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

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

doi:10.1107/S1600536812003789

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m244-m245

doi:10.1107/S1600536812003789

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

Reza Takjoo,^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 24 January 2012; accepted 28 January 2012; online 4 February 2012)

The U^VI atom in the title complex, [U(C₁₇H₁₅N₃O₂S)O₂(C₂H₆OS)], exists within a distorted pentagonal–pyramidal geometry where the oxide atoms occupy axial positions [O—U—O = 177.84 (14)°] and the pentagonal plane is defined by the N₂O₂ atoms of the tetradentate Schiff base ligand and the O atom of the dimethyl sulfoxide molecule. In the crystal, centrosymmetric aggregates are formed via pairs of C—H⋯O interactions. The azomethine C=N atoms and ethylthiolyl group are disordered over two orientations in a 0.828 (3):0.172 (3) ratio.

Related literature

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

Experimental

Crystal data

[U(C₁₇H₁₅N₃O₂S)O₂(C₂H₆OS)]
M_r = 673.54
Monoclinic, P 2₁ /n
a = 11.6988 (3) Å
b = 15.4972 (3) Å
c = 12.2246 (3) Å
β = 105.714 (3)°
V = 2133.47 (9) Å³
Z = 4
Mo Kα radiation
μ = 7.84 mm⁻¹
T = 100 K
0.18 × 0.12 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.333, T_max = 0.508
19265 measured reflections
4927 independent reflections
4237 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.063
S = 1.01
4927 reflections
281 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −1.52 e Å⁻³

Table 1
Selected bond lengths (Å)

U—O1	2.267 (3)
U—O2	2.233 (3)
U—O3	1.787 (3)
U—O4	1.792 (3)
U—O5	2.395 (3)
U—N1	2.547 (4)
U—N3	2.603 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.95	2.48	3.322 (5)	147
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: ORTEP-3 (Farrugia, 1997 ) 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/S1600536812003789/hb6614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003789/hb6614Isup2.hkl

checkCIF report

Comment top

Tetradentate ligands with N₂O₂ donor sets and their metal complexes are of great importance as they provide synthetic models for the metal-containing sites in metallo-proteins and metallo-enzymes, and display extensive catalytic and bioactive applications. Such considerations have motivated recent studies of uranyl Schiff base complexes (Şahin et al., 2010; Özdemir et al., 2011) and led to the synthesis of the title complex, (I).

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 = 177.84 (14)°. The pentagonal plane is defined by the N₂O₂ atoms, derived from the tetradentate Schiff base ligand, and the O atom of the dimethyl sulfoxide molecule, Table 1. The Schiff base ligand is somewhat buckled with the dihedral angle between the terminal benzene rings being 35.6 (2)°. The S-bound substituents are directed to one side of the molecule, Fig. 1.

In the crystal structure, centrosymmetric pairs of molecules are linked via C—H···O(oxido) interactions, 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).

Experimental top

UO₂(OAc)₂.2H₂O (0.42 g, 1.0 mmol) was added to an ethanol (20 cm³) solution 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 crystals of the product, (I), precipitated after three days, collected by filtration, washed with ethanol, and dried in air. Recrystallization was by slow evaporation (10 days) of a dimethyl sulfoxide solution of (I) which yielded red crystals. M.pt. 513 K. Yield: 46%.

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: ORTEP-3 (Farrugia, 1997) 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 residue is shown.
	Fig. 2. A view of the centrosymmetric aggregate in (I). The C—H···O interactions are shown as dashed lines.
	Fig. 3. A view in projection down the c axis of the unit-cell contents of (I).

(Dimethyl sulfoxide-κO)[2-({(ethylsulfanyl)[2-(2-oxidobenzylidene- κO<ι>)hydrazinylidene-κN²]methyl}iminomethyl)phenolato- κO]dioxidouranium(VI) top

Crystal data top

[U(C₁₇H₁₅N₃O₂S)O₂(C₂H₆OS)]	F(000) = 1280
M_r = 673.54	D_x = 2.097 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8576 reflections
a = 11.6988 (3) Å	θ = 2.2–27.5°
b = 15.4972 (3) Å	µ = 7.84 mm⁻¹
c = 12.2246 (3) Å	T = 100 K
β = 105.714 (3)°	Prism, red
V = 2133.47 (9) Å³	0.18 × 0.12 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4927 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4237 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.044
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scan	h = −14→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→20
T_min = 0.333, T_max = 0.508	l = −15→11
19265 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0243P)² + 4.2587P] where P = (F_o² + 2F_c²)/3
4927 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.98 e Å⁻³
3 restraints	Δρ_min = −1.52 e Å⁻³

Crystal data top

[U(C₁₇H₁₅N₃O₂S)O₂(C₂H₆OS)]	V = 2133.47 (9) Å³
M_r = 673.54	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.6988 (3) Å	µ = 7.84 mm⁻¹
b = 15.4972 (3) Å	T = 100 K
c = 12.2246 (3) Å	0.18 × 0.12 × 0.10 mm
β = 105.714 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4927 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4237 reflections with I > 2σ(I)
T_min = 0.333, T_max = 0.508	R_int = 0.044
19265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	3 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.01	Δρ_max = 0.98 e Å⁻³
4927 reflections	Δρ_min = −1.52 e Å⁻³
281 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
U	0.364161 (13)	0.640410 (10)	0.689855 (13)	0.01292 (6)
S1	0.15547 (15)	0.46851 (11)	0.34195 (14)	0.0341 (5)	0.828 (3)
S1'	0.0795 (7)	0.3967 (5)	0.5070 (7)	0.034*	0.172 (3)
S2	0.58169 (11)	0.77489 (8)	0.88184 (11)	0.0260 (3)
O1	0.4057 (3)	0.72624 (19)	0.5554 (3)	0.0171 (7)
O2	0.3653 (3)	0.5871 (2)	0.8599 (3)	0.0257 (8)
O3	0.2236 (3)	0.69271 (19)	0.6677 (3)	0.0169 (7)
O4	0.5046 (2)	0.58833 (18)	0.7065 (3)	0.0168 (7)
O5	0.4562 (3)	0.7596 (2)	0.8050 (3)	0.0220 (7)
N1	0.3115 (3)	0.5629 (2)	0.4990 (3)	0.0145 (8)
N2	0.1805 (3)	0.4702 (2)	0.5585 (3)	0.0211 (9)	0.828 (3)
C8'	0.1805 (3)	0.4702 (2)	0.5585 (3)	0.0211 (9)	0.172
N3	0.2299 (3)	0.5040 (2)	0.6674 (3)	0.0150 (8)
C1	0.4713 (4)	0.7110 (3)	0.4855 (4)	0.0140 (9)
C2	0.5515 (4)	0.7744 (3)	0.4682 (4)	0.0194 (10)
H2	0.5603	0.8270	0.5096	0.023*
C3	0.6170 (4)	0.7605 (3)	0.3915 (4)	0.0204 (10)
H3	0.6708	0.8036	0.3812	0.025*
C4	0.6058 (4)	0.6841 (3)	0.3285 (4)	0.0195 (10)
H4	0.6517	0.6756	0.2761	0.023*
C5	0.5290 (4)	0.6222 (3)	0.3427 (4)	0.0194 (10)
H5	0.5202	0.5709	0.2986	0.023*
C6	0.4613 (4)	0.6331 (3)	0.4226 (4)	0.0157 (9)
C7	0.3764 (4)	0.5671 (3)	0.4269 (4)	0.0148 (9)
H7	0.3662	0.5222	0.3721	0.018*
N2'	0.2226 (4)	0.4984 (3)	0.4777 (4)	0.0225 (10)	0.172 (3)
C8	0.2226 (4)	0.4984 (3)	0.4777 (4)	0.0225 (10)	0.828 (3)
C9	0.0485 (5)	0.3874 (4)	0.3578 (6)	0.0248 (15)	0.828 (3)
H9A	0.0055	0.4093	0.4116	0.030*	0.828 (3)
H9B	−0.0105	0.3790	0.2834	0.030*	0.828 (3)
C9'	0.097 (3)	0.3909 (19)	0.3636 (16)	0.025*	0.172 (3)
H9'A	0.0164	0.3980	0.3113	0.030*	0.172 (3)
H9'B	0.1427	0.4426	0.3538	0.030*	0.172 (3)
C10	0.1023 (6)	0.3020 (5)	0.3993 (6)	0.0410 (18)	0.828 (3)
H10A	0.0395	0.2618	0.4051	0.061*	0.828 (3)
H10B	0.1588	0.3091	0.4742	0.061*	0.828 (3)
H10C	0.1437	0.2791	0.3458	0.061*	0.828 (3)
C10'	0.152 (3)	0.3162 (19)	0.320 (3)	0.041*	0.172 (3)
H10D	0.1517	0.3270	0.2410	0.061*	0.172 (3)
H10E	0.1065	0.2637	0.3240	0.061*	0.172 (3)
H10F	0.2339	0.3088	0.3665	0.061*	0.172 (3)
C11	0.1832 (4)	0.4694 (3)	0.7413 (4)	0.0167 (9)
H11	0.1265	0.4251	0.7142	0.020*
C12	0.2075 (4)	0.4904 (3)	0.8601 (4)	0.0183 (10)
C13	0.1371 (4)	0.4507 (3)	0.9225 (4)	0.0241 (11)
H13	0.0770	0.4111	0.8856	0.029*
C14	0.1538 (4)	0.4683 (4)	1.0362 (4)	0.0290 (12)
H14	0.1043	0.4424	1.0770	0.035*
C15	0.2443 (5)	0.5245 (3)	1.0904 (4)	0.0274 (11)
H15	0.2567	0.5363	1.1690	0.033*
C16	0.3160 (4)	0.5633 (3)	1.0326 (4)	0.0247 (11)
H16	0.3781	0.6004	1.0720	0.030*
C17	0.2984 (4)	0.5486 (3)	0.9154 (4)	0.0185 (10)
C18	0.6216 (5)	0.6806 (3)	0.9658 (4)	0.0290 (12)
H18A	0.5758	0.6778	1.0219	0.044*
H18B	0.7066	0.6824	1.0050	0.044*
H18C	0.6046	0.6296	0.9168	0.044*
C19	0.6776 (5)	0.7611 (5)	0.7925 (5)	0.0467 (16)
H19A	0.6667	0.8091	0.7384	0.070*
H19B	0.6589	0.7066	0.7508	0.070*
H19C	0.7603	0.7599	0.8390	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
U	0.01231 (9)	0.01200 (8)	0.01301 (9)	−0.00072 (6)	0.00096 (6)	−0.00015 (7)
S1	0.0401 (10)	0.0365 (9)	0.0277 (9)	−0.0149 (8)	0.0128 (8)	−0.0043 (8)
S2	0.0302 (7)	0.0166 (6)	0.0228 (6)	−0.0051 (5)	−0.0073 (5)	−0.0024 (5)
O1	0.0220 (16)	0.0111 (14)	0.0189 (16)	−0.0001 (12)	0.0067 (14)	0.0000 (13)
O2	0.0299 (18)	0.0282 (18)	0.0153 (16)	−0.0136 (15)	−0.0002 (15)	0.0032 (15)
O3	0.0139 (15)	0.0169 (15)	0.0200 (16)	0.0015 (13)	0.0043 (13)	0.0003 (14)
O4	0.0142 (15)	0.0110 (14)	0.0210 (16)	−0.0005 (12)	−0.0025 (13)	−0.0033 (13)
O5	0.0246 (17)	0.0159 (16)	0.0203 (17)	0.0008 (13)	−0.0027 (15)	−0.0029 (14)
N1	0.0130 (17)	0.0141 (18)	0.0143 (18)	−0.0002 (14)	0.0000 (15)	0.0009 (16)
N2	0.024 (2)	0.021 (2)	0.015 (2)	−0.0050 (17)	−0.0008 (18)	−0.0024 (18)
C8'	0.024 (2)	0.021 (2)	0.015 (2)	−0.0050 (17)	−0.0008 (18)	−0.0024 (18)
N3	0.0130 (17)	0.0159 (18)	0.0138 (18)	−0.0002 (15)	0.0001 (15)	0.0008 (16)
C1	0.0110 (19)	0.015 (2)	0.014 (2)	0.0033 (17)	−0.0005 (18)	0.0018 (18)
C2	0.024 (2)	0.014 (2)	0.020 (2)	−0.0011 (18)	0.006 (2)	0.0013 (19)
C3	0.021 (2)	0.015 (2)	0.026 (3)	−0.0033 (18)	0.008 (2)	0.005 (2)
C4	0.020 (2)	0.021 (2)	0.019 (2)	0.0057 (19)	0.010 (2)	0.004 (2)
C5	0.020 (2)	0.018 (2)	0.022 (2)	0.0042 (18)	0.010 (2)	0.003 (2)
C6	0.016 (2)	0.014 (2)	0.015 (2)	0.0026 (17)	0.0004 (18)	0.0012 (18)
C7	0.017 (2)	0.013 (2)	0.012 (2)	−0.0002 (17)	0.0006 (18)	−0.0017 (18)
N2'	0.021 (2)	0.018 (2)	0.022 (2)	−0.0031 (19)	−0.007 (2)	0.003 (2)
C8	0.021 (2)	0.018 (2)	0.022 (2)	−0.0031 (19)	−0.007 (2)	0.003 (2)
C9	0.013 (3)	0.026 (3)	0.033 (4)	−0.008 (3)	0.000 (3)	−0.005 (3)
C10	0.035 (4)	0.046 (4)	0.041 (4)	−0.009 (3)	0.008 (3)	−0.001 (4)
C11	0.012 (2)	0.015 (2)	0.020 (2)	−0.0007 (17)	−0.0003 (19)	0.0026 (19)
C12	0.017 (2)	0.019 (2)	0.017 (2)	0.0047 (18)	0.0018 (19)	0.004 (2)
C13	0.020 (2)	0.028 (3)	0.024 (3)	0.001 (2)	0.004 (2)	0.002 (2)
C14	0.025 (3)	0.041 (3)	0.024 (3)	0.001 (2)	0.012 (2)	0.009 (2)
C15	0.037 (3)	0.030 (3)	0.017 (2)	0.013 (2)	0.009 (2)	0.003 (2)
C16	0.033 (3)	0.021 (2)	0.015 (2)	0.001 (2)	−0.002 (2)	0.001 (2)
C17	0.024 (2)	0.012 (2)	0.017 (2)	0.0016 (18)	0.001 (2)	0.0013 (19)
C18	0.032 (3)	0.019 (2)	0.026 (3)	0.002 (2)	−0.009 (2)	0.000 (2)
C19	0.034 (3)	0.066 (4)	0.036 (3)	−0.020 (3)	0.004 (3)	−0.007 (3)

Geometric parameters (Å, º) top

U—O1	2.267 (3)	C9—C10	1.494 (9)
U—O2	2.233 (3)	C9—H9A	0.9900
U—O3	1.787 (3)	C9—H9B	0.9900
U—O4	1.792 (3)	C9'—C10'	1.493 (13)
U—O5	2.395 (3)	C9'—H9'A	0.9900
U—N1	2.547 (4)	C9'—H9'B	0.9900
U—N3	2.603 (4)	C10—H10A	0.9800
S1—C9	1.821 (6)	C10—H10B	0.9800
S1'—C9'	1.819 (12)	C10—H10C	0.9800
S2—O5	1.532 (3)	C10'—H10D	0.9800
S2—C18	1.773 (5)	C10'—H10E	0.9800
S2—C19	1.779 (6)	C10'—H10F	0.9800
O1—C1	1.316 (5)	C11—C12	1.440 (6)
O2—C17	1.310 (6)	C11—H11	0.9500
N1—C7	1.312 (5)	C12—C13	1.407 (7)
N1—N2'	1.415 (5)	C12—C17	1.419 (6)
N2—N3	1.402 (5)	C13—C14	1.377 (7)
N3—C11	1.292 (6)	C13—H13	0.9500
C1—C2	1.414 (6)	C14—C15	1.393 (7)
C1—C6	1.419 (6)	C14—H14	0.9500
C2—C3	1.379 (6)	C15—C16	1.373 (7)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.398 (6)	C16—C17	1.409 (6)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.358 (6)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.425 (6)	C18—H18C	0.9800
C5—H5	0.9500	C19—H19A	0.9800
C6—C7	1.437 (6)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800

O3—U—O4	177.84 (14)	S1—C9—H9A	108.7
O3—U—O2	94.71 (13)	C10—C9—H9B	108.7
O4—U—O2	87.36 (13)	S1—C9—H9B	108.7
O3—U—O1	89.60 (12)	H9A—C9—H9B	107.6
O4—U—O1	88.65 (12)	C10'—C9'—S1'	124 (2)
O2—U—O1	160.62 (11)	C10'—C9'—H9'A	106.4
O3—U—O5	89.31 (12)	S1'—C9'—H9'A	106.4
O4—U—O5	91.63 (12)	C10'—C9'—H9'B	106.4
O2—U—O5	81.36 (11)	S1'—C9'—H9'B	106.4
O1—U—O5	79.81 (11)	H9'A—C9'—H9'B	106.5
O3—U—N1	95.21 (13)	C9—C10—H10A	109.5
O4—U—N1	83.00 (12)	C9—C10—H10B	109.5
O2—U—N1	128.10 (12)	H10A—C10—H10B	109.5
O1—U—N1	70.05 (11)	C9—C10—H10C	109.5
O5—U—N1	149.45 (11)	H10A—C10—H10C	109.5
O3—U—N3	81.27 (12)	H10B—C10—H10C	109.5
O4—U—N3	98.90 (12)	C9'—C10'—H10D	109.5
O2—U—N3	69.45 (11)	C9'—C10'—H10E	109.5
O1—U—N3	129.92 (11)	H10D—C10'—H10E	109.5
O5—U—N3	148.30 (11)	C9'—C10'—H10F	109.5
N1—U—N3	62.04 (11)	H10D—C10'—H10F	109.5
O5—S2—C18	106.6 (2)	H10E—C10'—H10F	109.5
O5—S2—C19	105.3 (2)	N3—C11—C12	127.3 (4)
C18—S2—C19	98.3 (3)	N3—C11—H11	116.3
C1—O1—U	130.0 (3)	C12—C11—H11	116.3
C17—O2—U	142.8 (3)	C13—C12—C17	119.5 (4)
S2—O5—U	133.10 (18)	C13—C12—C11	117.6 (4)
C7—N1—N2'	116.1 (4)	C17—C12—C11	122.8 (4)
C7—N1—U	123.5 (3)	C14—C13—C12	121.2 (5)
N2'—N1—U	119.1 (3)	C14—C13—H13	119.4
C11—N3—N2	111.4 (4)	C12—C13—H13	119.4
C11—N3—U	128.4 (3)	C13—C14—C15	119.0 (5)
N2—N3—U	119.0 (3)	C13—C14—H14	120.5
O1—C1—C2	120.0 (4)	C15—C14—H14	120.5
O1—C1—C6	121.8 (4)	C16—C15—C14	121.4 (5)
C2—C1—C6	118.1 (4)	C16—C15—H15	119.3
C3—C2—C1	120.4 (4)	C14—C15—H15	119.3
C3—C2—H2	119.8	C15—C16—C17	120.8 (5)
C1—C2—H2	119.8	C15—C16—H16	119.6
C2—C3—C4	121.4 (4)	C17—C16—H16	119.6
C2—C3—H3	119.3	O2—C17—C16	120.7 (4)
C4—C3—H3	119.3	O2—C17—C12	121.2 (4)
C5—C4—C3	119.7 (4)	C16—C17—C12	118.1 (4)
C5—C4—H4	120.2	S2—C18—H18A	109.5
C3—C4—H4	120.2	S2—C18—H18B	109.5
C4—C5—C6	120.9 (4)	H18A—C18—H18B	109.5
C4—C5—H5	119.5	S2—C18—H18C	109.5
C6—C5—H5	119.5	H18A—C18—H18C	109.5
C5—C6—C1	119.5 (4)	H18B—C18—H18C	109.5
C5—C6—C7	117.3 (4)	S2—C19—H19A	109.5
C1—C6—C7	122.9 (4)	S2—C19—H19B	109.5
N1—C7—C6	126.2 (4)	H19A—C19—H19B	109.5
N1—C7—H7	116.9	S2—C19—H19C	109.5
C6—C7—H7	116.9	H19A—C19—H19C	109.5
C10—C9—S1	114.2 (4)	H19B—C19—H19C	109.5
C10—C9—H9A	108.7

O3—U—O1—C1	−149.9 (3)	O4—U—N3—N2	−89.6 (3)
O4—U—O1—C1	28.9 (3)	O2—U—N3—N2	−173.4 (3)
O2—U—O1—C1	107.0 (4)	O1—U—N3—N2	6.1 (3)
O5—U—O1—C1	120.8 (3)	O5—U—N3—N2	162.5 (3)
N1—U—O1—C1	−54.2 (3)	N1—U—N3—N2	−12.5 (3)
N3—U—O1—C1	−71.6 (4)	U—O1—C1—C2	−135.9 (3)
O3—U—O2—C17	43.8 (5)	U—O1—C1—C6	46.5 (5)
O4—U—O2—C17	−135.5 (5)	O1—C1—C2—C3	−177.2 (4)
O1—U—O2—C17	146.2 (4)	C6—C1—C2—C3	0.5 (6)
O5—U—O2—C17	132.4 (5)	C1—C2—C3—C4	0.4 (7)
N1—U—O2—C17	−56.6 (5)	C2—C3—C4—C5	0.1 (7)
N3—U—O2—C17	−35.0 (5)	C3—C4—C5—C6	−1.4 (7)
C18—S2—O5—U	−46.1 (3)	C4—C5—C6—C1	2.2 (7)
C19—S2—O5—U	57.7 (3)	C4—C5—C6—C7	175.9 (4)
O3—U—O5—S2	170.9 (3)	O1—C1—C6—C5	175.9 (4)
O4—U—O5—S2	−11.0 (3)	C2—C1—C6—C5	−1.7 (6)
O2—U—O5—S2	76.1 (3)	O1—C1—C6—C7	2.6 (6)
O1—U—O5—S2	−99.3 (3)	C2—C1—C6—C7	−175.1 (4)
N1—U—O5—S2	−90.0 (3)	N2'—N1—C7—C6	171.9 (4)
N3—U—O5—S2	98.9 (3)	U—N1—C7—C6	−21.1 (6)
O3—U—N1—C7	127.2 (3)	C5—C6—C7—N1	175.5 (4)
O4—U—N1—C7	−51.6 (3)	C1—C6—C7—N1	−11.0 (7)
O2—U—N1—C7	−132.7 (3)	N2—N3—C11—C12	−177.0 (4)
O1—U—N1—C7	39.5 (3)	U—N3—C11—C12	−9.7 (6)
O5—U—N1—C7	29.7 (4)	N3—C11—C12—C13	173.4 (4)
N3—U—N1—C7	−155.6 (4)	N3—C11—C12—C17	−6.6 (7)
O3—U—N1—N2'	−66.2 (3)	C17—C12—C13—C14	0.9 (7)
O4—U—N1—N2'	115.1 (3)	C11—C12—C13—C14	−179.2 (4)
O2—U—N1—N2'	34.0 (3)	C12—C13—C14—C15	−1.8 (7)
O1—U—N1—N2'	−153.8 (3)	C13—C14—C15—C16	0.7 (8)
O5—U—N1—N2'	−163.7 (3)	C14—C15—C16—C17	1.3 (7)
N3—U—N1—N2'	11.1 (3)	U—O2—C17—C16	−148.3 (4)
O3—U—N3—C11	−78.3 (4)	U—O2—C17—C12	32.4 (7)
O4—U—N3—C11	103.9 (4)	C15—C16—C17—O2	178.5 (4)
O2—U—N3—C11	20.1 (3)	C15—C16—C17—C12	−2.2 (7)
O1—U—N3—C11	−160.4 (3)	C13—C12—C17—O2	−179.6 (4)
O5—U—N3—C11	−4.1 (5)	C11—C12—C17—O2	0.4 (7)
N1—U—N3—C11	−179.0 (4)	C13—C12—C17—C16	1.1 (6)
O3—U—N3—N2	88.2 (3)	C11—C12—C17—C16	−178.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.95	2.48	3.322 (5)	147

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[U(C₁₇H₁₅N₃O₂S)O₂(C₂H₆OS)]
M_r	673.54
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.6988 (3), 15.4972 (3), 12.2246 (3)
β (°)	105.714 (3)
V (Å³)	2133.47 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.84
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.333, 0.508
No. of measured, independent and observed [I > 2σ(I)] reflections	19265, 4927, 4237
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.063, 1.01
No. of reflections	4927
No. of parameters	281
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −1.52

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

U—O1	2.267 (3)	U—O5	2.395 (3)
U—O2	2.233 (3)	U—N1	2.547 (4)
U—O3	1.787 (3)	U—N3	2.603 (4)
U—O4	1.792 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.95	2.48	3.322 (5)	147

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

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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