[S-Allyl-4-(4-hy-droxy-2-oxidobenzyl-idene-κO)-1-(2-oxidobenzyl-idene-κO)isothio-semicarbazidato-κN,N](ethanol-κO)dioxido-uranium(VI) ethanol monosolvate.

In the title compound, [U(C(18)H(15)N(3)O(3)S)O(2)(C(2)H(5)OH)]·C(2)H(5)OH, the U(VI) ion is in a distorted penta-gonal-bipyramidal coordination geometry, with two oxide O atoms in axial sites. Two N and two O atoms of the tetra-dentate ligand and an O atom of an ethanol ligand form the equatorial plane. The dihedral angle between the mean planes of the two benzene rings is 34.8 (3)°. In the crystal, relatively strong O-H⋯O hydrogen bonds connect the complex and ethanol solvent mol-ecules into alternating centrosymmetric R(2) (2)(8) and R(4) (4)(16) ring motifs, forming chains along [100]. Weak inter-molecular C-H⋯O hydrogen bonds are also present.

Related literature

For background information on salicyl­aldehyde-S-alkyl-thio­semicarbazone compounds, see: Gerbeleu & Revenko (1971 ▶); Revenko et al. (1986 ▶); Simonov et al. (1985 ▶); Yampol’skaya et al. (1982 ▶, 1983 ▶). For a related structure, see: Kawasaki & Kitazawa (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[U(C18H15N3O3S)O2(C2H6O)]·C2H6O

M = 715.56

Monoclinic,

a = 12.0152 (4) Å

b = 17.6609 (4) Å

c = 13.1076 (3) Å

β = 109.195 (3)°

V = 2626.79 (12) Å3

Z = 4

Mo Kα radiation

μ = 6.30 mm−1

T = 100 K

0.20 × 0.12 × 0.10 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.424, T max = 1.000

11844 measured reflections

5467 independent reflections

4148 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.01

5467 reflections

309 parameters

1 restraint

H-atom parameters constrained

Δρmax = 2.48 e Å−3

Δρmin = −1.18 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811049579/lh5378sup1.cif

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

[U(C18H15N3O3S)O2(C2H6O)]·C2H6O	F(000) = 1376
Mr = 715.56	Dx = 1.809 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4645 reflections
a = 12.0152 (4) Å	θ = 2.8–28.2°
b = 17.6609 (4) Å	µ = 6.30 mm−1
c = 13.1076 (3) Å	T = 100 K
β = 109.195 (3)°	Block, red
V = 2626.79 (12) Å3	0.2 × 0.12 × 0.1 mm
Z = 4

Agilent Xcalibur Eos diffractometer	5467 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4148 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.1544 pixels mm-1	θmax = 28.3°, θmin = 2.9°
ω–scan	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −22→21
Tmin = 0.424, Tmax = 1.000	l = −16→16
11844 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.070P)2 + 2.0206P] where P = (Fo2 + 2Fc2)/3
5467 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 2.48 e Å−3
1 restraint	Δρmin = −1.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
U1	0.85612 (2)	0.123346 (13)	−0.019954 (19)	0.02921 (11)
O2	0.7621 (4)	0.1424 (3)	−0.1531 (4)	0.0344 (11)
O3	0.9470 (4)	0.1011 (3)	0.1138 (4)	0.0347 (11)
O4	0.8352 (4)	−0.0092 (2)	−0.0602 (4)	0.0310 (10)
H4	0.8855	−0.0413	−0.0219	0.037*
C5	0.7523 (9)	−0.0468 (5)	−0.1482 (8)	0.084 (4)
H5A	0.7917	−0.0624	−0.2003	0.101*
H5B	0.6887	−0.0108	−0.1856	0.101*
C6	0.6985 (12)	−0.1151 (6)	−0.1151 (12)	0.122 (7)
H6A	0.7606	−0.1518	−0.0801	0.183*
H6B	0.6417	−0.1383	−0.1790	0.183*
H6C	0.6581	−0.1000	−0.0644	0.183*
C7	1.0608 (6)	0.1338 (4)	−0.1445 (6)	0.0354 (17)
O8	1.0218 (5)	0.1062 (3)	−0.0663 (4)	0.0356 (11)
C9	1.1165 (6)	0.0868 (4)	−0.1974 (6)	0.0384 (17)
H9	1.1250	0.0344	−0.1804	0.046*
C10	1.1594 (7)	0.1156 (4)	−0.2739 (7)	0.0441 (19)
H10	1.1980	0.0828	−0.3090	0.053*
C11	1.1473 (7)	0.1928 (5)	−0.3016 (6)	0.048 (2)
H11	1.1760	0.2120	−0.3560	0.057*
C12	1.0942 (7)	0.2394 (4)	−0.2495 (6)	0.0431 (19)
H12	1.0883	0.2918	−0.2666	0.052*
C13	1.0469 (6)	0.2121 (4)	−0.1696 (6)	0.0379 (17)
C14	0.9981 (6)	0.2648 (4)	−0.1165 (6)	0.0397 (18)
H14	1.0081	0.3165	−0.1315	0.048*
N15	0.9399 (5)	0.2520 (3)	−0.0483 (5)	0.0397 (15)
N16	0.9061 (6)	0.3185 (4)	−0.0119 (6)	0.0482 (17)
C17	0.8425 (7)	0.3098 (4)	0.0480 (6)	0.0363 (17)
S18	0.7961 (2)	0.39101 (11)	0.09995 (18)	0.0496 (5)
C19	0.8632 (9)	0.4648 (4)	0.0437 (8)	0.059 (2)
H19A	0.9477	0.4536	0.0582	0.070*
H19B	0.8241	0.4678	−0.0355	0.070*
C20	0.8496 (9)	0.5379 (5)	0.0953 (8)	0.057 (2)
H20	0.9020	0.5486	0.1658	0.068*
C21	0.7689 (9)	0.5878 (5)	0.0483 (8)	0.065 (3)
H21A	0.7155	0.5784	−0.0222	0.078*
H21B	0.7637	0.6336	0.0844	0.078*
N22	0.8004 (5)	0.2383 (3)	0.0693 (5)	0.0353 (14)
C23	0.7552 (6)	0.2332 (4)	0.1475 (6)	0.0395 (18)
H23	0.7568	0.2779	0.1883	0.047*
C24	0.7047 (7)	0.1687 (5)	0.1774 (6)	0.0411 (18)
C25	0.6751 (6)	0.1012 (4)	0.1140 (6)	0.0337 (16)
O26	0.6906 (4)	0.0979 (3)	0.0188 (4)	0.0325 (11)
C27	0.6239 (7)	0.0409 (4)	0.1483 (6)	0.0379 (17)
H27	0.6041	−0.0036	0.1056	0.046*
C28	0.6012 (7)	0.0454 (4)	0.2465 (6)	0.0431 (19)
O29	0.5576 (5)	−0.0114 (4)	0.2859 (5)	0.0623 (17)
H29	0.5365	−0.0487	0.2416	0.075*
C30	0.6283 (8)	0.1125 (5)	0.3084 (7)	0.054 (2)
H30	0.6127	0.1160	0.3747	0.065*
C31	0.6763 (7)	0.1708 (5)	0.2730 (6)	0.0443 (19)
H31	0.6919	0.2160	0.3146	0.053*
O1S	0.5141 (6)	−0.1238 (3)	0.1448 (6)	0.0641 (18)
H1S1	0.4504	−0.1215	0.0902	0.077*
C2S	0.5324 (11)	−0.1992 (7)	0.1650 (15)	0.131 (7)
H2S1	0.4597	−0.2228	0.1700	0.157*
H2S2	0.5958	−0.2066	0.2351	0.157*
C3S	0.5674 (15)	−0.2376 (10)	0.0748 (16)	0.187 (10)
H3S1	0.6259	−0.2064	0.0570	0.280*
H3S2	0.4975	−0.2434	0.0106	0.280*
H3S3	0.6011	−0.2876	0.0994	0.280*

	U11	U22	U33	U12	U13	U23
U1	0.03164 (17)	0.02203 (15)	0.03026 (15)	0.00084 (11)	0.00514 (11)	0.00180 (10)
O2	0.037 (3)	0.027 (2)	0.037 (3)	0.002 (2)	0.010 (2)	0.004 (2)
O3	0.037 (3)	0.027 (2)	0.038 (3)	0.001 (2)	0.010 (2)	0.002 (2)
O4	0.030 (3)	0.026 (2)	0.030 (2)	0.002 (2)	0.001 (2)	−0.001 (2)
C5	0.084 (8)	0.055 (6)	0.074 (7)	−0.001 (6)	−0.026 (6)	−0.012 (5)
C6	0.081 (10)	0.057 (7)	0.168 (16)	−0.022 (6)	−0.042 (10)	−0.001 (7)
C7	0.026 (4)	0.037 (4)	0.034 (4)	−0.006 (3)	−0.003 (3)	0.011 (3)
O8	0.033 (3)	0.030 (2)	0.043 (3)	−0.002 (2)	0.011 (2)	0.008 (2)
C9	0.036 (4)	0.034 (4)	0.043 (4)	0.006 (3)	0.010 (4)	0.002 (3)
C10	0.036 (4)	0.046 (5)	0.047 (5)	−0.004 (4)	0.009 (4)	0.010 (4)
C11	0.041 (5)	0.057 (5)	0.048 (5)	0.003 (4)	0.019 (4)	0.019 (4)
C12	0.036 (4)	0.040 (4)	0.044 (4)	−0.002 (4)	0.001 (4)	0.019 (4)
C13	0.035 (4)	0.033 (4)	0.042 (4)	0.000 (3)	0.008 (4)	0.008 (3)
C14	0.031 (4)	0.039 (4)	0.043 (4)	−0.005 (3)	0.004 (3)	0.012 (3)
N15	0.041 (4)	0.022 (3)	0.046 (4)	0.002 (3)	0.001 (3)	−0.003 (3)
N16	0.050 (4)	0.030 (3)	0.057 (4)	−0.001 (3)	0.006 (4)	0.002 (3)
C17	0.048 (5)	0.018 (3)	0.035 (4)	−0.004 (3)	0.003 (4)	0.001 (3)
S18	0.0659 (15)	0.0357 (10)	0.0487 (12)	0.0003 (10)	0.0211 (11)	−0.0008 (9)
C19	0.079 (7)	0.030 (4)	0.067 (6)	−0.003 (4)	0.025 (5)	−0.002 (4)
C20	0.067 (6)	0.038 (5)	0.064 (6)	−0.007 (4)	0.020 (5)	−0.004 (4)
C21	0.088 (8)	0.030 (4)	0.067 (6)	0.000 (5)	0.013 (6)	0.002 (4)
N22	0.042 (4)	0.026 (3)	0.033 (3)	0.001 (3)	0.006 (3)	−0.002 (3)
C23	0.038 (4)	0.036 (4)	0.037 (4)	0.008 (3)	0.002 (3)	−0.004 (3)
C24	0.044 (5)	0.049 (5)	0.028 (4)	0.008 (4)	0.008 (3)	−0.006 (3)
C25	0.032 (4)	0.036 (4)	0.032 (4)	0.011 (3)	0.008 (3)	0.007 (3)
O26	0.034 (3)	0.029 (2)	0.034 (3)	0.002 (2)	0.010 (2)	−0.002 (2)
C27	0.035 (4)	0.038 (4)	0.040 (4)	0.005 (3)	0.012 (3)	0.002 (3)
C28	0.044 (5)	0.040 (4)	0.042 (4)	−0.009 (4)	0.010 (4)	0.010 (4)
O29	0.061 (4)	0.073 (4)	0.048 (3)	−0.019 (3)	0.012 (3)	0.003 (3)
C30	0.052 (5)	0.077 (7)	0.032 (4)	−0.012 (5)	0.013 (4)	−0.013 (4)
C31	0.053 (5)	0.045 (5)	0.036 (4)	−0.002 (4)	0.017 (4)	−0.011 (4)
O1S	0.043 (4)	0.066 (4)	0.067 (4)	−0.005 (3)	−0.004 (3)	0.005 (3)
C2S	0.058 (8)	0.067 (8)	0.25 (2)	−0.008 (7)	0.020 (10)	0.049 (11)
C3S	0.118 (14)	0.139 (15)	0.23 (2)	0.061 (12)	−0.046 (14)	−0.079 (15)

U1—O2	1.772 (5)	C17—S18	1.756 (7)
U1—O3	1.778 (5)	S18—C19	1.812 (9)
U1—O26	2.254 (5)	C19—C20	1.492 (11)
U1—O8	2.285 (5)	C19—H19A	0.9900
U1—O4	2.394 (4)	C19—H19B	0.9900
U1—N22	2.540 (6)	C20—C21	1.306 (12)
U1—N15	2.562 (6)	C20—H20	0.9500
O4—C5	1.417 (10)	C21—H21A	0.9500
O4—H4	0.8600	C21—H21B	0.9500
C5—C6	1.4995 (10)	N22—C23	1.310 (9)
C5—H5A	0.9900	C23—C24	1.406 (11)
C5—H5B	0.9900	C23—H23	0.9500
C6—H6A	0.9800	C24—C31	1.404 (10)
C6—H6B	0.9800	C24—C25	1.429 (10)
C6—H6C	0.9800	C25—O26	1.323 (8)
C7—O8	1.351 (9)	C25—C27	1.376 (10)
C7—C9	1.386 (10)	C27—C28	1.403 (10)
C7—C13	1.419 (9)	C27—H27	0.9500
C9—C10	1.367 (10)	C28—O29	1.314 (9)
C9—H9	0.9500	C28—C30	1.411 (11)
C10—C11	1.406 (10)	O29—H29	0.8600
C10—H10	0.9500	C30—C31	1.337 (11)
C11—C12	1.356 (11)	C30—H30	0.9500
C11—H11	0.9500	C31—H31	0.9500
C12—C13	1.429 (10)	O1S—C2S	1.362 (12)
C12—H12	0.9500	O1S—H1S1	0.8601
C13—C14	1.400 (10)	C2S—C3S	1.54 (2)
C14—N15	1.322 (9)	C2S—H2S1	0.9900
C14—H14	0.9500	C2S—H2S2	0.9900
N15—N16	1.378 (8)	C3S—H3S1	0.9800
N16—C17	1.273 (10)	C3S—H3S2	0.9800
C17—N22	1.422 (9)	C3S—H3S3	0.9800
O2—U1—O3	177.8 (2)	C14—N15—U1	124.7 (5)
O2—U1—O26	86.3 (2)	N16—N15—U1	122.1 (5)
O3—U1—O26	92.0 (2)	C17—N16—N15	114.5 (6)
O2—U1—O8	95.3 (2)	N16—C17—N22	123.6 (7)
O3—U1—O8	85.8 (2)	N16—C17—S18	118.2 (5)
O26—U1—O8	160.74 (18)	N22—C17—S18	118.1 (6)
O2—U1—O4	88.96 (18)	C17—S18—C19	100.9 (4)
O3—U1—O4	89.27 (19)	C20—C19—S18	107.9 (6)
O26—U1—O4	79.50 (16)	C20—C19—H19A	110.1
O8—U1—O4	81.34 (16)	S18—C19—H19A	110.1
O2—U1—N22	97.1 (2)	C20—C19—H19B	110.1
O3—U1—N22	83.8 (2)	S18—C19—H19B	110.1
O26—U1—N22	70.73 (18)	H19A—C19—H19B	108.4
O8—U1—N22	127.82 (19)	C21—C20—C19	123.0 (9)
O4—U1—N22	149.10 (18)	C21—C20—H20	118.5
O2—U1—N15	80.9 (2)	C19—C20—H20	118.5
O3—U1—N15	101.3 (2)	C20—C21—H21A	120.0
O26—U1—N15	128.91 (19)	C20—C21—H21B	120.0
O8—U1—N15	70.15 (18)	H21A—C21—H21B	120.0
O4—U1—N15	148.54 (18)	C23—N22—C17	118.7 (6)
N22—U1—N15	62.2 (2)	C23—N22—U1	123.0 (5)
C5—O4—U1	129.2 (5)	C17—N22—U1	117.0 (5)
C5—O4—H4	109.7	N22—C23—C24	127.0 (7)
U1—O4—H4	120.9	N22—C23—H23	116.5
O4—C5—C6	113.3 (8)	C24—C23—H23	116.5
O4—C5—H5A	108.9	C31—C24—C23	118.7 (7)
C6—C5—H5A	108.9	C31—C24—C25	117.0 (7)
O4—C5—H5B	108.9	C23—C24—C25	124.2 (7)
C6—C5—H5B	108.9	O26—C25—C27	119.4 (7)
H5A—C5—H5B	107.7	O26—C25—C24	120.0 (7)
C5—C6—H6A	109.5	C27—C25—C24	120.5 (7)
C5—C6—H6B	109.5	C25—O26—U1	127.8 (4)
H6A—C6—H6B	109.5	C25—C27—C28	119.9 (7)
C5—C6—H6C	109.5	C25—C27—H27	120.0
H6A—C6—H6C	109.5	C28—C27—H27	120.0
H6B—C6—H6C	109.5	O29—C28—C27	122.7 (7)
O8—C7—C9	120.6 (6)	O29—C28—C30	117.5 (7)
O8—C7—C13	118.9 (7)	C27—C28—C30	119.8 (7)
C9—C7—C13	120.5 (7)	C28—O29—H29	112.8
C7—O8—U1	134.8 (4)	C31—C30—C28	119.4 (7)
C10—C9—C7	120.3 (7)	C31—C30—H30	120.3
C10—C9—H9	119.8	C28—C30—H30	120.3
C7—C9—H9	119.8	C30—C31—C24	123.2 (7)
C9—C10—C11	121.2 (8)	C30—C31—H31	118.4
C9—C10—H10	119.4	C24—C31—H31	118.4
C11—C10—H10	119.4	C2S—O1S—H1S1	104.6
C12—C11—C10	119.0 (7)	O1S—C2S—C3S	110.5 (14)
C12—C11—H11	120.5	O1S—C2S—H2S1	109.6
C10—C11—H11	120.5	C3S—C2S—H2S1	109.6
C11—C12—C13	122.1 (7)	O1S—C2S—H2S2	109.6
C11—C12—H12	119.0	C3S—C2S—H2S2	109.6
C13—C12—H12	119.0	H2S1—C2S—H2S2	108.1
C14—C13—C7	124.7 (7)	C2S—C3S—H3S1	109.5
C14—C13—C12	118.2 (7)	C2S—C3S—H3S2	109.5
C7—C13—C12	116.9 (7)	H3S1—C3S—H3S2	109.5
N15—C14—C13	128.6 (7)	C2S—C3S—H3S3	109.5
N15—C14—H14	115.7	H3S1—C3S—H3S3	109.5
C13—C14—H14	115.7	H3S2—C3S—H3S3	109.5
C14—N15—N16	111.7 (6)
O2—U1—O4—C5	−14.1 (7)	N16—C17—S18—C19	−0.2 (7)
O3—U1—O4—C5	164.5 (7)	N22—C17—S18—C19	−176.1 (6)
O26—U1—O4—C5	72.3 (7)	C17—S18—C19—C20	−170.4 (7)
O8—U1—O4—C5	−109.6 (7)	S18—C19—C20—C21	−100.9 (10)
N22—U1—O4—C5	87.9 (8)	N16—C17—N22—C23	167.0 (7)
N15—U1—O4—C5	−84.7 (8)	S18—C17—N22—C23	−17.3 (9)
U1—O4—C5—C6	−134.3 (8)	N16—C17—N22—U1	−0.5 (9)
C9—C7—O8—U1	−138.9 (6)	S18—C17—N22—U1	175.2 (3)
C13—C7—O8—U1	42.9 (10)	O2—U1—N22—C23	120.5 (6)
O2—U1—O8—C7	29.9 (6)	O3—U1—N22—C23	−57.4 (6)
O3—U1—O8—C7	−152.1 (6)	O26—U1—N22—C23	36.9 (5)
O26—U1—O8—C7	123.9 (7)	O8—U1—N22—C23	−137.2 (5)
O4—U1—O8—C7	118.0 (6)	O4—U1—N22—C23	20.7 (8)
N22—U1—O8—C7	−73.3 (7)	N15—U1—N22—C23	−163.7 (6)
N15—U1—O8—C7	−48.5 (6)	O2—U1—N22—C17	−72.5 (5)
O8—C7—C9—C10	−177.8 (7)	O3—U1—N22—C17	109.6 (5)
C13—C7—C9—C10	0.4 (11)	O26—U1—N22—C17	−156.1 (5)
C7—C9—C10—C11	−0.6 (12)	O8—U1—N22—C17	29.8 (6)
C9—C10—C11—C12	1.4 (12)	O4—U1—N22—C17	−172.4 (4)
C10—C11—C12—C13	−2.0 (12)	N15—U1—N22—C17	3.3 (5)
O8—C7—C13—C14	2.1 (11)	C17—N22—C23—C24	177.0 (7)
C9—C7—C13—C14	−176.2 (7)	U1—N22—C23—C24	−16.3 (10)
O8—C7—C13—C12	177.2 (6)	N22—C23—C24—C31	170.9 (7)
C9—C7—C13—C12	−1.0 (11)	N22—C23—C24—C25	−12.0 (12)
C11—C12—C13—C14	177.3 (7)	C31—C24—C25—O26	174.5 (7)
C11—C12—C13—C7	1.8 (11)	C23—C24—C25—O26	−2.7 (11)
C7—C13—C14—N15	−12.0 (13)	C31—C24—C25—C27	−1.7 (11)
C12—C13—C14—N15	172.9 (7)	C23—C24—C25—C27	−178.9 (7)
C13—C14—N15—N16	179.5 (7)	C27—C25—O26—U1	−130.7 (6)
C13—C14—N15—U1	−14.2 (11)	C24—C25—O26—U1	53.1 (8)
O2—U1—N15—C14	−68.2 (6)	O2—U1—O26—C25	−155.6 (6)
O3—U1—N15—C14	112.1 (6)	O3—U1—O26—C25	25.9 (6)
O26—U1—N15—C14	−146.0 (5)	O8—U1—O26—C25	108.9 (7)
O8—U1—N15—C14	30.8 (5)	O4—U1—O26—C25	114.8 (5)
O4—U1—N15—C14	4.5 (8)	N22—U1—O26—C25	−56.8 (5)
N22—U1—N15—C14	−171.2 (6)	N15—U1—O26—C25	−80.4 (6)
O2—U1—N15—N16	96.7 (5)	O26—C25—C27—C28	−176.5 (7)
O3—U1—N15—N16	−83.0 (5)	C24—C25—C27—C28	−0.3 (11)
O26—U1—N15—N16	19.0 (6)	C25—C27—C28—O29	−176.7 (7)
O8—U1—N15—N16	−164.3 (6)	C25—C27—C28—C30	1.5 (12)
O4—U1—N15—N16	169.5 (4)	O29—C28—C30—C31	177.9 (8)
N22—U1—N15—N16	−6.3 (5)	C27—C28—C30—C31	−0.4 (13)
C14—N15—N16—C17	175.2 (7)	C28—C30—C31—C24	−1.8 (14)
U1—N15—N16—C17	8.5 (8)	C23—C24—C31—C30	−179.8 (8)
N15—N16—C17—N22	−5.1 (10)	C25—C24—C31—C30	2.9 (12)
N15—N16—C17—S18	179.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O8i	0.86	1.75	2.601 (7)	173.
O29—H29···O1S	0.86	1.79	2.646 (9)	171.
O1S—H1S1···O26ii	0.86	1.87	2.718 (8)	169.
C23—H23···O2iii	0.95	2.49	3.395 (9)	158.
C27—H27···O1S	0.95	2.51	3.189 (10)	128.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O8i	0.86	1.75	2.601 (7)	173
O29—H29⋯O1S	0.86	1.79	2.646 (9)	171
O1S—H1S1⋯O26ii	0.86	1.87	2.718 (8)	169
C23—H23⋯O2iii	0.95	2.49	3.395 (9)	158
C27—H27⋯O1S	0.95	2.51	3.189 (10)	128

Symmetry codes: (i) ; (ii) ; (iii) .