Aqua­[2,2'-(naphthal­ene-2,3-di­oxy)bis­(N,N-diethyl­acetamide)]trinitratocerium(III) acetonitrile solvate

In the title compound, [Ce(NO₃)₃(C₂₂H₃₀N₂O₄)(H₂O)]·CH₃CN, the Ce^III atom is coordinated by 11 O atoms in a distorted monocapped penta­gonal antiprismatic geometry. The Ce-O(carbon­yl) bond distances [average 2.415 (3) Å] are significantly shorter than the other Ce-O bonds [2.495 (3)-2.931 (3) Å] in the complex.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.034
• wR factor = 0.091
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.39 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.80 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O12
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C5     -   C6     ...       1.32 Ang.
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H24A   ..  H4B3    ..       2.06 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ce1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C23
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H8A    ..  H9B     ..       1.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O10    ..  C7      ..       2.93 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C2 H3 N

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  15 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Aqua[2,2'-(naphthylene-2,3-dioxy)bis(N,N- diethylacetamide)]trinitratocerium(III) acetonitrile solvate

Crystal data

[Ce(NO3)3(C22H30N2O4)(H2O)]·C2H3N	Z = 2
Mr = 771.70	F(000) = 782
Triclinic, P1	Dx = 1.615 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.457 (7) Å	Cell parameters from 6489 reflections
b = 13.732 (11) Å	θ = 3.0–25.0°
c = 15.621 (13) Å	µ = 1.51 mm^−1
α = 115.53 (1)°	T = 295 K
β = 90.89 (1)°	Block, colorless
γ = 102.366 (11)°	0.47 × 0.42 × 0.35 mm
V = 1587 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5429 independent reflections
Radiation source: fine-focus sealed tube	4841 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→9
Tmin = 0.537, Tmax = 0.620	k = −10→16
8010 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 2.3465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
5429 reflections	Δρmax = 1.29 e Å^−3
416 parameters	Δρmin = −1.05 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.126 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ce1	0.36837 (3)	0.517597 (18)	0.712582 (15)	0.02900 (14)
N1	0.1675 (6)	0.1913 (3)	0.4380 (3)	0.0598 (12)
N2	0.7829 (4)	0.7463 (3)	0.9595 (3)	0.0383 (8)
N3	0.4160 (5)	0.6731 (3)	0.6144 (3)	0.0417 (9)
N4	0.0527 (4)	0.5944 (3)	0.7419 (3)	0.0410 (9)
N5	0.1600 (5)	0.4475 (4)	0.8443 (3)	0.0526 (11)
N6	0.2738 (12)	−0.0767 (5)	0.5026 (5)	0.123 (3)
O1	0.2644 (4)	0.3596 (2)	0.5598 (2)	0.0435 (7)
O2	0.4049 (4)	0.2960 (2)	0.6666 (2)	0.0384 (7)
O3	0.5785 (4)	0.6525 (2)	0.8392 (2)	0.0411 (7)
O4	0.5900 (4)	0.4558 (2)	0.8157 (2)	0.0352 (6)
O5	0.3685 (4)	0.5694 (3)	0.5645 (2)	0.0436 (7)
O6	0.4376 (5)	0.7061 (3)	0.7041 (2)	0.0564 (9)
O7	0.4394 (5)	0.7377 (3)	0.5792 (3)	0.0666 (11)
O8	0.0804 (4)	0.5321 (3)	0.6610 (2)	0.0508 (8)
O9	0.1678 (4)	0.6383 (3)	0.8085 (3)	0.0571 (9)
O10	−0.0819 (4)	0.6121 (4)	0.7574 (3)	0.0650 (11)
O11	0.1285 (5)	0.3973 (3)	0.7542 (3)	0.0685 (11)
O12	0.3019 (5)	0.5073 (4)	0.8756 (3)	0.0717 (12)
O13	0.0614 (6)	0.4374 (5)	0.8963 (4)	0.0981 (17)
O14	0.6235 (4)	0.5017 (3)	0.6349 (2)	0.0444 (8)
H1	0.6643	0.4695	0.5859	0.050*
H2	0.7151	0.5357	0.6716	0.050*
C1	0.2460 (6)	0.2579 (4)	0.5249 (3)	0.0385 (10)
C2	0.3097 (7)	0.2071 (4)	0.5828 (3)	0.0480 (12)
H2A	0.2196	0.1646	0.5998	0.058*
H2B	0.3759	0.1576	0.5461	0.058*
C3	0.1136 (8)	0.2412 (5)	0.3790 (4)	0.0628 (16)
C4B	−0.039 (2)	0.2659 (19)	0.3973 (15)	0.076 (3)	0.37
H4B1	−0.1182	0.2000	0.3893	0.114*	0.37
H4B2	−0.0723	0.2917	0.3534	0.114*	0.37
H4B3	−0.0309	0.3227	0.4616	0.114*	0.37
H3C	0.1843	0.3151	0.3994	0.050*	0.37
H3D	0.1260	0.1970	0.3130	0.050*	0.37
C4A	−0.0642 (13)	0.1906 (11)	0.3332 (8)	0.076 (3)	0.63
H4A1	−0.1340	0.1953	0.3820	0.114*	0.63
H4A2	−0.0772	0.1140	0.2884	0.114*	0.63
H4A3	−0.0928	0.2309	0.3005	0.114*	0.63
H3A	0.1799	0.2304	0.3275	0.050*	0.63
H3B	0.1304	0.3207	0.4183	0.050*	0.63
C5	0.1191 (12)	0.0647 (7)	0.3990 (6)	0.098 (3)
H5A	0.1251	0.0428	0.4501	0.117*
H5B	0.0094	0.0340	0.3653	0.117*
C7	0.6821 (5)	0.6527 (3)	0.8968 (3)	0.0329 (9)
C8	0.6891 (5)	0.5442 (3)	0.8982 (3)	0.0374 (9)
H8A	0.8006	0.5369	0.8978	0.045*
H8B	0.6492	0.5424	0.9555	0.045*
C9	0.9187 (6)	0.7519 (4)	1.0224 (4)	0.0527 (12)
H9A	1.0176	0.7975	1.0154	0.063*
H9B	0.9345	0.6776	1.0022	0.063*
C10	0.8929 (11)	0.7986 (8)	1.1252 (5)	0.103 (3)
H10A	0.9848	0.7991	1.1623	0.154*
H10B	0.7959	0.7535	1.1330	0.154*
H10C	0.8813	0.8732	1.1465	0.154*
C11	0.7711 (6)	0.8516 (4)	0.9594 (3)	0.0464 (11)
H11A	0.8050	0.9117	1.0234	0.056*
H11B	0.6583	0.8470	0.9415	0.056*
C12	0.8741 (10)	0.8771 (5)	0.8919 (5)	0.079 (2)
H12A	0.8634	0.9461	0.8938	0.119*
H12B	0.8395	0.8184	0.8283	0.119*
H12C	0.9861	0.8831	0.9101	0.119*
C13	0.4612 (5)	0.2640 (3)	0.7316 (3)	0.0341 (9)
C14	0.4301 (6)	0.1574 (4)	0.7207 (3)	0.0427 (10)
H14	0.3690	0.0997	0.6652	0.051*
C15	0.4897 (6)	0.1334 (4)	0.7932 (3)	0.0401 (10)
C16	0.4579 (7)	0.0234 (4)	0.7844 (4)	0.0544 (13)
H16	0.3979	−0.0356	0.7293	0.065*
C17	0.5143 (7)	0.0034 (5)	0.8558 (4)	0.0593 (14)
H17	0.4934	−0.0691	0.8491	0.071*
C18	0.6033 (7)	0.0913 (5)	0.9391 (4)	0.0536 (13)
H18	0.6391	0.0769	0.9880	0.064*
C19	0.6389 (6)	0.1979 (4)	0.9501 (4)	0.0470 (11)
H19	0.7001	0.2553	1.0058	0.056*
C20	0.5827 (5)	0.2214 (4)	0.8770 (3)	0.0378 (9)
C21	0.6185 (5)	0.3307 (4)	0.8848 (3)	0.0380 (10)
H21	0.6833	0.3888	0.9387	0.046*
C22	0.5601 (5)	0.3525 (3)	0.8149 (3)	0.0344 (9)
C23	0.2422 (9)	−0.1673 (5)	0.4533 (5)	0.0682 (16)
C24	0.2002 (8)	−0.2848 (5)	0.3911 (5)	0.081 (2)
H24A	0.1195	−0.3220	0.4167	0.122*
H24B	0.2958	−0.3131	0.3862	0.122*
H24C	0.1571	−0.2977	0.3289	0.122*
C6	0.2275 (14)	0.0317 (12)	0.3402 (9)	0.144 (4)
H6A	0.2293	0.0627	0.2956	0.216*
H6B	0.1988	−0.0481	0.3062	0.216*
H6C	0.3334	0.0563	0.3761	0.216*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ce1	0.02682 (17)	0.02935 (17)	0.02670 (17)	0.00608 (9)	0.00103 (9)	0.00915 (11)
N1	0.093 (4)	0.035 (2)	0.040 (2)	0.005 (2)	−0.021 (2)	0.0113 (18)
N2	0.0374 (19)	0.0330 (19)	0.0358 (19)	0.0002 (15)	−0.0041 (15)	0.0115 (16)
N3	0.040 (2)	0.042 (2)	0.051 (2)	0.0130 (17)	0.0065 (17)	0.027 (2)
N4	0.033 (2)	0.049 (2)	0.045 (2)	0.0129 (17)	0.0066 (17)	0.0226 (19)
N5	0.049 (3)	0.078 (3)	0.055 (3)	0.026 (2)	0.019 (2)	0.046 (2)
N6	0.216 (9)	0.054 (4)	0.086 (5)	0.025 (5)	0.011 (5)	0.024 (3)
O1	0.063 (2)	0.0275 (16)	0.0334 (16)	0.0090 (14)	−0.0071 (14)	0.0087 (13)
O2	0.0474 (17)	0.0291 (15)	0.0332 (15)	0.0048 (13)	−0.0093 (13)	0.0115 (13)
O3	0.0392 (17)	0.0333 (16)	0.0423 (17)	0.0027 (13)	−0.0101 (14)	0.0124 (13)
O4	0.0429 (16)	0.0265 (14)	0.0316 (15)	0.0036 (12)	−0.0048 (12)	0.0114 (12)
O5	0.0502 (19)	0.0409 (18)	0.0408 (17)	0.0104 (15)	0.0075 (14)	0.0194 (15)
O6	0.085 (3)	0.0398 (18)	0.0410 (19)	0.0151 (18)	−0.0047 (18)	0.0156 (15)
O7	0.085 (3)	0.054 (2)	0.074 (3)	0.011 (2)	0.009 (2)	0.045 (2)
O8	0.0451 (19)	0.063 (2)	0.0410 (18)	0.0216 (17)	0.0060 (15)	0.0168 (17)
O9	0.0447 (19)	0.063 (2)	0.050 (2)	0.0216 (17)	−0.0018 (16)	0.0093 (17)
O10	0.0347 (18)	0.095 (3)	0.070 (2)	0.0315 (19)	0.0184 (17)	0.033 (2)
O11	0.070 (3)	0.068 (3)	0.060 (2)	−0.010 (2)	0.004 (2)	0.033 (2)
O12	0.058 (2)	0.110 (4)	0.046 (2)	0.020 (2)	0.0078 (18)	0.034 (2)
O13	0.088 (3)	0.148 (5)	0.112 (4)	0.050 (3)	0.062 (3)	0.096 (4)
O14	0.0336 (16)	0.061 (2)	0.0364 (16)	0.0158 (15)	0.0085 (13)	0.0178 (15)
C1	0.043 (2)	0.036 (2)	0.031 (2)	0.0015 (19)	−0.0033 (18)	0.0135 (19)
C2	0.064 (3)	0.031 (2)	0.035 (2)	0.003 (2)	−0.012 (2)	0.0072 (19)
C3	0.096 (4)	0.055 (3)	0.037 (3)	0.007 (3)	−0.013 (3)	0.026 (2)
C4B	0.074 (6)	0.105 (9)	0.075 (7)	0.028 (6)	0.000 (6)	0.060 (6)
C4A	0.074 (6)	0.105 (9)	0.075 (7)	0.028 (6)	0.000 (6)	0.060 (6)
C5	0.129 (7)	0.088 (5)	0.068 (4)	0.041 (5)	−0.015 (5)	0.021 (4)
C7	0.030 (2)	0.034 (2)	0.029 (2)	0.0023 (17)	0.0007 (17)	0.0117 (17)
C8	0.039 (2)	0.033 (2)	0.032 (2)	0.0013 (18)	−0.0056 (18)	0.0116 (18)
C9	0.043 (3)	0.045 (3)	0.055 (3)	−0.002 (2)	−0.011 (2)	0.015 (2)
C10	0.131 (7)	0.117 (6)	0.052 (4)	0.054 (6)	−0.014 (4)	0.021 (4)
C11	0.051 (3)	0.032 (2)	0.046 (3)	0.002 (2)	−0.004 (2)	0.012 (2)
C12	0.117 (6)	0.051 (3)	0.072 (4)	0.013 (4)	0.025 (4)	0.032 (3)
C13	0.035 (2)	0.034 (2)	0.031 (2)	0.0089 (18)	0.0017 (17)	0.0129 (18)
C14	0.050 (3)	0.030 (2)	0.040 (2)	0.007 (2)	−0.003 (2)	0.0100 (19)
C15	0.044 (2)	0.035 (2)	0.046 (3)	0.0121 (19)	0.004 (2)	0.020 (2)
C16	0.066 (3)	0.034 (3)	0.060 (3)	0.008 (2)	−0.002 (3)	0.020 (2)
C17	0.074 (4)	0.047 (3)	0.074 (4)	0.018 (3)	0.007 (3)	0.041 (3)
C18	0.064 (3)	0.055 (3)	0.056 (3)	0.020 (3)	0.007 (3)	0.034 (3)
C19	0.051 (3)	0.049 (3)	0.044 (3)	0.014 (2)	0.007 (2)	0.023 (2)
C20	0.037 (2)	0.038 (2)	0.039 (2)	0.0107 (19)	0.0059 (18)	0.0166 (19)
C21	0.037 (2)	0.038 (2)	0.034 (2)	0.0067 (18)	−0.0023 (18)	0.0123 (19)
C22	0.035 (2)	0.029 (2)	0.033 (2)	0.0054 (17)	0.0034 (17)	0.0099 (17)
C23	0.086 (4)	0.053 (4)	0.064 (4)	0.021 (3)	0.009 (3)	0.022 (3)
C24	0.064 (4)	0.062 (4)	0.087 (5)	0.010 (3)	0.002 (3)	0.008 (3)
C6	0.122 (9)	0.195 (12)	0.149 (10)	0.038 (9)	0.026 (8)	0.107 (10)

Geometric parameters (Å, º)

Ce1—O1	2.415 (3)	C4B—H4B3	0.9600
Ce1—O2	2.898 (4)	C4A—H4A1	0.9600
Ce1—O3	2.414 (3)	C4A—H4A2	0.9600
Ce1—O4	2.931 (3)	C4A—H4A3	0.9600
Ce1—O5	2.697 (4)	C5—C6	1.317 (13)
Ce1—O6	2.590 (4)	C5—H5A	0.9700
Ce1—O8	2.628 (4)	C5—H5B	0.9700
Ce1—O9	2.648 (4)	C7—C8	1.512 (6)
Ce1—O11	2.607 (4)	C8—H8A	0.9700
Ce1—O12	2.672 (4)	C8—H8B	0.9700
Ce1—O14	2.495 (3)	C9—C10	1.490 (9)
N1—C1	1.327 (6)	C9—H9A	0.9700
N1—C3	1.481 (7)	C9—H9B	0.9700
N1—C5	1.528 (9)	C10—H10A	0.9600
N2—C7	1.325 (5)	C10—H10B	0.9600
N2—C9	1.467 (6)	C10—H10C	0.9600
N2—C11	1.472 (6)	C11—C12	1.486 (8)
N3—O7	1.215 (5)	C11—H11A	0.9700
N3—O5	1.259 (5)	C11—H11B	0.9700
N3—O6	1.269 (5)	C12—H12A	0.9600
N4—O10	1.221 (5)	C12—H12B	0.9600
N4—O8	1.243 (5)	C12—H12C	0.9600
N4—O9	1.253 (5)	C13—C14	1.364 (6)
N5—O13	1.201 (6)	C13—C22	1.427 (6)
N5—O12	1.252 (6)	C14—C15	1.421 (7)
N5—O11	1.265 (6)	C14—H14	0.9300
N6—C23	1.113 (8)	C15—C20	1.411 (6)
O1—C1	1.232 (5)	C15—C16	1.422 (7)
O2—C13	1.381 (5)	C16—C17	1.360 (8)
O2—C2	1.422 (5)	C16—H16	0.9300
O3—C7	1.245 (5)	C17—C18	1.394 (8)
O4—C22	1.382 (5)	C17—H17	0.9300
O4—C8	1.421 (5)	C18—C19	1.363 (7)
O14—H1	0.8273	C18—H18	0.9300
O14—H2	0.8642	C19—C20	1.415 (7)
C1—C2	1.512 (7)	C19—H19	0.9300
C2—H2A	0.9700	C20—C21	1.416 (6)
C2—H2B	0.9700	C21—C22	1.361 (6)
C3—C4B	1.41 (2)	C21—H21	0.9300
C3—C4A	1.531 (13)	C23—C24	1.437 (9)
C3—H3C	0.972	C24—H24A	0.9600
C3—H3D	0.966	C24—H24B	0.9600
C3—H3A	0.964	C24—H24C	0.9600
C3—H3B	0.971	C6—H6A	0.9600
C4B—H4B1	0.9600	C6—H6B	0.9600
C4B—H4B2	0.9600	C6—H6C	0.9600
O3—Ce1—O1	154.95 (12)	C4B—C3—H3D	116.6 (10)
O3—Ce1—O14	76.76 (12)	N1—C3—H3D	109.1 (5)
O1—Ce1—O14	79.11 (12)	H3C—C3—H3D	107.6 (6)
O3—Ce1—O6	68.99 (12)	N1—C3—H3A	109.2 (6)
O1—Ce1—O6	113.53 (12)	C4A—C3—H3A	106.9 (6)
O14—Ce1—O6	80.69 (12)	N1—C3—H3B	108.7 (4)
O3—Ce1—O11	118.60 (13)	C4A—C3—H3B	109.7 (7)
O1—Ce1—O11	77.12 (13)	H3A—C3—H3B	107.9 (6)
O14—Ce1—O11	140.21 (14)	C3—C4B—H4B1	109.5
O6—Ce1—O11	138.35 (14)	C3—C4B—H4B2	109.5
O3—Ce1—O8	130.17 (11)	C3—C4B—H4B3	109.5
O1—Ce1—O8	72.70 (11)	C3—C4A—H4A1	109.5
O14—Ce1—O8	133.53 (11)	C3—C4A—H4A2	109.5
O6—Ce1—O8	77.83 (12)	H4A1—C4A—H4A2	109.5
O11—Ce1—O8	66.95 (14)	C3—C4A—H4A3	109.5
O3—Ce1—O9	85.85 (12)	H4A1—C4A—H4A3	109.5
O1—Ce1—O9	118.93 (12)	H4A2—C4A—H4A3	109.5
O14—Ce1—O9	150.62 (13)	C6—C5—N1	103.5 (10)
O6—Ce1—O9	70.96 (14)	C6—C5—H5A	111.1
O11—Ce1—O9	69.08 (15)	N1—C5—H5A	111.1
O8—Ce1—O9	47.80 (11)	C6—C5—H5B	111.1
O3—Ce1—O12	71.12 (13)	N1—C5—H5B	111.1
O1—Ce1—O12	120.91 (14)	H5A—C5—H5B	109.0
O14—Ce1—O12	128.61 (12)	O3—C7—N2	121.6 (4)
O6—Ce1—O12	121.11 (13)	O3—C7—C8	119.4 (4)
O11—Ce1—O12	47.49 (13)	N2—C7—C8	119.0 (4)
O8—Ce1—O12	97.69 (12)	O4—C8—C7	108.0 (3)
O9—Ce1—O12	64.60 (14)	O4—C8—H8A	110.1
O3—Ce1—O5	109.95 (12)	C7—C8—H8A	110.1
O1—Ce1—O5	66.03 (12)	O4—C8—H8B	110.1
O14—Ce1—O5	67.69 (11)	C7—C8—H8B	110.1
O6—Ce1—O5	47.70 (10)	H8A—C8—H8B	108.4
O11—Ce1—O5	127.60 (12)	N2—C9—C10	113.5 (5)
O8—Ce1—O5	67.32 (11)	N2—C9—H9A	108.9
O9—Ce1—O5	97.21 (12)	C10—C9—H9A	108.9
O12—Ce1—O5	161.81 (13)	N2—C9—H9B	108.9
O3—Ce1—O2	109.16 (10)	C10—C9—H9B	108.9
O1—Ce1—O2	56.95 (10)	H9A—C9—H9B	107.7
O14—Ce1—O2	73.99 (10)	C9—C10—H10A	109.5
O6—Ce1—O2	154.17 (12)	C9—C10—H10B	109.5
O11—Ce1—O2	66.33 (13)	H10A—C10—H10B	109.5
O8—Ce1—O2	116.51 (10)	C9—C10—H10C	109.5
O9—Ce1—O2	134.80 (12)	H10A—C10—H10C	109.5
O12—Ce1—O2	79.98 (12)	H10B—C10—H10C	109.5
O5—Ce1—O2	115.40 (9)	N2—C11—C12	111.8 (4)
O3—Ce1—O4	56.94 (10)	N2—C11—H11A	109.3
O1—Ce1—O4	108.23 (11)	C12—C11—H11A	109.3
O14—Ce1—O4	70.48 (11)	N2—C11—H11B	109.3
O6—Ce1—O4	122.69 (11)	C12—C11—H11B	109.3
O11—Ce1—O4	87.33 (13)	H11A—C11—H11B	107.9
O8—Ce1—O4	153.65 (10)	C11—C12—H12A	109.5
O9—Ce1—O4	118.89 (11)	C11—C12—H12B	109.5
O12—Ce1—O4	58.51 (12)	H12A—C12—H12B	109.5
O5—Ce1—O4	138.11 (9)	C11—C12—H12C	109.5
O2—Ce1—O4	52.72 (8)	H12A—C12—H12C	109.5
C1—N1—C3	119.0 (4)	H12B—C12—H12C	109.5
C1—N1—C5	122.5 (5)	C14—C13—O2	125.1 (4)
C3—N1—C5	118.3 (5)	C14—C13—C22	119.9 (4)
C7—N2—C9	124.5 (4)	O2—C13—C22	115.0 (4)
C7—N2—C11	118.4 (4)	C13—C14—C15	120.8 (4)
C9—N2—C11	116.7 (4)	C13—C14—H14	119.6
O7—N3—O5	122.3 (4)	C15—C14—H14	119.6
O7—N3—O6	122.0 (4)	C20—C15—C14	119.2 (4)
O5—N3—O6	115.7 (4)	C20—C15—C16	118.7 (4)
O10—N4—O8	122.0 (4)	C14—C15—C16	122.1 (4)
O10—N4—O9	120.2 (4)	C17—C16—C15	120.8 (5)
O8—N4—O9	117.8 (4)	C17—C16—H16	119.6
O13—N5—O12	122.3 (5)	C15—C16—H16	119.6
O13—N5—O11	122.4 (5)	C16—C17—C18	120.1 (5)
O12—N5—O11	115.3 (4)	C16—C17—H17	120.0
C1—O1—Ce1	136.9 (3)	C18—C17—H17	120.0
C13—O2—C2	114.6 (3)	C19—C18—C17	121.3 (5)
C13—O2—Ce1	124.9 (2)	C19—C18—H18	119.3
C2—O2—Ce1	116.9 (3)	C17—C18—H18	119.3
C7—O3—Ce1	137.6 (3)	C18—C19—C20	120.0 (5)
C22—O4—C8	115.0 (3)	C18—C19—H19	120.0
C22—O4—Ce1	123.3 (2)	C20—C19—H19	120.0
C8—O4—Ce1	116.4 (2)	C15—C20—C19	119.2 (4)
N3—O5—Ce1	95.8 (2)	C15—C20—C21	118.8 (4)
N3—O6—Ce1	100.8 (3)	C19—C20—C21	122.0 (4)
N4—O8—Ce1	97.2 (3)	C22—C21—C20	121.3 (4)
N4—O9—Ce1	96.0 (3)	C22—C21—H21	119.3
N5—O11—Ce1	98.4 (3)	C20—C21—H21	119.3
N5—O12—Ce1	95.6 (3)	C21—C22—O4	125.4 (4)
Ce1—O14—H1	146.5	C21—C22—C13	119.9 (4)
Ce1—O14—H2	117.3	O4—C22—C13	114.7 (4)
H1—O14—H2	95.6	N6—C23—C24	178.9 (8)
O1—C1—N1	121.4 (4)	C23—C24—H24A	109.5
O1—C1—C2	119.6 (4)	C23—C24—H24B	109.5
N1—C1—C2	118.9 (4)	H24A—C24—H24B	109.5
O2—C2—C1	107.3 (4)	C23—C24—H24C	109.5
O2—C2—H2A	110.2	H24A—C24—H24C	109.5
C1—C2—H2A	110.2	H24B—C24—H24C	109.5
O2—C2—H2B	110.2	C5—C6—H6A	109.5
C1—C2—H2B	110.2	C5—C6—H6B	109.5
H2A—C2—H2B	108.5	H6A—C6—H6B	109.5
C4B—C3—N1	113.0 (9)	C5—C6—H6C	109.5
N1—C3—C4A	114.2 (6)	H6A—C6—H6C	109.5
C4B—C3—H3C	101.2 (11)	H6B—C6—H6C	109.5
N1—C3—H3C	108.6 (5)
O3—Ce1—O1—C1	72.1 (5)	O8—N4—O9—Ce1	−10.7 (4)
O14—Ce1—O1—C1	87.8 (5)	O3—Ce1—O9—N4	165.9 (3)
O6—Ce1—O1—C1	162.6 (4)	O1—Ce1—O9—N4	−10.3 (3)
O11—Ce1—O1—C1	−60.0 (5)	O14—Ce1—O9—N4	112.5 (3)
O8—Ce1—O1—C1	−129.6 (5)	O6—Ce1—O9—N4	96.7 (3)
O9—Ce1—O1—C1	−117.0 (5)	O11—Ce1—O9—N4	−71.3 (3)
O12—Ce1—O1—C1	−40.9 (5)	O8—Ce1—O9—N4	6.0 (2)
O5—Ce1—O1—C1	158.1 (5)	O12—Ce1—O9—N4	−123.1 (3)
O2—Ce1—O1—C1	10.0 (4)	O5—Ce1—O9—N4	56.3 (3)
O4—Ce1—O1—C1	22.8 (5)	O2—Ce1—O9—N4	−81.0 (3)
O3—Ce1—O2—C13	33.1 (3)	O4—Ce1—O9—N4	−145.8 (3)
O1—Ce1—O2—C13	−170.3 (3)	O13—N5—O11—Ce1	162.9 (5)
O14—Ce1—O2—C13	102.5 (3)	O12—N5—O11—Ce1	−18.0 (5)
O6—Ce1—O2—C13	114.2 (3)	O3—Ce1—O11—N5	8.8 (4)
O11—Ce1—O2—C13	−80.6 (3)	O1—Ce1—O11—N5	167.8 (3)
O8—Ce1—O2—C13	−126.4 (3)	O14—Ce1—O11—N5	113.1 (3)
O9—Ce1—O2—C13	−70.7 (3)	O6—Ce1—O11—N5	−81.1 (4)
O12—Ce1—O2—C13	−32.8 (3)	O8—Ce1—O11—N5	−115.7 (3)
O5—Ce1—O2—C13	157.5 (3)	O9—Ce1—O11—N5	−64.0 (3)
O4—Ce1—O2—C13	25.1 (3)	O12—Ce1—O11—N5	10.2 (3)
O3—Ce1—O2—C2	−169.5 (3)	O5—Ce1—O11—N5	−146.8 (3)
O1—Ce1—O2—C2	−12.8 (3)	O2—Ce1—O11—N5	108.5 (3)
O14—Ce1—O2—C2	−100.1 (3)	O4—Ce1—O11—N5	58.4 (3)
O6—Ce1—O2—C2	−88.3 (4)	O13—N5—O12—Ce1	−163.4 (5)
O11—Ce1—O2—C2	76.9 (3)	O11—N5—O12—Ce1	17.5 (5)
O8—Ce1—O2—C2	31.0 (3)	O3—Ce1—O12—N5	168.4 (3)
O9—Ce1—O2—C2	86.8 (3)	O1—Ce1—O12—N5	−36.0 (4)
O12—Ce1—O2—C2	124.7 (3)	O14—Ce1—O12—N5	−137.3 (3)
O5—Ce1—O2—C2	−45.1 (3)	O6—Ce1—O12—N5	118.8 (3)
O4—Ce1—O2—C2	−177.5 (3)	O11—Ce1—O12—N5	−10.3 (3)
O1—Ce1—O3—C7	−63.3 (5)	O8—Ce1—O12—N5	38.4 (3)
O14—Ce1—O3—C7	−79.1 (4)	O9—Ce1—O12—N5	73.9 (3)
O6—Ce1—O3—C7	−164.1 (4)	O5—Ce1—O12—N5	71.8 (5)
O11—Ce1—O3—C7	61.3 (4)	O2—Ce1—O12—N5	−77.3 (3)
O8—Ce1—O3—C7	144.2 (4)	O4—Ce1—O12—N5	−129.4 (4)
O9—Ce1—O3—C7	124.7 (4)	Ce1—O1—C1—N1	173.0 (4)
O12—Ce1—O3—C7	60.1 (4)	Ce1—O1—C1—C2	−5.2 (7)
O5—Ce1—O3—C7	−139.1 (4)	C3—N1—C1—O1	5.3 (8)
O2—Ce1—O3—C7	−11.6 (4)	C5—N1—C1—O1	−170.0 (6)
O4—Ce1—O3—C7	−4.0 (4)	C3—N1—C1—C2	−176.4 (5)
O3—Ce1—O4—C22	162.8 (3)	C5—N1—C1—C2	8.2 (9)
O1—Ce1—O4—C22	−39.7 (3)	C13—O2—C2—C1	174.8 (4)
O14—Ce1—O4—C22	−110.6 (3)	Ce1—O2—C2—C1	15.1 (5)
O6—Ce1—O4—C22	−175.0 (3)	O1—C1—C2—O2	−8.8 (6)
O11—Ce1—O4—C22	35.8 (3)	N1—C1—C2—O2	172.9 (4)
O8—Ce1—O4—C22	48.0 (4)	C1—N1—C3—C4B	−85.7 (12)
O9—Ce1—O4—C22	100.1 (3)	C5—N1—C3—C4B	89.8 (12)
O12—Ce1—O4—C22	75.9 (3)	C1—N1—C3—C4A	−131.7 (7)
O5—Ce1—O4—C22	−113.8 (3)	C5—N1—C3—C4A	43.8 (10)
O2—Ce1—O4—C22	−26.2 (3)	C1—N1—C5—C6	−103.3 (9)
O3—Ce1—O4—C8	9.9 (3)	C3—N1—C5—C6	81.3 (9)
O1—Ce1—O4—C8	167.4 (3)	Ce1—O3—C7—N2	179.9 (3)
O14—Ce1—O4—C8	96.5 (3)	Ce1—O3—C7—C8	−2.5 (6)
O6—Ce1—O4—C8	32.1 (3)	C9—N2—C7—O3	−173.2 (4)
O11—Ce1—O4—C8	−117.1 (3)	C11—N2—C7—O3	−0.5 (6)
O8—Ce1—O4—C8	−104.9 (3)	C9—N2—C7—C8	9.2 (6)
O9—Ce1—O4—C8	−52.8 (3)	C11—N2—C7—C8	−178.0 (4)
O12—Ce1—O4—C8	−77.0 (3)	C22—O4—C8—C7	−169.0 (3)
O5—Ce1—O4—C8	93.3 (3)	Ce1—O4—C8—C7	−13.9 (4)
O2—Ce1—O4—C8	−179.1 (3)	O3—C7—C8—O4	11.8 (5)
O7—N3—O5—Ce1	178.7 (4)	N2—C7—C8—O4	−170.6 (4)
O6—N3—O5—Ce1	−1.5 (4)	C7—N2—C9—C10	−110.7 (6)
O3—Ce1—O5—N3	−31.3 (3)	C11—N2—C9—C10	76.4 (7)
O1—Ce1—O5—N3	175.4 (3)	C7—N2—C11—C12	−88.1 (6)
O14—Ce1—O5—N3	−97.0 (3)	C9—N2—C11—C12	85.3 (6)
O6—Ce1—O5—N3	0.9 (2)	C2—O2—C13—C14	−0.8 (6)
O11—Ce1—O5—N3	126.0 (3)	Ce1—O2—C13—C14	157.1 (3)
O8—Ce1—O5—N3	95.0 (3)	C2—O2—C13—C22	178.6 (4)
O9—Ce1—O5—N3	56.9 (3)	Ce1—O2—C13—C22	−23.5 (5)
O12—Ce1—O5—N3	58.8 (5)	O2—C13—C14—C15	−178.1 (4)
O2—Ce1—O5—N3	−155.3 (2)	C22—C13—C14—C15	2.5 (7)
O4—Ce1—O5—N3	−93.6 (3)	C13—C14—C15—C20	−0.2 (7)
O7—N3—O6—Ce1	−178.6 (4)	C13—C14—C15—C16	179.3 (5)
O5—N3—O6—Ce1	1.6 (4)	C20—C15—C16—C17	0.8 (8)
O3—Ce1—O6—N3	146.6 (3)	C14—C15—C16—C17	−178.8 (5)
O1—Ce1—O6—N3	−6.4 (3)	C15—C16—C17—C18	0.5 (9)
O14—Ce1—O6—N3	67.3 (3)	C16—C17—C18—C19	−1.5 (9)
O11—Ce1—O6—N3	−103.5 (3)	C17—C18—C19—C20	1.1 (8)
O8—Ce1—O6—N3	−71.2 (3)	C14—C15—C20—C19	178.5 (4)
O9—Ce1—O6—N3	−120.5 (3)	C16—C15—C20—C19	−1.1 (7)
O12—Ce1—O6—N3	−162.9 (3)	C14—C15—C20—C21	−2.2 (6)
O5—Ce1—O6—N3	−0.9 (2)	C16—C15—C20—C21	178.2 (4)
O2—Ce1—O6—N3	55.8 (4)	C18—C19—C20—C15	0.2 (7)
O4—Ce1—O6—N3	126.8 (3)	C18—C19—C20—C21	−179.1 (5)
O10—N4—O8—Ce1	−168.5 (4)	C15—C20—C21—C22	2.4 (6)
O9—N4—O8—Ce1	10.8 (4)	C19—C20—C21—C22	−178.3 (4)
O3—Ce1—O8—N4	−32.8 (3)	C20—C21—C22—O4	−179.2 (4)
O1—Ce1—O8—N4	159.0 (3)	C20—C21—C22—C13	−0.2 (6)
O14—Ce1—O8—N4	−145.6 (3)	C8—O4—C22—C21	−0.7 (6)
O6—Ce1—O8—N4	−81.3 (3)	Ce1—O4—C22—C21	−153.9 (3)
O11—Ce1—O8—N4	76.0 (3)	C8—O4—C22—C13	−179.7 (4)
O9—Ce1—O8—N4	−6.1 (2)	Ce1—O4—C22—C13	27.1 (5)
O12—Ce1—O8—N4	39.0 (3)	C14—C13—C22—C21	−2.2 (6)
O5—Ce1—O8—N4	−130.3 (3)	O2—C13—C22—C21	178.3 (4)
O2—Ce1—O8—N4	121.6 (3)	C14—C13—C22—O4	176.9 (4)
O4—Ce1—O8—N4	62.7 (4)	O2—C13—C22—O4	−2.6 (5)
O10—N4—O9—Ce1	168.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H1···O5^i	0.83	2.17	2.841 (5)	138
O14—H2···O10^ii	0.86	1.95	2.811 (6)	178
C14—H14···N6	0.93	2.60	3.505 (9)	164

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z.