Bis(2,6-dihy-droxy-benzoato-κO,O)(nitrato-κO,O')bis-(1,10-phenanthroline-κN,N')cerium(III).

The mononuclear title complex, [Ce(C(7)H(5)O(3))(2)(NO(3))(C(12)H(8)N(2))(2)], is isostructural to other related lanthanide structures. The Ce atom is in a pseudo-bicapped square-anti-prismatic geometry formed by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and by six O atoms, four from two 2,6-dihy-droxy-benzoate (DHB) ligands and the other two from a nitrate anion. π-π stacking inter-actions between phen and DHB ligands [centroid-centroid distances = 3.513 (3) and 3.762 (2) Å] and phen and phen ligands [face-to-face separation = 3.423 (7) Å] of adjacent complexes stabilize the crystal structure. Intra-molecular O-H⋯O hydrogen bonds are observed in the DHB ligands.

Related literature

For background and a related structure, see: Zheng et al. (2010 ▶).

Experimental

Crystal data

[Ce(C7H5O3)2(NO3)(C12H8N2)2]

M = 868.76

Monoclinic,

a = 11.2937 (2) Å

b = 26.7878 (3) Å

c = 14.4056 (4) Å

β = 128.062 (2)°

V = 3431.38 (12) Å3

Z = 4

Cu Kα radiation

μ = 10.88 mm−1

T = 298 K

0.40 × 0.35 × 0.32 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (ABSPACK in CrysAlis PRO RED; Oxford Diffraction, 2006 ▶) T min = 0.098, T max = 0.128

11880 measured reflections

6060 independent reflections

5705 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.108

S = 1.08

6060 reflections

496 parameters

H-atom parameters constrained

Δρmax = 1.60 e Å−3

Δρmin = −2.34 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049755/kj2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049755/kj2166Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ce(C7H8O3)2(NO3)(C12H8N2)2]	F(000) = 1740
Mr = 868.76	Dx = 1.682 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7834 reflections
a = 11.2937 (2) Å	θ = 3.3–67.5°
b = 26.7878 (3) Å	µ = 10.88 mm−1
c = 14.4056 (4) Å	T = 298 K
β = 128.062 (2)°	Prism, orange
V = 3431.38 (12) Å3	0.40 × 0.35 × 0.32 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	6060 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	5705 reflections with I > 2σ(I)
mirror	Rint = 0.040
Detector resolution: 15.9149 pixels mm-1	θmax = 67.6°, θmin = 3.3°
ω scans	h = −13→9
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO RED; Oxford Diffraction, 2006)	k = −31→30
Tmin = 0.098, Tmax = 0.128	l = −15→17
11880 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3
6060 reflections	(Δ/σ)max = 0.001
496 parameters	Δρmax = 1.60 e Å−3
0 restraints	Δρmin = −2.34 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ce1	0.06777 (2)	0.860990 (6)	0.281182 (15)	0.02790 (10)
O1	0.1127 (3)	0.91826 (10)	0.4477 (2)	0.0425 (6)
O2	0.1553 (3)	0.83834 (11)	0.4866 (2)	0.0433 (6)
O3	0.1667 (6)	0.97993 (13)	0.6076 (3)	0.0836 (14)
H27	0.1539	0.9716	0.5472	0.125*
O4	0.2409 (4)	0.80338 (11)	0.6866 (3)	0.0577 (8)
H31	0.2097	0.8022	0.6180	0.087*
O5	0.3411 (3)	0.89154 (12)	0.4052 (3)	0.0522 (7)
O6	0.3093 (3)	0.81036 (10)	0.3702 (3)	0.0423 (6)
O7	0.5838 (4)	0.93411 (14)	0.4708 (4)	0.0707 (10)
H34	0.4990	0.9315	0.4516	0.106*
O8	0.5206 (3)	0.75680 (11)	0.4002 (3)	0.0509 (7)
H38	0.4367	0.7631	0.3803	0.076*
O9	0.0371 (3)	0.79921 (10)	0.1255 (2)	0.0446 (6)
O10	0.1491 (4)	0.86854 (12)	0.1482 (3)	0.0517 (8)
O11	0.1299 (5)	0.8118 (2)	0.0329 (3)	0.0872 (14)
N1	−0.1724 (3)	0.88310 (11)	0.0578 (3)	0.0342 (6)
N2	0.0218 (4)	0.95609 (12)	0.2074 (3)	0.0362 (6)
N3	−0.1909 (4)	0.86488 (11)	0.2506 (3)	0.0354 (7)
N4	−0.0654 (3)	0.77638 (11)	0.2624 (3)	0.0341 (6)
N5	0.1050 (4)	0.82562 (15)	0.1000 (3)	0.0447 (8)
C1	−0.2693 (5)	0.84828 (16)	−0.0142 (4)	0.0396 (8)
H1	−0.2589	0.8167	0.0167	0.048*
C2	−0.3867 (5)	0.85607 (16)	−0.1341 (4)	0.0446 (10)
H2	−0.4520	0.8303	−0.1813	0.053*
C3	−0.4029 (4)	0.90275 (19)	−0.1799 (4)	0.0471 (9)
H3A	−0.4789	0.9090	−0.2595	0.056*
C4	−0.3037 (4)	0.94091 (15)	−0.1058 (3)	0.0380 (8)
C5	−0.1891 (4)	0.92953 (14)	0.0138 (3)	0.0321 (7)
C6	−0.0870 (4)	0.96814 (13)	0.0922 (3)	0.0325 (7)
C7	−0.1023 (5)	1.01658 (14)	0.0469 (4)	0.0405 (8)
C8	−0.2192 (5)	1.02677 (16)	−0.0747 (4)	0.0476 (10)
H8A	−0.2291	1.0588	−0.1039	0.057*
C9	−0.3150 (5)	0.99073 (17)	−0.1476 (4)	0.0484 (10)
H9	−0.3902	0.9982	−0.2267	0.058*
C10	0.0007 (5)	1.05311 (14)	0.1265 (4)	0.0478 (10)
H10	−0.0055	1.0855	0.1006	0.057*
C11	0.1098 (6)	1.04083 (16)	0.2420 (4)	0.0528 (11)
H11	0.1790	1.0646	0.2953	0.063*
C12	0.1157 (5)	0.99191 (15)	0.2789 (4)	0.0450 (9)
H12	0.1896	0.9841	0.3579	0.054*
C13	−0.2486 (5)	0.90824 (16)	0.2494 (4)	0.0463 (9)
H13	−0.1893	0.9368	0.2743	0.056*
C14	−0.3965 (6)	0.9125 (2)	0.2118 (4)	0.0578 (12)
H14	−0.4343	0.9434	0.2113	0.069*
C15	−0.4844 (5)	0.8705 (2)	0.1758 (4)	0.0572 (12)
H15	−0.5830	0.8728	0.1493	0.069*
C16	−0.4252 (4)	0.82424 (19)	0.1790 (3)	0.0449 (10)
C17	−0.2750 (4)	0.82332 (15)	0.2188 (3)	0.0354 (8)
C18	−0.2060 (4)	0.77609 (13)	0.2295 (3)	0.0329 (7)
C19	−0.2887 (5)	0.73159 (16)	0.2044 (3)	0.0420 (9)
C20	−0.4416 (5)	0.7343 (2)	0.1603 (4)	0.0522 (11)
H20	−0.4970	0.7050	0.1401	0.063*
C21	−0.5061 (5)	0.7781 (2)	0.1478 (4)	0.0564 (12)
H21	−0.6062	0.7788	0.1181	0.068*
C22	−0.2121 (6)	0.68653 (15)	0.2236 (4)	0.0489 (10)
H22	−0.2602	0.6562	0.2109	0.059*
C23	−0.0695 (5)	0.68692 (15)	0.2604 (4)	0.0469 (10)
H23	−0.0184	0.6572	0.2746	0.056*
C24	0.0003 (5)	0.73284 (15)	0.2768 (4)	0.0422 (8)
H24	0.0968	0.7329	0.2987	0.051*
C25	0.1543 (4)	0.88195 (14)	0.5192 (3)	0.0353 (8)
C26	0.2017 (4)	0.89119 (15)	0.6388 (3)	0.0340 (7)
C27	0.2065 (5)	0.93979 (17)	0.6772 (4)	0.0492 (10)
C28	0.2552 (7)	0.9477 (2)	0.7912 (4)	0.0652 (14)
H28	0.2598	0.9800	0.8172	0.078*
C29	0.2965 (6)	0.9078 (2)	0.8657 (4)	0.0611 (13)
H29	0.3291	0.9135	0.9419	0.073*
C30	0.2907 (6)	0.86001 (18)	0.8302 (4)	0.0513 (12)
H30	0.3188	0.8336	0.8819	0.062*
C31	0.2426 (4)	0.85087 (16)	0.7164 (4)	0.0408 (8)
C32	0.3909 (4)	0.84926 (16)	0.4017 (3)	0.0384 (8)
C33	0.5425 (4)	0.84581 (16)	0.4348 (3)	0.0379 (8)
C34	0.6332 (5)	0.88857 (18)	0.4675 (4)	0.0475 (9)
C35	0.7760 (5)	0.8846 (2)	0.4980 (4)	0.0577 (12)
H35	0.8362	0.9128	0.5208	0.069*
C36	0.8279 (5)	0.8391 (2)	0.4945 (4)	0.0568 (12)
H36	0.9235	0.8369	0.5149	0.068*
C37	0.7431 (4)	0.7963 (2)	0.4617 (3)	0.0480 (10)
H37	0.7809	0.7658	0.4595	0.058*
C38	0.6000 (4)	0.79916 (16)	0.4319 (3)	0.0396 (8)

	U11	U22	U33	U12	U13	U23
Ce1	0.03329 (14)	0.02207 (14)	0.03061 (13)	−0.00013 (6)	0.02084 (11)	0.00019 (6)
O1	0.0571 (16)	0.0358 (14)	0.0328 (12)	0.0013 (12)	0.0268 (12)	0.0006 (11)
O2	0.0552 (16)	0.0328 (14)	0.0348 (13)	0.0032 (12)	0.0243 (13)	−0.0010 (11)
O3	0.155 (4)	0.0357 (17)	0.0533 (19)	0.018 (2)	0.061 (2)	0.0030 (15)
O4	0.071 (2)	0.0396 (16)	0.0427 (15)	0.0006 (15)	0.0248 (15)	0.0059 (13)
O5	0.0419 (15)	0.0422 (16)	0.0652 (19)	−0.0031 (13)	0.0292 (15)	−0.0107 (14)
O6	0.0371 (13)	0.0362 (14)	0.0524 (15)	0.0002 (11)	0.0269 (12)	0.0002 (12)
O7	0.060 (2)	0.050 (2)	0.089 (3)	−0.0172 (16)	0.039 (2)	−0.0139 (19)
O8	0.0469 (15)	0.0449 (16)	0.0638 (18)	0.0011 (13)	0.0356 (15)	−0.0065 (14)
O9	0.0541 (15)	0.0362 (14)	0.0480 (14)	−0.0011 (12)	0.0337 (14)	−0.0065 (12)
O10	0.069 (2)	0.0459 (16)	0.0618 (19)	−0.0031 (15)	0.0515 (18)	0.0067 (15)
O11	0.087 (3)	0.142 (4)	0.055 (2)	0.003 (3)	0.055 (2)	−0.018 (2)
N1	0.0439 (17)	0.0282 (15)	0.0355 (14)	−0.0033 (13)	0.0270 (14)	−0.0010 (12)
N2	0.0445 (16)	0.0283 (15)	0.0377 (15)	0.0010 (13)	0.0263 (14)	−0.0028 (12)
N3	0.0368 (16)	0.0366 (17)	0.0331 (15)	0.0063 (12)	0.0216 (14)	0.0054 (12)
N4	0.0441 (16)	0.0253 (15)	0.0351 (14)	0.0003 (12)	0.0255 (14)	0.0020 (11)
N5	0.0445 (17)	0.058 (2)	0.0342 (15)	0.0082 (16)	0.0258 (15)	0.0003 (15)
C1	0.045 (2)	0.0372 (19)	0.0387 (19)	−0.0080 (17)	0.0266 (18)	−0.0042 (17)
C2	0.039 (2)	0.052 (2)	0.040 (2)	−0.0063 (17)	0.0227 (19)	−0.0066 (17)
C3	0.0362 (19)	0.061 (3)	0.0392 (19)	0.0042 (18)	0.0208 (17)	0.0043 (19)
C4	0.0366 (18)	0.044 (2)	0.0387 (18)	0.0101 (16)	0.0260 (16)	0.0108 (16)
C5	0.0366 (17)	0.0326 (18)	0.0377 (17)	0.0054 (14)	0.0282 (16)	0.0035 (14)
C6	0.0433 (18)	0.0253 (16)	0.0407 (17)	0.0054 (14)	0.0318 (16)	0.0022 (14)
C7	0.058 (2)	0.0264 (17)	0.060 (2)	0.0103 (16)	0.047 (2)	0.0067 (16)
C8	0.062 (3)	0.035 (2)	0.061 (2)	0.0200 (19)	0.046 (2)	0.0211 (19)
C9	0.053 (2)	0.050 (2)	0.049 (2)	0.021 (2)	0.035 (2)	0.020 (2)
C10	0.073 (3)	0.0211 (17)	0.073 (3)	0.0036 (17)	0.057 (3)	0.0013 (17)
C11	0.073 (3)	0.030 (2)	0.068 (3)	−0.014 (2)	0.050 (3)	−0.0136 (19)
C12	0.058 (2)	0.031 (2)	0.046 (2)	−0.0080 (18)	0.033 (2)	−0.0073 (17)
C13	0.054 (2)	0.041 (2)	0.050 (2)	0.0111 (19)	0.036 (2)	0.0040 (18)
C14	0.058 (3)	0.066 (3)	0.054 (2)	0.030 (2)	0.037 (2)	0.013 (2)
C15	0.040 (2)	0.087 (3)	0.044 (2)	0.015 (2)	0.026 (2)	0.009 (2)
C16	0.0387 (19)	0.069 (3)	0.0300 (16)	0.0064 (19)	0.0225 (16)	0.0066 (18)
C17	0.0358 (17)	0.046 (2)	0.0252 (14)	0.0025 (16)	0.0190 (14)	0.0045 (14)
C18	0.0420 (18)	0.0345 (18)	0.0253 (14)	−0.0063 (15)	0.0224 (14)	0.0010 (13)
C19	0.054 (2)	0.047 (2)	0.0298 (16)	−0.0153 (18)	0.0286 (16)	−0.0027 (16)
C20	0.052 (2)	0.066 (3)	0.0388 (19)	−0.020 (2)	0.0280 (19)	−0.004 (2)
C21	0.039 (2)	0.088 (4)	0.039 (2)	−0.015 (2)	0.0225 (18)	−0.002 (2)
C22	0.076 (3)	0.032 (2)	0.042 (2)	−0.0172 (19)	0.038 (2)	−0.0037 (16)
C23	0.072 (3)	0.0269 (18)	0.044 (2)	0.0016 (18)	0.036 (2)	0.0031 (15)
C24	0.051 (2)	0.0301 (18)	0.046 (2)	0.0025 (17)	0.0308 (18)	0.0030 (16)
C25	0.0348 (18)	0.0351 (19)	0.0351 (17)	0.0000 (15)	0.0212 (15)	0.0010 (15)
C26	0.0306 (16)	0.0391 (19)	0.0299 (16)	0.0004 (14)	0.0175 (14)	0.0002 (14)
C27	0.065 (3)	0.044 (2)	0.0381 (19)	0.009 (2)	0.032 (2)	0.0015 (17)
C28	0.092 (4)	0.058 (3)	0.043 (2)	0.017 (3)	0.041 (3)	−0.004 (2)
C29	0.068 (3)	0.080 (4)	0.036 (2)	0.011 (3)	0.032 (2)	−0.001 (2)
C30	0.050 (3)	0.066 (3)	0.036 (2)	0.0043 (19)	0.026 (2)	0.0119 (18)
C31	0.0314 (18)	0.045 (2)	0.0375 (19)	−0.0019 (16)	0.0171 (16)	0.0028 (17)
C32	0.0362 (19)	0.042 (2)	0.0344 (18)	−0.0018 (17)	0.0203 (16)	−0.0038 (16)
C33	0.0344 (18)	0.047 (2)	0.0277 (16)	−0.0036 (17)	0.0170 (15)	−0.0004 (16)
C34	0.042 (2)	0.051 (2)	0.0419 (19)	−0.0078 (18)	0.0217 (18)	−0.0039 (18)
C35	0.046 (2)	0.077 (4)	0.045 (2)	−0.022 (2)	0.026 (2)	−0.005 (2)
C36	0.035 (2)	0.093 (4)	0.040 (2)	−0.003 (2)	0.0222 (18)	0.001 (2)
C37	0.040 (2)	0.070 (3)	0.0339 (17)	0.005 (2)	0.0225 (16)	0.0001 (19)
C38	0.0357 (18)	0.051 (2)	0.0290 (15)	0.0025 (17)	0.0185 (14)	0.0028 (16)

Ce1—O2	2.549 (3)	C9—H9	0.9300
Ce1—O5	2.567 (3)	C10—C11	1.366 (7)
Ce1—O6	2.572 (3)	C10—H10	0.9300
Ce1—O10	2.593 (3)	C11—C12	1.400 (6)
Ce1—O1	2.620 (3)	C11—H11	0.9300
Ce1—O9	2.633 (3)	C12—H12	0.9300
Ce1—N4	2.640 (3)	C13—C14	1.407 (6)
Ce1—N3	2.674 (3)	C13—H13	0.9300
Ce1—N2	2.685 (3)	C14—C15	1.375 (8)
Ce1—N1	2.702 (3)	C14—H14	0.9300
O1—C25	1.277 (5)	C15—C16	1.394 (7)
O2—C25	1.261 (5)	C15—H15	0.9300
O3—C27	1.345 (6)	C16—C17	1.417 (5)
O3—H27	0.8204	C16—C21	1.434 (7)
O4—C31	1.339 (5)	C17—C18	1.443 (5)
O4—H31	0.8200	C18—C19	1.417 (5)
O5—C32	1.279 (5)	C19—C22	1.409 (6)
O6—C32	1.275 (5)	C19—C20	1.428 (6)
O7—C34	1.354 (6)	C20—C21	1.335 (8)
O7—H34	0.8196	C20—H20	0.9300
O8—C38	1.340 (5)	C21—H21	0.9300
O8—H38	0.8207	C22—C23	1.350 (7)
O9—N5	1.253 (5)	C22—H22	0.9300
O10—N5	1.275 (5)	C23—C24	1.400 (6)
O11—N5	1.218 (5)	C23—H23	0.9300
N1—C1	1.320 (5)	C24—H24	0.9300
N1—C5	1.355 (5)	C25—C26	1.476 (5)
N2—C12	1.326 (5)	C26—C27	1.402 (6)
N2—C6	1.362 (5)	C26—C31	1.412 (6)
N3—C13	1.327 (5)	C27—C28	1.390 (6)
N3—C17	1.347 (5)	C28—C29	1.376 (8)
N4—C24	1.328 (5)	C28—H28	0.9300
N4—C18	1.349 (5)	C29—C30	1.366 (7)
C1—C2	1.400 (6)	C29—H29	0.9300
C1—H1	0.9300	C30—C31	1.394 (6)
C2—C3	1.373 (6)	C30—H30	0.9300
C2—H2	0.9300	C32—C33	1.470 (5)
C3—C4	1.402 (6)	C33—C34	1.410 (6)
C3—H3A	0.9300	C33—C38	1.421 (6)
C4—C5	1.409 (5)	C34—C35	1.390 (6)
C4—C9	1.437 (6)	C35—C36	1.367 (8)
C5—C6	1.439 (5)	C35—H35	0.9300
C6—C7	1.414 (5)	C36—C37	1.377 (7)
C7—C10	1.408 (6)	C36—H36	0.9300
C7—C8	1.426 (6)	C37—C38	1.395 (6)
C8—C9	1.344 (7)	C37—H37	0.9300
C8—H8A	0.9300
O2—Ce1—O5	80.14 (10)	C9—C8—H8A	119.6
O2—Ce1—O6	76.28 (9)	C7—C8—H8A	119.6
O5—Ce1—O6	50.97 (9)	C8—C9—C4	121.3 (4)
O2—Ce1—O10	144.69 (11)	C8—C9—H9	119.4
O5—Ce1—O10	70.60 (11)	C4—C9—H9	119.4
O6—Ce1—O10	70.09 (10)	C11—C10—C7	119.8 (4)
O2—Ce1—O1	50.12 (8)	C11—C10—H10	120.1
O5—Ce1—O1	72.83 (10)	C7—C10—H10	120.1
O6—Ce1—O1	107.76 (9)	C10—C11—C12	118.9 (4)
O10—Ce1—O1	132.36 (10)	C10—C11—H11	120.5
O2—Ce1—O9	126.35 (9)	C12—C11—H11	120.5
O5—Ce1—O9	105.27 (9)	N2—C12—C11	123.7 (4)
O6—Ce1—O9	68.60 (9)	N2—C12—H12	118.2
O10—Ce1—O9	48.70 (10)	C11—C12—H12	118.2
O1—Ce1—O9	175.99 (9)	N3—C13—C14	122.2 (4)
O2—Ce1—N4	72.73 (9)	N3—C13—H13	118.9
O5—Ce1—N4	135.20 (10)	C14—C13—H13	118.9
O6—Ce1—N4	87.74 (9)	C15—C14—C13	119.2 (4)
O10—Ce1—N4	115.47 (10)	C15—C14—H14	120.4
O1—Ce1—N4	111.91 (9)	C13—C14—H14	120.4
O9—Ce1—N4	66.78 (9)	C14—C15—C16	119.7 (4)
O2—Ce1—N3	78.62 (10)	C14—C15—H15	120.2
O5—Ce1—N3	145.58 (10)	C16—C15—H15	120.2
O6—Ce1—N3	144.88 (9)	C15—C16—C17	117.3 (4)
O10—Ce1—N3	136.36 (11)	C15—C16—C21	123.7 (4)
O1—Ce1—N3	72.76 (10)	C17—C16—C21	119.0 (4)
O9—Ce1—N3	109.12 (9)	N3—C17—C16	122.7 (4)
N4—Ce1—N3	61.39 (9)	N3—C17—C18	117.9 (3)
O2—Ce1—N2	121.83 (9)	C16—C17—C18	119.4 (4)
O5—Ce1—N2	80.15 (10)	N4—C18—C19	122.8 (4)
O6—Ce1—N2	125.77 (9)	N4—C18—C17	118.2 (3)
O10—Ce1—N2	72.76 (10)	C19—C18—C17	118.9 (3)
O1—Ce1—N2	71.80 (8)	C22—C19—C18	116.3 (4)
O9—Ce1—N2	111.56 (9)	C22—C19—C20	123.9 (4)
N4—Ce1—N2	144.60 (10)	C18—C19—C20	119.8 (4)
N3—Ce1—N2	88.45 (9)	C21—C20—C19	120.9 (4)
O2—Ce1—N1	145.18 (9)	C21—C20—H20	119.5
O5—Ce1—N1	130.72 (10)	C19—C20—H20	119.5
O6—Ce1—N1	133.38 (9)	C20—C21—C16	121.8 (4)
O10—Ce1—N1	69.85 (10)	C20—C21—H21	119.1
O1—Ce1—N1	116.60 (9)	C16—C21—H21	119.1
O9—Ce1—N1	67.35 (9)	C23—C22—C19	120.6 (4)
N4—Ce1—N1	88.63 (9)	C23—C22—H22	119.7
N3—Ce1—N1	66.60 (9)	C19—C22—H22	119.7
N2—Ce1—N1	60.89 (9)	C22—C23—C24	118.9 (4)
C25—O1—Ce1	93.4 (2)	C22—C23—H23	120.5
C25—O2—Ce1	97.2 (2)	C24—C23—H23	120.5
C27—O3—H27	109.4	N4—C24—C23	122.9 (4)
C31—O4—H31	109.5	N4—C24—H24	118.5
C32—O5—Ce1	93.4 (2)	C23—C24—H24	118.5
C32—O6—Ce1	93.3 (2)	O2—C25—O1	119.3 (3)
C34—O7—H34	109.5	O2—C25—C26	120.6 (4)
C38—O8—H38	109.3	O1—C25—C26	120.1 (3)
N5—O9—Ce1	96.4 (2)	C27—C26—C31	118.9 (3)
N5—O10—Ce1	97.8 (2)	C27—C26—C25	120.9 (4)
C1—N1—C5	118.2 (3)	C31—C26—C25	120.2 (4)
C1—N1—Ce1	121.2 (3)	O3—C27—C28	117.8 (4)
C5—N1—Ce1	120.4 (2)	O3—C27—C26	122.3 (4)
C12—N2—C6	117.6 (3)	C28—C27—C26	119.9 (4)
C12—N2—Ce1	120.8 (3)	C29—C28—C27	120.0 (5)
C6—N2—Ce1	121.1 (2)	C29—C28—H28	120.0
C13—N3—C17	118.8 (4)	C27—C28—H28	120.0
C13—N3—Ce1	120.9 (3)	C30—C29—C28	121.4 (4)
C17—N3—Ce1	119.5 (2)	C30—C29—H29	119.3
C24—N4—C18	118.3 (3)	C28—C29—H29	119.3
C24—N4—Ce1	120.6 (3)	C29—C30—C31	119.9 (4)
C18—N4—Ce1	120.9 (2)	C29—C30—H30	120.0
O11—N5—O9	122.8 (4)	C31—C30—H30	120.0
O11—N5—O10	120.2 (4)	O4—C31—C30	117.5 (4)
O9—N5—O10	117.0 (3)	O4—C31—C26	122.6 (4)
N1—C1—C2	124.0 (4)	C30—C31—C26	119.8 (4)
N1—C1—H1	118.0	O6—C32—O5	119.9 (4)
C2—C1—H1	118.0	O6—C32—C33	120.4 (4)
C3—C2—C1	118.2 (4)	O5—C32—C33	119.7 (4)
C3—C2—H2	120.9	C34—C33—C38	118.2 (4)
C1—C2—H2	120.9	C34—C33—C32	121.2 (4)
C2—C3—C4	119.4 (4)	C38—C33—C32	120.5 (4)
C2—C3—H3A	120.3	O7—C34—C35	118.7 (4)
C4—C3—H3A	120.3	O7—C34—C33	120.9 (4)
C3—C4—C5	118.3 (4)	C35—C34—C33	120.4 (5)
C3—C4—C9	122.3 (4)	C36—C35—C34	119.8 (5)
C5—C4—C9	119.4 (4)	C36—C35—H35	120.1
N1—C5—C4	121.9 (4)	C34—C35—H35	120.1
N1—C5—C6	118.7 (3)	C35—C36—C37	122.2 (4)
C4—C5—C6	119.5 (3)	C35—C36—H36	118.9
N2—C6—C7	122.8 (4)	C37—C36—H36	118.9
N2—C6—C5	118.1 (3)	C36—C37—C38	119.2 (5)
C7—C6—C5	119.1 (3)	C36—C37—H37	120.4
C10—C7—C6	117.2 (4)	C38—C37—H37	120.4
C10—C7—C8	122.8 (4)	O8—C38—C37	117.6 (4)
C6—C7—C8	120.0 (4)	O8—C38—C33	122.2 (3)
C9—C8—C7	120.8 (4)	C37—C38—C33	120.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H38···O6	0.82	1.85	2.582 (4)	147.
O7—H34···O5	0.82	1.82	2.552 (4)	148.
O4—H31···O2	0.82	1.86	2.584 (4)	146.
O3—H27···O1	0.82	1.87	2.583 (4)	145.

Table 1

Selected bond lengths (Å)

Ce1—O2	2.549 (3)
Ce1—O5	2.567 (3)
Ce1—O6	2.572 (3)
Ce1—O10	2.593 (3)
Ce1—O1	2.620 (3)
Ce1—O9	2.633 (3)
Ce1—N4	2.640 (3)
Ce1—N3	2.674 (3)
Ce1—N2	2.685 (3)
Ce1—N1	2.702 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H38⋯O6	0.82	1.85	2.582 (4)	147
O7—H34⋯O5	0.82	1.82	2.552 (4)	148
O4—H31⋯O2	0.82	1.86	2.584 (4)	146
O3—H27⋯O1	0.82	1.87	2.583 (4)	145