{4-Bromo-2-[(2-{(ethyl-sulfan-yl)[(2-oxidobenzyl-idene-κO)amino-κN]methylidene}hydrazinyl-idene-κN)meth-yl]phenolato-κO}(butan-2-ol-κO)dioxidouranium(VI).

The U(VI) cation in the title complex, [U(C(17)H(14)BrN(3)O(2)S)O(2)(C(4)H(10)O)], exists within a distorted penta-gonal-bipyramidal geometry, where the oxide atoms occupy the axial positions [O-U-O = 179.8 (3)°] and the penta-gonal plane is defined by the N(2)O(2) atoms of the tetra-dentate Schiff base ligand and the O atom of the 2-butanol mol-ecule. In the crystal, centrosymmetric aggregates are formed via pairs of hy-droxy-phenolate O-H⋯O hydrogen bonds. The azomethine C=N atoms, the ethyl-thiolyl group, the 2-butanol mol-ecule 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 = 748.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.102

S = 1.18

5495 reflections

326 parameters

44 restraints

H-atom parameters constrained

Δρmax = 1.58 e Å−3

Δρmin = −0.97 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005077/hb6627sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[U(C17H14BrN3O2)O2(C4H10O)]	F(000) = 1416
Mr = 748.43	Dx = 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

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	Rint = 0.046
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→19
Tmin = 0.182, Tmax = 0.673	l = −14→18
17329 measured reflections

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(Fo2) + (0.0173P)2 + 17.3449P] where P = (Fo2 + 2Fc2)/3
5495 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 1.58 e Å−3
44 restraints	Δρmin = −0.97 e Å−3

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) .