[UO2(acac)2(ppp)] is constructed from one uranyl(VI) unit, two anionic acetylacetonate (acac) ligands and one 1-phenyl-3-(pyridin-4-yl)propane (ppp) ligand. The U atom exhibits a UNO6 pentagonal–bipyramidal coordination geometry; two uranyl(VI) O atoms are located at the axial positions, whereas four O atoms from two chelating bidentate acac ligands and one N atom of a ppp ligand form the equatorial plane.
Keywords: crystal structure; pentane-2,4-dionate; 1-phenyl-3-(pyridin-4-yl)propane; uranium(VI) complex
Abstract
In the title compound, [UO2(C5H7O2)2(C14H15N)], the uranyl(VI) unit ([O=U=O]2+) is coordinated to two acetylacetonate (acac) anions and one 1-phenyl-3-(pyridin-4-yl)propane (ppp) molecule. The geometry around the U atom is UNO6 pentagonal–bipyramidal; two uranyl(VI) O atoms are located at the axial positions, whereas four O atoms from two chelating bidentate acac ligands and one N atom of a ppp ligand form the equatorial plane.
Chemical context
The structural properties of uranyl(VI) complexes are interesting from the viewpoint of nuclear fuels reprocessing and actinide waste treatment. In most commercial reprocessing plants, spent nuclear fuels are treated by the Purex method, in which uranium and plutonium are extracted from a nitric acid solution of spent nuclear fuels using tributyl-phosphate/n-dodecane. Uranium in the nitric acid solution exists as uranyl(VI) ([O=U=O]2+) complexes. However, the Purex method has a few problems; for example, as the processing takes place on a relatively large scale, a large amount of extractant is necessary (Ikeda et al., 2004 ▸; Suzuki et al., 2012 ▸) Attempts to find other suitable coordinating ligands are therefore being undertaken. A number of structural studies of uranyl(VI) β-diketonate complexes have been reported by ourselves and others (Alcock et al., 1984 ▸, 1987 ▸; Huuskonen et al., 2007 ▸; Kannan et al., 2001 ▸; Kawasaki & Kitazawa, 2008 ▸; Kawasaki et al., 2010 ▸; Sidorenko et al., 2009 ▸; Tahir et al., 2006 ▸; Takao & Ikeda, 2008 ▸). In particular, acetylacetonate (acac), is the simplest β-diketonate ligand and an important coordinating ligand for uranium. 
We report herein the synthesis and crystal structure of a novel uranyl(VI) acetylacetonate (acac) complex with the pyridine-based ligand ppp [ppp = 1-phenyl-3-(pyridin-4-yl)propane] (Seth, 2014 ▸), namely, [UO2(acac)2(ppp)].
Structural commentary
The title compound of formula [UO2(C5H7O2)2(C14H15N)], is constructed from one uranyl(VI) ([O=U=O]2+) unit, two acetylacetonate anions and one molecule of ppp (Fig. 1 ▸). The uranium(VI) atom exhibits a pentagonal–bipyramidal coordination geometry: two uranyl(VI) oxygen atoms (O1 and O2) are located in the axial positions and four oxygen atoms (O3, O4, O5 and O6) from two chelating bidentate acac ions, together with one nitrogen atom (N1) of the ppp molecule, form the equatorial plane. The bond lengths around U1 (Table 1 ▸) decrease in the order U—N > U—Oacac > U=O. The dihedral angle between the pyridine ring of the ppp molecule and the equatorial plane around U1 is 49.43 (12)°. The above structural properties are similar to those in the majority of previously characterised [UO2(acac)2 L] (L = pyridine derivative ligand) complexes (Alcock et al., 1984 ▸; Kawasaki & Kitazawa, 2008 ▸; Kawasaki et al., 2010 ▸). The conformation of the ppp molecule is GG′ (Fig. 2 ▸). The dihedral angle between the pyridine ring and the phenyl ring in the ppp molecule is 26.96 (13)°.
Figure 1.
The molecular structure of [UO2(acac)2(ppp)]. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
Table 1. Selected geometric parameters (, ).
| U1O1 | 1.773(3) | U1O5 | 2.348(2) |
| U1O2 | 1.777(3) | U1O6 | 2.354(2) |
| U1O3 | 2.330(2) | U1N1 | 2.610(3) |
| U1O4 | 2.360(2) | ||
| O1U1O2 | 179.19(11) | O1U1N1 | 86.45(11) |
| O3U1O4 | 70.88(9) | O2U1N1 | 92.74(11) |
| O3U1O6 | 138.83(9) | O3U1N1 | 69.37(9) |
| O4U1O5 | 79.13(9) | O6U1N1 | 70.15(9) |
| O5U1O6 | 70.91(9) |
Figure 2.
The four possible conformations that the ppp ligand can form (based on Carlucci et al., 2002 ▸). In the title compound, the conformation is GG′.
Supramolecular features
A packing diagram of title complex is shown in Fig. 3 ▸. The molecules are stacked along the b axis, held together by van der Waals’ interactions only. Significant intermolecular π–π and C—H⋯π interactions are not found.
Figure 3.
A packing diagram of the title complex (red line: a axis; green line: b axis; blue line: c axis). Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
Synthesis and crystallization
The title complex was synthesized according to literature procedures (Alcock et al., 1984 ▸, 1987 ▸; Kawasaki & Kitazawa, 2008 ▸; Kawasaki et al., 2010 ▸). To 10 ml of a methanolic solution containing 1 mmol UO2(NO3)2·6H2O was added 3 mmol of acetylacetone and 3 mmol of 1-phenyl-3-(pyridin-4-yl)propane in 5 ml MeOH. The solvent evaporated slowly at room temperature for a few days and orange crystal were obtained.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were placed at calculated positions [C(CH)—H = 0.93, C(CH2)—H = 0.97 and C(CH3)—H = 0.96Å] and allowed to ride on their parent atoms with U iso(H) = 1.2U eq(CH,CH2) and U iso(H) = 1.5U eq(CH3).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | [UO2(C5H7O2)2(C14H15N)] |
| M r | 665.51 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 297 |
| a, b, c () | 8.2100(16), 11.530(2), 14.516(3) |
| , , () | 108.67(3), 98.50(3), 100.81(3) |
| V (3) | 1246.4(4) |
| Z | 2 |
| Radiation type | Mo K |
| (mm1) | 6.55 |
| Crystal size (mm) | 0.47 0.29 0.26 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII |
| Absorption correction | Analytical (XPREP; Bruker, 2007 ▸) |
| T min, T max | 0.149, 0.281 |
| No. of measured, independent and observed [I > 2(I)] reflections | 9353, 6948, 6026 |
| R int | 0.015 |
| (sin /)max (1) | 0.722 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.027, 0.056, 0.99 |
| No. of reflections | 6948 |
| No. of parameters | 293 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.88, 0.64 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014026607/cq2012sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026607/cq2012Isup2.hkl
CCDC reference: 1037284
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported by a MEXT (Ministry of Education, Culture, Sports, Science and Technology, Japan)-Supported Program for the Strategic Research Foundation at Private Universities 2012–2016.
supplementary crystallographic information
Crystal data
| [U(C5H7O2)2O2(C14H15N)] | Z = 2 |
| Mr = 665.51 | F(000) = 640 |
| Triclinic, P1 | Dx = 1.773 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.2100 (16) Å | Cell parameters from 4311 reflections |
| b = 11.530 (2) Å | θ = 2.6–28.5° |
| c = 14.516 (3) Å | µ = 6.55 mm−1 |
| α = 108.67 (3)° | T = 297 K |
| β = 98.50 (3)° | Block, orange |
| γ = 100.81 (3)° | 0.47 × 0.29 × 0.26 mm |
| V = 1246.4 (4) Å3 |
Data collection
| Bruker SMART APEXII diffractometer | 6948 independent reflections |
| Radiation source: fine-focus sealed tube | 6026 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.015 |
| Detector resolution: 8.333 pixels mm-1 | θmax = 30.9°, θmin = 1.9° |
| ω scans | h = −11→9 |
| Absorption correction: analytical (XPREP; Bruker, 2007) | k = −16→15 |
| Tmin = 0.149, Tmax = 0.281 | l = −14→20 |
| 9353 measured reflections |
Refinement
| 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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.056 | H-atom parameters constrained |
| S = 0.99 | w = 1/[σ2(Fo2) + (0.0257P)2] where P = (Fo2 + 2Fc2)/3 |
| 6948 reflections | (Δ/σ)max = 0.003 |
| 293 parameters | Δρmax = 0.88 e Å−3 |
| 0 restraints | Δρmin = −0.64 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 > 2σ(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)
| x | y | z | Uiso*/Ueq | ||
| U1 | 0.488854 (15) | 0.690915 (11) | 0.372080 (8) | 0.03519 (4) | |
| O1 | 0.3391 (3) | 0.5504 (2) | 0.3581 (2) | 0.0535 (6) | |
| O2 | 0.6386 (3) | 0.8327 (2) | 0.38786 (19) | 0.0525 (6) | |
| O3 | 0.6977 (3) | 0.6473 (3) | 0.47398 (18) | 0.0566 (7) | |
| O4 | 0.6471 (3) | 0.5741 (2) | 0.27211 (18) | 0.0521 (6) | |
| O5 | 0.3569 (4) | 0.6784 (3) | 0.21310 (17) | 0.0579 (7) | |
| O6 | 0.2846 (3) | 0.8105 (3) | 0.38825 (18) | 0.0567 (7) | |
| N1 | 0.4613 (4) | 0.7730 (3) | 0.55740 (19) | 0.0397 (6) | |
| C1 | 0.9705 (6) | 0.6794 (5) | 0.5706 (3) | 0.0810 (14) | |
| H1A | 0.9878 | 0.7680 | 0.6071 | 0.121* | |
| H1B | 1.0774 | 0.6618 | 0.5601 | 0.121* | |
| H1C | 0.9231 | 0.6316 | 0.6080 | 0.121* | |
| C2 | 0.8488 (5) | 0.6426 (3) | 0.4705 (3) | 0.0493 (9) | |
| C3 | 0.9047 (5) | 0.6043 (4) | 0.3827 (3) | 0.0573 (10) | |
| H3 | 1.0188 | 0.6043 | 0.3872 | 0.069* | |
| C4 | 0.8004 (5) | 0.5661 (3) | 0.2886 (3) | 0.0497 (9) | |
| C5 | 0.8646 (7) | 0.5049 (5) | 0.1981 (4) | 0.0757 (14) | |
| H5A | 0.7867 | 0.4249 | 0.1584 | 0.114* | |
| H5B | 0.9744 | 0.4920 | 0.2186 | 0.114* | |
| H5C | 0.8738 | 0.5586 | 0.1595 | 0.114* | |
| C6 | 0.2066 (7) | 0.6847 (5) | 0.0645 (3) | 0.0796 (15) | |
| H6A | 0.3049 | 0.7172 | 0.0433 | 0.119* | |
| H6B | 0.1140 | 0.7170 | 0.0434 | 0.119* | |
| H6C | 0.1752 | 0.5940 | 0.0354 | 0.119* | |
| C7 | 0.2466 (5) | 0.7251 (4) | 0.1764 (3) | 0.0496 (9) | |
| C8 | 0.1637 (5) | 0.8067 (4) | 0.2321 (3) | 0.0560 (10) | |
| H8 | 0.0878 | 0.8375 | 0.1980 | 0.067* | |
| C9 | 0.1856 (4) | 0.8459 (3) | 0.3350 (3) | 0.0473 (8) | |
| C10 | 0.0891 (6) | 0.9354 (4) | 0.3879 (3) | 0.0670 (12) | |
| H10A | −0.0194 | 0.8881 | 0.3894 | 0.101* | |
| H10B | 0.0723 | 0.9919 | 0.3531 | 0.101* | |
| H10C | 0.1526 | 0.9833 | 0.4549 | 0.101* | |
| C11 | 0.4545 (5) | 0.6962 (3) | 0.6101 (3) | 0.0449 (8) | |
| H11 | 0.4583 | 0.6129 | 0.5791 | 0.054* | |
| C12 | 0.4422 (5) | 0.7361 (4) | 0.7083 (3) | 0.0479 (8) | |
| H12 | 0.4371 | 0.6798 | 0.7421 | 0.058* | |
| C13 | 0.4373 (4) | 0.8594 (3) | 0.7568 (2) | 0.0434 (8) | |
| C14 | 0.4484 (5) | 0.9381 (3) | 0.7028 (3) | 0.0476 (8) | |
| H14 | 0.4501 | 1.0227 | 0.7333 | 0.057* | |
| C15 | 0.4570 (5) | 0.8929 (3) | 0.6042 (3) | 0.0470 (8) | |
| H15 | 0.4599 | 0.9474 | 0.5688 | 0.056* | |
| C16 | 0.4135 (6) | 0.9028 (4) | 0.8628 (3) | 0.0576 (10) | |
| H16A | 0.4701 | 0.9919 | 0.8956 | 0.069* | |
| H16B | 0.4675 | 0.8568 | 0.8984 | 0.069* | |
| C17 | 0.2268 (6) | 0.8831 (4) | 0.8692 (3) | 0.0586 (10) | |
| H17A | 0.1655 | 0.7980 | 0.8253 | 0.070* | |
| H17B | 0.2195 | 0.8901 | 0.9367 | 0.070* | |
| C18 | 0.1404 (5) | 0.9765 (4) | 0.8412 (3) | 0.0536 (9) | |
| H18A | 0.1565 | 0.9747 | 0.7759 | 0.064* | |
| H18B | 0.0192 | 0.9492 | 0.8361 | 0.064* | |
| C19 | 0.2056 (5) | 1.1116 (4) | 0.9144 (3) | 0.0488 (8) | |
| C20 | 0.1846 (6) | 1.1420 (4) | 1.0114 (3) | 0.0621 (11) | |
| H20 | 0.1317 | 1.0788 | 1.0318 | 0.075* | |
| C21 | 0.2424 (6) | 1.2672 (5) | 1.0796 (3) | 0.0750 (14) | |
| H21 | 0.2255 | 1.2868 | 1.1442 | 0.090* | |
| C22 | 0.3239 (6) | 1.3604 (5) | 1.0503 (4) | 0.0772 (14) | |
| H22 | 0.3654 | 1.4431 | 1.0952 | 0.093* | |
| C23 | 0.3428 (7) | 1.3292 (5) | 0.9534 (4) | 0.0796 (14) | |
| H23 | 0.3952 | 1.3923 | 0.9328 | 0.096* | |
| C24 | 0.2867 (6) | 1.2082 (4) | 0.8869 (3) | 0.0627 (11) | |
| H24 | 0.3030 | 1.1900 | 0.8222 | 0.075* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| U1 | 0.03593 (7) | 0.03608 (7) | 0.03601 (7) | 0.01545 (5) | 0.00830 (5) | 0.01242 (5) |
| O1 | 0.0494 (15) | 0.0444 (15) | 0.0616 (16) | 0.0058 (12) | 0.0129 (12) | 0.0154 (12) |
| O2 | 0.0563 (16) | 0.0411 (14) | 0.0611 (16) | 0.0096 (12) | 0.0197 (13) | 0.0182 (12) |
| O3 | 0.0536 (16) | 0.078 (2) | 0.0503 (14) | 0.0391 (15) | 0.0132 (12) | 0.0262 (14) |
| O4 | 0.0537 (16) | 0.0575 (16) | 0.0478 (14) | 0.0285 (13) | 0.0151 (12) | 0.0124 (12) |
| O5 | 0.0669 (18) | 0.0722 (19) | 0.0417 (13) | 0.0421 (15) | 0.0081 (12) | 0.0175 (13) |
| O6 | 0.0607 (17) | 0.0762 (19) | 0.0453 (13) | 0.0456 (15) | 0.0134 (12) | 0.0208 (13) |
| N1 | 0.0469 (16) | 0.0383 (15) | 0.0385 (14) | 0.0166 (13) | 0.0148 (12) | 0.0141 (12) |
| C1 | 0.067 (3) | 0.093 (4) | 0.075 (3) | 0.026 (3) | −0.012 (2) | 0.029 (3) |
| C2 | 0.046 (2) | 0.043 (2) | 0.062 (2) | 0.0183 (16) | 0.0049 (17) | 0.0212 (17) |
| C3 | 0.0358 (19) | 0.065 (3) | 0.079 (3) | 0.0201 (18) | 0.0187 (19) | 0.030 (2) |
| C4 | 0.052 (2) | 0.044 (2) | 0.068 (2) | 0.0230 (17) | 0.0303 (19) | 0.0257 (18) |
| C5 | 0.093 (4) | 0.072 (3) | 0.086 (3) | 0.043 (3) | 0.054 (3) | 0.032 (3) |
| C6 | 0.092 (4) | 0.107 (4) | 0.046 (2) | 0.048 (3) | 0.004 (2) | 0.029 (2) |
| C7 | 0.048 (2) | 0.056 (2) | 0.0462 (19) | 0.0167 (18) | 0.0018 (16) | 0.0232 (17) |
| C8 | 0.055 (2) | 0.064 (3) | 0.052 (2) | 0.030 (2) | 0.0006 (18) | 0.0204 (19) |
| C9 | 0.0377 (18) | 0.043 (2) | 0.058 (2) | 0.0173 (15) | 0.0035 (16) | 0.0130 (17) |
| C10 | 0.062 (3) | 0.068 (3) | 0.071 (3) | 0.040 (2) | 0.011 (2) | 0.014 (2) |
| C11 | 0.057 (2) | 0.0391 (19) | 0.0473 (19) | 0.0229 (16) | 0.0172 (17) | 0.0184 (15) |
| C12 | 0.060 (2) | 0.049 (2) | 0.0470 (19) | 0.0214 (18) | 0.0182 (17) | 0.0262 (17) |
| C13 | 0.0427 (19) | 0.048 (2) | 0.0362 (16) | 0.0154 (16) | 0.0057 (14) | 0.0101 (15) |
| C14 | 0.060 (2) | 0.0379 (19) | 0.0438 (18) | 0.0158 (17) | 0.0158 (17) | 0.0096 (15) |
| C15 | 0.062 (2) | 0.0379 (19) | 0.0488 (19) | 0.0157 (17) | 0.0215 (17) | 0.0192 (16) |
| C16 | 0.076 (3) | 0.066 (3) | 0.0361 (18) | 0.034 (2) | 0.0081 (18) | 0.0178 (18) |
| C17 | 0.079 (3) | 0.055 (2) | 0.051 (2) | 0.021 (2) | 0.029 (2) | 0.0227 (19) |
| C18 | 0.052 (2) | 0.057 (2) | 0.053 (2) | 0.0113 (18) | 0.0174 (18) | 0.0191 (19) |
| C19 | 0.0391 (19) | 0.058 (2) | 0.048 (2) | 0.0161 (17) | 0.0076 (16) | 0.0160 (18) |
| C20 | 0.063 (3) | 0.065 (3) | 0.056 (2) | 0.015 (2) | 0.018 (2) | 0.017 (2) |
| C21 | 0.073 (3) | 0.084 (4) | 0.058 (3) | 0.033 (3) | 0.011 (2) | 0.007 (2) |
| C22 | 0.069 (3) | 0.051 (3) | 0.094 (4) | 0.018 (2) | −0.001 (3) | 0.009 (3) |
| C23 | 0.081 (3) | 0.053 (3) | 0.103 (4) | 0.013 (2) | 0.019 (3) | 0.029 (3) |
| C24 | 0.064 (3) | 0.063 (3) | 0.069 (3) | 0.021 (2) | 0.019 (2) | 0.030 (2) |
Geometric parameters (Å, º)
| U1—O1 | 1.773 (3) | C10—H10A | 0.9600 |
| U1—O2 | 1.777 (3) | C10—H10B | 0.9600 |
| U1—O3 | 2.330 (2) | C10—H10C | 0.9600 |
| U1—O4 | 2.360 (2) | C11—C12 | 1.376 (5) |
| U1—O5 | 2.348 (2) | C11—H11 | 0.9300 |
| U1—O6 | 2.354 (2) | C12—C13 | 1.382 (5) |
| U1—N1 | 2.610 (3) | C12—H12 | 0.9300 |
| O3—C2 | 1.260 (4) | C13—C14 | 1.375 (5) |
| O4—C4 | 1.272 (4) | C13—C16 | 1.512 (5) |
| O5—C7 | 1.271 (4) | C14—C15 | 1.375 (5) |
| O6—C9 | 1.251 (4) | C14—H14 | 0.9300 |
| N1—C11 | 1.342 (4) | C15—H15 | 0.9300 |
| N1—C15 | 1.342 (4) | C16—C17 | 1.528 (6) |
| C1—C2 | 1.519 (5) | C16—H16A | 0.9700 |
| C1—H1A | 0.9600 | C16—H16B | 0.9700 |
| C1—H1B | 0.9600 | C17—C18 | 1.519 (5) |
| C1—H1C | 0.9600 | C17—H17A | 0.9700 |
| C2—C3 | 1.384 (6) | C17—H17B | 0.9700 |
| C3—C4 | 1.386 (6) | C18—C19 | 1.517 (6) |
| C3—H3 | 0.9300 | C18—H18A | 0.9700 |
| C4—C5 | 1.501 (5) | C18—H18B | 0.9700 |
| C5—H5A | 0.9600 | C19—C20 | 1.382 (5) |
| C5—H5B | 0.9600 | C19—C24 | 1.389 (6) |
| C5—H5C | 0.9600 | C20—C21 | 1.407 (6) |
| C6—C7 | 1.505 (5) | C20—H20 | 0.9300 |
| C6—H6A | 0.9600 | C21—C22 | 1.375 (7) |
| C6—H6B | 0.9600 | C21—H21 | 0.9300 |
| C6—H6C | 0.9600 | C22—C23 | 1.375 (7) |
| C7—C8 | 1.385 (5) | C22—H22 | 0.9300 |
| C8—C9 | 1.388 (5) | C23—C24 | 1.362 (6) |
| C8—H8 | 0.9300 | C23—H23 | 0.9300 |
| C9—C10 | 1.504 (5) | C24—H24 | 0.9300 |
| O1—U1—O2 | 179.19 (11) | O6—C9—C8 | 122.9 (3) |
| O1—U1—O3 | 91.86 (12) | O6—C9—C10 | 116.8 (3) |
| O1—U1—O4 | 91.38 (11) | C8—C9—C10 | 120.3 (3) |
| O1—U1—O5 | 89.82 (12) | C9—C10—H10A | 109.5 |
| O1—U1—O6 | 92.85 (12) | C9—C10—H10B | 109.5 |
| O2—U1—O3 | 87.91 (12) | H10A—C10—H10B | 109.5 |
| O2—U1—O4 | 89.27 (11) | C9—C10—H10C | 109.5 |
| O2—U1—O5 | 90.77 (12) | H10A—C10—H10C | 109.5 |
| O2—U1—O6 | 86.82 (11) | H10B—C10—H10C | 109.5 |
| O3—U1—O4 | 70.88 (9) | N1—C11—C12 | 122.5 (3) |
| O3—U1—O5 | 149.99 (9) | N1—C11—H11 | 118.8 |
| O3—U1—O6 | 138.83 (9) | C12—C11—H11 | 118.8 |
| O4—U1—O5 | 79.13 (9) | C11—C12—C13 | 120.3 (3) |
| O4—U1—O6 | 149.71 (9) | C11—C12—H12 | 119.8 |
| O5—U1—O6 | 70.91 (9) | C13—C12—H12 | 119.8 |
| O1—U1—N1 | 86.45 (11) | C14—C13—C12 | 116.7 (3) |
| O2—U1—N1 | 92.74 (11) | C14—C13—C16 | 122.3 (3) |
| O3—U1—N1 | 69.37 (9) | C12—C13—C16 | 121.0 (3) |
| O4—U1—N1 | 140.08 (8) | C15—C14—C13 | 120.7 (3) |
| O5—U1—N1 | 140.62 (9) | C15—C14—H14 | 119.6 |
| O6—U1—N1 | 70.15 (9) | C13—C14—H14 | 119.6 |
| C2—O3—U1 | 132.2 (2) | N1—C15—C14 | 122.3 (3) |
| C4—O4—U1 | 132.7 (2) | N1—C15—H15 | 118.9 |
| C7—O5—U1 | 137.4 (2) | C14—C15—H15 | 118.9 |
| C9—O6—U1 | 139.2 (2) | C13—C16—C17 | 113.2 (3) |
| C11—N1—C15 | 117.5 (3) | C13—C16—H16A | 108.9 |
| C11—N1—U1 | 120.6 (2) | C17—C16—H16A | 108.9 |
| C15—N1—U1 | 121.9 (2) | C13—C16—H16B | 108.9 |
| C2—C1—H1A | 109.5 | C17—C16—H16B | 108.9 |
| C2—C1—H1B | 109.5 | H16A—C16—H16B | 107.7 |
| H1A—C1—H1B | 109.5 | C18—C17—C16 | 113.9 (3) |
| C2—C1—H1C | 109.5 | C18—C17—H17A | 108.8 |
| H1A—C1—H1C | 109.5 | C16—C17—H17A | 108.8 |
| H1B—C1—H1C | 109.5 | C18—C17—H17B | 108.8 |
| O3—C2—C3 | 123.9 (4) | C16—C17—H17B | 108.8 |
| O3—C2—C1 | 115.6 (4) | H17A—C17—H17B | 107.7 |
| C3—C2—C1 | 120.5 (4) | C19—C18—C17 | 114.2 (3) |
| C2—C3—C4 | 123.8 (3) | C19—C18—H18A | 108.7 |
| C2—C3—H3 | 118.1 | C17—C18—H18A | 108.7 |
| C4—C3—H3 | 118.1 | C19—C18—H18B | 108.7 |
| O4—C4—C3 | 124.5 (3) | C17—C18—H18B | 108.7 |
| O4—C4—C5 | 115.8 (4) | H18A—C18—H18B | 107.6 |
| C3—C4—C5 | 119.7 (4) | C20—C19—C24 | 117.9 (4) |
| C4—C5—H5A | 109.5 | C20—C19—C18 | 120.4 (4) |
| C4—C5—H5B | 109.5 | C24—C19—C18 | 121.7 (4) |
| H5A—C5—H5B | 109.5 | C19—C20—C21 | 120.9 (4) |
| C4—C5—H5C | 109.5 | C19—C20—H20 | 119.5 |
| H5A—C5—H5C | 109.5 | C21—C20—H20 | 119.5 |
| H5B—C5—H5C | 109.5 | C22—C21—C20 | 119.7 (5) |
| C7—C6—H6A | 109.5 | C22—C21—H21 | 120.1 |
| C7—C6—H6B | 109.5 | C20—C21—H21 | 120.1 |
| H6A—C6—H6B | 109.5 | C21—C22—C23 | 118.8 (5) |
| C7—C6—H6C | 109.5 | C21—C22—H22 | 120.6 |
| H6A—C6—H6C | 109.5 | C23—C22—H22 | 120.6 |
| H6B—C6—H6C | 109.5 | C24—C23—C22 | 121.7 (5) |
| O5—C7—C8 | 124.5 (3) | C24—C23—H23 | 119.1 |
| O5—C7—C6 | 115.5 (4) | C22—C23—H23 | 119.1 |
| C8—C7—C6 | 120.0 (3) | C23—C24—C19 | 120.8 (4) |
| C7—C8—C9 | 124.8 (3) | C23—C24—H24 | 119.6 |
| C7—C8—H8 | 117.6 | C19—C24—H24 | 119.6 |
| C9—C8—H8 | 117.6 |
References
- Alcock, N. W., Flanders, D. J. & Brown, D. (1984). J. Chem. Soc. Dalton Trans. pp. 679–681.
- Alcock, N. W., Flanders, D. J., Pennington, M. & Brown, D. (1987). Acta Cryst. C43, 1476–1480.
- Bruker (2007). APEX2, XSCANS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
- Carlucci, L., Ciani, G., Proserpio, D. M. & Rizzato, S. (2002). CrystEngComm, 4, 121–129.
- Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
- Huuskonen, J., Raatikainen, K. & Rissanen, K. (2007). Acta Cryst. E63, m413–m414.
- Ikeda, Y., Wada, E., Harada, M., Chikazawa, T., Kikuchi, T., Mineo, H., Morita, Y., Nogami, M. & Suzuki, K. (2004). J. Alloys Compd, 374, 420–425.
- Kannan, S., Shanmugasundara Raj, S. & Fun, H.-K. (2001). Polyhedron, 20, 2145–2150.
- Kawasaki, T. & Kitazawa, T. (2008). Acta Cryst. E64, m788. [DOI] [PMC free article] [PubMed]
- Kawasaki, T., Nishimura, T. & Kitazawa, T. (2010). Bull. Chem. Soc. Jpn, 83, 1528–1530.
- Seth, S. K. (2014). J. Mol. Struct. 1070, 65–74.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Sidorenko, G. V., Grigor’ev, M. S., Gurzhiy, V. V., Suglobov, D. N. & Tananaev, I. G. (2009). Radiochemistry, 51, 345–349.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Suzuki, T., Kawasaki, T., Takao, K., Harada, M., Nogami, M. & Ikeda, Y. (2012). J. Nucl. Sci. Technol. 49, 1010–1017.
- Tahir, A. A., Hamid, M., Mazhar, M., Zeller, M. & Hunter, A. D. (2006). Acta Cryst. E62, m1780–m1781.
- Takao, K. & Ikeda, Y. (2008). Acta Cryst. E64, m219–m220. [DOI] [PMC free article] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014026607/cq2012sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026607/cq2012Isup2.hkl
CCDC reference: 1037284
Additional supporting information: crystallographic information; 3D view; checkCIF report