Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047095/at2407sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047095/at2407Isup2.hkl |
CCDC reference: 649518
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.022 Å
- R factor = 0.077
- wR factor = 0.197
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.193 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.19 PLAT342_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 22
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H50A .. O6 .. 2.62 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 36.00 A 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Tb1 (3) 3.20
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
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 Tb(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 colourless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution.
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), 0.97Å (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) (aryl, formyl, methylene) or 1.5Ueq(C) (methyl).
As a part of our investigation of the rare earth complexes with 1-naphthylacetic acid (NAA) and 1,10-phenanthroline (phen), we have recently reported the crystal structures of two complexes [Eu(NAA)3(phen)]2.2DMF (II) (Liu et al., 2007) and [Pr(NAA)3(phen)]2 .DMF (Xia et al., 2007) We report here the crystal structure of terbium complexes with NAA and phen, (I).
In the title complex, the coordination environment of Tb atom and coordination modes of the NNA ligands coordinated to the TbIII ion are in agreement with the complex (II) (Fig. 1). The average bond lengths of between the terbium center and carboxylic oxygen atoms are 2.441 (7) Å, shorter than that (2.4725 (5) Å) of complex (II). The dihedral angles of the least-square-plane Tb2O2 and naphthyl rings are 58.20 (19)° (C3—C12 ring), 43.74 (31)° (C15—C24 ring) and 71.38 (26)° (C27—C36 ring), and the dihedral angle between Tb2O2 plane and phen ring is 82.08 (21)°.
The molecules of (I) are linked into sheets by means of C—H···π hydrogen bond (Fig. 2 and Table 2) and chains parallel to the a axis direction (Fig. 3) by C—H···O hydrogen bonds (Fig. 3 and Table 2). The action of a chains are to link adjacent [100] sheet into the three-dimensional framework structure.
For related literature, see: Liu et al. (2007); Xia et al. (2007).
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).
[Tb2(C12H9O2)6(C12H8N2)2]·2C3H7NO | F(000) = 1960 |
Mr = 1935.59 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6504 reflections |
a = 13.4619 (16) Å | θ = 2.4–25.3° |
b = 15.086 (2) Å | µ = 1.67 mm−1 |
c = 22.166 (2) Å | T = 298 K |
β = 103.584 (2)° | Block, colourless |
V = 4375.6 (9) Å3 | 0.28 × 0.17 × 0.12 mm |
Z = 2 |
Bruker SMART 1000 CCD area-detector diffractometer | 7389 independent reflections |
Radiation source: fine-focus sealed tube | 4674 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.193 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→16 |
Tmin = 0.652, Tmax = 0.825 | k = −17→17 |
21422 measured reflections | l = −21→26 |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0648P)2 + 17.4888P] where P = (Fo2 + 2Fc2)/3 |
7389 reflections | (Δ/σ)max = 0.010 |
559 parameters | Δρmax = 2.20 e Å−3 |
0 restraints | Δρmin = −2.72 e Å−3 |
[Tb2(C12H9O2)6(C12H8N2)2]·2C3H7NO | V = 4375.6 (9) Å3 |
Mr = 1935.59 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4619 (16) Å | µ = 1.67 mm−1 |
b = 15.086 (2) Å | T = 298 K |
c = 22.166 (2) Å | 0.28 × 0.17 × 0.12 mm |
β = 103.584 (2)° |
Bruker SMART 1000 CCD area-detector diffractometer | 7389 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4674 reflections with I > 2σ(I) |
Tmin = 0.652, Tmax = 0.825 | Rint = 0.193 |
21422 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0648P)2 + 17.4888P] where P = (Fo2 + 2Fc2)/3 |
7389 reflections | Δρmax = 2.20 e Å−3 |
559 parameters | Δρmin = −2.72 e Å−3 |
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 | ||
Tb1 | 0.38253 (3) | 0.43006 (3) | 1.01126 (2) | 0.03377 (19) | |
N1 | 0.2316 (6) | 0.4439 (6) | 1.0645 (4) | 0.043 (2) | |
N2 | 0.2134 (6) | 0.3634 (6) | 0.9529 (4) | 0.045 (2) | |
N3 | 0.3685 (12) | 0.3365 (11) | 0.2523 (6) | 0.089 (4) | |
O1 | 0.4406 (4) | 0.5791 (5) | 0.9788 (3) | 0.0361 (15) | |
O2 | 0.2766 (5) | 0.5556 (5) | 0.9603 (3) | 0.0419 (17) | |
O3 | 0.4044 (5) | 0.4251 (5) | 0.9092 (3) | 0.0405 (16) | |
O4 | 0.5497 (5) | 0.4868 (5) | 0.8977 (3) | 0.0426 (18) | |
O5 | 0.4125 (6) | 0.2737 (5) | 0.9880 (4) | 0.052 (2) | |
O6 | 0.4021 (6) | 0.3048 (5) | 1.0822 (4) | 0.055 (2) | |
O7 | 0.2327 (12) | 0.2428 (11) | 0.2366 (8) | 0.141 (5) | |
C1 | 0.3510 (7) | 0.5982 (7) | 0.9521 (5) | 0.041 (3) | |
C2 | 0.3350 (8) | 0.6742 (9) | 0.9067 (6) | 0.058 (3) | |
H2A | 0.3780 | 0.6646 | 0.8778 | 0.070* | |
H2B | 0.3583 | 0.7282 | 0.9295 | 0.070* | |
C3 | 0.2269 (9) | 0.6888 (9) | 0.8697 (6) | 0.056 (3) | |
C4 | 0.1766 (10) | 0.7654 (9) | 0.8805 (6) | 0.067 (4) | |
H4 | 0.2098 | 0.8065 | 0.9096 | 0.080* | |
C5 | 0.0754 (11) | 0.7809 (11) | 0.8473 (7) | 0.076 (4) | |
H5 | 0.0416 | 0.8312 | 0.8563 | 0.091* | |
C6 | 0.0274 (10) | 0.7262 (11) | 0.8041 (7) | 0.073 (4) | |
H6 | −0.0388 | 0.7391 | 0.7822 | 0.088* | |
C7 | 0.0743 (10) | 0.6496 (11) | 0.7907 (7) | 0.069 (4) | |
C8 | 0.1752 (9) | 0.6298 (9) | 0.8235 (6) | 0.059 (3) | |
C9 | 0.2205 (12) | 0.5507 (11) | 0.8086 (7) | 0.076 (4) | |
H9 | 0.2872 | 0.5378 | 0.8297 | 0.092* | |
C10 | 0.1713 (13) | 0.4931 (13) | 0.7650 (8) | 0.095 (5) | |
H10 | 0.2021 | 0.4410 | 0.7563 | 0.114* | |
C11 | 0.0680 (13) | 0.5166 (14) | 0.7324 (8) | 0.097 (5) | |
H11 | 0.0321 | 0.4781 | 0.7023 | 0.116* | |
C12 | 0.0236 (13) | 0.5897 (13) | 0.7436 (8) | 0.086 (5) | |
H12 | −0.0419 | 0.6029 | 0.7207 | 0.103* | |
C13 | 0.4733 (7) | 0.4365 (7) | 0.8814 (5) | 0.041 (2) | |
C14 | 0.4627 (9) | 0.3853 (9) | 0.8215 (6) | 0.055 (3) | |
H14A | 0.4148 | 0.3372 | 0.8213 | 0.066* | |
H14B | 0.4328 | 0.4244 | 0.7873 | 0.066* | |
C15 | 0.5584 (10) | 0.3469 (9) | 0.8091 (6) | 0.061 (3) | |
C16 | 0.5901 (10) | 0.3733 (10) | 0.7564 (6) | 0.069 (4) | |
H16 | 0.5521 | 0.4155 | 0.7303 | 0.082* | |
C17 | 0.6774 (11) | 0.3380 (11) | 0.7418 (7) | 0.077 (4) | |
H17 | 0.6988 | 0.3583 | 0.7073 | 0.092* | |
C18 | 0.7313 (11) | 0.2728 (11) | 0.7791 (7) | 0.075 (4) | |
H18 | 0.7897 | 0.2494 | 0.7696 | 0.090* | |
C19 | 0.7003 (10) | 0.2412 (10) | 0.8305 (7) | 0.070 (4) | |
C20 | 0.6141 (9) | 0.2793 (9) | 0.8467 (6) | 0.061 (3) | |
C21 | 0.5847 (11) | 0.2480 (10) | 0.8994 (7) | 0.067 (4) | |
H21 | 0.5300 | 0.2742 | 0.9117 | 0.081* | |
C22 | 0.6357 (12) | 0.1798 (11) | 0.9324 (8) | 0.083 (4) | |
H22 | 0.6131 | 0.1582 | 0.9662 | 0.100* | |
C23 | 0.7221 (13) | 0.1400 (12) | 0.9176 (9) | 0.091 (5) | |
H23 | 0.7569 | 0.0941 | 0.9415 | 0.110* | |
C24 | 0.7519 (12) | 0.1707 (11) | 0.8680 (8) | 0.081 (5) | |
H24 | 0.8085 | 0.1451 | 0.8576 | 0.098* | |
C25 | 0.4093 (9) | 0.2508 (8) | 1.0418 (7) | 0.054 (3) | |
C26 | 0.4137 (11) | 0.1524 (9) | 1.0563 (7) | 0.073 (4) | |
H26A | 0.4806 | 0.1296 | 1.0550 | 0.088* | |
H26B | 0.4041 | 0.1433 | 1.0978 | 0.088* | |
C27 | 0.3350 (13) | 0.1034 (11) | 1.0117 (8) | 0.079 (4) | |
C28 | 0.3615 (15) | 0.0497 (11) | 0.9671 (9) | 0.089 (5) | |
H28 | 0.4296 | 0.0429 | 0.9659 | 0.107* | |
C29 | 0.2822 (17) | 0.0045 (12) | 0.9227 (9) | 0.101 (6) | |
H29 | 0.3005 | −0.0333 | 0.8939 | 0.121* | |
C30 | 0.1862 (18) | 0.0149 (13) | 0.9216 (10) | 0.106 (6) | |
H30 | 0.1374 | −0.0131 | 0.8908 | 0.127* | |
C31 | 0.1539 (15) | 0.0682 (12) | 0.9665 (10) | 0.096 (5) | |
C32 | 0.2307 (13) | 0.1116 (11) | 1.0113 (8) | 0.080 (4) | |
C33 | 0.1998 (12) | 0.1637 (10) | 1.0553 (9) | 0.084 (5) | |
H33 | 0.2489 | 0.1919 | 1.0857 | 0.100* | |
C34 | 0.0975 (12) | 0.1744 (11) | 1.0547 (9) | 0.088 (5) | |
H34 | 0.0774 | 0.2093 | 1.0843 | 0.106* | |
C35 | 0.0270 (15) | 0.1323 (13) | 1.0095 (11) | 0.100 (6) | |
H35 | −0.0414 | 0.1387 | 1.0103 | 0.120* | |
C36 | 0.0473 (16) | 0.0840 (13) | 0.9654 (11) | 0.104 (6) | |
H36 | −0.0046 | 0.0604 | 0.9342 | 0.125* | |
C37 | 0.2364 (8) | 0.4819 (9) | 1.1177 (6) | 0.056 (3) | |
H37 | 0.2998 | 0.5037 | 1.1386 | 0.067* | |
C38 | 0.1546 (10) | 0.4932 (9) | 1.1467 (7) | 0.066 (4) | |
H38 | 0.1633 | 0.5215 | 1.1848 | 0.080* | |
C39 | 0.0600 (9) | 0.4596 (9) | 1.1153 (7) | 0.065 (4) | |
H39 | 0.0040 | 0.4647 | 1.1330 | 0.078* | |
C40 | 0.0490 (8) | 0.4191 (8) | 1.0584 (6) | 0.055 (3) | |
C41 | 0.1391 (8) | 0.4124 (8) | 1.0345 (6) | 0.050 (3) | |
C42 | 0.1272 (8) | 0.3709 (9) | 0.9741 (6) | 0.056 (3) | |
C43 | 0.0315 (8) | 0.3372 (9) | 0.9417 (7) | 0.064 (4) | |
C44 | 0.0268 (10) | 0.2992 (10) | 0.8847 (8) | 0.077 (4) | |
H44 | −0.0352 | 0.2787 | 0.8608 | 0.092* | |
C45 | 0.1130 (10) | 0.2920 (11) | 0.8639 (7) | 0.080 (4) | |
H45 | 0.1106 | 0.2662 | 0.8255 | 0.095* | |
C46 | 0.2051 (9) | 0.3232 (9) | 0.8997 (7) | 0.063 (4) | |
H46 | 0.2638 | 0.3151 | 0.8851 | 0.075* | |
C47 | −0.0462 (9) | 0.3862 (10) | 1.0248 (8) | 0.065 (4) | |
H47 | −0.1035 | 0.3925 | 1.0410 | 0.078* | |
C48 | −0.0549 (9) | 0.3465 (10) | 0.9703 (7) | 0.068 (4) | |
H48 | −0.1181 | 0.3238 | 0.9498 | 0.082* | |
C49 | 0.3092 (17) | 0.2712 (17) | 0.2221 (10) | 0.108 (6) | |
H49 | 0.3275 | 0.2459 | 0.1880 | 0.129* | |
C50 | 0.4600 (14) | 0.3654 (13) | 0.2341 (8) | 0.100 (6) | |
H50A | 0.4724 | 0.3271 | 0.2020 | 0.151* | |
H50B | 0.5172 | 0.3631 | 0.2693 | 0.151* | |
H50C | 0.4508 | 0.4251 | 0.2187 | 0.151* | |
C51 | 0.3405 (18) | 0.3704 (16) | 0.3046 (10) | 0.136 (8) | |
H51A | 0.2707 | 0.3550 | 0.3030 | 0.205* | |
H51B | 0.3475 | 0.4337 | 0.3054 | 0.205* | |
H51C | 0.3839 | 0.3457 | 0.3414 | 0.205* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Tb1 | 0.0240 (2) | 0.0402 (3) | 0.0367 (3) | −0.0027 (2) | 0.00618 (17) | −0.0022 (3) |
N1 | 0.033 (4) | 0.050 (5) | 0.047 (5) | 0.004 (4) | 0.014 (4) | 0.004 (5) |
N2 | 0.028 (4) | 0.060 (6) | 0.047 (5) | −0.009 (4) | 0.006 (4) | −0.011 (5) |
N3 | 0.108 (11) | 0.096 (10) | 0.063 (8) | 0.027 (9) | 0.021 (8) | 0.033 (9) |
O1 | 0.019 (3) | 0.047 (4) | 0.038 (4) | 0.001 (3) | −0.001 (3) | −0.005 (4) |
O2 | 0.030 (3) | 0.050 (4) | 0.045 (4) | 0.005 (3) | 0.006 (3) | 0.011 (4) |
O3 | 0.028 (3) | 0.049 (4) | 0.041 (4) | −0.005 (3) | 0.002 (3) | −0.001 (4) |
O4 | 0.044 (4) | 0.051 (4) | 0.036 (4) | −0.003 (4) | 0.016 (3) | −0.012 (4) |
O5 | 0.063 (5) | 0.045 (4) | 0.050 (5) | −0.014 (4) | 0.020 (4) | −0.009 (4) |
O6 | 0.051 (4) | 0.054 (5) | 0.061 (5) | −0.005 (4) | 0.017 (4) | 0.000 (5) |
O7 | 0.110 (11) | 0.150 (13) | 0.155 (13) | 0.000 (10) | 0.014 (9) | 0.046 (13) |
C1 | 0.029 (5) | 0.044 (6) | 0.051 (6) | −0.003 (4) | 0.013 (5) | −0.007 (6) |
C2 | 0.042 (6) | 0.066 (8) | 0.062 (8) | −0.001 (6) | 0.004 (5) | 0.020 (8) |
C3 | 0.044 (6) | 0.065 (8) | 0.058 (8) | 0.005 (6) | 0.009 (6) | 0.018 (7) |
C4 | 0.058 (8) | 0.067 (9) | 0.069 (9) | 0.008 (7) | 0.003 (6) | 0.020 (8) |
C5 | 0.065 (8) | 0.081 (10) | 0.077 (10) | 0.018 (8) | 0.007 (7) | 0.020 (10) |
C6 | 0.053 (7) | 0.086 (11) | 0.073 (10) | 0.010 (8) | 0.000 (7) | 0.025 (10) |
C7 | 0.058 (8) | 0.078 (10) | 0.062 (9) | −0.008 (8) | −0.001 (6) | 0.022 (9) |
C8 | 0.048 (7) | 0.072 (9) | 0.056 (8) | −0.001 (6) | 0.009 (6) | 0.021 (8) |
C9 | 0.071 (9) | 0.076 (10) | 0.069 (10) | 0.005 (8) | −0.009 (7) | 0.010 (10) |
C10 | 0.092 (12) | 0.090 (12) | 0.087 (12) | 0.004 (10) | −0.013 (9) | 0.007 (12) |
C11 | 0.092 (12) | 0.097 (14) | 0.081 (12) | −0.004 (11) | −0.022 (9) | 0.010 (12) |
C12 | 0.073 (10) | 0.091 (12) | 0.078 (11) | −0.002 (9) | −0.016 (8) | 0.015 (11) |
C13 | 0.033 (5) | 0.047 (6) | 0.042 (6) | −0.011 (5) | 0.009 (4) | −0.012 (6) |
C14 | 0.054 (7) | 0.064 (8) | 0.051 (7) | 0.001 (6) | 0.019 (6) | −0.016 (7) |
C15 | 0.062 (7) | 0.068 (8) | 0.058 (8) | −0.010 (7) | 0.024 (6) | −0.028 (8) |
C16 | 0.074 (9) | 0.075 (9) | 0.062 (8) | −0.005 (7) | 0.027 (7) | −0.024 (8) |
C17 | 0.080 (10) | 0.090 (11) | 0.069 (9) | −0.009 (9) | 0.036 (8) | −0.026 (10) |
C18 | 0.069 (9) | 0.085 (11) | 0.078 (10) | −0.006 (8) | 0.028 (8) | −0.034 (10) |
C19 | 0.065 (8) | 0.073 (9) | 0.076 (10) | −0.005 (7) | 0.022 (7) | −0.035 (9) |
C20 | 0.057 (7) | 0.064 (8) | 0.064 (8) | −0.006 (7) | 0.020 (6) | −0.029 (8) |
C21 | 0.067 (8) | 0.066 (9) | 0.069 (9) | −0.006 (7) | 0.017 (7) | −0.021 (9) |
C22 | 0.080 (10) | 0.079 (11) | 0.086 (11) | 0.005 (9) | 0.008 (9) | −0.014 (11) |
C23 | 0.082 (11) | 0.085 (11) | 0.096 (13) | 0.005 (9) | −0.003 (9) | −0.017 (12) |
C24 | 0.069 (9) | 0.078 (11) | 0.094 (12) | 0.000 (8) | 0.014 (9) | −0.030 (11) |
C25 | 0.039 (6) | 0.051 (7) | 0.074 (9) | −0.005 (5) | 0.015 (6) | 0.010 (8) |
C26 | 0.072 (9) | 0.065 (9) | 0.080 (10) | −0.004 (8) | 0.011 (8) | 0.014 (9) |
C27 | 0.091 (11) | 0.056 (8) | 0.087 (11) | −0.012 (8) | 0.016 (9) | 0.022 (9) |
C28 | 0.102 (12) | 0.066 (10) | 0.095 (12) | −0.015 (9) | 0.014 (10) | 0.013 (11) |
C29 | 0.125 (17) | 0.076 (11) | 0.097 (14) | −0.012 (12) | 0.015 (12) | 0.014 (12) |
C30 | 0.116 (16) | 0.077 (12) | 0.109 (15) | −0.023 (12) | −0.006 (12) | 0.023 (13) |
C31 | 0.101 (14) | 0.069 (11) | 0.109 (15) | −0.018 (10) | 0.006 (11) | 0.023 (12) |
C32 | 0.086 (11) | 0.058 (8) | 0.090 (12) | −0.016 (8) | 0.007 (9) | 0.019 (10) |
C33 | 0.077 (10) | 0.067 (9) | 0.106 (13) | −0.012 (8) | 0.019 (9) | 0.019 (11) |
C34 | 0.075 (10) | 0.075 (10) | 0.109 (13) | −0.007 (9) | 0.011 (9) | 0.018 (11) |
C35 | 0.087 (12) | 0.078 (12) | 0.125 (17) | −0.020 (10) | 0.003 (12) | 0.018 (14) |
C36 | 0.102 (15) | 0.081 (13) | 0.114 (16) | −0.021 (11) | −0.004 (11) | 0.023 (13) |
C37 | 0.036 (6) | 0.076 (8) | 0.061 (8) | 0.004 (6) | 0.025 (6) | 0.010 (8) |
C38 | 0.056 (8) | 0.078 (9) | 0.074 (9) | 0.009 (7) | 0.033 (7) | 0.011 (9) |
C39 | 0.052 (7) | 0.072 (8) | 0.079 (9) | 0.007 (7) | 0.033 (7) | 0.017 (9) |
C40 | 0.031 (5) | 0.063 (8) | 0.077 (9) | 0.004 (5) | 0.024 (6) | 0.017 (8) |
C41 | 0.032 (5) | 0.059 (7) | 0.066 (7) | −0.001 (5) | 0.023 (5) | 0.008 (7) |
C42 | 0.034 (6) | 0.063 (8) | 0.070 (9) | −0.007 (5) | 0.015 (6) | 0.008 (7) |
C43 | 0.034 (6) | 0.067 (8) | 0.090 (10) | −0.010 (6) | 0.012 (6) | 0.005 (9) |
C44 | 0.052 (8) | 0.079 (10) | 0.093 (11) | −0.019 (7) | 0.004 (7) | −0.001 (10) |
C45 | 0.052 (8) | 0.094 (11) | 0.084 (10) | −0.020 (8) | −0.001 (7) | −0.009 (10) |
C46 | 0.039 (6) | 0.076 (9) | 0.074 (9) | −0.006 (6) | 0.014 (6) | −0.005 (8) |
C47 | 0.035 (6) | 0.067 (8) | 0.096 (11) | −0.001 (6) | 0.023 (7) | 0.025 (9) |
C48 | 0.033 (6) | 0.072 (9) | 0.096 (11) | −0.015 (6) | 0.008 (6) | 0.014 (10) |
C49 | 0.101 (14) | 0.126 (18) | 0.089 (13) | 0.005 (13) | 0.007 (11) | 0.029 (15) |
C50 | 0.108 (13) | 0.103 (13) | 0.091 (12) | 0.015 (11) | 0.025 (10) | 0.039 (12) |
C51 | 0.16 (2) | 0.14 (2) | 0.113 (17) | 0.043 (17) | 0.030 (15) | −0.003 (18) |
Tb1—O1i | 2.343 (5) | C19—C20 | 1.415 (16) |
Tb1—O3 | 2.349 (6) | C19—C24 | 1.43 (2) |
Tb1—O4i | 2.369 (7) | C20—C21 | 1.400 (18) |
Tb1—O6 | 2.433 (8) | C21—C22 | 1.35 (2) |
Tb1—O5 | 2.468 (8) | C21—H21 | 0.9300 |
Tb1—O2 | 2.478 (7) | C22—C23 | 1.41 (2) |
Tb1—O1 | 2.539 (7) | C22—H22 | 0.9300 |
Tb1—N2 | 2.547 (9) | C23—C24 | 1.34 (2) |
Tb1—N1 | 2.587 (7) | C23—H23 | 0.9300 |
Tb1—Tb1i | 3.9302 (9) | C24—H24 | 0.9300 |
N1—C37 | 1.299 (14) | C25—C26 | 1.518 (18) |
N1—C41 | 1.352 (15) | C26—C27 | 1.47 (2) |
N2—C46 | 1.306 (15) | C26—H26A | 0.9700 |
N2—C42 | 1.356 (12) | C26—H26B | 0.9700 |
N3—C49 | 1.34 (2) | C27—C28 | 1.39 (2) |
N3—C51 | 1.40 (2) | C27—C32 | 1.41 (2) |
N3—C50 | 1.45 (2) | C28—C29 | 1.44 (2) |
O1—C1 | 1.247 (12) | C28—H28 | 0.9300 |
O1—Tb1i | 2.343 (5) | C29—C30 | 1.30 (2) |
O2—C1 | 1.239 (11) | C29—H29 | 0.9300 |
O3—C13 | 1.241 (10) | C30—C31 | 1.43 (3) |
O4—C13 | 1.262 (11) | C30—H30 | 0.9300 |
O4—Tb1i | 2.369 (7) | C31—C32 | 1.41 (3) |
O5—C25 | 1.252 (15) | C31—C36 | 1.45 (3) |
O6—C25 | 1.231 (14) | C32—C33 | 1.39 (2) |
O7—C49 | 1.23 (2) | C33—C34 | 1.38 (2) |
C1—C2 | 1.507 (16) | C33—H33 | 0.9300 |
C2—C3 | 1.509 (16) | C34—C35 | 1.37 (3) |
C2—H2A | 0.9700 | C34—H34 | 0.9300 |
C2—H2B | 0.9700 | C35—C36 | 1.30 (3) |
C3—C4 | 1.388 (18) | C35—H35 | 0.9300 |
C3—C8 | 1.411 (18) | C36—H36 | 0.9300 |
C4—C5 | 1.407 (19) | C37—C38 | 1.410 (13) |
C4—H4 | 0.9300 | C37—H37 | 0.9300 |
C5—C6 | 1.31 (2) | C38—C39 | 1.395 (19) |
C5—H5 | 0.9300 | C38—H38 | 0.9300 |
C6—C7 | 1.38 (2) | C39—C40 | 1.378 (19) |
C6—H6 | 0.9300 | C39—H39 | 0.9300 |
C7—C8 | 1.413 (18) | C40—C47 | 1.412 (19) |
C7—C12 | 1.43 (2) | C40—C41 | 1.437 (12) |
C8—C9 | 1.41 (2) | C41—C42 | 1.453 (17) |
C9—C10 | 1.35 (2) | C42—C43 | 1.413 (17) |
C9—H9 | 0.9300 | C43—C44 | 1.375 (19) |
C10—C11 | 1.45 (2) | C43—C48 | 1.456 (16) |
C10—H10 | 0.9300 | C44—C45 | 1.351 (17) |
C11—C12 | 1.31 (2) | C44—H44 | 0.9300 |
C11—H11 | 0.9300 | C45—C46 | 1.388 (18) |
C12—H12 | 0.9300 | C45—H45 | 0.9300 |
C13—C14 | 1.513 (15) | C46—H46 | 0.9300 |
C14—C15 | 1.495 (15) | C47—C48 | 1.328 (19) |
C14—H14A | 0.9700 | C47—H47 | 0.9300 |
C14—H14B | 0.9700 | C48—H48 | 0.9300 |
C15—C16 | 1.393 (17) | C49—H49 | 0.9300 |
C15—C20 | 1.416 (19) | C50—H50A | 0.9600 |
C16—C17 | 1.395 (17) | C50—H50B | 0.9600 |
C16—H16 | 0.9300 | C50—H50C | 0.9600 |
C17—C18 | 1.38 (2) | C51—H51A | 0.9600 |
C17—H17 | 0.9300 | C51—H51B | 0.9600 |
C18—C19 | 1.39 (2) | C51—H51C | 0.9600 |
C18—H18 | 0.9300 | ||
O1i—Tb1—O3 | 74.6 (2) | C17—C16—H16 | 119.1 |
O1i—Tb1—O4i | 76.8 (2) | C18—C17—C16 | 119.0 (13) |
O3—Tb1—O4i | 136.6 (2) | C18—C17—H17 | 120.5 |
O1i—Tb1—O6 | 86.6 (2) | C16—C17—H17 | 120.5 |
O3—Tb1—O6 | 125.4 (3) | C17—C18—C19 | 121.4 (13) |
O4i—Tb1—O6 | 84.2 (3) | C17—C18—H18 | 119.3 |
O1i—Tb1—O5 | 75.6 (2) | C19—C18—H18 | 119.3 |
O3—Tb1—O5 | 72.9 (2) | C18—C19—C20 | 119.5 (15) |
O4i—Tb1—O5 | 129.4 (3) | C18—C19—C24 | 122.4 (13) |
O6—Tb1—O5 | 52.7 (3) | C20—C19—C24 | 118.2 (13) |
O1i—Tb1—O2 | 123.5 (2) | C21—C20—C19 | 119.0 (14) |
O3—Tb1—O2 | 77.0 (2) | C21—C20—C15 | 121.3 (11) |
O4i—Tb1—O2 | 92.8 (2) | C19—C20—C15 | 119.7 (12) |
O6—Tb1—O2 | 148.4 (2) | C22—C21—C20 | 120.0 (13) |
O5—Tb1—O2 | 137.8 (3) | C22—C21—H21 | 120.0 |
O1i—Tb1—O1 | 72.8 (3) | C20—C21—H21 | 120.0 |
O3—Tb1—O1 | 68.8 (2) | C21—C22—C23 | 122.5 (16) |
O4i—Tb1—O1 | 72.0 (2) | C21—C22—H22 | 118.7 |
O6—Tb1—O1 | 151.3 (3) | C23—C22—H22 | 118.7 |
O5—Tb1—O1 | 135.3 (2) | C24—C23—C22 | 117.8 (18) |
O2—Tb1—O1 | 51.5 (2) | C24—C23—H23 | 121.1 |
O1i—Tb1—N2 | 142.4 (2) | C22—C23—H23 | 121.1 |
O3—Tb1—N2 | 78.3 (2) | C23—C24—C19 | 122.5 (14) |
O4i—Tb1—N2 | 139.6 (2) | C23—C24—H24 | 118.8 |
O6—Tb1—N2 | 88.3 (3) | C19—C24—H24 | 118.8 |
O5—Tb1—N2 | 71.7 (3) | O6—C25—O5 | 122.5 (11) |
O2—Tb1—N2 | 73.8 (3) | O6—C25—C26 | 120.0 (12) |
O1—Tb1—N2 | 120.3 (3) | O5—C25—C26 | 117.5 (13) |
O1i—Tb1—N1 | 148.4 (3) | C27—C26—C25 | 111.4 (13) |
O3—Tb1—N1 | 137.0 (3) | C27—C26—H26A | 109.4 |
O4i—Tb1—N1 | 75.8 (3) | C25—C26—H26A | 109.4 |
O6—Tb1—N1 | 75.2 (3) | C27—C26—H26B | 109.4 |
O5—Tb1—N1 | 110.9 (3) | C25—C26—H26B | 109.4 |
O2—Tb1—N1 | 73.5 (2) | H26A—C26—H26B | 108.0 |
O1—Tb1—N1 | 112.7 (2) | C28—C27—C32 | 118.1 (17) |
N2—Tb1—N1 | 63.9 (3) | C28—C27—C26 | 120.5 (15) |
O1i—Tb1—Tb1i | 38.12 (17) | C32—C27—C26 | 121.4 (16) |
O3—Tb1—Tb1i | 66.94 (16) | C27—C28—C29 | 119.3 (18) |
O4i—Tb1—Tb1i | 70.35 (15) | C27—C28—H28 | 120.3 |
O6—Tb1—Tb1i | 122.06 (18) | C29—C28—H28 | 120.3 |
O5—Tb1—Tb1i | 108.12 (16) | C30—C29—C28 | 122 (2) |
O2—Tb1—Tb1i | 85.76 (15) | C30—C29—H29 | 119.0 |
O1—Tb1—Tb1i | 34.72 (13) | C28—C29—H29 | 119.0 |
N2—Tb1—Tb1i | 142.9 (2) | C29—C30—C31 | 121 (2) |
N1—Tb1—Tb1i | 139.2 (2) | C29—C30—H30 | 119.3 |
C37—N1—C41 | 116.4 (8) | C31—C30—H30 | 119.3 |
C37—N1—Tb1 | 124.9 (7) | C32—C31—C30 | 117.4 (19) |
C41—N1—Tb1 | 118.6 (7) | C32—C31—C36 | 120 (2) |
C46—N2—C42 | 116.9 (10) | C30—C31—C36 | 123 (2) |
C46—N2—Tb1 | 121.3 (6) | C33—C32—C27 | 120.6 (16) |
C42—N2—Tb1 | 121.8 (8) | C33—C32—C31 | 117.7 (17) |
C49—N3—C51 | 115.9 (18) | C27—C32—C31 | 121.8 (18) |
C49—N3—C50 | 121.6 (16) | C34—C33—C32 | 121.4 (17) |
C51—N3—C50 | 122 (2) | C34—C33—H33 | 119.3 |
C1—O1—Tb1i | 155.2 (6) | C32—C33—H33 | 119.3 |
C1—O1—Tb1 | 90.6 (6) | C35—C34—C33 | 118.1 (19) |
Tb1i—O1—Tb1 | 107.2 (2) | C35—C34—H34 | 120.9 |
C1—O2—Tb1 | 93.7 (6) | C33—C34—H34 | 120.9 |
C13—O3—Tb1 | 138.8 (7) | C36—C35—C34 | 125 (2) |
C13—O4—Tb1i | 133.5 (6) | C36—C35—H35 | 117.3 |
C25—O5—Tb1 | 91.2 (7) | C34—C35—H35 | 117.3 |
C25—O6—Tb1 | 93.3 (7) | C35—C36—C31 | 118 (2) |
O2—C1—O1 | 122.4 (10) | C35—C36—H36 | 121.2 |
O2—C1—C2 | 119.9 (9) | C31—C36—H36 | 121.2 |
O1—C1—C2 | 117.6 (8) | N1—C37—C38 | 126.1 (12) |
C1—C2—C3 | 116.3 (9) | N1—C37—H37 | 116.9 |
C1—C2—H2A | 108.2 | C38—C37—H37 | 116.9 |
C3—C2—H2A | 108.2 | C39—C38—C37 | 116.7 (13) |
C1—C2—H2B | 108.2 | C39—C38—H38 | 121.7 |
C3—C2—H2B | 108.2 | C37—C38—H38 | 121.7 |
H2A—C2—H2B | 107.4 | C40—C39—C38 | 120.4 (10) |
C4—C3—C8 | 118.2 (12) | C40—C39—H39 | 119.8 |
C4—C3—C2 | 118.4 (13) | C38—C39—H39 | 119.8 |
C8—C3—C2 | 123.4 (11) | C39—C40—C47 | 121.9 (10) |
C3—C4—C5 | 120.0 (15) | C39—C40—C41 | 116.7 (11) |
C3—C4—H4 | 120.0 | C47—C40—C41 | 121.3 (13) |
C5—C4—H4 | 120.0 | N1—C41—C40 | 123.7 (11) |
C6—C5—C4 | 121.8 (14) | N1—C41—C42 | 119.6 (8) |
C6—C5—H5 | 119.1 | C40—C41—C42 | 116.7 (11) |
C4—C5—H5 | 119.1 | N2—C42—C43 | 123.1 (12) |
C5—C6—C7 | 120.7 (14) | N2—C42—C41 | 116.0 (10) |
C5—C6—H6 | 119.7 | C43—C42—C41 | 120.9 (10) |
C7—C6—H6 | 119.7 | C44—C43—C42 | 117.2 (10) |
C6—C7—C8 | 119.9 (15) | C44—C43—C48 | 124.8 (12) |
C6—C7—C12 | 121.4 (15) | C42—C43—C48 | 118.0 (13) |
C8—C7—C12 | 118.7 (14) | C45—C44—C43 | 119.3 (13) |
C3—C8—C7 | 119.4 (13) | C45—C44—H44 | 120.3 |
C3—C8—C9 | 122.4 (13) | C43—C44—H44 | 120.3 |
C7—C8—C9 | 118.2 (14) | C44—C45—C46 | 120.0 (15) |
C10—C9—C8 | 122.9 (15) | C44—C45—H45 | 120.0 |
C10—C9—H9 | 118.5 | C46—C45—H45 | 120.0 |
C8—C9—H9 | 118.5 | N2—C46—C45 | 123.3 (11) |
C9—C10—C11 | 116.7 (17) | N2—C46—H46 | 118.3 |
C9—C10—H10 | 121.6 | C45—C46—H46 | 118.3 |
C11—C10—H10 | 121.6 | C48—C47—C40 | 121.0 (10) |
C12—C11—C10 | 122.6 (19) | C48—C47—H47 | 119.5 |
C12—C11—H11 | 118.7 | C40—C47—H47 | 119.5 |
C10—C11—H11 | 118.7 | C47—C48—C43 | 122.0 (12) |
C11—C12—C7 | 120.8 (17) | C47—C48—H48 | 119.0 |
C11—C12—H12 | 119.6 | C43—C48—H48 | 119.0 |
C7—C12—H12 | 119.6 | O7—C49—N3 | 124 (2) |
O3—C13—O4 | 126.5 (9) | O7—C49—H49 | 117.9 |
O3—C13—C14 | 116.1 (9) | N3—C49—H49 | 117.9 |
O4—C13—C14 | 117.4 (8) | N3—C50—H50A | 109.5 |
C15—C14—C13 | 116.8 (10) | N3—C50—H50B | 109.5 |
C15—C14—H14A | 108.1 | H50A—C50—H50B | 109.5 |
C13—C14—H14A | 108.1 | N3—C50—H50C | 109.5 |
C15—C14—H14B | 108.1 | H50A—C50—H50C | 109.5 |
C13—C14—H14B | 108.1 | H50B—C50—H50C | 109.5 |
H14A—C14—H14B | 107.3 | N3—C51—H51A | 109.5 |
C16—C15—C20 | 118.4 (11) | N3—C51—H51B | 109.5 |
C16—C15—C14 | 119.3 (13) | H51A—C51—H51B | 109.5 |
C20—C15—C14 | 122.1 (10) | N3—C51—H51C | 109.5 |
C15—C16—C17 | 121.8 (15) | H51A—C51—H51C | 109.5 |
C15—C16—H16 | 119.1 | H51B—C51—H51C | 109.5 |
O1i—Tb1—N1—C37 | 27.9 (11) | C6—C7—C8—C3 | 0.1 (18) |
O3—Tb1—N1—C37 | −148.8 (8) | C12—C7—C8—C3 | 179.2 (11) |
O4i—Tb1—N1—C37 | −2.9 (9) | C6—C7—C8—C9 | 179.9 (12) |
O6—Tb1—N1—C37 | 84.7 (9) | C12—C7—C8—C9 | −0.9 (18) |
O5—Tb1—N1—C37 | 124.3 (9) | C3—C8—C9—C10 | 179.2 (14) |
O2—Tb1—N1—C37 | −100.2 (9) | C7—C8—C9—C10 | −1 (2) |
O1—Tb1—N1—C37 | −66.0 (9) | C8—C9—C10—C11 | 1 (2) |
N2—Tb1—N1—C37 | −179.8 (10) | C9—C10—C11—C12 | 0 (3) |
Tb1i—Tb1—N1—C37 | −37.6 (10) | C10—C11—C12—C7 | −2 (3) |
O1i—Tb1—N1—C41 | −154.6 (7) | C6—C7—C12—C11 | −178.6 (16) |
O3—Tb1—N1—C41 | 28.7 (10) | C8—C7—C12—C11 | 2 (2) |
O4i—Tb1—N1—C41 | 174.6 (8) | Tb1—O3—C13—O4 | −28.8 (18) |
O6—Tb1—N1—C41 | −97.8 (8) | Tb1—O3—C13—C14 | 152.1 (8) |
O5—Tb1—N1—C41 | −58.2 (8) | Tb1i—O4—C13—O3 | 8.6 (17) |
O2—Tb1—N1—C41 | 77.3 (8) | Tb1i—O4—C13—C14 | −172.3 (7) |
O1—Tb1—N1—C41 | 111.4 (8) | O3—C13—C14—C15 | −140.2 (12) |
N2—Tb1—N1—C41 | −2.3 (8) | O4—C13—C14—C15 | 40.6 (16) |
Tb1i—Tb1—N1—C41 | 139.9 (7) | C13—C14—C15—C16 | −119.7 (13) |
O1i—Tb1—N2—C46 | −22.3 (11) | C13—C14—C15—C20 | 65.3 (16) |
O3—Tb1—N2—C46 | 22.3 (9) | C20—C15—C16—C17 | −3 (2) |
O4i—Tb1—N2—C46 | 176.7 (8) | C14—C15—C16—C17 | −178.4 (13) |
O6—Tb1—N2—C46 | −104.4 (9) | C15—C16—C17—C18 | 3 (2) |
O5—Tb1—N2—C46 | −53.3 (9) | C16—C17—C18—C19 | 0 (2) |
O2—Tb1—N2—C46 | 102.0 (9) | C17—C18—C19—C20 | −3 (2) |
O1—Tb1—N2—C46 | 79.1 (10) | C17—C18—C19—C24 | 176.8 (14) |
N1—Tb1—N2—C46 | −178.7 (10) | C18—C19—C20—C21 | −178.8 (12) |
Tb1i—Tb1—N2—C46 | 42.8 (11) | C24—C19—C20—C21 | 1.6 (19) |
O1i—Tb1—N2—C42 | 160.4 (8) | C18—C19—C20—C15 | 2.2 (19) |
O3—Tb1—N2—C42 | −155.0 (9) | C24—C19—C20—C15 | −177.4 (12) |
O4i—Tb1—N2—C42 | −0.6 (11) | C16—C15—C20—C21 | −178.2 (13) |
O6—Tb1—N2—C42 | 78.3 (9) | C14—C15—C20—C21 | −3.2 (18) |
O5—Tb1—N2—C42 | 129.4 (9) | C16—C15—C20—C19 | 0.7 (18) |
O2—Tb1—N2—C42 | −75.3 (9) | C14—C15—C20—C19 | 175.7 (12) |
O1—Tb1—N2—C42 | −98.2 (9) | C19—C20—C21—C22 | −3 (2) |
N1—Tb1—N2—C42 | 3.9 (8) | C15—C20—C21—C22 | 176.1 (13) |
Tb1i—Tb1—N2—C42 | −134.5 (8) | C20—C21—C22—C23 | 3 (2) |
O1i—Tb1—O1—C1 | 162.4 (7) | C21—C22—C23—C24 | −1 (2) |
O3—Tb1—O1—C1 | 82.7 (6) | C22—C23—C24—C19 | 0 (2) |
O4i—Tb1—O1—C1 | −116.3 (6) | C18—C19—C24—C23 | −179.9 (15) |
O6—Tb1—O1—C1 | −151.6 (6) | C20—C19—C24—C23 | 0 (2) |
O5—Tb1—O1—C1 | 115.4 (6) | Tb1—O6—C25—O5 | 5.3 (11) |
O2—Tb1—O1—C1 | −7.3 (5) | Tb1—O6—C25—C26 | −174.2 (11) |
N2—Tb1—O1—C1 | 21.2 (6) | Tb1—O5—C25—O6 | −5.3 (11) |
N1—Tb1—O1—C1 | −50.8 (6) | Tb1—O5—C25—C26 | 174.3 (10) |
Tb1i—Tb1—O1—C1 | 162.4 (7) | O6—C25—C26—C27 | 125.9 (14) |
O1i—Tb1—O1—Tb1i | 0.0 | O5—C25—C26—C27 | −53.6 (16) |
O3—Tb1—O1—Tb1i | −79.7 (3) | C25—C26—C27—C28 | 107.4 (16) |
O4i—Tb1—O1—Tb1i | 81.3 (3) | C25—C26—C27—C32 | −70.4 (17) |
O6—Tb1—O1—Tb1i | 46.0 (6) | C32—C27—C28—C29 | 0 (2) |
O5—Tb1—O1—Tb1i | −47.0 (4) | C26—C27—C28—C29 | −178.1 (14) |
O2—Tb1—O1—Tb1i | −169.7 (4) | C27—C28—C29—C30 | 2 (3) |
N2—Tb1—O1—Tb1i | −141.2 (3) | C28—C29—C30—C31 | −3 (3) |
N1—Tb1—O1—Tb1i | 146.8 (3) | C29—C30—C31—C32 | 2 (2) |
O1i—Tb1—O2—C1 | −4.4 (7) | C29—C30—C31—C36 | 177.6 (17) |
O3—Tb1—O2—C1 | −65.8 (6) | C28—C27—C32—C33 | 179.3 (14) |
O4i—Tb1—O2—C1 | 71.5 (6) | C26—C27—C32—C33 | −3 (2) |
O6—Tb1—O2—C1 | 155.0 (6) | C28—C27—C32—C31 | −1 (2) |
O5—Tb1—O2—C1 | −111.0 (6) | C26—C27—C32—C31 | 176.6 (14) |
O1—Tb1—O2—C1 | 7.4 (6) | C30—C31—C32—C33 | −180.0 (14) |
N2—Tb1—O2—C1 | −147.2 (6) | C36—C31—C32—C33 | 4 (2) |
N1—Tb1—O2—C1 | 145.9 (7) | C30—C31—C32—C27 | 1 (2) |
Tb1i—Tb1—O2—C1 | 1.5 (6) | C36—C31—C32—C27 | −175.5 (14) |
O1i—Tb1—O3—C13 | −17.2 (10) | C27—C32—C33—C34 | 178.3 (14) |
O4i—Tb1—O3—C13 | 33.3 (11) | C31—C32—C33—C34 | −1 (2) |
O6—Tb1—O3—C13 | −91.4 (10) | C32—C33—C34—C35 | 0 (2) |
O5—Tb1—O3—C13 | −96.6 (10) | C33—C34—C35—C36 | −2 (3) |
O2—Tb1—O3—C13 | 113.4 (10) | C34—C35—C36—C31 | 5 (3) |
O1—Tb1—O3—C13 | 60.0 (10) | C32—C31—C36—C35 | −6 (2) |
N2—Tb1—O3—C13 | −170.8 (11) | C30—C31—C36—C35 | 178.6 (17) |
N1—Tb1—O3—C13 | 161.0 (9) | C41—N1—C37—C38 | 0.0 (18) |
Tb1i—Tb1—O3—C13 | 22.5 (10) | Tb1—N1—C37—C38 | 177.6 (10) |
O1i—Tb1—O5—C25 | 99.6 (7) | N1—C37—C38—C39 | 0 (2) |
O3—Tb1—O5—C25 | 177.6 (7) | C37—C38—C39—C40 | −1.0 (19) |
O4i—Tb1—O5—C25 | 40.6 (7) | C38—C39—C40—C47 | −178.6 (12) |
O6—Tb1—O5—C25 | 2.8 (6) | C38—C39—C40—C41 | 1.0 (18) |
O2—Tb1—O5—C25 | −136.1 (6) | C37—N1—C41—C40 | −0.1 (16) |
O1—Tb1—O5—C25 | 145.7 (6) | Tb1—N1—C41—C40 | −177.8 (8) |
N2—Tb1—O5—C25 | −99.4 (7) | C37—N1—C41—C42 | 178.6 (11) |
N1—Tb1—O5—C25 | −47.9 (7) | Tb1—N1—C41—C42 | 0.9 (14) |
Tb1i—Tb1—O5—C25 | 119.7 (6) | C39—C40—C41—N1 | −0.5 (17) |
O1i—Tb1—O6—C25 | −77.4 (6) | C47—C40—C41—N1 | 179.1 (11) |
O3—Tb1—O6—C25 | −9.0 (7) | C39—C40—C41—C42 | −179.1 (11) |
O4i—Tb1—O6—C25 | −154.4 (7) | C47—C40—C41—C42 | 0.4 (17) |
O5—Tb1—O6—C25 | −2.9 (6) | C46—N2—C42—C43 | 0.4 (18) |
O2—Tb1—O6—C25 | 119.7 (7) | Tb1—N2—C42—C43 | 177.8 (10) |
O1—Tb1—O6—C25 | −120.9 (7) | C46—N2—C42—C41 | 177.5 (11) |
N2—Tb1—O6—C25 | 65.4 (7) | Tb1—N2—C42—C41 | −5.1 (14) |
N1—Tb1—O6—C25 | 128.7 (7) | N1—C41—C42—N2 | 2.7 (16) |
Tb1i—Tb1—O6—C25 | −92.0 (7) | C40—C41—C42—N2 | −178.6 (11) |
Tb1—O2—C1—O1 | −14.0 (10) | N1—C41—C42—C43 | 179.9 (12) |
Tb1—O2—C1—C2 | 163.7 (9) | C40—C41—C42—C43 | −1.4 (17) |
Tb1i—O1—C1—O2 | 150.2 (11) | N2—C42—C43—C44 | −3 (2) |
Tb1—O1—C1—O2 | 13.6 (10) | C41—C42—C43—C44 | 179.7 (12) |
Tb1i—O1—C1—C2 | −28 (2) | N2—C42—C43—C48 | 177.8 (12) |
Tb1—O1—C1—C2 | −164.1 (9) | C41—C42—C43—C48 | 0.8 (19) |
O2—C1—C2—C3 | −4.7 (16) | C42—C43—C44—C45 | 3 (2) |
O1—C1—C2—C3 | 173.1 (10) | C48—C43—C44—C45 | −178.0 (14) |
C1—C2—C3—C4 | 112.9 (13) | C43—C44—C45—C46 | 0 (2) |
C1—C2—C3—C8 | −68.9 (15) | C42—N2—C46—C45 | 2.7 (19) |
C8—C3—C4—C5 | 2.3 (18) | Tb1—N2—C46—C45 | −174.7 (11) |
C2—C3—C4—C5 | −179.4 (11) | C44—C45—C46—N2 | −3 (2) |
C3—C4—C5—C6 | −3 (2) | C39—C40—C47—C48 | −179.2 (13) |
C4—C5—C6—C7 | 2 (2) | C41—C40—C47—C48 | 1.3 (19) |
C5—C6—C7—C8 | 0 (2) | C40—C47—C48—C43 | −2 (2) |
C5—C6—C7—C12 | −179.6 (13) | C44—C43—C48—C47 | −177.9 (15) |
C4—C3—C8—C7 | −1.0 (17) | C42—C43—C48—C47 | 1 (2) |
C2—C3—C8—C7 | −179.3 (11) | C51—N3—C49—O7 | 2 (3) |
C4—C3—C8—C9 | 179.1 (12) | C50—N3—C49—O7 | 178.1 (19) |
C2—C3—C8—C9 | 0.9 (18) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O7ii | 0.93 | 2.56 | 3.44 (2) | 157 |
C37—H37···O4i | 0.93 | 2.35 | 3.015 (11) | 128 |
C46—H46···O3 | 0.93 | 2.48 | 3.056 (13) | 120 |
C47—H47···O2iii | 0.93 | 2.45 | 3.314 (13) | 154 |
C50—H50A···O6iv | 0.96 | 2.62 | 3.40 (2) | 138 |
C18—H18···Cg1v | 0.93 | 2.90 | 3.673 (16) | 141 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) x, y, z−1; (v) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Tb2(C12H9O2)6(C12H8N2)2]·2C3H7NO |
Mr | 1935.59 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.4619 (16), 15.086 (2), 22.166 (2) |
β (°) | 103.584 (2) |
V (Å3) | 4375.6 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.67 |
Crystal size (mm) | 0.28 × 0.17 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.652, 0.825 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21422, 7389, 4674 |
Rint | 0.193 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.197, 1.07 |
No. of reflections | 7389 |
No. of parameters | 559 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0648P)2 + 17.4888P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 2.20, −2.72 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Tb1—O1i | 2.343 (5) | Tb1—O2 | 2.478 (7) |
Tb1—O3 | 2.349 (6) | Tb1—O1 | 2.539 (7) |
Tb1—O4i | 2.369 (7) | Tb1—N2 | 2.547 (9) |
Tb1—O6 | 2.433 (8) | Tb1—N1 | 2.587 (7) |
Tb1—O5 | 2.468 (8) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O7ii | 0.93 | 2.56 | 3.44 (2) | 157.4 |
C37—H37···O4i | 0.93 | 2.35 | 3.015 (11) | 127.9 |
C46—H46···O3 | 0.93 | 2.48 | 3.056 (13) | 120.4 |
C47—H47···O2iii | 0.93 | 2.45 | 3.314 (13) | 154.3 |
C50—H50A···O6iv | 0.96 | 2.62 | 3.40 (2) | 137.8 |
C18—H18···Cg1v | 0.93 | 2.90 | 3.673 (16) | 141 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) x, y, z−1; (v) −x+1, y+1/2, −z+1/2. |
As a part of our investigation of the rare earth complexes with 1-naphthylacetic acid (NAA) and 1,10-phenanthroline (phen), we have recently reported the crystal structures of two complexes [Eu(NAA)3(phen)]2.2DMF (II) (Liu et al., 2007) and [Pr(NAA)3(phen)]2 .DMF (Xia et al., 2007) We report here the crystal structure of terbium complexes with NAA and phen, (I).
In the title complex, the coordination environment of Tb atom and coordination modes of the NNA ligands coordinated to the TbIII ion are in agreement with the complex (II) (Fig. 1). The average bond lengths of between the terbium center and carboxylic oxygen atoms are 2.441 (7) Å, shorter than that (2.4725 (5) Å) of complex (II). The dihedral angles of the least-square-plane Tb2O2 and naphthyl rings are 58.20 (19)° (C3—C12 ring), 43.74 (31)° (C15—C24 ring) and 71.38 (26)° (C27—C36 ring), and the dihedral angle between Tb2O2 plane and phen ring is 82.08 (21)°.
The molecules of (I) are linked into sheets by means of C—H···π hydrogen bond (Fig. 2 and Table 2) and chains parallel to the a axis direction (Fig. 3) by C—H···O hydrogen bonds (Fig. 3 and Table 2). The action of a chains are to link adjacent [100] sheet into the three-dimensional framework structure.