Aqua(N,N′,N′′,N′′′-tetrakis(2-hydroxy­ethyl)-1,4,7,10-tetr­aza­cyclo­do­decane)­praseodymium(III) hexanitratopraseodymate(III) dihydrate

Richards-Johnson, R.U.; Kahwa, I.A.; Lough, A.J.

doi:10.1107/S1600536803017458

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Aqua(N,N′,N′′,N′′′-tetrakis(2-hydroxyethyl)-1,4,7,10-tetrazacyclododecane)praseodymium(III) hexanitratopraseodymate(III) dihydrate

R. U. Richards-Johnson, I. A. Kahwa and A. J. Lough

The title compound, [Pr(C₁₆H₃₆N₄O₄)(H₂O)][Pr(NO₃)₆]·2H₂O, was prepared as part of our search for polynuclear lanthanide(III) nanoclusters. The asymmetric unit contains two distinct metal sites, one in which the Pr³⁺ ion is in coordination number 12 and the other in coordination number 9. The cations, anions and water molecules are linked in the crystal structure by O—H

O hydrogen bonds

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017458/om6157sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017458/om6157Isup2.hkl Contains datablock I

CCDC reference: 222805

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.023
wR factor = 0.055
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .....       0.98

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ..          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O17    -   N6     =       5.25 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O2     =       5.33 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O4     =       6.78 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O5     =       5.40 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O7     =       6.63 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O8     =       5.98 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O10    =       8.44 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O11    =       6.13 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O13    =       5.93 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O14    =       9.27 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O16    =       9.34 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O17    =       6.61 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ......          4
PLAT755_ALERT_4_C D-H     Calc     0.83831, Rep     0.84(2) ....  Senseless su
              O23  -H23A    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.84214, Rep     0.84(2) ....  Senseless su
              O20  -H20     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.83887, Rep     0.84(2) ....  Senseless su
              O23  -H23B    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.83928, Rep     0.84(2) ....  Senseless su
              O1W  -H1WA    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.83906, Rep     0.84(2) ....  Senseless su
              O1W  -H1WB    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.83834, Rep     0.84(2) ....  Senseless su
              O22  -H22     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.83920, Rep     0.84(2) ....  Senseless su
              O21  -H21     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.84360, Rep     0.84(2) ....  Senseless su
              O19  -H19     1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.83926, Rep     0.84(2) ....  Senseless su
              O2W  -H2WA    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.84146, Rep     0.84(2) ....  Senseless su
              O2W  -H2WB    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.84146, Rep     0.84(2) ....  Senseless su
              O2W  -H2WB    1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.84146, Rep     0.84(2) ....  Senseless su
              O2W  -H2WB    1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.24212, Rep     2.24(2) ....  Senseless su
              H23A -O13     1.555   2.545
PLAT756_ALERT_4_C H...A   Calc     1.78285, Rep     1.79(2) ....  Senseless su
              H20  -O1W     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.01785, Rep     2.02(2) ....  Senseless su
              H23B -O17     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.05417, Rep     2.05(2) ....  Senseless su
              H1WA -O15     1.555   2.545
PLAT756_ALERT_4_C H...A   Calc     2.01813, Rep     2.02(2) ....  Senseless su
              H1WB -O11     1.555   4.566
PLAT756_ALERT_4_C H...A   Calc     1.77798, Rep     1.78(3) ....  Senseless su
              H22  -O2W     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     1.93223, Rep     1.93(2) ....  Senseless su
              H21  -O13     1.555   2.545
PLAT756_ALERT_4_C H...A   Calc     1.86978, Rep     1.87(2) ....  Senseless su
              H19  -O5      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.24190, Rep     2.24(2) ....  Senseless su
              H2WA -O3      1.555   4.666
PLAT756_ALERT_4_C H...A   Calc     2.42685, Rep     2.43(2) ....  Senseless su
              H2WB -O9      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.46488, Rep     2.46(2) ....  Senseless su
              H2WB -O7      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.49280, Rep     2.50(2) ....  Senseless su
              H2WB -O6      1.555   2.545
PLAT758_ALERT_4_C D-H..A  Calc      174.50, Rep      174(2) ....  Senseless su
              O20  -H20  -O1W     1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      164.38, Rep      164(2) ....  Senseless su
              O23  -H23B -O17     1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      165.76, Rep      166(2) ....  Senseless su
              O22  -H22  -O2W     1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      168.83, Rep      169(2) ....  Senseless su
              O19  -H19  -O5      1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      129.50, Rep      130(2) ....  Senseless su
              O2W  -H2WB -O9      1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      130.43, Rep      131(2) ....  Senseless su
              O2W  -H2WB -O7      1.555   1.555   1.555

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  44 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
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  31 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), was obtained from the templated oligomerization of 1-azirideneethanol. The reaction was carried out under basic conditions which also yielded insoluble hydroxides. Slow evaporation of the filtrate gave needle-like crystals. The Pr³⁺ ions are in two distinct environments (see Fig. 1). In the first case, Pr1 is coordinated to six bidentate nitrate ions, resulting in an icosahedral polyhedron with Pr³⁺ ions having a coordination number (CN) of 12. In the second case, Pr2 is encapsulated in the macrocycle N,N',N'',N'''-tetrakis(2-hydroxyethyl)-1,4,7,10-tetrazacyclododecane (H₄L), bonding to four tertiary amines and four alkoxides. The s tereochemistry of the chelate H₄L is Δ(δδδδ). Atom Pr2 achieves a CN of 9 by bonding to a water molecule. The crystal structure is linked by O—H···O hydrogen bonds involving water molecules and the alkoxide groups (see Table 2 and Fig. 2). The crystal structure of (I) is the same as that found previously for the La analogue (Thompson, 2001).

Experimental top

Pr(NO₃)3.nH₂O (5.03 mmol) was dissolved in 100 ml of anhydrous ethanol and added drop-wise to 2 mmol of 1-aziridineethanol in refluxing 50 ml of a 0.02 M solution of NaOH. Reflux was continued for about one week after which the reaction was filtered and slow evaporation of the filtrate yielded green needle-like crystals of (I) in ca 10% yield. Analysis calculated for C₁₆H₄₂N₁₀O₂₅Pr₂: C 18.19, H 4.14, N 13.10%; found: C 17.71, H 4.03, N 12.76%.

Computing details top

Data collection: COLLECT (Nonius, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of (I), showing the atom-labeling scheme, with ellipsoids drawn at the 30% probability level. H atoms and water molecules have been omitted.
	Fig. 2. View of the hydrogen bonding in (I) corresponding to Table 2. Ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1/2 − x, −1/2 + y, 1/2 − z; (ii) −1/2 + x, 1/2 − y, 1/2 + z; (iii) 1/2 + x, 1/2 − y, 1/2 + z.]
	Fig. 3. Packing diagram (Spek, 2003), viewed approximately along the b axis. Atom colours are as labeled in Fig. 1.

Aqua(N,N',N'',N'''-tetrakis(2-hydroxyethyl)-1,4,7,10- tetrazacyclododecane)praseodymium(III) hexanitratopraseodymate(III) dihydrate top

Crystal data top

[Pr(C₁₆H₃₆N₄O₄)(H₂O)][Pr(NO₃)₆]·2H₂O	F(000) = 2104
M_r = 1056.42	D_x = 2.028 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7809 reflections
a = 15.5786 (3) Å	θ = 2.6–27.5°
b = 14.4453 (3) Å	µ = 2.89 mm⁻¹
c = 15.5995 (3) Å	T = 150 K
β = 99.749 (1)°	Needle, green
V = 3459.78 (12) Å³	0.25 × 0.25 × 0.15 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	7950 independent reflections
Radiation source: fine-focus sealed tube	7143 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 9 pixels mm^-1	θ_max = 27.7°, θ_min = 3.0°
ϕ scans and ω scans with κ offsets	h = −20→20
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	k = −18→18
T_min = 0.516, T_max = 0.651	l = −20→19
27454 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.055	w = 1/[σ²(F_o²) + 2.2848P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.003
7950 reflections	Δρ_max = 1.29 e Å⁻³
519 parameters	Δρ_min = −0.73 e Å⁻³
10 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00094 (8)

Crystal data top

[Pr(C₁₆H₃₆N₄O₄)(H₂O)][Pr(NO₃)₆]·2H₂O	V = 3459.78 (12) Å³
M_r = 1056.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.5786 (3) Å	µ = 2.89 mm⁻¹
b = 14.4453 (3) Å	T = 150 K
c = 15.5995 (3) Å	0.25 × 0.25 × 0.15 mm
β = 99.749 (1)°

Data collection top

Nonius KappaCCD diffractometer	7950 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	7143 reflections with I > 2σ(I)
T_min = 0.516, T_max = 0.651	R_int = 0.027
27454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	10 restraints
wR(F²) = 0.055	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.29 e Å⁻³
7950 reflections	Δρ_min = −0.73 e Å⁻³
519 parameters

Special details top

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. 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 (Å²) top

	x	y	z	U_iso*/U_eq
Pr1	0.270460 (8)	0.305788 (9)	0.084035 (8)	0.01522 (5)
O1	0.22145 (12)	0.22456 (13)	−0.06762 (12)	0.0248 (4)
O2	0.11930 (12)	0.28642 (13)	−0.00793 (12)	0.0254 (4)
O3	0.08706 (14)	0.22242 (18)	−0.13522 (13)	0.0421 (6)
O4	0.15851 (12)	0.41964 (13)	0.12722 (11)	0.0249 (4)
O5	0.25938 (11)	0.37961 (12)	0.23314 (11)	0.0205 (4)
O6	0.15349 (15)	0.46815 (17)	0.25838 (13)	0.0440 (6)
O7	0.36139 (12)	0.20001 (12)	0.19763 (12)	0.0236 (4)
O8	0.39380 (12)	0.19300 (12)	0.06824 (12)	0.0239 (4)
O9	0.46479 (12)	0.10828 (13)	0.17232 (14)	0.0335 (5)
O10	0.23892 (12)	0.41581 (13)	−0.05463 (12)	0.0254 (4)
O11	0.36568 (11)	0.35064 (13)	−0.03204 (11)	0.0238 (4)
O12	0.32180 (13)	0.42374 (13)	−0.15414 (11)	0.0305 (4)
O13	0.33481 (11)	0.48311 (12)	0.10241 (11)	0.0222 (4)
O14	0.41926 (12)	0.37560 (12)	0.16497 (12)	0.0248 (4)
O15	0.46585 (12)	0.51728 (13)	0.16981 (14)	0.0325 (5)
O16	0.21242 (12)	0.13168 (12)	0.08448 (11)	0.0247 (4)
O17	0.17652 (11)	0.22005 (11)	0.18453 (11)	0.0205 (4)
O18	0.15631 (13)	0.07093 (12)	0.19041 (13)	0.0304 (4)
N1	0.14171 (15)	0.24354 (16)	−0.07150 (15)	0.0257 (5)
N2	0.18868 (14)	0.42432 (15)	0.20745 (14)	0.0236 (5)
N3	0.40802 (14)	0.16551 (14)	0.14679 (15)	0.0218 (5)
N4	0.30838 (14)	0.39779 (14)	−0.08228 (13)	0.0218 (5)
N5	0.40858 (13)	0.45930 (14)	0.14692 (13)	0.0208 (4)
N6	0.18113 (13)	0.13824 (14)	0.15364 (13)	0.0198 (4)
Pr2	0.263766 (8)	0.252754 (8)	0.512513 (8)	0.01379 (5)
O19	0.32362 (11)	0.34284 (13)	0.40165 (11)	0.0239 (4)
H19	0.297	0.355	0.3512	0.060 (12)*
O20	0.12683 (12)	0.31946 (12)	0.43661 (13)	0.0252 (4)
H20	0.0872	0.283	0.414	0.054 (11)*
O21	0.16336 (11)	0.12061 (12)	0.52086 (11)	0.0206 (4)
H21	0.161	0.0769	0.4851	0.044 (10)*
O22	0.36630 (12)	0.13051 (13)	0.48723 (11)	0.0238 (4)
H22	0.389	0.127	0.4423	0.050 (11)*
O23	0.21815 (14)	0.17606 (13)	0.36386 (12)	0.0275 (4)
H23A	0.208	0.1201	0.352	0.040 (10)*
H23B	0.203	0.199	0.3142	0.056 (12)*
N7	0.39700 (13)	0.36673 (14)	0.56845 (13)	0.0179 (4)
N8	0.21376 (13)	0.42023 (14)	0.57114 (13)	0.0191 (4)
N9	0.18713 (13)	0.23982 (13)	0.65357 (13)	0.0166 (4)
N10	0.37220 (13)	0.18512 (13)	0.65391 (13)	0.0162 (4)
C1	0.41078 (16)	0.37834 (19)	0.41216 (17)	0.0248 (6)
H1A	0.4097	0.4463	0.4036	0.030*
H1B	0.4424	0.3500	0.3688	0.030*
C2	0.45574 (16)	0.35485 (19)	0.50317 (16)	0.0226 (5)
H2A	0.4763	0.2899	0.5045	0.027*
H2B	0.5073	0.3953	0.5190	0.027*
C3	0.36873 (16)	0.46502 (17)	0.57034 (17)	0.0226 (5)
H3A	0.3552	0.4888	0.5100	0.027*
H3B	0.4172	0.5024	0.6020	0.027*
C4	0.28956 (17)	0.47648 (17)	0.61356 (17)	0.0237 (5)
H4A	0.3048	0.4580	0.6754	0.028*
H4B	0.2727	0.5426	0.6118	0.028*
C5	0.09467 (17)	0.41185 (18)	0.44321 (18)	0.0252 (6)
H5A	0.0447	0.4116	0.4748	0.030*
H5B	0.0751	0.4381	0.3845	0.030*
C6	0.16842 (17)	0.46897 (17)	0.49207 (17)	0.0239 (5)
H6A	0.2109	0.4827	0.4532	0.029*
H6B	0.1451	0.5286	0.5094	0.029*
C7	0.15279 (17)	0.40807 (17)	0.63375 (17)	0.0227 (5)
H7A	0.0938	0.3944	0.6014	0.027*
H7B	0.1496	0.4665	0.6662	0.027*
C8	0.18102 (17)	0.33048 (17)	0.69751 (16)	0.0206 (5)
H8A	0.2385	0.3459	0.7321	0.025*
H8B	0.1388	0.3251	0.7381	0.025*
C9	0.09682 (16)	0.20509 (17)	0.62361 (16)	0.0198 (5)
H9A	0.0634	0.2523	0.5858	0.024*
H9B	0.0678	0.1958	0.6747	0.024*
C10	0.09590 (16)	0.11508 (17)	0.57407 (16)	0.0200 (5)
H10A	0.1072	0.0624	0.6151	0.024*
H10B	0.0384	0.1057	0.5370	0.024*
C11	0.23535 (16)	0.17305 (17)	0.71689 (15)	0.0190 (5)
H11A	0.2251	0.1094	0.6940	0.023*
H11B	0.2127	0.1768	0.7724	0.023*
C12	0.33274 (16)	0.19253 (17)	0.73391 (16)	0.0192 (5)
H12A	0.3429	0.2556	0.7583	0.023*
H12B	0.3619	0.1481	0.7777	0.023*
C13	0.45642 (16)	0.23601 (17)	0.66624 (17)	0.0199 (5)
H13A	0.4915	0.2139	0.6230	0.024*
H13B	0.4893	0.2224	0.7249	0.024*
C14	0.44356 (16)	0.33935 (17)	0.65643 (16)	0.0213 (5)
H14A	0.4099	0.3615	0.7008	0.026*
H14B	0.5012	0.3701	0.6674	0.026*
C15	0.38698 (17)	0.08596 (17)	0.63622 (16)	0.0205 (5)
H15A	0.3320	0.0514	0.6356	0.025*
H15B	0.4308	0.0606	0.6838	0.025*
C16	0.41803 (17)	0.07113 (18)	0.55068 (16)	0.0223 (5)
H16A	0.4805	0.0872	0.5563	0.027*
H16B	0.4104	0.0055	0.5326	0.027*
O1W	0.00051 (13)	0.20477 (14)	0.37623 (13)	0.0271 (4)
H1WA	0.020	0.1522	0.367	0.038 (10)*
H1WB	−0.0401	0.195	0.4042	0.045 (11)*
O2W	0.46088 (16)	0.11367 (19)	0.36595 (15)	0.0415 (5)
H2WA	0.493	0.160	0.364	0.15 (3)*
H2WB	0.430	0.100	0.3180	0.093 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.01556 (8)	0.01593 (7)	0.01463 (8)	0.00102 (5)	0.00386 (5)	0.00002 (5)
O1	0.0227 (10)	0.0319 (10)	0.0203 (9)	−0.0033 (8)	0.0051 (7)	−0.0050 (8)
O2	0.0208 (9)	0.0348 (11)	0.0213 (9)	−0.0006 (8)	0.0051 (7)	−0.0029 (8)
O3	0.0292 (11)	0.0722 (16)	0.0228 (11)	−0.0217 (11)	−0.0013 (9)	−0.0093 (10)
O4	0.0259 (9)	0.0293 (10)	0.0192 (9)	0.0073 (8)	0.0029 (7)	−0.0005 (7)
O5	0.0223 (9)	0.0210 (9)	0.0181 (8)	0.0006 (7)	0.0030 (7)	0.0004 (7)
O6	0.0464 (13)	0.0584 (15)	0.0302 (11)	0.0219 (11)	0.0152 (10)	−0.0097 (10)
O7	0.0235 (9)	0.0250 (9)	0.0233 (9)	0.0034 (7)	0.0066 (8)	0.0030 (7)
O8	0.0238 (10)	0.0237 (9)	0.0256 (10)	0.0024 (7)	0.0083 (8)	0.0008 (7)
O9	0.0208 (9)	0.0272 (10)	0.0534 (13)	0.0078 (8)	0.0087 (9)	0.0135 (9)
O10	0.0235 (9)	0.0255 (10)	0.0269 (10)	0.0020 (8)	0.0037 (8)	0.0028 (8)
O11	0.0199 (9)	0.0298 (10)	0.0220 (9)	0.0004 (8)	0.0042 (7)	0.0040 (8)
O12	0.0427 (12)	0.0339 (11)	0.0144 (9)	−0.0132 (9)	0.0034 (8)	0.0033 (8)
O13	0.0219 (9)	0.0210 (9)	0.0233 (9)	0.0008 (7)	0.0030 (7)	0.0037 (7)
O14	0.0248 (10)	0.0171 (9)	0.0319 (10)	0.0029 (7)	0.0033 (8)	0.0012 (7)
O15	0.0232 (10)	0.0253 (10)	0.0491 (13)	−0.0078 (8)	0.0064 (9)	−0.0068 (9)
O16	0.0307 (10)	0.0226 (9)	0.0227 (9)	0.0016 (8)	0.0097 (8)	−0.0048 (7)
O17	0.0263 (10)	0.0141 (8)	0.0221 (9)	−0.0002 (7)	0.0072 (7)	−0.0027 (7)
O18	0.0361 (11)	0.0197 (9)	0.0372 (11)	−0.0063 (8)	0.0119 (9)	0.0036 (8)
N1	0.0242 (12)	0.0336 (13)	0.0194 (11)	−0.0094 (9)	0.0043 (10)	0.0002 (9)
N2	0.0261 (11)	0.0240 (11)	0.0223 (11)	0.0041 (9)	0.0087 (9)	−0.0002 (9)
N3	0.0177 (10)	0.0158 (10)	0.0319 (12)	−0.0016 (8)	0.0042 (9)	0.0027 (9)
N4	0.0272 (12)	0.0195 (11)	0.0180 (11)	−0.0072 (9)	0.0015 (9)	−0.0015 (8)
N5	0.0200 (10)	0.0207 (11)	0.0231 (11)	−0.0011 (8)	0.0081 (9)	−0.0031 (8)
N6	0.0158 (10)	0.0191 (10)	0.0243 (11)	−0.0013 (8)	0.0032 (8)	0.0005 (9)
Pr2	0.01328 (8)	0.01476 (8)	0.01358 (8)	−0.00021 (4)	0.00302 (5)	0.00062 (4)
O19	0.0199 (9)	0.0321 (10)	0.0198 (9)	−0.0048 (8)	0.0036 (7)	0.0073 (8)
O20	0.0196 (9)	0.0204 (9)	0.0335 (11)	0.0023 (7)	−0.0015 (8)	0.0010 (8)
O21	0.0233 (9)	0.0180 (9)	0.0225 (9)	−0.0032 (7)	0.0094 (7)	−0.0048 (7)
O22	0.0257 (10)	0.0288 (10)	0.0176 (9)	0.0084 (8)	0.0051 (7)	0.0001 (8)
O23	0.0411 (12)	0.0244 (10)	0.0154 (9)	−0.0039 (9)	0.0005 (8)	−0.0024 (8)
N7	0.0164 (10)	0.0176 (10)	0.0203 (10)	−0.0022 (8)	0.0048 (8)	−0.0004 (8)
N8	0.0189 (10)	0.0152 (10)	0.0248 (11)	−0.0001 (8)	0.0086 (8)	0.0024 (8)
N9	0.0168 (10)	0.0164 (10)	0.0170 (10)	−0.0009 (8)	0.0042 (8)	−0.0004 (8)
N10	0.0157 (10)	0.0168 (10)	0.0161 (10)	−0.0013 (8)	0.0028 (8)	−0.0016 (8)
C1	0.0189 (12)	0.0310 (14)	0.0259 (13)	−0.0004 (11)	0.0076 (10)	0.0068 (11)
C2	0.0165 (12)	0.0275 (13)	0.0251 (13)	−0.0020 (10)	0.0072 (10)	0.0037 (11)
C3	0.0214 (12)	0.0165 (12)	0.0304 (14)	−0.0031 (10)	0.0063 (11)	0.0006 (10)
C4	0.0249 (13)	0.0161 (12)	0.0306 (14)	−0.0043 (10)	0.0056 (11)	−0.0036 (10)
C5	0.0197 (13)	0.0233 (13)	0.0330 (15)	0.0054 (10)	0.0052 (11)	0.0060 (11)
C6	0.0262 (13)	0.0173 (12)	0.0298 (14)	0.0034 (10)	0.0094 (11)	0.0047 (10)
C7	0.0256 (13)	0.0176 (12)	0.0281 (14)	0.0031 (10)	0.0136 (11)	−0.0006 (10)
C8	0.0257 (13)	0.0183 (12)	0.0199 (12)	−0.0014 (10)	0.0100 (10)	−0.0043 (10)
C9	0.0149 (12)	0.0223 (13)	0.0224 (13)	−0.0025 (9)	0.0036 (10)	0.0003 (10)
C10	0.0178 (12)	0.0204 (12)	0.0218 (12)	−0.0038 (9)	0.0030 (10)	0.0030 (10)
C11	0.0228 (13)	0.0200 (12)	0.0143 (11)	−0.0023 (10)	0.0033 (10)	0.0022 (9)
C12	0.0191 (12)	0.0228 (13)	0.0154 (12)	−0.0005 (9)	0.0023 (9)	−0.0007 (9)
C13	0.0146 (12)	0.0238 (13)	0.0206 (13)	−0.0028 (10)	0.0009 (10)	0.0014 (10)
C14	0.0188 (12)	0.0223 (13)	0.0218 (13)	−0.0041 (10)	0.0008 (10)	−0.0002 (10)
C15	0.0244 (13)	0.0170 (12)	0.0197 (12)	0.0002 (10)	0.0023 (10)	0.0010 (9)
C16	0.0229 (13)	0.0215 (13)	0.0214 (13)	0.0045 (10)	0.0001 (10)	0.0005 (10)
O1W	0.0222 (10)	0.0304 (11)	0.0284 (10)	−0.0013 (9)	0.0033 (8)	0.0019 (8)
O2W	0.0379 (13)	0.0591 (16)	0.0292 (12)	0.0028 (12)	0.0104 (10)	0.0008 (11)

Geometric parameters (Å, º) top

Pr1—O2	2.5568 (18)	N8—C6	1.490 (3)
Pr1—O8	2.5628 (18)	N8—C4	1.493 (3)
Pr1—O4	2.5687 (18)	N9—C8	1.489 (3)
Pr1—O7	2.5751 (17)	N9—C11	1.490 (3)
Pr1—O5	2.5910 (17)	N9—C9	1.492 (3)
Pr1—O11	2.6093 (18)	N10—C15	1.484 (3)
Pr1—O17	2.6287 (17)	N10—C12	1.485 (3)
Pr1—O1	2.6354 (18)	N10—C13	1.488 (3)
Pr1—O14	2.6445 (18)	C1—C2	1.511 (4)
Pr1—O10	2.6620 (18)	C1—H1A	0.9900
Pr1—O16	2.6730 (18)	C1—H1B	0.9900
Pr1—O13	2.7478 (17)	C2—H2A	0.9900
O1—N1	1.264 (3)	C2—H2B	0.9900
O2—N1	1.267 (3)	C3—C4	1.512 (4)
O3—N1	1.233 (3)	C3—H3A	0.9900
O4—N2	1.262 (3)	C3—H3B	0.9900
O5—N2	1.281 (3)	C4—H4A	0.9900
O6—N2	1.217 (3)	C4—H4B	0.9900
O7—N3	1.265 (3)	C5—C6	1.512 (4)
O8—N3	1.271 (3)	C5—H5A	0.9900
O9—N3	1.227 (3)	C5—H5B	0.9900
O10—N4	1.258 (3)	C6—H6A	0.9900
O11—N4	1.280 (3)	C6—H6B	0.9900
O12—N4	1.233 (3)	C7—C8	1.513 (3)
O13—N5	1.285 (3)	C7—H7A	0.9900
O14—N5	1.246 (3)	C7—H7B	0.9900
O15—N5	1.232 (3)	C8—H8A	0.9900
O16—N6	1.261 (3)	C8—H8B	0.9900
O17—N6	1.283 (3)	C9—C10	1.511 (3)
O18—N6	1.224 (3)	C9—H9A	0.9900
Pr2—O20	2.4548 (18)	C9—H9B	0.9900
Pr2—O22	2.4573 (18)	C10—H10A	0.9900
Pr2—O19	2.4698 (17)	C10—H10B	0.9900
Pr2—O21	2.4853 (17)	C11—C12	1.522 (3)
Pr2—O23	2.5596 (18)	C11—H11A	0.9900
Pr2—N7	2.677 (2)	C11—H11B	0.9900
Pr2—N9	2.682 (2)	C12—H12A	0.9900
Pr2—N10	2.7224 (19)	C12—H12B	0.9900
Pr2—N8	2.745 (2)	C13—C14	1.510 (3)
O19—C1	1.435 (3)	C13—H13A	0.9900
O19—H19	0.8400	C13—H13B	0.9900
O20—C5	1.435 (3)	C14—H14A	0.9900
O20—H20	0.8400	C14—H14B	0.9900
O21—C10	1.447 (3)	C15—C16	1.510 (3)
O21—H21	0.8400	C15—H15A	0.9900
O22—C16	1.447 (3)	C15—H15B	0.9900
O22—H22	0.8400	C16—H16A	0.9900
O23—H23A	0.8400	C16—H16B	0.9900
O23—H23B	0.8400	O1W—H1WA	0.8400
N7—C3	1.488 (3)	O1W—H1WB	0.8400
N7—C2	1.490 (3)	O2W—H2WA	0.8400
N7—C14	1.493 (3)	O2W—H2WB	0.8400
N8—C7	1.484 (3)

O2—Pr1—O8	120.72 (6)	N9—Pr2—N8	66.25 (6)
O2—Pr1—O4	67.39 (6)	N10—Pr2—N8	102.62 (6)
O8—Pr1—O4	170.29 (6)	C1—O19—Pr2	124.79 (14)
O2—Pr1—O7	131.93 (6)	C1—O19—H19	110
O8—Pr1—O7	49.83 (6)	Pr2—O19—H19	126
O4—Pr1—O7	121.21 (6)	C5—O20—Pr2	128.00 (15)
O2—Pr1—O5	110.71 (6)	C5—O20—H20	111
O8—Pr1—O5	120.86 (5)	Pr2—O20—H20	119
O4—Pr1—O5	49.43 (5)	C10—O21—Pr2	126.65 (13)
O7—Pr1—O5	74.87 (5)	C10—O21—H21	113
O2—Pr1—O11	102.45 (6)	Pr2—O21—H21	120
O8—Pr1—O11	64.38 (6)	C16—O22—Pr2	128.17 (14)
O4—Pr1—O11	120.93 (6)	C16—O22—H22	106
O7—Pr1—O11	108.29 (6)	Pr2—O22—H22	124
O5—Pr1—O11	130.76 (6)	Pr2—O23—H23A	129
O2—Pr1—O17	74.35 (6)	Pr2—O23—H23B	131
O8—Pr1—O17	105.07 (6)	H23A—O23—H23B	99
O4—Pr1—O17	70.97 (6)	C3—N7—C2	109.97 (19)
O7—Pr1—O17	66.86 (6)	C3—N7—C14	109.50 (19)
O5—Pr1—O17	61.97 (5)	C2—N7—C14	109.80 (19)
O11—Pr1—O17	165.97 (5)	C3—N7—Pr2	112.18 (14)
O2—Pr1—O1	49.33 (6)	C2—N7—Pr2	103.80 (14)
O8—Pr1—O1	74.84 (6)	C14—N7—Pr2	111.46 (14)
O4—Pr1—O1	114.47 (6)	C7—N8—C6	109.52 (19)
O7—Pr1—O1	113.30 (6)	C7—N8—C4	108.6 (2)
O5—Pr1—O1	159.38 (6)	C6—N8—C4	109.77 (19)
O11—Pr1—O1	66.42 (6)	C7—N8—Pr2	111.37 (14)
O17—Pr1—O1	102.69 (5)	C6—N8—Pr2	105.19 (14)
O2—Pr1—O14	163.57 (6)	C4—N8—Pr2	112.32 (14)
O8—Pr1—O14	71.18 (6)	C8—N9—C11	109.19 (18)
O4—Pr1—O14	102.11 (6)	C8—N9—C9	108.03 (19)
O7—Pr1—O14	64.04 (6)	C11—N9—C9	109.43 (18)
O5—Pr1—O14	66.47 (6)	C8—N9—Pr2	112.87 (14)
O11—Pr1—O14	71.41 (6)	C11—N9—Pr2	110.16 (14)
O17—Pr1—O14	115.25 (5)	C9—N9—Pr2	107.08 (14)
O1—Pr1—O14	134.08 (6)	C15—N10—C12	108.97 (19)
O2—Pr1—O10	65.40 (6)	C15—N10—C13	109.86 (19)
O8—Pr1—O10	109.86 (6)	C12—N10—C13	109.71 (19)
O4—Pr1—O10	77.92 (6)	C15—N10—Pr2	106.87 (13)
O7—Pr1—O10	156.60 (6)	C12—N10—Pr2	111.50 (14)
O5—Pr1—O10	116.91 (5)	C13—N10—Pr2	109.88 (14)
O11—Pr1—O10	48.41 (5)	O19—C1—C2	107.8 (2)
O17—Pr1—O10	136.14 (5)	O19—C1—H1A	110.1
O1—Pr1—O10	63.31 (6)	C2—C1—H1A	110.1
O14—Pr1—O10	100.75 (6)	O19—C1—H1B	110.1
O2—Pr1—O16	67.59 (6)	C2—C1—H1B	110.1
O8—Pr1—O16	70.21 (6)	H1A—C1—H1B	108.5
O4—Pr1—O16	110.90 (6)	N7—C2—C1	112.1 (2)
O7—Pr1—O16	65.60 (6)	N7—C2—H2A	109.2
O5—Pr1—O16	108.12 (5)	C1—C2—H2A	109.2
O11—Pr1—O16	117.89 (6)	N7—C2—H2B	109.2
O17—Pr1—O16	48.12 (5)	C1—C2—H2B	109.2
O1—Pr1—O16	62.40 (6)	H2A—C2—H2B	107.9
O14—Pr1—O16	128.84 (5)	N7—C3—C4	112.3 (2)
O10—Pr1—O16	123.22 (5)	N7—C3—H3A	109.1
O2—Pr1—O13	116.46 (6)	C4—C3—H3A	109.1
O8—Pr1—O13	109.66 (5)	N7—C3—H3B	109.1
O4—Pr1—O13	68.14 (6)	C4—C3—H3B	109.1
O7—Pr1—O13	109.44 (5)	H3A—C3—H3B	107.9
O5—Pr1—O13	66.50 (5)	N8—C4—C3	112.7 (2)
O11—Pr1—O13	66.46 (6)	N8—C4—H4A	109.0
O17—Pr1—O13	127.38 (5)	C3—C4—H4A	109.0
O1—Pr1—O13	123.63 (5)	N8—C4—H4B	109.0
O14—Pr1—O13	47.15 (5)	C3—C4—H4B	109.0
O10—Pr1—O13	62.75 (5)	H4A—C4—H4B	107.8
O16—Pr1—O13	173.92 (5)	O20—C5—C6	107.4 (2)
N1—O1—Pr1	94.55 (14)	O20—C5—H5A	110.2
N1—O2—Pr1	98.22 (14)	C6—C5—H5A	110.2
N2—O4—Pr1	97.99 (13)	O20—C5—H5B	110.2
N2—O5—Pr1	96.38 (13)	C6—C5—H5B	110.2
N3—O7—Pr1	96.30 (13)	H5A—C5—H5B	108.5
N3—O8—Pr1	96.72 (14)	N8—C6—C5	111.9 (2)
N4—O10—Pr1	95.97 (13)	N8—C6—H6A	109.2
N4—O11—Pr1	97.91 (13)	C5—C6—H6A	109.2
N5—O13—Pr1	94.82 (13)	N8—C6—H6B	109.2
N5—O14—Pr1	100.92 (14)	C5—C6—H6B	109.2
N6—O16—Pr1	96.40 (13)	H6A—C6—H6B	107.9
N6—O17—Pr1	97.92 (13)	N8—C7—C8	111.9 (2)
O3—N1—O1	121.6 (2)	N8—C7—H7A	109.2
O3—N1—O2	120.5 (2)	C8—C7—H7A	109.2
O1—N1—O2	117.9 (2)	N8—C7—H7B	109.2
O3—N1—Pr1	176.7 (2)	C8—C7—H7B	109.2
O1—N1—Pr1	60.73 (12)	H7A—C7—H7B	107.9
O2—N1—Pr1	57.17 (12)	N9—C8—C7	112.5 (2)
O6—N2—O4	122.8 (2)	N9—C8—H8A	109.1
O6—N2—O5	121.1 (2)	C7—C8—H8A	109.1
O4—N2—O5	116.1 (2)	N9—C8—H8B	109.1
O6—N2—Pr1	176.67 (19)	C7—C8—H8B	109.1
O4—N2—Pr1	57.52 (12)	H8A—C8—H8B	107.8
O5—N2—Pr1	58.65 (11)	N9—C9—C10	112.1 (2)
O9—N3—O7	121.4 (2)	N9—C9—H9A	109.2
O9—N3—O8	121.4 (2)	C10—C9—H9A	109.2
O7—N3—O8	117.2 (2)	N9—C9—H9B	109.2
O9—N3—Pr1	179.63 (19)	C10—C9—H9B	109.2
O7—N3—Pr1	58.84 (11)	H9A—C9—H9B	107.9
O8—N3—Pr1	58.31 (11)	O21—C10—C9	107.51 (19)
O12—N4—O10	122.5 (2)	O21—C10—H10A	110.2
O12—N4—O11	120.7 (2)	C9—C10—H10A	110.2
O10—N4—O11	116.8 (2)	O21—C10—H10B	110.2
O15—N5—O14	122.1 (2)	C9—C10—H10B	110.2
O15—N5—O13	120.8 (2)	H10A—C10—H10B	108.5
O14—N5—O13	117.0 (2)	N9—C11—C12	111.83 (19)
O18—N6—O16	122.7 (2)	N9—C11—H11A	109.2
O18—N6—O17	120.9 (2)	C12—C11—H11A	109.2
O16—N6—O17	116.43 (19)	N9—C11—H11B	109.2
O20—Pr2—O22	137.74 (6)	C12—C11—H11B	109.2
O20—Pr2—O19	81.71 (6)	H11A—C11—H11B	107.9
O22—Pr2—O19	86.19 (6)	N10—C12—C11	112.48 (19)
O20—Pr2—O21	79.83 (6)	N10—C12—H12A	109.1
O22—Pr2—O21	83.60 (6)	C11—C12—H12A	109.1
O19—Pr2—O21	139.20 (6)	N10—C12—H12B	109.1
O20—Pr2—O23	69.37 (7)	C11—C12—H12B	109.1
O22—Pr2—O23	68.40 (6)	H12A—C12—H12B	107.8
O19—Pr2—O23	70.94 (6)	N10—C13—C14	112.1 (2)
O21—Pr2—O23	68.55 (6)	N10—C13—H13A	109.2
O20—Pr2—N7	118.58 (6)	C14—C13—H13A	109.2
O22—Pr2—N7	90.29 (6)	N10—C13—H13B	109.2
O19—Pr2—N7	62.64 (6)	C14—C13—H13B	109.2
O21—Pr2—N7	156.27 (6)	H13A—C13—H13B	107.9
O23—Pr2—N7	129.98 (6)	N7—C14—C13	113.0 (2)
O20—Pr2—N9	87.24 (6)	N7—C14—H14A	109.0
O22—Pr2—N9	118.26 (6)	C13—C14—H14A	109.0
O19—Pr2—N9	152.20 (6)	N7—C14—H14B	109.0
O21—Pr2—N9	62.09 (6)	C13—C14—H14B	109.0
O23—Pr2—N9	128.27 (6)	H14A—C14—H14B	107.8
N7—Pr2—N9	101.75 (6)	N10—C15—C16	112.6 (2)
O20—Pr2—N10	154.29 (6)	N10—C15—H15A	109.1
O22—Pr2—N10	62.69 (6)	C16—C15—H15A	109.1
O19—Pr2—N10	120.03 (6)	N10—C15—H15B	109.1
O21—Pr2—N10	89.52 (6)	C16—C15—H15B	109.1
O23—Pr2—N10	128.15 (6)	H15A—C15—H15B	107.8
N7—Pr2—N10	67.43 (6)	O22—C16—C15	107.2 (2)
N9—Pr2—N10	67.14 (6)	O22—C16—H16A	110.3
O20—Pr2—N8	62.76 (6)	C15—C16—H16A	110.3
O22—Pr2—N8	156.28 (6)	O22—C16—H16B	110.3
O19—Pr2—N8	86.05 (6)	C15—C16—H16B	110.3
O21—Pr2—N8	116.28 (6)	H16A—C16—H16B	108.5
O23—Pr2—N8	129.22 (6)	H1WA—O1W—H1WB	105
N7—Pr2—N8	66.27 (6)	H2WA—O2W—H2WB	114

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O23—H23A···O13ⁱ	0.84 (2)	2.24 (2)	2.979 (3)	146 (2)
O20—H20···O1W	0.84 (2)	1.79 (2)	2.622 (3)	174 (2)
O23—H23B···O17	0.84 (2)	2.02 (2)	2.835 (3)	164 (2)
O1W—H1WA···O15ⁱ	0.84 (2)	2.05 (2)	2.873 (3)	165 (2)
O1W—H1WB···O11ⁱⁱ	0.84 (2)	2.02 (2)	2.849 (3)	171 (2)
O22—H22···O2W	0.84 (2)	1.78 (3)	2.599 (3)	166 (2)
O21—H21···O13ⁱ	0.84 (2)	1.93 (2)	2.768 (2)	174 (2)
O19—H19···O5	0.84 (2)	1.87 (2)	2.702 (2)	169 (2)
O2W—H2WA···O3ⁱⁱⁱ	0.84 (2)	2.24 (2)	3.079 (4)	175 (2)
O2W—H2WB···O9	0.84 (2)	2.43 (2)	3.032 (3)	130 (2)
O2W—H2WB···O7	0.84 (2)	2.46 (2)	3.078 (3)	131 (2)
O2W—H2WB···O6ⁱ	0.84 (2)	2.50 (2)	3.191 (3)	141 (2)

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

Experimental details

Crystal data
Chemical formula	[Pr(C₁₆H₃₆N₄O₄)(H₂O)][Pr(NO₃)₆]·2H₂O
M_r	1056.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	15.5786 (3), 14.4453 (3), 15.5995 (3)
β (°)	99.749 (1)
V (Å³)	3459.78 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.89
Crystal size (mm)	0.25 × 0.25 × 0.15

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.516, 0.651
No. of measured, independent and observed [I > 2σ(I)] reflections	27454, 7950, 7143
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.055, 1.09
No. of reflections	7950
No. of parameters	519
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.29, −0.73

Computer programs: COLLECT (Nonius, 1997-2002), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 2001), SHELXTL.

Selected bond lengths (Å) top

Pr1—O2	2.5568 (18)	Pr1—O13	2.7478 (17)
Pr1—O8	2.5628 (18)	Pr2—O20	2.4548 (18)
Pr1—O4	2.5687 (18)	Pr2—O22	2.4573 (18)
Pr1—O7	2.5751 (17)	Pr2—O19	2.4698 (17)
Pr1—O5	2.5910 (17)	Pr2—O21	2.4853 (17)
Pr1—O11	2.6093 (18)	Pr2—O23	2.5596 (18)
Pr1—O17	2.6287 (17)	Pr2—N7	2.677 (2)
Pr1—O1	2.6354 (18)	Pr2—N9	2.682 (2)
Pr1—O14	2.6445 (18)	Pr2—N10	2.7224 (19)
Pr1—O10	2.6620 (18)	Pr2—N8	2.745 (2)
Pr1—O16	2.6730 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O23—H23A···O13ⁱ	0.84 (2)	2.24 (2)	2.979 (3)	146 (2)
O20—H20···O1W	0.84 (2)	1.79 (2)	2.622 (3)	174 (2)
O23—H23B···O17	0.84 (2)	2.02 (2)	2.835 (3)	164 (2)
O1W—H1WA···O15ⁱ	0.84 (2)	2.05 (2)	2.873 (3)	165 (2)
O1W—H1WB···O11ⁱⁱ	0.84 (2)	2.02 (2)	2.849 (3)	171 (2)
O22—H22···O2W	0.84 (2)	1.78 (3)	2.599 (3)	166 (2)
O21—H21···O13ⁱ	0.84 (2)	1.93 (2)	2.768 (2)	174 (2)
O19—H19···O5	0.84 (2)	1.87 (2)	2.702 (2)	169 (2)
O2W—H2WA···O3ⁱⁱⁱ	0.84 (2)	2.24 (2)	3.079 (4)	175 (2)
O2W—H2WB···O9	0.84 (2)	2.43 (2)	3.032 (3)	130 (2)
O2W—H2WB···O7	0.84 (2)	2.46 (2)	3.078 (3)	131 (2)
O2W—H2WB···O6ⁱ	0.84 (2)	2.50 (2)	3.191 (3)	141 (2)

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

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