{4-Bromo-2-[(2-{(ethyl­sulfan­yl)[(2-oxidobenzyl­idene-κO)amino-κN]methylidene}hydrazinyl­idene-κN1)meth­yl]phenolato-κO}(butan-2-ol-κO)dioxidouranium(VI)

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

doi:10.1107/S1600536812005077

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m279-m280

doi:10.1107/S1600536812005077

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{4-Bromo-2-[(2-{(ethylsulfanyl)[(2-oxidobenzylidene-κO)amino-κN]methylidene}hydrazinylidene-κN¹)methyl]phenolato-κO}(butan-2-ol-κO)dioxidouranium(VI)

Reza Takjoo,^a ‡ Mehdi Ahmadi,^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 5 February 2012; accepted 5 February 2012; online 10 February 2012)

The U^VI cation in the title complex, [U(C₁₇H₁₄BrN₃O₂S)O₂(C₄H₁₀O)], exists within a distorted pentagonal–bipyramidal geometry, where the oxide atoms occupy the axial positions [O—U—O = 179.8 (3)°] and the pentagonal plane is defined by the N₂O₂ atoms of the tetradentate Schiff base ligand and the O atom of the 2-butanol molecule. In the crystal, centrosymmetric aggregates are formed via pairs of hydroxy–phenolate O—H⋯O hydrogen bonds. The azomethine C=N atoms, the ethylthiolyl group, the 2-butanol molecule and Br atom are disordered over two positions in a 0.627 (3):0.373 (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(C₁₇H₁₄BrN₃O₂)O₂(C₄H₁₀O)]
M_r = 748.43
Monoclinic, P 2₁ /c
a = 11.4795 (2) Å
b = 14.6450 (3) Å
c = 14.3383 (6) Å
β = 98.094 (3)°
V = 2386.50 (12) Å³
Z = 4
Mo Kα radiation
μ = 8.60 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.182, T_max = 0.673
17329 measured reflections
5495 independent reflections
4365 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.102
S = 1.18
5495 reflections
326 parameters
44 restraints
H-atom parameters constrained
Δρ_max = 1.58 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected bond lengths (Å)

U—O1	2.297 (6)
U—O2	2.232 (6)
U—O3	1.777 (5)
U—O4	1.777 (5)
U—O5	2.411 (5)
U—N1	2.572 (7)
U—N3	2.563 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5O⋯O1ⁱ	0.84	1.88	2.667 (8)	155
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/S1600536812005077/hb6627sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005077/hb6627Isup2.hkl

checkCIF report

Comment top

Recent studies of uranyl Schiff base complexes (Şahin et al., 2010) motivated the synthesis of the title complex, (I), in continuation of related structural 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 = 179.8 (3)°. The pentagonal plane is defined by the N₂O₂ atoms, derived from the tetradentate Schiff base ligand, and the O atom of the 2-butanol molecule, Table 1. The Schiff base ligand is somewhat twisted with the dihedral angle between the terminal benzene rings being 31.9 (4)°.

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 a, 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 ml) of 5-bromosalicylaldehyde mono-S-ethylisothiosemicarbazone hydrobromide (0.38 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 were isolated after four days, collected by filtration, washed with diethyl ether and dried in air. m.p. 493 K (dec,). Yield: 33%.

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 are 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 a axis of the unit-cell contents of (I).

{4-Bromo-2-[(2-{(ethylsulfanyl)[(2-oxidobenzylidene-κO)amino- κN]methylidene}hydrazinylidene-κN¹)methyl]phenolato- κO}(butan-2-ol-κO)dioxidouranium(VI) top

Crystal data top

[U(C₁₇H₁₄BrN₃O₂)O₂(C₄H₁₀O)]	F(000) = 1416
M_r = 748.43	D_x = 2.083 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5878 reflections
a = 11.4795 (2) Å	θ = 2.3–27.5°
b = 14.6450 (3) Å	µ = 8.60 mm⁻¹
c = 14.3383 (6) Å	T = 100 K
β = 98.094 (3)°	Prism, red
V = 2386.50 (12) Å³	0.30 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	5495 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4365 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→19
T_min = 0.182, T_max = 0.673	l = −14→18
17329 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0173P)² + 17.3449P] where P = (F_o² + 2F_c²)/3
5495 reflections	(Δ/σ)_max = 0.001
326 parameters	Δρ_max = 1.58 e Å⁻³
44 restraints	Δρ_min = −0.97 e Å⁻³

Crystal data top

[U(C₁₇H₁₄BrN₃O₂)O₂(C₄H₁₀O)]	V = 2386.50 (12) Å³
M_r = 748.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4795 (2) Å	µ = 8.60 mm⁻¹
b = 14.6450 (3) Å	T = 100 K
c = 14.3383 (6) Å	0.30 × 0.10 × 0.05 mm
β = 98.094 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	5495 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4365 reflections with I > 2σ(I)
T_min = 0.182, T_max = 0.673	R_int = 0.046
17329 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	44 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0173P)² + 17.3449P] where P = (F_o² + 2F_c²)/3
5495 reflections	Δρ_max = 1.58 e Å⁻³
326 parameters	Δρ_min = −0.97 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
U	0.71638 (2)	0.51761 (2)	0.61360 (2)	0.03255 (10)
Br1	0.89529 (14)	0.43057 (14)	0.11495 (12)	0.0647 (6)	0.627 (2)
Br1'	0.6959 (2)	0.67063 (17)	1.12727 (18)	0.0459 (8)	0.373 (2)
S1	1.0253 (4)	0.7635 (3)	0.7352 (4)	0.0648 (13)	0.627 (2)
S1'	1.0601 (4)	0.7180 (3)	0.5330 (4)	0.0285 (12)	0.373 (2)
O1	0.6612 (4)	0.5191 (4)	0.4533 (4)	0.0417 (14)
O2	0.7143 (5)	0.4871 (4)	0.7659 (4)	0.0395 (14)
O3	0.8190 (4)	0.4273 (3)	0.6093 (4)	0.0366 (14)
O4	0.6138 (4)	0.6079 (4)	0.6175 (4)	0.0364 (14)
O5	0.5534 (5)	0.4123 (4)	0.5981 (5)	0.0418 (15)	0.627 (2)
H5O	0.4914	0.4432	0.5965	0.063*	0.627 (2)
O5'	0.5534 (5)	0.4123 (4)	0.5981 (5)	0.0418 (15)	0.373
H5O'	0.4859	0.4304	0.5753	0.063*	0.627 (2)
N1	0.8701 (5)	0.6029 (4)	0.5323 (5)	0.0343 (16)
N2	0.9460 (6)	0.6668 (5)	0.5850 (5)	0.0363 (18)	0.627 (2)
C8'	0.9460 (6)	0.6668 (5)	0.5850 (5)	0.0363 (18)	0.373
N3	0.8540 (5)	0.6299 (4)	0.7120 (5)	0.0313 (15)
C1	0.7170 (7)	0.4970 (5)	0.3816 (6)	0.035 (2)
C2	0.6604 (7)	0.4462 (6)	0.3064 (7)	0.044 (2)
H2	0.5829	0.4243	0.3084	0.052*
C3	0.7155 (8)	0.4273 (6)	0.2288 (7)	0.045 (2)
H3	0.6757	0.3928	0.1779	0.054*
C4	0.8294 (8)	0.4590 (7)	0.2250 (7)	0.053 (3)
H4	0.8670	0.4466	0.1714	0.063*	0.373 (2)
C5	0.8863 (7)	0.5075 (6)	0.2985 (6)	0.042 (2)
H5	0.9641	0.5281	0.2955	0.050*
C6	0.8338 (6)	0.5282 (5)	0.3788 (6)	0.0344 (18)
C7	0.8987 (7)	0.5843 (5)	0.4495 (6)	0.0344 (19)
H7	0.9695	0.6106	0.4347	0.041*
C8	0.9367 (6)	0.6810 (5)	0.6703 (6)	0.0336 (18)	0.627 (2)
N2'	0.9367 (6)	0.6810 (5)	0.6703 (6)	0.0336 (18)	0.373
C9	1.0718 (19)	0.8414 (15)	0.6368 (19)	0.080 (6)	0.627 (2)
H9A	1.0115	0.8464	0.5804	0.097*	0.627 (2)
H9B	1.1000	0.9025	0.6594	0.097*	0.627 (2)
C10	1.160 (2)	0.7813 (18)	0.626 (2)	0.114 (9)	0.627 (2)
H10A	1.2025	0.8020	0.5755	0.171*	0.627 (2)
H10B	1.1268	0.7207	0.6111	0.171*	0.627 (2)
H10C	1.2151	0.7780	0.6854	0.171*	0.627 (2)
C9'	1.116 (3)	0.800 (2)	0.636 (3)	0.080 (6)	0.373
H9'A	1.0956	0.7773	0.6966	0.097*	0.373 (2)
H9'B	1.2028	0.8082	0.6420	0.097*	0.373 (2)
C10'	1.059 (4)	0.881 (3)	0.610 (4)	0.114 (9)	0.373
H10D	1.0978	0.9311	0.6466	0.171*	0.373 (2)
H10E	0.9769	0.8762	0.6223	0.171*	0.373 (2)
H10F	1.0598	0.8915	0.5428	0.171*	0.373 (2)
C11	0.8440 (7)	0.6554 (6)	0.7987 (6)	0.038 (2)
H11	0.8901	0.7066	0.8219	0.046*
C12	0.7717 (7)	0.6153 (6)	0.8632 (6)	0.039 (2)
C13	0.7703 (8)	0.6596 (7)	0.9479 (7)	0.051 (2)
H13	0.8141	0.7144	0.9605	0.061*
C14	0.7061 (8)	0.6254 (8)	1.0150 (7)	0.053 (3)
H14	0.7045	0.6568	1.0728	0.064*	0.373 (2)
C15	0.6442 (8)	0.5449 (8)	0.9963 (7)	0.058 (3)
H15	0.6004	0.5208	1.0421	0.069*
C16	0.6451 (7)	0.4991 (7)	0.9129 (7)	0.047 (2)
H16	0.6016	0.4441	0.9015	0.056*
C17	0.7098 (6)	0.5329 (5)	0.8440 (6)	0.0345 (19)
C18	0.6029 (13)	0.2716 (10)	0.5306 (11)	0.057 (4)	0.627 (2)
H18A	0.6122	0.3110	0.4769	0.085*	0.627 (2)
H18B	0.5703	0.2126	0.5075	0.085*	0.627 (2)
H18C	0.6797	0.2621	0.5687	0.085*	0.627 (2)
C19	0.5196 (13)	0.3168 (7)	0.5904 (9)	0.056 (4)	0.627 (2)
H19	0.4394	0.3146	0.5528	0.067*	0.627 (2)
C20	0.512 (2)	0.2656 (13)	0.6807 (13)	0.100 (7)	0.627 (2)
H20A	0.5924	0.2567	0.7149	0.120*	0.627 (2)
H20B	0.4775	0.2045	0.6654	0.120*	0.627 (2)
C21	0.4374 (14)	0.3160 (11)	0.7449 (10)	0.062 (4)	0.627 (2)
H21A	0.4268	0.2770	0.7986	0.093*	0.627 (2)
H21B	0.3604	0.3306	0.7093	0.093*	0.627 (2)
H21C	0.4772	0.3725	0.7677	0.093*	0.627 (2)
C18'	0.484 (2)	0.2953 (18)	0.6972 (18)	0.057 (4)	0.373
H18D	0.4965	0.3373	0.7510	0.085*	0.373 (2)
H18E	0.4957	0.2324	0.7196	0.085*	0.373 (2)
H18F	0.4028	0.3023	0.6652	0.085*	0.373 (2)
C19'	0.5709 (19)	0.3176 (9)	0.6280 (14)	0.056 (4)	0.373
H19'	0.6532	0.3094	0.6604	0.067*	0.373 (2)
C20'	0.548 (3)	0.252 (2)	0.544 (2)	0.100 (7)	0.373
H20C	0.5547	0.1880	0.5668	0.120*	0.373 (2)
H20D	0.4678	0.2613	0.5104	0.120*	0.373 (2)
C21'	0.638 (2)	0.269 (2)	0.4770 (17)	0.062 (4)	0.373
H21D	0.6245	0.2264	0.4239	0.093*	0.373 (2)
H21E	0.7179	0.2598	0.5107	0.093*	0.373 (2)
H21F	0.6304	0.3318	0.4534	0.093*	0.373 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
U	0.01734 (14)	0.03167 (16)	0.0468 (2)	−0.00210 (12)	−0.00192 (11)	−0.00001 (15)
Br1	0.0434 (9)	0.1021 (14)	0.0438 (10)	0.0328 (9)	−0.0099 (7)	−0.0256 (9)
Br1'	0.0460 (15)	0.0473 (15)	0.0454 (16)	−0.0007 (11)	0.0102 (11)	−0.0049 (11)
S1	0.049 (2)	0.067 (3)	0.082 (4)	−0.024 (2)	0.020 (2)	−0.025 (2)
S1'	0.022 (2)	0.035 (3)	0.031 (3)	−0.016 (2)	0.012 (2)	−0.010 (2)
O1	0.022 (3)	0.052 (4)	0.048 (4)	−0.005 (3)	−0.003 (3)	−0.005 (3)
O2	0.029 (3)	0.043 (3)	0.046 (4)	−0.005 (3)	0.002 (3)	0.003 (3)
O3	0.022 (3)	0.030 (3)	0.058 (4)	0.004 (2)	0.006 (3)	−0.003 (3)
O4	0.017 (2)	0.033 (3)	0.059 (4)	0.001 (2)	0.002 (2)	0.004 (3)
O5	0.026 (3)	0.030 (3)	0.068 (5)	−0.006 (2)	0.001 (3)	0.005 (3)
O5'	0.026 (3)	0.030 (3)	0.068 (5)	−0.006 (2)	0.001 (3)	0.005 (3)
N1	0.022 (3)	0.032 (4)	0.045 (5)	−0.007 (3)	−0.005 (3)	0.000 (3)
N2	0.025 (4)	0.036 (4)	0.047 (5)	−0.007 (3)	0.005 (3)	−0.010 (3)
C8'	0.025 (4)	0.036 (4)	0.047 (5)	−0.007 (3)	0.005 (3)	−0.010 (3)
N3	0.019 (3)	0.035 (4)	0.038 (4)	−0.004 (3)	−0.003 (3)	−0.003 (3)
C1	0.024 (4)	0.029 (5)	0.049 (5)	−0.002 (3)	−0.007 (4)	0.005 (4)
C2	0.031 (4)	0.043 (5)	0.054 (6)	−0.002 (4)	−0.006 (4)	0.001 (4)
C3	0.043 (5)	0.043 (5)	0.044 (6)	−0.001 (4)	−0.008 (4)	−0.001 (4)
C4	0.050 (6)	0.067 (7)	0.038 (6)	0.013 (5)	−0.007 (4)	−0.015 (5)
C5	0.029 (4)	0.048 (5)	0.046 (5)	0.006 (4)	−0.003 (4)	0.005 (4)
C6	0.022 (4)	0.037 (5)	0.041 (5)	−0.001 (3)	−0.003 (3)	−0.001 (4)
C7	0.021 (4)	0.042 (5)	0.038 (5)	−0.002 (3)	−0.002 (3)	0.002 (4)
C8	0.025 (4)	0.029 (4)	0.046 (5)	−0.010 (3)	0.002 (3)	−0.010 (3)
N2'	0.025 (4)	0.029 (4)	0.046 (5)	−0.010 (3)	0.002 (3)	−0.010 (3)
C9	0.061 (9)	0.090 (10)	0.091 (9)	−0.046 (8)	0.010 (7)	0.001 (8)
C10	0.116 (12)	0.091 (11)	0.128 (12)	−0.017 (9)	−0.011 (9)	0.009 (8)
C9'	0.061 (9)	0.090 (10)	0.091 (9)	−0.046 (8)	0.010 (7)	0.001 (8)
C10'	0.116 (12)	0.091 (11)	0.128 (12)	−0.017 (9)	−0.011 (9)	0.009 (8)
C11	0.023 (4)	0.047 (5)	0.043 (6)	−0.005 (4)	0.001 (4)	−0.006 (4)
C12	0.023 (4)	0.044 (5)	0.046 (6)	−0.001 (4)	−0.005 (4)	−0.004 (4)
C13	0.031 (5)	0.070 (7)	0.051 (7)	−0.005 (4)	0.003 (4)	−0.008 (5)
C14	0.038 (5)	0.092 (8)	0.032 (6)	−0.001 (5)	0.010 (4)	−0.001 (5)
C15	0.028 (5)	0.103 (9)	0.041 (6)	−0.007 (5)	0.004 (4)	0.019 (6)
C16	0.028 (4)	0.066 (7)	0.044 (6)	−0.001 (4)	−0.002 (4)	0.011 (5)
C17	0.020 (4)	0.040 (5)	0.043 (5)	0.005 (3)	0.000 (3)	0.006 (4)
C18	0.046 (9)	0.033 (7)	0.089 (13)	−0.008 (6)	0.005 (8)	0.027 (8)
C19	0.061 (8)	0.047 (6)	0.057 (8)	−0.005 (6)	0.000 (6)	0.003 (6)
C20	0.102 (11)	0.091 (10)	0.108 (11)	0.013 (8)	0.016 (8)	0.005 (8)
C21	0.061 (7)	0.062 (7)	0.063 (8)	−0.009 (6)	0.009 (6)	0.012 (6)
C18'	0.046 (9)	0.033 (7)	0.089 (13)	−0.008 (6)	0.005 (8)	0.027 (8)
C19'	0.061 (8)	0.047 (6)	0.057 (8)	−0.005 (6)	0.000 (6)	0.003 (6)
C20'	0.102 (11)	0.091 (10)	0.108 (11)	0.013 (8)	0.016 (8)	0.005 (8)
C21'	0.061 (7)	0.062 (7)	0.063 (8)	−0.009 (6)	0.009 (6)	0.012 (6)

Geometric parameters (Å, º) top

U—O1	2.297 (6)	C9'—H9'B	0.9900
U—O2	2.232 (6)	C10'—H10D	0.9800
U—O3	1.777 (5)	C10'—H10E	0.9800
U—O4	1.777 (5)	C10'—H10F	0.9800
U—O5	2.411 (5)	C11—C12	1.451 (12)
U—N1	2.572 (7)	C11—H11	0.9500
U—N3	2.563 (6)	C12—C13	1.380 (13)
Br1—C4	1.889 (10)	C12—C17	1.408 (11)
Br1'—C14	1.760 (10)	C13—C14	1.384 (13)
S1—C8	1.759 (7)	C13—H13	0.9500
S1—C9	1.95 (2)	C14—C15	1.383 (14)
S1'—C9'	1.94 (2)	C14—H14	0.9500
O1—C1	1.324 (10)	C15—C16	1.373 (14)
O2—C17	1.313 (10)	C15—H15	0.9500
O5—C19	1.452 (12)	C16—C17	1.406 (12)
O5—H5O	0.8400	C16—H16	0.9500
N1—C7	1.304 (10)	C18—C19	1.522 (9)
N1—N2	1.421 (9)	C18—H18A	0.9800
N2—C8	1.261 (10)	C18—H18B	0.9800
N3—C11	1.317 (10)	C18—H18C	0.9800
N3—C8	1.406 (9)	C19—C20	1.510 (9)
C1—C2	1.394 (12)	C19—H19	1.0000
C1—C6	1.423 (10)	C20—C21	1.532 (9)
C2—C3	1.383 (13)	C20—H20A	0.9900
C2—H2	0.9500	C20—H20B	0.9900
C3—C4	1.396 (13)	C21—H21A	0.9800
C3—H3	0.9500	C21—H21B	0.9800
C4—C5	1.359 (12)	C21—H21C	0.9800
C4—H4	0.9500	C18'—C19'	1.542 (10)
C5—C6	1.406 (12)	C18'—H18D	0.9800
C5—H5	0.9500	C18'—H18E	0.9800
C6—C7	1.430 (11)	C18'—H18F	0.9800
C7—H7	0.9500	C19'—C20'	1.535 (10)
C9—C10	1.37 (3)	C19'—H19'	1.0000
C9—H9A	0.9900	C20'—C21'	1.528 (10)
C9—H9B	0.9900	C20'—H20C	0.9900
C10—H10A	0.9800	C20'—H20D	0.9900
C10—H10B	0.9800	C21'—H21D	0.9800
C10—H10C	0.9800	C21'—H21E	0.9800
C9'—C10'	1.38 (3)	C21'—H21F	0.9800
C9'—H9'A	0.9900

O3—U—O4	179.8 (3)	S1'—C9'—H9'B	111.1
O3—U—O2	89.0 (2)	H9'A—C9'—H9'B	109.1
O4—U—O2	91.1 (2)	C9'—C10'—H10D	109.5
O3—U—O1	93.6 (2)	C9'—C10'—H10E	109.5
O4—U—O1	86.2 (2)	H10D—C10'—H10E	109.5
O2—U—O1	160.29 (19)	C9'—C10'—H10F	109.5
O3—U—O5	91.8 (2)	H10D—C10'—H10F	109.5
O4—U—O5	88.3 (2)	H10E—C10'—H10F	109.5
O2—U—O5	81.2 (2)	N3—C11—C12	128.3 (8)
O1—U—O5	79.2 (2)	N3—C11—H11	115.8
O3—U—N3	97.8 (2)	C12—C11—H11	115.8
O4—U—N3	82.2 (2)	C13—C12—C17	120.5 (9)
O2—U—N3	71.4 (2)	C13—C12—C11	116.7 (8)
O1—U—N3	127.4 (2)	C17—C12—C11	122.7 (8)
O5—U—N3	150.7 (2)	C12—C13—C14	121.0 (10)
O3—U—N1	81.1 (2)	C12—C13—H13	119.5
O4—U—N1	98.8 (2)	C14—C13—H13	119.5
O2—U—N1	130.0 (2)	C15—C14—C13	118.9 (10)
O1—U—N1	69.6 (2)	C15—C14—Br1'	113.5 (8)
O5—U—N1	147.4 (2)	C13—C14—Br1'	127.6 (9)
N3—U—N1	61.9 (2)	C15—C14—H14	120.6
C8—S1—C9	102.5 (8)	C13—C14—H14	120.6
C1—O1—U	132.8 (5)	C16—C15—C14	121.2 (9)
C17—O2—U	137.6 (5)	C16—C15—H15	119.4
C19—O5—U	145.0 (7)	C14—C15—H15	119.4
C19—O5—H5O	107.5	C15—C16—C17	120.7 (9)
U—O5—H5O	107.5	C15—C16—H16	119.7
C7—N1—N2	114.0 (6)	C17—C16—H16	119.7
C7—N1—U	126.0 (5)	O2—C17—C16	120.5 (8)
N2—N1—U	119.2 (5)	O2—C17—C12	121.7 (8)
C8—N2—N1	119.7 (6)	C16—C17—C12	117.8 (9)
C11—N3—C8	113.8 (6)	C19—C18—H18A	109.5
C11—N3—U	124.9 (5)	C19—C18—H18B	109.5
C8—N3—U	120.5 (5)	H18A—C18—H18B	109.5
O1—C1—C2	120.5 (7)	C19—C18—H18C	109.5
O1—C1—C6	120.2 (7)	H18A—C18—H18C	109.5
C2—C1—C6	119.2 (8)	H18B—C18—H18C	109.5
C3—C2—C1	120.9 (8)	O5—C19—C20	117.4 (13)
C3—C2—H2	119.6	O5—C19—C18	106.2 (10)
C1—C2—H2	119.6	C20—C19—C18	112.6 (8)
C2—C3—C4	120.1 (8)	O5—C19—H19	106.7
C2—C3—H3	119.9	C20—C19—H19	106.7
C4—C3—H3	119.9	C18—C19—H19	106.7
C5—C4—C3	119.6 (9)	C19—C20—C21	112.4 (9)
C5—C4—Br1	123.9 (8)	C19—C20—H20A	109.1
C3—C4—Br1	116.5 (7)	C21—C20—H20A	109.1
C5—C4—H4	120.2	C19—C20—H20B	109.1
C3—C4—H4	120.2	C21—C20—H20B	109.1
C4—C5—C6	122.3 (8)	H20A—C20—H20B	107.9
C4—C5—H5	118.9	C20—C21—H21A	109.5
C6—C5—H5	118.9	C20—C21—H21B	109.5
C5—C6—C1	117.9 (8)	H21A—C21—H21B	109.5
C5—C6—C7	117.6 (7)	C20—C21—H21C	109.5
C1—C6—C7	124.3 (8)	H21A—C21—H21C	109.5
N1—C7—C6	126.3 (7)	H21B—C21—H21C	109.5
N1—C7—H7	116.8	C19'—C18'—H18D	109.5
C6—C7—H7	116.8	C19'—C18'—H18E	109.5
N2—C8—N3	118.7 (6)	H18D—C18'—H18E	109.5
N2—C8—S1	120.3 (6)	C19'—C18'—H18F	109.5
N3—C8—S1	121.0 (6)	H18D—C18'—H18F	109.5
C10—C9—S1	89.2 (18)	H18E—C18'—H18F	109.5
C10—C9—H9A	113.8	C20'—C19'—C18'	108.6 (9)
S1—C9—H9A	113.8	C20'—C19'—H19'	109.5
C10—C9—H9B	113.8	C18'—C19'—H19'	109.5
S1—C9—H9B	113.8	C21'—C20'—C19'	109.6 (10)
H9A—C9—H9B	111.0	C21'—C20'—H20C	109.7
C9—C10—H10A	109.5	C19'—C20'—H20C	109.7
C9—C10—H10B	109.5	C21'—C20'—H20D	109.7
H10A—C10—H10B	109.5	C19'—C20'—H20D	109.7
C9—C10—H10C	109.5	H20C—C20'—H20D	108.2
H10A—C10—H10C	109.5	C20'—C21'—H21D	109.5
H10B—C10—H10C	109.5	C20'—C21'—H21E	109.5
C10'—C9'—S1'	103 (3)	H21D—C21'—H21E	109.5
C10'—C9'—H9'A	111.1	C20'—C21'—H21F	109.5
S1'—C9'—H9'A	111.1	H21D—C21'—H21F	109.5
C10'—C9'—H9'B	111.1	H21E—C21'—H21F	109.5

O3—U—O1—C1	−28.2 (7)	C1—C2—C3—C4	0.2 (13)
O4—U—O1—C1	151.8 (7)	C2—C3—C4—C5	0.7 (14)
O2—U—O1—C1	−125.4 (7)	C2—C3—C4—Br1	−179.2 (7)
O5—U—O1—C1	−119.3 (7)	C3—C4—C5—C6	−0.7 (14)
N3—U—O1—C1	74.5 (7)	Br1—C4—C5—C6	179.2 (7)
N1—U—O1—C1	50.9 (6)	C4—C5—C6—C1	−0.3 (13)
O3—U—O2—C17	141.6 (7)	C4—C5—C6—C7	−176.3 (8)
O4—U—O2—C17	−38.4 (7)	O1—C1—C6—C5	−176.2 (7)
O1—U—O2—C17	−120.3 (8)	C2—C1—C6—C5	1.1 (11)
O5—U—O2—C17	−126.4 (7)	O1—C1—C6—C7	−0.4 (12)
N3—U—O2—C17	43.0 (7)	C2—C1—C6—C7	176.9 (8)
N1—U—O2—C17	64.1 (8)	N2—N1—C7—C6	−175.0 (7)
O3—U—O5—C19	2.1 (11)	U—N1—C7—C6	15.4 (11)
O4—U—O5—C19	−178.1 (11)	C5—C6—C7—N1	−172.5 (8)
O2—U—O5—C19	−86.7 (11)	C1—C6—C7—N1	11.7 (13)
O1—U—O5—C19	95.4 (11)	N1—N2—C8—N3	2.6 (11)
N3—U—O5—C19	−107.4 (11)	N1—N2—C8—S1	−177.1 (6)
N1—U—O5—C19	78.2 (12)	C11—N3—C8—N2	−174.4 (7)
O3—U—N1—C7	64.1 (6)	U—N3—C8—N2	−3.8 (9)
O4—U—N1—C7	−115.8 (6)	C11—N3—C8—S1	5.3 (9)
O2—U—N1—C7	145.3 (6)	U—N3—C8—S1	175.9 (4)
O1—U—N1—C7	−33.1 (6)	C9—S1—C8—N2	21.2 (11)
O5—U—N1—C7	−15.1 (8)	C9—S1—C8—N3	−158.5 (9)
N3—U—N1—C7	168.0 (7)	C8—S1—C9—C10	−83.3 (15)
O3—U—N1—N2	−105.0 (5)	C8—N3—C11—C12	−177.0 (8)
O4—U—N1—N2	75.1 (5)	U—N3—C11—C12	12.8 (12)
O2—U—N1—N2	−23.8 (6)	N3—C11—C12—C13	−175.1 (8)
O1—U—N1—N2	157.8 (6)	N3—C11—C12—C17	8.0 (13)
O5—U—N1—N2	175.8 (4)	C17—C12—C13—C14	−1.6 (13)
N3—U—N1—N2	−1.1 (5)	C11—C12—C13—C14	−178.5 (8)
C7—N1—N2—C8	−170.7 (7)	C12—C13—C14—C15	1.0 (14)
U—N1—N2—C8	−0.3 (9)	C12—C13—C14—Br1'	178.6 (7)
O3—U—N3—C11	−112.5 (7)	C13—C14—C15—C16	−0.4 (15)
O4—U—N3—C11	67.6 (7)	Br1'—C14—C15—C16	−178.3 (7)
O2—U—N3—C11	−26.2 (6)	C14—C15—C16—C17	0.3 (14)
O1—U—N3—C11	146.8 (6)	U—O2—C17—C16	142.7 (6)
O5—U—N3—C11	−4.6 (9)	U—O2—C17—C12	−39.3 (11)
N1—U—N3—C11	172.0 (7)	C15—C16—C17—O2	177.2 (8)
O3—U—N3—C8	77.9 (6)	C15—C16—C17—C12	−0.9 (12)
O4—U—N3—C8	−102.0 (5)	C13—C12—C17—O2	−176.6 (8)
O2—U—N3—C8	164.2 (6)	C11—C12—C17—O2	0.1 (12)
O1—U—N3—C8	−22.8 (6)	C13—C12—C17—C16	1.5 (12)
O5—U—N3—C8	−174.2 (5)	C11—C12—C17—C16	178.2 (7)
N1—U—N3—C8	2.4 (5)	U—O5—C19—C20	89.9 (15)
U—O1—C1—C2	136.4 (7)	U—O5—C19—C18	−37.1 (16)
U—O1—C1—C6	−46.3 (10)	O5—C19—C20—C21	51 (2)
O1—C1—C2—C3	176.2 (8)	C18—C19—C20—C21	174.6 (17)
C6—C1—C2—C3	−1.1 (12)	C18'—C19'—C20'—C21'	−177 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O1ⁱ	0.84	1.88	2.667 (8)	155

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[U(C₁₇H₁₄BrN₃O₂)O₂(C₄H₁₀O)]
M_r	748.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.4795 (2), 14.6450 (3), 14.3383 (6)
β (°)	98.094 (3)
V (Å³)	2386.50 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.60
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.182, 0.673
No. of measured, independent and observed [I > 2σ(I)] reflections	17329, 5495, 4365
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.102, 1.18
No. of reflections	5495
No. of parameters	326
No. of restraints	44
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0173P)² + 17.3449P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.58, −0.97

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	2.297 (6)	U—O5	2.411 (5)
U—O2	2.232 (6)	U—N1	2.572 (7)
U—O3	1.777 (5)	U—N3	2.563 (6)
U—O4	1.777 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O1ⁱ	0.84	1.88	2.667 (8)	155

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

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

Acknowledgements

The authors 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 (grant No. UM.C/HIR/MOHE/SC/12).

References

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Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. 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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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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