Tris(guanidinium) tris­(pyridine-2,6-dicarboxyl­ato-κ³O,N,O)cerate(III) trihydrate

The nine-coordinate cerium(III) complex with guanidinium as cation, (CH₆N₃)₃[Ce(C₇H₃NO₄)₃]·3H₂O or (GH)₃[Ce(pydc)₃]·3H₂O (G = guanidine and pydc = pyridine-2,6-dicarboxyl­ate), shows a tricapped trigonal-prismatic coordination. Hydrogen-bonding inter­actions between the cation, anion and water mol­ecules result in a three-dimensional supra­molecular network structure.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.087
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2WB   ..  H5B     ..       2.07 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ce1    -   O1      ..       6.32 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ce1    -   O5      ..       5.70 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ce1    -   O7      ..       6.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ce1    -   O9      ..       6.77 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ce1    -   N3      ..       5.71 su
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C12    -   C14    ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C19    -   C21    ...       1.53 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4B    ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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.

Tris(guanidinium) tris(pyridine-2,6-dicarboxylato-κ³O,N,O)cerate(III) trihydrate

Crystal data

(CH6N3)3[Ce(C7H3NO4)3]·3H2O	F(000) = 3512
Mr = 869.74	Dx = 1.723 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1024 reflections
a = 19.0405 (7) Å	θ = 2.2–29.9°
b = 17.1308 (7) Å	µ = 1.45 mm^−1
c = 20.5597 (8) Å	T = 120 K
V = 6706.1 (5) Å^3	Prism, red
Z = 8	0.34 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	7688 independent reflections
Radiation source: fine-focus sealed tube	4221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −20→24
Tmin = 0.639, Tmax = 0.761	k = −22→20
50286 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0245P)^2 + 5.255P] where P = (Fo^2 + 2Fc^2)/3
7688 reflections	(Δ/σ)max = 0.003
469 parameters	Δρmax = 1.21 e Å^−3
159 restraints	Δρmin = −0.66 e Å^−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
Ce1	0.499586 (12)	0.503779 (9)	0.749149 (9)	0.01200 (6)
O1	0.53471 (15)	0.39462 (15)	0.67103 (12)	0.0243 (6)
O2	0.60950 (15)	0.34582 (16)	0.59744 (13)	0.0284 (7)
O3	0.58474 (15)	0.60196 (15)	0.79313 (13)	0.0256 (6)
O4	0.69320 (15)	0.64131 (17)	0.81889 (14)	0.0338 (7)
O5	0.55417 (14)	0.43828 (16)	0.84534 (12)	0.0254 (6)
O6	0.54119 (14)	0.37406 (16)	0.93911 (12)	0.0253 (6)
O7	0.38768 (14)	0.45675 (16)	0.69524 (12)	0.0247 (6)
O8	0.29705 (15)	0.37447 (16)	0.68498 (13)	0.0278 (7)
O9	0.42959 (14)	0.55827 (15)	0.84277 (12)	0.0227 (6)
O10	0.36053 (16)	0.64856 (17)	0.88923 (13)	0.0339 (7)
O11	0.50532 (14)	0.56648 (15)	0.63918 (11)	0.0226 (6)
O12	0.46157 (16)	0.64506 (17)	0.56259 (13)	0.0312 (7)
N1	0.63210 (17)	0.49272 (17)	0.71497 (14)	0.0191 (7)
N2	0.43523 (17)	0.38251 (17)	0.79889 (15)	0.0204 (7)
N3	0.42802 (17)	0.63223 (18)	0.73023 (15)	0.0219 (7)
C1	0.6525 (2)	0.4400 (2)	0.67057 (17)	0.0200 (8)
C2	0.7210 (2)	0.4354 (2)	0.64877 (19)	0.0236 (9)
H2A	0.7339	0.3988	0.6176	0.028*
C3	0.7702 (2)	0.4868 (2)	0.67450 (19)	0.0263 (9)
H3A	0.8166	0.4855	0.6604	0.032*
C4	0.7493 (2)	0.5400 (2)	0.72137 (19)	0.0246 (8)
H4A	0.7817	0.5739	0.7400	0.029*
C5	0.6801 (2)	0.5420 (2)	0.73997 (18)	0.0216 (8)
C6	0.5953 (2)	0.3885 (2)	0.64418 (18)	0.0215 (8)
C7	0.6510 (2)	0.6003 (2)	0.78838 (18)	0.0198 (8)
C8	0.4586 (2)	0.3498 (2)	0.85416 (18)	0.0232 (9)
C9	0.4266 (2)	0.2857 (2)	0.8818 (2)	0.0286 (10)
H9A	0.4425	0.2657	0.9212	0.034*
C10	0.3703 (2)	0.2516 (2)	0.8498 (2)	0.0317 (10)
H10A	0.3495	0.2067	0.8665	0.038*
C11	0.3454 (2)	0.2844 (2)	0.7932 (2)	0.0267 (9)
H11A	0.3075	0.2627	0.7710	0.032*
C12	0.3789 (2)	0.3517 (2)	0.77009 (18)	0.0220 (8)
C13	0.5227 (2)	0.3902 (2)	0.88269 (19)	0.0223 (9)
C14	0.3521 (2)	0.3969 (2)	0.71103 (18)	0.0203 (8)
C15	0.4248 (2)	0.6642 (2)	0.67147 (18)	0.0216 (8)
C16	0.3856 (2)	0.7308 (2)	0.65830 (19)	0.0271 (9)
H16A	0.3835	0.7513	0.6165	0.033*
C17	0.3494 (2)	0.7658 (2)	0.7095 (2)	0.0282 (9)
H17A	0.3235	0.8111	0.7025	0.034*
C18	0.3526 (2)	0.7324 (2)	0.7710 (2)	0.0256 (9)
H18A	0.3289	0.7546	0.8059	0.031*
C19	0.3918 (2)	0.6656 (2)	0.77900 (17)	0.0197 (8)
C20	0.4671 (2)	0.6226 (2)	0.61913 (18)	0.0214 (8)
C21	0.3938 (2)	0.6211 (2)	0.84370 (18)	0.0221 (9)
N7	0.55469 (18)	0.63682 (18)	0.93325 (16)	0.0283 (8)
H7A	0.5500	0.6167	0.9713	0.034*
H7B	0.5796	0.6135	0.9043	0.034*
N8	0.48545 (18)	0.73921 (18)	0.96340 (15)	0.0275 (8)
H8A	0.4809	0.7189	1.0014	0.033*
H8B	0.4651	0.7827	0.9545	0.033*
N9	0.53257 (19)	0.73584 (19)	0.86086 (15)	0.0270 (8)
H9B	0.5135	0.7801	0.8519	0.032*
H9C	0.5576	0.7123	0.8321	0.032*
C23	0.5234 (2)	0.7039 (2)	0.91916 (19)	0.0239 (9)
O2W	0.71557 (17)	0.55637 (18)	0.98229 (15)	0.0423 (8)
H2WA	0.6772	0.5419	1.0007	0.051*
H2WB	0.7106	0.5396	0.9431	0.051*
O3W	0.69337 (15)	0.45249 (16)	0.88277 (13)	0.0301 (7)
H3WB	0.7261	0.4369	0.8570	0.036*
H3WA	0.6507	0.4457	0.8704	0.036*
O1W	0.58721 (16)	0.50024 (16)	1.02614 (14)	0.0340 (7)
H1WA	0.5777	0.4848	1.0649	0.041*
H1WB	0.5867	0.4615	0.9995	0.041*
N4	0.38351 (19)	0.4519 (2)	0.45575 (16)	0.0346 (9)
H4B	0.3443	0.4700	0.4416	0.041*
H4C	0.4136	0.4329	0.4289	0.041*
N5	0.35217 (19)	0.4818 (2)	0.56048 (17)	0.0343 (9)
H5A	0.3616	0.4824	0.6014	0.041*
H5B	0.3128	0.5002	0.5467	0.041*
N6	0.45828 (19)	0.4247 (2)	0.53930 (16)	0.0297 (8)
H6A	0.4684	0.4248	0.5801	0.036*
H6B	0.4877	0.4060	0.5116	0.036*
C22	0.3976 (2)	0.4531 (2)	0.51924 (19)	0.0251 (9)
N10	0.2257 (2)	0.2071 (2)	0.48981 (18)	0.0422 (11)
H10B	0.2449	0.1631	0.4991	0.051*
H10C	0.1997	0.2114	0.4558	0.051*
N11	0.2074 (2)	0.3363 (2)	0.51206 (17)	0.0399 (10)
H11B	0.1820	0.3404	0.4777	0.048*
H11C	0.2142	0.3763	0.5365	0.048*
N12	0.27652 (19)	0.2616 (2)	0.57991 (16)	0.0309 (8)
H12A	0.2957	0.2176	0.5893	0.037*
H12B	0.2834	0.3015	0.6045	0.037*
C24	0.2363 (2)	0.2679 (3)	0.5275 (2)	0.0311 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ce1	0.01043 (9)	0.01541 (9)	0.01016 (9)	−0.00042 (9)	0.00060 (8)	0.00015 (8)
O1	0.0203 (16)	0.0259 (15)	0.0267 (14)	−0.0041 (12)	0.0032 (12)	−0.0041 (11)
O2	0.0305 (18)	0.0278 (16)	0.0269 (15)	−0.0018 (13)	0.0054 (13)	−0.0080 (12)
O3	0.0236 (17)	0.0276 (15)	0.0255 (15)	−0.0046 (12)	0.0010 (12)	−0.0055 (12)
O4	0.0292 (18)	0.0350 (18)	0.0371 (17)	−0.0052 (14)	−0.0043 (14)	−0.0122 (14)
O5	0.0221 (16)	0.0311 (16)	0.0232 (14)	−0.0008 (12)	−0.0021 (12)	0.0046 (12)
O6	0.0244 (17)	0.0322 (16)	0.0194 (13)	−0.0023 (13)	−0.0043 (12)	0.0034 (12)
O7	0.0220 (16)	0.0285 (15)	0.0236 (14)	−0.0044 (12)	−0.0008 (12)	0.0033 (12)
O8	0.0218 (17)	0.0314 (16)	0.0302 (16)	−0.0070 (13)	−0.0098 (13)	0.0030 (12)
O9	0.0243 (16)	0.0228 (14)	0.0208 (13)	0.0005 (12)	0.0024 (11)	0.0005 (11)
O10	0.041 (2)	0.0375 (18)	0.0235 (15)	0.0053 (15)	0.0093 (14)	−0.0005 (13)
O11	0.0292 (17)	0.0220 (13)	0.0165 (12)	0.0034 (12)	0.0019 (12)	0.0027 (10)
O12	0.0363 (19)	0.0363 (17)	0.0210 (14)	0.0071 (14)	0.0043 (13)	0.0049 (12)
N1	0.0182 (17)	0.0221 (17)	0.0172 (16)	−0.0016 (13)	0.0010 (13)	0.0023 (12)
N2	0.0229 (19)	0.0193 (16)	0.0190 (16)	0.0003 (14)	0.0037 (13)	−0.0004 (13)
N3	0.0177 (19)	0.0246 (17)	0.0234 (16)	−0.0015 (14)	0.0012 (13)	0.0005 (13)
C1	0.022 (2)	0.020 (2)	0.0180 (18)	0.0011 (16)	−0.0002 (15)	0.0031 (14)
C2	0.022 (2)	0.026 (2)	0.023 (2)	0.0031 (17)	0.0030 (17)	−0.0037 (16)
C3	0.018 (2)	0.034 (2)	0.027 (2)	−0.0014 (17)	0.0026 (16)	0.0030 (17)
C4	0.021 (2)	0.0224 (19)	0.030 (2)	−0.0042 (18)	−0.0023 (18)	−0.0016 (16)
C5	0.020 (2)	0.0192 (19)	0.026 (2)	−0.0008 (15)	−0.0029 (16)	0.0004 (15)
C6	0.022 (2)	0.021 (2)	0.0210 (19)	0.0015 (16)	−0.0008 (17)	0.0010 (15)
C7	0.020 (2)	0.019 (2)	0.021 (2)	−0.0036 (16)	−0.0012 (16)	0.0029 (15)
C8	0.024 (2)	0.023 (2)	0.023 (2)	0.0029 (17)	0.0007 (16)	0.0018 (16)
C9	0.031 (3)	0.027 (2)	0.028 (2)	−0.0019 (19)	−0.0027 (18)	0.0078 (17)
C10	0.036 (3)	0.026 (2)	0.034 (2)	−0.008 (2)	−0.006 (2)	0.0092 (18)
C11	0.020 (2)	0.028 (2)	0.032 (2)	−0.0055 (18)	−0.0033 (18)	−0.0006 (18)
C12	0.021 (2)	0.020 (2)	0.0249 (19)	−0.0010 (16)	0.0033 (16)	−0.0036 (15)
C13	0.022 (2)	0.021 (2)	0.024 (2)	0.0035 (16)	0.0037 (16)	0.0014 (16)
C14	0.016 (2)	0.025 (2)	0.0203 (19)	−0.0005 (16)	−0.0002 (16)	−0.0015 (15)
C15	0.020 (2)	0.023 (2)	0.0218 (19)	−0.0023 (16)	−0.0010 (16)	0.0018 (15)
C16	0.029 (3)	0.029 (2)	0.023 (2)	−0.0055 (18)	−0.0011 (18)	0.0037 (17)
C17	0.023 (2)	0.029 (2)	0.033 (2)	0.0031 (18)	0.0003 (18)	−0.0004 (18)
C18	0.019 (2)	0.026 (2)	0.032 (2)	−0.0003 (17)	0.0014 (17)	−0.0046 (17)
C19	0.020 (2)	0.022 (2)	0.0170 (18)	−0.0005 (16)	0.0006 (16)	−0.0008 (15)
C20	0.016 (2)	0.025 (2)	0.0231 (19)	−0.0038 (17)	−0.0024 (16)	0.0043 (16)
C21	0.019 (2)	0.027 (2)	0.0203 (19)	−0.0051 (17)	0.0035 (16)	−0.0030 (16)
N7	0.039 (2)	0.0256 (19)	0.0200 (17)	0.0089 (16)	0.0015 (15)	−0.0008 (14)
N8	0.046 (3)	0.0195 (17)	0.0168 (16)	0.0037 (15)	0.0044 (15)	−0.0001 (13)
N9	0.032 (2)	0.0270 (19)	0.0219 (17)	0.0058 (16)	0.0038 (15)	0.0016 (14)
C23	0.026 (2)	0.021 (2)	0.025 (2)	−0.0011 (17)	−0.0047 (17)	−0.0009 (16)
O2W	0.033 (2)	0.049 (2)	0.0451 (19)	−0.0004 (16)	−0.0010 (15)	−0.0155 (16)
O3W	0.0190 (17)	0.0392 (18)	0.0322 (16)	−0.0004 (13)	0.0026 (13)	−0.0038 (13)
O1W	0.043 (2)	0.0356 (18)	0.0239 (14)	−0.0017 (14)	−0.0015 (14)	0.0013 (13)
N4	0.026 (2)	0.054 (3)	0.0242 (18)	0.0114 (18)	0.0002 (15)	0.0060 (17)
N5	0.025 (2)	0.054 (2)	0.0239 (18)	0.0099 (18)	−0.0015 (15)	0.0050 (17)
N6	0.031 (2)	0.038 (2)	0.0208 (17)	0.0095 (17)	0.0002 (16)	−0.0018 (15)
C22	0.023 (2)	0.025 (2)	0.027 (2)	−0.0002 (18)	−0.0001 (17)	0.0064 (17)
N10	0.040 (3)	0.045 (3)	0.041 (2)	0.011 (2)	−0.0155 (19)	−0.0200 (19)
N11	0.044 (3)	0.044 (2)	0.032 (2)	0.011 (2)	−0.0136 (18)	−0.0059 (17)
N12	0.031 (2)	0.033 (2)	0.0288 (19)	0.0029 (16)	−0.0098 (16)	−0.0065 (15)
C24	0.031 (3)	0.042 (3)	0.020 (2)	0.002 (2)	0.0033 (18)	−0.0033 (18)

Geometric parameters (Å, º)

Ce1—O5	2.500 (3)	C12—C14	1.528 (5)
Ce1—O3	2.505 (3)	C15—C16	1.389 (5)
Ce1—O11	2.506 (2)	C15—C20	1.521 (5)
Ce1—O9	2.521 (3)	C16—C17	1.393 (6)
Ce1—O7	2.533 (3)	C16—H16A	0.9300
Ce1—O1	2.554 (3)	C17—C18	1.389 (6)
Ce1—N3	2.617 (3)	C17—H17A	0.9300
Ce1—N2	2.620 (3)	C18—C19	1.376 (5)
Ce1—N1	2.626 (3)	C18—H18A	0.9300
O1—C6	1.283 (5)	C19—C21	1.534 (5)
O2—C6	1.237 (4)	N7—C23	1.327 (5)
O3—C7	1.266 (5)	N7—H7A	0.8600
O4—C7	1.238 (4)	N7—H7B	0.8600
O5—C13	1.276 (4)	N8—C23	1.309 (5)
O6—C13	1.244 (4)	N8—H8A	0.8600
O7—C14	1.272 (4)	N8—H8B	0.8600
O8—C14	1.238 (4)	N9—C23	1.329 (5)
O9—C21	1.274 (4)	N9—H9B	0.8600
O10—C21	1.225 (4)	N9—H9C	0.8600
O11—C20	1.274 (4)	O2W—H2WA	0.8601
O12—C20	1.229 (4)	O2W—H2WB	0.8601
N1—C1	1.342 (5)	O3W—H3WB	0.8600
N1—C5	1.346 (5)	O3W—H3WA	0.8600
N2—C12	1.334 (5)	O1W—H1WA	0.8600
N2—C8	1.343 (5)	O1W—H1WB	0.8600
N3—C15	1.328 (5)	N4—C22	1.333 (5)
N3—C19	1.344 (5)	N4—H4B	0.8600
C1—C2	1.380 (5)	N4—H4C	0.8600
C1—C6	1.503 (5)	N5—C22	1.308 (5)
C2—C3	1.390 (6)	N5—H5A	0.8600
C2—H2A	0.9300	N5—H5B	0.8600
C3—C4	1.384 (6)	N6—C22	1.319 (5)
C3—H3A	0.9300	N6—H6A	0.8600
C4—C5	1.371 (5)	N6—H6B	0.8600
C4—H4A	0.9300	N10—C24	1.314 (5)
C5—C7	1.515 (5)	N10—H10B	0.8600
C8—C9	1.378 (5)	N10—H10C	0.8600
C8—C13	1.521 (6)	N11—C24	1.332 (6)
C9—C10	1.387 (6)	N11—H11B	0.8600
C9—H9A	0.9300	N11—H11C	0.8600
C10—C11	1.378 (6)	N12—C24	1.326 (5)
C10—H10A	0.9300	N12—H12A	0.8600
C11—C12	1.400 (5)	N12—H12B	0.8600
C11—H11A	0.9300
O5—Ce1—O3	75.33 (9)	C10—C9—H9A	120.6
O5—Ce1—O11	152.63 (9)	C11—C10—C9	119.7 (4)
O3—Ce1—O11	90.55 (9)	C11—C10—H10A	120.2
O5—Ce1—O9	77.41 (9)	C9—C10—H10A	120.2
O3—Ce1—O9	79.51 (9)	C10—C11—C12	117.7 (4)
O11—Ce1—O9	123.61 (8)	C10—C11—H11A	121.1
O5—Ce1—O7	123.58 (9)	C12—C11—H11A	121.1
O3—Ce1—O7	156.32 (9)	N2—C12—C11	122.8 (4)
O11—Ce1—O7	77.18 (9)	N2—C12—C14	114.9 (3)
O9—Ce1—O7	90.41 (9)	C11—C12—C14	122.3 (4)
O5—Ce1—O1	93.44 (9)	O6—C13—O5	124.9 (4)
O3—Ce1—O1	123.30 (9)	O6—C13—C8	119.1 (3)
O11—Ce1—O1	74.63 (8)	O5—C13—C8	116.0 (3)
O9—Ce1—O1	152.85 (9)	O8—C14—O7	126.2 (4)
O7—Ce1—O1	73.28 (9)	O8—C14—C12	118.0 (3)
O5—Ce1—N3	135.35 (9)	O7—C14—C12	115.7 (3)
O3—Ce1—N3	79.99 (10)	N3—C15—C16	122.7 (4)
O11—Ce1—N3	61.85 (9)	N3—C15—C20	115.2 (3)
O9—Ce1—N3	61.76 (9)	C16—C15—C20	122.1 (3)
O7—Ce1—N3	76.38 (9)	C15—C16—C17	118.2 (4)
O1—Ce1—N3	131.18 (9)	C15—C16—H16A	120.9
O5—Ce1—N2	61.95 (9)	C17—C16—H16A	120.9
O3—Ce1—N2	133.97 (9)	C18—C17—C16	119.2 (4)
O11—Ce1—N2	135.45 (9)	C18—C17—H17A	120.4
O9—Ce1—N2	75.42 (9)	C16—C17—H17A	120.4
O7—Ce1—N2	61.66 (9)	C19—C18—C17	118.4 (4)
O1—Ce1—N2	77.73 (9)	C19—C18—H18A	120.8
N3—Ce1—N2	118.76 (10)	C17—C18—H18A	120.8
O5—Ce1—N1	77.28 (9)	N3—C19—C18	122.8 (4)
O3—Ce1—N1	61.52 (9)	N3—C19—C21	115.0 (3)
O11—Ce1—N1	75.38 (9)	C18—C19—C21	122.1 (3)
O9—Ce1—N1	137.66 (9)	O12—C20—O11	126.2 (4)
O7—Ce1—N1	131.92 (9)	O12—C20—C15	118.5 (4)
O1—Ce1—N1	61.79 (9)	O11—C20—C15	115.3 (3)
N3—Ce1—N1	121.41 (10)	O10—C21—O9	127.8 (4)
N2—Ce1—N1	119.78 (10)	O10—C21—C19	117.3 (4)
C6—O1—Ce1	124.4 (2)	O9—C21—C19	114.8 (3)
C7—O3—Ce1	127.0 (2)	C23—N7—H7A	120.0
C13—O5—Ce1	124.8 (3)	C23—N7—H7B	120.0
C14—O7—Ce1	126.4 (2)	H7A—N7—H7B	120.0
C21—O9—Ce1	127.4 (2)	C23—N8—H8A	120.0
C20—O11—Ce1	126.2 (2)	C23—N8—H8B	120.0
C1—N1—C5	119.0 (3)	H8A—N8—H8B	120.0
C1—N1—Ce1	120.6 (2)	C23—N9—H9B	120.0
C5—N1—Ce1	120.4 (2)	C23—N9—H9C	120.0
C12—N2—C8	118.4 (3)	H9B—N9—H9C	120.0
C12—N2—Ce1	121.1 (2)	N8—C23—N7	119.7 (4)
C8—N2—Ce1	120.4 (3)	N8—C23—N9	120.6 (4)
C15—N3—C19	118.7 (3)	N7—C23—N9	119.6 (4)
C15—N3—Ce1	120.4 (3)	H2WA—O2W—H2WB	102.8
C19—N3—Ce1	120.9 (2)	H3WB—O3W—H3WA	117.4
N1—C1—C2	122.2 (4)	H1WA—O1W—H1WB	110.6
N1—C1—C6	115.5 (3)	C22—N4—H4B	120.0
C2—C1—C6	122.2 (3)	C22—N4—H4C	120.0
C1—C2—C3	118.4 (4)	H4B—N4—H4C	120.0
C1—C2—H2A	120.8	C22—N5—H5A	120.0
C3—C2—H2A	120.8	C22—N5—H5B	120.0
C4—C3—C2	119.2 (4)	H5A—N5—H5B	120.0
C4—C3—H3A	120.4	C22—N6—H6A	120.0
C2—C3—H3A	120.4	C22—N6—H6B	120.0
C5—C4—C3	119.1 (4)	H6A—N6—H6B	120.0
C5—C4—H4A	120.4	N5—C22—N6	121.0 (4)
C3—C4—H4A	120.4	N5—C22—N4	120.5 (4)
N1—C5—C4	122.0 (4)	N6—C22—N4	118.5 (4)
N1—C5—C7	114.5 (3)	C24—N10—H10B	120.0
C4—C5—C7	123.4 (3)	C24—N10—H10C	120.0
O2—C6—O1	125.4 (4)	H10B—N10—H10C	120.0
O2—C6—C1	117.9 (4)	C24—N11—H11B	120.0
O1—C6—C1	116.7 (3)	C24—N11—H11C	120.0
O4—C7—O3	126.5 (4)	H11B—N11—H11C	120.0
O4—C7—C5	118.0 (4)	C24—N12—H12A	120.0
O3—C7—C5	115.5 (3)	C24—N12—H12B	120.0
N2—C8—C9	122.4 (4)	H12A—N12—H12B	120.0
N2—C8—C13	113.7 (3)	N10—C24—N12	120.2 (4)
C9—C8—C13	123.9 (4)	N10—C24—N11	119.6 (4)
C8—C9—C10	118.8 (4)	N12—C24—N11	120.2 (4)
C8—C9—H9A	120.6
O5—Ce1—O1—C6	−82.7 (3)	N1—Ce1—N3—C15	53.9 (3)
O3—Ce1—O1—C6	−8.0 (3)	O5—Ce1—N3—C19	−23.9 (3)
O11—Ce1—O1—C6	72.3 (3)	O3—Ce1—N3—C19	−80.9 (3)
O9—Ce1—O1—C6	−151.5 (3)	O11—Ce1—N3—C19	−177.0 (3)
O7—Ce1—O1—C6	153.2 (3)	O9—Ce1—N3—C19	2.5 (3)
N3—Ce1—O1—C6	99.3 (3)	O7—Ce1—N3—C19	100.5 (3)
N2—Ce1—O1—C6	−143.1 (3)	O1—Ce1—N3—C19	153.2 (3)
N1—Ce1—O1—C6	−9.1 (3)	N2—Ce1—N3—C19	54.1 (3)
O5—Ce1—O3—C7	74.1 (3)	N1—Ce1—N3—C19	−128.4 (3)
O11—Ce1—O3—C7	−82.1 (3)	C5—N1—C1—C2	−1.1 (5)
O9—Ce1—O3—C7	153.7 (3)	Ce1—N1—C1—C2	176.3 (3)
O7—Ce1—O3—C7	−140.1 (3)	C5—N1—C1—C6	−178.8 (3)
O1—Ce1—O3—C7	−10.3 (3)	Ce1—N1—C1—C6	−1.3 (4)
N3—Ce1—O3—C7	−143.4 (3)	N1—C1—C2—C3	0.7 (6)
N2—Ce1—O3—C7	96.0 (3)	C6—C1—C2—C3	178.2 (3)
N1—Ce1—O3—C7	−9.1 (3)	C1—C2—C3—C4	0.8 (6)
O3—Ce1—O5—C13	146.8 (3)	C2—C3—C4—C5	−1.7 (6)
O11—Ce1—O5—C13	−152.1 (3)	C1—N1—C5—C4	0.1 (5)
O9—Ce1—O5—C13	64.5 (3)	Ce1—N1—C5—C4	−177.4 (3)
O7—Ce1—O5—C13	−17.5 (3)	C1—N1—C5—C7	178.6 (3)
O1—Ce1—O5—C13	−89.6 (3)	Ce1—N1—C5—C7	1.1 (4)
N3—Ce1—O5—C13	88.2 (3)	C3—C4—C5—N1	1.3 (6)
N2—Ce1—O5—C13	−15.5 (3)	C3—C4—C5—C7	−177.0 (4)
N1—Ce1—O5—C13	−149.7 (3)	Ce1—O1—C6—O2	−165.4 (3)
O5—Ce1—O7—C14	−1.8 (3)	Ce1—O1—C6—C1	12.2 (4)
O3—Ce1—O7—C14	−141.0 (3)	N1—C1—C6—O2	171.1 (3)
O11—Ce1—O7—C14	158.6 (3)	C2—C1—C6—O2	−6.5 (6)
O9—Ce1—O7—C14	−76.9 (3)	N1—C1—C6—O1	−6.7 (5)
O1—Ce1—O7—C14	81.0 (3)	C2—C1—C6—O1	175.7 (4)
N3—Ce1—O7—C14	−137.7 (3)	Ce1—O3—C7—O4	−167.2 (3)
N2—Ce1—O7—C14	−3.8 (3)	Ce1—O3—C7—C5	13.1 (4)
N1—Ce1—O7—C14	102.1 (3)	N1—C5—C7—O4	171.8 (3)
O5—Ce1—O9—C21	158.6 (3)	C4—C5—C7—O4	−9.7 (6)
O3—Ce1—O9—C21	81.5 (3)	N1—C5—C7—O3	−8.4 (5)
O11—Ce1—O9—C21	−2.1 (3)	C4—C5—C7—O3	170.0 (4)
O7—Ce1—O9—C21	−77.0 (3)	C12—N2—C8—C9	0.2 (6)
O1—Ce1—O9—C21	−128.9 (3)	Ce1—N2—C8—C9	−179.6 (3)
N3—Ce1—O9—C21	−2.7 (3)	C12—N2—C8—C13	−179.6 (3)
N2—Ce1—O9—C21	−137.5 (3)	Ce1—N2—C8—C13	0.6 (4)
N1—Ce1—O9—C21	104.1 (3)	N2—C8—C9—C10	3.1 (6)
O5—Ce1—O11—C20	−146.0 (3)	C13—C8—C9—C10	−177.1 (4)
O3—Ce1—O11—C20	−88.2 (3)	C8—C9—C10—C11	−3.3 (7)
O9—Ce1—O11—C20	−10.4 (3)	C9—C10—C11—C12	0.3 (6)
O7—Ce1—O11—C20	71.4 (3)	C8—N2—C12—C11	−3.3 (6)
O1—Ce1—O11—C20	147.3 (3)	Ce1—N2—C12—C11	176.5 (3)
N3—Ce1—O11—C20	−9.8 (3)	C8—N2—C12—C14	174.7 (3)
N2—Ce1—O11—C20	93.7 (3)	Ce1—N2—C12—C14	−5.5 (4)
N1—Ce1—O11—C20	−148.5 (3)	C10—C11—C12—N2	3.1 (6)
O5—Ce1—N1—C1	105.7 (3)	C10—C11—C12—C14	−174.9 (4)
O3—Ce1—N1—C1	−174.2 (3)	Ce1—O5—C13—O6	−159.1 (3)
O11—Ce1—N1—C1	−75.4 (3)	Ce1—O5—C13—C8	21.9 (5)
O9—Ce1—N1—C1	160.3 (2)	N2—C8—C13—O6	167.3 (3)
O7—Ce1—N1—C1	−18.3 (3)	C9—C8—C13—O6	−12.5 (6)
O1—Ce1—N1—C1	4.7 (2)	N2—C8—C13—O5	−13.6 (5)
N3—Ce1—N1—C1	−118.5 (3)	C9—C8—C13—O5	166.6 (4)
N2—Ce1—N1—C1	58.9 (3)	Ce1—O7—C14—O8	179.2 (3)
O5—Ce1—N1—C5	−76.8 (3)	Ce1—O7—C14—C12	2.6 (5)
O3—Ce1—N1—C5	3.2 (2)	N2—C12—C14—O8	−174.9 (3)
O11—Ce1—N1—C5	102.0 (3)	C11—C12—C14—O8	3.2 (6)
O9—Ce1—N1—C5	−22.2 (3)	N2—C12—C14—O7	2.1 (5)
O7—Ce1—N1—C5	159.2 (2)	C11—C12—C14—O7	−179.9 (4)
O1—Ce1—N1—C5	−177.8 (3)	C19—N3—C15—C16	0.0 (6)
N3—Ce1—N1—C5	59.0 (3)	Ce1—N3—C15—C16	177.7 (3)
N2—Ce1—N1—C5	−123.6 (3)	C19—N3—C15—C20	−179.8 (3)
O5—Ce1—N2—C12	−173.4 (3)	Ce1—N3—C15—C20	−2.1 (4)
O3—Ce1—N2—C12	162.5 (3)	N3—C15—C16—C17	1.3 (6)
O11—Ce1—N2—C12	−20.1 (3)	C20—C15—C16—C17	−178.9 (4)
O9—Ce1—N2—C12	103.3 (3)	C15—C16—C17—C18	−1.4 (6)
O7—Ce1—N2—C12	4.8 (3)	C16—C17—C18—C19	0.2 (6)
O1—Ce1—N2—C12	−72.7 (3)	C15—N3—C19—C18	−1.3 (6)
N3—Ce1—N2—C12	57.8 (3)	Ce1—N3—C19—C18	−179.0 (3)
N1—Ce1—N2—C12	−119.7 (3)	C15—N3—C19—C21	175.3 (3)
O5—Ce1—N2—C8	6.4 (3)	Ce1—N3—C19—C21	−2.4 (4)
O3—Ce1—N2—C8	−17.7 (3)	C17—C18—C19—N3	1.2 (6)
O11—Ce1—N2—C8	159.7 (2)	C17—C18—C19—C21	−175.1 (4)
O9—Ce1—N2—C8	−76.9 (3)	Ce1—O11—C20—O12	−167.3 (3)
O7—Ce1—N2—C8	−175.5 (3)	Ce1—O11—C20—C15	12.5 (5)
O1—Ce1—N2—C8	107.1 (3)	N3—C15—C20—O12	173.7 (4)
N3—Ce1—N2—C8	−122.4 (3)	C16—C15—C20—O12	−6.1 (6)
N1—Ce1—N2—C8	60.1 (3)	N3—C15—C20—O11	−6.0 (5)
O5—Ce1—N3—C15	158.5 (3)	C16—C15—C20—O11	174.2 (4)
O3—Ce1—N3—C15	101.5 (3)	Ce1—O9—C21—O10	−178.8 (3)
O11—Ce1—N3—C15	5.4 (3)	Ce1—O9—C21—C19	2.6 (5)
O9—Ce1—N3—C15	−175.1 (3)	N3—C19—C21—O10	−178.7 (4)
O7—Ce1—N3—C15	−77.2 (3)	C18—C19—C21—O10	−2.1 (6)
O1—Ce1—N3—C15	−24.4 (3)	N3—C19—C21—O9	0.1 (5)
N2—Ce1—N3—C15	−123.5 (3)	C18—C19—C21—O9	176.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WA···O1W	0.86	1.93	2.777 (4)	169
O2W—H2WB···O3W	0.86	1.97	2.744 (4)	149
O3W—H3WB···O8^i	0.86	1.93	2.761 (4)	163
O3W—H3WA···O5	0.86	1.91	2.771 (4)	176
N4—H4C···O11^ii	0.86	2.08	2.896 (4)	157
O1W—H1WA···O9^iii	0.86	2.04	2.893 (4)	171
N5—H5A···O7	0.86	2.04	2.884 (4)	167
N5—H5B···O2W^iv	0.86	2.17	3.028 (5)	174
O1W—H1WB···O6	0.86	2.13	2.940 (4)	157
N6—H6A···O1	0.86	2.31	3.117 (4)	155
N6—H6B···O12^ii	0.86	2.01	2.854 (4)	168
N7—H7A···O1W	0.86	2.40	3.083 (4)	137
N7—H7A···O6^iii	0.86	2.54	3.202 (4)	135
N7—H7B···O3	0.86	2.30	2.997 (4)	139
N8—H8A···O6^iii	0.86	2.05	2.835 (4)	151
N8—H8B···O2^v	0.86	2.08	2.858 (4)	150
N9—H9B···O1^v	0.86	2.22	3.077 (4)	179
N9—H9C···O3	0.86	2.12	2.861 (4)	145
N10—H10B···O2W^vi	0.86	2.01	2.872 (5)	176
N10—H10C···O2^vii	0.86	2.26	2.989 (5)	143
N11—H11B···O10^viii	0.86	2.00	2.849 (5)	170
N11—H11C···O3W^iv	0.86	2.15	2.951 (4)	155
N12—H12A···O4^vi	0.86	2.31	2.985 (4)	136
N12—H12B···O8	0.86	2.09	2.925 (4)	164
C3—H3A···O9^i	0.93	2.49	3.296 (4)	145
C17—H17A···O8^ix	0.93	2.56	3.390 (5)	148

Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x−1/2, y, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x−1/2, −y+1/2, −z+1; (viii) −x+1/2, −y+1, z−1/2; (ix) −x+1/2, y+1/2, z.