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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.
Supporting information
CCDC reference: 289920
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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(µ
3-3-carboxypyrazole-5-carboxylato)(3-carboxypyrazole-
5-carboxylato-
κO)(µ
2-pyrazole-3,5-dicarboxylato)dicerium]
top
Crystal data top
[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) Å3 | 0.15 × 0.07 × 0.07 mm |
Z = 4 | |
Data collection top
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 top
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)] = 0.029 | Hydrogen site location: geom and difmap for H2O |
wR(F2) = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0194P)2 + 12.7824P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Ce1—O2i | 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—O3ii | 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—Ce1iii | 2.391 (2) | N5—N5v | 1.342 (7) |
O3—C5 | 1.220 (4) | N5—H5N | 0.8600 |
O3—Ce1iv | 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—C12v | 1.376 (5) |
O12—H12A | 0.80 (3) | C13—H13 | 0.9300 |
| | | |
O2i—Ce1—O5 | 75.96 (9) | N2—N1—C1 | 105.6 (3) |
O2i—Ce1—O12 | 82.05 (12) | N2—N1—Ce1 | 134.9 (2) |
O5—Ce1—O12 | 73.43 (12) | C1—N1—Ce1 | 118.3 (2) |
O2i—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 |
O2i—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) |
O2i—Ce1—O13 | 69.02 (10) | C12—N5—N5v | 108.3 (2) |
O5—Ce1—O13 | 74.54 (11) | C12—N5—H5N | 125.9 |
O12—Ce1—O13 | 141.00 (12) | N5v—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) |
O2i—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) |
O2i—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) |
O2i—Ce1—O3ii | 85.69 (9) | N3—C6—C7 | 106.3 (3) |
O5—Ce1—O3ii | 148.06 (10) | N3—C6—C9 | 121.8 (3) |
O12—Ce1—O3ii | 130.13 (10) | C7—C6—C9 | 131.8 (4) |
O11—Ce1—O3ii | 64.69 (10) | C6—C7—C8 | 104.8 (3) |
O1—Ce1—O3ii | 75.20 (8) | C6—C7—H6 | 127.6 |
O13—Ce1—O3ii | 74.55 (9) | C8—C7—H6 | 127.6 |
O9—Ce1—O3ii | 69.05 (8) | N4—C8—C7 | 111.5 (3) |
N1—Ce1—O3ii | 130.22 (9) | N4—C8—C10 | 121.7 (3) |
C4—O1—Ce1 | 124.0 (2) | C7—C8—C10 | 126.7 (4) |
C4—O2—Ce1iii | 158.9 (3) | O5—C9—O6 | 125.0 (4) |
C5—O3—Ce1iv | 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—C12v | 105.0 (5) |
Ce1—O13—H13B | 109.5 | C12—C13—H13 | 127.5 |
H13A—O13—H13B | 106.8 | C12v—C13—H13 | 127.5 |
| | | |
O2i—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) | Ce1iii—O2—C4—O1 | 95.8 (8) |
N1—Ce1—O1—C4 | −14.8 (3) | Ce1iii—O2—C4—C1 | −85.5 (8) |
O3ii—Ce1—O1—C4 | 139.6 (3) | Ce1—O1—C4—O2 | −165.4 (3) |
O2i—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) | Ce1iv—O3—C5—O4 | 24.8 (6) |
N1—Ce1—O5—C9 | −30.3 (11) | Ce1iv—O3—C5—C3 | −155.3 (3) |
O3ii—Ce1—O5—C9 | −169.2 (10) | N2—C3—C5—O3 | 174.0 (3) |
O2i—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) |
O3ii—Ce1—O9—C11 | −170.6 (4) | N3—N4—C8—C7 | −0.6 (4) |
O2i—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) |
O3ii—Ce1—N1—N2 | 144.4 (3) | N3—C6—C9—O6 | −166.7 (4) |
O2i—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) |
O3ii—Ce1—N1—C1 | −21.2 (3) | N5v—N5—C12—C13 | 0.2 (6) |
C1—N1—N2—C3 | 0.4 (4) | N5v—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—C12v | −0.1 (2) |
Ce1—N1—C1—C4 | −10.0 (4) | C11—C12—C13—C12v | −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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O9iv | 0.82 | 1.70 | 2.515 (4) | 172 |
O4—H4···O10iv | 0.82 | 2.66 | 3.253 (4) | 131 |
O7—H7···O10vi | 0.82 | 1.96 | 2.760 (4) | 165 |
O11—H11B···O10i | 0.77 (3) | 2.34 (3) | 3.061 (5) | 157 (6) |
O11—H11A···N4iii | 0.80 (3) | 2.05 (3) | 2.816 (4) | 163 (5) |
O12—H12B···O10i | 0.80 (3) | 2.21 (3) | 2.994 (5) | 169 (6) |
O12—H12A···O6vii | 0.80 (3) | 1.97 (3) | 2.751 (4) | 164 (5) |
O13—H13A···O10viii | 0.82 | 2.43 | 3.174 (5) | 152 |
O13—H13B···O8ix | 0.82 | 2.12 | 2.884 (4) | 156 |
N2—H2N···O6 | 0.86 | 1.85 | 2.695 (4) | 165 |
N3—H3N···O1i | 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. |
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