The nine-coordinate cerium(III) complex with guanidinium as cation, (CH6N3)3[Ce(C7H3NO4)3]·3H2O or (GH)3[Ce(pydc)3]·3H2O (G = guanidine and pydc = pyridine-2,6-dicarboxylate), shows a tricapped trigonal-prismatic coordination. Hydrogen-bonding interactions between the cation, anion and water molecules result in a three-dimensional supramolecular network structure.
Supporting information
CCDC reference: 294822
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.087
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D H2WB .. H5B .. 2.07 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ce1 - O1 .. 6.32 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ce1 - O5 .. 5.70 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ce1 - O7 .. 6.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ce1 - O9 .. 6.77 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ce1 - N3 .. 5.71 su
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C12 - C14 ... 1.53 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C19 - C21 ... 1.53 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Tris(guanidinium)
tris(pyridine-2,6-dicarboxylato-
κ3O,
N,
O)cerate(III)
trihydrate
top
Crystal data top
(CH6N3)3[Ce(C7H3NO4)3]·3H2O | F(000) = 3512 |
Mr = 869.74 | Dx = 1.723 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1024 reflections |
a = 19.0405 (7) Å | θ = 2.2–29.9° |
b = 17.1308 (7) Å | µ = 1.45 mm−1 |
c = 20.5597 (8) Å | T = 120 K |
V = 6706.1 (5) Å3 | Prism, red |
Z = 8 | 0.34 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 7688 independent reflections |
Radiation source: fine-focus sealed tube | 4221 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −20→24 |
Tmin = 0.639, Tmax = 0.761 | k = −22→20 |
50286 measured reflections | l = −26→26 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0245P)2 + 5.255P] where P = (Fo2 + 2Fc2)/3 |
7688 reflections | (Δ/σ)max = 0.003 |
469 parameters | Δρmax = 1.21 e Å−3 |
159 restraints | Δρmin = −0.66 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 | |
Ce1 | 0.499586 (12) | 0.503779 (9) | 0.749149 (9) | 0.01200 (6) | |
O1 | 0.53471 (15) | 0.39462 (15) | 0.67103 (12) | 0.0243 (6) | |
O2 | 0.60950 (15) | 0.34582 (16) | 0.59744 (13) | 0.0284 (7) | |
O3 | 0.58474 (15) | 0.60196 (15) | 0.79313 (13) | 0.0256 (6) | |
O4 | 0.69320 (15) | 0.64131 (17) | 0.81889 (14) | 0.0338 (7) | |
O5 | 0.55417 (14) | 0.43828 (16) | 0.84534 (12) | 0.0254 (6) | |
O6 | 0.54119 (14) | 0.37406 (16) | 0.93911 (12) | 0.0253 (6) | |
O7 | 0.38768 (14) | 0.45675 (16) | 0.69524 (12) | 0.0247 (6) | |
O8 | 0.29705 (15) | 0.37447 (16) | 0.68498 (13) | 0.0278 (7) | |
O9 | 0.42959 (14) | 0.55827 (15) | 0.84277 (12) | 0.0227 (6) | |
O10 | 0.36053 (16) | 0.64856 (17) | 0.88923 (13) | 0.0339 (7) | |
O11 | 0.50532 (14) | 0.56648 (15) | 0.63918 (11) | 0.0226 (6) | |
O12 | 0.46157 (16) | 0.64506 (17) | 0.56259 (13) | 0.0312 (7) | |
N1 | 0.63210 (17) | 0.49272 (17) | 0.71497 (14) | 0.0191 (7) | |
N2 | 0.43523 (17) | 0.38251 (17) | 0.79889 (15) | 0.0204 (7) | |
N3 | 0.42802 (17) | 0.63223 (18) | 0.73023 (15) | 0.0219 (7) | |
C1 | 0.6525 (2) | 0.4400 (2) | 0.67057 (17) | 0.0200 (8) | |
C2 | 0.7210 (2) | 0.4354 (2) | 0.64877 (19) | 0.0236 (9) | |
H2A | 0.7339 | 0.3988 | 0.6176 | 0.028* | |
C3 | 0.7702 (2) | 0.4868 (2) | 0.67450 (19) | 0.0263 (9) | |
H3A | 0.8166 | 0.4855 | 0.6604 | 0.032* | |
C4 | 0.7493 (2) | 0.5400 (2) | 0.72137 (19) | 0.0246 (8) | |
H4A | 0.7817 | 0.5739 | 0.7400 | 0.029* | |
C5 | 0.6801 (2) | 0.5420 (2) | 0.73997 (18) | 0.0216 (8) | |
C6 | 0.5953 (2) | 0.3885 (2) | 0.64418 (18) | 0.0215 (8) | |
C7 | 0.6510 (2) | 0.6003 (2) | 0.78838 (18) | 0.0198 (8) | |
C8 | 0.4586 (2) | 0.3498 (2) | 0.85416 (18) | 0.0232 (9) | |
C9 | 0.4266 (2) | 0.2857 (2) | 0.8818 (2) | 0.0286 (10) | |
H9A | 0.4425 | 0.2657 | 0.9212 | 0.034* | |
C10 | 0.3703 (2) | 0.2516 (2) | 0.8498 (2) | 0.0317 (10) | |
H10A | 0.3495 | 0.2067 | 0.8665 | 0.038* | |
C11 | 0.3454 (2) | 0.2844 (2) | 0.7932 (2) | 0.0267 (9) | |
H11A | 0.3075 | 0.2627 | 0.7710 | 0.032* | |
C12 | 0.3789 (2) | 0.3517 (2) | 0.77009 (18) | 0.0220 (8) | |
C13 | 0.5227 (2) | 0.3902 (2) | 0.88269 (19) | 0.0223 (9) | |
C14 | 0.3521 (2) | 0.3969 (2) | 0.71103 (18) | 0.0203 (8) | |
C15 | 0.4248 (2) | 0.6642 (2) | 0.67147 (18) | 0.0216 (8) | |
C16 | 0.3856 (2) | 0.7308 (2) | 0.65830 (19) | 0.0271 (9) | |
H16A | 0.3835 | 0.7513 | 0.6165 | 0.033* | |
C17 | 0.3494 (2) | 0.7658 (2) | 0.7095 (2) | 0.0282 (9) | |
H17A | 0.3235 | 0.8111 | 0.7025 | 0.034* | |
C18 | 0.3526 (2) | 0.7324 (2) | 0.7710 (2) | 0.0256 (9) | |
H18A | 0.3289 | 0.7546 | 0.8059 | 0.031* | |
C19 | 0.3918 (2) | 0.6656 (2) | 0.77900 (17) | 0.0197 (8) | |
C20 | 0.4671 (2) | 0.6226 (2) | 0.61913 (18) | 0.0214 (8) | |
C21 | 0.3938 (2) | 0.6211 (2) | 0.84370 (18) | 0.0221 (9) | |
N7 | 0.55469 (18) | 0.63682 (18) | 0.93325 (16) | 0.0283 (8) | |
H7A | 0.5500 | 0.6167 | 0.9713 | 0.034* | |
H7B | 0.5796 | 0.6135 | 0.9043 | 0.034* | |
N8 | 0.48545 (18) | 0.73921 (18) | 0.96340 (15) | 0.0275 (8) | |
H8A | 0.4809 | 0.7189 | 1.0014 | 0.033* | |
H8B | 0.4651 | 0.7827 | 0.9545 | 0.033* | |
N9 | 0.53257 (19) | 0.73584 (19) | 0.86086 (15) | 0.0270 (8) | |
H9B | 0.5135 | 0.7801 | 0.8519 | 0.032* | |
H9C | 0.5576 | 0.7123 | 0.8321 | 0.032* | |
C23 | 0.5234 (2) | 0.7039 (2) | 0.91916 (19) | 0.0239 (9) | |
O2W | 0.71557 (17) | 0.55637 (18) | 0.98229 (15) | 0.0423 (8) | |
H2WA | 0.6772 | 0.5419 | 1.0007 | 0.051* | |
H2WB | 0.7106 | 0.5396 | 0.9431 | 0.051* | |
O3W | 0.69337 (15) | 0.45249 (16) | 0.88277 (13) | 0.0301 (7) | |
H3WB | 0.7261 | 0.4369 | 0.8570 | 0.036* | |
H3WA | 0.6507 | 0.4457 | 0.8704 | 0.036* | |
O1W | 0.58721 (16) | 0.50024 (16) | 1.02614 (14) | 0.0340 (7) | |
H1WA | 0.5777 | 0.4848 | 1.0649 | 0.041* | |
H1WB | 0.5867 | 0.4615 | 0.9995 | 0.041* | |
N4 | 0.38351 (19) | 0.4519 (2) | 0.45575 (16) | 0.0346 (9) | |
H4B | 0.3443 | 0.4700 | 0.4416 | 0.041* | |
H4C | 0.4136 | 0.4329 | 0.4289 | 0.041* | |
N5 | 0.35217 (19) | 0.4818 (2) | 0.56048 (17) | 0.0343 (9) | |
H5A | 0.3616 | 0.4824 | 0.6014 | 0.041* | |
H5B | 0.3128 | 0.5002 | 0.5467 | 0.041* | |
N6 | 0.45828 (19) | 0.4247 (2) | 0.53930 (16) | 0.0297 (8) | |
H6A | 0.4684 | 0.4248 | 0.5801 | 0.036* | |
H6B | 0.4877 | 0.4060 | 0.5116 | 0.036* | |
C22 | 0.3976 (2) | 0.4531 (2) | 0.51924 (19) | 0.0251 (9) | |
N10 | 0.2257 (2) | 0.2071 (2) | 0.48981 (18) | 0.0422 (11) | |
H10B | 0.2449 | 0.1631 | 0.4991 | 0.051* | |
H10C | 0.1997 | 0.2114 | 0.4558 | 0.051* | |
N11 | 0.2074 (2) | 0.3363 (2) | 0.51206 (17) | 0.0399 (10) | |
H11B | 0.1820 | 0.3404 | 0.4777 | 0.048* | |
H11C | 0.2142 | 0.3763 | 0.5365 | 0.048* | |
N12 | 0.27652 (19) | 0.2616 (2) | 0.57991 (16) | 0.0309 (8) | |
H12A | 0.2957 | 0.2176 | 0.5893 | 0.037* | |
H12B | 0.2834 | 0.3015 | 0.6045 | 0.037* | |
C24 | 0.2363 (2) | 0.2679 (3) | 0.5275 (2) | 0.0311 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ce1 | 0.01043 (9) | 0.01541 (9) | 0.01016 (9) | −0.00042 (9) | 0.00060 (8) | 0.00015 (8) |
O1 | 0.0203 (16) | 0.0259 (15) | 0.0267 (14) | −0.0041 (12) | 0.0032 (12) | −0.0041 (11) |
O2 | 0.0305 (18) | 0.0278 (16) | 0.0269 (15) | −0.0018 (13) | 0.0054 (13) | −0.0080 (12) |
O3 | 0.0236 (17) | 0.0276 (15) | 0.0255 (15) | −0.0046 (12) | 0.0010 (12) | −0.0055 (12) |
O4 | 0.0292 (18) | 0.0350 (18) | 0.0371 (17) | −0.0052 (14) | −0.0043 (14) | −0.0122 (14) |
O5 | 0.0221 (16) | 0.0311 (16) | 0.0232 (14) | −0.0008 (12) | −0.0021 (12) | 0.0046 (12) |
O6 | 0.0244 (17) | 0.0322 (16) | 0.0194 (13) | −0.0023 (13) | −0.0043 (12) | 0.0034 (12) |
O7 | 0.0220 (16) | 0.0285 (15) | 0.0236 (14) | −0.0044 (12) | −0.0008 (12) | 0.0033 (12) |
O8 | 0.0218 (17) | 0.0314 (16) | 0.0302 (16) | −0.0070 (13) | −0.0098 (13) | 0.0030 (12) |
O9 | 0.0243 (16) | 0.0228 (14) | 0.0208 (13) | 0.0005 (12) | 0.0024 (11) | 0.0005 (11) |
O10 | 0.041 (2) | 0.0375 (18) | 0.0235 (15) | 0.0053 (15) | 0.0093 (14) | −0.0005 (13) |
O11 | 0.0292 (17) | 0.0220 (13) | 0.0165 (12) | 0.0034 (12) | 0.0019 (12) | 0.0027 (10) |
O12 | 0.0363 (19) | 0.0363 (17) | 0.0210 (14) | 0.0071 (14) | 0.0043 (13) | 0.0049 (12) |
N1 | 0.0182 (17) | 0.0221 (17) | 0.0172 (16) | −0.0016 (13) | 0.0010 (13) | 0.0023 (12) |
N2 | 0.0229 (19) | 0.0193 (16) | 0.0190 (16) | 0.0003 (14) | 0.0037 (13) | −0.0004 (13) |
N3 | 0.0177 (19) | 0.0246 (17) | 0.0234 (16) | −0.0015 (14) | 0.0012 (13) | 0.0005 (13) |
C1 | 0.022 (2) | 0.020 (2) | 0.0180 (18) | 0.0011 (16) | −0.0002 (15) | 0.0031 (14) |
C2 | 0.022 (2) | 0.026 (2) | 0.023 (2) | 0.0031 (17) | 0.0030 (17) | −0.0037 (16) |
C3 | 0.018 (2) | 0.034 (2) | 0.027 (2) | −0.0014 (17) | 0.0026 (16) | 0.0030 (17) |
C4 | 0.021 (2) | 0.0224 (19) | 0.030 (2) | −0.0042 (18) | −0.0023 (18) | −0.0016 (16) |
C5 | 0.020 (2) | 0.0192 (19) | 0.026 (2) | −0.0008 (15) | −0.0029 (16) | 0.0004 (15) |
C6 | 0.022 (2) | 0.021 (2) | 0.0210 (19) | 0.0015 (16) | −0.0008 (17) | 0.0010 (15) |
C7 | 0.020 (2) | 0.019 (2) | 0.021 (2) | −0.0036 (16) | −0.0012 (16) | 0.0029 (15) |
C8 | 0.024 (2) | 0.023 (2) | 0.023 (2) | 0.0029 (17) | 0.0007 (16) | 0.0018 (16) |
C9 | 0.031 (3) | 0.027 (2) | 0.028 (2) | −0.0019 (19) | −0.0027 (18) | 0.0078 (17) |
C10 | 0.036 (3) | 0.026 (2) | 0.034 (2) | −0.008 (2) | −0.006 (2) | 0.0092 (18) |
C11 | 0.020 (2) | 0.028 (2) | 0.032 (2) | −0.0055 (18) | −0.0033 (18) | −0.0006 (18) |
C12 | 0.021 (2) | 0.020 (2) | 0.0249 (19) | −0.0010 (16) | 0.0033 (16) | −0.0036 (15) |
C13 | 0.022 (2) | 0.021 (2) | 0.024 (2) | 0.0035 (16) | 0.0037 (16) | 0.0014 (16) |
C14 | 0.016 (2) | 0.025 (2) | 0.0203 (19) | −0.0005 (16) | −0.0002 (16) | −0.0015 (15) |
C15 | 0.020 (2) | 0.023 (2) | 0.0218 (19) | −0.0023 (16) | −0.0010 (16) | 0.0018 (15) |
C16 | 0.029 (3) | 0.029 (2) | 0.023 (2) | −0.0055 (18) | −0.0011 (18) | 0.0037 (17) |
C17 | 0.023 (2) | 0.029 (2) | 0.033 (2) | 0.0031 (18) | 0.0003 (18) | −0.0004 (18) |
C18 | 0.019 (2) | 0.026 (2) | 0.032 (2) | −0.0003 (17) | 0.0014 (17) | −0.0046 (17) |
C19 | 0.020 (2) | 0.022 (2) | 0.0170 (18) | −0.0005 (16) | 0.0006 (16) | −0.0008 (15) |
C20 | 0.016 (2) | 0.025 (2) | 0.0231 (19) | −0.0038 (17) | −0.0024 (16) | 0.0043 (16) |
C21 | 0.019 (2) | 0.027 (2) | 0.0203 (19) | −0.0051 (17) | 0.0035 (16) | −0.0030 (16) |
N7 | 0.039 (2) | 0.0256 (19) | 0.0200 (17) | 0.0089 (16) | 0.0015 (15) | −0.0008 (14) |
N8 | 0.046 (3) | 0.0195 (17) | 0.0168 (16) | 0.0037 (15) | 0.0044 (15) | −0.0001 (13) |
N9 | 0.032 (2) | 0.0270 (19) | 0.0219 (17) | 0.0058 (16) | 0.0038 (15) | 0.0016 (14) |
C23 | 0.026 (2) | 0.021 (2) | 0.025 (2) | −0.0011 (17) | −0.0047 (17) | −0.0009 (16) |
O2W | 0.033 (2) | 0.049 (2) | 0.0451 (19) | −0.0004 (16) | −0.0010 (15) | −0.0155 (16) |
O3W | 0.0190 (17) | 0.0392 (18) | 0.0322 (16) | −0.0004 (13) | 0.0026 (13) | −0.0038 (13) |
O1W | 0.043 (2) | 0.0356 (18) | 0.0239 (14) | −0.0017 (14) | −0.0015 (14) | 0.0013 (13) |
N4 | 0.026 (2) | 0.054 (3) | 0.0242 (18) | 0.0114 (18) | 0.0002 (15) | 0.0060 (17) |
N5 | 0.025 (2) | 0.054 (2) | 0.0239 (18) | 0.0099 (18) | −0.0015 (15) | 0.0050 (17) |
N6 | 0.031 (2) | 0.038 (2) | 0.0208 (17) | 0.0095 (17) | 0.0002 (16) | −0.0018 (15) |
C22 | 0.023 (2) | 0.025 (2) | 0.027 (2) | −0.0002 (18) | −0.0001 (17) | 0.0064 (17) |
N10 | 0.040 (3) | 0.045 (3) | 0.041 (2) | 0.011 (2) | −0.0155 (19) | −0.0200 (19) |
N11 | 0.044 (3) | 0.044 (2) | 0.032 (2) | 0.011 (2) | −0.0136 (18) | −0.0059 (17) |
N12 | 0.031 (2) | 0.033 (2) | 0.0288 (19) | 0.0029 (16) | −0.0098 (16) | −0.0065 (15) |
C24 | 0.031 (3) | 0.042 (3) | 0.020 (2) | 0.002 (2) | 0.0033 (18) | −0.0033 (18) |
Geometric parameters (Å, º) top
Ce1—O5 | 2.500 (3) | C12—C14 | 1.528 (5) |
Ce1—O3 | 2.505 (3) | C15—C16 | 1.389 (5) |
Ce1—O11 | 2.506 (2) | C15—C20 | 1.521 (5) |
Ce1—O9 | 2.521 (3) | C16—C17 | 1.393 (6) |
Ce1—O7 | 2.533 (3) | C16—H16A | 0.9300 |
Ce1—O1 | 2.554 (3) | C17—C18 | 1.389 (6) |
Ce1—N3 | 2.617 (3) | C17—H17A | 0.9300 |
Ce1—N2 | 2.620 (3) | C18—C19 | 1.376 (5) |
Ce1—N1 | 2.626 (3) | C18—H18A | 0.9300 |
O1—C6 | 1.283 (5) | C19—C21 | 1.534 (5) |
O2—C6 | 1.237 (4) | N7—C23 | 1.327 (5) |
O3—C7 | 1.266 (5) | N7—H7A | 0.8600 |
O4—C7 | 1.238 (4) | N7—H7B | 0.8600 |
O5—C13 | 1.276 (4) | N8—C23 | 1.309 (5) |
O6—C13 | 1.244 (4) | N8—H8A | 0.8600 |
O7—C14 | 1.272 (4) | N8—H8B | 0.8600 |
O8—C14 | 1.238 (4) | N9—C23 | 1.329 (5) |
O9—C21 | 1.274 (4) | N9—H9B | 0.8600 |
O10—C21 | 1.225 (4) | N9—H9C | 0.8600 |
O11—C20 | 1.274 (4) | O2W—H2WA | 0.8601 |
O12—C20 | 1.229 (4) | O2W—H2WB | 0.8601 |
N1—C1 | 1.342 (5) | O3W—H3WB | 0.8600 |
N1—C5 | 1.346 (5) | O3W—H3WA | 0.8600 |
N2—C12 | 1.334 (5) | O1W—H1WA | 0.8600 |
N2—C8 | 1.343 (5) | O1W—H1WB | 0.8600 |
N3—C15 | 1.328 (5) | N4—C22 | 1.333 (5) |
N3—C19 | 1.344 (5) | N4—H4B | 0.8600 |
C1—C2 | 1.380 (5) | N4—H4C | 0.8600 |
C1—C6 | 1.503 (5) | N5—C22 | 1.308 (5) |
C2—C3 | 1.390 (6) | N5—H5A | 0.8600 |
C2—H2A | 0.9300 | N5—H5B | 0.8600 |
C3—C4 | 1.384 (6) | N6—C22 | 1.319 (5) |
C3—H3A | 0.9300 | N6—H6A | 0.8600 |
C4—C5 | 1.371 (5) | N6—H6B | 0.8600 |
C4—H4A | 0.9300 | N10—C24 | 1.314 (5) |
C5—C7 | 1.515 (5) | N10—H10B | 0.8600 |
C8—C9 | 1.378 (5) | N10—H10C | 0.8600 |
C8—C13 | 1.521 (6) | N11—C24 | 1.332 (6) |
C9—C10 | 1.387 (6) | N11—H11B | 0.8600 |
C9—H9A | 0.9300 | N11—H11C | 0.8600 |
C10—C11 | 1.378 (6) | N12—C24 | 1.326 (5) |
C10—H10A | 0.9300 | N12—H12A | 0.8600 |
C11—C12 | 1.400 (5) | N12—H12B | 0.8600 |
C11—H11A | 0.9300 | | |
| | | |
O5—Ce1—O3 | 75.33 (9) | C10—C9—H9A | 120.6 |
O5—Ce1—O11 | 152.63 (9) | C11—C10—C9 | 119.7 (4) |
O3—Ce1—O11 | 90.55 (9) | C11—C10—H10A | 120.2 |
O5—Ce1—O9 | 77.41 (9) | C9—C10—H10A | 120.2 |
O3—Ce1—O9 | 79.51 (9) | C10—C11—C12 | 117.7 (4) |
O11—Ce1—O9 | 123.61 (8) | C10—C11—H11A | 121.1 |
O5—Ce1—O7 | 123.58 (9) | C12—C11—H11A | 121.1 |
O3—Ce1—O7 | 156.32 (9) | N2—C12—C11 | 122.8 (4) |
O11—Ce1—O7 | 77.18 (9) | N2—C12—C14 | 114.9 (3) |
O9—Ce1—O7 | 90.41 (9) | C11—C12—C14 | 122.3 (4) |
O5—Ce1—O1 | 93.44 (9) | O6—C13—O5 | 124.9 (4) |
O3—Ce1—O1 | 123.30 (9) | O6—C13—C8 | 119.1 (3) |
O11—Ce1—O1 | 74.63 (8) | O5—C13—C8 | 116.0 (3) |
O9—Ce1—O1 | 152.85 (9) | O8—C14—O7 | 126.2 (4) |
O7—Ce1—O1 | 73.28 (9) | O8—C14—C12 | 118.0 (3) |
O5—Ce1—N3 | 135.35 (9) | O7—C14—C12 | 115.7 (3) |
O3—Ce1—N3 | 79.99 (10) | N3—C15—C16 | 122.7 (4) |
O11—Ce1—N3 | 61.85 (9) | N3—C15—C20 | 115.2 (3) |
O9—Ce1—N3 | 61.76 (9) | C16—C15—C20 | 122.1 (3) |
O7—Ce1—N3 | 76.38 (9) | C15—C16—C17 | 118.2 (4) |
O1—Ce1—N3 | 131.18 (9) | C15—C16—H16A | 120.9 |
O5—Ce1—N2 | 61.95 (9) | C17—C16—H16A | 120.9 |
O3—Ce1—N2 | 133.97 (9) | C18—C17—C16 | 119.2 (4) |
O11—Ce1—N2 | 135.45 (9) | C18—C17—H17A | 120.4 |
O9—Ce1—N2 | 75.42 (9) | C16—C17—H17A | 120.4 |
O7—Ce1—N2 | 61.66 (9) | C19—C18—C17 | 118.4 (4) |
O1—Ce1—N2 | 77.73 (9) | C19—C18—H18A | 120.8 |
N3—Ce1—N2 | 118.76 (10) | C17—C18—H18A | 120.8 |
O5—Ce1—N1 | 77.28 (9) | N3—C19—C18 | 122.8 (4) |
O3—Ce1—N1 | 61.52 (9) | N3—C19—C21 | 115.0 (3) |
O11—Ce1—N1 | 75.38 (9) | C18—C19—C21 | 122.1 (3) |
O9—Ce1—N1 | 137.66 (9) | O12—C20—O11 | 126.2 (4) |
O7—Ce1—N1 | 131.92 (9) | O12—C20—C15 | 118.5 (4) |
O1—Ce1—N1 | 61.79 (9) | O11—C20—C15 | 115.3 (3) |
N3—Ce1—N1 | 121.41 (10) | O10—C21—O9 | 127.8 (4) |
N2—Ce1—N1 | 119.78 (10) | O10—C21—C19 | 117.3 (4) |
C6—O1—Ce1 | 124.4 (2) | O9—C21—C19 | 114.8 (3) |
C7—O3—Ce1 | 127.0 (2) | C23—N7—H7A | 120.0 |
C13—O5—Ce1 | 124.8 (3) | C23—N7—H7B | 120.0 |
C14—O7—Ce1 | 126.4 (2) | H7A—N7—H7B | 120.0 |
C21—O9—Ce1 | 127.4 (2) | C23—N8—H8A | 120.0 |
C20—O11—Ce1 | 126.2 (2) | C23—N8—H8B | 120.0 |
C1—N1—C5 | 119.0 (3) | H8A—N8—H8B | 120.0 |
C1—N1—Ce1 | 120.6 (2) | C23—N9—H9B | 120.0 |
C5—N1—Ce1 | 120.4 (2) | C23—N9—H9C | 120.0 |
C12—N2—C8 | 118.4 (3) | H9B—N9—H9C | 120.0 |
C12—N2—Ce1 | 121.1 (2) | N8—C23—N7 | 119.7 (4) |
C8—N2—Ce1 | 120.4 (3) | N8—C23—N9 | 120.6 (4) |
C15—N3—C19 | 118.7 (3) | N7—C23—N9 | 119.6 (4) |
C15—N3—Ce1 | 120.4 (3) | H2WA—O2W—H2WB | 102.8 |
C19—N3—Ce1 | 120.9 (2) | H3WB—O3W—H3WA | 117.4 |
N1—C1—C2 | 122.2 (4) | H1WA—O1W—H1WB | 110.6 |
N1—C1—C6 | 115.5 (3) | C22—N4—H4B | 120.0 |
C2—C1—C6 | 122.2 (3) | C22—N4—H4C | 120.0 |
C1—C2—C3 | 118.4 (4) | H4B—N4—H4C | 120.0 |
C1—C2—H2A | 120.8 | C22—N5—H5A | 120.0 |
C3—C2—H2A | 120.8 | C22—N5—H5B | 120.0 |
C4—C3—C2 | 119.2 (4) | H5A—N5—H5B | 120.0 |
C4—C3—H3A | 120.4 | C22—N6—H6A | 120.0 |
C2—C3—H3A | 120.4 | C22—N6—H6B | 120.0 |
C5—C4—C3 | 119.1 (4) | H6A—N6—H6B | 120.0 |
C5—C4—H4A | 120.4 | N5—C22—N6 | 121.0 (4) |
C3—C4—H4A | 120.4 | N5—C22—N4 | 120.5 (4) |
N1—C5—C4 | 122.0 (4) | N6—C22—N4 | 118.5 (4) |
N1—C5—C7 | 114.5 (3) | C24—N10—H10B | 120.0 |
C4—C5—C7 | 123.4 (3) | C24—N10—H10C | 120.0 |
O2—C6—O1 | 125.4 (4) | H10B—N10—H10C | 120.0 |
O2—C6—C1 | 117.9 (4) | C24—N11—H11B | 120.0 |
O1—C6—C1 | 116.7 (3) | C24—N11—H11C | 120.0 |
O4—C7—O3 | 126.5 (4) | H11B—N11—H11C | 120.0 |
O4—C7—C5 | 118.0 (4) | C24—N12—H12A | 120.0 |
O3—C7—C5 | 115.5 (3) | C24—N12—H12B | 120.0 |
N2—C8—C9 | 122.4 (4) | H12A—N12—H12B | 120.0 |
N2—C8—C13 | 113.7 (3) | N10—C24—N12 | 120.2 (4) |
C9—C8—C13 | 123.9 (4) | N10—C24—N11 | 119.6 (4) |
C8—C9—C10 | 118.8 (4) | N12—C24—N11 | 120.2 (4) |
C8—C9—H9A | 120.6 | | |
| | | |
O5—Ce1—O1—C6 | −82.7 (3) | N1—Ce1—N3—C15 | 53.9 (3) |
O3—Ce1—O1—C6 | −8.0 (3) | O5—Ce1—N3—C19 | −23.9 (3) |
O11—Ce1—O1—C6 | 72.3 (3) | O3—Ce1—N3—C19 | −80.9 (3) |
O9—Ce1—O1—C6 | −151.5 (3) | O11—Ce1—N3—C19 | −177.0 (3) |
O7—Ce1—O1—C6 | 153.2 (3) | O9—Ce1—N3—C19 | 2.5 (3) |
N3—Ce1—O1—C6 | 99.3 (3) | O7—Ce1—N3—C19 | 100.5 (3) |
N2—Ce1—O1—C6 | −143.1 (3) | O1—Ce1—N3—C19 | 153.2 (3) |
N1—Ce1—O1—C6 | −9.1 (3) | N2—Ce1—N3—C19 | 54.1 (3) |
O5—Ce1—O3—C7 | 74.1 (3) | N1—Ce1—N3—C19 | −128.4 (3) |
O11—Ce1—O3—C7 | −82.1 (3) | C5—N1—C1—C2 | −1.1 (5) |
O9—Ce1—O3—C7 | 153.7 (3) | Ce1—N1—C1—C2 | 176.3 (3) |
O7—Ce1—O3—C7 | −140.1 (3) | C5—N1—C1—C6 | −178.8 (3) |
O1—Ce1—O3—C7 | −10.3 (3) | Ce1—N1—C1—C6 | −1.3 (4) |
N3—Ce1—O3—C7 | −143.4 (3) | N1—C1—C2—C3 | 0.7 (6) |
N2—Ce1—O3—C7 | 96.0 (3) | C6—C1—C2—C3 | 178.2 (3) |
N1—Ce1—O3—C7 | −9.1 (3) | C1—C2—C3—C4 | 0.8 (6) |
O3—Ce1—O5—C13 | 146.8 (3) | C2—C3—C4—C5 | −1.7 (6) |
O11—Ce1—O5—C13 | −152.1 (3) | C1—N1—C5—C4 | 0.1 (5) |
O9—Ce1—O5—C13 | 64.5 (3) | Ce1—N1—C5—C4 | −177.4 (3) |
O7—Ce1—O5—C13 | −17.5 (3) | C1—N1—C5—C7 | 178.6 (3) |
O1—Ce1—O5—C13 | −89.6 (3) | Ce1—N1—C5—C7 | 1.1 (4) |
N3—Ce1—O5—C13 | 88.2 (3) | C3—C4—C5—N1 | 1.3 (6) |
N2—Ce1—O5—C13 | −15.5 (3) | C3—C4—C5—C7 | −177.0 (4) |
N1—Ce1—O5—C13 | −149.7 (3) | Ce1—O1—C6—O2 | −165.4 (3) |
O5—Ce1—O7—C14 | −1.8 (3) | Ce1—O1—C6—C1 | 12.2 (4) |
O3—Ce1—O7—C14 | −141.0 (3) | N1—C1—C6—O2 | 171.1 (3) |
O11—Ce1—O7—C14 | 158.6 (3) | C2—C1—C6—O2 | −6.5 (6) |
O9—Ce1—O7—C14 | −76.9 (3) | N1—C1—C6—O1 | −6.7 (5) |
O1—Ce1—O7—C14 | 81.0 (3) | C2—C1—C6—O1 | 175.7 (4) |
N3—Ce1—O7—C14 | −137.7 (3) | Ce1—O3—C7—O4 | −167.2 (3) |
N2—Ce1—O7—C14 | −3.8 (3) | Ce1—O3—C7—C5 | 13.1 (4) |
N1—Ce1—O7—C14 | 102.1 (3) | N1—C5—C7—O4 | 171.8 (3) |
O5—Ce1—O9—C21 | 158.6 (3) | C4—C5—C7—O4 | −9.7 (6) |
O3—Ce1—O9—C21 | 81.5 (3) | N1—C5—C7—O3 | −8.4 (5) |
O11—Ce1—O9—C21 | −2.1 (3) | C4—C5—C7—O3 | 170.0 (4) |
O7—Ce1—O9—C21 | −77.0 (3) | C12—N2—C8—C9 | 0.2 (6) |
O1—Ce1—O9—C21 | −128.9 (3) | Ce1—N2—C8—C9 | −179.6 (3) |
N3—Ce1—O9—C21 | −2.7 (3) | C12—N2—C8—C13 | −179.6 (3) |
N2—Ce1—O9—C21 | −137.5 (3) | Ce1—N2—C8—C13 | 0.6 (4) |
N1—Ce1—O9—C21 | 104.1 (3) | N2—C8—C9—C10 | 3.1 (6) |
O5—Ce1—O11—C20 | −146.0 (3) | C13—C8—C9—C10 | −177.1 (4) |
O3—Ce1—O11—C20 | −88.2 (3) | C8—C9—C10—C11 | −3.3 (7) |
O9—Ce1—O11—C20 | −10.4 (3) | C9—C10—C11—C12 | 0.3 (6) |
O7—Ce1—O11—C20 | 71.4 (3) | C8—N2—C12—C11 | −3.3 (6) |
O1—Ce1—O11—C20 | 147.3 (3) | Ce1—N2—C12—C11 | 176.5 (3) |
N3—Ce1—O11—C20 | −9.8 (3) | C8—N2—C12—C14 | 174.7 (3) |
N2—Ce1—O11—C20 | 93.7 (3) | Ce1—N2—C12—C14 | −5.5 (4) |
N1—Ce1—O11—C20 | −148.5 (3) | C10—C11—C12—N2 | 3.1 (6) |
O5—Ce1—N1—C1 | 105.7 (3) | C10—C11—C12—C14 | −174.9 (4) |
O3—Ce1—N1—C1 | −174.2 (3) | Ce1—O5—C13—O6 | −159.1 (3) |
O11—Ce1—N1—C1 | −75.4 (3) | Ce1—O5—C13—C8 | 21.9 (5) |
O9—Ce1—N1—C1 | 160.3 (2) | N2—C8—C13—O6 | 167.3 (3) |
O7—Ce1—N1—C1 | −18.3 (3) | C9—C8—C13—O6 | −12.5 (6) |
O1—Ce1—N1—C1 | 4.7 (2) | N2—C8—C13—O5 | −13.6 (5) |
N3—Ce1—N1—C1 | −118.5 (3) | C9—C8—C13—O5 | 166.6 (4) |
N2—Ce1—N1—C1 | 58.9 (3) | Ce1—O7—C14—O8 | 179.2 (3) |
O5—Ce1—N1—C5 | −76.8 (3) | Ce1—O7—C14—C12 | 2.6 (5) |
O3—Ce1—N1—C5 | 3.2 (2) | N2—C12—C14—O8 | −174.9 (3) |
O11—Ce1—N1—C5 | 102.0 (3) | C11—C12—C14—O8 | 3.2 (6) |
O9—Ce1—N1—C5 | −22.2 (3) | N2—C12—C14—O7 | 2.1 (5) |
O7—Ce1—N1—C5 | 159.2 (2) | C11—C12—C14—O7 | −179.9 (4) |
O1—Ce1—N1—C5 | −177.8 (3) | C19—N3—C15—C16 | 0.0 (6) |
N3—Ce1—N1—C5 | 59.0 (3) | Ce1—N3—C15—C16 | 177.7 (3) |
N2—Ce1—N1—C5 | −123.6 (3) | C19—N3—C15—C20 | −179.8 (3) |
O5—Ce1—N2—C12 | −173.4 (3) | Ce1—N3—C15—C20 | −2.1 (4) |
O3—Ce1—N2—C12 | 162.5 (3) | N3—C15—C16—C17 | 1.3 (6) |
O11—Ce1—N2—C12 | −20.1 (3) | C20—C15—C16—C17 | −178.9 (4) |
O9—Ce1—N2—C12 | 103.3 (3) | C15—C16—C17—C18 | −1.4 (6) |
O7—Ce1—N2—C12 | 4.8 (3) | C16—C17—C18—C19 | 0.2 (6) |
O1—Ce1—N2—C12 | −72.7 (3) | C15—N3—C19—C18 | −1.3 (6) |
N3—Ce1—N2—C12 | 57.8 (3) | Ce1—N3—C19—C18 | −179.0 (3) |
N1—Ce1—N2—C12 | −119.7 (3) | C15—N3—C19—C21 | 175.3 (3) |
O5—Ce1—N2—C8 | 6.4 (3) | Ce1—N3—C19—C21 | −2.4 (4) |
O3—Ce1—N2—C8 | −17.7 (3) | C17—C18—C19—N3 | 1.2 (6) |
O11—Ce1—N2—C8 | 159.7 (2) | C17—C18—C19—C21 | −175.1 (4) |
O9—Ce1—N2—C8 | −76.9 (3) | Ce1—O11—C20—O12 | −167.3 (3) |
O7—Ce1—N2—C8 | −175.5 (3) | Ce1—O11—C20—C15 | 12.5 (5) |
O1—Ce1—N2—C8 | 107.1 (3) | N3—C15—C20—O12 | 173.7 (4) |
N3—Ce1—N2—C8 | −122.4 (3) | C16—C15—C20—O12 | −6.1 (6) |
N1—Ce1—N2—C8 | 60.1 (3) | N3—C15—C20—O11 | −6.0 (5) |
O5—Ce1—N3—C15 | 158.5 (3) | C16—C15—C20—O11 | 174.2 (4) |
O3—Ce1—N3—C15 | 101.5 (3) | Ce1—O9—C21—O10 | −178.8 (3) |
O11—Ce1—N3—C15 | 5.4 (3) | Ce1—O9—C21—C19 | 2.6 (5) |
O9—Ce1—N3—C15 | −175.1 (3) | N3—C19—C21—O10 | −178.7 (4) |
O7—Ce1—N3—C15 | −77.2 (3) | C18—C19—C21—O10 | −2.1 (6) |
O1—Ce1—N3—C15 | −24.4 (3) | N3—C19—C21—O9 | 0.1 (5) |
N2—Ce1—N3—C15 | −123.5 (3) | C18—C19—C21—O9 | 176.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2W—H2WA···O1W | 0.86 | 1.93 | 2.777 (4) | 169 |
O2W—H2WB···O3W | 0.86 | 1.97 | 2.744 (4) | 149 |
O3W—H3WB···O8i | 0.86 | 1.93 | 2.761 (4) | 163 |
O3W—H3WA···O5 | 0.86 | 1.91 | 2.771 (4) | 176 |
N4—H4C···O11ii | 0.86 | 2.08 | 2.896 (4) | 157 |
O1W—H1WA···O9iii | 0.86 | 2.04 | 2.893 (4) | 171 |
N5—H5A···O7 | 0.86 | 2.04 | 2.884 (4) | 167 |
N5—H5B···O2Wiv | 0.86 | 2.17 | 3.028 (5) | 174 |
O1W—H1WB···O6 | 0.86 | 2.13 | 2.940 (4) | 157 |
N6—H6A···O1 | 0.86 | 2.31 | 3.117 (4) | 155 |
N6—H6B···O12ii | 0.86 | 2.01 | 2.854 (4) | 168 |
N7—H7A···O1W | 0.86 | 2.40 | 3.083 (4) | 137 |
N7—H7A···O6iii | 0.86 | 2.54 | 3.202 (4) | 135 |
N7—H7B···O3 | 0.86 | 2.30 | 2.997 (4) | 139 |
N8—H8A···O6iii | 0.86 | 2.05 | 2.835 (4) | 151 |
N8—H8B···O2v | 0.86 | 2.08 | 2.858 (4) | 150 |
N9—H9B···O1v | 0.86 | 2.22 | 3.077 (4) | 179 |
N9—H9C···O3 | 0.86 | 2.12 | 2.861 (4) | 145 |
N10—H10B···O2Wvi | 0.86 | 2.01 | 2.872 (5) | 176 |
N10—H10C···O2vii | 0.86 | 2.26 | 2.989 (5) | 143 |
N11—H11B···O10viii | 0.86 | 2.00 | 2.849 (5) | 170 |
N11—H11C···O3Wiv | 0.86 | 2.15 | 2.951 (4) | 155 |
N12—H12A···O4vi | 0.86 | 2.31 | 2.985 (4) | 136 |
N12—H12B···O8 | 0.86 | 2.09 | 2.925 (4) | 164 |
C3—H3A···O9i | 0.93 | 2.49 | 3.296 (4) | 145 |
C17—H17A···O8ix | 0.93 | 2.56 | 3.390 (5) | 148 |
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x−1/2, y, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x−1/2, −y+1/2, −z+1; (viii) −x+1/2, −y+1, z−1/2; (ix) −x+1/2, y+1/2, z. |