Poly[[diaqua-[μ(2)-3-carb-oxy-5-(pyridine-4-carboxamido)-benzoato][μ(4)-5-(pyridine-4-carboxamido)-isophthalato]cerium(III)] monohydrate].

In the title compound, {[Ce(C(14)H(9)N(2)O(5))(C(14)H(8)N(2)O(5))(H(2)O)(2)]·H(2)O}(n), three carboxyl groups of two independent isophthalate anions are deprotonated and they bridge the Ce(III) cations, forming a two-dimensional polymeric structure parallel to (001); another carboxyl group is not deprotonated and links with the adjacent pyridine ring via an O-H⋯N hydrogen bond. The Ce(III) cation is coordinated by six O atoms from carboxyl groups and two O atoms from coordinated water mol-ecules in a distorted square-anti-prismatic arrangement. Extensive O-H⋯O and O-H⋯N hydrogen bonding occurs in the crystal structure.

Related literature

For applications of lanthanide complexes with carboxyl ligands, see: Chin et al. (1994 ▶); Singh et al. (2002 ▶). For related complexes, see: Chen et al. (2011 ▶); Deng (2011 ▶); Qiu et al. (2007 ▶); Gubina et al. (2000 ▶); Wang et al. (2003 ▶).

Experimental

Crystal data

[Ce(C14H9N2O5)(C14H8N2O5)(H2O)2]·H2O

M = 763.62

Triclinic,

a = 9.6742 (8) Å

b = 10.6187 (8) Å

c = 15.8542 (12) Å

α = 81.443 (1)°

β = 78.753 (2)°

γ = 64.166 (2)°

V = 1433.98 (19) Å3

Z = 2

Mo Kα radiation

μ = 1.67 mm−1

T = 293 K

0.18 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.754, T max = 0.878

7189 measured reflections

4972 independent reflections

4669 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.04

4972 reflections

416 parameters

H-atom parameters constrained

Δρmax = 1.26 e Å−3

Δρmin = −1.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013402/xu5485sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013402/xu5485Isup2.hkl

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

[Ce(C14H9N2O5)(C14H8N2O5)(H2O)2]·H2O	Z = 2
Mr = 763.62	F(000) = 762
Triclinic, P1	Dx = 1.769 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6742 (8) Å	Cell parameters from 4972 reflections
b = 10.6187 (8) Å	θ = 2.1–25.0°
c = 15.8542 (12) Å	µ = 1.67 mm−1
α = 81.443 (1)°	T = 293 K
β = 78.753 (2)°	Block, colorless
γ = 64.166 (2)°	0.18 × 0.14 × 0.08 mm
V = 1433.98 (19) Å3

Bruker APEXII CCD diffractometer	4972 independent reflections
Radiation source: fine-focus sealed tube	4669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.754, Tmax = 0.878	k = −10→12
7189 measured reflections	l = −16→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0565P)2] where P = (Fo2 + 2Fc2)/3
4972 reflections	(Δ/σ)max = 0.002
416 parameters	Δρmax = 1.26 e Å−3
0 restraints	Δρmin = −1.23 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	0.731679 (19)	0.960889 (17)	0.503370 (11)	0.01875 (9)
C7	0.5111 (4)	1.0993 (4)	0.3253 (2)	0.0249 (7)
C3	0.5318 (4)	1.1620 (4)	0.2339 (2)	0.0259 (7)
C2	0.4389 (4)	1.1697 (4)	0.1751 (2)	0.0288 (8)
H2	0.3671	1.1309	0.1903	0.035*
C1	0.4534 (4)	1.2359 (4)	0.0934 (2)	0.0299 (8)
C6	0.5503 (5)	1.3043 (4)	0.0741 (2)	0.0353 (9)
H6	0.5531	1.3560	0.0215	0.042*
C5	0.6427 (5)	1.2962 (4)	0.1326 (2)	0.0323 (8)
C4	0.6388 (4)	1.2197 (4)	0.2109 (2)	0.0299 (8)
H4	0.7079	1.2070	0.2481	0.036*
C9	0.3250 (5)	1.1435 (5)	0.0155 (3)	0.0385 (9)
C10	0.2671 (5)	1.1588 (4)	−0.0677 (2)	0.0364 (9)
C14	0.1640 (6)	1.1015 (5)	−0.0707 (3)	0.0480 (11)
H14	0.1281	1.0590	−0.0213	0.058*
C13	0.1153 (6)	1.1087 (6)	−0.1486 (3)	0.0575 (13)
H13	0.0458	1.0705	−0.1502	0.069*
C12	0.2624 (7)	1.2209 (6)	−0.2179 (3)	0.0562 (13)
H12	0.2969	1.2615	−0.2687	0.067*
C11	0.3175 (6)	1.2199 (5)	−0.1436 (3)	0.0496 (11)
H11	0.3869	1.2593	−0.1445	0.059*
C8	0.7431 (5)	1.3750 (5)	0.1128 (3)	0.0398 (10)
C21	1.1064 (4)	0.7882 (3)	0.5569 (2)	0.0212 (7)
C17	1.2354 (4)	0.6476 (3)	0.5727 (2)	0.0210 (7)
C16	1.3614 (4)	0.6391 (4)	0.6063 (2)	0.0254 (7)
H16	1.3649	0.7207	0.6183	0.031*
C15	1.4816 (4)	0.5108 (4)	0.6220 (2)	0.0267 (7)
C20	1.4817 (4)	0.3891 (4)	0.6011 (2)	0.0267 (8)
H20	1.5633	0.3028	0.6113	0.032*
C19	1.3580 (4)	0.3973 (4)	0.5645 (2)	0.0230 (7)
C18	1.2335 (4)	0.5254 (3)	0.5521 (2)	0.0223 (7)
H18	1.1491	0.5296	0.5301	0.027*
C23	1.6591 (5)	0.4429 (4)	0.7281 (3)	0.0389 (9)
C24	1.7777 (4)	0.4767 (4)	0.7573 (3)	0.0337 (9)
C28	1.8537 (5)	0.5516 (5)	0.7061 (3)	0.0429 (10)
H28	1.8401	0.5784	0.6487	0.052*
C27	1.9499 (5)	0.5854 (5)	0.7425 (3)	0.0487 (12)
H27	1.9997	0.6369	0.7083	0.058*
C26	1.9051 (5)	0.4746 (5)	0.8713 (3)	0.0410 (10)
H26	1.9236	0.4468	0.9280	0.049*
C25	1.8059 (5)	0.4367 (5)	0.8415 (3)	0.0388 (10)
H25	1.7583	0.3848	0.8773	0.047*
C22	1.3639 (4)	0.2695 (4)	0.5316 (2)	0.0266 (7)
N1	0.3669 (4)	1.2433 (4)	0.0286 (2)	0.0359 (8)
H2A	0.4223	1.2574	−0.0215	0.043*
N2	0.1632 (5)	1.1672 (5)	−0.2205 (3)	0.0572 (11)
N3	1.6082 (4)	0.5117 (3)	0.6555 (2)	0.0326 (7)
H3A	1.6550	0.5606	0.6263	0.039*
N4	1.9759 (4)	0.5488 (4)	0.8236 (2)	0.0443 (9)
O1	0.3837 (3)	1.0938 (3)	0.35242 (16)	0.0368 (6)
O2	0.6201 (3)	1.0635 (3)	0.36808 (16)	0.0342 (6)
O3	0.8519 (5)	1.3290 (5)	0.1605 (3)	0.0757 (13)
H3	0.8914	1.3846	0.1553	0.114*
O4	0.7212 (4)	1.4718 (4)	0.0589 (2)	0.0537 (9)
O5	0.3353 (5)	1.0419 (4)	0.0661 (2)	0.0589 (10)
O6	0.9822 (3)	0.7910 (2)	0.54280 (17)	0.0303 (6)
O7	1.1291 (3)	0.8947 (2)	0.56132 (17)	0.0300 (6)
O8	1.4778 (3)	0.1545 (3)	0.53961 (18)	0.0381 (6)
O9	1.2553 (4)	0.2827 (3)	0.4946 (3)	0.0585 (10)
O10	1.6089 (5)	0.3622 (5)	0.7707 (2)	0.0748 (13)
O1W	0.9238 (4)	0.8370 (3)	0.37514 (18)	0.0537 (8)
H1WB	0.8907	0.7774	0.3687	0.064*
H1WA	0.9094	0.8880	0.3282	0.064*
O2W	0.7983 (3)	1.0672 (3)	0.61536 (17)	0.0369 (6)
H2WB	0.8768	1.0855	0.5974	0.044*
H2WA	0.8080	1.0189	0.6634	0.044*
O3W	0.7921 (9)	0.0666 (7)	0.7882 (3)	0.141 (3)
H3WA	0.7410	0.1497	0.7680	0.169*
H3WB	0.7469	0.0249	0.8251	0.169*

	U11	U22	U33	U12	U13	U23
Ce1	0.01952 (13)	0.01527 (12)	0.02393 (13)	−0.00835 (9)	−0.00774 (8)	0.00066 (8)
C7	0.0299 (19)	0.0230 (18)	0.0252 (17)	−0.0131 (15)	−0.0082 (14)	0.0005 (14)
C3	0.0283 (19)	0.0244 (18)	0.0276 (18)	−0.0127 (15)	−0.0074 (14)	0.0006 (14)
C2	0.032 (2)	0.032 (2)	0.0277 (18)	−0.0182 (17)	−0.0085 (15)	0.0009 (15)
C1	0.036 (2)	0.032 (2)	0.0289 (18)	−0.0183 (17)	−0.0137 (16)	0.0009 (15)
C6	0.044 (2)	0.040 (2)	0.0303 (19)	−0.026 (2)	−0.0115 (17)	0.0070 (17)
C5	0.038 (2)	0.037 (2)	0.0312 (19)	−0.0241 (18)	−0.0091 (16)	0.0024 (16)
C4	0.034 (2)	0.032 (2)	0.0304 (19)	−0.0181 (17)	−0.0119 (16)	0.0007 (15)
C9	0.047 (2)	0.044 (2)	0.036 (2)	−0.028 (2)	−0.0153 (18)	0.0044 (19)
C10	0.046 (2)	0.038 (2)	0.032 (2)	−0.0217 (19)	−0.0141 (17)	0.0011 (17)
C14	0.058 (3)	0.059 (3)	0.042 (2)	−0.035 (3)	−0.018 (2)	0.000 (2)
C13	0.062 (3)	0.064 (3)	0.058 (3)	−0.027 (3)	−0.026 (3)	−0.016 (3)
C12	0.070 (3)	0.068 (3)	0.032 (2)	−0.027 (3)	−0.016 (2)	−0.001 (2)
C11	0.062 (3)	0.056 (3)	0.040 (2)	−0.034 (3)	−0.012 (2)	0.001 (2)
C8	0.051 (3)	0.051 (3)	0.035 (2)	−0.037 (2)	−0.0121 (19)	0.0044 (19)
C21	0.0236 (17)	0.0231 (17)	0.0196 (16)	−0.0112 (14)	−0.0054 (13)	−0.0020 (13)
C17	0.0207 (17)	0.0190 (17)	0.0262 (17)	−0.0101 (14)	−0.0072 (13)	0.0006 (13)
C16	0.0284 (19)	0.0244 (18)	0.0305 (18)	−0.0159 (15)	−0.0086 (14)	−0.0013 (14)
C15	0.0250 (18)	0.0271 (19)	0.0315 (18)	−0.0121 (15)	−0.0116 (15)	0.0016 (15)
C20	0.0250 (18)	0.0212 (18)	0.0341 (19)	−0.0086 (15)	−0.0094 (15)	0.0008 (14)
C19	0.0227 (17)	0.0216 (17)	0.0273 (17)	−0.0114 (14)	−0.0059 (14)	0.0006 (14)
C18	0.0204 (17)	0.0209 (17)	0.0302 (18)	−0.0115 (14)	−0.0069 (14)	−0.0018 (14)
C23	0.040 (2)	0.040 (2)	0.046 (2)	−0.023 (2)	−0.0188 (19)	0.0057 (19)
C24	0.029 (2)	0.034 (2)	0.042 (2)	−0.0148 (17)	−0.0149 (17)	0.0018 (17)
C28	0.043 (2)	0.060 (3)	0.037 (2)	−0.030 (2)	−0.0140 (18)	0.006 (2)
C27	0.046 (3)	0.071 (3)	0.046 (2)	−0.041 (3)	−0.015 (2)	0.008 (2)
C26	0.039 (2)	0.053 (3)	0.036 (2)	−0.023 (2)	−0.0123 (18)	0.0020 (19)
C25	0.038 (2)	0.045 (2)	0.041 (2)	−0.024 (2)	−0.0171 (18)	0.0103 (19)
C22	0.0270 (19)	0.0203 (18)	0.0343 (19)	−0.0124 (15)	−0.0035 (15)	−0.0009 (14)
N1	0.049 (2)	0.045 (2)	0.0279 (16)	−0.0308 (17)	−0.0168 (15)	0.0070 (14)
N2	0.068 (3)	0.060 (3)	0.042 (2)	−0.014 (2)	−0.026 (2)	−0.0129 (19)
N3	0.0294 (17)	0.0320 (17)	0.0443 (18)	−0.0168 (14)	−0.0195 (14)	0.0048 (14)
N4	0.043 (2)	0.064 (2)	0.0414 (19)	−0.035 (2)	−0.0151 (16)	0.0026 (17)
O1	0.0304 (15)	0.0464 (17)	0.0334 (14)	−0.0189 (13)	−0.0077 (11)	0.0105 (12)
O2	0.0380 (15)	0.0454 (16)	0.0303 (13)	−0.0250 (13)	−0.0175 (12)	0.0055 (12)
O3	0.088 (3)	0.102 (3)	0.083 (3)	−0.080 (3)	−0.057 (2)	0.047 (2)
O4	0.074 (2)	0.061 (2)	0.0481 (18)	−0.0527 (19)	−0.0203 (16)	0.0207 (16)
O5	0.099 (3)	0.059 (2)	0.0472 (18)	−0.057 (2)	−0.0355 (19)	0.0185 (16)
O6	0.0256 (13)	0.0224 (13)	0.0483 (15)	−0.0106 (11)	−0.0172 (12)	−0.0009 (11)
O7	0.0316 (14)	0.0194 (12)	0.0454 (15)	−0.0148 (11)	−0.0152 (12)	0.0045 (11)
O8	0.0426 (17)	0.0220 (14)	0.0433 (16)	−0.0051 (12)	−0.0116 (13)	−0.0035 (11)
O9	0.051 (2)	0.0288 (16)	0.111 (3)	−0.0155 (14)	−0.041 (2)	−0.0168 (17)
O10	0.089 (3)	0.099 (3)	0.076 (2)	−0.076 (3)	−0.051 (2)	0.042 (2)
O1W	0.069 (2)	0.0480 (19)	0.0349 (16)	−0.0105 (17)	−0.0130 (15)	−0.0133 (14)
O2W	0.0388 (16)	0.0416 (16)	0.0379 (15)	−0.0226 (13)	−0.0083 (12)	−0.0033 (12)
O3W	0.230 (8)	0.154 (6)	0.076 (3)	−0.129 (6)	−0.007 (4)	0.011 (4)

Ce1—O1i	2.446 (2)	C17—C16	1.385 (5)
Ce1—O2	2.477 (2)	C17—C18	1.393 (5)
Ce1—O6	2.442 (2)	C16—C15	1.379 (5)
Ce1—O7ii	2.452 (2)	C16—H16	0.9300
Ce1—O8iii	2.447 (3)	C15—C20	1.381 (5)
Ce1—O9iv	2.530 (3)	C15—N3	1.431 (4)
Ce1—O1W	2.552 (3)	C20—C19	1.394 (5)
Ce1—O2W	2.553 (3)	C20—H20	0.9300
C7—O1	1.248 (4)	C19—C18	1.387 (5)
C7—O2	1.252 (4)	C19—C22	1.498 (5)
C7—C3	1.517 (5)	C18—H18	0.9300
C3—C4	1.385 (5)	C23—O10	1.220 (5)
C3—C2	1.386 (5)	C23—N3	1.326 (5)
C2—C1	1.392 (5)	C23—C24	1.508 (5)
C2—H2	0.9300	C24—C25	1.382 (5)
C1—C6	1.385 (5)	C24—C28	1.384 (6)
C1—N1	1.419 (4)	C28—C27	1.374 (6)
C6—C5	1.377 (5)	C28—H28	0.9300
C6—H6	0.9300	C27—N4	1.326 (6)
C5—C4	1.383 (5)	C27—H27	0.9300
C5—C8	1.501 (5)	C26—N4	1.324 (6)
C4—H4	0.9300	C26—C25	1.369 (6)
C9—O5	1.224 (5)	C26—H26	0.9300
C9—N1	1.344 (5)	C25—H25	0.9300
C9—C10	1.492 (5)	C22—O9	1.247 (4)
C10—C11	1.386 (6)	C22—O8	1.248 (4)
C10—C14	1.387 (6)	N1—H2A	0.8998
C14—C13	1.386 (6)	N3—H3A	0.8600
C14—H14	0.9300	O1—Ce1i	2.446 (2)
C13—N2	1.316 (7)	O3—H3	0.8200
C13—H13	0.9300	O7—Ce1ii	2.452 (2)
C12—N2	1.322 (7)	O8—Ce1v	2.447 (3)
C12—C11	1.381 (6)	O9—Ce1iv	2.530 (3)
C12—H12	0.9300	O1W—H1WB	0.8499
C11—H11	0.9300	O1W—H1WA	0.8495
C8—O4	1.205 (5)	O2W—H2WB	0.8506
C8—O3	1.291 (5)	O2W—H2WA	0.8495
C21—O6	1.252 (4)	O3W—H3WA	0.8496
C21—O7	1.256 (4)	O3W—H3WB	0.8500
C21—C17	1.496 (5)
O6—Ce1—O1i	87.00 (9)	O4—C8—O3	124.6 (4)
O6—Ce1—O8iii	150.29 (9)	O4—C8—C5	122.7 (4)
O1i—Ce1—O8iii	71.37 (9)	O3—C8—C5	112.8 (4)
O6—Ce1—O7ii	85.08 (8)	O6—C21—O7	124.9 (3)
O1i—Ce1—O7ii	137.06 (9)	O6—C21—C17	117.5 (3)
O8iii—Ce1—O7ii	96.89 (9)	O7—C21—C17	117.6 (3)
O6—Ce1—O2	136.56 (9)	C16—C17—C18	119.4 (3)
O1i—Ce1—O2	131.89 (9)	C16—C17—C21	119.3 (3)
O8iii—Ce1—O2	72.04 (9)	C18—C17—C21	121.3 (3)
O7ii—Ce1—O2	77.34 (8)	C15—C16—C17	120.6 (3)
O6—Ce1—O9iv	71.67 (9)	C15—C16—H16	119.7
O1i—Ce1—O9iv	72.84 (12)	C17—C16—H16	119.7
O8iii—Ce1—O9iv	118.35 (10)	C16—C15—C20	120.5 (3)
O7ii—Ce1—O9iv	141.86 (11)	C16—C15—N3	117.0 (3)
O2—Ce1—O9iv	98.94 (10)	C20—C15—N3	122.4 (3)
O6—Ce1—O1W	66.88 (9)	C15—C20—C19	119.2 (3)
O1i—Ce1—O1W	140.12 (10)	C15—C20—H20	120.4
O8iii—Ce1—O1W	141.96 (9)	C19—C20—H20	120.4
O7ii—Ce1—O1W	72.58 (10)	C18—C19—C20	120.4 (3)
O2—Ce1—O1W	70.00 (10)	C18—C19—C22	119.1 (3)
O9iv—Ce1—O1W	70.61 (12)	C20—C19—C22	120.3 (3)
O6—Ce1—O2W	72.59 (9)	C19—C18—C17	119.8 (3)
O1i—Ce1—O2W	70.31 (9)	C19—C18—H18	120.1
O8iii—Ce1—O2W	80.89 (9)	C17—C18—H18	120.1
O7ii—Ce1—O2W	67.04 (9)	O10—C23—N3	122.6 (4)
O2—Ce1—O2W	131.79 (9)	O10—C23—C24	121.9 (4)
O9iv—Ce1—O2W	129.14 (10)	N3—C23—C24	115.5 (3)
O1W—Ce1—O2W	124.10 (10)	C25—C24—C28	118.2 (4)
O1—C7—O2	125.7 (3)	C25—C24—C23	117.8 (4)
O1—C7—C3	116.8 (3)	C28—C24—C23	123.9 (3)
O2—C7—C3	117.4 (3)	C27—C28—C24	118.2 (4)
C4—C3—C2	119.9 (3)	C27—C28—H28	120.9
C4—C3—C7	119.1 (3)	C24—C28—H28	120.9
C2—C3—C7	120.8 (3)	N4—C27—C28	123.8 (4)
C3—C2—C1	119.7 (3)	N4—C27—H27	118.1
C3—C2—H2	120.1	C28—C27—H27	118.1
C1—C2—H2	120.1	N4—C26—C25	123.4 (4)
C6—C1—C2	119.6 (3)	N4—C26—H26	118.3
C6—C1—N1	117.3 (3)	C25—C26—H26	118.3
C2—C1—N1	123.1 (3)	C26—C25—C24	119.0 (4)
C5—C6—C1	120.2 (4)	C26—C25—H25	120.5
C5—C6—H6	119.9	C24—C25—H25	120.5
C1—C6—H6	119.9	O9—C22—O8	121.8 (3)
C6—C5—C4	120.1 (3)	O9—C22—C19	118.4 (3)
C6—C5—C8	120.1 (3)	O8—C22—C19	119.8 (3)
C4—C5—C8	119.8 (3)	C9—N1—C1	125.9 (3)
C5—C4—C3	119.9 (3)	C9—N1—H2A	105.5
C5—C4—H4	120.0	C1—N1—H2A	105.1
C3—C4—H4	120.0	C13—N2—C12	118.3 (4)
O5—C9—N1	124.0 (4)	C23—N3—C15	125.0 (3)
O5—C9—C10	119.6 (4)	C23—N3—H3A	117.5
N1—C9—C10	116.4 (3)	C15—N3—H3A	117.5
C11—C10—C14	118.0 (4)	C26—N4—C27	117.4 (4)
C11—C10—C9	123.6 (4)	C7—O1—Ce1i	131.8 (2)
C14—C10—C9	118.3 (4)	C7—O2—Ce1	149.8 (2)
C13—C14—C10	118.9 (5)	C8—O3—H3	109.5
C13—C14—H14	120.5	C21—O6—Ce1	139.3 (2)
C10—C14—H14	120.5	C21—O7—Ce1ii	147.2 (2)
N2—C13—C14	122.8 (5)	C22—O8—Ce1v	159.1 (3)
N2—C13—H13	118.6	C22—O9—Ce1iv	106.3 (2)
C14—C13—H13	118.6	Ce1—O1W—H1WB	101.1
N2—C12—C11	123.5 (5)	Ce1—O1W—H1WA	112.4
N2—C12—H12	118.3	H1WB—O1W—H1WA	101.8
C11—C12—H12	118.3	Ce1—O2W—H2WB	113.4
C12—C11—C10	118.5 (5)	Ce1—O2W—H2WA	113.3
C12—C11—H11	120.8	H2WB—O2W—H2WA	110.7
C10—C11—H11	120.8	H3WA—O3W—H3WB	120.4
O1—C7—C3—C4	155.7 (4)	N3—C23—C24—C28	−12.3 (6)
O2—C7—C3—C4	−21.2 (5)	C25—C24—C28—C27	−1.7 (7)
O1—C7—C3—C2	−20.4 (5)	C23—C24—C28—C27	174.8 (4)
O2—C7—C3—C2	162.7 (3)	C24—C28—C27—N4	0.9 (8)
C4—C3—C2—C1	−0.2 (6)	N4—C26—C25—C24	0.3 (7)
C7—C3—C2—C1	175.9 (3)	C28—C24—C25—C26	1.2 (6)
C3—C2—C1—C6	−5.8 (6)	C23—C24—C25—C26	−175.5 (4)
C3—C2—C1—N1	177.5 (4)	C18—C19—C22—O9	−0.5 (5)
C2—C1—C6—C5	6.0 (6)	C20—C19—C22—O9	−175.7 (4)
N1—C1—C6—C5	−177.1 (4)	C18—C19—C22—O8	177.5 (3)
C1—C6—C5—C4	−0.1 (6)	C20—C19—C22—O8	2.3 (5)
C1—C6—C5—C8	−177.7 (4)	O5—C9—N1—C1	11.9 (7)
C6—C5—C4—C3	−5.9 (6)	C10—C9—N1—C1	−166.3 (4)
C8—C5—C4—C3	171.6 (4)	C6—C1—N1—C9	148.1 (4)
C2—C3—C4—C5	6.0 (6)	C2—C1—N1—C9	−35.2 (6)
C7—C3—C4—C5	−170.1 (3)	C14—C13—N2—C12	0.2 (8)
O5—C9—C10—C11	−147.1 (5)	C11—C12—N2—C13	−0.5 (8)
N1—C9—C10—C11	31.2 (7)	O10—C23—N3—C15	5.8 (7)
O5—C9—C10—C14	29.0 (7)	C24—C23—N3—C15	−171.2 (3)
N1—C9—C10—C14	−152.7 (4)	C16—C15—N3—C23	123.6 (4)
C11—C10—C14—C13	−0.4 (7)	C20—C15—N3—C23	−60.1 (5)
C9—C10—C14—C13	−176.8 (5)	C25—C26—N4—C27	−1.1 (7)
C10—C14—C13—N2	0.3 (8)	C28—C27—N4—C26	0.5 (8)
N2—C12—C11—C10	0.3 (8)	O2—C7—O1—Ce1i	7.2 (6)
C14—C10—C11—C12	0.2 (7)	C3—C7—O1—Ce1i	−169.5 (2)
C9—C10—C11—C12	176.3 (5)	O1—C7—O2—Ce1	4.2 (8)
C6—C5—C8—O4	18.6 (7)	C3—C7—O2—Ce1	−179.1 (3)
C4—C5—C8—O4	−158.9 (4)	O6—Ce1—O2—C7	134.9 (5)
C6—C5—C8—O3	−162.3 (4)	O1i—Ce1—O2—C7	−12.8 (5)
C4—C5—C8—O3	20.1 (6)	O8iii—Ce1—O2—C7	−54.9 (5)
O6—C21—C17—C16	−166.5 (3)	O7ii—Ce1—O2—C7	−156.5 (5)
O7—C21—C17—C16	11.6 (5)	O9iv—Ce1—O2—C7	62.2 (5)
O6—C21—C17—C18	15.4 (5)	O1W—Ce1—O2—C7	127.6 (5)
O7—C21—C17—C18	−166.6 (3)	O2W—Ce1—O2—C7	−114.0 (5)
C18—C17—C16—C15	−2.2 (5)	O7—C21—O6—Ce1	7.3 (6)
C21—C17—C16—C15	179.6 (3)	C17—C21—O6—Ce1	−174.9 (2)
C17—C16—C15—C20	2.8 (5)	O1i—Ce1—O6—C21	−112.6 (4)
C17—C16—C15—N3	179.1 (3)	O8iii—Ce1—O6—C21	−70.1 (4)
C16—C15—C20—C19	−0.5 (5)	O7ii—Ce1—O6—C21	25.2 (3)
N3—C15—C20—C19	−176.6 (3)	O2—Ce1—O6—C21	90.9 (4)
C15—C20—C19—C18	−2.4 (5)	O9iv—Ce1—O6—C21	174.5 (4)
C15—C20—C19—C22	172.8 (3)	O1W—Ce1—O6—C21	98.3 (4)
C20—C19—C18—C17	3.0 (5)	O2W—Ce1—O6—C21	−42.3 (3)
C22—C19—C18—C17	−172.2 (3)	O6—C21—O7—Ce1ii	−112.8 (4)
C16—C17—C18—C19	−0.7 (5)	C17—C21—O7—Ce1ii	69.4 (5)
C21—C17—C18—C19	177.5 (3)	O9—C22—O8—Ce1v	85.9 (8)
O10—C23—C24—C25	−12.8 (7)	C19—C22—O8—Ce1v	−92.0 (8)
N3—C23—C24—C25	164.2 (4)	O8—C22—O9—Ce1iv	20.5 (5)
O10—C23—C24—C28	170.6 (5)	C19—C22—O9—Ce1iv	−161.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N2vi	0.85	2.21	2.756 (5)	122
O2W—H2WB···O1Wii	0.85	2.53	3.297 (5)	150
O2W—H2WA···O3Wvii	0.85	2.07	2.728 (6)	133
O3W—H3WA···O10viii	0.85	2.06	2.856 (8)	157
O3W—H3WB···O5ix	0.85	1.92	2.742 (6)	161
O3—H3···N4x	0.82	1.81	2.583 (5)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯N2i	0.85	2.21	2.756 (5)	122
O2W—H2WB⋯O1Wii	0.85	2.53	3.297 (5)	150
O2W—H2WA⋯O3Wiii	0.85	2.07	2.728 (6)	133
O3W—H3WA⋯O10iv	0.85	2.06	2.856 (8)	157
O3W—H3WB⋯O5v	0.85	1.92	2.742 (6)	161
O3—H3⋯N4vi	0.82	1.81	2.583 (5)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .