Poly[hexa­aqua­tris(μ₃-3-carboxy­pyrazole-5-carboxyl­ato)(3-carboxy­pyrazole-5-carboxyl­ato-κO)(μ₂-pyrazole-3,5-dicarboxyl­ato)dicerium(III)]

In the title compound, [Ce₂(C₅H₂N₂O₄)(C₅H₃N₂O₄)₄(H₂O)₆]_n, each Ce atom is nine-coordinated by three water mol­ecules, four 3-carboxy­pyrazole-5-carboxyl­ate monoanions (two pairs of symmetry-related anions), and a pyrazole-3,5-dicarboxyl­ate dianion. Two symmetry-related Ce atoms are bridged by a pyrazole-3,5-dicarboxyl­ate dianion, which lies across a twofold rotation axis. There are two independent 3-carboxy­pyrazole-5-carboxyl­ate monoanions which differ in their coordination modes; one is monodentate and the other is tetra­dentate. The Ce atoms are bridged by both pyrazole-3,5-dicarboxyl­ate dianions and 3-carboxy­pyrazole-5-carboxyl­ate monoanions, generating a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.029
• wR factor = 0.060
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.01
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.09
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  O10     ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5N    ..  O5      ..       2.61 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.80(7), Rep     0.80(3) ......       2.33 su-Rat
              O12  -H12B    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.80(7), Rep     0.80(3) ......       2.33 su-Rat
              O12  -H12B    1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.20(7), Rep     2.21(3) ......       2.33 su-Rat
              H12B -O10     1.555   4.555

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

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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Poly[hexaaquatris(µ₃-3-carboxypyrazole-5-carboxylato)(3-carboxypyrazole- 5-carboxylato-κO)(µ₂-pyrazole-3,5-dicarboxylato)dicerium]

Crystal data

[Ce2(C5H2N2O4)(C5H3N2O4)4(H2O)6]	F(000) = 2279
Mr = 1162.80	Dx = 2.178 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 3147 reflections
a = 19.2347 (16) Å	θ = 2.0–25.1°
b = 13.2563 (11) Å	µ = 2.66 mm^−1
c = 16.7559 (15) Å	T = 298 K
β = 123.909 (1)°	Prism, colorless
V = 3545.8 (5) Å^3	0.15 × 0.07 × 0.07 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	3147 independent reflections
Radiation source: fine-focus sealed tube	2864 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −22→21
Tmin = 0.80, Tmax = 0.82	k = −15→14
9143 measured reflections	l = −19→19

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)] = 0.029	Hydrogen site location: geom and difmap for H2O
wR(F^2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0194P)^2 + 12.7824P] where P = (Fo^2 + 2Fc^2)/3
3147 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.74 e Å^−3
4 restraints	Δρmin = −0.39 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	Occ. (<1)
Ce1	0.221680 (12)	0.422684 (15)	0.268022 (15)	0.01723 (8)
O1	0.26909 (15)	0.25668 (19)	0.23560 (19)	0.0231 (6)
O2	0.24354 (17)	0.09614 (19)	0.1889 (2)	0.0281 (7)
O3	−0.13160 (16)	0.1174 (2)	−0.06959 (19)	0.0255 (6)
O4	−0.13944 (16)	0.2750 (2)	−0.0279 (2)	0.0358 (8)
H4	−0.1899	0.2657	−0.0657	0.054*
O5	0.08617 (17)	0.5070 (2)	0.1892 (2)	0.0413 (8)
O6	−0.04645 (17)	0.4800 (2)	0.0706 (2)	0.0368 (8)
O7	−0.07643 (19)	0.9691 (2)	0.1199 (3)	0.0389 (8)
H7	−0.1106	1.0135	0.1080	0.058*
O8	−0.1908 (2)	0.8733 (2)	0.0382 (3)	0.0477 (9)
O9	0.20838 (16)	0.2705 (2)	0.3604 (2)	0.0282 (7)
O10	0.18045 (18)	0.1158 (2)	0.3847 (3)	0.0450 (9)
O11	0.35006 (19)	0.4562 (2)	0.2637 (2)	0.0318 (7)
H11B	0.357 (3)	0.497 (3)	0.237 (4)	0.059 (19)*
H11A	0.391 (2)	0.422 (3)	0.293 (3)	0.048 (16)*
O12	0.1891 (2)	0.4860 (3)	0.1089 (2)	0.0439 (9)
H12B	0.219 (3)	0.526 (4)	0.106 (5)	0.08 (2)*
H12A	0.1436 (19)	0.488 (4)	0.060 (2)	0.034 (14)*
O13	0.20399 (19)	0.4716 (2)	0.4036 (2)	0.0367 (7)
H13A	0.2276	0.4298	0.4469	0.055*
H13B	0.2271	0.5258	0.4266	0.055*
N1	0.10629 (18)	0.2993 (2)	0.1371 (2)	0.0208 (7)
N2	0.02321 (18)	0.2998 (2)	0.0812 (2)	0.0200 (7)
H2N	−0.0072	0.3519	0.0716	0.024*
N3	0.0546 (2)	0.7138 (2)	0.1776 (2)	0.0243 (7)
H3N	0.1072	0.6996	0.2098	0.029*
N4	0.02511 (19)	0.8069 (2)	0.1687 (2)	0.0216 (7)
N5	0.0420 (2)	0.3238 (2)	0.2770 (3)	0.0344 (9)
H5N	0.0736	0.3763	0.2971	0.041*	0.50
C1	0.1292 (2)	0.2052 (3)	0.1322 (3)	0.0172 (8)
C2	0.0599 (2)	0.1445 (3)	0.0729 (3)	0.0208 (8)
H2	0.0592	0.0768	0.0580	0.025*
C3	−0.0078 (2)	0.2083 (3)	0.0410 (3)	0.0178 (8)
C4	0.2207 (2)	0.1836 (3)	0.1902 (3)	0.0191 (8)
C5	−0.0988 (2)	0.1947 (3)	−0.0245 (3)	0.0203 (8)
C6	−0.0065 (2)	0.6440 (3)	0.1308 (3)	0.0220 (8)
C7	−0.0811 (2)	0.6951 (3)	0.0889 (3)	0.0229 (9)
H6	−0.1349	0.6685	0.0515	0.027*
C8	−0.0584 (2)	0.7955 (3)	0.1147 (3)	0.0200 (8)
C9	0.0127 (2)	0.5358 (3)	0.1300 (3)	0.0250 (9)
C10	−0.1155 (3)	0.8820 (3)	0.0872 (3)	0.0256 (9)
C11	0.1582 (2)	0.2019 (3)	0.3511 (3)	0.0217 (9)
C12	0.0684 (2)	0.2278 (3)	0.2941 (3)	0.0208 (8)
C13	0.0000	0.1646 (4)	0.2500	0.0221 (12)
H13	0.0000	0.0944	0.2500	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ce1	0.01363 (12)	0.01182 (12)	0.01862 (13)	0.00032 (9)	0.00428 (9)	0.00064 (9)
O1	0.0140 (13)	0.0161 (14)	0.0309 (16)	0.0003 (11)	0.0074 (12)	−0.0036 (12)
O2	0.0236 (15)	0.0164 (14)	0.0375 (18)	0.0054 (12)	0.0128 (14)	0.0009 (13)
O3	0.0176 (14)	0.0219 (14)	0.0251 (16)	−0.0055 (12)	0.0046 (12)	−0.0079 (13)
O4	0.0124 (14)	0.0283 (16)	0.044 (2)	0.0017 (13)	0.0020 (14)	−0.0144 (15)
O5	0.0168 (16)	0.0260 (16)	0.055 (2)	0.0051 (13)	0.0037 (15)	−0.0088 (16)
O6	0.0222 (16)	0.0184 (15)	0.0422 (19)	0.0021 (13)	0.0010 (14)	−0.0053 (14)
O7	0.0349 (18)	0.0175 (15)	0.054 (2)	0.0031 (14)	0.0184 (17)	−0.0046 (15)
O8	0.0266 (19)	0.0287 (17)	0.071 (3)	0.0064 (14)	0.0166 (18)	0.0048 (17)
O9	0.0148 (14)	0.0273 (15)	0.0325 (17)	−0.0068 (12)	0.0071 (13)	0.0037 (13)
O10	0.0208 (16)	0.0223 (16)	0.074 (3)	0.0033 (13)	0.0153 (17)	0.0144 (17)
O11	0.0240 (17)	0.0292 (18)	0.040 (2)	0.0085 (14)	0.0168 (16)	0.0147 (15)
O12	0.0233 (19)	0.067 (3)	0.0249 (19)	−0.0081 (18)	0.0032 (16)	0.0140 (18)
O13	0.048 (2)	0.0271 (16)	0.0390 (19)	−0.0058 (15)	0.0271 (17)	−0.0040 (15)
N1	0.0103 (15)	0.0174 (16)	0.0257 (18)	0.0004 (13)	0.0044 (14)	−0.0025 (14)
N2	0.0107 (16)	0.0161 (16)	0.0236 (18)	0.0022 (13)	0.0036 (14)	−0.0017 (14)
N3	0.0161 (17)	0.0227 (18)	0.0278 (19)	−0.0004 (14)	0.0084 (15)	−0.0027 (15)
N4	0.0198 (17)	0.0174 (16)	0.0243 (18)	−0.0006 (14)	0.0102 (15)	−0.0019 (14)
N5	0.0257 (18)	0.0203 (18)	0.040 (2)	−0.0002 (15)	0.0079 (17)	−0.0001 (17)
C1	0.0129 (18)	0.0157 (19)	0.0166 (19)	0.0005 (15)	0.0043 (16)	−0.0026 (15)
C2	0.022 (2)	0.0166 (19)	0.023 (2)	−0.0005 (16)	0.0124 (18)	−0.0030 (16)
C3	0.0141 (19)	0.0189 (19)	0.017 (2)	−0.0034 (15)	0.0068 (16)	−0.0034 (16)
C4	0.018 (2)	0.017 (2)	0.021 (2)	0.0021 (16)	0.0100 (17)	0.0013 (16)
C5	0.0154 (19)	0.022 (2)	0.018 (2)	−0.0009 (16)	0.0062 (17)	0.0001 (17)
C6	0.020 (2)	0.019 (2)	0.024 (2)	0.0020 (16)	0.0107 (18)	−0.0003 (17)
C7	0.017 (2)	0.020 (2)	0.026 (2)	−0.0007 (16)	0.0088 (18)	−0.0012 (17)
C8	0.021 (2)	0.0196 (19)	0.020 (2)	0.0023 (16)	0.0120 (18)	0.0001 (17)
C9	0.015 (2)	0.022 (2)	0.029 (2)	0.0055 (17)	0.0070 (19)	0.0017 (18)
C10	0.030 (3)	0.020 (2)	0.027 (2)	0.0018 (18)	0.016 (2)	0.0010 (18)
C11	0.017 (2)	0.020 (2)	0.025 (2)	−0.0031 (16)	0.0094 (18)	−0.0012 (17)
C12	0.0158 (19)	0.021 (2)	0.022 (2)	−0.0021 (16)	0.0081 (17)	−0.0022 (17)
C13	0.017 (3)	0.018 (3)	0.027 (3)	0.000	0.010 (3)	0.000

Geometric parameters (Å, º)

Ce1—O2^i	2.391 (2)	O13—H13A	0.8200
Ce1—O5	2.438 (3)	O13—H13B	0.8203
Ce1—O12	2.519 (3)	N1—N2	1.327 (4)
Ce1—O11	2.550 (3)	N1—C1	1.341 (5)
Ce1—O1	2.554 (2)	N2—C3	1.354 (4)
Ce1—O13	2.560 (3)	N2—H2N	0.8601
Ce1—O9	2.641 (3)	N3—N4	1.331 (4)
Ce1—N1	2.642 (3)	N3—C6	1.351 (5)
Ce1—O3^ii	2.661 (3)	N3—H3N	0.8600
O1—C4	1.262 (4)	N4—C8	1.342 (5)
O2—C4	1.244 (4)	N5—C12	1.340 (5)
O2—Ce1^iii	2.391 (2)	N5—N5^v	1.342 (7)
O3—C5	1.220 (4)	N5—H5N	0.8600
O3—Ce1^iv	2.661 (3)	C1—C2	1.390 (5)
O4—C5	1.303 (4)	C1—C4	1.488 (5)
O4—H4	0.8200	C2—C3	1.386 (5)
O5—C9	1.250 (5)	C2—H2	0.9300
O6—C9	1.253 (5)	C3—C5	1.470 (5)
O7—C10	1.319 (5)	C6—C7	1.374 (5)
O7—H7	0.8200	C6—C9	1.484 (5)
O8—C10	1.208 (5)	C7—C8	1.391 (5)
O9—C11	1.269 (4)	C7—H6	0.9300
O10—C11	1.240 (5)	C8—C10	1.473 (5)
O11—H11B	0.77 (3)	C11—C12	1.475 (5)
O11—H11A	0.80 (3)	C12—C13	1.376 (5)
O12—H12B	0.80 (3)	C13—C12^v	1.376 (5)
O12—H12A	0.80 (3)	C13—H13	0.9300
O2^i—Ce1—O5	75.96 (9)	N2—N1—C1	105.6 (3)
O2^i—Ce1—O12	82.05 (12)	N2—N1—Ce1	134.9 (2)
O5—Ce1—O12	73.43 (12)	C1—N1—Ce1	118.3 (2)
O2^i—Ce1—O11	74.28 (10)	N1—N2—C3	111.7 (3)
O5—Ce1—O11	131.65 (11)	N1—N2—H2N	124.2
O12—Ce1—O11	65.45 (11)	C3—N2—H2N	124.2
O2^i—Ce1—O1	145.08 (9)	N4—N3—C6	113.0 (3)
O5—Ce1—O1	132.87 (9)	N4—N3—H3N	123.5
O12—Ce1—O1	88.24 (11)	C6—N3—H3N	123.5
O11—Ce1—O1	71.18 (9)	N3—N4—C8	104.3 (3)
O2^i—Ce1—O13	69.02 (10)	C12—N5—N5^v	108.3 (2)
O5—Ce1—O13	74.54 (11)	C12—N5—H5N	125.9
O12—Ce1—O13	141.00 (12)	N5^v—N5—H5N	125.9
O11—Ce1—O13	126.26 (10)	N1—C1—C2	111.4 (3)
O1—Ce1—O13	130.29 (9)	N1—C1—C4	116.6 (3)
O2^i—Ce1—O9	131.31 (9)	C2—C1—C4	131.9 (3)
O5—Ce1—O9	104.10 (10)	C3—C2—C1	104.0 (3)
O12—Ce1—O9	145.77 (11)	C3—C2—H2	128.0
O11—Ce1—O9	124.17 (9)	C1—C2—H2	128.0
O1—Ce1—O9	68.22 (9)	N2—C3—C2	107.3 (3)
O13—Ce1—O9	64.50 (9)	N2—C3—C5	119.5 (3)
O2^i—Ce1—N1	144.09 (10)	C2—C3—C5	133.2 (3)
O5—Ce1—N1	71.64 (9)	O2—C4—O1	125.3 (3)
O12—Ce1—N1	74.32 (11)	O2—C4—C1	117.9 (3)
O11—Ce1—N1	117.54 (10)	O1—C4—C1	116.8 (3)
O1—Ce1—N1	61.59 (8)	O3—C5—O4	124.7 (3)
O13—Ce1—N1	115.30 (10)	O3—C5—C3	123.7 (3)
O9—Ce1—N1	72.68 (9)	O4—C5—C3	111.6 (3)
O2^i—Ce1—O3^ii	85.69 (9)	N3—C6—C7	106.3 (3)
O5—Ce1—O3^ii	148.06 (10)	N3—C6—C9	121.8 (3)
O12—Ce1—O3^ii	130.13 (10)	C7—C6—C9	131.8 (4)
O11—Ce1—O3^ii	64.69 (10)	C6—C7—C8	104.8 (3)
O1—Ce1—O3^ii	75.20 (8)	C6—C7—H6	127.6
O13—Ce1—O3^ii	74.55 (9)	C8—C7—H6	127.6
O9—Ce1—O3^ii	69.05 (8)	N4—C8—C7	111.5 (3)
N1—Ce1—O3^ii	130.22 (9)	N4—C8—C10	121.7 (3)
C4—O1—Ce1	124.0 (2)	C7—C8—C10	126.7 (4)
C4—O2—Ce1^iii	158.9 (3)	O5—C9—O6	125.0 (4)
C5—O3—Ce1^iv	133.5 (2)	O5—C9—C6	117.7 (4)
C5—O4—H4	109.5	O6—C9—C6	117.2 (3)
C9—O5—Ce1	164.4 (3)	O8—C10—O7	123.8 (4)
C10—O7—H7	109.5	O8—C10—C8	122.7 (4)
C11—O9—Ce1	142.2 (2)	O7—C10—C8	113.6 (3)
Ce1—O11—H11B	129 (4)	O10—C11—O9	123.9 (3)
Ce1—O11—H11A	122 (4)	O10—C11—C12	119.4 (3)
H11B—O11—H11A	109 (5)	O9—C11—C12	116.7 (3)
Ce1—O12—H12B	122 (5)	N5—C12—C13	109.2 (3)
Ce1—O12—H12A	125 (3)	N5—C12—C11	121.7 (3)
H12B—O12—H12A	109 (6)	C13—C12—C11	129.1 (4)
Ce1—O13—H13A	109.5	C12—C13—C12^v	105.0 (5)
Ce1—O13—H13B	109.5	C12—C13—H13	127.5
H13A—O13—H13B	106.8	C12^v—C13—H13	127.5
O2^i—Ce1—O1—C4	−161.3 (3)	C4—C1—C2—C3	179.1 (4)
O5—Ce1—O1—C4	−22.6 (3)	N1—N2—C3—C2	−0.2 (4)
O12—Ce1—O1—C4	−87.9 (3)	N1—N2—C3—C5	−179.1 (3)
O11—Ce1—O1—C4	−152.5 (3)	C1—C2—C3—N2	0.0 (4)
O13—Ce1—O1—C4	85.4 (3)	C1—C2—C3—C5	178.7 (4)
O9—Ce1—O1—C4	66.6 (3)	Ce1^iii—O2—C4—O1	95.8 (8)
N1—Ce1—O1—C4	−14.8 (3)	Ce1^iii—O2—C4—C1	−85.5 (8)
O3^ii—Ce1—O1—C4	139.6 (3)	Ce1—O1—C4—O2	−165.4 (3)
O2^i—Ce1—O5—C9	134.0 (11)	Ce1—O1—C4—C1	15.8 (4)
O12—Ce1—O5—C9	48.3 (11)	N1—C1—C4—O2	178.2 (3)
O11—Ce1—O5—C9	80.6 (11)	C2—C1—C4—O2	−0.7 (6)
O1—Ce1—O5—C9	−23.1 (12)	N1—C1—C4—O1	−3.0 (5)
O13—Ce1—O5—C9	−154.3 (11)	C2—C1—C4—O1	178.2 (4)
O9—Ce1—O5—C9	−96.3 (11)	Ce1^iv—O3—C5—O4	24.8 (6)
N1—Ce1—O5—C9	−30.3 (11)	Ce1^iv—O3—C5—C3	−155.3 (3)
O3^ii—Ce1—O5—C9	−169.2 (10)	N2—C3—C5—O3	174.0 (3)
O2^i—Ce1—O9—C11	125.7 (4)	C2—C3—C5—O3	−4.5 (7)
O5—Ce1—O9—C11	42.2 (4)	N2—C3—C5—O4	−6.2 (5)
O12—Ce1—O9—C11	−39.0 (5)	C2—C3—C5—O4	175.3 (4)
O11—Ce1—O9—C11	−135.0 (4)	N4—N3—C6—C7	−0.4 (4)
O1—Ce1—O9—C11	−88.7 (4)	N4—N3—C6—C9	178.9 (3)
O13—Ce1—O9—C11	107.1 (4)	N3—C6—C7—C8	−0.1 (4)
N1—Ce1—O9—C11	−23.1 (4)	C9—C6—C7—C8	−179.2 (4)
O3^ii—Ce1—O9—C11	−170.6 (4)	N3—N4—C8—C7	−0.6 (4)
O2^i—Ce1—N1—N2	−35.1 (4)	N3—N4—C8—C10	−179.6 (3)
O5—Ce1—N1—N2	−8.5 (3)	C6—C7—C8—N4	0.4 (5)
O12—Ce1—N1—N2	−85.9 (3)	C6—C7—C8—C10	179.4 (4)
O11—Ce1—N1—N2	−136.6 (3)	Ce1—O5—C9—O6	39.5 (14)
O1—Ce1—N1—N2	177.5 (4)	Ce1—O5—C9—C6	−141.6 (9)
O13—Ce1—N1—N2	53.6 (4)	N3—C6—C9—O5	14.3 (6)
O9—Ce1—N1—N2	103.3 (3)	C7—C6—C9—O5	−166.7 (4)
O3^ii—Ce1—N1—N2	144.4 (3)	N3—C6—C9—O6	−166.7 (4)
O2^i—Ce1—N1—C1	159.3 (2)	C7—C6—C9—O6	12.3 (7)
O5—Ce1—N1—C1	−174.1 (3)	N4—C8—C10—O8	179.7 (4)
O12—Ce1—N1—C1	108.6 (3)	C7—C8—C10—O8	0.8 (7)
O11—Ce1—N1—C1	57.8 (3)	N4—C8—C10—O7	0.6 (5)
O1—Ce1—N1—C1	11.9 (3)	C7—C8—C10—O7	−178.2 (4)
O13—Ce1—N1—C1	−112.0 (3)	Ce1—O9—C11—O10	143.4 (4)
O9—Ce1—N1—C1	−62.2 (3)	Ce1—O9—C11—C12	−34.8 (6)
O3^ii—Ce1—N1—C1	−21.2 (3)	N5^v—N5—C12—C13	0.2 (6)
C1—N1—N2—C3	0.4 (4)	N5^v—N5—C12—C11	179.4 (4)
Ce1—N1—N2—C3	−166.5 (3)	O10—C11—C12—N5	162.7 (4)
C6—N3—N4—C8	0.6 (4)	O9—C11—C12—N5	−19.1 (6)
N2—N1—C1—C2	−0.3 (4)	O10—C11—C12—C13	−18.3 (6)
Ce1—N1—C1—C2	169.1 (2)	O9—C11—C12—C13	159.9 (3)
N2—N1—C1—C4	−179.4 (3)	N5—C12—C13—C12^v	−0.1 (2)
Ce1—N1—C1—C4	−10.0 (4)	C11—C12—C13—C12^v	−179.2 (5)
N1—C1—C2—C3	0.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O9^iv	0.82	1.70	2.515 (4)	172
O4—H4···O10^iv	0.82	2.66	3.253 (4)	131
O7—H7···O10^vi	0.82	1.96	2.760 (4)	165
O11—H11B···O10^i	0.77 (3)	2.34 (3)	3.061 (5)	157 (6)
O11—H11A···N4^iii	0.80 (3)	2.05 (3)	2.816 (4)	163 (5)
O12—H12B···O10^i	0.80 (3)	2.21 (3)	2.994 (5)	169 (6)
O12—H12A···O6^vii	0.80 (3)	1.97 (3)	2.751 (4)	164 (5)
O13—H13A···O10^viii	0.82	2.43	3.174 (5)	152
O13—H13B···O8^ix	0.82	2.12	2.884 (4)	156
N2—H2N···O6	0.86	1.85	2.695 (4)	165
N3—H3N···O1^i	0.86	2.16	2.904 (4)	145
N5—H5N···O13	0.86	2.46	3.266 (4)	156
N5—H5N···O5	0.86	2.61	3.190 (5)	126

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