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The title compound, (C3H12N2)2[Ce(C7H3NO4)3](NO3)·3.5H2O, is a nine-coordinate Ce complex obtained from a proton-transfer compound. The mol­ecular structure contains three pyridine-2,6-dicarboxyl­ate species as tridentate ligands and two propane-1,3-diaminium cations as counter-ions. The asymmetric unit also contains one nitrate anion and 3.5 uncoordinated water mol­ecules. In the crystal structure, a wide range of hydrogen-bonding inter­actions connect the various fragments into a supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021404/hk2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021404/hk2042Isup2.hkl
Contains datablock I

CCDC reference: 601607

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.012 Å
  • H-atom completeness 99%
  • Disorder in solvent or counterion
  • R factor = 0.053
  • wR factor = 0.130
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT415_ALERT_2_B Short Inter D-H..H-X H17B .. H18A .. 1.98 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact O1N' .. C27' .. 2.73 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.08 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for N7 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C26 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C27 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1N PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2N' PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 27.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C3 H12 N2
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C27 H40 Ce1 N8 O18.5 Atom count from the _atom_site data: C27 H39.5 Ce1 N8 O18.5 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C27 H40 Ce N8 O18.5 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 54.00 54.00 0.00 H 80.00 79.00 1.00 Ce 2.00 2.00 0.00 N 16.00 16.00 0.00 O 37.00 37.00 0.00
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 8 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(propane-1,3-diaminium) tris(pyridine-2,6-dicarboxylato-κ3O,N,O')cerate(III) nitrate 3.5-hydrate top
Crystal data top
(C3H12N2)2[Ce(C7H3NO4)3](NO3)·3.5H2OZ = 2
Mr = 912.29F(000) = 927
Triclinic, P1Dx = 1.669 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4071 (10) ÅCell parameters from 3525 reflections
b = 13.7063 (14) Åθ = 2.2–28.2°
c = 14.3438 (14) ŵ = 1.34 mm1
α = 65.385 (5)°T = 120 K
β = 80.327 (5)°Prism, colourless
γ = 78.883 (5)°0.40 × 0.20 × 0.20 mm
V = 1816.4 (3) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
8575 independent reflections
Radiation source: fine-focus sealed tube6719 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 1313
Tmin = 0.732, Tmax = 0.769k = 1818
16675 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: mixed
wR(F2) = 0.130H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.04P)2 + 7.9P]
where P = (Fo2 + 2Fc2)/3
8575 reflections(Δ/σ)max < 0.001
518 parametersΔρmax = 3.01 e Å3
20 restraintsΔρmin = 1.45 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ce10.17482 (4)0.66933 (3)0.66280 (3)0.02348 (13)
O10.3200 (5)0.5775 (4)0.8071 (4)0.0251 (10)
O20.4777 (5)0.4529 (4)0.8923 (4)0.0318 (12)
O30.1953 (5)0.6151 (4)0.5125 (4)0.0306 (12)
O40.2505 (6)0.4959 (5)0.4403 (4)0.0356 (13)
O50.3925 (5)0.7362 (4)0.5902 (4)0.0285 (11)
O60.5256 (5)0.8492 (4)0.4749 (4)0.0309 (12)
O70.0395 (5)0.7653 (4)0.5904 (4)0.0259 (10)
O80.1578 (5)0.8970 (4)0.4700 (4)0.0351 (13)
O90.0409 (5)0.5129 (4)0.7374 (4)0.0317 (12)
O100.1088 (6)0.4155 (5)0.8486 (4)0.0376 (13)
O110.1628 (5)0.8039 (4)0.7413 (4)0.0269 (11)
O120.0951 (6)0.8673 (5)0.8641 (5)0.0400 (14)
N10.3414 (6)0.4977 (5)0.6656 (4)0.0241 (12)
N20.1820 (5)0.8496 (5)0.4995 (4)0.0221 (12)
N30.0115 (6)0.6476 (5)0.8297 (4)0.0247 (12)
C10.4182 (7)0.4434 (6)0.7438 (5)0.0240 (14)
C20.5026 (8)0.3514 (6)0.7489 (6)0.0330 (17)
H2A0.55500.31360.80500.040*
C30.5110 (9)0.3137 (7)0.6710 (7)0.0385 (19)
H3A0.56840.24990.67350.046*
C40.4341 (8)0.3711 (7)0.5902 (6)0.0328 (17)
H4A0.44010.34910.53480.039*
C50.3483 (7)0.4612 (6)0.5916 (5)0.0252 (14)
C60.4048 (7)0.4938 (6)0.8216 (5)0.0224 (14)
C70.2583 (7)0.5293 (6)0.5076 (5)0.0265 (15)
C80.2968 (7)0.8856 (6)0.4529 (5)0.0231 (14)
C90.3066 (7)0.9715 (6)0.3586 (6)0.0276 (15)
H9A0.38940.99430.32660.033*
C100.1909 (8)1.0243 (7)0.3110 (6)0.0347 (18)
H10A0.19411.08380.24610.042*
C110.0724 (7)0.9890 (6)0.3595 (6)0.0301 (16)
H11A0.00701.02430.32870.036*
C120.0708 (7)0.9012 (6)0.4540 (5)0.0244 (14)
C130.4150 (7)0.8200 (6)0.5111 (5)0.0249 (15)
C150.0649 (7)0.5688 (6)0.8695 (5)0.0272 (15)
C140.0540 (7)0.8530 (6)0.5076 (5)0.0242 (14)
C190.0018 (7)0.7184 (6)0.8734 (5)0.0274 (15)
C210.0941 (7)0.8041 (6)0.8225 (6)0.0265 (15)
C200.0434 (7)0.4938 (6)0.8152 (6)0.0287 (16)
C160.1575 (7)0.5595 (7)0.9543 (6)0.0329 (17)
H16C0.21130.50330.98140.039*
C180.0870 (8)0.7147 (7)0.9578 (6)0.0343 (18)
H18A0.09230.76570.98770.041*
C170.1689 (8)0.6336 (7)0.9978 (6)0.0378 (19)
H17A0.23220.62971.05490.045*
O140.7676 (7)0.1593 (6)0.8562 (6)0.0586 (19)
H14A0.74230.20430.89810.070*
H14B0.82350.10250.89300.070*
O150.6347 (6)1.0368 (5)0.3379 (5)0.0459 (16)
H15B0.58160.98500.37750.055*
H15A0.70841.03220.36620.055*
N40.5858 (6)0.2494 (5)0.1698 (5)0.0288 (13)
H4B0.63470.25180.11010.043*
H4C0.59820.18100.21920.043*
H4D0.61120.29630.19090.043*
N50.2817 (6)0.3087 (5)0.4008 (4)0.0252 (13)
H5A0.26980.36330.42300.038*
H5B0.33140.25000.44370.038*
H5C0.20210.29060.40060.038*
N60.0969 (8)1.3298 (6)0.2957 (5)0.0428 (18)
H6A0.09781.35410.24560.051*
H6B0.13831.27060.26890.051*
H6C0.14331.38100.34600.051*
N70.1955 (6)1.0463 (6)0.1686 (7)0.122 (5)
H7A0.26661.02740.12910.146*
H7B0.23371.01810.21470.146*
H7C0.14540.99630.12410.146*
C220.4437 (7)0.2809 (7)0.1520 (6)0.0320 (17)
H22A0.42050.23940.11630.038*
H22B0.42780.35890.10690.038*
C230.3562 (7)0.2590 (6)0.2535 (6)0.0294 (16)
H23A0.26610.25480.24290.035*
H23B0.39020.18790.30540.035*
C240.3500 (7)0.3449 (6)0.2945 (5)0.0258 (15)
H24A0.44010.35760.29540.031*
H24B0.30170.41370.24920.031*
C250.0324 (7)1.3057 (6)0.3436 (7)0.073 (3)
H25A0.06211.37560.39150.087*
H25B0.02211.26690.38610.087*
O160.6905 (4)0.3016 (3)0.0370 (3)0.0331 (12)
H16B0.62600.35100.05840.040*
H16A0.76310.33610.05580.040*
C260.1445 (4)1.2389 (3)0.2750 (3)0.115 (12)0.60
H26A0.14581.26150.21810.138*0.60
H26B0.23191.24150.31530.138*0.60
C270.0994 (4)1.1303 (3)0.2376 (3)0.045 (4)0.60
H27A0.09351.11280.29700.054*0.60
H27B0.01101.13140.19920.054*0.60
N1N0.4347 (4)1.0324 (3)0.1120 (3)0.073 (7)0.60
O3N0.3394 (4)1.0969 (3)0.0732 (3)0.082 (6)0.60
O2N0.5272 (4)1.0641 (3)0.1300 (3)0.140 (11)0.60
O1N0.4502 (4)0.9332 (3)0.1369 (3)0.091 (5)0.60
N2N'0.4882 (4)1.0049 (3)0.1221 (3)0.069 (9)0.40
O3N'0.3720 (4)1.0297 (3)0.1037 (3)0.122 (15)0.40
O1N'0.5448 (4)0.9171 (3)0.1787 (3)0.139 (14)0.40
O2N'0.5586 (4)1.0771 (3)0.0785 (3)0.078 (8)0.40
C26'0.0800 (4)1.1990 (3)0.2542 (3)0.081 (12)0.40
H26C0.06391.21310.19060.098*0.40
H26D0.02271.14520.24500.098*0.40
C27'0.2198 (4)1.1465 (3)0.2605 (3)0.101 (14)0.40
H27C0.24661.13370.32450.122*0.40
H27D0.28331.18620.25110.122*0.40
O170.9505 (16)0.0216 (11)0.9746 (10)0.058 (4)0.50
H17B0.94350.08510.94890.070*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ce10.0206 (2)0.0246 (2)0.0215 (2)0.00376 (14)0.00348 (13)0.00464 (15)
O10.024 (2)0.027 (3)0.021 (2)0.001 (2)0.0054 (19)0.007 (2)
O20.032 (3)0.033 (3)0.028 (3)0.002 (2)0.014 (2)0.008 (2)
O30.040 (3)0.031 (3)0.020 (2)0.002 (2)0.007 (2)0.008 (2)
O40.047 (3)0.036 (3)0.028 (3)0.005 (3)0.008 (2)0.015 (3)
O50.021 (2)0.028 (3)0.026 (3)0.005 (2)0.006 (2)0.002 (2)
O60.021 (3)0.033 (3)0.030 (3)0.007 (2)0.003 (2)0.002 (2)
O70.020 (2)0.026 (3)0.025 (3)0.003 (2)0.0036 (19)0.003 (2)
O80.023 (3)0.033 (3)0.038 (3)0.005 (2)0.012 (2)0.001 (2)
O90.033 (3)0.031 (3)0.030 (3)0.012 (2)0.001 (2)0.009 (2)
O100.039 (3)0.041 (3)0.030 (3)0.021 (3)0.002 (2)0.004 (3)
O110.024 (3)0.025 (3)0.030 (3)0.002 (2)0.004 (2)0.008 (2)
O120.039 (3)0.045 (4)0.042 (3)0.004 (3)0.007 (3)0.023 (3)
N10.025 (3)0.025 (3)0.019 (3)0.006 (2)0.001 (2)0.004 (2)
N20.020 (3)0.023 (3)0.021 (3)0.003 (2)0.004 (2)0.006 (2)
N30.021 (3)0.027 (3)0.021 (3)0.002 (2)0.005 (2)0.004 (2)
C10.020 (3)0.026 (4)0.024 (3)0.005 (3)0.003 (3)0.006 (3)
C20.031 (4)0.031 (4)0.033 (4)0.003 (3)0.011 (3)0.009 (3)
C30.040 (5)0.033 (4)0.044 (5)0.010 (4)0.010 (4)0.020 (4)
C40.034 (4)0.035 (4)0.032 (4)0.003 (3)0.005 (3)0.017 (4)
C50.024 (3)0.027 (4)0.023 (3)0.008 (3)0.000 (3)0.008 (3)
C60.022 (3)0.022 (3)0.019 (3)0.008 (3)0.000 (3)0.002 (3)
C70.029 (4)0.028 (4)0.021 (3)0.009 (3)0.001 (3)0.008 (3)
C80.022 (3)0.023 (3)0.022 (3)0.002 (3)0.005 (3)0.006 (3)
C90.025 (4)0.026 (4)0.025 (4)0.006 (3)0.001 (3)0.002 (3)
C100.031 (4)0.031 (4)0.029 (4)0.001 (3)0.008 (3)0.001 (3)
C110.023 (4)0.030 (4)0.028 (4)0.001 (3)0.007 (3)0.001 (3)
C120.022 (3)0.026 (4)0.023 (3)0.004 (3)0.004 (3)0.007 (3)
C130.021 (3)0.027 (4)0.025 (4)0.003 (3)0.005 (3)0.007 (3)
C150.022 (3)0.031 (4)0.020 (3)0.007 (3)0.005 (3)0.000 (3)
C140.020 (3)0.025 (4)0.024 (3)0.002 (3)0.003 (3)0.007 (3)
C190.023 (3)0.030 (4)0.023 (3)0.002 (3)0.008 (3)0.004 (3)
C210.023 (4)0.027 (4)0.028 (4)0.004 (3)0.010 (3)0.010 (3)
C200.027 (4)0.028 (4)0.023 (4)0.010 (3)0.008 (3)0.002 (3)
C160.024 (4)0.039 (4)0.026 (4)0.007 (3)0.004 (3)0.002 (3)
C180.032 (4)0.042 (5)0.027 (4)0.001 (3)0.005 (3)0.014 (4)
C170.027 (4)0.052 (5)0.024 (4)0.001 (4)0.003 (3)0.010 (4)
O140.050 (4)0.053 (4)0.064 (5)0.008 (3)0.001 (3)0.022 (4)
O150.032 (3)0.045 (4)0.043 (3)0.016 (3)0.011 (3)0.007 (3)
N40.027 (3)0.032 (3)0.026 (3)0.006 (3)0.003 (2)0.008 (3)
N50.026 (3)0.024 (3)0.023 (3)0.005 (2)0.006 (2)0.005 (3)
N60.058 (5)0.041 (4)0.029 (4)0.011 (4)0.009 (3)0.009 (3)
N70.200 (17)0.062 (8)0.103 (10)0.024 (9)0.014 (11)0.029 (8)
C220.026 (4)0.047 (5)0.025 (4)0.010 (3)0.003 (3)0.013 (4)
C230.024 (4)0.035 (4)0.026 (4)0.006 (3)0.003 (3)0.007 (3)
C240.023 (4)0.026 (4)0.021 (3)0.004 (3)0.006 (3)0.001 (3)
C250.056 (7)0.091 (10)0.084 (9)0.020 (7)0.003 (6)0.047 (8)
O160.028 (3)0.032 (3)0.029 (3)0.004 (2)0.002 (2)0.003 (2)
C260.061 (15)0.082 (18)0.20 (3)0.036 (14)0.036 (18)0.07 (2)
C270.029 (8)0.068 (12)0.035 (8)0.017 (8)0.015 (6)0.022 (8)
N1N0.11 (2)0.072 (14)0.058 (14)0.043 (14)0.013 (12)0.042 (12)
O3N0.077 (11)0.056 (9)0.094 (13)0.006 (8)0.014 (9)0.025 (9)
O2N0.26 (3)0.070 (14)0.115 (18)0.008 (17)0.085 (19)0.043 (12)
O1N0.095 (13)0.063 (10)0.134 (16)0.026 (9)0.010 (11)0.052 (11)
N2N'0.09 (2)0.08 (2)0.043 (16)0.035 (18)0.004 (14)0.013 (15)
O3N'0.10 (3)0.20 (5)0.09 (2)0.04 (3)0.000 (19)0.08 (3)
O1N'0.081 (19)0.075 (17)0.15 (3)0.023 (15)0.017 (18)0.040 (18)
O2N'0.053 (12)0.069 (15)0.14 (2)0.014 (11)0.017 (13)0.066 (16)
C26'0.08 (3)0.09 (3)0.10 (3)0.03 (2)0.06 (2)0.06 (2)
C27'0.15 (4)0.039 (17)0.12 (3)0.04 (2)0.03 (3)0.04 (2)
O170.080 (11)0.045 (8)0.045 (8)0.007 (7)0.006 (7)0.020 (7)
Geometric parameters (Å, º) top
Ce1—O52.504 (5)O14—H14A1.0006
Ce1—O112.505 (5)O14—H14B0.9000
Ce1—O72.509 (5)O15—H15B0.9184
Ce1—O12.510 (5)O15—H15A0.9061
Ce1—O32.523 (5)N4—C221.493 (9)
Ce1—O92.534 (5)N4—H4B0.9100
Ce1—N22.606 (6)N4—H4C0.9100
Ce1—N12.629 (6)N4—H4D0.9100
Ce1—N32.635 (6)N5—C241.490 (9)
O1—C61.269 (8)N5—H5A0.9100
O2—C61.240 (8)N5—H5B0.9100
O3—C71.255 (9)N5—H5C0.9100
O4—C71.248 (8)N6—C251.449 (12)
O5—C131.260 (9)N6—H6A0.9070
O6—C131.248 (8)N6—H6B0.9000
O7—C141.295 (8)N6—H6C0.9000
O8—C141.224 (8)N7—C27'1.484 (3)
O9—C201.266 (9)N7—C271.498 (3)
O10—C201.260 (9)N7—H7A0.9390
O11—C211.261 (9)N7—H7B0.8997
O12—C211.243 (9)N7—H7C0.9000
N1—C51.336 (9)C22—C231.528 (10)
N1—C11.351 (9)C22—H22A0.9900
N2—C81.343 (9)C22—H22B0.9900
N2—C121.348 (9)C23—C241.507 (10)
N3—C191.339 (9)C23—H23A0.9900
N3—C151.337 (9)C23—H23B0.9900
C1—C21.373 (10)C24—H24A0.9900
C1—C61.515 (10)C24—H24B0.9900
C2—C31.398 (11)C25—C261.547 (3)
C2—H2A0.9500C25—C26'1.549 (3)
C3—C41.383 (11)C25—H25A0.9900
C3—H3A0.9500C25—H25B0.9900
C4—C51.383 (11)O16—H16B0.8514
C4—H4A0.9500O16—H16A0.9117
C5—C71.518 (10)C26—C271.4980
C8—C91.378 (10)C26—H26A0.9900
C8—C131.520 (9)C26—H26B0.9900
C9—C101.403 (10)C27—H27A0.9900
C9—H9A0.9500C27—H27B0.9900
C10—C111.378 (11)N1N—O3N1.2301
C10—H10A0.9500N1N—O2N1.2322
C11—C121.389 (10)N1N—O1N1.2380
C11—H11A0.9500N2N'—O2N'1.2318
C12—C141.512 (10)N2N'—O3N'1.2329
C15—C161.397 (10)N2N'—O1N'1.2368
C15—C201.495 (11)C26'—C27'1.4997
C19—C181.383 (11)C26'—H26C0.9900
C19—C211.523 (11)C26'—H26D0.9900
C16—C171.374 (12)C27'—H27C0.9900
C16—H16C0.9500C27'—H27D0.9900
C18—C171.401 (12)O17—O17i1.67 (3)
C18—H18A0.9500O17—H17B1.0950
C17—H17A0.9500
O5—Ce1—O1179.91 (17)O10—C20—O9123.5 (7)
O5—Ce1—O7124.48 (16)O10—C20—C15119.2 (7)
O11—Ce1—O788.83 (16)O9—C20—C15117.3 (6)
O5—Ce1—O174.42 (16)C17—C16—C15118.5 (7)
O11—Ce1—O174.98 (16)C17—C16—H16C120.8
O7—Ce1—O1153.04 (16)C15—C16—H16C120.8
O5—Ce1—O386.35 (17)C19—C18—C17118.0 (8)
O11—Ce1—O3153.34 (17)C19—C18—H18A121.0
O7—Ce1—O380.25 (17)C17—C18—H18A121.0
O1—Ce1—O3123.10 (17)C16—C17—C18119.8 (7)
O5—Ce1—O9148.84 (18)C16—C17—H17A120.1
O11—Ce1—O9123.32 (17)C18—C17—H17A120.1
O7—Ce1—O980.02 (17)H14A—O14—H14B104.9
O1—Ce1—O990.90 (17)H15B—O15—H15A114.6
O3—Ce1—O978.85 (17)C22—N4—H4B109.5
O5—Ce1—N261.67 (16)C22—N4—H4C109.5
O11—Ce1—N278.50 (17)H4B—N4—H4C109.5
O7—Ce1—N262.82 (16)C22—N4—H4D109.5
O1—Ce1—N2131.76 (17)H4B—N4—H4D109.5
O3—Ce1—N274.87 (17)H4C—N4—H4D109.5
O9—Ce1—N2137.24 (17)C24—N5—H5A109.5
O5—Ce1—N174.54 (17)C24—N5—H5B109.5
O11—Ce1—N1134.06 (17)H5A—N5—H5B109.5
O7—Ce1—N1137.07 (17)C24—N5—H5C109.5
O1—Ce1—N161.77 (17)H5A—N5—H5C109.5
O3—Ce1—N161.57 (17)H5B—N5—H5C109.5
O9—Ce1—N174.30 (18)C25—N6—H6A115.2
N2—Ce1—N1119.10 (18)C25—N6—H6B109.9
O5—Ce1—N3136.61 (17)H6A—N6—H6B108.5
O11—Ce1—N362.10 (18)C25—N6—H6C107.0
O7—Ce1—N377.34 (17)H6A—N6—H6C108.5
O1—Ce1—N376.05 (16)H6B—N6—H6C107.5
O3—Ce1—N3136.78 (18)C27'—N7—C2750.80 (8)
O9—Ce1—N361.23 (18)C27'—N7—H7A106.9
N2—Ce1—N3123.91 (18)C27—N7—H7A150.5
N1—Ce1—N3116.98 (18)C27'—N7—H7B79.4
C6—O1—Ce1127.1 (4)C27—N7—H7B95.9
C7—O3—Ce1126.0 (4)H7A—N7—H7B98.1
C13—O5—Ce1127.1 (4)C27'—N7—H7C154.2
C14—O7—Ce1125.7 (4)C27—N7—H7C103.5
C20—O9—Ce1125.9 (5)H7A—N7—H7C98.1
C21—O11—Ce1126.7 (5)H7B—N7—H7C103.8
C5—N1—C1119.2 (6)N4—C22—C23111.2 (6)
C5—N1—Ce1120.5 (5)N4—C22—H22A109.4
C1—N1—Ce1120.3 (4)C23—C22—H22A109.4
C8—N2—C12119.0 (6)N4—C22—H22B109.4
C8—N2—Ce1121.0 (4)C23—C22—H22B109.4
C12—N2—Ce1119.6 (4)H22A—C22—H22B108.0
C19—N3—C15119.5 (6)C24—C23—C22112.8 (6)
C19—N3—Ce1119.6 (5)C24—C23—H23A109.0
C15—N3—Ce1120.8 (5)C22—C23—H23A109.0
N1—C1—C2121.4 (7)C24—C23—H23B109.0
N1—C1—C6114.6 (6)C22—C23—H23B109.0
C2—C1—C6124.0 (6)H23A—C23—H23B107.8
C1—C2—C3119.5 (7)N5—C24—C23109.3 (6)
C1—C2—H2A120.3N5—C24—H24A109.8
C3—C2—H2A120.3C23—C24—H24A109.8
C4—C3—C2118.7 (7)N5—C24—H24B109.8
C4—C3—H3A120.6C23—C24—H24B109.8
C2—C3—H3A120.6H24A—C24—H24B108.3
C5—C4—C3118.7 (7)N6—C25—C26119.4 (7)
C5—C4—H4A120.6N6—C25—C26'98.5 (6)
C3—C4—H4A120.6N6—C25—H25A107.5
N1—C5—C4122.4 (7)C26—C25—H25A107.5
N1—C5—C7114.5 (6)C26'—C25—H25A140.5
C4—C5—C7123.1 (6)N6—C25—H25B107.5
O2—C6—O1125.0 (7)C26—C25—H25B107.5
O2—C6—C1118.8 (6)C26'—C25—H25B92.4
O1—C6—C1116.2 (6)H25A—C25—H25B107.0
O4—C7—O3124.8 (7)H16B—O16—H16A105.8
O4—C7—C5118.5 (7)C25—C26—C2797.5 (3)
O3—C7—C5116.7 (6)C25—C26—H26A112.3
N2—C8—C9122.6 (6)C27—C26—H26A112.3
N2—C8—C13114.0 (6)C25—C26—H26B112.3
C9—C8—C13123.3 (6)C27—C26—H26B112.3
C8—C9—C10118.2 (7)H26A—C26—H26B109.9
C8—C9—H9A120.9C26—C27—N7109.1 (3)
C10—C9—H9A120.9C26—C27—H27A109.9
C11—C10—C9119.4 (7)N7—C27—H27A109.9
C11—C10—H10A120.3C26—C27—H27B109.9
C9—C10—H10A120.3N7—C27—H27B109.9
C10—C11—C12119.0 (7)H27A—C27—H27B108.3
C10—C11—H11A120.5O3N—N1N—O2N120.7
C12—C11—H11A120.5O3N—N1N—O1N126.2
N2—C12—C11121.8 (6)O2N—N1N—O1N113.1
N2—C12—C14116.3 (6)O2N'—N2N'—O3N'116.2
C11—C12—C14121.8 (6)O2N'—N2N'—O1N'114.7
O6—C13—O5125.5 (7)O3N'—N2N'—O1N'129.1
O6—C13—C8118.5 (6)C27'—C26'—C25119.8 (4)
O5—C13—C8115.9 (6)C27'—C26'—H26C107.4
N3—C15—C16121.8 (7)C25—C26'—H26C107.4
N3—C15—C20114.6 (6)C27'—C26'—H26D107.4
C16—C15—C20123.5 (7)C25—C26'—H26D107.4
O8—C14—O7125.5 (7)H26C—C26'—H26D106.9
O8—C14—C12118.9 (6)N7—C27'—C26'93.4 (2)
O7—C14—C12115.5 (6)N7—C27'—H27C113.0
N3—C19—C18122.3 (7)C26'—C27'—H27C113.0
N3—C19—C21115.1 (6)N7—C27'—H27D113.0
C18—C19—C21122.6 (7)C26'—C27'—H27D113.0
O12—C21—O11126.1 (7)H27C—C27'—H27D110.4
O12—C21—C19117.6 (7)O17i—O17—H17B143.4
O11—C21—C19116.3 (6)
O5—Ce1—O1—C681.2 (5)O3—Ce1—N3—C1522.3 (6)
O11—Ce1—O1—C6164.7 (6)O9—Ce1—N3—C152.6 (5)
O7—Ce1—O1—C6140.3 (5)N2—Ce1—N3—C15127.2 (5)
O3—Ce1—O1—C66.3 (6)N1—Ce1—N3—C1553.9 (5)
O9—Ce1—O1—C670.9 (5)C5—N1—C1—C20.3 (10)
N2—Ce1—O1—C6105.8 (5)Ce1—N1—C1—C2177.7 (6)
N1—Ce1—O1—C60.7 (5)C5—N1—C1—C6178.5 (6)
N3—Ce1—O1—C6130.9 (6)Ce1—N1—C1—C63.6 (8)
O5—Ce1—O3—C783.1 (6)N1—C1—C2—C30.9 (12)
O11—Ce1—O3—C7141.9 (5)C6—C1—C2—C3177.7 (7)
O7—Ce1—O3—C7151.0 (6)C1—C2—C3—C40.5 (13)
O1—Ce1—O3—C714.4 (6)C2—C3—C4—C52.4 (13)
O9—Ce1—O3—C769.4 (6)C1—N1—C5—C41.9 (10)
N2—Ce1—O3—C7144.7 (6)Ce1—N1—C5—C4179.8 (6)
N1—Ce1—O3—C78.7 (5)C1—N1—C5—C7179.6 (6)
N3—Ce1—O3—C791.5 (6)Ce1—N1—C5—C72.5 (8)
O11—Ce1—O5—C1383.8 (6)C3—C4—C5—N13.2 (12)
O7—Ce1—O5—C132.3 (6)C3—C4—C5—C7179.3 (7)
O1—Ce1—O5—C13160.9 (6)Ce1—O1—C6—O2177.5 (5)
O3—Ce1—O5—C1373.3 (6)Ce1—O1—C6—C10.8 (8)
O9—Ce1—O5—C13134.6 (6)N1—C1—C6—O2175.6 (6)
N2—Ce1—O5—C131.5 (5)C2—C1—C6—O23.1 (11)
N1—Ce1—O5—C13134.8 (6)N1—C1—C6—O12.9 (9)
N3—Ce1—O5—C13112.1 (6)C2—C1—C6—O1178.4 (7)
O5—Ce1—O7—C143.8 (6)Ce1—O3—C7—O4168.0 (5)
O11—Ce1—O7—C1480.7 (5)Ce1—O3—C7—C510.8 (9)
O1—Ce1—O7—C14132.9 (5)N1—C5—C7—O4174.1 (6)
O3—Ce1—O7—C1474.9 (5)C4—C5—C7—O48.3 (11)
O9—Ce1—O7—C14155.2 (5)N1—C5—C7—O34.9 (9)
N2—Ce1—O7—C143.0 (5)C4—C5—C7—O3172.8 (7)
N1—Ce1—O7—C14101.5 (6)C12—N2—C8—C92.0 (10)
N3—Ce1—O7—C14142.3 (6)Ce1—N2—C8—C9170.3 (5)
O5—Ce1—O9—C20135.9 (5)C12—N2—C8—C13179.3 (6)
O11—Ce1—O9—C202.9 (6)Ce1—N2—C8—C137.0 (8)
O7—Ce1—O9—C2079.1 (6)N2—C8—C9—C101.4 (11)
O1—Ce1—O9—C2075.4 (6)C13—C8—C9—C10178.4 (7)
O3—Ce1—O9—C20161.0 (6)C8—C9—C10—C110.1 (12)
N2—Ce1—O9—C20108.2 (6)C9—C10—C11—C120.6 (12)
N1—Ce1—O9—C20135.7 (6)C8—N2—C12—C111.2 (10)
N3—Ce1—O9—C201.9 (5)Ce1—N2—C12—C11171.2 (5)
O5—Ce1—O11—C21155.8 (6)C8—N2—C12—C14176.9 (6)
O7—Ce1—O11—C2178.8 (5)Ce1—N2—C12—C144.5 (8)
O1—Ce1—O11—C2179.4 (5)C10—C11—C12—N20.0 (12)
O3—Ce1—O11—C21144.1 (5)C10—C11—C12—C14175.4 (7)
O9—Ce1—O11—C211.6 (6)Ce1—O5—C13—O6177.5 (5)
N2—Ce1—O11—C21141.3 (6)Ce1—O5—C13—C81.3 (9)
N1—Ce1—O11—C2199.1 (6)N2—C8—C13—O6178.1 (6)
N3—Ce1—O11—C212.5 (5)C9—C8—C13—O64.6 (11)
O5—Ce1—N1—C599.4 (5)N2—C8—C13—O55.4 (9)
O11—Ce1—N1—C5158.0 (5)C9—C8—C13—O5171.8 (7)
O7—Ce1—N1—C525.0 (6)C19—N3—C15—C161.6 (10)
O1—Ce1—N1—C5179.7 (6)Ce1—N3—C15—C16176.3 (5)
O3—Ce1—N1—C55.1 (5)C19—N3—C15—C20179.0 (6)
O9—Ce1—N1—C580.5 (5)Ce1—N3—C15—C203.2 (8)
N2—Ce1—N1—C555.3 (5)Ce1—O7—C14—O8176.6 (6)
N3—Ce1—N1—C5125.7 (5)Ce1—O7—C14—C122.0 (8)
O5—Ce1—N1—C182.7 (5)N2—C12—C14—O8179.5 (7)
O11—Ce1—N1—C124.1 (6)C11—C12—C14—O84.9 (11)
O7—Ce1—N1—C1152.9 (4)N2—C12—C14—O71.8 (9)
O1—Ce1—N1—C12.3 (5)C11—C12—C14—O7173.8 (7)
O3—Ce1—N1—C1177.0 (6)C15—N3—C19—C181.3 (10)
O9—Ce1—N1—C197.4 (5)Ce1—N3—C19—C18176.5 (5)
N2—Ce1—N1—C1126.8 (5)C15—N3—C19—C21179.5 (6)
N3—Ce1—N1—C152.2 (5)Ce1—N3—C19—C212.7 (8)
O5—Ce1—N2—C84.7 (5)Ce1—O11—C21—O12175.2 (5)
O11—Ce1—N2—C889.3 (5)Ce1—O11—C21—C194.8 (8)
O7—Ce1—N2—C8176.1 (6)N3—C19—C21—O12175.4 (6)
O1—Ce1—N2—C831.7 (6)C18—C19—C21—O125.4 (10)
O3—Ce1—N2—C889.4 (5)N3—C19—C21—O114.7 (9)
O9—Ce1—N2—C8143.4 (5)C18—C19—C21—O11174.5 (7)
N1—Ce1—N2—C845.0 (5)Ce1—O9—C20—O10179.1 (5)
N3—Ce1—N2—C8133.9 (5)Ce1—O9—C20—C151.1 (9)
O5—Ce1—N2—C12176.9 (6)N3—C15—C20—O10178.4 (6)
O11—Ce1—N2—C1298.5 (5)C16—C15—C20—O102.2 (11)
O7—Ce1—N2—C123.8 (5)N3—C15—C20—O91.4 (9)
O1—Ce1—N2—C12156.0 (4)C16—C15—C20—O9178.0 (7)
O3—Ce1—N2—C1282.8 (5)N3—C15—C16—C170.4 (11)
O9—Ce1—N2—C1228.8 (6)C20—C15—C16—C17179.8 (7)
N1—Ce1—N2—C12127.2 (5)N3—C19—C18—C170.1 (11)
N3—Ce1—N2—C1253.9 (5)C21—C19—C18—C17179.0 (7)
O5—Ce1—N3—C1932.4 (6)C15—C16—C17—C181.1 (11)
O11—Ce1—N3—C190.5 (5)C19—C18—C17—C161.3 (11)
O7—Ce1—N3—C1995.0 (5)N4—C22—C23—C2479.1 (8)
O1—Ce1—N3—C1980.6 (5)C22—C23—C24—N5170.8 (6)
O3—Ce1—N3—C19155.5 (4)N6—C25—C26—C2775.2 (7)
O9—Ce1—N3—C19179.6 (5)C26'—C25—C26—C2718.8 (2)
N2—Ce1—N3—C1950.6 (5)C25—C26—C27—N7178.7 (7)
N1—Ce1—N3—C19128.3 (5)C27'—N7—C27—C2633.5 (4)
O5—Ce1—N3—C15149.8 (5)N6—C25—C26'—C27'172.5 (4)
O11—Ce1—N3—C15178.3 (6)C26—C25—C26'—C27'39.7 (4)
O7—Ce1—N3—C1582.8 (5)C27—N7—C27'—C26'21.2 (3)
O1—Ce1—N3—C15101.5 (5)C25—C26'—C27'—N7170.5 (7)
Symmetry code: (i) x+2, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···O160.911.952.819 (8)159
N4—H4C···O15ii0.912.022.924 (10)173
N4—H4D···O1iii0.912.012.892 (9)163
N5—H5A···O40.911.902.800 (10)168
N5—H5B···O6iii0.911.982.863 (8)164
N5—H5C···O7iv0.911.952.858 (9)173
N5—H5C···O8iv0.912.543.048 (8)116
N6—H6A···O10v0.911.852.750 (10)175
N6—H6B···O14vi0.902.052.86 (1)149
N6—H6C···O3vii0.902.513.179 (9)131
N6—H6C···O4vii0.901.952.842 (10)171
N7—H7A···O2Nviii0.942.112.95 (1)148
N7—H7B···O15viii0.902.343.22 (1)169
N7—H7C···O12ix0.902.022.68 (1)130
O14—H14A···O16x1.001.882.875 (10)174
O14—H14B···o170.902.002.90 (10)179
O15—H15A···O8xi0.912.232.946 (9)135
O15—H15B···O60.921.932.816 (9)161
O16—H16A···O10xii0.911.882.732 (7)154
O16—H16B···O2ix0.851.882.732 (7)176
O17—H17B···O12xiii1.092.002.72 (1)120
Symmetry codes: (ii) x, y1, z; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1; (v) x, y+1, z1; (vi) x1, y+1, z1; (vii) x, y+2, z; (viii) x+1, y+2, z; (ix) x, y, z1; (x) x, y, z+1; (xi) x+1, y, z; (xii) x+1, y, z1; (xiii) x+1, y1, z.
 

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