5) | C76—C75—C74 | 121.9 (6) |
O4—C13—C14 | 121.4 (5) | C80—C75—C74 | 119.6 (5) |
O3—C13—C14 | 118.1 (5) | C75—C76—C77 | 122.1 (7) |
C15—C14—C13 | 116.5 (5) | C75—C76—H76 | 119.0 |
C15—C14—H14A | 108.2 | C77—C76—H76 | 119.0 |
C13—C14—H14A | 108.2 | C78—C77—C76 | 118.9 (7) |
C15—C14—H14B | 108.2 | C78—C77—H77 | 120.5 |
C13—C14—H14B | 108.2 | C76—C77—H77 | 120.5 |
H14A—C14—H14B | 107.3 | C77—C78—C79 | 123.2 (8) |
C16—C15—C20 | 117.8 (6) | C77—C78—H78 | 118.4 |
C16—C15—C14 | 120.7 (6) | C79—C78—H78 | 118.4 |
C20—C15—C14 | 121.5 (6) | C78—C79—C84 | 124.8 (7) |
C15—C16—C17 | 121.3 (7) | C78—C79—C80 | 116.9 (7) |
C15—C16—H16 | 119.3 | C84—C79—C80 | 118.3 (7) |
C17—C16—H16 | 119.3 | C81—C80—C79 | 116.3 (6) |
C18—C17—C16 | 119.6 (7) | C81—C80—C75 | 123.3 (6) |
C18—C17—H17 | 120.2 | C79—C80—C75 | 120.4 (6) |
C16—C17—H17 | 120.2 | C82—C81—C80 | 123.1 (6) |
C17—C18—C19 | 123.1 (8) | C82—C81—H81 | 118.4 |
C17—C18—H18 | 118.4 | C80—C81—H81 | 118.4 |
C19—C18—H18 | 118.4 | C81—C82—C83 | 119.8 (7) |
C18—C19—C20 | 117.3 (7) | C81—C82—H82 | 120.1 |
C18—C19—C24 | 123.2 (8) | C83—C82—H82 | 120.1 |
C20—C19—C24 | 119.5 (8) | C84—C83—C82 | 120.1 (8) |
C21—C20—C15 | 121.2 (6) | C84—C83—H83 | 119.9 |
C21—C20—C19 | 117.9 (7) | C82—C83—H83 | 119.9 |
C15—C20—C19 | 120.9 (6) | C83—C84—C79 | 122.2 (7) |
C22—C21—C20 | 121.3 (8) | C83—C84—H84 | 118.9 |
C22—C21—H21 | 119.4 | C79—C84—H84 | 118.9 |
C20—C21—H21 | 119.4 | N3—C85—C86 | 123.9 (6) |
C21—C22—C23 | 119.0 (9) | N3—C85—H85 | 118.1 |
C21—C22—H22 | 120.5 | C86—C85—H85 | 118.1 |
C23—C22—H22 | 120.5 | C87—C86—C85 | 118.7 (6) |
C24—C23—C22 | 122.8 (9) | C87—C86—H86 | 120.7 |
C24—C23—H23 | 118.6 | C85—C86—H86 | 120.7 |
C22—C23—H23 | 118.6 | C86—C87—C88 | 120.2 (6) |
C23—C24—C19 | 119.4 (9) | C86—C87—H87 | 119.9 |
C23—C24—H24 | 120.3 | C88—C87—H87 | 119.9 |
C19—C24—H24 | 120.3 | C87—C88—C89 | 117.1 (6) |
O6—C25—O5 | 121.2 (5) | C87—C88—C95 | 124.0 (5) |
O6—C25—C26 | 123.4 (5) | C89—C88—C95 | 119.0 (6) |
O5—C25—C26 | 115.3 (5) | N3—C89—C88 | 122.5 (5) |
C27—C26—C25 | 118.1 (5) | N3—C89—C90 | 119.0 (5) |
C27—C26—H26A | 107.8 | C88—C89—C90 | 118.5 (5) |
C25—C26—H26A | 107.8 | N4—C90—C91 | 121.9 (5) |
C27—C26—H26B | 107.8 | N4—C90—C89 | 117.6 (5) |
C25—C26—H26B | 107.8 | C91—C90—C89 | 120.5 (5) |
H26A—C26—H26B | 107.1 | C92—C91—C90 | 117.9 (5) |
C28—C27—C32 | 119.7 (6) | C92—C91—C96 | 123.4 (5) |
C28—C27—C26 | 118.0 (6) | C90—C91—C96 | 118.8 (5) |
C32—C27—C26 | 122.2 (6) | C93—C92—C91 | 120.2 (5) |
C27—C28—C29 | 121.4 (7) | C93—C92—H92 | 119.9 |
C27—C28—H28 | 119.3 | C91—C92—H92 | 119.9 |
C29—C28—H28 | 119.3 | C92—C93—C94 | 118.4 (6) |
C30—C29—C28 | 120.6 (8) | C92—C93—H93 | 120.8 |
C30—C29—H29 | 119.7 | C94—C93—H93 | 120.8 |
C28—C29—H29 | 119.7 | N4—C94—C93 | 124.1 (5) |
C29—C30—C31 | 120.7 (7) | N4—C94—H94 | 118.0 |
C29—C30—H30 | 119.7 | C93—C94—H94 | 118.0 |
C31—C30—H30 | 119.7 | C96—C95—C88 | 122.0 (6) |
C36—C31—C32 | 119.4 (7) | C96—C95—H95 | 119.0 |
C36—C31—C30 | 122.7 (7) | C88—C95—H95 | 119.0 |
C32—C31—C30 | 117.9 (7) | C95—C96—C91 | 121.2 (6) |
C33—C32—C31 | 117.7 (6) | C95—C96—H96 | 119.4 |
C33—C32—C27 | 122.6 (6) | C91—C96—H96 | 119.4 |
C31—C32—C27 | 119.7 (6) | O13—C97—N5 | 124.9 (11) |
C34—C33—C32 | 120.8 (7) | O13—C97—H97 | 117.5 |
C34—C33—H33 | 119.6 | N5—C97—H97 | 117.5 |
C32—C33—H33 | 119.6 | N5—C98—H98A | 109.5 |
C33—C34—C35 | 120.8 (7) | N5—C98—H98B | 109.5 |
C33—C34—H34 | 119.6 | H98A—C98—H98B | 109.5 |
C35—C34—H34 | 119.6 | N5—C98—H98C | 109.5 |
C36—C35—C34 | 120.3 (8) | H98A—C98—H98C | 109.5 |
C36—C35—H35 | 119.8 | H98B—C98—H98C | 109.5 |
C34—C35—H35 | 119.8 | N5—C99—H99A | 109.5 |
C35—C36—C31 | 121.0 (7) | N5—C99—H99B | 109.5 |
C35—C36—H36 | 119.5 | H99A—C99—H99B | 109.5 |
C31—C36—H36 | 119.5 | N5—C99—H99C | 109.5 |
N1—C37—C38 | 123.4 (5) | H99A—C99—H99C | 109.5 |
N1—C37—H37 | 118.3 | H99B—C99—H99C | 109.5 |
O3i—Pr1—N1—C37 | −28.8 (5) | C15—C20—C21—C22 | 176.0 (8) |
O1—Pr1—N1—C37 | −173.0 (4) | C19—C20—C21—C22 | −2.4 (11) |
O5—Pr1—N1—C37 | −47.6 (4) | C20—C21—C22—C23 | 3.4 (14) |
O2i—Pr1—N1—C37 | 28.4 (4) | C21—C22—C23—C24 | −1.0 (17) |
O6—Pr1—N1—C37 | −100.8 (4) | C22—C23—C24—C19 | −2.4 (16) |
O4—Pr1—N1—C37 | 110.6 (4) | C18—C19—C24—C23 | −177.2 (9) |
O3—Pr1—N1—C37 | 87.9 (4) | C20—C19—C24—C23 | 3.3 (13) |
N2—Pr1—N1—C37 | −178.7 (4) | Pr1—O6—C25—O5 | 8.0 (5) |
Pr1i—Pr1—N1—C37 | 47.3 (5) | Pr1—O6—C25—C26 | −170.1 (5) |
O3i—Pr1—N1—C41 | 150.1 (3) | Pr1—O5—C25—O6 | −8.4 (5) |
O1—Pr1—N1—C41 | 5.9 (5) | Pr1—O5—C25—C26 | 169.9 (4) |
O5—Pr1—N1—C41 | 131.3 (4) | O6—C25—C26—C27 | 4.2 (9) |
O2i—Pr1—N1—C41 | −152.8 (4) | O5—C25—C26—C27 | −174.0 (5) |
O6—Pr1—N1—C41 | 78.1 (4) | C25—C26—C27—C28 | −106.8 (7) |
O4—Pr1—N1—C41 | −70.5 (4) | C25—C26—C27—C32 | 77.2 (8) |
O3—Pr1—N1—C41 | −93.2 (4) | C32—C27—C28—C29 | −1.4 (11) |
N2—Pr1—N1—C41 | 0.1 (3) | C26—C27—C28—C29 | −177.6 (7) |
Pr1i—Pr1—N1—C41 | −133.8 (3) | C27—C28—C29—C30 | 1.9 (13) |
O3i—Pr1—N2—C46 | 33.8 (6) | C28—C29—C30—C31 | −0.4 (14) |
O1—Pr1—N2—C46 | 5.7 (4) | C29—C30—C31—C36 | 178.2 (8) |
O5—Pr1—N2—C46 | 131.3 (4) | C29—C30—C31—C32 | −1.5 (12) |
O2i—Pr1—N2—C46 | −138.7 (4) | C36—C31—C32—C33 | 0.6 (9) |
O6—Pr1—N2—C46 | 96.1 (5) | C30—C31—C32—C33 | −179.7 (6) |
O4—Pr1—N2—C46 | −87.3 (5) | C36—C31—C32—C27 | −177.8 (6) |
O3—Pr1—N2—C46 | −57.1 (5) | C30—C31—C32—C27 | 1.9 (9) |
N1—Pr1—N2—C46 | −178.2 (5) | C28—C27—C32—C33 | −178.8 (6) |
Pr1i—Pr1—N2—C46 | −28.3 (5) | C26—C27—C32—C33 | −2.9 (9) |
O3i—Pr1—N2—C42 | −148.1 (3) | C28—C27—C32—C31 | −0.5 (9) |
O1—Pr1—N2—C42 | −176.2 (4) | C26—C27—C32—C31 | 175.4 (5) |
O5—Pr1—N2—C42 | −50.6 (4) | C31—C32—C33—C34 | −0.4 (9) |
O2i—Pr1—N2—C42 | 39.4 (5) | C27—C32—C33—C34 | 177.9 (6) |
O6—Pr1—N2—C42 | −85.8 (4) | C32—C33—C34—C35 | −0.3 (10) |
O4—Pr1—N2—C42 | 90.8 (4) | C33—C34—C35—C36 | 0.7 (12) |
O3—Pr1—N2—C42 | 121.1 (4) | C34—C35—C36—C31 | −0.5 (12) |
N1—Pr1—N2—C42 | −0.1 (4) | C32—C31—C36—C35 | −0.2 (11) |
Pr1i—Pr1—N2—C42 | 149.8 (3) | C30—C31—C36—C35 | −179.8 (8) |
O8ii—Pr2—N3—C85 | 3.0 (5) | C41—N1—C37—C38 | 0.7 (8) |
O7—Pr2—N3—C85 | −142.9 (5) | Pr1—N1—C37—C38 | 179.6 (4) |
O9ii—Pr2—N3—C85 | 29.7 (6) | N1—C37—C38—C39 | −0.2 (9) |
O12—Pr2—N3—C85 | 85.9 (5) | C37—C38—C39—C40 | −0.1 (9) |
O11—Pr2—N3—C85 | 124.9 (5) | C38—C39—C40—C41 | −0.1 (8) |
O10—Pr2—N3—C85 | −92.3 (5) | C38—C39—C40—C47 | 179.4 (6) |
N4—Pr2—N3—C85 | 179.7 (5) | C37—N1—C41—C40 | −1.0 (8) |
O9—Pr2—N3—C85 | −59.9 (5) | Pr1—N1—C41—C40 | −179.8 (4) |
Pr2ii—Pr2—N3—C85 | −33.7 (5) | C37—N1—C41—C42 | 178.7 (5) |
O8ii—Pr2—N3—C89 | −178.1 (4) | Pr1—N1—C41—C42 | −0.2 (6) |
O7—Pr2—N3—C89 | 36.0 (5) | C39—C40—C41—N1 | 0.7 (8) |
O9ii—Pr2—N3—C89 | −151.4 (4) | C47—C40—C41—N1 | −178.8 (5) |
O12—Pr2—N3—C89 | −95.2 (4) | C39—C40—C41—C42 | −179.0 (5) |
O11—Pr2—N3—C89 | −56.2 (4) | C47—C40—C41—C42 | 1.5 (8) |
O10—Pr2—N3—C89 | 86.6 (4) | C46—N2—C42—C43 | −1.5 (8) |
N4—Pr2—N3—C89 | −1.4 (4) | Pr1—N2—C42—C43 | −179.7 (4) |
O9—Pr2—N3—C89 | 119.0 (4) | C46—N2—C42—C41 | 178.3 (5) |
Pr2ii—Pr2—N3—C89 | 145.2 (4) | Pr1—N2—C42—C41 | 0.1 (6) |
O8ii—Pr2—N4—C94 | −173.4 (4) | N1—C41—C42—N2 | 0.1 (7) |
O7—Pr2—N4—C94 | 27.1 (4) | C40—C41—C42—N2 | 179.8 (5) |
O9ii—Pr2—N4—C94 | −23.2 (5) | N1—C41—C42—C43 | 179.9 (5) |
O12—Pr2—N4—C94 | −103.2 (4) | C40—C41—C42—C43 | −0.5 (8) |
O11—Pr2—N4—C94 | −52.9 (4) | N2—C42—C43—C44 | 0.7 (9) |
O10—Pr2—N4—C94 | 109.0 (4) | C41—C42—C43—C44 | −179.0 (5) |
O9—Pr2—N4—C94 | 89.6 (4) | N2—C42—C43—C48 | 178.5 (5) |
N3—Pr2—N4—C94 | −178.3 (5) | C41—C42—C43—C48 | −1.2 (8) |
Pr2ii—Pr2—N4—C94 | 49.4 (5) | C42—C43—C44—C45 | 1.0 (10) |
O8ii—Pr2—N4—C90 | 6.6 (5) | C48—C43—C44—C45 | −176.7 (6) |
O7—Pr2—N4—C90 | −153.0 (4) | C43—C44—C45—C46 | −1.9 (11) |
O9ii—Pr2—N4—C90 | 156.8 (4) | C42—N2—C46—C45 | 0.6 (9) |
O12—Pr2—N4—C90 | 76.7 (4) | Pr1—N2—C46—C45 | 178.8 (5) |
O11—Pr2—N4—C90 | 127.1 (4) | C44—C45—C46—N2 | 1.1 (11) |
O10—Pr2—N4—C90 | −71.0 (4) | C39—C40—C47—C48 | 179.7 (6) |
O9—Pr2—N4—C90 | −90.4 (4) | C41—C40—C47—C48 | −0.8 (9) |
N3—Pr2—N4—C90 | 1.7 (4) | C40—C47—C48—C43 | −1.0 (10) |
Pr2ii—Pr2—N4—C90 | −130.6 (4) | C44—C43—C48—C47 | 179.7 (6) |
O3i—Pr1—O1—C1 | 36.5 (6) | C42—C43—C48—C47 | 2.0 (9) |
O5—Pr1—O1—C1 | 91.7 (6) | Pr2—O7—C49—O8 | −48.1 (9) |
O2i—Pr1—O1—C1 | −16.0 (7) | Pr2—O7—C49—C50' | 148.0 (14) |
O6—Pr1—O1—C1 | 126.1 (6) | Pr2—O7—C49—C50 | 113.9 (8) |
O4—Pr1—O1—C1 | −90.8 (6) | Pr2ii—O8—C49—O7 | 39.4 (11) |
O3—Pr1—O1—C1 | −43.4 (6) | Pr2ii—O8—C49—C50' | −154.7 (12) |
N1—Pr1—O1—C1 | −164.5 (5) | Pr2ii—O8—C49—C50 | −121.5 (9) |
N2—Pr1—O1—C1 | −159.4 (6) | O7—C49—C50—C51 | 36.0 (16) |
Pr1i—Pr1—O1—C1 | −4.7 (6) | O8—C49—C50—C51 | −160.8 (11) |
O3i—Pr1—O3—C13 | −178.1 (3) | C50'—C49—C50—C51 | −83 (3) |
O1—Pr1—O3—C13 | −100.6 (3) | C49—C50—C51—C56 | 75.7 (19) |
O5—Pr1—O3—C13 | 135.3 (3) | C49—C50—C51—C52 | −106 (2) |
O2i—Pr1—O3—C13 | 99.0 (3) | C56—C51—C52—C53 | 0 (4) |
O6—Pr1—O3—C13 | −125.3 (3) | C50—C51—C52—C53 | −179 (3) |
O4—Pr1—O3—C13 | 4.8 (3) | C51—C52—C53—C54 | 0 (5) |
N1—Pr1—O3—C13 | 34.7 (3) | C52—C53—C54—C55 | 4 (22) |
N2—Pr1—O3—C13 | −33.2 (3) | C53—C54—C55—C56 | −10 (11) |
Pr1i—Pr1—O3—C13 | −178.1 (3) | C53—C54—C55—C60 | −175 (22) |
O3i—Pr1—O3—Pr1i | 0.000 (2) | C60—C55—C56—C51 | 180 (22) |
O1—Pr1—O3—Pr1i | 77.49 (13) | C54—C55—C56—C51 | 10 (9) |
O5—Pr1—O3—Pr1i | −46.5 (2) | C60—C55—C56—C57 | −9 (10) |
O2i—Pr1—O3—Pr1i | −82.84 (13) | C54—C55—C56—C57 | −174 (22) |
O6—Pr1—O3—Pr1i | 52.8 (3) | C52—C51—C56—C55 | −4 (22) |
O4—Pr1—O3—Pr1i | −177.09 (19) | C50—C51—C56—C55 | 179 (22) |
N1—Pr1—O3—Pr1i | −147.14 (12) | C52—C51—C56—C57 | 180 (6) |
N2—Pr1—O3—Pr1i | 144.95 (12) | C50—C51—C56—C57 | −1 (6) |
O3i—Pr1—O4—C13 | −8.3 (3) | C55—C56—C57—C58 | 5 (24) |
O1—Pr1—O4—C13 | 59.8 (3) | C51—C56—C57—C58 | −180 (6) |
O5—Pr1—O4—C13 | −123.7 (3) | C56—C57—C58—C59 | 0 (13) |
O2i—Pr1—O4—C13 | −77.7 (3) | C57—C58—C59—C60 | 0 (9) |
O6—Pr1—O4—C13 | 141.8 (3) | C58—C59—C60—C55 | −5 (23) |
O3—Pr1—O4—C13 | −4.9 (3) | C56—C55—C60—C59 | 8 (7) |
N1—Pr1—O4—C13 | −160.6 (3) | C54—C55—C60—C59 | 175 (22) |
N2—Pr1—O4—C13 | 136.4 (3) | O7—C49—C50'—C51' | 22 (3) |
Pr1i—Pr1—O4—C13 | −6.6 (3) | O8—C49—C50'—C51' | −145 (3) |
O3i—Pr1—O5—C25 | 104.9 (3) | C50—C49—C50'—C51' | 99 (4) |
O1—Pr1—O5—C25 | 50.3 (3) | C49—C50'—C51'—C52' | 108 (7) |
O2i—Pr1—O5—C25 | −173.0 (3) | C49—C50'—C51'—C56' | −74 (4) |
O6—Pr1—O5—C25 | 4.5 (3) | C56'—C51'—C52'—C53' | 0 (15) |
O4—Pr1—O5—C25 | −125.3 (3) | C50'—C51'—C52'—C53' | 179 (9) |
O3—Pr1—O5—C25 | 151.4 (3) | C51'—C52'—C53'—C54' | 0 (18) |
N1—Pr1—O5—C25 | −86.4 (3) | C52'—C53'—C54'—C55' | −2 (2) |
N2—Pr1—O5—C25 | −40.5 (3) | C53'—C54'—C55'—C60' | 178 (2) |
Pr1i—Pr1—O5—C25 | 124.6 (3) | C53'—C54'—C55'—C56' | 4 (4) |
O3i—Pr1—O6—C25 | −76.4 (3) | C52'—C51'—C56'—C57' | −180 (8) |
O1—Pr1—O6—C25 | −149.8 (3) | C50'—C51'—C56'—C57' | 2 (5) |
O5—Pr1—O6—C25 | −4.5 (3) | C52'—C51'—C56'—C55' | 2 (2) |
O2i—Pr1—O6—C25 | −1.4 (3) | C50'—C51'—C56'—C55' | −176 (2) |
O4—Pr1—O6—C25 | 127.8 (3) | C60'—C55'—C56'—C57' | 3 (3) |
O3—Pr1—O6—C25 | −126.7 (3) | C54'—C55'—C56'—C57' | 178 (2) |
N1—Pr1—O6—C25 | 69.7 (3) | C60'—C55'—C56'—C51' | 180 (28) |
N2—Pr1—O6—C25 | 133.0 (3) | C54'—C55'—C56'—C51' | −4 (4) |
Pr1i—Pr1—O6—C25 | −91.9 (3) | C51'—C56'—C57'—C58' | 180 (4) |
O8ii—Pr2—O7—C49 | 33.4 (6) | C55'—C56'—C57'—C58' | −2 (2) |
O9ii—Pr2—O7—C49 | −14.4 (5) | C56'—C57'—C58'—C59' | 0 (6) |
O12—Pr2—O7—C49 | −87.5 (5) | C57'—C58'—C59'—C60' | 0 (6) |
O11—Pr2—O7—C49 | −93.2 (5) | C54'—C55'—C60'—C59' | 180 (28) |
O10—Pr2—O7—C49 | 114.5 (5) | C56'—C55'—C60'—C59' | −3 (3) |
N4—Pr2—O7—C49 | −165.7 (5) | C58'—C59'—C60'—C55' | 2 (2) |
O9—Pr2—O7—C49 | 64.2 (5) | Pr2—O10—C61—O9 | 2.7 (6) |
N3—Pr2—O7—C49 | 161.7 (5) | Pr2—O10—C61—C62 | −179.9 (5) |
Pr2ii—Pr2—O7—C49 | 26.5 (5) | Pr2ii—O9—C61—O10 | 152.9 (8) |
O8ii—Pr2—O9—C61 | −109.0 (3) | Pr2—O9—C61—O10 | −2.6 (6) |
O7—Pr2—O9—C61 | 93.6 (3) | Pr2ii—O9—C61—C62 | −24.6 (14) |
O9ii—Pr2—O9—C61 | 171.8 (4) | Pr2—O9—C61—C62 | 179.9 (5) |
O12—Pr2—O9—C61 | −129.1 (3) | O10—C61—C62—C63 | 45.5 (9) |
O11—Pr2—O9—C61 | 132.5 (3) | O9—C61—C62—C63 | −137.0 (6) |
O10—Pr2—O9—C61 | 1.4 (3) | C61—C62—C63—C64 | −77.8 (8) |
N4—Pr2—O9—C61 | 26.9 (3) | C61—C62—C63—C68 | 105.0 (8) |
N3—Pr2—O9—C61 | −39.9 (3) | C68—C63—C64—C65 | −2.1 (12) |
Pr2ii—Pr2—O9—C61 | 171.8 (4) | C62—C63—C64—C65 | −179.3 (7) |
O8ii—Pr2—O9—Pr2ii | 79.22 (14) | C63—C64—C65—C66 | 0.9 (14) |
O7—Pr2—O9—Pr2ii | −78.21 (14) | C64—C65—C66—C67 | 2.4 (15) |
O9ii—Pr2—O9—Pr2ii | 0.0 | C65—C66—C67—C68 | −4.3 (14) |
O12—Pr2—O9—Pr2ii | 59.1 (2) | C65—C66—C67—C72 | 175.9 (9) |
O11—Pr2—O9—Pr2ii | −39.3 (2) | C66—C67—C68—C69 | −179.0 (8) |
O10—Pr2—O9—Pr2ii | −170.4 (2) | C72—C67—C68—C69 | 0.7 (11) |
N4—Pr2—O9—Pr2ii | −144.95 (13) | C66—C67—C68—C63 | 3.0 (11) |
N3—Pr2—O9—Pr2ii | 148.24 (13) | C72—C67—C68—C63 | −177.2 (7) |
O8ii—Pr2—O10—C61 | 59.5 (3) | C64—C63—C68—C69 | −177.8 (7) |
O7—Pr2—O10—C61 | −76.9 (3) | C62—C63—C68—C69 | −0.6 (11) |
O9ii—Pr2—O10—C61 | −12.6 (4) | C64—C63—C68—C67 | 0.1 (11) |
O12—Pr2—O10—C61 | 133.2 (3) | C62—C63—C68—C67 | 177.2 (6) |
O11—Pr2—O10—C61 | −129.5 (3) | C67—C68—C69—C70 | 0.2 (12) |
N4—Pr2—O10—C61 | −160.3 (4) | C63—C68—C69—C70 | 178.0 (8) |
O9—Pr2—O10—C61 | −1.4 (3) | C68—C69—C70—C71 | 0.6 (15) |
N3—Pr2—O10—C61 | 136.2 (4) | C69—C70—C71—C72 | −2.4 (18) |
Pr2ii—Pr2—O10—C61 | −7.0 (3) | C70—C71—C72—C67 | 3.3 (17) |
O8ii—Pr2—O11—C73 | 38.0 (3) | C66—C67—C72—C71 | 177.3 (9) |
O7—Pr2—O11—C73 | 175.6 (3) | C68—C67—C72—C71 | −2.5 (14) |
O9ii—Pr2—O11—C73 | 98.7 (3) | Pr2—O11—C73—O12 | −2.3 (5) |
O12—Pr2—O11—C73 | 1.2 (3) | Pr2—O11—C73—C74 | 178.6 (4) |
O10—Pr2—O11—C73 | −131.2 (3) | Pr2—O12—C73—O11 | 2.3 (5) |
N4—Pr2—O11—C73 | −99.2 (3) | Pr2—O12—C73—C74 | −178.5 (4) |
O9—Pr2—O11—C73 | 137.7 (3) | O11—C73—C74—C75 | −46.9 (8) |
N3—Pr2—O11—C73 | −49.9 (3) | O12—C73—C74—C75 | 133.9 (6) |
Pr2ii—Pr2—O11—C73 | 114.1 (3) | C73—C74—C75—C76 | 114.1 (7) |
O8ii—Pr2—O12—C73 | −150.9 (3) | C73—C74—C75—C80 | −68.5 (8) |
O7—Pr2—O12—C73 | −8.4 (4) | C80—C75—C76—C77 | −0.4 (11) |
O9ii—Pr2—O12—C73 | −75.9 (3) | C74—C75—C76—C77 | 177.0 (7) |
O11—Pr2—O12—C73 | −1.2 (3) | C75—C76—C77—C78 | −2.0 (13) |
O10—Pr2—O12—C73 | 132.1 (3) | C76—C77—C78—C79 | 2.0 (14) |
N4—Pr2—O12—C73 | 67.8 (3) | C77—C78—C79—C84 | −179.5 (8) |
O9—Pr2—O12—C73 | −131.9 (3) | C77—C78—C79—C80 | 0.3 (12) |
N3—Pr2—O12—C73 | 129.2 (3) | C78—C79—C80—C81 | 177.1 (6) |
Pr2ii—Pr2—O12—C73 | −96.0 (3) | C84—C79—C80—C81 | −3.0 (10) |
Pr1i—O2—C1—O1 | 27.5 (8) | C78—C79—C80—C75 | −2.7 (10) |
Pr1i—O2—C1—C2 | −152.5 (4) | C84—C79—C80—C75 | 177.1 (6) |
Pr1—O1—C1—O2 | −9.6 (10) | C76—C75—C80—C81 | −177.1 (6) |
Pr1—O1—C1—C2 | 170.3 (4) | C74—C75—C80—C81 | 5.4 (9) |
O2—C1—C2—C3 | −10.1 (9) | C76—C75—C80—C79 | 2.7 (10) |
O1—C1—C2—C3 | 169.9 (6) | C74—C75—C80—C79 | −174.7 (6) |
C1—C2—C3—C4 | −104.1 (6) | C79—C80—C81—C82 | 1.9 (10) |
C1—C2—C3—C8 | 78.0 (7) | C75—C80—C81—C82 | −178.2 (6) |
C8—C3—C4—C5 | −1.8 (8) | C80—C81—C82—C83 | 0.9 (11) |
C2—C3—C4—C5 | −179.8 (5) | C81—C82—C83—C84 | −2.6 (12) |
C3—C4—C5—C6 | 0.8 (9) | C82—C83—C84—C79 | 1.4 (13) |
C4—C5—C6—C7 | −0.3 (10) | C78—C79—C84—C83 | −178.7 (8) |
C5—C6—C7—C8 | 0.8 (10) | C80—C79—C84—C83 | 1.5 (12) |
C5—C6—C7—C12 | 179.1 (7) | C89—N3—C85—C86 | 0.5 (10) |
C6—C7—C8—C9 | 178.8 (6) | Pr2—N3—C85—C86 | 179.5 (5) |
C12—C7—C8—C9 | 0.5 (8) | N3—C85—C86—C87 | −0.7 (11) |
C6—C7—C8—C3 | −1.8 (8) | C85—C86—C87—C88 | −0.1 (11) |
C12—C7—C8—C3 | 179.9 (6) | C86—C87—C88—C89 | 1.0 (10) |
C4—C3—C8—C9 | −178.3 (5) | C86—C87—C88—C95 | −179.2 (7) |
C2—C3—C8—C9 | −0.4 (8) | C85—N3—C89—C88 | 0.4 (9) |
C4—C3—C8—C7 | 2.3 (8) | Pr2—N3—C89—C88 | −178.5 (4) |
C2—C3—C8—C7 | −179.8 (5) | C85—N3—C89—C90 | −180.0 (6) |
C7—C8—C9—C10 | −0.5 (9) | Pr2—N3—C89—C90 | 1.1 (7) |
C3—C8—C9—C10 | −179.9 (6) | C87—C88—C89—N3 | −1.1 (9) |
C8—C9—C10—C11 | 1.6 (11) | C95—C88—C89—N3 | 179.0 (6) |
C9—C10—C11—C12 | −2.8 (12) | C87—C88—C89—C90 | 179.3 (6) |
C10—C11—C12—C7 | 2.8 (12) | C95—C88—C89—C90 | −0.6 (9) |
C6—C7—C12—C11 | −179.9 (7) | C94—N4—C90—C91 | −2.9 (8) |
C8—C7—C12—C11 | −1.6 (10) | Pr2—N4—C90—C91 | 177.2 (4) |
Pr1—O4—C13—O3 | 9.0 (5) | C94—N4—C90—C89 | 178.1 (5) |
Pr1—O4—C13—C14 | −171.7 (4) | Pr2—N4—C90—C89 | −1.9 (7) |
Pr1i—O3—C13—O4 | 177.0 (7) | N3—C89—C90—N4 | 0.5 (8) |
Pr1—O3—C13—O4 | −8.8 (5) | C88—C89—C90—N4 | −179.9 (5) |
Pr1i—O3—C13—C14 | −2.3 (13) | N3—C89—C90—C91 | −178.6 (5) |
Pr1—O3—C13—C14 | 171.9 (4) | C88—C89—C90—C91 | 1.0 (9) |
O4—C13—C14—C15 | 10.8 (8) | N4—C90—C91—C92 | 1.6 (9) |
O3—C13—C14—C15 | −169.9 (5) | C89—C90—C91—C92 | −179.3 (6) |
C13—C14—C15—C16 | −106.3 (7) | N4—C90—C91—C96 | −179.4 (5) |
C13—C14—C15—C20 | 73.4 (7) | C89—C90—C91—C96 | −0.3 (9) |
C20—C15—C16—C17 | −0.2 (10) | C90—C91—C92—C93 | 0.8 (9) |
C14—C15—C16—C17 | 179.5 (6) | C96—C91—C92—C93 | −178.1 (6) |
C15—C16—C17—C18 | −0.9 (12) | C91—C92—C93—C94 | −1.8 (10) |
C16—C17—C18—C19 | 2.3 (14) | C90—N4—C94—C93 | 1.8 (9) |
C17—C18—C19—C20 | −2.3 (13) | Pr2—N4—C94—C93 | −178.3 (5) |
C17—C18—C19—C24 | 178.1 (8) | C92—C93—C94—N4 | 0.6 (10) |
C16—C15—C20—C21 | −178.2 (6) | C87—C88—C95—C96 | 179.6 (7) |
C14—C15—C20—C21 | 2.0 (9) | C89—C88—C95—C96 | −0.6 (10) |
C16—C15—C20—C19 | 0.1 (9) | C88—C95—C96—C91 | 1.4 (11) |
C14—C15—C20—C19 | −179.6 (6) | C92—C91—C96—C95 | 178.0 (6) |
C18—C19—C20—C21 | 179.5 (7) | C90—C91—C96—C95 | −0.9 (10) |
C24—C19—C20—C21 | −1.0 (10) | C99—N5—C97—O13 | 178.5 (9) |
C18—C19—C20—C15 | 1.1 (10) | C98—N5—C97—O13 | −1.8 (14) |
C24—C19—C20—C15 | −179.4 (7) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26B···O13iii | 0.97 | 2.36 | 3.311 (9) | 168 |
C46—H46···O1 | 0.93 | 2.40 | 3.081 (7) | 130 |
C47—H47···O4iv | 0.93 | 2.59 | 3.377 (6) | 143 |
C85—H85···O8ii | 0.93 | 2.47 | 3.149 (7) | 130 |
C92—H92···O10v | 0.93 | 2.55 | 3.442 (7) | 160 |
C98—H98A···O13 | 0.96 | 2.37 | 2.774 (12) | 105 |
C86—H86···Cgii | 0.93 | 2.87 | 3.706 (12) | 151 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z+1; (iv) −x+1, −y+2, −z; (v) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Pr2(C12H9O2)6(C12H8N2)2]·C3H7NO |
Mr | 1826.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 13.0204 (12), 17.1379 (19), 20.417 (3) |
α, β, γ (°) | 66.336 (2), 81.554 (2), 85.998 (3) |
V (Å3) | 4127.2 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.24 |
Crystal size (mm) | 0.49 × 0.45 × 0.22 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.583, 0.773 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21619, 14351, 9934 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.100, 1.08 |
No. of reflections | 14351 |
No. of parameters | 1174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.56, −0.75 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Pr1—O3i | 2.431 (3) | Pr2—O8ii | 2.423 (4) |
Pr1—O1 | 2.434 (3) | Pr2—O7 | 2.443 (4) |
Pr1—O5 | 2.448 (3) | Pr2—O9ii | 2.447 (3) |
Pr1—O2i | 2.474 (3) | Pr2—O12 | 2.500 (4) |
Pr1—O6 | 2.548 (4) | Pr2—O11 | 2.552 (4) |
Pr1—O4 | 2.574 (4) | Pr2—O10 | 2.561 (4) |
Pr1—O3 | 2.619 (4) | Pr2—N4 | 2.635 (4) |
Pr1—N1 | 2.667 (4) | Pr2—O9 | 2.644 (4) |
Pr1—N2 | 2.670 (4) | Pr2—N3 | 2.691 (4) |
Pr1—Pr1i | 4.0072 (6) |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26B···O13iii | 0.97 | 2.36 | 3.311 (9) | 168.0 |
C46—H46···O1 | 0.93 | 2.40 | 3.081 (7) | 130.2 |
C47—H47···O4iv | 0.93 | 2.59 | 3.377 (6) | 143.3 |
C85—H85···O8ii | 0.93 | 2.47 | 3.149 (7) | 130.0 |
C92—H92···O10v | 0.93 | 2.55 | 3.442 (7) | 160.3 |
C98—H98A···O13 | 0.96 | 2.37 | 2.774 (12) | 104.7 |
C86—H86···Cgii | 0.93 | 2.87 | 3.706 (12) | 150.8 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z+1; (iv) −x+1, −y+2, −z; (v) −x+2, −y+1, −z+1. |
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Rare earth complexes with aromatic carboxylic acids are a kind of luminescent materials with good properties (Zhou et al., 2004). Generally, an organic negative ligand acts as the first ligand to the central ion while a neutral secondary ligand acts as to saturate the coordination number of the rare earth ion and also to improve the fluorescence intensity and stability of the complex. Based on this reason, some rare earth complexes with 1-naphthylacetic acid (NNA) and 1,10-phenanthroline (phen) have been synthesized (Chen & Cai, 2005), however, no report on crystal structures of rare earth complexes with NNA and phen can be found in the literature. Here, we report the synthesis and crystal structure of complex, (I).
In(I), the asymmetric unit consists of two half molecule (A and B) and one N, N-dimethylformamide (DMF) solvate. Each half molecule have a symmetric center on the central Pr—Pr bond. Each PrIII ion is nine-coordinated and the stereochemistry each PrIII ion can be described as a distorted monocapped square antiprismatic geometry (Fig. 1). The coordination modes of NNA ligands coordinated to the PrIII ion is consistent with reported Eu complex (Liu et al., 2007). The Pr1—O bond distances are 2.431 (3)–2.619 (4) Å, longer than that 2.423 (4)–2.561 (4) Å of Pr2—O. The dihedral angles between the least square-plane Pr2O2 and naphthyl rings are 42.19 (16)–71.32 (11)° for molecule A and 49.74 (16)–58.51 (16)° for molecule B.
The two molecules of (I) are linked into a chain running parallel to the [011] plane by means of C—H···π hydrogen bond and π···π stacking interaction (Fig. 2 and Table 2). The phen rings (N2C42—C46) in the molecules at (x, y, z) are inclined to one another (N3C85—C89) in the molecules at (1 - x, 1 - y, 1 - z), the separation of the two rings centroids is 3.944 (3) Å, the dihedral angles between the two rings is 2.95°. In the same way, two molecules are linked into two chains parallel to the a axis direction by C—H···O hydrogen bonds (Fig. 3 and Table 2), and these two a chains are linked into sheets parallel to the [011] plane by [011] chain. The DMF solvate molecules lie in between two sheets. However, there are no direction-specific interactions between adjacent sheets.