2,2'-Iminobis(ethanaminium) (p-methyl­dihomooxacalix[4]arene)dioxouranium methanol disolvate monohydrate

In the title compound, (C₄H₁₅N₃)[UO₂(C₃₃H₃₀O₅)]·2CH₃OH·H₂O, the uranyl ion is bound to the four phenoxide groups of the deprotonated p-methyl­dihomooxacalix[4]arene in the usual cone conformation, giving a dianionic complex. The diprotonated diethyl­enetriamine counter-ion links neighbouring complex anions along the b axis through hydrogen bonding with the oxo, phenoxide and ether groups. The solvent mol­ecules are also involved in hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.024
• wR factor = 0.059
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O10    -   H10B   ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3C    ..  O6      ..       2.61 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999) and PLATON (Spek, 2003).

diethylenetriamine(2+) (p-methyldihomooxacalix[4]arene)dioxouranium methanol disolvate monohydrate

Crystal data

(C4H15N3)[UO2(C33H30O5)]·2CH4O·H2O	F(000) = 1928
Mr = 963.89	Dx = 1.609 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 131799 reflections
a = 11.9895 (4) Å	θ = 2.2–25.7°
b = 16.2079 (3) Å	µ = 4.14 mm^−1
c = 21.2475 (6) Å	T = 100 K
β = 105.441 (2)°	Platelet, translucent light orange
V = 3979.88 (19) Å^3	0.21 × 0.15 × 0.07 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	7565 independent reflections
Radiation source: fine-focus sealed tube	6173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
two φ and four ω scans with 2° steps	θmax = 25.7°, θmin = 2.2°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −14→14
Tmin = 0.528, Tmax = 0.749	k = −19→19
131799 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0321P)^2] where P = (Fo^2 + 2Fc^2)/3
7565 reflections	(Δ/σ)max = 0.001
484 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −1.00 e Å^−3

Special details

Experimental. crystal-to-detector distance 30 mm

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

Refinement. Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to N and O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, OH, CH, CH₂) or 1.5 (CH₃) times that of the parent atom. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
U1	0.677598 (9)	0.625673 (7)	0.187022 (5)	0.02124 (5)
O1	0.76745 (18)	0.67694 (12)	0.11436 (10)	0.0244 (5)
O2	0.84197 (18)	0.55225 (12)	0.22779 (10)	0.0223 (5)
O3	0.62669 (18)	0.55593 (12)	0.26763 (10)	0.0235 (5)
O4	0.49581 (18)	0.68030 (12)	0.16470 (10)	0.0236 (5)
O5	0.62143 (17)	0.82913 (13)	0.13096 (10)	0.0239 (5)
O6	0.62086 (18)	0.54278 (12)	0.13122 (10)	0.0258 (5)
O7	0.73486 (18)	0.70749 (12)	0.24246 (10)	0.0235 (5)
O8	0.7838 (2)	0.61700 (15)	−0.00367 (12)	0.0403 (6)
H8	0.7803	0.6346	0.0343	0.048*
O9	0.35380 (19)	0.58340 (14)	0.07575 (11)	0.0334 (5)
H9	0.3951	0.6179	0.0998	0.040*
O10	0.5316 (2)	0.40786 (14)	0.22347 (11)	0.0339 (5)
H10A	0.5563	0.4574	0.2467	0.041*
H10B	0.5263	0.3778	0.2550	0.041*
N1	0.8569 (2)	0.81579 (16)	0.38767 (12)	0.0257 (6)
H1	0.8392	0.7644	0.3722	0.031*
N2	0.7175 (2)	0.88604 (15)	0.27099 (12)	0.0252 (6)
H2A	0.6917	0.8651	0.2315	0.030*
H2B	0.7920	0.8792	0.2838	0.030*
H2C	0.7052	0.9422	0.2686	0.030*
N3	1.0640 (2)	0.91990 (17)	0.41588 (13)	0.0293 (6)
H3A	1.0233	0.9049	0.3719	0.035*
H3B	1.1258	0.8968	0.4197	0.035*
H3C	1.0837	0.9780	0.4164	0.035*
C1	0.8010 (3)	0.82014 (19)	0.10236 (14)	0.0223 (7)
C2	0.8425 (3)	0.74063 (18)	0.12380 (14)	0.0225 (7)
C3	0.9620 (3)	0.72857 (19)	0.15209 (14)	0.0230 (7)
C4	1.0362 (3)	0.79468 (19)	0.15338 (15)	0.0267 (7)
H4	1.1150	0.7867	0.1715	0.032*
C5	0.9980 (3)	0.8724 (2)	0.12873 (15)	0.0277 (7)
C6	0.8786 (3)	0.88410 (19)	0.10475 (15)	0.0255 (7)
H6	0.8506	0.9361	0.0900	0.031*
C7	1.0807 (3)	0.9425 (2)	0.12823 (19)	0.0374 (8)
H7A	1.0633	0.9664	0.0854	0.056*
H7B	1.1586	0.9220	0.1398	0.056*
H7C	1.0726	0.9838	0.1592	0.056*
C8	1.0079 (3)	0.64416 (19)	0.17957 (15)	0.0251 (7)
H8A	0.9580	0.6017	0.1548	0.030*
H8B	1.0845	0.6364	0.1733	0.030*
C9	1.0149 (3)	0.63286 (19)	0.25192 (15)	0.0241 (7)
C10	0.9310 (3)	0.58834 (19)	0.27263 (15)	0.0230 (7)
C11	0.9375 (3)	0.58201 (19)	0.33982 (15)	0.0239 (7)
C12	1.0329 (3)	0.61584 (19)	0.38469 (16)	0.0286 (7)
H12	1.0388	0.6104	0.4290	0.034*
C13	1.1198 (3)	0.6576 (2)	0.36545 (16)	0.0309 (8)
C14	1.1078 (3)	0.6666 (2)	0.29893 (16)	0.0303 (8)
H14	1.1636	0.6961	0.2853	0.036*
C15	1.2258 (3)	0.6895 (3)	0.41522 (17)	0.0434 (10)
H15A	1.2840	0.6473	0.4249	0.065*
H15B	1.2053	0.7046	0.4544	0.065*
H15C	1.2552	0.7370	0.3979	0.065*
C16	0.8457 (3)	0.53629 (19)	0.36423 (15)	0.0236 (7)
H16A	0.8137	0.4931	0.3331	0.028*
H16B	0.8840	0.5096	0.4051	0.028*
C17	0.7455 (3)	0.58680 (19)	0.37518 (15)	0.0228 (7)
C18	0.6400 (3)	0.59314 (18)	0.32635 (14)	0.0211 (6)
C19	0.5463 (3)	0.63793 (18)	0.33831 (15)	0.0245 (7)
C20	0.5603 (3)	0.67364 (19)	0.39930 (16)	0.0272 (7)
H20	0.4990	0.7031	0.4074	0.033*
C21	0.6633 (3)	0.66700 (19)	0.44914 (15)	0.0255 (7)
C22	0.7544 (3)	0.62394 (18)	0.43542 (15)	0.0243 (7)
H22	0.8239	0.6198	0.4677	0.029*
C23	0.6756 (3)	0.7049 (2)	0.51545 (16)	0.0343 (8)
H23A	0.7199	0.7549	0.5191	0.052*
H23B	0.7145	0.6668	0.5487	0.052*
H23C	0.6004	0.7171	0.5208	0.052*
C24	0.4329 (3)	0.64648 (19)	0.28533 (15)	0.0253 (7)
H24A	0.4288	0.6033	0.2532	0.030*
H24B	0.3691	0.6384	0.3047	0.030*
C25	0.4187 (3)	0.72948 (19)	0.25111 (15)	0.0233 (7)
C26	0.4554 (3)	0.74287 (19)	0.19435 (15)	0.0241 (7)
C27	0.4500 (3)	0.82311 (19)	0.16759 (15)	0.0223 (7)
C28	0.4046 (3)	0.88776 (19)	0.19626 (15)	0.0254 (7)
H28	0.4017	0.9404	0.1785	0.031*
C29	0.3634 (3)	0.87514 (19)	0.25072 (16)	0.0278 (7)
C30	0.3722 (3)	0.79603 (19)	0.27682 (15)	0.0259 (7)
H30	0.3454	0.7871	0.3135	0.031*
C31	0.3158 (3)	0.9456 (2)	0.28258 (17)	0.0336 (8)
H31A	0.2439	0.9292	0.2906	0.050*
H31B	0.3031	0.9927	0.2541	0.050*
H31C	0.3702	0.9597	0.3232	0.050*
C32	0.4969 (3)	0.8365 (2)	0.10997 (15)	0.0247 (7)
H32A	0.4652	0.7957	0.0766	0.030*
H32B	0.4754	0.8909	0.0917	0.030*
C33	0.6730 (3)	0.83217 (19)	0.07704 (14)	0.0234 (7)
H33A	0.6570	0.8851	0.0551	0.028*
H33B	0.6404	0.7892	0.0458	0.028*
C34	0.7488 (3)	0.85776 (19)	0.38811 (15)	0.0260 (7)
H34A	0.7641	0.9154	0.3994	0.031*
H34B	0.7157	0.8327	0.4205	0.031*
C35	0.6652 (3)	0.8507 (2)	0.32137 (16)	0.0270 (7)
H35A	0.6459	0.7932	0.3115	0.032*
H35B	0.5944	0.8801	0.3208	0.032*
C36	0.9432 (3)	0.8156 (2)	0.45108 (16)	0.0302 (8)
H36A	1.0016	0.7742	0.4510	0.036*
H36B	0.9062	0.8014	0.4850	0.036*
C37	1.0001 (3)	0.8992 (2)	0.46540 (15)	0.0280 (7)
H37A	0.9416	0.9408	0.4646	0.034*
H37B	1.0534	0.8989	0.5087	0.034*
C38	0.8989 (3)	0.6298 (3)	−0.0062 (2)	0.0522 (11)
H38A	0.9218	0.6853	0.0069	0.078*
H38B	0.9041	0.6209	−0.0500	0.078*
H38C	0.9490	0.5918	0.0227	0.078*
C39	0.2453 (3)	0.5829 (3)	0.0899 (2)	0.0486 (10)
H39A	0.2537	0.5599	0.1326	0.073*
H39B	0.1918	0.5501	0.0581	0.073*
H39C	0.2167	0.6383	0.0889	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
U1	0.02394 (7)	0.01933 (7)	0.01998 (7)	−0.00008 (5)	0.00504 (5)	−0.00163 (5)
O1	0.0246 (11)	0.0253 (11)	0.0233 (11)	−0.0018 (9)	0.0064 (9)	0.0005 (9)
O2	0.0242 (11)	0.0205 (11)	0.0215 (11)	−0.0005 (9)	0.0049 (9)	−0.0019 (9)
O3	0.0286 (12)	0.0210 (11)	0.0215 (11)	−0.0046 (9)	0.0078 (9)	−0.0020 (9)
O4	0.0234 (11)	0.0221 (11)	0.0252 (11)	0.0028 (9)	0.0065 (9)	−0.0022 (9)
O5	0.0199 (11)	0.0324 (12)	0.0186 (11)	0.0003 (9)	0.0035 (9)	−0.0020 (9)
O6	0.0291 (12)	0.0219 (11)	0.0259 (12)	−0.0001 (9)	0.0067 (10)	−0.0020 (9)
O7	0.0279 (12)	0.0200 (11)	0.0229 (11)	0.0008 (9)	0.0074 (9)	−0.0005 (9)
O8	0.0335 (13)	0.0562 (17)	0.0299 (13)	−0.0053 (12)	0.0062 (11)	−0.0113 (12)
O9	0.0263 (12)	0.0367 (13)	0.0360 (13)	−0.0015 (11)	0.0062 (10)	−0.0104 (11)
O10	0.0474 (15)	0.0301 (12)	0.0244 (12)	−0.0093 (11)	0.0102 (11)	−0.0022 (10)
N1	0.0277 (15)	0.0221 (13)	0.0262 (14)	0.0014 (11)	0.0050 (12)	0.0003 (11)
N2	0.0280 (14)	0.0234 (14)	0.0215 (13)	0.0002 (11)	0.0018 (11)	−0.0007 (11)
N3	0.0271 (15)	0.0311 (15)	0.0275 (15)	0.0010 (12)	0.0032 (12)	0.0036 (12)
C1	0.0248 (16)	0.0255 (16)	0.0174 (15)	−0.0007 (13)	0.0070 (13)	−0.0017 (12)
C2	0.0296 (17)	0.0210 (15)	0.0179 (15)	0.0004 (13)	0.0077 (13)	−0.0014 (12)
C3	0.0249 (16)	0.0270 (17)	0.0178 (15)	0.0002 (13)	0.0069 (13)	−0.0027 (13)
C4	0.0265 (17)	0.0297 (17)	0.0236 (16)	0.0045 (14)	0.0063 (13)	−0.0021 (14)
C5	0.0279 (17)	0.0300 (18)	0.0261 (16)	−0.0022 (15)	0.0090 (13)	−0.0038 (14)
C6	0.0287 (17)	0.0244 (16)	0.0250 (16)	0.0036 (14)	0.0102 (13)	0.0001 (13)
C7	0.032 (2)	0.0303 (18)	0.050 (2)	−0.0030 (15)	0.0116 (17)	−0.0035 (17)
C8	0.0235 (16)	0.0265 (17)	0.0268 (17)	0.0063 (13)	0.0093 (13)	0.0036 (13)
C9	0.0206 (15)	0.0269 (17)	0.0247 (16)	0.0055 (13)	0.0059 (12)	0.0003 (13)
C10	0.0220 (16)	0.0204 (15)	0.0255 (16)	0.0053 (13)	0.0043 (13)	−0.0021 (13)
C11	0.0243 (16)	0.0236 (16)	0.0227 (16)	0.0045 (13)	0.0045 (13)	0.0019 (13)
C12	0.0283 (17)	0.0323 (18)	0.0233 (16)	0.0038 (15)	0.0035 (13)	0.0014 (14)
C13	0.0255 (18)	0.0401 (19)	0.0259 (17)	0.0004 (15)	0.0050 (14)	−0.0033 (15)
C14	0.0236 (17)	0.038 (2)	0.0307 (18)	0.0008 (15)	0.0092 (14)	0.0008 (15)
C15	0.031 (2)	0.067 (3)	0.031 (2)	−0.0115 (19)	0.0063 (16)	−0.0041 (19)
C16	0.0271 (17)	0.0239 (16)	0.0195 (15)	0.0020 (14)	0.0057 (13)	0.0018 (13)
C17	0.0272 (17)	0.0204 (15)	0.0232 (16)	−0.0021 (13)	0.0109 (13)	0.0030 (13)
C18	0.0264 (16)	0.0171 (14)	0.0211 (15)	−0.0037 (13)	0.0087 (13)	−0.0001 (12)
C19	0.0293 (17)	0.0193 (16)	0.0258 (16)	−0.0050 (13)	0.0090 (13)	0.0008 (13)
C20	0.0279 (17)	0.0261 (17)	0.0304 (17)	0.0004 (14)	0.0124 (14)	0.0013 (14)
C21	0.0292 (17)	0.0246 (17)	0.0236 (16)	−0.0049 (14)	0.0086 (14)	−0.0019 (13)
C22	0.0261 (16)	0.0229 (16)	0.0237 (15)	−0.0031 (14)	0.0062 (13)	0.0015 (13)
C23	0.041 (2)	0.039 (2)	0.0249 (17)	−0.0006 (17)	0.0114 (15)	−0.0054 (15)
C24	0.0227 (16)	0.0265 (17)	0.0281 (17)	−0.0001 (13)	0.0092 (13)	−0.0004 (13)
C25	0.0170 (15)	0.0269 (16)	0.0248 (16)	−0.0028 (13)	0.0032 (13)	−0.0009 (13)
C26	0.0179 (15)	0.0279 (17)	0.0251 (16)	−0.0012 (13)	0.0032 (13)	−0.0065 (13)
C27	0.0169 (15)	0.0253 (16)	0.0226 (15)	−0.0005 (13)	0.0014 (12)	−0.0014 (13)
C28	0.0202 (15)	0.0246 (17)	0.0276 (16)	0.0010 (13)	−0.0004 (13)	0.0019 (13)
C29	0.0224 (16)	0.0282 (17)	0.0326 (17)	−0.0019 (14)	0.0074 (13)	−0.0055 (15)
C30	0.0209 (16)	0.0313 (18)	0.0261 (16)	−0.0042 (14)	0.0074 (13)	−0.0033 (14)
C31	0.0342 (19)	0.0320 (19)	0.037 (2)	0.0040 (15)	0.0133 (16)	−0.0040 (16)
C32	0.0198 (16)	0.0267 (16)	0.0240 (16)	−0.0003 (13)	−0.0004 (13)	−0.0010 (13)
C33	0.0273 (17)	0.0259 (16)	0.0177 (15)	0.0014 (14)	0.0073 (13)	−0.0007 (13)
C34	0.0298 (17)	0.0233 (17)	0.0247 (16)	−0.0014 (13)	0.0073 (14)	0.0008 (13)
C35	0.0245 (17)	0.0250 (16)	0.0326 (18)	−0.0037 (13)	0.0093 (14)	−0.0019 (14)
C36	0.0354 (19)	0.0250 (17)	0.0277 (17)	0.0043 (15)	0.0042 (14)	0.0070 (14)
C37	0.0277 (17)	0.0319 (18)	0.0223 (16)	0.0003 (14)	0.0031 (13)	0.0017 (14)
C38	0.036 (2)	0.082 (3)	0.039 (2)	−0.003 (2)	0.0098 (17)	−0.014 (2)
C39	0.036 (2)	0.043 (2)	0.070 (3)	−0.0002 (18)	0.021 (2)	0.008 (2)

Geometric parameters (Å, º)

U1—O1	2.263 (2)	C15—H15A	0.9600
U1—O2	2.267 (2)	C15—H15B	0.9600
U1—O3	2.267 (2)	C15—H15C	0.9600
U1—O4	2.282 (2)	C16—C17	1.521 (4)
U1—O6	1.801 (2)	C16—H16A	0.9700
U1—O7	1.785 (2)	C16—H16B	0.9700
O1—C2	1.349 (4)	C17—C22	1.393 (4)
O2—C10	1.359 (4)	C17—C18	1.410 (4)
O3—C18	1.356 (3)	C18—C19	1.417 (4)
O4—C26	1.350 (4)	C19—C20	1.388 (4)
O5—C33	1.440 (4)	C19—C24	1.523 (4)
O5—C32	1.445 (4)	C20—C21	1.400 (4)
O8—C38	1.410 (4)	C20—H20	0.9300
O8—H8	0.8684	C21—C22	1.391 (4)
O9—C39	1.411 (4)	C21—C23	1.508 (4)
O9—H9	0.8273	C22—H22	0.9300
O10—H10A	0.9472	C23—H23A	0.9600
O10—H10B	0.8444	C23—H23B	0.9600
N1—C36	1.464 (4)	C23—H23C	0.9600
N1—C34	1.466 (4)	C24—C25	1.517 (4)
N1—H1	0.9006	C24—H24A	0.9700
N2—C35	1.491 (4)	C24—H24B	0.9700
N2—H2A	0.8813	C25—C30	1.391 (4)
N2—H2B	0.8689	C25—C26	1.407 (4)
N2—H2C	0.9215	C26—C27	1.414 (4)
N3—C37	1.496 (4)	C27—C28	1.394 (4)
N3—H3A	0.9625	C27—C32	1.493 (4)
N3—H3B	0.8148	C28—C29	1.389 (5)
N3—H3C	0.9705	C28—H28	0.9300
C1—C6	1.384 (4)	C29—C30	1.390 (4)
C1—C2	1.412 (4)	C29—C31	1.515 (4)
C1—C33	1.498 (4)	C30—H30	0.9300
C2—C3	1.411 (4)	C31—H31A	0.9600
C3—C4	1.388 (4)	C31—H31B	0.9600
C3—C8	1.531 (4)	C31—H31C	0.9600
C4—C5	1.395 (4)	C32—H32A	0.9700
C4—H4	0.9300	C32—H32B	0.9700
C5—C6	1.399 (4)	C33—H33A	0.9700
C5—C7	1.510 (4)	C33—H33B	0.9700
C6—H6	0.9300	C34—C35	1.507 (4)
C7—H7A	0.9600	C34—H34A	0.9700
C7—H7B	0.9600	C34—H34B	0.9700
C7—H7C	0.9600	C35—H35A	0.9700
C8—C9	1.528 (4)	C35—H35B	0.9700
C8—H8A	0.9700	C36—C37	1.511 (4)
C8—H8B	0.9700	C36—H36A	0.9700
C9—C14	1.394 (4)	C36—H36B	0.9700
C9—C10	1.401 (4)	C37—H37A	0.9700
C10—C11	1.412 (4)	C37—H37B	0.9700
C11—C12	1.392 (4)	C38—H38A	0.9600
C11—C16	1.528 (4)	C38—H38B	0.9600
C12—C13	1.392 (5)	C38—H38C	0.9600
C12—H12	0.9300	C39—H39A	0.9600
C13—C14	1.390 (5)	C39—H39B	0.9600
C13—C15	1.511 (5)	C39—H39C	0.9600
C14—H14	0.9300
O1—U1—O2	85.99 (7)	C18—C17—C16	121.1 (3)
O2—U1—O3	80.28 (7)	O3—C18—C17	120.5 (3)
O3—U1—O4	85.19 (8)	O3—C18—C19	119.2 (3)
O4—U1—O1	108.51 (7)	C17—C18—C19	120.3 (3)
O6—U1—O7	179.58 (10)	C20—C19—C18	118.5 (3)
O7—U1—O1	90.47 (8)	C20—C19—C24	121.0 (3)
O6—U1—O1	89.41 (9)	C18—C19—C24	120.6 (3)
O7—U1—O3	90.31 (8)	C19—C20—C21	122.5 (3)
O6—U1—O3	89.71 (8)	C19—C20—H20	118.8
O1—U1—O3	166.25 (8)	C21—C20—H20	118.8
O7—U1—O2	89.73 (9)	C22—C21—C20	117.6 (3)
O6—U1—O2	89.85 (8)	C22—C21—C23	120.9 (3)
O7—U1—O4	91.56 (8)	C20—C21—C23	121.5 (3)
O6—U1—O4	88.87 (8)	C21—C22—C17	122.5 (3)
O2—U1—O4	165.42 (8)	C21—C22—H22	118.7
C2—O1—U1	126.84 (18)	C17—C22—H22	118.7
C10—O2—U1	118.84 (17)	C21—C23—H23A	109.5
C18—O3—U1	118.93 (17)	C21—C23—H23B	109.5
C26—O4—U1	129.49 (18)	H23A—C23—H23B	109.5
C33—O5—C32	112.3 (2)	C21—C23—H23C	109.5
C38—O8—H8	106.1	H23A—C23—H23C	109.5
C39—O9—H9	107.8	H23B—C23—H23C	109.5
H10A—O10—H10B	98.9	C25—C24—C19	113.5 (3)
C36—N1—C34	113.9 (3)	C25—C24—H24A	108.9
C36—N1—H1	111.9	C19—C24—H24A	108.9
C34—N1—H1	108.0	C25—C24—H24B	108.9
C35—N2—H2A	115.3	C19—C24—H24B	108.9
C35—N2—H2B	108.6	H24A—C24—H24B	107.7
H2A—N2—H2B	108.7	C30—C25—C26	117.8 (3)
C35—N2—H2C	109.1	C30—C25—C24	120.3 (3)
H2A—N2—H2C	108.6	C26—C25—C24	121.8 (3)
H2B—N2—H2C	106.2	O4—C26—C25	121.2 (3)
C37—N3—H3A	113.8	O4—C26—C27	119.2 (3)
C37—N3—H3B	116.7	C25—C26—C27	119.7 (3)
H3A—N3—H3B	101.2	C28—C27—C26	119.8 (3)
C37—N3—H3C	112.3	C28—C27—C32	121.7 (3)
H3A—N3—H3C	108.4	C26—C27—C32	118.4 (3)
H3B—N3—H3C	103.5	C29—C28—C27	121.3 (3)
C6—C1—C2	119.7 (3)	C29—C28—H28	119.3
C6—C1—C33	122.0 (3)	C27—C28—H28	119.3
C2—C1—C33	118.3 (3)	C28—C29—C30	117.6 (3)
O1—C2—C3	121.2 (3)	C28—C29—C31	121.4 (3)
O1—C2—C1	119.1 (3)	C30—C29—C31	121.0 (3)
C3—C2—C1	119.6 (3)	C29—C30—C25	123.7 (3)
C4—C3—C2	118.3 (3)	C29—C30—H30	118.2
C4—C3—C8	121.2 (3)	C25—C30—H30	118.2
C2—C3—C8	120.5 (3)	C29—C31—H31A	109.5
C3—C4—C5	123.0 (3)	C29—C31—H31B	109.5
C3—C4—H4	118.5	H31A—C31—H31B	109.5
C5—C4—H4	118.5	C29—C31—H31C	109.5
C4—C5—C6	117.5 (3)	H31A—C31—H31C	109.5
C4—C5—C7	122.1 (3)	H31B—C31—H31C	109.5
C6—C5—C7	120.4 (3)	O5—C32—C27	108.6 (2)
C1—C6—C5	121.6 (3)	O5—C32—H32A	110.0
C1—C6—H6	119.2	C27—C32—H32A	110.0
C5—C6—H6	119.2	O5—C32—H32B	110.0
C5—C7—H7A	109.5	C27—C32—H32B	110.0
C5—C7—H7B	109.5	H32A—C32—H32B	108.3
H7A—C7—H7B	109.5	O5—C33—C1	109.0 (2)
C5—C7—H7C	109.5	O5—C33—H33A	109.9
H7A—C7—H7C	109.5	C1—C33—H33A	109.9
H7B—C7—H7C	109.5	O5—C33—H33B	109.9
C9—C8—C3	114.1 (3)	C1—C33—H33B	109.9
C9—C8—H8A	108.7	H33A—C33—H33B	108.3
C3—C8—H8A	108.7	N1—C34—C35	109.1 (3)
C9—C8—H8B	108.7	N1—C34—H34A	109.9
C3—C8—H8B	108.7	C35—C34—H34A	109.9
H8A—C8—H8B	107.6	N1—C34—H34B	109.9
C14—C9—C10	118.7 (3)	C35—C34—H34B	109.9
C14—C9—C8	119.6 (3)	H34A—C34—H34B	108.3
C10—C9—C8	121.7 (3)	N2—C35—C34	110.2 (3)
O2—C10—C9	119.8 (3)	N2—C35—H35A	109.6
O2—C10—C11	119.9 (3)	C34—C35—H35A	109.6
C9—C10—C11	120.2 (3)	N2—C35—H35B	109.6
C12—C11—C10	118.6 (3)	C34—C35—H35B	109.6
C12—C11—C16	119.6 (3)	H35A—C35—H35B	108.1
C10—C11—C16	121.8 (3)	N1—C36—C37	110.7 (3)
C11—C12—C13	122.2 (3)	N1—C36—H36A	109.5
C11—C12—H12	118.9	C37—C36—H36A	109.5
C13—C12—H12	118.9	N1—C36—H36B	109.5
C14—C13—C12	117.8 (3)	C37—C36—H36B	109.5
C14—C13—C15	121.1 (3)	H36A—C36—H36B	108.1
C12—C13—C15	121.1 (3)	N3—C37—C36	110.4 (3)
C13—C14—C9	122.3 (3)	N3—C37—H37A	109.6
C13—C14—H14	118.8	C36—C37—H37A	109.6
C9—C14—H14	118.8	N3—C37—H37B	109.6
C13—C15—H15A	109.5	C36—C37—H37B	109.6
C13—C15—H15B	109.5	H37A—C37—H37B	108.1
H15A—C15—H15B	109.5	O8—C38—H38A	109.5
C13—C15—H15C	109.5	O8—C38—H38B	109.5
H15A—C15—H15C	109.5	H38A—C38—H38B	109.5
H15B—C15—H15C	109.5	O8—C38—H38C	109.5
C17—C16—C11	117.4 (3)	H38A—C38—H38C	109.5
C17—C16—H16A	107.9	H38B—C38—H38C	109.5
C11—C16—H16A	107.9	O9—C39—H39A	109.5
C17—C16—H16B	107.9	O9—C39—H39B	109.5
C11—C16—H16B	107.9	H39A—C39—H39B	109.5
H16A—C16—H16B	107.2	O9—C39—H39C	109.5
C22—C17—C18	118.6 (3)	H39A—C39—H39C	109.5
C22—C17—C16	120.2 (3)	H39B—C39—H39C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O1	0.87	1.88	2.745 (3)	177
O9—H9···O4	0.83	1.87	2.688 (3)	170
O10—H10A···O3	0.95	1.81	2.715 (3)	160
N2—H2B···N1	0.87	2.37	2.834 (4)	114
N2—H2A···O7	0.88	2.60	2.975 (3)	106
N2—H2A···O5	0.88	2.16	3.034 (3)	173
N2—H2C···O2^i	0.92	1.88	2.788 (3)	169
N2—H2B···O10^i	0.87	2.21	3.000 (4)	151
N3—H3A···N1	0.96	2.56	2.929 (4)	103
N3—H3C···O6^i	0.97	2.61	2.950 (3)	101
N3—H3B···O8^ii	0.81	2.16	2.797 (4)	136
N3—H3C···O9^i	0.97	1.85	2.816 (4)	170
N3—H3A···O10^i	0.96	1.96	2.883 (3)	160
O10—H10b···Cg^iii	0.84	2.67	3.47	160

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.