catena-Poly[[[diaqua-(nitrato-κO,O')cerium(III)]-bis-[μ-2-(4-hy-droxy-phen-yl)acetato]-κO,O':O;κO:O,O'] mono-hydrate].

In the title compound, {[Ce(C(8)H(7)O(3))(2)(NO(3))(H(2)O)(2)]·H(2)O}(n), the Ce(III) ion is coordinated by eight O atoms from four 2-(4-hy-droxy-phen-yl)acetate (HPAA) ligands, two O atoms from the chelating nitrate anion and two water mol-ecules in a distorted bis-capped quadrangular prismatic geometry. The HPAA ligands coordinate in a bridging tridentate mode. In the crystal, inter-molecular O-H⋯O hydrogen bonds form a three-dimensional network which consolidates the packing.

Related literature

For the crystal structures of related carb­oxy­lic metal-organic complexes, see: Liu et al. (2010 ▶); Fang & Zhang (2006 ▶); Wang et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

[Ce(C8H7O3)2(NO3)(H2O)2]·H2O

M = 558.45

Triclinic,

a = 8.1151 (3) Å

b = 9.8048 (4) Å

c = 13.2396 (5) Å

α = 92.120 (2)°

β = 90.829 (2)°

γ = 112.550 (2)°

V = 971.76 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.41 mm−1

T = 296 K

0.14 × 0.14 × 0.03 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.716, T max = 0.935

15535 measured reflections

4492 independent reflections

4133 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.050

S = 0.98

4492 reflections

289 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047239/cv2794sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047239/cv2794Isup2.hkl

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

[Ce(C8H7O3)2(NO3)(H2O)2]·H2O	Z = 2
Mr = 558.45	F(000) = 554
Triclinic, P1	Dx = 1.909 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1151 (3) Å	Cell parameters from 8276 reflections
b = 9.8048 (4) Å	θ = 2.3–27.7°
c = 13.2396 (5) Å	µ = 2.41 mm−1
α = 92.120 (2)°	T = 296 K
β = 90.829 (2)°	Block, colourless
γ = 112.550 (2)°	0.14 × 0.14 × 0.03 mm
V = 971.76 (6) Å3

Bruker APEXII diffractometer	4492 independent reflections
Radiation source: fine-focus sealed tube	4133 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.716, Tmax = 0.935	k = −12→12
15535 measured reflections	l = −16→17

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.0249P] where P = (Fo2 + 2Fc2)/3
4492 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.72 e Å−3
9 restraints	Δρmin = −0.35 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	0.208699 (13)	−0.089222 (12)	0.466072 (8)	0.02011 (5)
N1	0.0546 (3)	−0.3859 (2)	0.33905 (16)	0.0335 (4)
O1W	0.2726 (2)	−0.28503 (19)	0.56174 (16)	0.0402 (4)
H1WA	0.379 (2)	−0.277 (3)	0.573 (2)	0.060*
H1WB	0.214 (3)	−0.364 (2)	0.587 (2)	0.060*
O1	0.7474 (3)	0.5608 (2)	0.07849 (16)	0.0632 (6)
H1A	0.7371	0.4920	0.0384	0.095*
O2	0.3683 (2)	0.18203 (18)	0.42823 (15)	0.0372 (4)
O2W	0.0678 (2)	−0.0555 (2)	0.30083 (12)	0.0346 (4)
H2WA	−0.019 (3)	−0.031 (3)	0.304 (2)	0.052*
H2WB	0.055 (4)	−0.101 (3)	0.2447 (16)	0.052*
O3	0.09817 (19)	0.14048 (17)	0.47414 (12)	0.0290 (3)
O3W	0.7347 (4)	0.4032 (3)	−0.09596 (17)	0.0650 (6)
H3WA	0.801 (5)	0.363 (4)	−0.120 (3)	0.098*
H3WB	0.721 (6)	0.448 (4)	−0.144 (2)	0.098*
O4	0.0288 (3)	−0.1882 (3)	1.10768 (14)	0.0645 (7)
H4A	−0.0557	−0.2660	1.0935	0.097*
O5	0.4853 (2)	0.03842 (17)	0.59596 (11)	0.0272 (3)
O6	0.2196 (2)	−0.0107 (2)	0.65299 (12)	0.0358 (4)
O7	−0.0071 (3)	−0.4974 (2)	0.2852 (2)	0.0635 (7)
O8	−0.0245 (2)	−0.3651 (2)	0.41577 (15)	0.0475 (5)
O9	0.2019 (2)	−0.28460 (19)	0.32163 (14)	0.0404 (4)
C1	0.6258 (3)	0.5107 (3)	0.1536 (2)	0.0408 (6)
C2	0.6439 (4)	0.6015 (3)	0.2378 (2)	0.0428 (6)
H2A	0.7371	0.6938	0.2434	0.051*
C3	0.5227 (3)	0.5555 (3)	0.3150 (2)	0.0390 (6)
H3A	0.5352	0.6178	0.3719	0.047*
C4	0.3841 (3)	0.4185 (3)	0.3082 (2)	0.0345 (5)
C5	0.3692 (5)	0.3305 (3)	0.2238 (3)	0.0555 (8)
H5A	0.2763	0.2381	0.2182	0.067*
C6	0.4886 (4)	0.3746 (3)	0.1456 (2)	0.0592 (9)
H6A	0.4754	0.3125	0.0886	0.071*
C7	0.2519 (4)	0.3655 (3)	0.3915 (2)	0.0427 (6)
H7A	0.2849	0.4411	0.4457	0.051*
H7B	0.1347	0.3536	0.3652	0.051*
C8	0.2399 (3)	0.2229 (2)	0.43422 (17)	0.0251 (4)
C9	0.1213 (3)	−0.1356 (3)	1.02159 (19)	0.0388 (6)
C10	0.2361 (4)	0.0088 (3)	1.0244 (2)	0.0555 (8)
H10A	0.2437	0.0702	1.0810	0.067*
C11	0.3413 (4)	0.0630 (3)	0.9425 (2)	0.0553 (8)
H11A	0.4198	0.1616	0.9448	0.066*
C12	0.3332 (3)	−0.0242 (3)	0.85785 (18)	0.0353 (5)
C13	0.2135 (4)	−0.1682 (3)	0.8556 (2)	0.0459 (7)
H13A	0.2035	−0.2289	0.7983	0.055*
C14	0.1074 (4)	−0.2248 (3)	0.9369 (2)	0.0492 (7)
H14A	0.0271	−0.3227	0.9342	0.059*
C15	0.4615 (3)	0.0341 (4)	0.77382 (19)	0.0479 (7)
H15A	0.5323	0.1378	0.7900	0.058*
H15B	0.5426	−0.0173	0.7732	0.058*
C16	0.3832 (3)	0.0212 (2)	0.66965 (16)	0.0242 (4)

	U11	U22	U33	U12	U13	U23
Ce1	0.01487 (7)	0.02446 (7)	0.01999 (7)	0.00608 (5)	0.00407 (4)	0.00347 (4)
N1	0.0315 (11)	0.0260 (9)	0.0429 (13)	0.0112 (8)	−0.0058 (9)	−0.0002 (8)
O1W	0.0236 (8)	0.0339 (9)	0.0607 (13)	0.0071 (7)	−0.0001 (8)	0.0178 (8)
O1	0.0624 (14)	0.0546 (12)	0.0442 (13)	−0.0094 (10)	0.0298 (11)	−0.0038 (9)
O2	0.0210 (8)	0.0335 (9)	0.0589 (12)	0.0109 (7)	0.0102 (8)	0.0174 (8)
O2W	0.0340 (9)	0.0529 (11)	0.0230 (9)	0.0243 (8)	−0.0033 (7)	−0.0057 (7)
O3	0.0194 (7)	0.0307 (8)	0.0331 (9)	0.0048 (6)	0.0083 (7)	0.0039 (6)
O3W	0.0785 (17)	0.0687 (16)	0.0513 (15)	0.0324 (13)	0.0073 (13)	−0.0031 (11)
O4	0.0586 (14)	0.0721 (14)	0.0248 (11)	−0.0171 (11)	0.0180 (10)	−0.0021 (9)
O5	0.0219 (7)	0.0368 (8)	0.0207 (8)	0.0087 (6)	0.0063 (6)	0.0011 (6)
O6	0.0219 (8)	0.0644 (11)	0.0236 (9)	0.0192 (8)	0.0032 (7)	0.0003 (8)
O7	0.0589 (13)	0.0358 (10)	0.0941 (18)	0.0202 (10)	−0.0261 (13)	−0.0266 (11)
O8	0.0283 (9)	0.0636 (12)	0.0410 (11)	0.0064 (9)	0.0079 (8)	0.0069 (9)
O9	0.0352 (10)	0.0339 (9)	0.0484 (11)	0.0092 (8)	0.0131 (8)	−0.0003 (8)
C1	0.0383 (14)	0.0394 (13)	0.0352 (15)	0.0037 (11)	0.0138 (11)	0.0057 (11)
C2	0.0344 (14)	0.0401 (14)	0.0386 (16)	−0.0028 (11)	0.0087 (12)	0.0015 (11)
C3	0.0422 (14)	0.0419 (14)	0.0296 (14)	0.0124 (11)	0.0068 (11)	0.0025 (10)
C4	0.0386 (13)	0.0295 (11)	0.0391 (14)	0.0157 (10)	0.0147 (11)	0.0126 (10)
C5	0.0596 (19)	0.0303 (13)	0.058 (2)	−0.0042 (13)	0.0274 (16)	0.0008 (12)
C6	0.067 (2)	0.0388 (15)	0.0484 (19)	−0.0057 (14)	0.0284 (16)	−0.0081 (13)
C7	0.0450 (15)	0.0391 (13)	0.0534 (17)	0.0241 (12)	0.0268 (13)	0.0209 (12)
C8	0.0193 (10)	0.0288 (10)	0.0257 (12)	0.0073 (8)	0.0025 (8)	0.0040 (8)
C9	0.0373 (14)	0.0454 (14)	0.0220 (13)	0.0026 (11)	0.0068 (10)	0.0028 (10)
C10	0.062 (2)	0.0504 (17)	0.0303 (16)	−0.0042 (14)	0.0157 (14)	−0.0092 (12)
C11	0.0573 (18)	0.0456 (16)	0.0322 (16)	−0.0143 (13)	0.0101 (13)	−0.0032 (12)
C12	0.0259 (12)	0.0538 (15)	0.0174 (12)	0.0054 (11)	0.0007 (9)	0.0040 (10)
C13	0.0522 (17)	0.0505 (16)	0.0240 (14)	0.0080 (13)	0.0093 (12)	−0.0070 (11)
C14	0.0559 (18)	0.0397 (14)	0.0325 (16)	−0.0034 (13)	0.0117 (13)	−0.0011 (11)
C15	0.0229 (12)	0.083 (2)	0.0223 (13)	0.0018 (12)	0.0036 (10)	0.0068 (13)
C16	0.0204 (10)	0.0303 (10)	0.0208 (11)	0.0085 (8)	0.0036 (8)	0.0009 (8)

Ce1—O3i	2.4914 (14)	O6—C16	1.256 (2)
Ce1—O5ii	2.4955 (14)	C1—C6	1.370 (4)
Ce1—O2W	2.5444 (16)	C1—C2	1.371 (4)
Ce1—O2	2.5451 (16)	C2—C3	1.392 (4)
Ce1—O1W	2.5463 (16)	C2—H2A	0.9300
Ce1—O6	2.5546 (17)	C3—C4	1.381 (4)
Ce1—O9	2.6411 (18)	C3—H3A	0.9300
Ce1—O5	2.6717 (15)	C4—C5	1.360 (4)
Ce1—O8	2.692 (2)	C4—C7	1.512 (3)
Ce1—O3	2.7245 (15)	C5—C6	1.393 (4)
Ce1—C16	2.990 (2)	C5—H5A	0.9300
N1—O7	1.211 (3)	C6—H6A	0.9300
N1—O9	1.258 (3)	C7—C8	1.497 (3)
N1—O8	1.261 (3)	C7—H7A	0.9700
O1W—H1WA	0.847 (16)	C7—H7B	0.9700
O1W—H1WB	0.819 (17)	C9—C10	1.362 (4)
O1—C1	1.377 (3)	C9—C14	1.372 (4)
O1—H1A	0.8200	C10—C11	1.382 (4)
O2—C8	1.253 (2)	C10—H10A	0.9300
O2W—H2WA	0.831 (16)	C11—C12	1.369 (4)
O2W—H2WB	0.835 (17)	C11—H11A	0.9300
O3—C8	1.262 (3)	C12—C13	1.371 (4)
O3—Ce1i	2.4914 (14)	C12—C15	1.508 (3)
O3W—H3WA	0.846 (18)	C13—C14	1.383 (4)
O3W—H3WB	0.818 (18)	C13—H13A	0.9300
O4—C9	1.378 (3)	C14—H14A	0.9300
O4—H4A	0.8200	C15—C16	1.491 (3)
O5—C16	1.263 (2)	C15—H15A	0.9700
O5—Ce1ii	2.4955 (14)	C15—H15B	0.9700
O3i—Ce1—O5ii	179.31 (5)	C8—O3—Ce1	90.79 (12)
O3i—Ce1—O2W	81.58 (5)	Ce1i—O3—Ce1	117.31 (6)
O5ii—Ce1—O2W	97.77 (5)	H3WA—O3W—H3WB	101 (3)
O3i—Ce1—O2	111.16 (5)	C9—O4—H4A	109.5
O5ii—Ce1—O2	68.82 (5)	C16—O5—Ce1ii	148.67 (14)
O2W—Ce1—O2	74.31 (6)	C16—O5—Ce1	91.74 (12)
O3i—Ce1—O1W	98.50 (5)	Ce1ii—O5—Ce1	118.06 (6)
O5ii—Ce1—O1W	81.87 (5)	C16—O6—Ce1	97.49 (13)
O2W—Ce1—O1W	141.07 (6)	N1—O8—Ce1	96.80 (13)
O2—Ce1—O1W	138.12 (5)	N1—O9—Ce1	99.36 (13)
O3i—Ce1—O6	69.62 (5)	C6—C1—C2	119.9 (2)
O5ii—Ce1—O6	111.05 (5)	C6—C1—O1	121.8 (2)
O2W—Ce1—O6	138.36 (5)	C2—C1—O1	118.2 (2)
O2—Ce1—O6	88.46 (6)	C1—C2—C3	120.0 (2)
O1W—Ce1—O6	74.55 (6)	C1—C2—H2A	120.0
O3i—Ce1—O9	110.48 (5)	C3—C2—H2A	120.0
O5ii—Ce1—O9	69.02 (5)	C4—C3—C2	120.7 (2)
O2W—Ce1—O9	67.10 (6)	C4—C3—H3A	119.6
O2—Ce1—O9	116.63 (6)	C2—C3—H3A	119.6
O1W—Ce1—O9	76.79 (6)	C5—C4—C3	118.1 (2)
O6—Ce1—O9	150.94 (6)	C5—C4—C7	120.2 (2)
O3i—Ce1—O5	118.73 (5)	C3—C4—C7	121.7 (2)
O5ii—Ce1—O5	61.94 (6)	C4—C5—C6	122.1 (3)
O2W—Ce1—O5	143.60 (5)	C4—C5—H5A	119.0
O2—Ce1—O5	70.22 (5)	C6—C5—H5A	119.0
O1W—Ce1—O5	69.76 (5)	C1—C6—C5	119.2 (3)
O6—Ce1—O5	49.13 (5)	C1—C6—H6A	120.4
O9—Ce1—O5	123.16 (5)	C5—C6—H6A	120.4
O3i—Ce1—O8	66.61 (5)	C8—C7—C4	114.46 (18)
O5ii—Ce1—O8	113.06 (5)	C8—C7—H7A	108.6
O2W—Ce1—O8	77.36 (6)	C4—C7—H7A	108.6
O2—Ce1—O8	151.55 (6)	C8—C7—H7B	108.6
O1W—Ce1—O8	67.42 (6)	C4—C7—H7B	108.6
O6—Ce1—O8	115.06 (6)	H7A—C7—H7B	107.6
O9—Ce1—O8	47.31 (5)	O2—C8—O3	119.32 (19)
O5—Ce1—O8	137.13 (6)	O2—C8—C7	120.53 (19)
O3i—Ce1—O3	62.69 (6)	O3—C8—C7	120.11 (18)
O5ii—Ce1—O3	117.26 (5)	C10—C9—C14	120.0 (2)
O2W—Ce1—O3	66.25 (5)	C10—C9—O4	117.6 (2)
O2—Ce1—O3	48.50 (5)	C14—C9—O4	122.3 (2)
O1W—Ce1—O3	147.40 (6)	C9—C10—C11	119.4 (3)
O6—Ce1—O3	73.89 (5)	C9—C10—H10A	120.3
O9—Ce1—O3	133.34 (5)	C11—C10—H10A	120.3
O5—Ce1—O3	95.12 (5)	C12—C11—C10	121.8 (3)
O8—Ce1—O3	120.31 (5)	C12—C11—H11A	119.1
O3i—Ce1—C16	94.08 (5)	C10—C11—H11A	119.1
O5ii—Ce1—C16	86.60 (5)	C11—C12—C13	117.8 (2)
O2W—Ce1—C16	152.02 (6)	C11—C12—C15	120.5 (2)
O2—Ce1—C16	81.73 (6)	C13—C12—C15	121.6 (2)
O1W—Ce1—C16	66.86 (6)	C12—C13—C14	121.3 (2)
O6—Ce1—C16	24.61 (5)	C12—C13—H13A	119.3
O9—Ce1—C16	138.72 (6)	C14—C13—H13A	119.3
O5—Ce1—C16	24.99 (5)	C9—C14—C13	119.6 (3)
O8—Ce1—C16	126.30 (6)	C9—C14—H14A	120.2
O3—Ce1—C16	87.12 (5)	C13—C14—H14A	120.2
O7—N1—O9	121.7 (2)	C16—C15—C12	117.1 (2)
O7—N1—O8	122.0 (2)	C16—C15—H15A	108.0
O9—N1—O8	116.4 (2)	C12—C15—H15A	108.0
Ce1—O1W—H1WA	120 (2)	C16—C15—H15B	108.0
Ce1—O1W—H1WB	137 (2)	C12—C15—H15B	108.0
H1WA—O1W—H1WB	103 (2)	H15A—C15—H15B	107.3
C1—O1—H1A	109.5	O6—C16—O5	119.4 (2)
C8—O2—Ce1	99.57 (13)	O6—C16—C15	122.36 (19)
Ce1—O2W—H2WA	118.0 (19)	O5—C16—C15	118.19 (19)
Ce1—O2W—H2WB	130 (2)	O6—C16—Ce1	57.90 (11)
H2WA—O2W—H2WB	104 (2)	O5—C16—Ce1	63.27 (11)
C8—O3—Ce1i	151.47 (14)	C15—C16—Ce1	164.79 (18)
O3i—Ce1—O2—C8	−9.94 (16)	O1W—Ce1—O9—N1	73.79 (13)
O5ii—Ce1—O2—C8	169.33 (16)	O6—Ce1—O9—N1	64.17 (18)
O2W—Ce1—O2—C8	64.29 (14)	O5—Ce1—O9—N1	128.49 (13)
O1W—Ce1—O2—C8	−141.93 (14)	O8—Ce1—O9—N1	2.46 (12)
O6—Ce1—O2—C8	−77.35 (15)	O3—Ce1—O9—N1	−91.75 (14)
O9—Ce1—O2—C8	117.92 (14)	C16—Ce1—O9—N1	102.24 (14)
O5—Ce1—O2—C8	−124.05 (15)	C6—C1—C2—C3	−0.1 (5)
O8—Ce1—O2—C8	69.7 (2)	O1—C1—C2—C3	179.4 (3)
O3—Ce1—O2—C8	−7.65 (13)	C1—C2—C3—C4	0.4 (4)
C16—Ce1—O2—C8	−101.13 (15)	C2—C3—C4—C5	−0.4 (4)
O3i—Ce1—O3—C8	−174.91 (17)	C2—C3—C4—C7	179.4 (2)
O5ii—Ce1—O3—C8	4.31 (15)	C3—C4—C5—C6	0.2 (5)
O2W—Ce1—O3—C8	−82.21 (13)	C7—C4—C5—C6	−179.7 (3)
O2—Ce1—O3—C8	7.49 (13)	C2—C1—C6—C5	−0.1 (5)
O1W—Ce1—O3—C8	124.99 (14)	O1—C1—C6—C5	−179.6 (3)
O6—Ce1—O3—C8	110.09 (14)	C4—C5—C6—C1	0.1 (6)
O9—Ce1—O3—C8	−81.81 (14)	C5—C4—C7—C8	57.1 (4)
O5—Ce1—O3—C8	65.30 (13)	C3—C4—C7—C8	−122.7 (3)
O8—Ce1—O3—C8	−139.93 (13)	Ce1—O2—C8—O3	14.3 (2)
C16—Ce1—O3—C8	88.99 (13)	Ce1—O2—C8—C7	−163.7 (2)
O3i—Ce1—O3—Ce1i	0.0	Ce1i—O3—C8—O2	176.4 (2)
O5ii—Ce1—O3—Ce1i	179.23 (5)	Ce1—O3—C8—O2	−13.1 (2)
O2W—Ce1—O3—Ce1i	92.70 (8)	Ce1i—O3—C8—C7	−5.7 (5)
O2—Ce1—O3—Ce1i	−177.60 (10)	Ce1—O3—C8—C7	164.8 (2)
O1W—Ce1—O3—Ce1i	−60.09 (12)	C4—C7—C8—O2	24.1 (4)
O6—Ce1—O3—Ce1i	−75.00 (7)	C4—C7—C8—O3	−153.9 (2)
O9—Ce1—O3—Ce1i	93.10 (8)	C14—C9—C10—C11	−1.7 (5)
O5—Ce1—O3—Ce1i	−119.79 (7)	O4—C9—C10—C11	175.2 (3)
O8—Ce1—O3—Ce1i	34.98 (9)	C9—C10—C11—C12	0.2 (6)
C16—Ce1—O3—Ce1i	−96.10 (7)	C10—C11—C12—C13	1.4 (5)
O3i—Ce1—O5—C16	10.28 (14)	C10—C11—C12—C15	−174.3 (3)
O5ii—Ce1—O5—C16	−169.91 (16)	C11—C12—C13—C14	−1.5 (5)
O2W—Ce1—O5—C16	127.78 (12)	C15—C12—C13—C14	174.0 (3)
O2—Ce1—O5—C16	114.18 (13)	C10—C9—C14—C13	1.5 (5)
O1W—Ce1—O5—C16	−78.44 (13)	O4—C9—C14—C13	−175.2 (3)
O6—Ce1—O5—C16	8.32 (12)	C12—C13—C14—C9	0.1 (5)
O9—Ce1—O5—C16	−136.31 (12)	C11—C12—C15—C16	−127.4 (3)
O8—Ce1—O5—C16	−75.42 (14)	C13—C12—C15—C16	57.1 (4)
O3—Ce1—O5—C16	71.84 (12)	Ce1—O6—C16—O5	15.6 (2)
O3i—Ce1—O5—Ce1ii	−179.81 (5)	Ce1—O6—C16—C15	−162.0 (2)
O5ii—Ce1—O5—Ce1ii	0.0	Ce1ii—O5—C16—O6	−177.51 (17)
O2W—Ce1—O5—Ce1ii	−62.31 (11)	Ce1—O5—C16—O6	−14.8 (2)
O2—Ce1—O5—Ce1ii	−75.91 (7)	Ce1ii—O5—C16—C15	0.2 (4)
O1W—Ce1—O5—Ce1ii	91.47 (8)	Ce1—O5—C16—C15	162.9 (2)
O6—Ce1—O5—Ce1ii	178.23 (10)	Ce1ii—O5—C16—Ce1	−162.7 (3)
O9—Ce1—O5—Ce1ii	33.60 (9)	C12—C15—C16—O6	12.9 (4)
O8—Ce1—O5—Ce1ii	94.49 (9)	C12—C15—C16—O5	−164.8 (2)
O3—Ce1—O5—Ce1ii	−118.25 (7)	C12—C15—C16—Ce1	−73.2 (6)
C16—Ce1—O5—Ce1ii	169.91 (16)	O3i—Ce1—C16—O6	−6.21 (14)
O3i—Ce1—O6—C16	173.39 (15)	O5ii—Ce1—C16—O6	173.67 (14)
O5ii—Ce1—O6—C16	−6.77 (15)	O2W—Ce1—C16—O6	73.49 (19)
O2W—Ce1—O6—C16	−137.39 (13)	O2—Ce1—C16—O6	104.60 (14)
O2—Ce1—O6—C16	−73.33 (14)	O1W—Ce1—C16—O6	−103.72 (15)
O1W—Ce1—O6—C16	67.94 (14)	O9—Ce1—C16—O6	−134.01 (14)
O9—Ce1—O6—C16	77.67 (18)	O5—Ce1—C16—O6	164.8 (2)
O5—Ce1—O6—C16	−8.44 (12)	O8—Ce1—C16—O6	−70.02 (15)
O8—Ce1—O6—C16	123.27 (14)	O3—Ce1—C16—O6	56.13 (14)
O3—Ce1—O6—C16	−120.32 (14)	O3i—Ce1—C16—O5	−170.98 (12)
O7—N1—O8—Ce1	−176.2 (2)	O5ii—Ce1—C16—O5	8.91 (14)
O9—N1—O8—Ce1	4.2 (2)	O2W—Ce1—C16—O5	−91.28 (16)
O3i—Ce1—O8—N1	154.13 (15)	O2—Ce1—C16—O5	−60.17 (12)
O5ii—Ce1—O8—N1	−25.22 (15)	O1W—Ce1—C16—O5	91.51 (12)
O2W—Ce1—O8—N1	67.94 (13)	O6—Ce1—C16—O5	−164.8 (2)
O2—Ce1—O8—N1	62.56 (19)	O9—Ce1—C16—O5	61.22 (15)
O1W—Ce1—O8—N1	−95.12 (14)	O8—Ce1—C16—O5	125.22 (12)
O6—Ce1—O8—N1	−154.27 (12)	O3—Ce1—C16—O5	−108.63 (12)
O9—Ce1—O8—N1	−2.44 (12)	O3i—Ce1—C16—C15	89.6 (6)
O5—Ce1—O8—N1	−98.19 (14)	O5ii—Ce1—C16—C15	−90.5 (6)
O3—Ce1—O8—N1	120.41 (13)	O2W—Ce1—C16—C15	169.3 (5)
C16—Ce1—O8—N1	−128.67 (13)	O2—Ce1—C16—C15	−159.6 (6)
O7—N1—O9—Ce1	176.07 (19)	O1W—Ce1—C16—C15	−7.9 (5)
O8—N1—O9—Ce1	−4.3 (2)	O6—Ce1—C16—C15	95.8 (6)
O3i—Ce1—O9—N1	−20.48 (15)	O9—Ce1—C16—C15	−38.2 (6)
O5ii—Ce1—O9—N1	160.03 (15)	O5—Ce1—C16—C15	−99.5 (6)
O2W—Ce1—O9—N1	−91.36 (14)	O8—Ce1—C16—C15	25.8 (6)
O2—Ce1—O9—N1	−148.66 (12)	O3—Ce1—C16—C15	151.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ii	0.85 (2)	1.90 (2)	2.693 (2)	156 (3)
O1W—H1WB···O7iii	0.82 (2)	2.46 (2)	3.197 (3)	150 (3)
O1W—H1WB···O8iii	0.82 (2)	2.51 (2)	3.272 (3)	156 (3)
O2W—H2WA···O6i	0.83 (2)	1.91 (2)	2.721 (2)	165 (3)
O2W—H2WB···O4iv	0.84 (2)	1.95 (2)	2.783 (3)	175 (3)
O3W—H3WA···O4ii	0.85 (2)	2.58 (2)	3.352 (4)	152 (3)
O4—H4A···O1v	0.82	1.83	2.649 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2i	0.85 (2)	1.90 (2)	2.693 (2)	156 (3)
O1W—H1WB⋯O7ii	0.82 (2)	2.46 (2)	3.197 (3)	150 (3)
O1W—H1WB⋯O8ii	0.82 (2)	2.51 (2)	3.272 (3)	156 (3)
O2W—H2WA⋯O6iii	0.83 (2)	1.91 (2)	2.721 (2)	165 (3)
O2W—H2WB⋯O4iv	0.84 (2)	1.95 (2)	2.783 (3)	175 (3)
O3W—H3WA⋯O4i	0.85 (2)	2.58 (2)	3.352 (4)	152 (3)
O4—H4A⋯O1v	0.82	1.83	2.649 (3)	173

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