Bis(2-benzoyl-1-phenyl­ethenolato-κ2O,O′)(ethanol-κO)dioxidouranium(VI)

Takao, K.; Ikeda, Y.

doi:10.1107/S1600536807063799

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages m219-m220

https://doi.org/10.1107/S1600536807063799

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Bis(2-benzoyl-1-phenylethenolato-κ²O,O′)(ethanol-κO)dioxidouranium(VI)

Koichiro Takao ^a and Yasuhisa Ikeda ^a ^*

^aResearch Laboratory for Nuclear Reactors, Tokyo Institute of Technology, 2-12-1-N1-34, O-okayama, Meguro-ku, Tokyo 152-8550, Japan
^*Correspondence e-mail: yikeda@nr.titach.ac.jp

(Received 21 November 2007; accepted 27 November 2007; online 18 December 2007)

In the title compound, [U(C₁₅H₁₁O₂)₂O₂(C₂H₆O)], the U^VIatom has a pentagonal–bipyramidal coordination geometry. The two so-called `-yl' O atoms occupy the axial positions whereas four O atoms from the two chelating dibenzoylmethanate ligands and the O atom from the ethanol molecule are situated in the equatorial plane. Intermolecular hydrogen bonds between one of the `-yl' O atoms and the ethanol OH group assemble molecules into a centrosymmetric dimer.

Related literature

For literature on the structural chemistry of uranyl(VI) complexes with dibenzoylmethanate and unidentate ligands, see: Alagar et al. (2003 , 2004 ); Fun, Kannan, Chantrapromma et al. (2002 ); Fun, Kannan, Usman et al. (2002 ); Kannan & Gerguson (1997 ); Kannan et al. (1995 , 1997 , 2000 ); Linert et al. (2001 ); Mizuoka & Ikeda (2004 ); Rajagopal et al. (2002 ).

Experimental

Crystal data

[U(C₁₅H₁₁O₂)₂O₂(C₂H₆O)]
M_r = 762.57
Monoclinic, P 2₁ /c
a = 9.088 (5) Å
b = 12.141 (7) Å
c = 25.878 (13) Å
β = 99.126 (16)°
V = 2819 (3) Å³
Z = 4
Mo Kα radiation
μ = 5.81 mm⁻¹
T = 173 (2) K
0.40 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (Higashi, 1999 ) T_min = 0.205, T_max = 0.594
26257 measured reflections
6442 independent reflections
4539 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.083
S = 1.01
6442 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected bond lengths (Å)

U1—O1	1.762 (4)
U1—O2	1.787 (4)
U1—O4	2.288 (4)
U1—O6	2.339 (4)
U1—O5	2.347 (4)
U1—O3	2.365 (4)
U1—O7	2.464 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H6⋯O2ⁱ	0.86	1.94	2.765 (5)	162
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (MSC/Rigaku, 2006 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ) and DIRDIF99 (Beurskens et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807063799/gk2123sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063799/gk2123Isup2.hkl

checkCIF report

Comment top

Structural chemistry of uranyl(VI) complexes with dibenzoylmethanate (dbm) and unidentate ligands (L) has been extensively explored (Kannan et al., 1997a,b, 1995, 2000; Rajagopal et al., 2002; Fun, Kannan, S., Chantrapromma et al. 2002;Fun, Kannan, S., Usman et al. 2002 Alagar et al., 2003, 2004). Generally, two dbm and one L are placed in an equatorial plane of the uranyl(VI) ion (UO₂²⁺). This results in a UO₂(dbm)₂L complex with a pentagonal-bipyramidal geometry around the uranium atom. In our previous study, we also used UO₂(dbm)₂DMSO complex (DMSO = dimethyl sulfoxide) as a precursor of a corresponding uranyl(V) complex, [U^VO₂(dbm)₂DMSO]^- (Mizuoka & Ikeda, 2004). In our recent experiment, we obtained crystals of the title compound, UO₂(dbm)₂EtOH (I), suitable for single-crystal X-ray analysis. In this paper, we report results of the structure determination of I to accumulate more structural data in a series of UO₂(dbm)₂L complexes.

The molecular structure of I is shown in Fig. 1. The uranium atom in I is surrounded by seven O atoms; two O are at the axial positions, and the remaining five O from dbm and EtOH in the equatorial plane. As a consequence, the coordination geometry around U in I is pentagonal bipyramidal. The deviations of the O atoms in dbm and EtOH from the equatorial plane are within 0.1 Å.

Bond lengths in I are listed in Table 1, and are similar to the structural parameters of other UO₂(dbm)₂L complexes reported previously. As an exception, the bond length between U and O of EtOH [U1–O7 = 2.464 (4) Å] seems to be slightly longer than the corresponding bond lengths in the UO₂(dbm)₂L complexes (L = di-substituted sulfoxides, dibenzoylacetone, and triphenylphosphine oxide), while shorter than those with H₂O, malonanilide, and camphor. It is likely that the bond length between U and O of L (U–O_L) depends on donicity of L (Linert et al. 2001). In this discussion, the steric effect of L should also be taken into account. However, it is not the case of I, because there seems to be no significant steric hindrance due to EtOH in its molecular structure shown in Fig. 1.

Intermolecular hydrogen bond between OH group of ethanol and the -yl oxygen, O7–H6···O2ⁱ [symmetry operation: (i) 1 - x, 1 - y, 1 - z], was observed between the neighboring complex molecules (Table 2). This results in a dimeric aggregate of I as shown in Fig. 2.

Related literature top

For literature on the structural chemistry of uranyl(VI) complexes with dibenzoylmethanate and unidentate ligands, see: Alagar et al. (2003, 2004); Fun, Kannan, Chantrapromma et al. (2002); Fun, Kannan, Usman et al. (2002); Kannan & Gerguson (1997); Kannan et al. (1995, 1997, 2000); Linert et al. (2001); Mizuoka & Ikeda (2004); Rajagopal et al. (2002).

Experimental top

Solution of uranyl nitrate hexahydrate (1.20 g) in 2 ml of ethanol was added to a hot solution (10 ml) of dibenzoylmethane (Hdbm, 0.523 g) in 10 ml of ethanol with vigorous stirring. After addition of 1 N NaOH (3 ml), the solution was concentrated by heating, and then cooled to room temperature. Deposited crystals of the title compound were filtered off, washed with ethanol, and dried under the ambient atmosphere.

Structure description top

For literature on the structural chemistry of uranyl(VI) complexes with dibenzoylmethanate and unidentate ligands, see: Alagar et al. (2003, 2004); Fun, Kannan, Chantrapromma et al. (2002); Fun, Kannan, Usman et al. (2002); Kannan & Gerguson (1997); Kannan et al. (1995, 1997, 2000); Linert et al. (2001); Mizuoka & Ikeda (2004); Rajagopal et al. (2002).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (MSC/Rigaku, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIFF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (MSC/Rigaku, 2006).

Figures top

	Fig. 1. : Molecular structure of UO₂(dbm)₂EtOH (I) with displacement elipsoids shown at the 50% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. : Structure of the dimeric aggregate of I [molecules are related by the symmetry operation (i) 1 - x, 1 - y, 1 - z]. Dashed lines indicate intermolecular –OH···O_yl hydrogen bonds between neighboring molecules. Hydrogen atoms except for the OH group are omitted for clarity.

Bis(2-benzoyl-1-phenylethenolato-κ²O,O')(ethanol-κO)dioxidouranium(VI) top

Crystal data top

[U(C₁₅H₁₁O₂)₂O₂(C₂H₆O)]	F(000) = 1472
M_r = 762.57	D_x = 1.797 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 22955 reflections
a = 9.088 (5) Å	θ = 3.0–27.6°
b = 12.141 (7) Å	µ = 5.81 mm⁻¹
c = 25.878 (13) Å	T = 173 K
β = 99.126 (16)°	Platelet, orange
V = 2819 (3) Å³	0.40 × 0.30 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	6442 independent reflections
Radiation source: fine-focus sealed tube	4539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −11→11
Absorption correction: numerical (Higashi, 1999)	k = −15→15
T_min = 0.205, T_max = 0.594	l = −33→33
26257 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0288P)² + 2.9796P] where P = (F_o² + 2F_c²)/3
6442 reflections	(Δ/σ)_max = 0.001
362 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³
0 constraints

Crystal data top

[U(C₁₅H₁₁O₂)₂O₂(C₂H₆O)]	V = 2819 (3) Å³
M_r = 762.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.088 (5) Å	µ = 5.81 mm⁻¹
b = 12.141 (7) Å	T = 173 K
c = 25.878 (13) Å	0.40 × 0.30 × 0.10 mm
β = 99.126 (16)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6442 independent reflections
Absorption correction: numerical (Higashi, 1999)	4539 reflections with I > 2σ(I)
T_min = 0.205, T_max = 0.594	R_int = 0.097
26257 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.01	Δρ_max = 1.05 e Å⁻³
6442 reflections	Δρ_min = −0.69 e Å⁻³
362 parameters

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 > 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) top

	x	y	z	U_iso*/U_eq
U1	0.56596 (2)	0.415650 (18)	0.597530 (8)	0.03064 (7)
O1	0.4826 (4)	0.3391 (4)	0.64300 (17)	0.0415 (10)
O2	0.6473 (4)	0.4912 (4)	0.54993 (16)	0.0403 (10)
O3	0.4712 (4)	0.2914 (3)	0.52999 (16)	0.0396 (10)
O4	0.7334 (4)	0.2763 (3)	0.59376 (15)	0.0382 (10)
O5	0.7648 (4)	0.4744 (4)	0.66069 (17)	0.0419 (11)
O6	0.4991 (5)	0.5764 (4)	0.63790 (18)	0.0491 (12)
O7	0.3209 (4)	0.4808 (3)	0.55377 (15)	0.0372 (10)
H6	0.3287	0.5044	0.5230	0.031*
C1	0.2955 (7)	0.2313 (5)	0.4362 (2)	0.0387 (14)
H1	0.2766	0.3017	0.4498	0.046*
C2	0.1947 (7)	0.1867 (6)	0.3973 (3)	0.0450 (16)
H2	0.1063	0.2260	0.3839	0.054*
C3	0.2210 (7)	0.0843 (6)	0.3772 (2)	0.0469 (16)
H3	0.1506	0.0535	0.3500	0.056*
C4	0.3477 (7)	0.0271 (6)	0.3962 (2)	0.0453 (16)
H4	0.3646	−0.0433	0.3822	0.054*
C5	0.4521 (7)	0.0717 (5)	0.4360 (2)	0.0387 (14)
H5	0.5404	0.0321	0.4491	0.046*
C6	0.4260 (6)	0.1754 (5)	0.4566 (2)	0.0312 (13)
C7	0.5299 (6)	0.2243 (5)	0.5012 (2)	0.0327 (13)
C8	0.6823 (6)	0.1955 (5)	0.5101 (2)	0.0330 (13)
H8	0.7219	0.1563	0.4837	0.040*
C9	0.7770 (6)	0.2221 (5)	0.5562 (2)	0.0322 (13)
C10	0.9351 (6)	0.1858 (5)	0.5657 (2)	0.0319 (13)
C11	1.0087 (7)	0.1396 (5)	0.5280 (3)	0.0390 (15)
H11	0.9558	0.1268	0.4938	0.047*
C12	1.1592 (7)	0.1116 (5)	0.5393 (3)	0.0461 (17)
H12	1.2081	0.0805	0.5130	0.055*
C13	1.2362 (7)	0.1291 (5)	0.5885 (3)	0.0472 (17)
H13	1.3386	0.1099	0.5963	0.057*
C14	1.1658 (7)	0.1747 (6)	0.6271 (3)	0.0483 (17)
H14	1.2199	0.1873	0.6611	0.058*
C15	1.0173 (7)	0.2017 (5)	0.6160 (3)	0.0417 (15)
H15	0.9691	0.2316	0.6429	0.050*
C16	1.0565 (8)	0.4803 (6)	0.7029 (3)	0.0546 (18)
H16	1.0176	0.4199	0.6817	0.066*
C17	1.2082 (8)	0.4842 (8)	0.7233 (3)	0.068 (2)
H17	1.2722	0.4269	0.7152	0.082*
C18	1.2655 (8)	0.5694 (8)	0.7546 (3)	0.061 (2)
H18	1.3684	0.5705	0.7688	0.073*
C19	1.1746 (8)	0.6530 (8)	0.7653 (3)	0.067 (2)
H19	1.2137	0.7121	0.7873	0.080*
C20	1.0220 (7)	0.6511 (7)	0.7435 (3)	0.064 (2)
H20	0.9597	0.7108	0.7499	0.076*
C21	0.9625 (6)	0.5643 (5)	0.7134 (2)	0.0352 (14)
C22	0.8030 (6)	0.5595 (5)	0.6885 (2)	0.0326 (14)
C23	0.7037 (7)	0.6423 (5)	0.6961 (2)	0.0348 (14)
H23	0.7374	0.6988	0.7206	0.042*
C24	0.5560 (6)	0.6478 (5)	0.6700 (2)	0.0313 (13)
C25	0.4577 (6)	0.7408 (5)	0.6784 (2)	0.0309 (12)
C26	0.4787 (7)	0.8051 (5)	0.7236 (2)	0.0416 (15)
H26	0.5600	0.7897	0.7505	0.050*
C27	0.3832 (8)	0.8908 (5)	0.7299 (3)	0.0504 (18)
H27	0.3987	0.9332	0.7611	0.060*
C28	0.2655 (8)	0.9151 (6)	0.6909 (3)	0.0522 (17)
H28	0.2001	0.9742	0.6954	0.063*
C29	0.2423 (7)	0.8526 (6)	0.6448 (3)	0.0452 (16)
H29	0.1625	0.8697	0.6177	0.054*
C30	0.3369 (7)	0.7660 (5)	0.6394 (2)	0.0374 (14)
H30	0.3197	0.7224	0.6085	0.045*
C31	0.1778 (7)	0.4503 (6)	0.5666 (3)	0.054 (2)
H31A	0.1922	0.4165	0.6018	0.065*
H31B	0.1316	0.3944	0.5412	0.065*
C32	0.0755 (8)	0.5455 (7)	0.5659 (4)	0.069 (2)
H32A	−0.0198	0.5207	0.5750	0.083*
H32B	0.0586	0.5782	0.5308	0.083*
H32C	0.1199	0.6006	0.5913	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
U1	0.02771 (11)	0.03283 (12)	0.03087 (11)	0.00087 (12)	0.00310 (8)	−0.00756 (11)
O1	0.032 (2)	0.051 (3)	0.040 (2)	−0.004 (2)	0.002 (2)	−0.006 (2)
O2	0.032 (2)	0.046 (3)	0.042 (2)	−0.002 (2)	0.001 (2)	0.002 (2)
O3	0.034 (2)	0.040 (3)	0.042 (2)	−0.0005 (19)	−0.004 (2)	−0.014 (2)
O4	0.042 (2)	0.039 (3)	0.032 (2)	0.007 (2)	0.001 (2)	−0.0085 (19)
O5	0.030 (2)	0.050 (3)	0.045 (3)	−0.001 (2)	0.002 (2)	−0.018 (2)
O6	0.039 (2)	0.048 (3)	0.058 (3)	0.006 (2)	0.001 (2)	−0.023 (2)
O7	0.034 (2)	0.046 (3)	0.032 (2)	0.006 (2)	0.0067 (19)	−0.0010 (19)
C1	0.039 (3)	0.034 (4)	0.042 (3)	−0.010 (3)	0.004 (3)	−0.005 (3)
C2	0.043 (4)	0.044 (4)	0.047 (4)	−0.004 (3)	0.002 (3)	0.004 (3)
C3	0.044 (3)	0.058 (4)	0.037 (3)	−0.018 (4)	0.000 (3)	−0.006 (4)
C4	0.050 (4)	0.047 (4)	0.036 (3)	−0.010 (3)	−0.001 (3)	−0.008 (3)
C5	0.044 (3)	0.036 (4)	0.034 (3)	−0.002 (3)	0.000 (3)	−0.004 (3)
C6	0.036 (3)	0.031 (3)	0.025 (3)	−0.008 (3)	0.002 (3)	−0.002 (2)
C7	0.034 (3)	0.029 (3)	0.035 (3)	−0.002 (3)	0.005 (3)	−0.002 (3)
C8	0.029 (3)	0.041 (4)	0.028 (3)	0.003 (3)	0.002 (3)	−0.006 (3)
C9	0.033 (3)	0.024 (3)	0.041 (3)	0.000 (2)	0.006 (3)	0.003 (3)
C10	0.034 (3)	0.027 (3)	0.035 (3)	−0.002 (3)	0.010 (3)	0.003 (3)
C11	0.043 (3)	0.034 (4)	0.041 (4)	−0.002 (3)	0.010 (3)	−0.001 (3)
C12	0.034 (3)	0.049 (5)	0.059 (4)	0.006 (3)	0.020 (4)	0.002 (3)
C13	0.037 (3)	0.040 (4)	0.065 (5)	0.005 (3)	0.009 (4)	0.000 (3)
C14	0.040 (4)	0.049 (4)	0.050 (4)	0.007 (3)	−0.013 (3)	−0.003 (3)
C15	0.039 (3)	0.041 (4)	0.042 (4)	0.006 (3)	0.000 (3)	−0.005 (3)
C16	0.045 (4)	0.051 (5)	0.061 (5)	0.002 (4)	−0.013 (4)	0.000 (4)
C17	0.047 (4)	0.074 (6)	0.080 (6)	0.006 (4)	−0.004 (4)	0.005 (5)
C18	0.039 (4)	0.097 (7)	0.045 (4)	−0.018 (5)	0.000 (4)	0.009 (4)
C19	0.043 (4)	0.105 (7)	0.052 (5)	−0.031 (5)	0.008 (4)	−0.022 (5)
C20	0.033 (4)	0.088 (6)	0.071 (6)	−0.015 (4)	0.014 (4)	−0.037 (5)
C21	0.032 (3)	0.047 (4)	0.027 (3)	−0.010 (3)	0.004 (3)	0.000 (3)
C22	0.035 (3)	0.037 (4)	0.029 (3)	−0.005 (3)	0.014 (3)	0.000 (2)
C23	0.040 (3)	0.033 (3)	0.032 (3)	−0.011 (3)	0.008 (3)	−0.007 (3)
C24	0.035 (3)	0.031 (3)	0.031 (3)	−0.006 (3)	0.018 (3)	−0.002 (2)
C25	0.038 (3)	0.027 (3)	0.030 (3)	−0.005 (3)	0.011 (3)	−0.004 (2)
C26	0.049 (4)	0.043 (4)	0.032 (3)	0.003 (3)	0.003 (3)	−0.008 (3)
C27	0.069 (5)	0.040 (4)	0.042 (4)	0.010 (3)	0.010 (4)	−0.014 (3)
C28	0.068 (5)	0.041 (4)	0.048 (4)	0.017 (4)	0.011 (4)	−0.003 (4)
C29	0.044 (4)	0.051 (4)	0.041 (4)	0.005 (3)	0.006 (3)	0.003 (3)
C30	0.045 (3)	0.036 (4)	0.033 (3)	0.002 (3)	0.008 (3)	−0.006 (3)
C31	0.035 (3)	0.068 (5)	0.057 (5)	−0.005 (3)	0.000 (4)	0.006 (4)
C32	0.042 (4)	0.082 (6)	0.084 (6)	0.009 (4)	0.009 (4)	−0.016 (5)

Geometric parameters (Å, º) top

U1—O1	1.762 (4)	C14—C15	1.374 (9)
U1—O2	1.787 (4)	C14—H14	0.9500
U1—O4	2.288 (4)	C15—H15	0.9500
U1—O6	2.339 (4)	C16—C21	1.384 (9)
U1—O5	2.347 (4)	C16—C17	1.396 (10)
U1—O3	2.365 (4)	C16—H16	0.9500
U1—O7	2.464 (4)	C17—C18	1.365 (11)
O3—C7	1.278 (6)	C17—H17	0.9500
O4—C9	1.288 (6)	C18—C19	1.365 (11)
O5—C22	1.276 (7)	C18—H18	0.9500
O6—C24	1.253 (7)	C19—C20	1.411 (10)
O7—C31	1.440 (7)	C19—H19	0.9500
O7—H6	0.8596	C20—C21	1.370 (9)
C1—C2	1.362 (9)	C20—H20	0.9500
C1—C6	1.395 (8)	C21—C22	1.492 (8)
C1—H1	0.9500	C22—C23	1.385 (8)
C2—C3	1.383 (9)	C23—C24	1.405 (8)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.368 (9)	C24—C25	1.477 (8)
C3—H3	0.9500	C25—C26	1.395 (8)
C4—C5	1.395 (9)	C25—C30	1.403 (8)
C4—H4	0.9500	C26—C27	1.381 (8)
C5—C6	1.403 (8)	C26—H26	0.9500
C5—H5	0.9500	C27—C28	1.380 (10)
C6—C7	1.492 (8)	C27—H27	0.9500
C7—C8	1.411 (8)	C28—C29	1.401 (9)
C8—C9	1.392 (8)	C28—H28	0.9500
C8—H8	0.9500	C29—C30	1.380 (8)
C9—C10	1.486 (8)	C29—H29	0.9500
C10—C11	1.386 (8)	C30—H30	0.9500
C10—C15	1.408 (9)	C31—C32	1.481 (10)
C11—C12	1.394 (9)	C31—H31A	0.9900
C11—H11	0.9500	C31—H31B	0.9900
C12—C13	1.368 (10)	C32—H32A	0.9800
C12—H12	0.9500	C32—H32B	0.9800
C13—C14	1.383 (9)	C32—H32C	0.9800
C13—H13	0.9500

O1—U1—O2	178.36 (19)	C12—C13—H13	119.8
O1—U1—O4	89.86 (18)	C14—C13—H13	119.8
O2—U1—O4	90.00 (17)	C15—C14—C13	119.8 (7)
O1—U1—O6	88.42 (19)	C15—C14—H14	120.1
O2—U1—O6	92.55 (19)	C13—C14—H14	120.1
O4—U1—O6	149.05 (15)	C14—C15—C10	121.2 (6)
O1—U1—O5	93.46 (18)	C14—C15—H15	119.4
O2—U1—O5	88.12 (18)	C10—C15—H15	119.4
O4—U1—O5	79.09 (15)	C21—C16—C17	120.3 (7)
O6—U1—O5	70.19 (15)	C21—C16—H16	119.9
O1—U1—O3	90.71 (18)	C17—C16—H16	119.9
O2—U1—O3	87.70 (18)	C18—C17—C16	120.6 (8)
O4—U1—O3	70.35 (14)	C18—C17—H17	119.7
O6—U1—O3	140.55 (15)	C16—C17—H17	119.7
O5—U1—O3	149.14 (14)	C17—C18—C19	119.9 (7)
O1—U1—O7	91.33 (17)	C17—C18—H18	120.0
O2—U1—O7	87.75 (16)	C19—C18—H18	120.0
O4—U1—O7	140.97 (14)	C18—C19—C20	119.6 (7)
O6—U1—O7	69.97 (15)	C18—C19—H19	120.2
O5—U1—O7	139.70 (14)	C20—C19—H19	120.2
O3—U1—O7	70.62 (14)	C21—C20—C19	120.9 (7)
C7—O3—U1	134.5 (4)	C21—C20—H20	119.5
C9—O4—U1	134.1 (4)	C19—C20—H20	119.5
C22—O5—U1	138.5 (4)	C20—C21—C16	118.6 (6)
C24—O6—U1	139.8 (4)	C20—C21—C22	123.0 (6)
C31—O7—U1	126.5 (4)	C16—C21—C22	118.3 (6)
C31—O7—H6	120.6	O5—C22—C23	122.9 (6)
U1—O7—H6	109.3	O5—C22—C21	115.7 (5)
C2—C1—C6	121.2 (6)	C23—C22—C21	121.4 (5)
C2—C1—H1	119.4	C22—C23—C24	124.0 (6)
C6—C1—H1	119.4	C22—C23—H23	118.0
C1—C2—C3	119.9 (7)	C24—C23—H23	118.0
C1—C2—H2	120.0	O6—C24—C23	123.3 (5)
C3—C2—H2	120.0	O6—C24—C25	115.5 (5)
C4—C3—C2	120.6 (6)	C23—C24—C25	121.2 (5)
C4—C3—H3	119.7	C26—C25—C30	117.9 (6)
C2—C3—H3	119.7	C26—C25—C24	123.1 (6)
C3—C4—C5	120.2 (6)	C30—C25—C24	118.9 (5)
C3—C4—H4	119.9	C27—C26—C25	121.1 (6)
C5—C4—H4	119.9	C27—C26—H26	119.4
C4—C5—C6	119.5 (6)	C25—C26—H26	119.4
C4—C5—H5	120.2	C28—C27—C26	120.2 (6)
C6—C5—H5	120.2	C28—C27—H27	119.9
C1—C6—C5	118.5 (6)	C26—C27—H27	119.9
C1—C6—C7	119.7 (5)	C27—C28—C29	120.0 (6)
C5—C6—C7	121.7 (5)	C27—C28—H28	120.0
O3—C7—C8	123.5 (5)	C29—C28—H28	120.0
O3—C7—C6	115.6 (5)	C30—C29—C28	119.3 (6)
C8—C7—C6	120.9 (5)	C30—C29—H29	120.4
C9—C8—C7	122.7 (5)	C28—C29—H29	120.4
C9—C8—H8	118.6	C29—C30—C25	121.5 (6)
C7—C8—H8	118.6	C29—C30—H30	119.3
O4—C9—C8	122.9 (5)	C25—C30—H30	119.3
O4—C9—C10	115.6 (5)	O7—C31—C32	112.6 (6)
C8—C9—C10	121.6 (5)	O7—C31—H31A	109.1
C11—C10—C15	117.6 (6)	C32—C31—H31A	109.1
C11—C10—C9	124.4 (6)	O7—C31—H31B	109.1
C15—C10—C9	118.0 (5)	C32—C31—H31B	109.1
C10—C11—C12	121.1 (7)	H31A—C31—H31B	107.8
C10—C11—H11	119.5	C31—C32—H32A	109.5
C12—C11—H11	119.5	C31—C32—H32B	109.5
C13—C12—C11	119.9 (6)	H32A—C32—H32B	109.5
C13—C12—H12	120.1	C31—C32—H32C	109.5
C11—C12—H12	120.1	H32A—C32—H32C	109.5
C12—C13—C14	120.4 (6)	H32B—C32—H32C	109.5

O1—U1—O3—C7	−115.6 (5)	C7—C8—C9—O4	−1.0 (9)
O2—U1—O3—C7	64.8 (5)	C7—C8—C9—C10	176.9 (5)
O4—U1—O3—C7	−26.0 (5)	O4—C9—C10—C11	−171.1 (5)
O6—U1—O3—C7	156.0 (5)	C8—C9—C10—C11	10.8 (9)
O5—U1—O3—C7	−17.7 (7)	O4—C9—C10—C15	7.3 (8)
O7—U1—O3—C7	153.2 (6)	C8—C9—C10—C15	−170.7 (6)
O1—U1—O4—C9	129.1 (5)	C15—C10—C11—C12	−1.0 (9)
O2—U1—O4—C9	−49.3 (5)	C9—C10—C11—C12	177.4 (6)
O6—U1—O4—C9	−144.2 (5)	C10—C11—C12—C13	0.4 (10)
O5—U1—O4—C9	−137.3 (5)	C11—C12—C13—C14	−0.2 (10)
O3—U1—O4—C9	38.3 (5)	C12—C13—C14—C15	0.6 (11)
O7—U1—O4—C9	37.2 (6)	C13—C14—C15—C10	−1.2 (10)
O1—U1—O5—C22	−99.8 (6)	C11—C10—C15—C14	1.4 (9)
O2—U1—O5—C22	80.7 (6)	C9—C10—C15—C14	−177.1 (6)
O4—U1—O5—C22	171.0 (6)	C21—C16—C17—C18	1.2 (12)
O6—U1—O5—C22	−12.7 (5)	C16—C17—C18—C19	−1.3 (12)
O3—U1—O5—C22	163.0 (5)	C17—C18—C19—C20	−0.6 (12)
O7—U1—O5—C22	−3.6 (7)	C18—C19—C20—C21	2.6 (13)
O1—U1—O6—C24	100.7 (7)	C19—C20—C21—C16	−2.7 (11)
O2—U1—O6—C24	−80.7 (7)	C19—C20—C21—C22	−178.5 (7)
O4—U1—O6—C24	13.6 (8)	C17—C16—C21—C20	0.8 (11)
O5—U1—O6—C24	6.4 (6)	C17—C16—C21—C22	176.8 (6)
O3—U1—O6—C24	−170.1 (6)	U1—O5—C22—C23	16.0 (9)
O7—U1—O6—C24	−167.3 (7)	U1—O5—C22—C21	−164.9 (4)
O1—U1—O7—C31	−2.7 (5)	C20—C21—C22—O5	178.6 (6)
O2—U1—O7—C31	175.9 (5)	C16—C21—C22—O5	2.7 (8)
O4—U1—O7—C31	88.7 (5)	C20—C21—C22—C23	−2.3 (9)
O6—U1—O7—C31	−90.6 (5)	C16—C21—C22—C23	−178.2 (6)
O5—U1—O7—C31	−99.7 (5)	O5—C22—C23—C24	−7.2 (9)
O3—U1—O7—C31	87.6 (5)	C21—C22—C23—C24	173.8 (5)
C6—C1—C2—C3	−0.1 (9)	U1—O6—C24—C23	−3.9 (10)
C1—C2—C3—C4	0.1 (10)	U1—O6—C24—C25	175.3 (4)
C2—C3—C4—C5	−0.2 (10)	C22—C23—C24—O6	1.6 (9)
C3—C4—C5—C6	0.3 (9)	C22—C23—C24—C25	−177.5 (5)
C2—C1—C6—C5	0.2 (9)	O6—C24—C25—C26	156.8 (6)
C2—C1—C6—C7	−176.9 (5)	C23—C24—C25—C26	−24.0 (8)
C4—C5—C6—C1	−0.3 (8)	O6—C24—C25—C30	−22.9 (8)
C4—C5—C6—C7	176.7 (5)	C23—C24—C25—C30	156.3 (5)
U1—O3—C7—C8	10.9 (9)	C30—C25—C26—C27	0.2 (9)
U1—O3—C7—C6	−169.8 (4)	C24—C25—C26—C27	−179.5 (6)
C1—C6—C7—O3	24.7 (8)	C25—C26—C27—C28	−0.7 (10)
C5—C6—C7—O3	−152.3 (5)	C26—C27—C28—C29	0.1 (11)
C1—C6—C7—C8	−156.1 (6)	C27—C28—C29—C30	1.1 (10)
C5—C6—C7—C8	26.9 (8)	C28—C29—C30—C25	−1.6 (10)
O3—C7—C8—C9	11.7 (10)	C26—C25—C30—C29	1.0 (9)
C6—C7—C8—C9	−167.5 (5)	C24—C25—C30—C29	−179.3 (5)
U1—O4—C9—C8	−34.8 (8)	U1—O7—C31—C32	137.6 (5)
U1—O4—C9—C10	147.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H6···O2ⁱ	0.86	1.94	2.765 (5)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[U(C₁₅H₁₁O₂)₂O₂(C₂H₆O)]
M_r	762.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.088 (5), 12.141 (7), 25.878 (13)
β (°)	99.126 (16)
V (Å³)	2819 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.81
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (Higashi, 1999)
T_min, T_max	0.205, 0.594
No. of measured, independent and observed [I > 2σ(I)] reflections	26257, 6442, 4539
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.083, 1.01
No. of reflections	6442
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.69

Computer programs: PROCESS-AUTO (Rigaku, 2006), PROCESS-AUTO (Rigaku, 2006), CrystalStructure (MSC/Rigaku, 2006), SIR97 (Altomare et al., 1999) and DIRDIFF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Farrugia, 1997).

Selected bond lengths (Å) top

U1—O1	1.762 (4)	U1—O5	2.347 (4)
U1—O2	1.787 (4)	U1—O3	2.365 (4)
U1—O4	2.288 (4)	U1—O7	2.464 (4)
U1—O6	2.339 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H6···O2ⁱ	0.86	1.94	2.765 (5)	162

Symmetry code: (i) −x+1, −y+1, −z+1.

References

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Volume 64| Part 1| January 2008| Pages m219-m220

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