(Butan-2-ol-κO)[2-({(ethyl­sulfan­yl)[2-(2-oxidobenzyl­idene-κO)hydrazinyl­idene-κN2]meth­yl}imino­meth­yl)phenolato-κO]dioxidouranium(VI)

Takjoo, R.; Najafi, A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681200431X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m255-m256

doi:10.1107/S160053681200431X

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(Butan-2-ol-κO)[2-({(ethylsulfanyl)[2-(2-oxidobenzylidene-κO)hydrazinylidene-κN²]methyl}iminomethyl)phenolato-κO]dioxidouranium(VI)

Reza Takjoo,^a ‡ Atefeh Najafi,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 January 2012; accepted 1 February 2012; online 10 February 2012)

The U atom in the title complex, [U(C₁₇H₁₅N₃O₂S)O₂(C₄H₁₀O)], exists within a distorted pentagonal–bipyramidal geometry where the oxide O atoms occupy axial positions [O—U—O = 179.61 (18)°] and the pentagonal plane is defined by the N₂O₂ atoms of the tetradentate Schiff base ligand and the O atom of the butan-2-ol molecule. In the crystal, centrosymmetric aggregates are formed via pairs of hydroxy–phenoxide O—H⋯O hydrogen bonds. The azomethine C=N atoms, the ethylthiolyl group and the butyl group of the butan-2-ol molecule are disordered over two positions in a 0.668 (3):0.332 (3) ratio.

Related literature

For background to uranyl Schiff base complexes, see: Şahin et al. (2010 ); Özdemir et al. (2011 ). For a related structure, see: Takjoo et al. (2012 ).

Experimental

Crystal data

[U(C₁₇H₁₅N₃O₂S)O₂(C₄H₁₀O)]
M_r = 669.53
Monoclinic, P 2₁ /c
a = 11.3803 (2) Å
b = 14.3999 (3) Å
c = 14.0264 (4) Å
β = 97.326 (2)°
V = 2279.81 (9) Å³
Z = 4
Mo Kα radiation
μ = 7.25 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.265, T_max = 0.713
15878 measured reflections
5262 independent reflections
4493 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.078
S = 1.16
5262 reflections
302 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.16 e Å⁻³
Δρ_min = −0.81 e Å⁻³

Table 1
Selected bond lengths (Å)

U—O1	2.291 (4)
U—O2	2.229 (4)
U—O3	1.779 (4)
U—O4	1.776 (4)
U—O5	2.415 (4)
U—N1	2.562 (5)
U—N3	2.579 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1o⋯O1ⁱ	0.84 (1)	1.83 (2)	2.648 (6)	166 (7)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200431X/hb6617sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200431X/hb6617Isup2.hkl

checkCIF report

Comment top

Tetradentate ligands with N₂O₂ donor sets and their metal complexes attract attention as they provide synthetic models for the metal-containing sites in metallo-proteins and metallo-enzymes, and display extensive catalytic and bioactive applications. In this connection, recent studies of uranyl Schiff base complexes (Şahin et al., 2010; Özdemir et al., 2011) motivated the synthesis of the title complex, (I), in continuation of related studies (Takjoo et al., 2012).

The U atom in (I), Fig. 1, exists within a distorted pentagonal bipyramidal geometry with the axial positions occupied by the oxido-O atoms, O3—U—O4 = 179.61 (18)°. The pentagonal plane is defined by the N₂O₂ atoms, derived from the tetradentate Schiff base ligand, and the O atom of the butan-2-ol molecule, Table 1. The Schiff base ligand is somewhat twisted with the dihedral angle between the terminal benzene rings being 31.7 (3)°.

In the crystal structure, centrosymmetric pairs of molecules are linked via O—H···O hydrogen bonds formed between the hydroxyl and O1-phenoxide atoms, Fig. 2 and Table 2. The dimeric aggregates stack into columns parallel to c, Fig. 3.

Related literature top

For background to uranyl Schiff base complexes, see: Şahin et al. (2010); Özdemir et al. (2011). For a related structure, see: Takjoo et al. (2012).

Experimental top

UO₂(OAc)₂.2H₂O (0.42 g, 1.0 mmol) was added to a butanol solution (20 cm³) of salicylaldehyde mono-S-ethylisothiosemicarbazone hydrobromide (0.32 g, 1.0 mmol) and salicylaldehyde (0.12 g, 1.0 mmol). The red solution was heated under reflux for 1 h at 70 °C. Red prisms precipitated after four days, which were collected by filtration, washed with diethyl ether and dried in air. M.pt. 503 K. Yield: 25%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 70% probability level. Only the major component of the disordered residues is shown.
	Fig. 2. A view of the centrosymmetric aggregate in (I). The O—H···O hydrogen bonds are shown as dashed lines.
	Fig. 3. A view in projection down the c axis of the unit-cell contents of (I).

(Butan-2-ol-κO)[2-({(ethylsulfanyl)[2-(2-oxidobenzylidene- κO)hydrazinylidene-κN²]methyl}iminomethyl)phenolato- κO]dioxidouranium(VI) top

Crystal data top

[U(C₁₇H₁₅N₃O₂S)O₂(C₄H₁₀O)]	F(000) = 1280
M_r = 669.53	D_x = 1.951 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8576 reflections
a = 11.3803 (2) Å	θ = 2.2–27.5°
b = 14.3999 (3) Å	µ = 7.25 mm⁻¹
c = 14.0264 (4) Å	T = 100 K
β = 97.326 (2)°	Prism, red
V = 2279.81 (9) Å³	0.25 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5262 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4493 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −18→18
T_min = 0.265, T_max = 0.713	l = −18→12
15878 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0199P)² + 8.1201P] where P = (F_o² + 2F_c²)/3
5262 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 1.16 e Å⁻³
8 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

[U(C₁₇H₁₅N₃O₂S)O₂(C₄H₁₀O)]	V = 2279.81 (9) Å³
M_r = 669.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.3803 (2) Å	µ = 7.25 mm⁻¹
b = 14.3999 (3) Å	T = 100 K
c = 14.0264 (4) Å	0.25 × 0.10 × 0.05 mm
β = 97.326 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5262 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4493 reflections with I > 2σ(I)
T_min = 0.265, T_max = 0.713	R_int = 0.040
15878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	8 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 1.16 e Å⁻³
5262 reflections	Δρ_min = −0.81 e Å⁻³
302 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
U	0.717677 (17)	0.479390 (14)	0.617403 (15)	0.01623 (7)
S1	1.0356 (2)	0.23488 (16)	0.73678 (17)	0.0243 (6)	0.668 (3)
S1'	1.0688 (4)	0.2786 (3)	0.5310 (3)	0.024*	0.332 (3)
O1	0.6650 (3)	0.4824 (3)	0.4542 (3)	0.0239 (9)
O2	0.7142 (4)	0.5085 (3)	0.7731 (3)	0.0228 (9)
O3	0.8179 (3)	0.5740 (3)	0.6153 (3)	0.0190 (9)
O4	0.6169 (3)	0.3854 (3)	0.6190 (3)	0.0195 (9)
O5	0.5497 (3)	0.5832 (3)	0.6033 (3)	0.0237 (9)
H1o	0.486 (3)	0.554 (4)	0.590 (5)	0.036*
N1	0.8758 (4)	0.3968 (3)	0.5338 (3)	0.0186 (10)
N2	0.9541 (4)	0.3318 (3)	0.5841 (4)	0.0194 (11)	0.668 (3)
C8'	0.9541 (4)	0.3318 (3)	0.5841 (4)	0.0194 (11)	0.33
N3	0.8570 (4)	0.3646 (3)	0.7175 (3)	0.0194 (10)
C1	0.7233 (5)	0.5070 (4)	0.3817 (4)	0.0215 (13)
C2	0.6682 (5)	0.5611 (4)	0.3058 (4)	0.0244 (13)
H2	0.5910	0.5850	0.3088	0.029*
C3	0.7248 (5)	0.5801 (4)	0.2268 (4)	0.0262 (14)
H3	0.6865	0.6174	0.1763	0.031*
C4	0.8382 (6)	0.5450 (4)	0.2201 (4)	0.0296 (15)
H4	0.8764	0.5576	0.1651	0.036*
C5	0.8933 (5)	0.4923 (4)	0.2941 (4)	0.0246 (14)
H5	0.9699	0.4677	0.2894	0.030*
C6	0.8393 (5)	0.4738 (4)	0.3765 (4)	0.0192 (12)
C7	0.9043 (5)	0.4154 (4)	0.4491 (4)	0.0187 (12)
H7	0.9751	0.3878	0.4331	0.022*
C8	0.9416 (4)	0.3157 (4)	0.6716 (4)	0.0198 (12)	0.668 (3)
N2'	0.9416 (4)	0.3157 (4)	0.6716 (4)	0.0198 (12)	0.33
C9	1.1329 (10)	0.2017 (7)	0.6476 (9)	0.029 (3)	0.668 (3)
H9A	1.1528	0.2578	0.6121	0.035*	0.668 (3)
H9B	1.2076	0.1762	0.6813	0.035*	0.668 (3)
C9'	1.117 (2)	0.1895 (15)	0.621 (2)	0.029*	0.332 (3)
H9'A	1.1998	0.1722	0.6162	0.035*	0.332 (3)
H9'B	1.1135	0.2155	0.6862	0.035*	0.332 (3)
C10	1.0774 (11)	0.1312 (9)	0.5773 (9)	0.053 (4)	0.668 (3)
H10A	1.1324	0.1162	0.5312	0.080*	0.668 (3)
H10B	1.0040	0.1565	0.5429	0.080*	0.668 (3)
H10C	1.0595	0.0748	0.6118	0.080*	0.668 (3)
C10'	1.041 (3)	0.1044 (19)	0.609 (2)	0.053*	0.332 (3)
H10D	1.0712	0.0576	0.6562	0.080*	0.332 (3)
H10E	1.0417	0.0795	0.5438	0.080*	0.332 (3)
H10F	0.9591	0.1205	0.6179	0.080*	0.332 (3)
C11	0.8453 (5)	0.3368 (4)	0.8038 (4)	0.0254 (14)
H11	0.8910	0.2843	0.8265	0.031*
C12	0.7716 (5)	0.3761 (4)	0.8691 (4)	0.0259 (14)
C13	0.7682 (6)	0.3306 (5)	0.9574 (5)	0.0398 (18)
H13	0.8097	0.2737	0.9689	0.048*
C14	0.7077 (7)	0.3653 (6)	1.0269 (5)	0.0422 (19)
H14	0.7068	0.3329	1.0858	0.051*
C15	0.6474 (6)	0.4485 (5)	1.0108 (5)	0.0320 (15)
H15	0.6047	0.4731	1.0591	0.038*
C16	0.6485 (5)	0.4960 (4)	0.9258 (5)	0.0277 (14)
H16	0.6073	0.5534	0.9165	0.033*
C17	0.7097 (5)	0.4610 (4)	0.8523 (4)	0.0198 (13)
C18	0.6045 (6)	0.7293 (5)	0.5245 (5)	0.0350 (16)
H18A	0.5949	0.7969	0.5244	0.053*
H18B	0.5833	0.7054	0.4591	0.053*
H18C	0.6872	0.7135	0.5471	0.053*
C19	0.5234 (10)	0.6853 (7)	0.5916 (8)	0.044 (3)	0.668 (3)
H19	0.4405	0.6907	0.5585	0.053*	0.668 (3)
C19'	0.574 (2)	0.6858 (9)	0.6188 (10)	0.044*	0.332 (3)
H19'	0.6420	0.6942	0.6704	0.053*	0.332 (3)
C20	0.5226 (12)	0.7204 (9)	0.6886 (9)	0.051 (3)	0.668 (3)
H20A	0.6052	0.7169	0.7207	0.062*	0.668 (3)
H20B	0.5022	0.7872	0.6827	0.062*	0.668 (3)
C20'	0.468 (2)	0.725 (2)	0.650 (2)	0.051*	0.332 (3)
H20C	0.4803	0.7928	0.6609	0.062*	0.332 (3)
H20D	0.4010	0.7179	0.5981	0.062*	0.332 (3)
C21	0.4487 (16)	0.6807 (19)	0.7538 (10)	0.042 (4)	0.668 (3)
H21A	0.4618	0.7135	0.8154	0.063*	0.668 (3)
H21B	0.4686	0.6149	0.7639	0.063*	0.668 (3)
H21C	0.3654	0.6865	0.7265	0.063*	0.668 (3)
C21'	0.434 (4)	0.685 (4)	0.737 (3)	0.042*	0.332 (3)
H21D	0.3639	0.7177	0.7544	0.063*	0.332 (3)
H21E	0.4992	0.6910	0.7889	0.063*	0.332 (3)
H21F	0.4146	0.6193	0.7256	0.063*	0.332 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
U	0.01237 (10)	0.01495 (11)	0.02069 (11)	0.00117 (9)	−0.00049 (8)	0.00006 (10)
S1	0.0231 (11)	0.0219 (12)	0.0267 (13)	0.0079 (9)	−0.0014 (10)	0.0046 (10)
O1	0.0144 (19)	0.033 (2)	0.024 (2)	0.0056 (18)	−0.0006 (17)	0.0000 (19)
O2	0.026 (2)	0.020 (2)	0.022 (2)	−0.0008 (17)	0.0038 (18)	−0.0006 (17)
O3	0.0125 (18)	0.018 (2)	0.028 (2)	0.0010 (16)	0.0060 (17)	0.0025 (17)
O4	0.0133 (19)	0.018 (2)	0.028 (2)	0.0001 (16)	0.0037 (17)	−0.0015 (17)
O5	0.018 (2)	0.016 (2)	0.037 (3)	0.0032 (17)	0.004 (2)	−0.0016 (19)
N1	0.016 (2)	0.019 (2)	0.019 (3)	0.002 (2)	−0.005 (2)	0.001 (2)
N2	0.018 (3)	0.016 (3)	0.023 (3)	0.006 (2)	−0.001 (2)	−0.003 (2)
C8'	0.018 (3)	0.016 (3)	0.023 (3)	0.006 (2)	−0.001 (2)	−0.003 (2)
N3	0.015 (2)	0.022 (3)	0.021 (3)	0.002 (2)	0.000 (2)	−0.002 (2)
C1	0.023 (3)	0.018 (3)	0.022 (3)	0.001 (2)	−0.001 (3)	−0.003 (2)
C2	0.018 (3)	0.027 (3)	0.025 (3)	0.007 (3)	−0.005 (3)	0.000 (3)
C3	0.026 (3)	0.028 (3)	0.024 (3)	0.007 (3)	−0.001 (3)	0.005 (3)
C4	0.038 (4)	0.034 (4)	0.016 (3)	−0.001 (3)	0.003 (3)	0.007 (3)
C5	0.023 (3)	0.030 (4)	0.021 (3)	0.000 (3)	0.002 (3)	−0.003 (3)
C6	0.015 (3)	0.022 (3)	0.019 (3)	0.003 (2)	−0.004 (2)	0.003 (3)
C7	0.012 (3)	0.021 (3)	0.024 (3)	0.002 (2)	0.003 (2)	−0.002 (2)
C8	0.016 (3)	0.019 (3)	0.024 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
N2'	0.016 (3)	0.019 (3)	0.024 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C9	0.018 (6)	0.025 (6)	0.042 (8)	0.012 (4)	−0.004 (5)	0.002 (5)
C10	0.044 (8)	0.051 (9)	0.062 (9)	0.027 (7)	−0.002 (6)	−0.009 (7)
C11	0.020 (3)	0.026 (3)	0.029 (3)	0.008 (3)	−0.003 (3)	0.004 (3)
C12	0.023 (3)	0.032 (4)	0.023 (3)	0.001 (3)	0.004 (3)	0.010 (3)
C13	0.041 (4)	0.047 (5)	0.033 (4)	0.020 (4)	0.010 (3)	0.013 (3)
C14	0.045 (4)	0.061 (5)	0.022 (4)	0.012 (4)	0.009 (3)	0.014 (3)
C15	0.028 (3)	0.047 (4)	0.022 (3)	0.007 (3)	0.004 (3)	−0.009 (3)
C16	0.020 (3)	0.034 (4)	0.029 (3)	−0.001 (3)	0.003 (3)	−0.003 (3)
C17	0.017 (3)	0.026 (3)	0.016 (3)	−0.008 (2)	−0.001 (2)	0.000 (2)
C18	0.033 (4)	0.035 (4)	0.035 (4)	−0.002 (3)	−0.002 (3)	0.000 (3)
C19	0.038 (7)	0.049 (7)	0.050 (7)	0.005 (6)	0.020 (6)	−0.016 (6)
C20	0.051 (8)	0.046 (7)	0.057 (9)	−0.018 (6)	0.005 (6)	−0.002 (6)
C21	0.041 (8)	0.056 (8)	0.026 (7)	0.010 (6)	−0.008 (7)	−0.005 (7)

Geometric parameters (Å, º) top

U—O1	2.291 (4)	C10—H10B	0.9800
U—O2	2.229 (4)	C10—H10C	0.9800
U—O3	1.779 (4)	C10'—H10D	0.9800
U—O4	1.776 (4)	C10'—H10E	0.9800
U—O5	2.415 (4)	C10'—H10F	0.9800
U—N1	2.562 (5)	C11—C12	1.435 (9)
U—N3	2.579 (5)	C11—H11	0.9500
S1—C8	1.757 (5)	C12—C13	1.405 (9)
S1—C9	1.836 (12)	C12—C17	1.416 (8)
S1'—C9'	1.835 (15)	C13—C14	1.357 (10)
O1—C1	1.331 (7)	C13—H13	0.9500
O2—C17	1.311 (7)	C14—C15	1.385 (10)
O5—C19	1.506 (10)	C14—H14	0.9500
O5—C19'	1.513 (13)	C15—C16	1.376 (9)
O5—H1o	0.839 (10)	C15—H15	0.9500
N1—C7	1.299 (7)	C16—C17	1.409 (8)
N1—N2	1.417 (6)	C16—H16	0.9500
N2—C8	1.274 (7)	C18—C19	1.537 (11)
N3—C11	1.298 (8)	C18—C19'	1.544 (13)
N3—C8	1.412 (7)	C18—H18A	0.9800
C1—C2	1.402 (8)	C18—H18B	0.9800
C1—C6	1.414 (8)	C18—H18C	0.9800
C2—C3	1.378 (9)	C19—C20	1.453 (13)
C2—H2	0.9500	C19—H19	1.0000
C3—C4	1.399 (9)	C19'—C20'	1.455 (15)
C3—H3	0.9500	C19'—H19'	1.0000
C4—C5	1.371 (8)	C20—C21	1.438 (14)
C4—H4	0.9500	C20—H20A	0.9900
C5—C6	1.402 (8)	C20—H20B	0.9900
C5—H5	0.9500	C20'—C21'	1.439 (16)
C6—C7	1.449 (8)	C20'—H20C	0.9900
C7—H7	0.9500	C20'—H20D	0.9900
C9—C10	1.498 (13)	C21—H21A	0.9800
C9—H9A	0.9900	C21—H21B	0.9800
C9—H9B	0.9900	C21—H21C	0.9800
C9'—C10'	1.497 (15)	C21'—H21D	0.9800
C9'—H9'A	0.9900	C21'—H21E	0.9800
C9'—H9'B	0.9900	C21'—H21F	0.9800
C10—H10A	0.9800

O4—U—O3	179.61 (18)	H10A—C10—H10B	109.5
O4—U—O2	92.23 (16)	C9—C10—H10C	109.5
O3—U—O2	87.92 (16)	H10A—C10—H10C	109.5
O4—U—O1	86.55 (17)	H10B—C10—H10C	109.5
O3—U—O1	93.18 (16)	C9'—C10'—H10D	109.5
O2—U—O1	160.07 (14)	C9'—C10'—H10E	109.5
O4—U—O5	88.12 (15)	H10D—C10'—H10E	109.5
O3—U—O5	91.55 (15)	C9'—C10'—H10F	109.5
O2—U—O5	81.44 (15)	H10D—C10'—H10F	109.5
O1—U—O5	78.64 (14)	H10E—C10'—H10F	109.5
O4—U—N1	98.29 (16)	N3—C11—C12	127.8 (5)
O3—U—N1	81.88 (16)	N3—C11—H11	116.1
O2—U—N1	129.55 (14)	C12—C11—H11	116.1
O1—U—N1	70.20 (14)	C13—C12—C17	118.7 (6)
O5—U—N1	147.64 (15)	C13—C12—C11	117.6 (6)
O4—U—N3	81.81 (16)	C17—C12—C11	123.5 (5)
O3—U—N3	98.57 (16)	C14—C13—C12	122.3 (7)
O2—U—N3	70.97 (15)	C14—C13—H13	118.8
O1—U—N3	128.32 (15)	C12—C13—H13	118.8
O5—U—N3	150.10 (15)	C13—C14—C15	119.2 (6)
N1—U—N3	62.11 (15)	C13—C14—H14	120.4
C8—S1—C9	101.4 (4)	C15—C14—H14	120.4
C1—O1—U	132.5 (4)	C16—C15—C14	120.8 (6)
C17—O2—U	137.7 (4)	C16—C15—H15	119.6
C19—O5—U	139.3 (5)	C14—C15—H15	119.6
C19'—O5—U	117.8 (9)	C15—C16—C17	121.1 (6)
C19—O5—H1o	108 (5)	C15—C16—H16	119.5
C19'—O5—H1o	131 (5)	C17—C16—H16	119.5
U—O5—H1o	111 (5)	O2—C17—C16	120.6 (5)
C7—N1—N2	112.1 (5)	O2—C17—C12	121.3 (5)
C7—N1—U	126.5 (4)	C16—C17—C12	118.0 (5)
N2—N1—U	120.9 (3)	C19—C18—H18A	109.5
C8—N2—N1	117.3 (4)	C19—C18—H18B	109.5
C11—N3—C8	115.4 (5)	H18A—C18—H18B	109.5
C11—N3—U	125.1 (4)	C19—C18—H18C	109.5
C8—N3—U	118.6 (3)	H18A—C18—H18C	109.5
O1—C1—C2	120.7 (5)	H18B—C18—H18C	109.5
O1—C1—C6	120.6 (5)	C20—C19—O5	105.2 (9)
C2—C1—C6	118.6 (6)	C20—C19—C18	120.4 (9)
C3—C2—C1	120.7 (6)	O5—C19—C18	110.0 (6)
C3—C2—H2	119.6	C20—C19—H19	106.8
C1—C2—H2	119.6	O5—C19—H19	106.8
C2—C3—C4	120.8 (6)	C18—C19—H19	106.8
C2—C3—H3	119.6	C20'—C19'—O5	106.5 (17)
C4—C3—H3	119.6	C20'—C19'—C18	113.0 (17)
C5—C4—C3	119.1 (6)	O5—C19'—C18	109.2 (8)
C5—C4—H4	120.5	C20'—C19'—H19'	109.3
C3—C4—H4	120.5	O5—C19'—H19'	109.3
C4—C5—C6	121.5 (6)	C18—C19'—H19'	109.3
C4—C5—H5	119.3	C21—C20—C19	122.1 (13)
C6—C5—H5	119.3	C21—C20—H20A	106.8
C5—C6—C1	119.3 (5)	C19—C20—H20A	106.8
C5—C6—C7	116.8 (5)	C21—C20—H20B	106.8
C1—C6—C7	123.8 (5)	C19—C20—H20B	106.8
N1—C7—C6	126.7 (5)	H20A—C20—H20B	106.7
N1—C7—H7	116.7	C21'—C20'—C19'	115 (3)
C6—C7—H7	116.7	C21'—C20'—H20C	108.6
N2—C8—N3	121.0 (4)	C19'—C20'—H20C	108.6
N2—C8—S1	119.1 (4)	C21'—C20'—H20D	108.6
N3—C8—S1	119.9 (4)	C19'—C20'—H20D	108.6
C10—C9—S1	112.6 (9)	H20C—C20'—H20D	107.5
C10—C9—H9A	109.1	C20—C21—H21A	109.5
S1—C9—H9A	109.1	C20—C21—H21B	109.5
C10—C9—H9B	109.1	H21A—C21—H21B	109.5
S1—C9—H9B	109.1	C20—C21—H21C	109.5
H9A—C9—H9B	107.8	H21A—C21—H21C	109.5
C10'—C9'—S1'	112.0 (17)	H21B—C21—H21C	109.5
C10'—C9'—H9'A	109.2	C20'—C21'—H21D	109.5
S1'—C9'—H9'A	109.2	C20'—C21'—H21E	109.5
C10'—C9'—H9'B	109.2	H21D—C21'—H21E	109.5
S1'—C9'—H9'B	109.2	C20'—C21'—H21F	109.5
H9'A—C9'—H9'B	107.9	H21D—C21'—H21F	109.5
C9—C10—H10A	109.5	H21E—C21'—H21F	109.5
C9—C10—H10B	109.5

O4—U—O1—C1	−150.2 (5)	C2—C3—C4—C5	−0.9 (10)
O3—U—O1—C1	30.1 (5)	C3—C4—C5—C6	−0.8 (10)
O2—U—O1—C1	122.8 (5)	C4—C5—C6—C1	2.7 (9)
O5—U—O1—C1	121.0 (5)	C4—C5—C6—C7	178.5 (6)
N1—U—O1—C1	−50.1 (5)	O1—C1—C6—C5	172.9 (5)
N3—U—O1—C1	−73.5 (5)	C2—C1—C6—C5	−2.9 (8)
O4—U—O2—C17	37.7 (5)	O1—C1—C6—C7	−2.6 (9)
O3—U—O2—C17	−142.6 (5)	C2—C1—C6—C7	−178.4 (5)
O1—U—O2—C17	123.7 (6)	N2—N1—C7—C6	175.5 (5)
O5—U—O2—C17	125.5 (5)	U—N1—C7—C6	−12.5 (8)
N1—U—O2—C17	−65.0 (6)	C5—C6—C7—N1	173.2 (6)
N3—U—O2—C17	−42.8 (5)	C1—C6—C7—N1	−11.2 (9)
O4—U—O5—C19	−176.8 (7)	N1—N2—C8—N3	−3.1 (8)
O3—U—O5—C19	3.0 (7)	N1—N2—C8—S1	179.5 (4)
O2—U—O5—C19	90.7 (7)	C11—N3—C8—N2	174.3 (5)
O1—U—O5—C19	−89.9 (7)	U—N3—C8—N2	4.1 (7)
N1—U—O5—C19	−74.2 (8)	C11—N3—C8—S1	−8.3 (7)
N3—U—O5—C19	113.3 (7)	U—N3—C8—S1	−178.5 (2)
O4—U—O5—C19'	167.3 (6)	C9—S1—C8—N2	2.3 (6)
O3—U—O5—C19'	−12.9 (6)	C9—S1—C8—N3	−175.1 (5)
O2—U—O5—C19'	74.8 (6)	C8—S1—C9—C10	−80.6 (9)
O1—U—O5—C19'	−105.8 (6)	C8—N3—C11—C12	176.4 (6)
N1—U—O5—C19'	−90.1 (6)	U—N3—C11—C12	−14.1 (9)
N3—U—O5—C19'	97.4 (6)	N3—C11—C12—C13	176.4 (7)
O4—U—N1—C7	113.7 (5)	N3—C11—C12—C17	−8.4 (10)
O3—U—N1—C7	−66.0 (5)	C17—C12—C13—C14	0.0 (11)
O2—U—N1—C7	−146.5 (4)	C11—C12—C13—C14	175.5 (7)
O1—U—N1—C7	30.4 (4)	C12—C13—C14—C15	−0.2 (12)
O5—U—N1—C7	14.0 (6)	C13—C14—C15—C16	−0.2 (11)
N3—U—N1—C7	−170.2 (5)	C14—C15—C16—C17	0.8 (10)
O4—U—N1—N2	−75.1 (4)	U—O2—C17—C16	−145.9 (5)
O3—U—N1—N2	105.3 (4)	U—O2—C17—C12	37.9 (8)
O2—U—N1—N2	24.8 (4)	C15—C16—C17—O2	−177.3 (6)
O1—U—N1—N2	−158.4 (4)	C15—C16—C17—C12	−1.0 (9)
O5—U—N1—N2	−174.8 (3)	C13—C12—C17—O2	176.9 (6)
N3—U—N1—N2	1.0 (3)	C11—C12—C17—O2	1.7 (9)
C7—N1—N2—C8	173.0 (5)	C13—C12—C17—C16	0.6 (9)
U—N1—N2—C8	0.6 (6)	C11—C12—C17—C16	−174.6 (6)
O4—U—N3—C11	−67.7 (5)	C19'—O5—C19—C20	−58.1 (15)
O3—U—N3—C11	112.3 (5)	U—O5—C19—C20	−93.5 (9)
O2—U—N3—C11	27.6 (5)	C19'—O5—C19—C18	73.0 (11)
O1—U—N3—C11	−146.7 (4)	U—O5—C19—C18	37.6 (12)
O5—U—N3—C11	3.9 (6)	C19'—C18—C19—C20	49.7 (16)
N1—U—N3—C11	−171.6 (5)	C19'—C18—C19—O5	−72.9 (11)
O4—U—N3—C8	101.5 (4)	C19—O5—C19'—C20'	51.0 (19)
O3—U—N3—C8	−78.5 (4)	U—O5—C19'—C20'	−154.3 (14)
O2—U—N3—C8	−163.3 (4)	C19—O5—C19'—C18	−71.3 (11)
O1—U—N3—C8	22.5 (4)	U—O5—C19'—C18	83.4 (14)
O5—U—N3—C8	173.0 (3)	C19—C18—C19'—C20'	−47 (2)
N1—U—N3—C8	−2.5 (3)	C19—C18—C19'—O5	71.2 (11)
U—O1—C1—C2	−136.4 (5)	O5—C19—C20—C21	−54.6 (18)
U—O1—C1—C6	47.9 (8)	C18—C19—C20—C21	−179.5 (14)
O1—C1—C2—C3	−174.5 (6)	O5—C19'—C20'—C21'	58 (4)
C6—C1—C2—C3	1.3 (9)	C18—C19'—C20'—C21'	178 (3)
C1—C2—C3—C4	0.6 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1o···O1ⁱ	0.84 (1)	1.83 (2)	2.648 (6)	166 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[U(C₁₇H₁₅N₃O₂S)O₂(C₄H₁₀O)]
M_r	669.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.3803 (2), 14.3999 (3), 14.0264 (4)
β (°)	97.326 (2)
V (Å³)	2279.81 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.25
Crystal size (mm)	0.25 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.265, 0.713
No. of measured, independent and observed [I > 2σ(I)] reflections	15878, 5262, 4493
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.078, 1.16
No. of reflections	5262
No. of parameters	302
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.16, −0.81

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

U—O1	2.291 (4)	U—O5	2.415 (4)
U—O2	2.229 (4)	U—N1	2.562 (5)
U—O3	1.779 (4)	U—N3	2.579 (5)
U—O4	1.776 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1o···O1ⁱ	0.84 (1)	1.83 (2)	2.648 (6)	166 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: rezatakjoo@yahoo.com.

Acknowledgements

We gratefully acknowledge financial support of this study by Ferdowsi University of Mashhad, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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Özdemir, N., Şahin, M., Bal-Demirci, T. & Ülküseven, B. (2011). Polyhedron, 30, 515–521. Google Scholar
Şahin, M., Koca, A., Özdemir, N., Dinçer, M., Büyükgüngör, O., Bal-Demirci, T. & Ülküseven, B. (2010). Dalton Trans. 39, 10228–10237. Web of Science PubMed Google Scholar
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