Bis-(4-benzoyl-3-methyl-1-phenyl-4,5-di-hydro-1H-pyrazol-5-olato-κ(2)O,O')(methanol-κO)dioxidouranium(VI) methanol monosolvate.

In the title compound, [U(C(17)H(13)N(2)O(2))(2)O(2)(CH(3)OH)]·CH(3)OH, the U(VI) ion is coordinated by seven O atoms in a distorted pentagonal-bipyramidal geometry with two 3-methyl-1-phenyl-4-benzoyl-4,5-dihydro-1H-pyrazol-5-olate groups with two O atoms in a bidentate chelating coordination mode and by three O atoms, one of which is from a methanol ligand. The crystal packing can be described by alternating layers of complex mol-ecules along the a axis. The structure is stabilized by O-H⋯N and O-H⋯O hydrogen bonding and van der Waals inter-actions.

Related literature

For the synthesis and applications of similar compounds: Okafor (1981 ▶); Caruso et al. (2000 ▶); Li et al. (1997 ▶); Zhou et al. (1999 ▶).

Experimental

Crystal data

[U(C17H13N2O2)2O2(CH4O)]·CH4O

M = 888.7

Triclinic,

a = 10.3353 (18) Å

b = 12.988 (2) Å

c = 13.955 (3) Å

α = 69.938 (3)°

β = 81.728 (2)°

γ = 70.722 (3)°

V = 1659.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 4.95 mm−1

T = 173 K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T min = 0.242, T max = 0.318

20251 measured reflections

10125 independent reflections

8127 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.096

S = 1.00

10125 reflections

450 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.45 e Å−3

Δρmin = −3.52 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011075/bq2342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011075/bq2342Isup2.hkl

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

[U(C17H13N2O2)2O2(CH4O)]·CH4O	Z = 2
Mr = 888.7	F(000) = 868
Triclinic, P1	Dx = 1.778 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3353 (18) Å	Cell parameters from 5297 reflections
b = 12.988 (2) Å	θ = 2.4–26.8°
c = 13.955 (3) Å	µ = 4.95 mm−1
α = 69.938 (3)°	T = 173 K
β = 81.728 (2)°	Block, orange
γ = 70.722 (3)°	0.40 × 0.40 × 0.30 mm
V = 1659.9 (5) Å3

Bruker APEXII diffractometer	10125 independent reflections
Radiation source: fine-focus sealed tube	8127 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
phi and ω scans	θmax = 30.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −14→14
Tmin = 0.242, Tmax = 0.318	k = −18→18
20251 measured reflections	l = −20→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0322P)2] where P = (Fo2 + 2Fc2)/3
10125 reflections	(Δ/σ)max = 0.002
450 parameters	Δρmax = 2.45 e Å−3
1 restraint	Δρmin = −3.52 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.3016 (5)	0.0112 (4)	1.0673 (3)	0.0181 (9)
C2	0.4041 (5)	−0.0758 (5)	1.1291 (4)	0.0269 (11)
H2	0.4829	−0.0614	1.1386	0.032*
C3	0.3878 (5)	−0.1836 (4)	1.1761 (4)	0.0247 (11)
H3	0.4567	−0.2416	1.2166	0.03*
C4	0.2714 (5)	−0.2063 (4)	1.1640 (4)	0.0252 (11)
H4	0.2608	−0.2787	1.1971	0.03*
C5	0.1707 (5)	−0.1207 (4)	1.1023 (4)	0.0254 (11)
H5	0.0926	−0.1363	1.093	0.03*
C6	0.1834 (5)	−0.0119 (4)	1.0541 (4)	0.0232 (10)
H6	0.1142	0.0453	1.0133	0.028*
C7	0.2455 (5)	0.2101 (4)	0.9434 (3)	0.0177 (9)
C8	0.2818 (5)	0.3085 (4)	0.9380 (4)	0.0194 (10)
C9	0.3811 (5)	0.2681 (4)	1.0143 (4)	0.0207 (10)
C10	0.4678 (6)	0.3295 (5)	1.0350 (4)	0.0297 (12)
H10A	0.5279	0.2783	1.0894	0.045*
H10B	0.41	0.3946	1.0542	0.045*
H10C	0.5213	0.355	0.9746	0.045*
C11	0.2170 (5)	0.4193 (4)	0.8721 (4)	0.0199 (10)
C12	0.2119 (5)	0.5265 (4)	0.8918 (4)	0.0210 (10)
C13	0.1680 (6)	0.5421 (5)	0.9852 (4)	0.0283 (12)
H13	0.1491	0.4821	1.039	0.034*
C14	0.1516 (6)	0.6457 (5)	1.0000 (4)	0.0316 (12)
H14	0.1197	0.6564	1.0627	0.038*
C15	0.1831 (5)	0.7329 (5)	0.9206 (5)	0.0319 (13)
H15	0.1741	0.8023	0.9304	0.038*
C16	0.2276 (5)	0.7186 (4)	0.8270 (4)	0.0289 (12)
H16	0.2487	0.7781	0.7741	0.035*
C17	0.2413 (5)	0.6159 (4)	0.8112 (4)	0.0258 (11)
H17	0.2697	0.6067	0.7475	0.031*
C18	0.2910 (5)	0.6501 (4)	0.4807 (4)	0.0220 (10)
C19	0.1797 (5)	0.7099 (4)	0.5284 (4)	0.0277 (11)
H19	0.0975	0.692	0.5404	0.033*
C20	0.1938 (6)	0.7969 (5)	0.5578 (5)	0.0343 (13)
H20	0.1209	0.8373	0.5911	0.041*
C21	0.3159 (6)	0.8245 (5)	0.5380 (5)	0.0343 (13)
H21	0.3244	0.883	0.5581	0.041*
C22	0.4226 (5)	0.7662 (5)	0.4893 (4)	0.0300 (12)
H22	0.5036	0.7858	0.4757	0.036*
C23	0.4125 (5)	0.6786 (5)	0.4600 (4)	0.0299 (12)
H23	0.4862	0.6388	0.4268	0.036*
C24	0.2139 (5)	0.4804 (4)	0.4970 (4)	0.0207 (10)
C25	0.2349 (5)	0.4098 (4)	0.4349 (4)	0.0216 (10)
C26	0.3228 (5)	0.4549 (4)	0.3511 (4)	0.0232 (10)
C27	0.3865 (6)	0.4137 (5)	0.2632 (4)	0.0369 (14)
H27A	0.4586	0.447	0.2322	0.055*
H27B	0.3182	0.436	0.2139	0.055*
H27C	0.4237	0.3314	0.2867	0.055*
C28	0.1815 (5)	0.3184 (4)	0.4603 (4)	0.0233 (10)
C29	0.1708 (5)	0.2638 (4)	0.3842 (4)	0.0224 (10)
C30	0.2010 (5)	0.1454 (4)	0.4139 (4)	0.0274 (11)
H30	0.2326	0.101	0.479	0.033*
C31	0.1844 (6)	0.0924 (5)	0.3468 (4)	0.0320 (12)
H31	0.2052	0.0128	0.3669	0.038*
C32	0.1375 (5)	0.1580 (5)	0.2513 (4)	0.0276 (11)
H32	0.1279	0.1228	0.2061	0.033*
C33	0.1043 (5)	0.2758 (5)	0.2219 (4)	0.0276 (11)
H33	0.0704	0.3197	0.1574	0.033*
C34	0.1209 (5)	0.3296 (4)	0.2878 (4)	0.0261 (11)
H34	0.0988	0.4093	0.2674	0.031*
C35	0.0585 (6)	0.0644 (5)	0.7008 (4)	0.0328 (13)
H35A	−0.0238	0.1242	0.6743	0.049*
H35B	0.035	0.0017	0.7528	0.049*
H35C	0.1107	0.0377	0.6467	0.049*
C36S	0.4590 (7)	0.9616 (7)	0.7067 (5)	0.0525 (18)
H36A	0.5134	1.0098	0.7042	0.079*
H36B	0.4022	0.9956	0.6484	0.079*
H36C	0.5183	0.8871	0.7063	0.079*
N1	0.3146 (4)	0.1229 (3)	1.0221 (3)	0.0199 (8)
N2	0.4026 (4)	0.1577 (3)	1.0642 (3)	0.0206 (8)
N3	0.2801 (4)	0.5596 (4)	0.4498 (3)	0.0246 (9)
N4	0.3513 (4)	0.5416 (4)	0.3602 (3)	0.0263 (9)
O1	0.1436 (3)	0.4773 (3)	0.5828 (3)	0.0221 (7)
O2	0.1534 (4)	0.4329 (3)	0.7957 (3)	0.0257 (8)
O3	0.1624 (3)	0.2027 (3)	0.8890 (2)	0.0225 (7)
O4	0.1342 (3)	0.2794 (3)	0.5502 (3)	0.0242 (8)
O5	0.3227 (3)	0.2567 (3)	0.6995 (3)	0.0232 (7)
O6	−0.0384 (3)	0.3501 (3)	0.7243 (3)	0.0223 (7)
O7	0.1379 (4)	0.1080 (3)	0.7434 (3)	0.0253 (8)
H7O	0.207 (4)	0.058 (4)	0.768 (4)	0.038*
O36S	0.3752 (4)	0.9501 (3)	0.7970 (3)	0.0358 (9)
H36S	0.4216	0.9349	0.8458	0.054*
U1	0.141702 (17)	0.305351 (14)	0.710418 (13)	0.01446 (5)

	U11	U22	U33	U12	U13	U23
C1	0.021 (2)	0.019 (2)	0.014 (2)	−0.0062 (18)	0.0028 (18)	−0.0060 (18)
C2	0.024 (2)	0.032 (3)	0.028 (3)	−0.011 (2)	−0.006 (2)	−0.008 (2)
C3	0.018 (2)	0.019 (2)	0.029 (3)	0.0030 (19)	−0.006 (2)	−0.004 (2)
C4	0.029 (3)	0.018 (2)	0.028 (3)	−0.009 (2)	0.001 (2)	−0.006 (2)
C5	0.028 (3)	0.027 (3)	0.028 (3)	−0.012 (2)	−0.007 (2)	−0.011 (2)
C6	0.021 (2)	0.024 (2)	0.023 (3)	−0.006 (2)	−0.0052 (19)	−0.004 (2)
C7	0.021 (2)	0.023 (2)	0.011 (2)	−0.0065 (19)	−0.0016 (17)	−0.0072 (19)
C8	0.020 (2)	0.018 (2)	0.020 (2)	−0.0045 (18)	−0.0037 (18)	−0.0059 (19)
C9	0.022 (2)	0.022 (2)	0.019 (2)	−0.0074 (19)	−0.0028 (19)	−0.007 (2)
C10	0.037 (3)	0.028 (3)	0.032 (3)	−0.017 (2)	−0.011 (2)	−0.007 (2)
C11	0.022 (2)	0.018 (2)	0.021 (2)	−0.0060 (19)	−0.0009 (19)	−0.0061 (19)
C12	0.019 (2)	0.021 (2)	0.023 (3)	−0.0024 (19)	−0.0031 (19)	−0.010 (2)
C13	0.037 (3)	0.025 (3)	0.026 (3)	−0.014 (2)	−0.001 (2)	−0.007 (2)
C14	0.038 (3)	0.038 (3)	0.027 (3)	−0.013 (3)	0.003 (2)	−0.021 (3)
C15	0.031 (3)	0.025 (3)	0.047 (4)	−0.007 (2)	−0.007 (3)	−0.020 (3)
C16	0.032 (3)	0.021 (2)	0.035 (3)	−0.013 (2)	−0.003 (2)	−0.005 (2)
C17	0.027 (3)	0.022 (2)	0.027 (3)	−0.007 (2)	−0.004 (2)	−0.006 (2)
C18	0.020 (2)	0.016 (2)	0.027 (3)	−0.0031 (18)	−0.0045 (19)	−0.002 (2)
C19	0.027 (3)	0.025 (3)	0.032 (3)	−0.012 (2)	0.003 (2)	−0.007 (2)
C20	0.033 (3)	0.026 (3)	0.045 (4)	−0.009 (2)	0.007 (3)	−0.015 (3)
C21	0.043 (3)	0.020 (3)	0.042 (4)	−0.013 (2)	−0.013 (3)	−0.005 (2)
C22	0.022 (2)	0.029 (3)	0.039 (3)	−0.011 (2)	−0.005 (2)	−0.007 (2)
C23	0.023 (2)	0.027 (3)	0.041 (3)	−0.010 (2)	−0.002 (2)	−0.010 (2)
C24	0.022 (2)	0.014 (2)	0.021 (2)	−0.0067 (18)	−0.0126 (19)	0.0060 (19)
C25	0.017 (2)	0.026 (2)	0.019 (2)	−0.0004 (19)	−0.0069 (18)	−0.007 (2)
C26	0.018 (2)	0.027 (3)	0.022 (3)	−0.007 (2)	−0.0014 (19)	−0.004 (2)
C27	0.037 (3)	0.048 (4)	0.031 (3)	−0.019 (3)	0.006 (2)	−0.015 (3)
C28	0.022 (2)	0.020 (2)	0.020 (3)	−0.0007 (19)	−0.0089 (19)	0.001 (2)
C29	0.023 (2)	0.024 (2)	0.020 (3)	−0.007 (2)	−0.0035 (19)	−0.006 (2)
C30	0.035 (3)	0.023 (3)	0.023 (3)	−0.007 (2)	−0.005 (2)	−0.006 (2)
C31	0.039 (3)	0.023 (3)	0.035 (3)	−0.009 (2)	0.000 (2)	−0.011 (2)
C32	0.023 (2)	0.040 (3)	0.030 (3)	−0.014 (2)	0.004 (2)	−0.020 (3)
C33	0.024 (2)	0.041 (3)	0.019 (3)	−0.013 (2)	−0.004 (2)	−0.007 (2)
C34	0.023 (2)	0.023 (2)	0.029 (3)	−0.006 (2)	−0.003 (2)	−0.003 (2)
C35	0.037 (3)	0.035 (3)	0.036 (3)	−0.019 (3)	−0.002 (2)	−0.015 (3)
C36S	0.039 (4)	0.065 (5)	0.058 (5)	0.001 (3)	−0.015 (3)	−0.036 (4)
N1	0.0207 (19)	0.0183 (19)	0.021 (2)	−0.0052 (16)	−0.0050 (16)	−0.0057 (17)
N2	0.0175 (18)	0.022 (2)	0.023 (2)	−0.0059 (16)	−0.0029 (16)	−0.0081 (18)
N3	0.022 (2)	0.028 (2)	0.023 (2)	−0.0094 (18)	0.0007 (17)	−0.0063 (19)
N4	0.021 (2)	0.030 (2)	0.026 (2)	−0.0088 (18)	0.0007 (17)	−0.0058 (19)
O1	0.0249 (17)	0.0203 (17)	0.0211 (18)	−0.0100 (14)	0.0050 (14)	−0.0061 (14)
O2	0.035 (2)	0.0194 (17)	0.0234 (19)	−0.0055 (15)	−0.0116 (15)	−0.0062 (15)
O3	0.0279 (18)	0.0166 (16)	0.0206 (18)	−0.0054 (14)	−0.0072 (14)	−0.0019 (14)
O4	0.0287 (18)	0.0280 (19)	0.0178 (18)	−0.0139 (16)	−0.0002 (14)	−0.0047 (15)
O5	0.0158 (15)	0.0296 (19)	0.0270 (19)	−0.0092 (14)	−0.0029 (14)	−0.0091 (16)
O6	0.0168 (15)	0.0244 (18)	0.0248 (19)	−0.0058 (14)	−0.0041 (13)	−0.0057 (15)
O7	0.0279 (19)	0.0160 (17)	0.032 (2)	−0.0026 (14)	−0.0136 (16)	−0.0064 (16)
O36S	0.032 (2)	0.030 (2)	0.045 (3)	−0.0058 (17)	−0.0157 (18)	−0.009 (2)
U1	0.01361 (8)	0.01473 (8)	0.01518 (9)	−0.00454 (6)	−0.00239 (6)	−0.00391 (6)

C1—C2	1.395 (7)	C22—H22	0.93
C1—C6	1.400 (6)	C23—H23	0.93
C1—N1	1.413 (6)	C24—O1	1.304 (6)
C2—C3	1.383 (7)	C24—N3	1.353 (6)
C2—H2	0.93	C24—C25	1.413 (7)
C3—C4	1.375 (7)	C25—C28	1.388 (7)
C3—H3	0.93	C25—C26	1.454 (7)
C4—C5	1.378 (7)	C26—N4	1.302 (7)
C4—H4	0.93	C26—C27	1.486 (7)
C5—C6	1.383 (7)	C27—H27A	0.96
C5—H5	0.93	C27—H27B	0.96
C6—H6	0.93	C27—H27C	0.96
C7—O3	1.271 (5)	C28—O4	1.273 (6)
C7—N1	1.355 (6)	C28—C29	1.498 (7)
C7—C8	1.422 (6)	C29—C30	1.384 (7)
C8—C11	1.414 (6)	C29—C34	1.388 (7)
C8—C9	1.427 (6)	C30—C31	1.396 (8)
C9—N2	1.319 (6)	C30—H30	0.93
C9—C10	1.492 (7)	C31—C32	1.368 (7)
C10—H10A	0.96	C31—H31	0.93
C10—H10B	0.96	C32—C33	1.374 (8)
C10—H10C	0.96	C32—H32	0.93
C11—O2	1.262 (6)	C33—C34	1.389 (7)
C11—C12	1.493 (7)	C33—H33	0.93
C12—C13	1.377 (7)	C34—H34	0.93
C12—C17	1.394 (7)	C35—O7	1.424 (6)
C13—C14	1.383 (7)	C35—H35A	0.96
C13—H13	0.93	C35—H35B	0.96
C14—C15	1.376 (8)	C35—H35C	0.96
C14—H14	0.93	C36S—O36S	1.415 (8)
C15—C16	1.375 (8)	C36S—H36A	0.96
C15—H15	0.93	C36S—H36B	0.96
C16—C17	1.383 (7)	C36S—H36C	0.96
C16—H16	0.93	N1—N2	1.409 (5)
C17—H17	0.93	N3—N4	1.408 (6)
C18—C19	1.383 (7)	O1—U1	2.334 (3)
C18—C23	1.389 (7)	O2—U1	2.388 (3)
C18—N3	1.426 (6)	O3—U1	2.391 (3)
C19—C20	1.382 (8)	O4—U1	2.388 (3)
C19—H19	0.93	O5—U1	1.768 (3)
C20—C21	1.388 (7)	O6—U1	1.761 (3)
C20—H20	0.93	O7—U1	2.456 (3)
C21—C22	1.355 (8)	O7—H7O	0.811 (19)
C21—H21	0.93	O36S—H36S	0.82
C22—C23	1.371 (7)
C2—C1—C6	119.4 (4)	N4—C26—C27	118.0 (4)
C2—C1—N1	120.1 (4)	C25—C26—C27	129.8 (5)
C6—C1—N1	120.4 (4)	C26—C27—H27A	109.5
C3—C2—C1	119.6 (5)	C26—C27—H27B	109.5
C3—C2—H2	120.2	H27A—C27—H27B	109.5
C1—C2—H2	120.2	C26—C27—H27C	109.5
C4—C3—C2	121.1 (5)	H27A—C27—H27C	109.5
C4—C3—H3	119.4	H27B—C27—H27C	109.5
C2—C3—H3	119.4	O4—C28—C25	120.7 (5)
C3—C4—C5	119.2 (5)	O4—C28—C29	116.6 (4)
C3—C4—H4	120.4	C25—C28—C29	122.7 (4)
C5—C4—H4	120.4	C30—C29—C34	119.4 (5)
C4—C5—C6	121.2 (5)	C30—C29—C28	118.9 (4)
C4—C5—H5	119.4	C34—C29—C28	121.5 (5)
C6—C5—H5	119.4	C29—C30—C31	120.3 (5)
C5—C6—C1	119.4 (4)	C29—C30—H30	119.8
C5—C6—H6	120.3	C31—C30—H30	119.8
C1—C6—H6	120.3	C32—C31—C30	119.7 (5)
O3—C7—N1	125.3 (4)	C32—C31—H31	120.2
O3—C7—C8	128.4 (4)	C30—C31—H31	120.2
N1—C7—C8	106.3 (4)	C31—C32—C33	120.4 (5)
C11—C8—C7	122.2 (4)	C31—C32—H32	119.8
C11—C8—C9	132.6 (4)	C33—C32—H32	119.8
C7—C8—C9	105.1 (4)	C32—C33—C34	120.5 (5)
N2—C9—C8	111.4 (4)	C32—C33—H33	119.7
N2—C9—C10	119.2 (4)	C34—C33—H33	119.7
C8—C9—C10	129.1 (4)	C29—C34—C33	119.6 (5)
C9—C10—H10A	109.5	C29—C34—H34	120.2
C9—C10—H10B	109.5	C33—C34—H34	120.2
H10A—C10—H10B	109.5	O7—C35—H35A	109.5
C9—C10—H10C	109.5	O7—C35—H35B	109.5
H10A—C10—H10C	109.5	H35A—C35—H35B	109.5
H10B—C10—H10C	109.5	O7—C35—H35C	109.5
O2—C11—C8	121.4 (4)	H35A—C35—H35C	109.5
O2—C11—C12	116.1 (4)	H35B—C35—H35C	109.5
C8—C11—C12	122.4 (4)	O36S—C36S—H36A	109.5
C13—C12—C17	119.7 (5)	O36S—C36S—H36B	109.5
C13—C12—C11	121.2 (4)	H36A—C36S—H36B	109.5
C17—C12—C11	118.8 (4)	O36S—C36S—H36C	109.5
C12—C13—C14	120.8 (5)	H36A—C36S—H36C	109.5
C12—C13—H13	119.6	H36B—C36S—H36C	109.5
C14—C13—H13	119.6	C7—N1—N2	111.4 (4)
C15—C14—C13	119.2 (5)	C7—N1—C1	128.8 (4)
C15—C14—H14	120.4	N2—N1—C1	119.7 (4)
C13—C14—H14	120.4	C9—N2—N1	105.8 (4)
C16—C15—C14	120.8 (5)	C24—N3—N4	111.7 (4)
C16—C15—H15	119.6	C24—N3—C18	129.4 (4)
C14—C15—H15	119.6	N4—N3—C18	118.9 (4)
C15—C16—C17	120.3 (5)	C26—N4—N3	105.4 (4)
C15—C16—H16	119.8	C24—O1—U1	122.6 (3)
C17—C16—H16	119.8	C11—O2—U1	133.4 (3)
C16—C17—C12	119.2 (5)	C7—O3—U1	122.7 (3)
C16—C17—H17	120.4	C28—O4—U1	134.8 (3)
C12—C17—H17	120.4	C35—O7—U1	131.0 (3)
C19—C18—C23	121.1 (5)	C35—O7—H7O	111 (4)
C19—C18—N3	119.7 (4)	U1—O7—H7O	115 (4)
C23—C18—N3	119.2 (5)	C36S—O36S—H36S	109.5
C20—C19—C18	118.2 (5)	O6—U1—O5	178.33 (15)
C20—C19—H19	120.9	O6—U1—O1	92.53 (13)
C18—C19—H19	120.9	O5—U1—O1	89.13 (14)
C19—C20—C21	120.6 (5)	O6—U1—O4	92.24 (14)
C19—C20—H20	119.7	O5—U1—O4	88.38 (14)
C21—C20—H20	119.7	O1—U1—O4	72.52 (12)
C22—C21—C20	120.1 (5)	O6—U1—O2	89.92 (14)
C22—C21—H21	119.9	O5—U1—O2	90.42 (14)
C20—C21—H21	119.9	O1—U1—O2	73.82 (12)
C21—C22—C23	120.8 (5)	O4—U1—O2	146.33 (12)
C21—C22—H22	119.6	O6—U1—O3	91.12 (13)
C23—C22—H22	119.6	O5—U1—O3	87.43 (14)
C22—C23—C18	119.1 (5)	O1—U1—O3	145.24 (12)
C22—C23—H23	120.4	O4—U1—O3	141.85 (11)
C18—C23—H23	120.4	O2—U1—O3	71.63 (11)
O1—C24—N3	123.2 (5)	O6—U1—O7	89.51 (14)
O1—C24—C25	129.8 (4)	O5—U1—O7	89.21 (14)
N3—C24—C25	107.1 (4)	O1—U1—O7	144.37 (12)
C28—C25—C24	122.9 (5)	O4—U1—O7	71.86 (12)
C28—C25—C26	133.4 (5)	O2—U1—O7	141.79 (12)
C24—C25—C26	103.7 (4)	O3—U1—O7	70.18 (12)
N4—C26—C25	112.1 (5)
C6—C1—C2—C3	0.2 (8)	C32—C33—C34—C29	−0.3 (7)
N1—C1—C2—C3	177.5 (5)	O3—C7—N1—N2	177.7 (4)
C1—C2—C3—C4	−0.7 (8)	C8—C7—N1—N2	−4.3 (5)
C2—C3—C4—C5	1.3 (8)	O3—C7—N1—C1	−6.7 (8)
C3—C4—C5—C6	−1.2 (8)	C8—C7—N1—C1	171.4 (4)
C4—C5—C6—C1	0.7 (8)	C2—C1—N1—C7	163.4 (5)
C2—C1—C6—C5	−0.2 (7)	C6—C1—N1—C7	−19.4 (7)
N1—C1—C6—C5	−177.4 (5)	C2—C1—N1—N2	−21.3 (7)
O3—C7—C8—C11	5.4 (8)	C6—C1—N1—N2	155.9 (4)
N1—C7—C8—C11	−172.6 (4)	C8—C9—N2—N1	−0.9 (5)
O3—C7—C8—C9	−178.5 (5)	C10—C9—N2—N1	−175.0 (4)
N1—C7—C8—C9	3.5 (5)	C7—N1—N2—C9	3.3 (5)
C11—C8—C9—N2	173.9 (5)	C1—N1—N2—C9	−172.8 (4)
C7—C8—C9—N2	−1.6 (6)	O1—C24—N3—N4	178.3 (4)
C11—C8—C9—C10	−12.8 (9)	C25—C24—N3—N4	−3.0 (5)
C7—C8—C9—C10	171.7 (5)	O1—C24—N3—C18	1.5 (8)
C7—C8—C11—O2	−20.2 (7)	C25—C24—N3—C18	−179.9 (4)
C9—C8—C11—O2	164.9 (5)	C19—C18—N3—C24	−37.5 (7)
C7—C8—C11—C12	155.9 (5)	C23—C18—N3—C24	144.1 (5)
C9—C8—C11—C12	−19.0 (8)	C19—C18—N3—N4	145.8 (5)
O2—C11—C12—C13	125.6 (5)	C23—C18—N3—N4	−32.6 (7)
C8—C11—C12—C13	−50.7 (7)	C25—C26—N4—N3	−1.4 (5)
O2—C11—C12—C17	−48.9 (6)	C27—C26—N4—N3	−178.8 (4)
C8—C11—C12—C17	134.8 (5)	C24—N3—N4—C26	2.8 (5)
C17—C12—C13—C14	0.5 (8)	C18—N3—N4—C26	−180.0 (4)
C11—C12—C13—C14	−174.0 (5)	N3—C24—O1—U1	−142.0 (4)
C12—C13—C14—C15	−1.6 (8)	C25—C24—O1—U1	39.7 (6)
C13—C14—C15—C16	1.3 (8)	C8—C11—O2—U1	−12.4 (7)
C14—C15—C16—C17	0.1 (8)	C12—C11—O2—U1	171.3 (3)
C15—C16—C17—C12	−1.3 (8)	N1—C7—O3—U1	−144.5 (4)
C13—C12—C17—C16	1.0 (7)	C8—C7—O3—U1	37.9 (6)
C11—C12—C17—C16	175.5 (5)	C25—C28—O4—U1	−11.9 (7)
C23—C18—C19—C20	−1.8 (8)	C29—C28—O4—U1	170.5 (3)
N3—C18—C19—C20	179.8 (5)	C24—O1—U1—O6	−131.8 (3)
C18—C19—C20—C21	1.2 (8)	C24—O1—U1—O5	48.3 (3)
C19—C20—C21—C22	0.1 (9)	C24—O1—U1—O4	−40.3 (3)
C20—C21—C22—C23	−0.8 (9)	C24—O1—U1—O2	139.0 (4)
C21—C22—C23—C18	0.1 (8)	C24—O1—U1—O3	132.6 (3)
C19—C18—C23—C22	1.2 (8)	C24—O1—U1—O7	−39.1 (4)
N3—C18—C23—C22	179.7 (5)	C28—O4—U1—O6	123.7 (4)
O1—C24—C25—C28	−1.6 (8)	C28—O4—U1—O5	−57.9 (4)
N3—C24—C25—C28	179.8 (4)	C28—O4—U1—O1	31.7 (4)
O1—C24—C25—C26	−179.4 (5)	C28—O4—U1—O2	30.5 (5)
N3—C24—C25—C26	2.0 (5)	C28—O4—U1—O3	−141.6 (4)
C28—C25—C26—N4	−177.8 (5)	C28—O4—U1—O7	−147.6 (5)
C24—C25—C26—N4	−0.3 (6)	C11—O2—U1—O6	126.2 (4)
C28—C25—C26—C27	−0.8 (9)	C11—O2—U1—O5	−52.2 (4)
C24—C25—C26—C27	176.7 (5)	C11—O2—U1—O1	−141.2 (5)
C24—C25—C28—O4	−14.2 (7)	C11—O2—U1—O4	−139.9 (4)
C26—C25—C28—O4	162.8 (5)	C11—O2—U1—O3	35.0 (4)
C24—C25—C28—C29	163.3 (4)	C11—O2—U1—O7	37.1 (5)
C26—C25—C28—C29	−19.7 (8)	C7—O3—U1—O6	−133.2 (4)
O4—C28—C29—C30	−42.5 (7)	C7—O3—U1—O5	47.7 (4)
C25—C28—C29—C30	139.9 (5)	C7—O3—U1—O1	−37.1 (4)
O4—C28—C29—C34	132.2 (5)	C7—O3—U1—O4	131.8 (3)
C25—C28—C29—C34	−45.4 (7)	C7—O3—U1—O2	−43.6 (3)
C34—C29—C30—C31	1.4 (8)	C7—O3—U1—O7	137.8 (4)
C28—C29—C30—C31	176.2 (5)	C35—O7—U1—O6	49.0 (4)
C29—C30—C31—C32	−0.3 (8)	C35—O7—U1—O5	−132.1 (4)
C30—C31—C32—C33	−1.2 (8)	C35—O7—U1—O1	−44.6 (5)
C31—C32—C33—C34	1.5 (8)	C35—O7—U1—O4	−43.5 (4)
C30—C29—C34—C33	−1.1 (7)	C35—O7—U1—O2	138.3 (4)
C28—C29—C34—C33	−175.8 (4)	C35—O7—U1—O3	140.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7O···O36Si	0.81 (2)	1.84 (5)	2.633 (6)	168 (5)
O36S—H36S···N2ii	0.82	2.12	2.878 (6)	153
C6—H6···O3	0.93	2.33	2.909 (7)	120
C19—H19···O1	0.93	2.54	2.989 (7)	110

Table 1

Selected bond lengths (Å)

O1—U1	2.334 (3)
O2—U1	2.388 (3)
O3—U1	2.391 (3)
O4—U1	2.388 (3)
O5—U1	1.768 (3)
O6—U1	1.761 (3)
O7—U1	2.456 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7O⋯O36Si	0.81 (2)	1.84 (5)	2.633 (6)	168 (5)
O36S—H36S⋯N2ii	0.82	2.12	2.878 (6)	153
C6—H6⋯O3	0.93	2.33	2.909 (7)	120
C19—H19⋯O1	0.93	2.54	2.989 (7)	110

Symmetry codes: (i) ; (ii) .