(Butan-2-ol-κO)[2-({(ethyl-sulfan-yl)[2-(2-oxidobenzyl-idene-κO)hydrazinyl-idene-κN]meth-yl}imino-meth-yl)phenolato-κO]dioxidouranium(VI).

The U atom in the title complex, [U(C(17)H(15)N(3)O(2)S)O(2)(C(4)H(10)O)], exists within a distorted penta-gonal-bipyramidal geometry where the oxide O atoms occupy axial positions [O-U-O = 179.61 (18)°] 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 butan-2-ol mol-ecule. In the crystal, centrosymmetric aggregates are formed via pairs of hy-droxy-phenoxide O-H⋯O hydrogen bonds. The azomethine C=N atoms, the ethyl-thiolyl group and the butyl group of the butan-2-ol mol-ecule 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 = 669.53

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.078

S = 1.16

5262 reflections

302 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.16 e Å−3

Δρmin = −0.81 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/S160053681200431X/hb6617sup1.cif

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

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

[U(C17H15N3O2S)O2(C4H10O)]	F(000) = 1280
Mr = 669.53	Dx = 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

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	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −18→18
Tmin = 0.265, Tmax = 0.713	l = −18→12
15878 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)] = 0.038	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(Fo2) + (0.0199P)2 + 8.1201P] where P = (Fo2 + 2Fc2)/3
5262 reflections	(Δ/σ)max = 0.001
302 parameters	Δρmax = 1.16 e Å−3
8 restraints	Δρmin = −0.81 e Å−3

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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)

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) .