Bis­(4-benzoyl-3-methyl-1-phenyl-4,5-di­hydro-1H-pyrazol-5-olato-κ2O,O′)(methanol-κO)dioxidouranium(VI) methanol monosolvate

Dehbi, O.; Keraghel, S.; Bouacida, S.; Benghanem, F.; Ourari, A.

doi:10.1107/S1600536812011075

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages m457-m458

doi:10.1107/S1600536812011075

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Bis(4-benzoyl-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-olato-κ²O,O′)(methanol-κO)dioxidouranium(VI) methanol monosolvate

Ouarda Dehbi,^a Saida Keraghel,^a Sofiane Bouacida,^b ^* Fatiha Benghanem ^a and Ali Ourari ^a

^aLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif 19000, Algeria, and ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 1 March 2012; accepted 13 March 2012; online 21 March 2012)

In the title compound, [U(C₁₇H₁₃N₂O₂)₂O₂(CH₃OH)]·CH₃OH, the U^VI ion is coordinated by seven O atoms in a distorted pentagonal–bipyramidal geometry with two 3-methyl-1-phenyl-4-benzoyl-4,5-dihydro-1H-pyrazol-5-olate groups with two O atoms in a bidentate chelating coordination mode and by three O atoms, one of which is from a methanol ligand. The crystal packing can be described by alternating layers of complex molecules along the a axis. The structure is stabilized by O—H⋯N and O—H⋯O hydrogen bonding and van der Waals interactions.

Related literature

For the synthesis and applications of similar compounds: Okafor (1981 ); Caruso et al. (2000 ); Li et al. (1997 ); Zhou et al. (1999 ).

Experimental

Crystal data

[U(C₁₇H₁₃N₂O₂)₂O₂(CH₄O)]·CH₄O
M_r = 888.7
Triclinic, $[P \overline 1]$
a = 10.3353 (18) Å
b = 12.988 (2) Å
c = 13.955 (3) Å
α = 69.938 (3)°
β = 81.728 (2)°
γ = 70.722 (3)°
V = 1659.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 4.95 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.242, T_max = 0.318
20251 measured reflections
10125 independent reflections
8127 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.096
S = 1.00
10125 reflections
450 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.45 e Å⁻³
Δρ_min = −3.52 e Å⁻³

Table 1
Selected bond lengths (Å)

O1—U1	2.334 (3)
O2—U1	2.388 (3)
O3—U1	2.391 (3)
O4—U1	2.388 (3)
O5—U1	1.768 (3)
O6—U1	1.761 (3)
O7—U1	2.456 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7O⋯O36Sⁱ	0.81 (2)	1.84 (5)	2.633 (6)	168 (5)
O36S—H36S⋯N2ⁱⁱ	0.82	2.12	2.878 (6)	153
C6—H6⋯O3	0.93	2.33	2.909 (7)	120
C19—H19⋯O1	0.93	2.54	2.989 (7)	110
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812011075/bq2342sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011075/bq2342Isup2.hkl

checkCIF report

Comment top

The ligands derived fromβ-diketone compounds such as those of 3-methyl-1-phenyl-4-benzoylpyrazol-5-one (H1MPBP) have been found to have good extractive ability for heavy metals traces and interesting biological activities (Okafor et al., 1981). Their metal complexes M^II–(MPBP)₂ of copper(II) and zinc(II) are well known in the literature for their diverse therapeutic applications as anticarcinogenic, anti-inflammatory and analgesic activities (Caruso et al., 2000; Li et al., 1997; Zhou et al., 1999). Thus, we report here the synthesis of title compound and its crystal structure. The asymetric unit of structure of (I), and the atomic numbering used, is illustrated in Fig. 1.

The U^VI ion is coordinated in a irregular octahedral geometry by two (3-Methyl-1-phenyl-4-benzoylpyrazol-5-one)groups with two O atoms in bidentate chelating coordination and three O atoms, when one O atom is linked to methanol moiety. One molecule of methanol is cocrystalized with the title complexe. The bond lengths for co-ordination U(V) sphere is ranging from 1.760 (3) to 2.391 (3)Å for Cu-O distances (Table 2). The crystal packing in the title structure can be described by alterning layers of complexe along the a axis (Fig. 2). It's stabilized by intermolecular O-H···N, O-H···O hydrogen bonding (Table 1, Fig. 2) and a Van Der Waals interactions. These interactions link the molecules within the layers and also link the layers together and reinforcing the cohesion of the structure.

Related literature top

For the synthesis and applications of similar compounds: Okafor (1981); Caruso et al. (2000); Li et al. (1997); Zhou et al. (1999).

Experimental top

106 mg (0.25 mmol) of dioxouranyl(II) acetate dihydrate (UO₂(OAc)₂,2H₂O) were dissolved in 15 ml of methanol. This solution was drop wisely added, under stirring, to a methanolic solution (10 ml) containing 139 mg of 3-methyl-1-phenyl-4-benzoylpyrazol-5-one (0.5 mmol, H1MPBP). This mixture was refluxed during one night after which is abandoned for several weeks until the formation of suitable crystals. These crystals, recovered by filtration, were then washed several times with methanol and dried to yield 132 mg (60%) of the title compound.

Structure description top

For the synthesis and applications of similar compounds: Okafor (1981); Caruso et al. (2000); Li et al. (1997); Zhou et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Altering layers of (I) viewed via b axis showing hydrogen bond interactions(O—H···N), in blue, as dashed lines.

Bis(4-benzoyl-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-olato- κ²O,O')(methanol-κO)dioxidouranium(VI) methanol monosolvate top

Crystal data top

[U(C₁₇H₁₃N₂O₂)₂O₂(CH₄O)]·CH₄O	Z = 2
M_r = 888.7	F(000) = 868
Triclinic, P1	D_x = 1.778 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3353 (18) Å	Cell parameters from 5297 reflections
b = 12.988 (2) Å	θ = 2.4–26.8°
c = 13.955 (3) Å	µ = 4.95 mm⁻¹
α = 69.938 (3)°	T = 173 K
β = 81.728 (2)°	Block, orange
γ = 70.722 (3)°	0.40 × 0.40 × 0.30 mm
V = 1659.9 (5) Å³

Data collection top

Bruker APEXII diffractometer	10125 independent reflections
Radiation source: fine-focus sealed tube	8127 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
phi and ω scans	θ_max = 30.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −14→14
T_min = 0.242, T_max = 0.318	k = −18→18
20251 measured reflections	l = −20→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0322P)²] where P = (F_o² + 2F_c²)/3
10125 reflections	(Δ/σ)_max = 0.002
450 parameters	Δρ_max = 2.45 e Å⁻³
1 restraint	Δρ_min = −3.52 e Å⁻³

Crystal data top

[U(C₁₇H₁₃N₂O₂)₂O₂(CH₄O)]·CH₄O	γ = 70.722 (3)°
M_r = 888.7	V = 1659.9 (5) Å³
Triclinic, P1	Z = 2
a = 10.3353 (18) Å	Mo Kα radiation
b = 12.988 (2) Å	µ = 4.95 mm⁻¹
c = 13.955 (3) Å	T = 173 K
α = 69.938 (3)°	0.40 × 0.40 × 0.30 mm
β = 81.728 (2)°

Data collection top

Bruker APEXII diffractometer	10125 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	8127 reflections with I > 2σ(I)
T_min = 0.242, T_max = 0.318	R_int = 0.064
20251 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 2.45 e Å⁻³
10125 reflections	Δρ_min = −3.52 e Å⁻³
450 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.3016 (5)	0.0112 (4)	1.0673 (3)	0.0181 (9)
C2	0.4041 (5)	−0.0758 (5)	1.1291 (4)	0.0269 (11)
H2	0.4829	−0.0614	1.1386	0.032*
C3	0.3878 (5)	−0.1836 (4)	1.1761 (4)	0.0247 (11)
H3	0.4567	−0.2416	1.2166	0.03*
C4	0.2714 (5)	−0.2063 (4)	1.1640 (4)	0.0252 (11)
H4	0.2608	−0.2787	1.1971	0.03*
C5	0.1707 (5)	−0.1207 (4)	1.1023 (4)	0.0254 (11)
H5	0.0926	−0.1363	1.093	0.03*
C6	0.1834 (5)	−0.0119 (4)	1.0541 (4)	0.0232 (10)
H6	0.1142	0.0453	1.0133	0.028*
C7	0.2455 (5)	0.2101 (4)	0.9434 (3)	0.0177 (9)
C8	0.2818 (5)	0.3085 (4)	0.9380 (4)	0.0194 (10)
C9	0.3811 (5)	0.2681 (4)	1.0143 (4)	0.0207 (10)
C10	0.4678 (6)	0.3295 (5)	1.0350 (4)	0.0297 (12)
H10A	0.5279	0.2783	1.0894	0.045*
H10B	0.41	0.3946	1.0542	0.045*
H10C	0.5213	0.355	0.9746	0.045*
C11	0.2170 (5)	0.4193 (4)	0.8721 (4)	0.0199 (10)
C12	0.2119 (5)	0.5265 (4)	0.8918 (4)	0.0210 (10)
C13	0.1680 (6)	0.5421 (5)	0.9852 (4)	0.0283 (12)
H13	0.1491	0.4821	1.039	0.034*
C14	0.1516 (6)	0.6457 (5)	1.0000 (4)	0.0316 (12)
H14	0.1197	0.6564	1.0627	0.038*
C15	0.1831 (5)	0.7329 (5)	0.9206 (5)	0.0319 (13)
H15	0.1741	0.8023	0.9304	0.038*
C16	0.2276 (5)	0.7186 (4)	0.8270 (4)	0.0289 (12)
H16	0.2487	0.7781	0.7741	0.035*
C17	0.2413 (5)	0.6159 (4)	0.8112 (4)	0.0258 (11)
H17	0.2697	0.6067	0.7475	0.031*
C18	0.2910 (5)	0.6501 (4)	0.4807 (4)	0.0220 (10)
C19	0.1797 (5)	0.7099 (4)	0.5284 (4)	0.0277 (11)
H19	0.0975	0.692	0.5404	0.033*
C20	0.1938 (6)	0.7969 (5)	0.5578 (5)	0.0343 (13)
H20	0.1209	0.8373	0.5911	0.041*
C21	0.3159 (6)	0.8245 (5)	0.5380 (5)	0.0343 (13)
H21	0.3244	0.883	0.5581	0.041*
C22	0.4226 (5)	0.7662 (5)	0.4893 (4)	0.0300 (12)
H22	0.5036	0.7858	0.4757	0.036*
C23	0.4125 (5)	0.6786 (5)	0.4600 (4)	0.0299 (12)
H23	0.4862	0.6388	0.4268	0.036*
C24	0.2139 (5)	0.4804 (4)	0.4970 (4)	0.0207 (10)
C25	0.2349 (5)	0.4098 (4)	0.4349 (4)	0.0216 (10)
C26	0.3228 (5)	0.4549 (4)	0.3511 (4)	0.0232 (10)
C27	0.3865 (6)	0.4137 (5)	0.2632 (4)	0.0369 (14)
H27A	0.4586	0.447	0.2322	0.055*
H27B	0.3182	0.436	0.2139	0.055*
H27C	0.4237	0.3314	0.2867	0.055*
C28	0.1815 (5)	0.3184 (4)	0.4603 (4)	0.0233 (10)
C29	0.1708 (5)	0.2638 (4)	0.3842 (4)	0.0224 (10)
C30	0.2010 (5)	0.1454 (4)	0.4139 (4)	0.0274 (11)
H30	0.2326	0.101	0.479	0.033*
C31	0.1844 (6)	0.0924 (5)	0.3468 (4)	0.0320 (12)
H31	0.2052	0.0128	0.3669	0.038*
C32	0.1375 (5)	0.1580 (5)	0.2513 (4)	0.0276 (11)
H32	0.1279	0.1228	0.2061	0.033*
C33	0.1043 (5)	0.2758 (5)	0.2219 (4)	0.0276 (11)
H33	0.0704	0.3197	0.1574	0.033*
C34	0.1209 (5)	0.3296 (4)	0.2878 (4)	0.0261 (11)
H34	0.0988	0.4093	0.2674	0.031*
C35	0.0585 (6)	0.0644 (5)	0.7008 (4)	0.0328 (13)
H35A	−0.0238	0.1242	0.6743	0.049*
H35B	0.035	0.0017	0.7528	0.049*
H35C	0.1107	0.0377	0.6467	0.049*
C36S	0.4590 (7)	0.9616 (7)	0.7067 (5)	0.0525 (18)
H36A	0.5134	1.0098	0.7042	0.079*
H36B	0.4022	0.9956	0.6484	0.079*
H36C	0.5183	0.8871	0.7063	0.079*
N1	0.3146 (4)	0.1229 (3)	1.0221 (3)	0.0199 (8)
N2	0.4026 (4)	0.1577 (3)	1.0642 (3)	0.0206 (8)
N3	0.2801 (4)	0.5596 (4)	0.4498 (3)	0.0246 (9)
N4	0.3513 (4)	0.5416 (4)	0.3602 (3)	0.0263 (9)
O1	0.1436 (3)	0.4773 (3)	0.5828 (3)	0.0221 (7)
O2	0.1534 (4)	0.4329 (3)	0.7957 (3)	0.0257 (8)
O3	0.1624 (3)	0.2027 (3)	0.8890 (2)	0.0225 (7)
O4	0.1342 (3)	0.2794 (3)	0.5502 (3)	0.0242 (8)
O5	0.3227 (3)	0.2567 (3)	0.6995 (3)	0.0232 (7)
O6	−0.0384 (3)	0.3501 (3)	0.7243 (3)	0.0223 (7)
O7	0.1379 (4)	0.1080 (3)	0.7434 (3)	0.0253 (8)
H7O	0.207 (4)	0.058 (4)	0.768 (4)	0.038*
O36S	0.3752 (4)	0.9501 (3)	0.7970 (3)	0.0358 (9)
H36S	0.4216	0.9349	0.8458	0.054*
U1	0.141702 (17)	0.305351 (14)	0.710418 (13)	0.01446 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.021 (2)	0.019 (2)	0.014 (2)	−0.0062 (18)	0.0028 (18)	−0.0060 (18)
C2	0.024 (2)	0.032 (3)	0.028 (3)	−0.011 (2)	−0.006 (2)	−0.008 (2)
C3	0.018 (2)	0.019 (2)	0.029 (3)	0.0030 (19)	−0.006 (2)	−0.004 (2)
C4	0.029 (3)	0.018 (2)	0.028 (3)	−0.009 (2)	0.001 (2)	−0.006 (2)
C5	0.028 (3)	0.027 (3)	0.028 (3)	−0.012 (2)	−0.007 (2)	−0.011 (2)
C6	0.021 (2)	0.024 (2)	0.023 (3)	−0.006 (2)	−0.0052 (19)	−0.004 (2)
C7	0.021 (2)	0.023 (2)	0.011 (2)	−0.0065 (19)	−0.0016 (17)	−0.0072 (19)
C8	0.020 (2)	0.018 (2)	0.020 (2)	−0.0045 (18)	−0.0037 (18)	−0.0059 (19)
C9	0.022 (2)	0.022 (2)	0.019 (2)	−0.0074 (19)	−0.0028 (19)	−0.007 (2)
C10	0.037 (3)	0.028 (3)	0.032 (3)	−0.017 (2)	−0.011 (2)	−0.007 (2)
C11	0.022 (2)	0.018 (2)	0.021 (2)	−0.0060 (19)	−0.0009 (19)	−0.0061 (19)
C12	0.019 (2)	0.021 (2)	0.023 (3)	−0.0024 (19)	−0.0031 (19)	−0.010 (2)
C13	0.037 (3)	0.025 (3)	0.026 (3)	−0.014 (2)	−0.001 (2)	−0.007 (2)
C14	0.038 (3)	0.038 (3)	0.027 (3)	−0.013 (3)	0.003 (2)	−0.021 (3)
C15	0.031 (3)	0.025 (3)	0.047 (4)	−0.007 (2)	−0.007 (3)	−0.020 (3)
C16	0.032 (3)	0.021 (2)	0.035 (3)	−0.013 (2)	−0.003 (2)	−0.005 (2)
C17	0.027 (3)	0.022 (2)	0.027 (3)	−0.007 (2)	−0.004 (2)	−0.006 (2)
C18	0.020 (2)	0.016 (2)	0.027 (3)	−0.0031 (18)	−0.0045 (19)	−0.002 (2)
C19	0.027 (3)	0.025 (3)	0.032 (3)	−0.012 (2)	0.003 (2)	−0.007 (2)
C20	0.033 (3)	0.026 (3)	0.045 (4)	−0.009 (2)	0.007 (3)	−0.015 (3)
C21	0.043 (3)	0.020 (3)	0.042 (4)	−0.013 (2)	−0.013 (3)	−0.005 (2)
C22	0.022 (2)	0.029 (3)	0.039 (3)	−0.011 (2)	−0.005 (2)	−0.007 (2)
C23	0.023 (2)	0.027 (3)	0.041 (3)	−0.010 (2)	−0.002 (2)	−0.010 (2)
C24	0.022 (2)	0.014 (2)	0.021 (2)	−0.0067 (18)	−0.0126 (19)	0.0060 (19)
C25	0.017 (2)	0.026 (2)	0.019 (2)	−0.0004 (19)	−0.0069 (18)	−0.007 (2)
C26	0.018 (2)	0.027 (3)	0.022 (3)	−0.007 (2)	−0.0014 (19)	−0.004 (2)
C27	0.037 (3)	0.048 (4)	0.031 (3)	−0.019 (3)	0.006 (2)	−0.015 (3)
C28	0.022 (2)	0.020 (2)	0.020 (3)	−0.0007 (19)	−0.0089 (19)	0.001 (2)
C29	0.023 (2)	0.024 (2)	0.020 (3)	−0.007 (2)	−0.0035 (19)	−0.006 (2)
C30	0.035 (3)	0.023 (3)	0.023 (3)	−0.007 (2)	−0.005 (2)	−0.006 (2)
C31	0.039 (3)	0.023 (3)	0.035 (3)	−0.009 (2)	0.000 (2)	−0.011 (2)
C32	0.023 (2)	0.040 (3)	0.030 (3)	−0.014 (2)	0.004 (2)	−0.020 (3)
C33	0.024 (2)	0.041 (3)	0.019 (3)	−0.013 (2)	−0.004 (2)	−0.007 (2)
C34	0.023 (2)	0.023 (2)	0.029 (3)	−0.006 (2)	−0.003 (2)	−0.003 (2)
C35	0.037 (3)	0.035 (3)	0.036 (3)	−0.019 (3)	−0.002 (2)	−0.015 (3)
C36S	0.039 (4)	0.065 (5)	0.058 (5)	0.001 (3)	−0.015 (3)	−0.036 (4)
N1	0.0207 (19)	0.0183 (19)	0.021 (2)	−0.0052 (16)	−0.0050 (16)	−0.0057 (17)
N2	0.0175 (18)	0.022 (2)	0.023 (2)	−0.0059 (16)	−0.0029 (16)	−0.0081 (18)
N3	0.022 (2)	0.028 (2)	0.023 (2)	−0.0094 (18)	0.0007 (17)	−0.0063 (19)
N4	0.021 (2)	0.030 (2)	0.026 (2)	−0.0088 (18)	0.0007 (17)	−0.0058 (19)
O1	0.0249 (17)	0.0203 (17)	0.0211 (18)	−0.0100 (14)	0.0050 (14)	−0.0061 (14)
O2	0.035 (2)	0.0194 (17)	0.0234 (19)	−0.0055 (15)	−0.0116 (15)	−0.0062 (15)
O3	0.0279 (18)	0.0166 (16)	0.0206 (18)	−0.0054 (14)	−0.0072 (14)	−0.0019 (14)
O4	0.0287 (18)	0.0280 (19)	0.0178 (18)	−0.0139 (16)	−0.0002 (14)	−0.0047 (15)
O5	0.0158 (15)	0.0296 (19)	0.0270 (19)	−0.0092 (14)	−0.0029 (14)	−0.0091 (16)
O6	0.0168 (15)	0.0244 (18)	0.0248 (19)	−0.0058 (14)	−0.0041 (13)	−0.0057 (15)
O7	0.0279 (19)	0.0160 (17)	0.032 (2)	−0.0026 (14)	−0.0136 (16)	−0.0064 (16)
O36S	0.032 (2)	0.030 (2)	0.045 (3)	−0.0058 (17)	−0.0157 (18)	−0.009 (2)
U1	0.01361 (8)	0.01473 (8)	0.01518 (9)	−0.00454 (6)	−0.00239 (6)	−0.00391 (6)

Geometric parameters (Å, º) top

C1—C2	1.395 (7)	C22—H22	0.93
C1—C6	1.400 (6)	C23—H23	0.93
C1—N1	1.413 (6)	C24—O1	1.304 (6)
C2—C3	1.383 (7)	C24—N3	1.353 (6)
C2—H2	0.93	C24—C25	1.413 (7)
C3—C4	1.375 (7)	C25—C28	1.388 (7)
C3—H3	0.93	C25—C26	1.454 (7)
C4—C5	1.378 (7)	C26—N4	1.302 (7)
C4—H4	0.93	C26—C27	1.486 (7)
C5—C6	1.383 (7)	C27—H27A	0.96
C5—H5	0.93	C27—H27B	0.96
C6—H6	0.93	C27—H27C	0.96
C7—O3	1.271 (5)	C28—O4	1.273 (6)
C7—N1	1.355 (6)	C28—C29	1.498 (7)
C7—C8	1.422 (6)	C29—C30	1.384 (7)
C8—C11	1.414 (6)	C29—C34	1.388 (7)
C8—C9	1.427 (6)	C30—C31	1.396 (8)
C9—N2	1.319 (6)	C30—H30	0.93
C9—C10	1.492 (7)	C31—C32	1.368 (7)
C10—H10A	0.96	C31—H31	0.93
C10—H10B	0.96	C32—C33	1.374 (8)
C10—H10C	0.96	C32—H32	0.93
C11—O2	1.262 (6)	C33—C34	1.389 (7)
C11—C12	1.493 (7)	C33—H33	0.93
C12—C13	1.377 (7)	C34—H34	0.93
C12—C17	1.394 (7)	C35—O7	1.424 (6)
C13—C14	1.383 (7)	C35—H35A	0.96
C13—H13	0.93	C35—H35B	0.96
C14—C15	1.376 (8)	C35—H35C	0.96
C14—H14	0.93	C36S—O36S	1.415 (8)
C15—C16	1.375 (8)	C36S—H36A	0.96
C15—H15	0.93	C36S—H36B	0.96
C16—C17	1.383 (7)	C36S—H36C	0.96
C16—H16	0.93	N1—N2	1.409 (5)
C17—H17	0.93	N3—N4	1.408 (6)
C18—C19	1.383 (7)	O1—U1	2.334 (3)
C18—C23	1.389 (7)	O2—U1	2.388 (3)
C18—N3	1.426 (6)	O3—U1	2.391 (3)
C19—C20	1.382 (8)	O4—U1	2.388 (3)
C19—H19	0.93	O5—U1	1.768 (3)
C20—C21	1.388 (7)	O6—U1	1.761 (3)
C20—H20	0.93	O7—U1	2.456 (3)
C21—C22	1.355 (8)	O7—H7O	0.811 (19)
C21—H21	0.93	O36S—H36S	0.82
C22—C23	1.371 (7)

C2—C1—C6	119.4 (4)	N4—C26—C27	118.0 (4)
C2—C1—N1	120.1 (4)	C25—C26—C27	129.8 (5)
C6—C1—N1	120.4 (4)	C26—C27—H27A	109.5
C3—C2—C1	119.6 (5)	C26—C27—H27B	109.5
C3—C2—H2	120.2	H27A—C27—H27B	109.5
C1—C2—H2	120.2	C26—C27—H27C	109.5
C4—C3—C2	121.1 (5)	H27A—C27—H27C	109.5
C4—C3—H3	119.4	H27B—C27—H27C	109.5
C2—C3—H3	119.4	O4—C28—C25	120.7 (5)
C3—C4—C5	119.2 (5)	O4—C28—C29	116.6 (4)
C3—C4—H4	120.4	C25—C28—C29	122.7 (4)
C5—C4—H4	120.4	C30—C29—C34	119.4 (5)
C4—C5—C6	121.2 (5)	C30—C29—C28	118.9 (4)
C4—C5—H5	119.4	C34—C29—C28	121.5 (5)
C6—C5—H5	119.4	C29—C30—C31	120.3 (5)
C5—C6—C1	119.4 (4)	C29—C30—H30	119.8
C5—C6—H6	120.3	C31—C30—H30	119.8
C1—C6—H6	120.3	C32—C31—C30	119.7 (5)
O3—C7—N1	125.3 (4)	C32—C31—H31	120.2
O3—C7—C8	128.4 (4)	C30—C31—H31	120.2
N1—C7—C8	106.3 (4)	C31—C32—C33	120.4 (5)
C11—C8—C7	122.2 (4)	C31—C32—H32	119.8
C11—C8—C9	132.6 (4)	C33—C32—H32	119.8
C7—C8—C9	105.1 (4)	C32—C33—C34	120.5 (5)
N2—C9—C8	111.4 (4)	C32—C33—H33	119.7
N2—C9—C10	119.2 (4)	C34—C33—H33	119.7
C8—C9—C10	129.1 (4)	C29—C34—C33	119.6 (5)
C9—C10—H10A	109.5	C29—C34—H34	120.2
C9—C10—H10B	109.5	C33—C34—H34	120.2
H10A—C10—H10B	109.5	O7—C35—H35A	109.5
C9—C10—H10C	109.5	O7—C35—H35B	109.5
H10A—C10—H10C	109.5	H35A—C35—H35B	109.5
H10B—C10—H10C	109.5	O7—C35—H35C	109.5
O2—C11—C8	121.4 (4)	H35A—C35—H35C	109.5
O2—C11—C12	116.1 (4)	H35B—C35—H35C	109.5
C8—C11—C12	122.4 (4)	O36S—C36S—H36A	109.5
C13—C12—C17	119.7 (5)	O36S—C36S—H36B	109.5
C13—C12—C11	121.2 (4)	H36A—C36S—H36B	109.5
C17—C12—C11	118.8 (4)	O36S—C36S—H36C	109.5
C12—C13—C14	120.8 (5)	H36A—C36S—H36C	109.5
C12—C13—H13	119.6	H36B—C36S—H36C	109.5
C14—C13—H13	119.6	C7—N1—N2	111.4 (4)
C15—C14—C13	119.2 (5)	C7—N1—C1	128.8 (4)
C15—C14—H14	120.4	N2—N1—C1	119.7 (4)
C13—C14—H14	120.4	C9—N2—N1	105.8 (4)
C16—C15—C14	120.8 (5)	C24—N3—N4	111.7 (4)
C16—C15—H15	119.6	C24—N3—C18	129.4 (4)
C14—C15—H15	119.6	N4—N3—C18	118.9 (4)
C15—C16—C17	120.3 (5)	C26—N4—N3	105.4 (4)
C15—C16—H16	119.8	C24—O1—U1	122.6 (3)
C17—C16—H16	119.8	C11—O2—U1	133.4 (3)
C16—C17—C12	119.2 (5)	C7—O3—U1	122.7 (3)
C16—C17—H17	120.4	C28—O4—U1	134.8 (3)
C12—C17—H17	120.4	C35—O7—U1	131.0 (3)
C19—C18—C23	121.1 (5)	C35—O7—H7O	111 (4)
C19—C18—N3	119.7 (4)	U1—O7—H7O	115 (4)
C23—C18—N3	119.2 (5)	C36S—O36S—H36S	109.5
C20—C19—C18	118.2 (5)	O6—U1—O5	178.33 (15)
C20—C19—H19	120.9	O6—U1—O1	92.53 (13)
C18—C19—H19	120.9	O5—U1—O1	89.13 (14)
C19—C20—C21	120.6 (5)	O6—U1—O4	92.24 (14)
C19—C20—H20	119.7	O5—U1—O4	88.38 (14)
C21—C20—H20	119.7	O1—U1—O4	72.52 (12)
C22—C21—C20	120.1 (5)	O6—U1—O2	89.92 (14)
C22—C21—H21	119.9	O5—U1—O2	90.42 (14)
C20—C21—H21	119.9	O1—U1—O2	73.82 (12)
C21—C22—C23	120.8 (5)	O4—U1—O2	146.33 (12)
C21—C22—H22	119.6	O6—U1—O3	91.12 (13)
C23—C22—H22	119.6	O5—U1—O3	87.43 (14)
C22—C23—C18	119.1 (5)	O1—U1—O3	145.24 (12)
C22—C23—H23	120.4	O4—U1—O3	141.85 (11)
C18—C23—H23	120.4	O2—U1—O3	71.63 (11)
O1—C24—N3	123.2 (5)	O6—U1—O7	89.51 (14)
O1—C24—C25	129.8 (4)	O5—U1—O7	89.21 (14)
N3—C24—C25	107.1 (4)	O1—U1—O7	144.37 (12)
C28—C25—C24	122.9 (5)	O4—U1—O7	71.86 (12)
C28—C25—C26	133.4 (5)	O2—U1—O7	141.79 (12)
C24—C25—C26	103.7 (4)	O3—U1—O7	70.18 (12)
N4—C26—C25	112.1 (5)

C6—C1—C2—C3	0.2 (8)	C32—C33—C34—C29	−0.3 (7)
N1—C1—C2—C3	177.5 (5)	O3—C7—N1—N2	177.7 (4)
C1—C2—C3—C4	−0.7 (8)	C8—C7—N1—N2	−4.3 (5)
C2—C3—C4—C5	1.3 (8)	O3—C7—N1—C1	−6.7 (8)
C3—C4—C5—C6	−1.2 (8)	C8—C7—N1—C1	171.4 (4)
C4—C5—C6—C1	0.7 (8)	C2—C1—N1—C7	163.4 (5)
C2—C1—C6—C5	−0.2 (7)	C6—C1—N1—C7	−19.4 (7)
N1—C1—C6—C5	−177.4 (5)	C2—C1—N1—N2	−21.3 (7)
O3—C7—C8—C11	5.4 (8)	C6—C1—N1—N2	155.9 (4)
N1—C7—C8—C11	−172.6 (4)	C8—C9—N2—N1	−0.9 (5)
O3—C7—C8—C9	−178.5 (5)	C10—C9—N2—N1	−175.0 (4)
N1—C7—C8—C9	3.5 (5)	C7—N1—N2—C9	3.3 (5)
C11—C8—C9—N2	173.9 (5)	C1—N1—N2—C9	−172.8 (4)
C7—C8—C9—N2	−1.6 (6)	O1—C24—N3—N4	178.3 (4)
C11—C8—C9—C10	−12.8 (9)	C25—C24—N3—N4	−3.0 (5)
C7—C8—C9—C10	171.7 (5)	O1—C24—N3—C18	1.5 (8)
C7—C8—C11—O2	−20.2 (7)	C25—C24—N3—C18	−179.9 (4)
C9—C8—C11—O2	164.9 (5)	C19—C18—N3—C24	−37.5 (7)
C7—C8—C11—C12	155.9 (5)	C23—C18—N3—C24	144.1 (5)
C9—C8—C11—C12	−19.0 (8)	C19—C18—N3—N4	145.8 (5)
O2—C11—C12—C13	125.6 (5)	C23—C18—N3—N4	−32.6 (7)
C8—C11—C12—C13	−50.7 (7)	C25—C26—N4—N3	−1.4 (5)
O2—C11—C12—C17	−48.9 (6)	C27—C26—N4—N3	−178.8 (4)
C8—C11—C12—C17	134.8 (5)	C24—N3—N4—C26	2.8 (5)
C17—C12—C13—C14	0.5 (8)	C18—N3—N4—C26	−180.0 (4)
C11—C12—C13—C14	−174.0 (5)	N3—C24—O1—U1	−142.0 (4)
C12—C13—C14—C15	−1.6 (8)	C25—C24—O1—U1	39.7 (6)
C13—C14—C15—C16	1.3 (8)	C8—C11—O2—U1	−12.4 (7)
C14—C15—C16—C17	0.1 (8)	C12—C11—O2—U1	171.3 (3)
C15—C16—C17—C12	−1.3 (8)	N1—C7—O3—U1	−144.5 (4)
C13—C12—C17—C16	1.0 (7)	C8—C7—O3—U1	37.9 (6)
C11—C12—C17—C16	175.5 (5)	C25—C28—O4—U1	−11.9 (7)
C23—C18—C19—C20	−1.8 (8)	C29—C28—O4—U1	170.5 (3)
N3—C18—C19—C20	179.8 (5)	C24—O1—U1—O6	−131.8 (3)
C18—C19—C20—C21	1.2 (8)	C24—O1—U1—O5	48.3 (3)
C19—C20—C21—C22	0.1 (9)	C24—O1—U1—O4	−40.3 (3)
C20—C21—C22—C23	−0.8 (9)	C24—O1—U1—O2	139.0 (4)
C21—C22—C23—C18	0.1 (8)	C24—O1—U1—O3	132.6 (3)
C19—C18—C23—C22	1.2 (8)	C24—O1—U1—O7	−39.1 (4)
N3—C18—C23—C22	179.7 (5)	C28—O4—U1—O6	123.7 (4)
O1—C24—C25—C28	−1.6 (8)	C28—O4—U1—O5	−57.9 (4)
N3—C24—C25—C28	179.8 (4)	C28—O4—U1—O1	31.7 (4)
O1—C24—C25—C26	−179.4 (5)	C28—O4—U1—O2	30.5 (5)
N3—C24—C25—C26	2.0 (5)	C28—O4—U1—O3	−141.6 (4)
C28—C25—C26—N4	−177.8 (5)	C28—O4—U1—O7	−147.6 (5)
C24—C25—C26—N4	−0.3 (6)	C11—O2—U1—O6	126.2 (4)
C28—C25—C26—C27	−0.8 (9)	C11—O2—U1—O5	−52.2 (4)
C24—C25—C26—C27	176.7 (5)	C11—O2—U1—O1	−141.2 (5)
C24—C25—C28—O4	−14.2 (7)	C11—O2—U1—O4	−139.9 (4)
C26—C25—C28—O4	162.8 (5)	C11—O2—U1—O3	35.0 (4)
C24—C25—C28—C29	163.3 (4)	C11—O2—U1—O7	37.1 (5)
C26—C25—C28—C29	−19.7 (8)	C7—O3—U1—O6	−133.2 (4)
O4—C28—C29—C30	−42.5 (7)	C7—O3—U1—O5	47.7 (4)
C25—C28—C29—C30	139.9 (5)	C7—O3—U1—O1	−37.1 (4)
O4—C28—C29—C34	132.2 (5)	C7—O3—U1—O4	131.8 (3)
C25—C28—C29—C34	−45.4 (7)	C7—O3—U1—O2	−43.6 (3)
C34—C29—C30—C31	1.4 (8)	C7—O3—U1—O7	137.8 (4)
C28—C29—C30—C31	176.2 (5)	C35—O7—U1—O6	49.0 (4)
C29—C30—C31—C32	−0.3 (8)	C35—O7—U1—O5	−132.1 (4)
C30—C31—C32—C33	−1.2 (8)	C35—O7—U1—O1	−44.6 (5)
C31—C32—C33—C34	1.5 (8)	C35—O7—U1—O4	−43.5 (4)
C30—C29—C34—C33	−1.1 (7)	C35—O7—U1—O2	138.3 (4)
C28—C29—C34—C33	−175.8 (4)	C35—O7—U1—O3	140.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7O···O36Sⁱ	0.81 (2)	1.84 (5)	2.633 (6)	168 (5)
O36S—H36S···N2ⁱⁱ	0.82	2.12	2.878 (6)	153
C6—H6···O3	0.93	2.33	2.909 (7)	120
C19—H19···O1	0.93	2.54	2.989 (7)	110

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[U(C₁₇H₁₃N₂O₂)₂O₂(CH₄O)]·CH₄O
M_r	888.7
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	10.3353 (18), 12.988 (2), 13.955 (3)
α, β, γ (°)	69.938 (3), 81.728 (2), 70.722 (3)
V (Å³)	1659.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.95
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.242, 0.318
No. of measured, independent and observed [I > 2σ(I)] reflections	20251, 10125, 8127
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.096, 1.00
No. of reflections	10125
No. of parameters	450
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.45, −3.52

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

O1—U1	2.334 (3)	O5—U1	1.768 (3)
O2—U1	2.388 (3)	O6—U1	1.761 (3)
O3—U1	2.391 (3)	O7—U1	2.456 (3)
O4—U1	2.388 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7O···O36Sⁱ	0.811 (19)	1.84 (5)	2.633 (6)	168 (5)
O36S—H36S···N2ⁱⁱ	0.8200	2.1200	2.878 (6)	153.00
C6—H6···O3	0.9300	2.3300	2.909 (7)	120.00
C19—H19···O1	0.9300	2.5400	2.989 (7)	110.00

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2.

Acknowledgements

The authors thank the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique for financial support and Professor L. Ouahab (Laboratoire des Sciences Chimiques, Rennes1 France) for helpful discussions.

References

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