Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028061/hk2271sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028061/hk2271Isup2.hkl |
CCDC reference: 1148884
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.010 Å
- R factor = 0.037
- wR factor = 0.096
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O9 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C15 -C20 1.37 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 74.00 A 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ce1 (3) 2.48 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Cerium (III) chloride hexahydrate (106.1 mg, 0.3 mmol), phen (59.4 mg, 0.3 mmol), phenoxyacetic acid (91.3 mg, 0.6 mmol) and distilled water (3 g) were placed into the bomb and sealed. Then, the bomb was heated under autogenous pressure up to 423 K over the course of 7 d, and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals, which were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.
H atoms were positioned geometrically, with C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Daiguebonne et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The two N atoms of 1,10-phenanthroline (phen) ligand and four O atoms of three phenoxyacetic acid ligands are coordinated to the Ce atom. The Ce—O and Ce—N bonds are in the range of [2.434 (3)–2.855 (3) Å] and [2.723 (3)–2.730 (3) Å], respectively, (Table 1).
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) lead to a supramolecular network structure (Fig. 2), in which they may be effective in the stabilization of the structure.
For general background, see: Allen et al. (1987); Daiguebonne et al. (2000); Farrugia et al. (2000); Tsukube & Shinoda (2002); Zhang et al. (2005). For related literature, see: Starynowicz (1991, 1993); Kay et al. (1972); Ma et al. (1999); Zeng et al. (2000); Mao et al. (1998).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.
[Ce(C8H7O3)3(C12H8N2)] | F(000) = 1556 |
Mr = 773.73 | Dx = 1.496 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9077 reflections |
a = 20.025 (3) Å | θ = 2.5–27.0° |
b = 8.621 (3) Å | µ = 1.38 mm−1 |
c = 20.7996 (18) Å | T = 273 K |
β = 106.982 (5)° | Plane, colorless |
V = 3434.4 (13) Å3 | 0.33 × 0.12 × 0.08 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 6830 independent reflections |
Radiation source: fine-focus sealed tube | 4757 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 26.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→24 |
Tmin = 0.661, Tmax = 0.896 | k = −10→10 |
25231 measured reflections | l = −25→25 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.9312P] where P = (Fo2 + 2Fc2)/3 |
6830 reflections | (Δ/σ)max = 0.001 |
403 parameters | Δρmax = 1.05 e Å−3 |
3 restraints | Δρmin = −0.64 e Å−3 |
[Ce(C8H7O3)3(C12H8N2)] | V = 3434.4 (13) Å3 |
Mr = 773.73 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 20.025 (3) Å | µ = 1.38 mm−1 |
b = 8.621 (3) Å | T = 273 K |
c = 20.7996 (18) Å | 0.33 × 0.12 × 0.08 mm |
β = 106.982 (5)° |
Bruker SMART CCD area-detector diffractometer | 6830 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4757 reflections with I > 2σ(I) |
Tmin = 0.661, Tmax = 0.896 | Rint = 0.041 |
25231 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 3 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.01 | Δρmax = 1.05 e Å−3 |
6830 reflections | Δρmin = −0.64 e Å−3 |
403 parameters |
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 | 0.931203 (11) | 0.19065 (2) | 0.964289 (10) | 0.03957 (9) | |
O1 | 0.97059 (14) | 0.0603 (3) | 0.87482 (12) | 0.0514 (7) | |
O2 | 1.06696 (14) | −0.0829 (3) | 0.92162 (13) | 0.0542 (7) | |
O3 | 1.11835 (16) | −0.0165 (4) | 0.82198 (15) | 0.0722 (9) | |
O4 | 0.94003 (14) | 0.4207 (3) | 1.03410 (13) | 0.0517 (7) | |
O5 | 1.00789 (16) | 0.6128 (4) | 1.09098 (13) | 0.0615 (8) | |
O6 | 0.98699 (16) | 0.5277 (4) | 1.20628 (14) | 0.0664 (9) | |
O7 | 0.84635 (13) | −0.0360 (3) | 0.91881 (13) | 0.0484 (7) | |
O8 | 0.94656 (13) | −0.1381 (4) | 0.97709 (13) | 0.0539 (7) | |
O9 | 0.78450 (16) | −0.3263 (3) | 0.89803 (17) | 0.0674 (9) | |
N1 | 0.79695 (18) | 0.2345 (4) | 0.96673 (17) | 0.0517 (8) | |
N2 | 0.83406 (19) | 0.3068 (4) | 0.85441 (16) | 0.0518 (8) | |
C1 | 0.7781 (2) | 0.1921 (6) | 1.0201 (2) | 0.0673 (13) | |
H1 | 0.8127 | 0.1692 | 1.0597 | 0.081* | |
C2 | 0.7093 (3) | 0.1807 (7) | 1.0190 (3) | 0.0878 (18) | |
H2 | 0.6978 | 0.1512 | 1.0575 | 0.105* | |
C3 | 0.6582 (3) | 0.2128 (8) | 0.9614 (4) | 0.098 (2) | |
H3 | 0.6117 | 0.2038 | 0.9604 | 0.118* | |
C4 | 0.6745 (3) | 0.2587 (7) | 0.9042 (3) | 0.0791 (16) | |
C5 | 0.7460 (2) | 0.2674 (5) | 0.9088 (2) | 0.0559 (11) | |
C6 | 0.6231 (3) | 0.2973 (9) | 0.8401 (4) | 0.114 (3) | |
H6 | 0.5758 | 0.2884 | 0.8362 | 0.137* | |
C7 | 0.6423 (3) | 0.3445 (8) | 0.7876 (4) | 0.108 (2) | |
H7 | 0.6083 | 0.3716 | 0.7481 | 0.129* | |
C8 | 0.7134 (3) | 0.3544 (6) | 0.7903 (3) | 0.0746 (15) | |
C9 | 0.7660 (2) | 0.3100 (5) | 0.8505 (2) | 0.0554 (11) | |
C10 | 0.7356 (4) | 0.4032 (7) | 0.7366 (3) | 0.0911 (19) | |
H10 | 0.7031 | 0.4376 | 0.6974 | 0.109* | |
C11 | 0.8036 (4) | 0.4012 (6) | 0.7406 (2) | 0.0845 (17) | |
H11 | 0.8185 | 0.4336 | 0.7045 | 0.101* | |
C12 | 0.8526 (3) | 0.3490 (5) | 0.8009 (2) | 0.0673 (13) | |
H12 | 0.8995 | 0.3444 | 0.8029 | 0.081* | |
C13 | 1.0286 (2) | 0.0033 (5) | 0.87711 (19) | 0.0461 (9) | |
C14 | 1.0525 (2) | 0.0507 (6) | 0.8173 (2) | 0.0595 (11) | |
H14A | 1.0186 | 0.0170 | 0.7762 | 0.071* | |
H14B | 1.0560 | 0.1628 | 0.8160 | 0.071* | |
C15 | 1.1457 (3) | 0.0145 (6) | 0.7703 (2) | 0.0669 (13) | |
C16 | 1.2079 (3) | −0.0558 (7) | 0.7766 (3) | 0.0857 (16) | |
H16 | 1.2287 | −0.1170 | 0.8139 | 0.103* | |
C17 | 1.2400 (3) | −0.0351 (8) | 0.7265 (4) | 0.101 (2) | |
H17 | 1.2827 | −0.0825 | 0.7302 | 0.121* | |
C18 | 1.2095 (4) | 0.0542 (8) | 0.6720 (4) | 0.108 (2) | |
H18 | 1.2313 | 0.0664 | 0.6385 | 0.130* | |
C19 | 1.1485 (4) | 0.1246 (9) | 0.6661 (3) | 0.111 (2) | |
H19 | 1.1284 | 0.1861 | 0.6288 | 0.134* | |
C20 | 1.1150 (3) | 0.1063 (7) | 0.7157 (3) | 0.0886 (17) | |
H20 | 1.0726 | 0.1552 | 0.7118 | 0.106* | |
C21 | 0.9692 (2) | 0.4991 (5) | 1.0864 (2) | 0.0475 (10) | |
C22 | 0.9489 (2) | 0.4458 (6) | 1.14737 (19) | 0.0601 (12) | |
H22A | 0.8993 | 0.4625 | 1.1398 | 0.072* | |
H22B | 0.9580 | 0.3355 | 1.1540 | 0.072* | |
C23 | 0.9747 (2) | 0.4888 (5) | 1.2656 (2) | 0.0587 (11) | |
C24 | 0.9277 (3) | 0.3799 (7) | 1.2718 (2) | 0.0784 (15) | |
H24 | 0.9015 | 0.3252 | 1.2344 | 0.094* | |
C25 | 0.9196 (4) | 0.3521 (9) | 1.3346 (3) | 0.111 (2) | |
H25 | 0.8883 | 0.2765 | 1.3395 | 0.133* | |
C26 | 0.9567 (4) | 0.4338 (9) | 1.3896 (3) | 0.108 (2) | |
H26 | 0.9495 | 0.4161 | 1.4311 | 0.130* | |
C27 | 1.0044 (3) | 0.5416 (8) | 1.3836 (2) | 0.0950 (19) | |
H27 | 1.0303 | 0.5960 | 1.4212 | 0.114* | |
C28 | 1.0143 (3) | 0.5699 (6) | 1.3219 (2) | 0.0759 (14) | |
H28 | 1.0471 | 0.6426 | 1.3177 | 0.091* | |
C29 | 0.8842 (2) | −0.1510 (5) | 0.93922 (19) | 0.0477 (10) | |
C30 | 0.8575 (2) | −0.3145 (5) | 0.9190 (2) | 0.0590 (11) | |
H30A | 0.8753 | −0.3495 | 0.8829 | 0.071* | |
H30B | 0.8758 | −0.3833 | 0.9570 | 0.071* | |
C31 | 0.7518 (5) | −0.3130 (8) | 0.9450 (5) | 0.1312 (13) | |
C32 | 0.7848 (5) | −0.2768 (8) | 1.0119 (5) | 0.1312 (13) | |
H32 | 0.8328 | −0.2609 | 1.0272 | 0.157* | |
C33 | 0.7427 (5) | −0.2649 (8) | 1.0558 (5) | 0.1312 (13) | |
H33 | 0.7622 | −0.2401 | 1.1009 | 0.157* | |
C34 | 0.6743 (5) | −0.2903 (8) | 1.0306 (5) | 0.1312 (13) | |
H34 | 0.6469 | −0.2782 | 1.0595 | 0.157* | |
C35 | 0.6404 (5) | −0.3336 (8) | 0.9644 (5) | 0.1312 (13) | |
H35 | 0.5931 | −0.3583 | 0.9505 | 0.157* | |
C36 | 0.6803 (5) | −0.3377 (8) | 0.9211 (5) | 0.1312 (13) | |
H36 | 0.6595 | −0.3571 | 0.8757 | 0.157* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ce1 | 0.04539 (14) | 0.03484 (14) | 0.03388 (13) | −0.00163 (10) | 0.00435 (8) | 0.00054 (10) |
O1 | 0.0596 (17) | 0.0523 (18) | 0.0422 (15) | 0.0084 (15) | 0.0146 (13) | 0.0023 (13) |
O2 | 0.0639 (18) | 0.0546 (18) | 0.0449 (16) | 0.0080 (15) | 0.0172 (13) | 0.0113 (14) |
O3 | 0.071 (2) | 0.092 (3) | 0.062 (2) | 0.0188 (18) | 0.0316 (16) | 0.0227 (17) |
O4 | 0.0723 (18) | 0.0382 (16) | 0.0431 (15) | −0.0063 (14) | 0.0144 (13) | −0.0054 (13) |
O5 | 0.089 (2) | 0.0535 (19) | 0.0424 (16) | −0.0279 (18) | 0.0192 (15) | −0.0023 (14) |
O6 | 0.092 (2) | 0.067 (2) | 0.0412 (16) | −0.0285 (17) | 0.0206 (15) | −0.0070 (14) |
O7 | 0.0482 (15) | 0.0386 (16) | 0.0506 (16) | 0.0005 (13) | 0.0023 (12) | −0.0032 (12) |
O8 | 0.0476 (16) | 0.0585 (18) | 0.0468 (16) | −0.0039 (13) | 0.0000 (13) | 0.0076 (13) |
O9 | 0.062 (2) | 0.051 (2) | 0.076 (2) | −0.0144 (15) | −0.0017 (16) | −0.0073 (16) |
N1 | 0.051 (2) | 0.047 (2) | 0.050 (2) | 0.0040 (16) | 0.0040 (16) | −0.0077 (16) |
N2 | 0.065 (2) | 0.041 (2) | 0.0407 (19) | 0.0030 (17) | 0.0008 (16) | 0.0005 (15) |
C1 | 0.061 (3) | 0.082 (4) | 0.058 (3) | 0.008 (3) | 0.017 (2) | −0.002 (3) |
C2 | 0.060 (3) | 0.125 (5) | 0.084 (4) | 0.005 (3) | 0.029 (3) | −0.014 (4) |
C3 | 0.052 (3) | 0.119 (6) | 0.120 (6) | −0.003 (3) | 0.020 (3) | −0.018 (4) |
C4 | 0.052 (3) | 0.092 (4) | 0.078 (4) | 0.007 (3) | −0.005 (3) | −0.020 (3) |
C5 | 0.052 (3) | 0.043 (3) | 0.064 (3) | 0.006 (2) | 0.004 (2) | −0.011 (2) |
C6 | 0.062 (4) | 0.147 (7) | 0.109 (6) | 0.015 (4) | −0.013 (4) | −0.029 (5) |
C7 | 0.079 (4) | 0.119 (6) | 0.089 (5) | 0.038 (4) | −0.031 (4) | −0.018 (4) |
C8 | 0.078 (4) | 0.067 (3) | 0.056 (3) | 0.018 (3) | −0.016 (3) | −0.010 (2) |
C9 | 0.061 (3) | 0.039 (2) | 0.049 (2) | 0.005 (2) | −0.011 (2) | −0.005 (2) |
C10 | 0.117 (5) | 0.076 (4) | 0.051 (3) | 0.019 (4) | −0.021 (3) | 0.001 (3) |
C11 | 0.122 (5) | 0.076 (4) | 0.042 (3) | −0.001 (4) | 0.002 (3) | 0.011 (3) |
C12 | 0.086 (3) | 0.058 (3) | 0.049 (3) | −0.003 (3) | 0.006 (2) | 0.008 (2) |
C13 | 0.059 (3) | 0.038 (2) | 0.040 (2) | −0.005 (2) | 0.0124 (19) | −0.0020 (18) |
C14 | 0.067 (3) | 0.062 (3) | 0.052 (3) | 0.006 (2) | 0.021 (2) | 0.012 (2) |
C15 | 0.074 (3) | 0.073 (3) | 0.064 (3) | −0.006 (3) | 0.036 (3) | 0.000 (3) |
C16 | 0.083 (4) | 0.107 (5) | 0.079 (4) | 0.002 (3) | 0.041 (3) | 0.000 (3) |
C17 | 0.095 (4) | 0.108 (5) | 0.121 (5) | −0.007 (4) | 0.066 (4) | −0.010 (4) |
C18 | 0.143 (6) | 0.090 (5) | 0.126 (6) | −0.016 (5) | 0.095 (5) | −0.001 (4) |
C19 | 0.155 (6) | 0.108 (5) | 0.097 (5) | 0.014 (5) | 0.080 (5) | 0.032 (4) |
C20 | 0.105 (4) | 0.098 (4) | 0.081 (4) | 0.009 (4) | 0.055 (3) | 0.026 (3) |
C21 | 0.062 (3) | 0.038 (2) | 0.042 (2) | −0.002 (2) | 0.0134 (19) | 0.0013 (18) |
C22 | 0.078 (3) | 0.058 (3) | 0.046 (2) | −0.020 (2) | 0.020 (2) | −0.005 (2) |
C23 | 0.075 (3) | 0.060 (3) | 0.041 (2) | −0.003 (2) | 0.017 (2) | 0.003 (2) |
C24 | 0.084 (4) | 0.096 (4) | 0.058 (3) | −0.034 (3) | 0.026 (3) | −0.003 (3) |
C25 | 0.130 (5) | 0.146 (6) | 0.069 (4) | −0.061 (5) | 0.047 (4) | −0.003 (4) |
C26 | 0.133 (5) | 0.147 (6) | 0.055 (3) | −0.028 (5) | 0.042 (4) | 0.010 (4) |
C27 | 0.121 (5) | 0.114 (5) | 0.044 (3) | −0.021 (4) | 0.014 (3) | −0.010 (3) |
C28 | 0.091 (4) | 0.081 (4) | 0.053 (3) | −0.022 (3) | 0.017 (2) | −0.010 (3) |
C29 | 0.051 (2) | 0.053 (3) | 0.035 (2) | −0.004 (2) | 0.0068 (17) | −0.0030 (18) |
C30 | 0.064 (3) | 0.048 (3) | 0.058 (3) | 0.003 (2) | 0.008 (2) | −0.006 (2) |
C31 | 0.143 (3) | 0.099 (2) | 0.177 (4) | 0.016 (2) | 0.086 (3) | 0.030 (3) |
C32 | 0.143 (3) | 0.099 (2) | 0.177 (4) | 0.016 (2) | 0.086 (3) | 0.030 (3) |
C33 | 0.143 (3) | 0.099 (2) | 0.177 (4) | 0.016 (2) | 0.086 (3) | 0.030 (3) |
C34 | 0.143 (3) | 0.099 (2) | 0.177 (4) | 0.016 (2) | 0.086 (3) | 0.030 (3) |
C35 | 0.143 (3) | 0.099 (2) | 0.177 (4) | 0.016 (2) | 0.086 (3) | 0.030 (3) |
C36 | 0.143 (3) | 0.099 (2) | 0.177 (4) | 0.016 (2) | 0.086 (3) | 0.030 (3) |
Ce1—O1 | 2.491 (3) | C11—C12 | 1.422 (7) |
Ce1—O4 | 2.434 (3) | C11—H11 | 0.9300 |
Ce1—O7 | 2.581 (3) | C12—H12 | 0.9300 |
Ce1—O8 | 2.855 (3) | C13—C14 | 1.513 (5) |
Ce1—N1 | 2.730 (3) | C14—H14A | 0.9700 |
Ce1—N2 | 2.723 (3) | C14—H14B | 0.9700 |
Ce1—O8i | 2.437 (3) | C15—C16 | 1.357 (7) |
Ce1—O2i | 2.538 (3) | C15—C20 | 1.373 (7) |
Ce1—O5ii | 2.549 (3) | C16—C17 | 1.385 (7) |
O1—C13 | 1.250 (5) | C16—H16 | 0.9300 |
O2—C13 | 1.258 (4) | C17—C18 | 1.358 (9) |
O2—Ce1i | 2.538 (3) | C17—H17 | 0.9300 |
O3—C15 | 1.368 (5) | C18—C19 | 1.337 (9) |
O3—C14 | 1.417 (5) | C18—H18 | 0.9300 |
O4—C21 | 1.269 (5) | C19—C20 | 1.394 (7) |
O5—C21 | 1.236 (5) | C19—H19 | 0.9300 |
O5—Ce1ii | 2.549 (3) | C20—H20 | 0.9300 |
O6—C23 | 1.368 (5) | C21—C22 | 1.512 (5) |
O6—C22 | 1.426 (5) | C22—H22A | 0.9700 |
O7—C29 | 1.245 (5) | C22—H22B | 0.9700 |
O8—C29 | 1.271 (5) | C23—C24 | 1.362 (6) |
O8—Ce1i | 2.437 (3) | C23—C28 | 1.394 (6) |
O9—C31 | 1.331 (9) | C24—C25 | 1.384 (7) |
O9—C30 | 1.401 (5) | C24—H24 | 0.9300 |
N1—C1 | 1.323 (6) | C25—C26 | 1.362 (8) |
N1—C5 | 1.362 (5) | C25—H25 | 0.9300 |
N2—C12 | 1.322 (5) | C26—C27 | 1.365 (8) |
N2—C9 | 1.342 (6) | C26—H26 | 0.9300 |
C1—C2 | 1.376 (7) | C27—C28 | 1.376 (7) |
C1—H1 | 0.9300 | C27—H27 | 0.9300 |
C2—C3 | 1.358 (8) | C28—H28 | 0.9300 |
C2—H2 | 0.9300 | C29—C30 | 1.523 (6) |
C3—C4 | 1.381 (8) | C30—H30A | 0.9700 |
C3—H3 | 0.9300 | C30—H30B | 0.9700 |
C4—C5 | 1.408 (7) | C31—C36 | 1.388 (11) |
C4—C6 | 1.465 (8) | C31—C32 | 1.390 (12) |
C5—C9 | 1.432 (6) | C32—C33 | 1.417 (10) |
C6—C7 | 1.324 (9) | C32—H32 | 0.9300 |
C6—H6 | 0.9300 | C33—C34 | 1.334 (11) |
C7—C8 | 1.410 (9) | C33—H33 | 0.9300 |
C7—H7 | 0.9300 | C34—C35 | 1.397 (11) |
C8—C10 | 1.383 (8) | C34—H34 | 0.9300 |
C8—C9 | 1.432 (6) | C35—C36 | 1.368 (9) |
C10—C11 | 1.339 (8) | C35—H35 | 0.9300 |
C10—H10 | 0.9300 | C36—H36 | 0.9300 |
O1—Ce1—O4 | 146.07 (9) | C12—C11—H11 | 120.4 |
O1—Ce1—O7 | 72.71 (9) | N2—C12—C11 | 122.6 (5) |
O1—Ce1—O8 | 64.70 (8) | N2—C12—H12 | 118.7 |
O4—Ce1—O7 | 139.55 (9) | C11—C12—H12 | 118.7 |
O4—Ce1—O8 | 140.03 (8) | O1—C13—O2 | 128.4 (4) |
O7—Ce1—O8 | 47.47 (8) | O1—C13—C14 | 112.1 (3) |
O1—Ce1—N1 | 127.21 (10) | O2—C13—C14 | 119.5 (4) |
O4—Ce1—N1 | 77.08 (10) | O3—C14—C13 | 110.2 (3) |
O7—Ce1—N1 | 64.23 (10) | O3—C14—H14A | 109.6 |
O8—Ce1—N1 | 102.45 (9) | C13—C14—H14A | 109.6 |
O1—Ce1—N2 | 80.99 (10) | O3—C14—H14B | 109.6 |
O4—Ce1—N2 | 96.35 (9) | C13—C14—H14B | 109.6 |
O7—Ce1—N2 | 74.83 (9) | H14A—C14—H14B | 108.1 |
O8—Ce1—N2 | 118.33 (9) | C16—C15—O3 | 113.9 (5) |
N1—Ce1—N2 | 59.91 (11) | C16—C15—C20 | 121.0 (5) |
O4—Ce1—O8i | 88.03 (10) | O3—C15—C20 | 125.2 (5) |
O8i—Ce1—O1 | 78.41 (9) | C15—C16—C17 | 119.0 (6) |
O4—Ce1—O2i | 76.22 (9) | C15—C16—H16 | 120.5 |
O8i—Ce1—O2i | 74.10 (9) | C17—C16—H16 | 120.5 |
O1—Ce1—O2i | 127.72 (9) | C18—C17—C16 | 120.4 (6) |
O4—Ce1—O5ii | 76.50 (9) | C18—C17—H17 | 119.8 |
O8i—Ce1—O5ii | 78.82 (10) | C16—C17—H17 | 119.8 |
O1—Ce1—O5ii | 70.46 (9) | C19—C18—C17 | 120.6 (6) |
O2i—Ce1—O5ii | 141.86 (9) | C19—C18—H18 | 119.7 |
O8i—Ce1—O7 | 120.01 (10) | C17—C18—H18 | 119.7 |
O2i—Ce1—O7 | 83.91 (9) | C18—C19—C20 | 120.4 (6) |
O5ii—Ce1—O7 | 133.50 (9) | C18—C19—H19 | 119.8 |
O8i—Ce1—N2 | 148.78 (10) | C20—C19—H19 | 119.8 |
O2i—Ce1—N2 | 136.97 (10) | C15—C20—C19 | 118.7 (6) |
O5ii—Ce1—N2 | 72.28 (10) | C15—C20—H20 | 120.7 |
O8i—Ce1—N1 | 150.12 (10) | C19—C20—H20 | 120.7 |
O2i—Ce1—N1 | 77.22 (10) | O5—C21—O4 | 127.6 (4) |
O5ii—Ce1—N1 | 121.32 (11) | O5—C21—C22 | 119.5 (4) |
O8i—Ce1—O8 | 72.77 (10) | O4—C21—C22 | 112.8 (4) |
O2i—Ce1—O8 | 65.03 (9) | O6—C22—C21 | 111.3 (3) |
O5ii—Ce1—O8 | 130.48 (9) | O6—C22—H22A | 109.4 |
C13—O1—Ce1 | 130.0 (2) | C21—C22—H22A | 109.4 |
C13—O2—Ce1i | 138.0 (3) | O6—C22—H22B | 109.4 |
C15—O3—C14 | 116.4 (3) | C21—C22—H22B | 109.4 |
C21—O4—Ce1 | 151.7 (3) | H22A—C22—H22B | 108.0 |
C21—O5—Ce1ii | 149.8 (3) | C24—C23—O6 | 124.4 (4) |
C23—O6—C22 | 117.5 (3) | C24—C23—C28 | 120.3 (4) |
C29—O7—Ce1 | 102.0 (2) | O6—C23—C28 | 115.3 (4) |
C29—O8—Ce1i | 162.7 (3) | C23—C24—C25 | 118.9 (5) |
C29—O8—Ce1 | 88.2 (2) | C23—C24—H24 | 120.5 |
Ce1i—O8—Ce1 | 107.23 (10) | C25—C24—H24 | 120.5 |
C31—O9—C30 | 117.2 (6) | C26—C25—C24 | 121.1 (6) |
C1—N1—C5 | 118.4 (4) | C26—C25—H25 | 119.5 |
C1—N1—Ce1 | 120.1 (3) | C24—C25—H25 | 119.5 |
C5—N1—Ce1 | 120.0 (3) | C25—C26—C27 | 120.0 (5) |
C12—N2—C9 | 118.2 (4) | C25—C26—H26 | 120.0 |
C12—N2—Ce1 | 120.0 (3) | C27—C26—H26 | 120.0 |
C9—N2—Ce1 | 121.5 (3) | C26—C27—C28 | 120.1 (5) |
N1—C1—C2 | 122.4 (5) | C26—C27—H27 | 120.0 |
N1—C1—H1 | 118.8 | C28—C27—H27 | 120.0 |
C2—C1—H1 | 118.8 | C27—C28—C23 | 119.5 (5) |
C3—C2—C1 | 119.4 (5) | C27—C28—H28 | 120.2 |
C3—C2—H2 | 120.3 | C23—C28—H28 | 120.2 |
C1—C2—H2 | 120.3 | O7—C29—O8 | 122.1 (4) |
C2—C3—C4 | 120.9 (5) | O7—C29—C30 | 120.9 (4) |
C2—C3—H3 | 119.6 | O8—C29—C30 | 117.0 (4) |
C4—C3—H3 | 119.6 | O9—C30—C29 | 113.8 (3) |
C3—C4—C5 | 116.6 (5) | O9—C30—H30A | 108.8 |
C3—C4—C6 | 124.6 (6) | C29—C30—H30A | 108.8 |
C5—C4—C6 | 118.7 (6) | O9—C30—H30B | 108.8 |
N1—C5—C4 | 122.2 (5) | C29—C30—H30B | 108.8 |
N1—C5—C9 | 118.7 (4) | H30A—C30—H30B | 107.7 |
C4—C5—C9 | 119.0 (4) | O9—C31—C36 | 113.6 (9) |
C7—C6—C4 | 121.5 (6) | O9—C31—C32 | 124.2 (9) |
C7—C6—H6 | 119.2 | C36—C31—C32 | 122.2 (9) |
C4—C6—H6 | 119.2 | C31—C32—C33 | 117.6 (9) |
C6—C7—C8 | 121.3 (6) | C31—C32—H32 | 121.2 |
C6—C7—H7 | 119.4 | C33—C32—H32 | 121.2 |
C8—C7—H7 | 119.4 | C34—C33—C32 | 118.1 (9) |
C10—C8—C7 | 123.0 (5) | C34—C33—H33 | 120.9 |
C10—C8—C9 | 117.3 (5) | C32—C33—H33 | 120.9 |
C7—C8—C9 | 119.7 (6) | C33—C34—C35 | 125.4 (9) |
N2—C9—C5 | 118.3 (4) | C33—C34—H34 | 117.3 |
N2—C9—C8 | 122.2 (5) | C35—C34—H34 | 117.3 |
C5—C9—C8 | 119.5 (5) | C36—C35—C34 | 116.6 (9) |
C11—C10—C8 | 120.4 (5) | C36—C35—H35 | 121.7 |
C11—C10—H10 | 119.8 | C34—C35—H35 | 121.7 |
C8—C10—H10 | 119.8 | C35—C36—C31 | 120.0 (10) |
C10—C11—C12 | 119.1 (5) | C35—C36—H36 | 120.0 |
C10—C11—H11 | 120.4 | C31—C36—H36 | 120.0 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O7iii | 0.93 | 2.34 | 3.212 (6) | 156 |
C30—H30B···O4iv | 0.97 | 2.42 | 3.370 (5) | 165 |
C12—H12···O5ii | 0.93 | 2.46 | 3.049 (6) | 121 |
C1—H1···O2i | 0.93 | 2.44 | 3.128 (6) | 131 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ce(C8H7O3)3(C12H8N2)] |
Mr | 773.73 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 20.025 (3), 8.621 (3), 20.7996 (18) |
β (°) | 106.982 (5) |
V (Å3) | 3434.4 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.38 |
Crystal size (mm) | 0.33 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.661, 0.896 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25231, 6830, 4757 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.622 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.096, 1.01 |
No. of reflections | 6830 |
No. of parameters | 403 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.05, −0.64 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.
Ce1—O1 | 2.491 (3) | Ce1—O8 | 2.855 (3) |
Ce1—O4 | 2.434 (3) | Ce1—N1 | 2.730 (3) |
Ce1—O7 | 2.581 (3) | Ce1—N2 | 2.723 (3) |
O1—Ce1—O4 | 146.07 (9) | O7—Ce1—N1 | 64.23 (10) |
O1—Ce1—O7 | 72.71 (9) | O8—Ce1—N1 | 102.45 (9) |
O1—Ce1—O8 | 64.70 (8) | O1—Ce1—N2 | 80.99 (10) |
O4—Ce1—O7 | 139.55 (9) | O4—Ce1—N2 | 96.35 (9) |
O4—Ce1—O8 | 140.03 (8) | O7—Ce1—N2 | 74.83 (9) |
O7—Ce1—O8 | 47.47 (8) | O8—Ce1—N2 | 118.33 (9) |
O1—Ce1—N1 | 127.21 (10) | N1—Ce1—N2 | 59.91 (11) |
O4—Ce1—N1 | 77.08 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O7i | 0.93 | 2.34 | 3.212 (6) | 156 |
C30—H30B···O4ii | 0.97 | 2.42 | 3.370 (5) | 165 |
C12—H12···O5iii | 0.93 | 2.46 | 3.049 (6) | 121 |
C1—H1···O2iv | 0.93 | 2.44 | 3.128 (6) | 131 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+2; (iv) −x+2, −y, −z+2. |
In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Daiguebonne et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The two N atoms of 1,10-phenanthroline (phen) ligand and four O atoms of three phenoxyacetic acid ligands are coordinated to the Ce atom. The Ce—O and Ce—N bonds are in the range of [2.434 (3)–2.855 (3) Å] and [2.723 (3)–2.730 (3) Å], respectively, (Table 1).
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) lead to a supramolecular network structure (Fig. 2), in which they may be effective in the stabilization of the structure.