metal-organic compounds
In the title compound, [Ce(C6H4NO2)3(C12H8N2)2(H2O)2]·3H2O, the CeIII atom shows a capped trigonal prismatic N4O5 coordination. The Ce—O and Ce—N bond distances are 2.390 (2)–2.517 (2) and 2.730 (3)–2.752 (3) Å, respectively.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031125/ob6450sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031125/ob6450Isup2.hkl |
CCDC reference: 262223
Computing details top
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: atomic coordinates taken from published Nd structure; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Ce(C6H4NO2)3(C12H8N2)2(H2O)2]·3H2O | Z = 2 |
Mr = 956.91 | F(000) = 970 |
Triclinic, P1 | Dx = 1.550 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.058 (1) Å | Cell parameters from 976 reflections |
b = 12.931 (1) Å | θ = 1.9–24.3° |
c = 17.879 (1) Å | µ = 1.18 mm−1 |
α = 85.011 (1)° | T = 295 K |
β = 80.643 (1)° | Prism, colorless |
γ = 84.314 (1)° | 0.22 × 0.20 × 0.18 mm |
V = 2050.8 (3) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 8380 independent reflections |
Radiation source: medium-focus sealed tube | 6984 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 26.5°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→8 |
Tmin = 0.781, Tmax = 0.816 | k = −16→16 |
11983 measured reflections | l = −22→14 |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0282P)2 + 1.2625P] where P = (Fo2 + 2Fc2)/3 |
8380 reflections | (Δ/σ)max = 0.001 |
580 parameters | Δρmax = 0.36 e Å−3 |
15 restraints | Δρmin = −0.56 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ce1 | 0.58381 (2) | 0.74130 (1) | 0.73625 (1) | 0.02673 (6) | |
O1 | 0.5459 (3) | 0.5604 (2) | 0.7092 (1) | 0.0388 (6) | |
O2 | 0.3096 (3) | 0.5193 (2) | 0.7348 (2) | 0.0609 (8) | |
O3 | 0.8139 (2) | 0.6937 (2) | 0.6559 (1) | 0.0373 (5) | |
O4 | 1.0202 (3) | 0.7583 (2) | 0.5922 (2) | 0.0548 (7) | |
O5 | 0.7354 (3) | 0.8307 (2) | 0.8134 (1) | 0.0362 (5) | |
O6 | 0.5907 (3) | 0.9614 (2) | 0.8679 (2) | 0.0567 (7) | |
O1w | 0.3072 (3) | 0.7180 (2) | 0.7563 (2) | 0.0465 (6) | |
O2w | 0.4332 (3) | 0.9091 (2) | 0.7691 (2) | 0.0450 (6) | |
O3w | 0.0380 (3) | 0.8226 (2) | 0.7319 (2) | 0.0510 (7) | |
O4w | 0.1512 (3) | 1.0004 (2) | 0.7690 (2) | 0.0618 (8) | |
O5w | 0.0195 (4) | 1.1997 (3) | 0.7424 (2) | 0.0724 (9) | |
N1 | 0.7022 (4) | 0.2514 (3) | 0.7486 (2) | 0.0615 (10) | |
N2 | 0.9336 (5) | 0.6574 (3) | 0.3911 (2) | 0.0753 (1) | |
N3 | 0.9584 (5) | 0.7778 (4) | 1.0008 (2) | 0.0801 (1) | |
N4 | 0.7482 (3) | 0.5957 (2) | 0.8178 (2) | 0.0353 (1) | |
N5 | 0.4949 (3) | 0.7020 (2) | 0.8888 (2) | 0.0350 (1) | |
N6 | 0.6866 (3) | 0.9051 (2) | 0.6396 (2) | 0.0330 (1) | |
N7 | 0.5059 (3) | 0.7741 (2) | 0.5943 (2) | 0.0370 (1) | |
C1 | 0.4473 (4) | 0.4964 (3) | 0.7256 (2) | 0.037 (1) | |
C2 | 0.5001 (4) | 0.3829 (3) | 0.7387 (2) | 0.036 (1) | |
C3 | 0.3978 (5) | 0.3097 (3) | 0.7636 (2) | 0.050 (1) | |
C4 | 0.4498 (6) | 0.2088 (3) | 0.7814 (3) | 0.069 (1) | |
C5 | 0.6007 (6) | 0.1837 (3) | 0.7742 (3) | 0.068 (1) | |
C6 | 0.6501 (4) | 0.3495 (3) | 0.7312 (2) | 0.047 (1) | |
C7 | 0.9094 (4) | 0.7081 (3) | 0.5965 (2) | 0.034 (1) | |
C8 | 0.8833 (4) | 0.6602 (3) | 0.5268 (2) | 0.036 (1) | |
C9 | 0.7822 (5) | 0.5864 (3) | 0.5300 (2) | 0.053 (1) | |
C10 | 0.7584 (6) | 0.5487 (4) | 0.4637 (3) | 0.073 (1) | |
C11 | 0.8390 (6) | 0.5849 (4) | 0.3960 (3) | 0.072 (1) | |
C12 | 0.9553 (5) | 0.6924 (4) | 0.4557 (2) | 0.057 (1) | |
C13 | 0.6940 (4) | 0.8913 (3) | 0.8668 (2) | 0.036 (1) | |
C14 | 0.7764 (4) | 0.8768 (3) | 0.9339 (2) | 0.037 (1) | |
C15 | 0.7393 (5) | 0.9420 (3) | 0.9924 (2) | 0.055 (1) | |
C16 | 0.8148 (6) | 0.9250 (4) | 1.0540 (3) | 0.073 (1) | |
C17 | 0.9200 (6) | 0.8435 (5) | 1.0553 (3) | 0.085 (2) | |
C18 | 0.8867 (5) | 0.7966 (3) | 0.9406 (2) | 0.055 (1) | |
C19 | 0.8668 (4) | 0.5403 (3) | 0.7841 (2) | 0.050 (1) | |
C20 | 0.9569 (5) | 0.4667 (3) | 0.8230 (3) | 0.060 (1) | |
C21 | 0.9236 (5) | 0.4518 (3) | 0.8992 (3) | 0.057 (1) | |
C22 | 0.8011 (4) | 0.5102 (3) | 0.9380 (2) | 0.045 (1) | |
C23 | 0.7619 (5) | 0.5008 (4) | 1.0183 (2) | 0.058 (1) | |
C24 | 0.6454 (6) | 0.5587 (4) | 1.0535 (2) | 0.059 (1) | |
C25 | 0.5517 (5) | 0.6299 (3) | 1.0121 (2) | 0.048 (1) | |
C26 | 0.4267 (5) | 0.6892 (4) | 1.0460 (2) | 0.062 (1) | |
C27 | 0.3383 (5) | 0.7508 (4) | 1.0036 (2) | 0.061 (1) | |
C28 | 0.3756 (4) | 0.7539 (3) | 0.9244 (2) | 0.049 (1) | |
C29 | 0.5840 (4) | 0.6397 (3) | 0.9320 (2) | 0.036 (1) | |
C30 | 0.7137 (4) | 0.5813 (3) | 0.8946 (2) | 0.034 (1) | |
C31 | 0.7684 (4) | 0.9731 (3) | 0.6609 (2) | 0.039 (1) | |
C32 | 0.8442 (4) | 1.0466 (3) | 0.6114 (2) | 0.046 (1) | |
C33 | 0.8352 (4) | 1.0491 (3) | 0.5361 (2) | 0.047 (1) | |
C34 | 0.7497 (4) | 0.9792 (3) | 0.5102 (2) | 0.037 (1) | |
C35 | 0.7345 (5) | 0.9786 (3) | 0.4321 (2) | 0.049 (1) | |
C36 | 0.6475 (5) | 0.9130 (3) | 0.4098 (2) | 0.049 (1) | |
C37 | 0.5658 (4) | 0.8417 (3) | 0.4632 (2) | 0.041 (1) | |
C38 | 0.4681 (5) | 0.7770 (3) | 0.4425 (2) | 0.051 (1) | |
C39 | 0.3886 (5) | 0.7160 (3) | 0.4969 (2) | 0.057 (1) | |
C40 | 0.4117 (5) | 0.7157 (3) | 0.5724 (2) | 0.050 (1) | |
C41 | 0.5810 (4) | 0.8389 (3) | 0.5405 (2) | 0.033 (1) | |
C42 | 0.6755 (4) | 0.9083 (2) | 0.5643 (2) | 0.032 (1) | |
H1w1 | 0.294 (4) | 0.656 (1) | 0.748 (2) | 0.056* | |
H1w2 | 0.225 (2) | 0.756 (2) | 0.756 (2) | 0.056* | |
H2w1 | 0.471 (3) | 0.936 (3) | 0.803 (2) | 0.054* | |
H2w2 | 0.345 (2) | 0.939 (3) | 0.768 (2) | 0.054* | |
H3w1 | 0.038 (4) | 0.808 (3) | 0.687 (1) | 0.061* | |
H3w2 | −0.048 (2) | 0.818 (3) | 0.758 (2) | 0.061* | |
H4w1 | 0.101 (4) | 0.951 (2) | 0.764 (3) | 0.074* | |
H4w2 | 0.102 (4) | 1.058 (1) | 0.762 (3) | 0.074* | |
H5w1 | −0.074 (2) | 1.213 (4) | 0.756 (2) | 0.087* | |
H5w2 | 0.050 (4) | 1.236 (3) | 0.702 (2) | 0.087* | |
H3 | 0.2952 | 0.3287 | 0.7682 | 0.060* | |
H4 | 0.3831 | 0.1584 | 0.7981 | 0.083* | |
H5 | 0.6348 | 0.1156 | 0.7879 | 0.082* | |
H6 | 0.7193 | 0.3977 | 0.7130 | 0.056* | |
H9 | 0.7306 | 0.5623 | 0.5766 | 0.064* | |
H10 | 0.6893 | 0.4999 | 0.4645 | 0.088* | |
H11 | 0.8261 | 0.5568 | 0.3516 | 0.087* | |
H12 | 1.0239 | 0.7421 | 0.4530 | 0.069* | |
H15 | 0.6647 | 0.9965 | 0.9904 | 0.066* | |
H16 | 0.7937 | 0.9686 | 1.0938 | 0.088* | |
H17 | 0.9693 | 0.8325 | 1.0975 | 0.102* | |
H18 | 0.9128 | 0.7531 | 0.9009 | 0.066* | |
H19 | 0.8922 | 0.5507 | 0.7317 | 0.060* | |
H20 | 1.0384 | 0.4287 | 0.7966 | 0.072* | |
H21 | 0.9816 | 0.4030 | 0.9259 | 0.069* | |
H23 | 0.8183 | 0.4535 | 1.0469 | 0.069* | |
H24 | 0.6246 | 0.5527 | 1.1063 | 0.071* | |
H26 | 0.4036 | 0.6865 | 1.0987 | 0.075* | |
H27 | 0.2543 | 0.7903 | 1.0264 | 0.073* | |
H28 | 0.3126 | 0.7949 | 0.8953 | 0.058* | |
H31 | 0.7759 | 0.9718 | 0.7123 | 0.047* | |
H32 | 0.8998 | 1.0930 | 0.6295 | 0.056* | |
H33 | 0.8855 | 1.0971 | 0.5020 | 0.056* | |
H35 | 0.7857 | 1.0242 | 0.3962 | 0.059* | |
H36 | 0.6397 | 0.9137 | 0.3585 | 0.059* | |
H38 | 0.4572 | 0.7755 | 0.3917 | 0.062* | |
H39 | 0.3194 | 0.6747 | 0.4841 | 0.068* | |
H40 | 0.3579 | 0.6724 | 0.6090 | 0.060* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ce1 | 0.0263 (1) | 0.0256 (1) | 0.0281 (1) | −0.0022 (1) | −0.0057 (1) | 0.0012 (1) |
O1 | 0.036 (1) | 0.032 (1) | 0.049 (2) | −0.008 (1) | −0.004 (1) | 0.000 (1) |
O2 | 0.037 (2) | 0.040 (2) | 0.106 (2) | −0.006 (1) | −0.009 (2) | −0.007 (2) |
O3 | 0.036 (1) | 0.039 (1) | 0.034 (1) | −0.003 (1) | 0.003 (1) | 0.002 (1) |
O4 | 0.043 (2) | 0.079 (2) | 0.045 (2) | −0.027 (2) | 0.000 (1) | −0.006 (1) |
O5 | 0.039 (1) | 0.037 (1) | 0.035 (1) | −0.006 (1) | −0.011 (1) | −0.003 (1) |
O6 | 0.070 (2) | 0.042 (2) | 0.064 (2) | 0.017 (1) | −0.034 (2) | −0.014 (1) |
O1w | 0.032 (1) | 0.039 (1) | 0.071 (2) | 0.000 (1) | −0.012 (1) | −0.010 (1) |
O2w | 0.038 (1) | 0.039 (2) | 0.061 (2) | 0.006 (1) | −0.017 (1) | −0.013 (1) |
O3w | 0.038 (2) | 0.059 (2) | 0.059 (2) | −0.002 (1) | −0.015 (1) | −0.012 (2) |
O4w | 0.050 (2) | 0.061 (2) | 0.081 (2) | 0.009 (2) | −0.031 (2) | −0.018 (2) |
O5w | 0.071 (2) | 0.072 (2) | 0.067 (2) | 0.011 (2) | −0.009 (2) | 0.010 (2) |
N1 | 0.070 (2) | 0.043 (2) | 0.066 (2) | 0.010 (2) | −0.005 (2) | −0.001 (2) |
N2 | 0.096 (3) | 0.097 (3) | 0.036 (2) | −0.037 (3) | −0.004 (2) | −0.008 (2) |
N3 | 0.082 (3) | 0.098 (3) | 0.064 (3) | 0.020 (2) | −0.042 (2) | −0.003 (2) |
N4 | 0.034 (2) | 0.036 (2) | 0.034 (2) | 0.002 (1) | −0.007 (1) | 0.002 (1) |
N5 | 0.032 (2) | 0.037 (2) | 0.034 (2) | −0.005 (1) | 0.000 (1) | 0.001 (1) |
N6 | 0.039 (2) | 0.027 (1) | 0.033 (2) | −0.003 (1) | −0.006 (1) | 0.002 (1) |
N7 | 0.039 (2) | 0.035 (2) | 0.039 (2) | −0.007 (1) | −0.013 (1) | 0.003 (1) |
C1 | 0.037 (2) | 0.037 (2) | 0.036 (2) | −0.006 (2) | −0.004 (2) | −0.004 (2) |
C2 | 0.045 (2) | 0.031 (2) | 0.031 (2) | −0.006 (2) | −0.002 (2) | −0.004 (1) |
C3 | 0.056 (2) | 0.041 (2) | 0.052 (2) | −0.014 (2) | 0.007 (2) | −0.008 (2) |
C4 | 0.097 (4) | 0.036 (2) | 0.067 (3) | −0.017 (2) | 0.018 (3) | −0.003 (2) |
C5 | 0.103 (4) | 0.030 (2) | 0.063 (3) | 0.003 (2) | 0.006 (3) | 0.003 (2) |
C6 | 0.053 (2) | 0.033 (2) | 0.053 (2) | −0.006 (2) | −0.003 (2) | 0.001 (2) |
C7 | 0.033 (2) | 0.033 (2) | 0.035 (2) | 0.001 (2) | −0.005 (2) | 0.002 (2) |
C8 | 0.037 (2) | 0.034 (2) | 0.035 (2) | −0.003 (2) | −0.003 (2) | 0.002 (2) |
C9 | 0.068 (3) | 0.046 (2) | 0.045 (2) | −0.019 (2) | −0.002 (2) | 0.000 (2) |
C10 | 0.098 (4) | 0.060 (3) | 0.069 (3) | −0.036 (3) | −0.017 (3) | −0.010 (2) |
C11 | 0.103 (4) | 0.075 (3) | 0.045 (3) | −0.021 (3) | −0.018 (3) | −0.013 (2) |
C12 | 0.061 (3) | 0.072 (3) | 0.041 (2) | −0.028 (2) | −0.001 (2) | −0.003 (2) |
C13 | 0.041 (2) | 0.031 (2) | 0.039 (2) | −0.010 (2) | −0.013 (2) | 0.004 (2) |
C14 | 0.040 (2) | 0.037 (2) | 0.035 (2) | −0.006 (2) | −0.011 (2) | −0.001 (2) |
C15 | 0.060 (3) | 0.060 (3) | 0.046 (2) | 0.002 (2) | −0.013 (2) | −0.010 (2) |
C16 | 0.079 (3) | 0.101 (4) | 0.045 (3) | 0.001 (3) | −0.020 (2) | −0.025 (3) |
C17 | 0.081 (4) | 0.131 (5) | 0.047 (3) | 0.005 (4) | −0.034 (3) | −0.005 (3) |
C18 | 0.058 (3) | 0.063 (3) | 0.047 (2) | 0.008 (2) | −0.024 (2) | −0.004 (2) |
C19 | 0.047 (2) | 0.052 (2) | 0.045 (2) | 0.009 (2) | −0.004 (2) | 0.005 (2) |
C20 | 0.049 (2) | 0.057 (3) | 0.067 (3) | 0.017 (2) | −0.009 (2) | 0.006 (2) |
C21 | 0.049 (2) | 0.053 (3) | 0.070 (3) | 0.006 (2) | −0.026 (2) | 0.015 (2) |
C22 | 0.052 (2) | 0.044 (2) | 0.044 (2) | −0.014 (2) | −0.023 (2) | 0.013 (2) |
C23 | 0.070 (3) | 0.063 (3) | 0.046 (2) | −0.016 (2) | −0.030 (2) | 0.015 (2) |
C24 | 0.084 (3) | 0.071 (3) | 0.028 (2) | −0.022 (3) | −0.021 (2) | 0.009 (2) |
C25 | 0.059 (3) | 0.052 (2) | 0.034 (2) | −0.021 (2) | −0.004 (2) | −0.001 (2) |
C26 | 0.078 (3) | 0.076 (3) | 0.033 (2) | −0.022 (3) | 0.004 (2) | −0.012 (2) |
C27 | 0.056 (3) | 0.067 (3) | 0.053 (3) | −0.007 (2) | 0.017 (2) | −0.019 (2) |
C28 | 0.043 (2) | 0.049 (2) | 0.049 (2) | −0.003 (2) | 0.006 (2) | −0.003 (2) |
C29 | 0.042 (2) | 0.036 (2) | 0.032 (2) | −0.013 (2) | −0.005 (2) | 0.000 (2) |
C30 | 0.039 (2) | 0.033 (2) | 0.034 (2) | −0.011 (2) | −0.013 (2) | 0.005 (2) |
C31 | 0.049 (2) | 0.032 (2) | 0.037 (2) | −0.005 (2) | −0.007 (2) | 0.000 (2) |
C32 | 0.053 (2) | 0.037 (2) | 0.050 (2) | −0.012 (2) | −0.008 (2) | 0.001 (2) |
C33 | 0.047 (2) | 0.037 (2) | 0.052 (2) | −0.011 (2) | 0.000 (2) | 0.010 (2) |
C34 | 0.036 (2) | 0.034 (2) | 0.037 (2) | 0.004 (2) | −0.001 (2) | 0.004 (2) |
C35 | 0.054 (2) | 0.048 (2) | 0.040 (2) | −0.001 (2) | 0.002 (2) | 0.011 (2) |
C36 | 0.062 (3) | 0.056 (3) | 0.026 (2) | 0.002 (2) | −0.005 (2) | 0.005 (2) |
C37 | 0.044 (2) | 0.044 (2) | 0.033 (2) | 0.003 (2) | −0.010 (2) | 0.001 (2) |
C38 | 0.062 (3) | 0.057 (3) | 0.039 (2) | −0.001 (2) | −0.023 (2) | 0.000 (2) |
C39 | 0.064 (3) | 0.057 (3) | 0.059 (3) | −0.017 (2) | −0.033 (2) | 0.000 (2) |
C40 | 0.054 (2) | 0.051 (2) | 0.048 (2) | −0.015 (2) | −0.020 (2) | 0.009 (2) |
C41 | 0.035 (2) | 0.029 (2) | 0.035 (2) | 0.004 (1) | −0.008 (2) | 0.002 (1) |
C42 | 0.034 (2) | 0.028 (2) | 0.032 (2) | 0.004 (1) | −0.005 (1) | 0.003 (1) |
Geometric parameters (Å, º) top
Ce1—O1 | 2.497 (2) | C26—C27 | 1.348 (6) |
Ce1—O3 | 2.390 (2) | C27—C28 | 1.399 (6) |
Ce1—O5 | 2.517 (2) | C29—C30 | 1.432 (5) |
Ce1—O1w | 2.517 (2) | C31—C32 | 1.395 (5) |
Ce1—O2w | 2.508 (2) | C32—C33 | 1.359 (5) |
Ce1—N4 | 2.750 (3) | C33—C34 | 1.400 (5) |
Ce1—N5 | 2.733 (3) | C34—C42 | 1.409 (4) |
Ce1—N6 | 2.752 (3) | C34—C35 | 1.425 (5) |
Ce1—N7 | 2.730 (3) | C35—C36 | 1.339 (5) |
O1—C1 | 1.260 (4) | C36—C37 | 1.435 (5) |
O2—C1 | 1.240 (4) | C37—C38 | 1.390 (5) |
O3—C7 | 1.269 (4) | C37—C41 | 1.408 (5) |
O4—C7 | 1.237 (4) | C38—C39 | 1.355 (6) |
O5—C13 | 1.273 (4) | C39—C40 | 1.400 (5) |
O6—C13 | 1.236 (4) | C41—C42 | 1.434 (5) |
N1—C5 | 1.332 (6) | O1w—H1w1 | 0.85 (1) |
N1—C6 | 1.337 (5) | O1w—H1w2 | 0.85 (1) |
N2—C11 | 1.320 (6) | O2w—H2w1 | 0.86 (1) |
N2—C12 | 1.328 (5) | O2w—H2w2 | 0.85 (1) |
N3—C17 | 1.330 (7) | O3w—H3w1 | 0.84 (1) |
N3—C18 | 1.338 (5) | O3w—H3w2 | 0.84 (1) |
N4—C19 | 1.320 (4) | O4w—H4w1 | 0.84 (1) |
N4—C30 | 1.358 (4) | O4w—H4w2 | 0.84 (1) |
N5—C28 | 1.315 (4) | O5w—H5w1 | 0.85 (1) |
N5—C29 | 1.365 (4) | O5w—H5w2 | 0.84 (1) |
N6—C31 | 1.321 (4) | C3—H3 | 0.93 |
N6—C42 | 1.363 (4) | C4—H4 | 0.93 |
N7—C40 | 1.318 (4) | C5—H5 | 0.93 |
N7—C41 | 1.361 (4) | C6—H6 | 0.93 |
C1—C2 | 1.508 (5) | C9—H9 | 0.93 |
C2—C6 | 1.373 (5) | C10—H10 | 0.93 |
C2—C3 | 1.386 (5) | C11—H11 | 0.93 |
C3—C4 | 1.370 (6) | C12—H12 | 0.93 |
C4—C5 | 1.361 (7) | C15—H15 | 0.93 |
C7—C8 | 1.500 (5) | C16—H16 | 0.93 |
C8—C9 | 1.378 (5) | C17—H17 | 0.93 |
C8—C12 | 1.380 (5) | C18—H18 | 0.93 |
C9—C10 | 1.377 (6) | C19—H19 | 0.93 |
C10—C11 | 1.377 (6) | C20—H20 | 0.93 |
C13—C14 | 1.502 (5) | C21—H21 | 0.93 |
C14—C18 | 1.378 (5) | C23—H23 | 0.93 |
C14—C15 | 1.379 (5) | C24—H24 | 0.93 |
C15—C16 | 1.379 (6) | C26—H26 | 0.93 |
C16—C17 | 1.350 (7) | C27—H27 | 0.93 |
C19—C20 | 1.404 (5) | C28—H28 | 0.93 |
C20—C21 | 1.348 (6) | C31—H31 | 0.93 |
C21—C22 | 1.398 (6) | C32—H32 | 0.93 |
C22—C30 | 1.416 (5) | C33—H33 | 0.93 |
C22—C23 | 1.420 (6) | C35—H35 | 0.93 |
C23—C24 | 1.334 (6) | C36—H36 | 0.93 |
C24—C25 | 1.430 (6) | C38—H38 | 0.93 |
C25—C26 | 1.387 (6) | C39—H39 | 0.93 |
C25—C29 | 1.413 (5) | C40—H40 | 0.93 |
O1—Ce1—O3 | 78.5 (1) | C27—C26—C25 | 120.9 (4) |
O1—Ce1—O5 | 138.7 (1) | C26—C27—C28 | 118.6 (4) |
O1—Ce1—O1w | 70.5 (1) | N5—C28—C27 | 123.6 (4) |
O1—Ce1—O2w | 139.8 (1) | N5—C29—C25 | 122.2 (3) |
O1—Ce1—N4 | 68.8 (1) | N5—C29—C30 | 118.8 (3) |
O1—Ce1—N5 | 92.3 (1) | C25—C29—C30 | 119.0 (3) |
O1—Ce1—N6 | 130.3 (1) | N4—C30—C22 | 121.9 (3) |
O1—Ce1—N7 | 78.8 (1) | N4—C30—C29 | 118.4 (3) |
O3—Ce1—O5 | 87.6 (1) | C22—C30—C29 | 119.7 (3) |
O3—Ce1—O1w | 141.9 (1) | N6—C31—C32 | 124.2 (3) |
O3—Ce1—O2w | 135.5 (1) | C33—C32—C31 | 118.7 (4) |
O3—Ce1—N4 | 72.4 (1) | C32—C33—C34 | 119.7 (3) |
O3—Ce1—N5 | 131.3 (1) | C33—C34—C42 | 117.8 (3) |
O3—Ce1—N6 | 67.4 (1) | C33—C34—C35 | 122.4 (3) |
O3—Ce1—N7 | 77.3 (1) | C42—C34—C35 | 119.7 (3) |
O5—Ce1—O1w | 130.4 (1) | C36—C35—C34 | 120.7 (3) |
O5—Ce1—O2w | 74.1 (1) | C35—C36—C37 | 121.5 (3) |
O5—Ce1—N4 | 69.9 (1) | C38—C37—C41 | 118.0 (3) |
O5—Ce1—N5 | 68.3 (1) | C38—C37—C36 | 122.9 (3) |
O5—Ce1—N6 | 76.3 (1) | C41—C37—C36 | 119.1 (3) |
O5—Ce1—N7 | 135.9 (1) | C39—C38—C37 | 119.4 (4) |
O1w—Ce1—O2w | 69.5 (1) | C38—C39—C40 | 119.5 (4) |
O1w—Ce1—N4 | 114.1 (1) | N7—C40—C39 | 123.1 (4) |
O1w—Ce1—N5 | 72.6 (1) | N7—C41—C37 | 122.3 (3) |
O1w—Ce1—N6 | 118.2 (1) | N7—C41—C42 | 118.3 (3) |
O1w—Ce1—N7 | 75.5 (1) | C37—C41—C42 | 119.4 (3) |
O2w—Ce1—N4 | 132.8 (1) | N6—C42—C34 | 122.2 (3) |
O2w—Ce1—N5 | 79.1 (1) | N6—C42—C41 | 118.3 (3) |
O2w—Ce1—N6 | 69.0 (1) | C34—C42—C41 | 119.4 (3) |
O2w—Ce1—N7 | 88.2 (1) | Ce1—O1w—H1w1 | 110 (2) |
N4—Ce1—N5 | 59.9 (1) | Ce1—O1w—H1w2 | 138 (2) |
N4—Ce1—N6 | 127.7 (1) | H1w1—O1w—H1w2 | 109 (2) |
N4—Ce1—N7 | 139.0 (1) | Ce1—O2w—H2w1 | 109 (2) |
N5—Ce1—N6 | 137.4 (1) | Ce1—O2w—H2w2 | 139 (2) |
N5—Ce1—N7 | 148.1 (1) | H2w1—O2w—H2w2 | 108 (2) |
N6—Ce1—N7 | 59.6 (1) | H3w1—O3w—H3w2 | 111 (2) |
C1—O1—Ce1 | 138.7 (2) | H4w1—O4w—H4w2 | 111 (2) |
C7—O3—Ce1 | 151.8 (2) | H5w1—O5w—H5w2 | 111 (2) |
C13—O5—Ce1 | 130.7 (2) | C4—C3—H3 | 120.4 |
C5—N1—C6 | 117.0 (4) | C2—C3—H3 | 120.4 |
C11—N2—C12 | 117.1 (4) | C5—C4—H4 | 120.6 |
C17—N3—C18 | 116.0 (4) | C3—C4—H4 | 120.6 |
C19—N4—C30 | 117.6 (3) | N1—C5—H5 | 118.2 |
C19—N4—Ce1 | 121.2 (2) | C4—C5—H5 | 118.2 |
C30—N4—Ce1 | 121.1 (2) | N1—C6—H6 | 118.2 |
C28—N5—C29 | 117.7 (3) | C2—C6—H6 | 118.2 |
C28—N5—Ce1 | 120.7 (2) | C10—C9—H9 | 120.3 |
C29—N5—Ce1 | 121.0 (2) | C8—C9—H9 | 120.3 |
C31—N6—C42 | 117.4 (3) | C11—C10—H10 | 120.7 |
C31—N6—Ce1 | 121.8 (2) | C9—C10—H10 | 120.7 |
C42—N6—Ce1 | 120.0 (2) | N2—C11—H11 | 118.4 |
C40—N7—C41 | 117.7 (3) | C10—C11—H11 | 118.4 |
C40—N7—Ce1 | 120.7 (2) | N2—C12—H12 | 117.7 |
C41—N7—Ce1 | 120.7 (2) | C8—C12—H12 | 117.7 |
O2—C1—O1 | 125.4 (3) | C16—C15—H15 | 120.5 |
O2—C1—C2 | 116.9 (3) | C14—C15—H15 | 120.5 |
O1—C1—C2 | 117.6 (3) | C17—C16—H16 | 120.7 |
C6—C2—C3 | 117.7 (3) | C15—C16—H16 | 120.7 |
C6—C2—C1 | 121.6 (3) | N3—C17—H17 | 117.6 |
C3—C2—C1 | 120.6 (3) | C16—C17—H17 | 117.6 |
C4—C3—C2 | 119.2 (4) | N3—C18—H18 | 118.0 |
C5—C4—C3 | 118.9 (4) | C14—C18—H18 | 118.0 |
N1—C5—C4 | 123.6 (4) | N4—C19—H19 | 118.1 |
N1—C6—C2 | 123.7 (4) | C20—C19—H19 | 118.1 |
O4—C7—O3 | 124.9 (3) | C21—C20—H20 | 120.5 |
O4—C7—C8 | 118.6 (3) | C19—C20—H20 | 120.5 |
O3—C7—C8 | 116.5 (3) | C20—C21—H21 | 120.2 |
C9—C8—C12 | 117.1 (4) | C22—C21—H21 | 120.2 |
C9—C8—C7 | 122.0 (3) | C24—C23—H23 | 119.5 |
C12—C8—C7 | 120.8 (3) | C22—C23—H23 | 119.5 |
C10—C9—C8 | 119.3 (4) | C23—C24—H24 | 119.1 |
C11—C10—C9 | 118.6 (4) | C25—C24—H24 | 119.1 |
N2—C11—C10 | 123.3 (4) | C27—C26—H26 | 119.6 |
N2—C12—C8 | 124.6 (4) | C25—C26—H26 | 119.6 |
O6—C13—O5 | 125.1 (3) | C26—C27—H27 | 120.7 |
O6—C13—C14 | 117.1 (3) | C28—C27—H27 | 120.7 |
O5—C13—C14 | 117.8 (3) | N5—C28—H28 | 118.2 |
C18—C14—C15 | 117.8 (4) | C27—C28—H28 | 118.2 |
C18—C14—C13 | 121.7 (3) | N6—C31—H31 | 117.9 |
C15—C14—C13 | 120.4 (3) | C32—C31—H31 | 117.9 |
C16—C15—C14 | 118.9 (4) | C33—C32—H32 | 120.7 |
C17—C16—C15 | 118.5 (5) | C31—C32—H32 | 120.7 |
N3—C17—C16 | 124.8 (4) | C32—C33—H33 | 120.1 |
N3—C18—C14 | 123.9 (4) | C34—C33—H33 | 120.1 |
N4—C19—C20 | 123.7 (4) | C36—C35—H35 | 119.6 |
C21—C20—C19 | 119.1 (4) | C34—C35—H35 | 119.6 |
C20—C21—C22 | 119.5 (4) | C35—C36—H36 | 119.2 |
C21—C22—C30 | 118.1 (3) | C37—C36—H36 | 119.2 |
C21—C22—C23 | 122.7 (4) | C39—C38—H38 | 120.3 |
C30—C22—C23 | 119.3 (4) | C37—C38—H38 | 120.3 |
C24—C23—C22 | 121.1 (4) | C38—C39—H39 | 120.3 |
C23—C24—C25 | 121.7 (4) | C40—C39—H39 | 120.3 |
C26—C25—C29 | 117.1 (4) | N7—C40—H40 | 118.4 |
C26—C25—C24 | 123.8 (4) | C39—C40—H40 | 118.4 |
C29—C25—C24 | 119.1 (4) | ||
O3—Ce1—O1—C1 | 180.0 (3) | Ce1—O3—C7—O4 | 92.3 (5) |
O2W—Ce1—O1—C1 | −27.4 (4) | Ce1—O3—C7—C8 | −87.4 (5) |
O5—Ce1—O1—C1 | 107.2 (3) | O4—C7—C8—C9 | 166.6 (4) |
O1W—Ce1—O1—C1 | −22.4 (3) | O3—C7—C8—C9 | −13.7 (5) |
N7—Ce1—O1—C1 | −100.9 (3) | O4—C7—C8—C12 | −16.6 (5) |
N5—Ce1—O1—C1 | 48.3 (3) | O3—C7—C8—C12 | 163.1 (3) |
N4—Ce1—O1—C1 | 104.6 (3) | C12—C8—C9—C10 | 0.2 (6) |
N6—Ce1—O1—C1 | −133.3 (3) | C7—C8—C9—C10 | 177.2 (4) |
O1—Ce1—O3—C7 | 122.1 (5) | C8—C9—C10—C11 | 1.2 (7) |
O2W—Ce1—O3—C7 | −32.8 (5) | C12—N2—C11—C10 | 3.2 (8) |
O5—Ce1—O3—C7 | −97.0 (5) | C9—C10—C11—N2 | −3.0 (8) |
O1W—Ce1—O3—C7 | 86.5 (5) | C11—N2—C12—C8 | −1.8 (8) |
N7—Ce1—O3—C7 | 41.2 (5) | C9—C8—C12—N2 | 0.1 (7) |
N5—Ce1—O3—C7 | −155.0 (5) | C7—C8—C12—N2 | −176.9 (4) |
N4—Ce1—O3—C7 | −166.7 (5) | Ce1—O5—C13—O6 | −41.2 (5) |
N6—Ce1—O3—C7 | −20.9 (5) | Ce1—O5—C13—C14 | 138.8 (2) |
O3—Ce1—O5—C13 | 170.4 (3) | O6—C13—C14—C18 | 175.7 (4) |
O1—Ce1—O5—C13 | −120.1 (3) | O5—C13—C14—C18 | −4.3 (5) |
O2W—Ce1—O5—C13 | 31.4 (3) | O6—C13—C14—C15 | −1.9 (5) |
O1W—Ce1—O5—C13 | −12.5 (3) | O5—C13—C14—C15 | 178.1 (3) |
N7—Ce1—O5—C13 | 101.4 (3) | C18—C14—C15—C16 | 0.8 (6) |
N5—Ce1—O5—C13 | −52.9 (3) | C13—C14—C15—C16 | 178.5 (4) |
N4—Ce1—O5—C13 | −117.5 (3) | C14—C15—C16—C17 | −1.4 (7) |
N6—Ce1—O5—C13 | 103.0 (3) | C18—N3—C17—C16 | 0.8 (9) |
O3—Ce1—N4—C19 | −13.2 (3) | C15—C16—C17—N3 | 0.6 (9) |
O1—Ce1—N4—C19 | 71.0 (3) | C17—N3—C18—C14 | −1.6 (7) |
O2W—Ce1—N4—C19 | −149.8 (3) | C15—C14—C18—N3 | 0.8 (7) |
O5—Ce1—N4—C19 | −107.2 (3) | C13—C14—C18—N3 | −176.9 (4) |
O1W—Ce1—N4—C19 | 126.5 (3) | C30—N4—C19—C20 | 1.1 (6) |
N7—Ce1—N4—C19 | 30.9 (3) | Ce1—N4—C19—C20 | 178.5 (3) |
N5—Ce1—N4—C19 | 176.9 (3) | N4—C19—C20—C21 | −1.1 (7) |
N6—Ce1—N4—C19 | −54.2 (3) | C19—C20—C21—C22 | −0.4 (7) |
O3—Ce1—N4—C30 | 164.1 (3) | C20—C21—C22—C30 | 1.8 (6) |
O1—Ce1—N4—C30 | −111.7 (3) | C20—C21—C22—C23 | −178.2 (4) |
O2W—Ce1—N4—C30 | 27.6 (3) | C21—C22—C23—C24 | 179.2 (4) |
O5—Ce1—N4—C30 | 70.2 (2) | C30—C22—C23—C24 | −0.8 (6) |
O1W—Ce1—N4—C30 | −56.2 (3) | C22—C23—C24—C25 | 2.3 (7) |
N7—Ce1—N4—C30 | −151.7 (2) | C23—C24—C25—C26 | 177.9 (4) |
N5—Ce1—N4—C30 | −5.7 (2) | C23—C24—C25—C29 | −0.5 (6) |
N6—Ce1—N4—C30 | 123.2 (2) | C29—C25—C26—C27 | 2.0 (6) |
O3—Ce1—N5—C28 | 165.5 (3) | C24—C25—C26—C27 | −176.4 (4) |
O1—Ce1—N5—C28 | −117.9 (3) | C25—C26—C27—C28 | −0.2 (7) |
O2W—Ce1—N5—C28 | 22.6 (3) | C29—N5—C28—C27 | 2.0 (6) |
O5—Ce1—N5—C28 | 99.7 (3) | Ce1—N5—C28—C27 | −168.8 (3) |
O1W—Ce1—N5—C28 | −49.1 (3) | C26—C27—C28—N5 | −1.9 (7) |
N7—Ce1—N5—C28 | −45.5 (3) | C28—N5—C29—C25 | 0.0 (5) |
N4—Ce1—N5—C28 | 178.4 (3) | Ce1—N5—C29—C25 | 170.7 (3) |
N6—Ce1—N5—C28 | 63.9 (3) | C28—N5—C29—C30 | 179.3 (3) |
O3—Ce1—N5—C29 | −5.0 (3) | Ce1—N5—C29—C30 | −10.0 (4) |
O1—Ce1—N5—C29 | 71.7 (2) | C26—C25—C29—N5 | −1.9 (5) |
O2W—Ce1—N5—C29 | −147.8 (3) | C24—C25—C29—N5 | 176.6 (3) |
O5—Ce1—N5—C29 | −70.7 (2) | C26—C25—C29—C30 | 178.8 (3) |
O1W—Ce1—N5—C29 | 140.4 (3) | C24—C25—C29—C30 | −2.7 (5) |
N7—Ce1—N5—C29 | 144.0 (2) | C19—N4—C30—C22 | 0.4 (5) |
N4—Ce1—N5—C29 | 8.0 (2) | Ce1—N4—C30—C22 | −177.0 (2) |
N6—Ce1—N5—C29 | −106.5 (2) | C19—N4—C30—C29 | −179.1 (3) |
O3—Ce1—N6—C31 | −95.1 (3) | Ce1—N4—C30—C29 | 3.5 (4) |
O1—Ce1—N6—C31 | −145.7 (2) | C21—C22—C30—N4 | −1.8 (5) |
O2W—Ce1—N6—C31 | 76.0 (3) | C23—C22—C30—N4 | 178.1 (3) |
O5—Ce1—N6—C31 | −2.0 (2) | C21—C22—C30—C29 | 177.6 (3) |
O1W—Ce1—N6—C31 | 126.7 (3) | C23—C22—C30—C29 | −2.4 (5) |
N7—Ce1—N6—C31 | 176.7 (3) | N5—C29—C30—N4 | 4.3 (5) |
N5—Ce1—N6—C31 | 32.0 (3) | C25—C29—C30—N4 | −176.4 (3) |
N4—Ce1—N6—C31 | −52.6 (3) | N5—C29—C30—C22 | −175.2 (3) |
O3—Ce1—N6—C42 | 73.9 (2) | C25—C29—C30—C22 | 4.1 (5) |
O1—Ce1—N6—C42 | 23.4 (3) | C42—N6—C31—C32 | −0.5 (5) |
O2W—Ce1—N6—C42 | −115.0 (2) | Ce1—N6—C31—C32 | 168.8 (3) |
O5—Ce1—N6—C42 | 167.0 (2) | N6—C31—C32—C33 | −0.4 (6) |
O1W—Ce1—N6—C42 | −64.2 (2) | C31—C32—C33—C34 | 0.6 (6) |
N7—Ce1—N6—C42 | −14.3 (2) | C32—C33—C34—C42 | 0.1 (5) |
N5—Ce1—N6—C42 | −159.0 (2) | C32—C33—C34—C35 | 179.3 (4) |
N4—Ce1—N6—C42 | 116.5 (2) | C33—C34—C35—C36 | −177.6 (4) |
O3—Ce1—N7—C40 | 112.9 (3) | C42—C34—C35—C36 | 1.6 (6) |
O1—Ce1—N7—C40 | 32.4 (3) | C34—C35—C36—C37 | 0.3 (6) |
O2W—Ce1—N7—C40 | −109.4 (3) | C35—C36—C37—C38 | 176.3 (4) |
O5—Ce1—N7—C40 | −174.2 (3) | C35—C36—C37—C41 | −1.7 (6) |
O1W—Ce1—N7—C40 | −40.1 (3) | C41—C37—C38—C39 | 1.7 (6) |
N5—Ce1—N7—C40 | −43.7 (4) | C36—C37—C38—C39 | −176.3 (4) |
N4—Ce1—N7—C40 | 70.1 (3) | C37—C38—C39—C40 | −3.0 (6) |
N6—Ce1—N7—C40 | −176.0 (3) | C41—N7—C40—C39 | 1.5 (6) |
O3—Ce1—N7—C41 | −56.3 (2) | Ce1—N7—C40—C39 | −168.0 (3) |
O1—Ce1—N7—C41 | −136.9 (3) | C38—C39—C40—N7 | 1.4 (7) |
O2W—Ce1—N7—C41 | 81.3 (2) | C40—N7—C41—C37 | −2.9 (5) |
O5—Ce1—N7—C41 | 16.6 (3) | Ce1—N7—C41—C37 | 166.7 (3) |
O1W—Ce1—N7—C41 | 150.6 (3) | C40—N7—C41—C42 | 175.5 (3) |
N5—Ce1—N7—C41 | 147.0 (2) | Ce1—N7—C41—C42 | −14.9 (4) |
N4—Ce1—N7—C41 | −99.2 (3) | C38—C37—C41—N7 | 1.3 (5) |
N6—Ce1—N7—C41 | 14.8 (2) | C36—C37—C41—N7 | 179.3 (3) |
Ce1—O1—C1—O2 | 34.6 (6) | C38—C37—C41—C42 | −177.0 (3) |
Ce1—O1—C1—C2 | −142.5 (3) | C36—C37—C41—C42 | 1.0 (5) |
O2—C1—C2—C6 | −179.0 (4) | C31—N6—C42—C34 | 1.3 (5) |
O1—C1—C2—C6 | −1.7 (5) | Ce1—N6—C42—C34 | −168.2 (2) |
O2—C1—C2—C3 | −3.2 (5) | C31—N6—C42—C41 | −176.8 (3) |
O1—C1—C2—C3 | 174.1 (3) | Ce1—N6—C42—C41 | 13.7 (4) |
C6—C2—C3—C4 | 1.7 (6) | C33—C34—C42—N6 | −1.1 (5) |
C1—C2—C3—C4 | −174.3 (4) | C35—C34—C42—N6 | 179.7 (3) |
C2—C3—C4—C5 | 0.2 (7) | C33—C34—C42—C41 | 177.0 (3) |
C6—N1—C5—C4 | 1.7 (7) | C35—C34—C42—C41 | −2.3 (5) |
C3—C4—C5—N1 | −1.9 (8) | N7—C41—C42—N6 | 0.7 (4) |
C5—N1—C6—C2 | 0.3 (6) | C37—C41—C42—N6 | 179.1 (3) |
C3—C2—C6—N1 | −2.0 (6) | N7—C41—C42—C34 | −177.5 (3) |
C1—C2—C6—N1 | 173.9 (4) | C37—C41—C42—C34 | 0.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2 | 0.85 (1) | 1.79 (2) | 2.628 (4) | 167 (4) |
O1w—H1w2···O3w | 0.85 (1) | 1.92 (2) | 2.748 (4) | 165 (4) |
O2w—H2w1···O6 | 0.86 (1) | 1.78 (1) | 2.614 (4) | 163 (3) |
O2w—H2w2···O4w | 0.85 (1) | 1.85 (1) | 2.706 (4) | 177 (4) |
O3w—H3w1···O4i | 0.84 (1) | 1.90 (1) | 2.735 (4) | 171 (4) |
O3w—H3w2···O5i | 0.84 (1) | 2.05 (1) | 2.883 (4) | 171 (4) |
O4w—H4w1···O3w | 0.84 (1) | 1.97 (2) | 2.781 (4) | 163 (4) |
O4w—H4w2···O5w | 0.84 (1) | 1.93 (1) | 2.766 (4) | 171 (4) |
O5w—H5w1···N1ii | 0.85 (1) | 2.06 (2) | 2.873 (5) | 160 (4) |
O5w—H5w2···N2iii | 0.84 (1) | 2.07 (2) | 2.890 (5) | 165 (4) |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y+1, z; (iii) −x+1, −y+2, −z+1. |