Metal-organic frameworks based on uranyl and phosphonate ligands

Three new crystalline metal-organic frameworks have been prepared from the reaction of uranyl nitrate with nitrilotris(methylphosphonic acid) [H₆nmp, N(CH₂PO₃H₂)₃], 1,4-phenylenebis(methylene)diphosphonic acid [H₄pmd, C₆H₄(PO₃H₂)₂], and (benzene-1,3,5-triyltris(methylene))triphosphonic acid [H₆bmt, C₆H₃(PO₃H₂)₃]. Compound [(UO₂)₂F(H₃nmp)(H₂O)]·4H₂O (I) crystallizes in space group C2/c, showing two crystallographically independent uranyl centres with pentagonal bipyramidal coordination geometries. While one metal centre is composed of a {(UO₂)O₃(μ-F)}₂ dimer, the other comprises an isolated {(UO₂)O₅} polyhedron. Compound [(UO₂)(H₂pmd)] (II) crystallizes in space group P2₁/c, showing a centrosymmetric uranyl centre with an octahedral {(UO₂)O₄} coordination geometry. Compound [(UO₂)₃(H₃bmt)₂(H₂O)₂]·14H₂O (III) crystallizes in space group , showing two crystallographically independent uranyl centres. One uranyl centre is a {(UO₂)O₅} pentagonal bipyramid similar to that in (I), while the other is a {(UO₂)O₄} centrosymmetric octahedron similar to that in (II). Compounds (I) and (III) contain solvent-accessible volumes accounting for ca 23.6 and 26.9% of their unit-cell volume, respectively. In (I) the cavity has a columnar shape and is occupied by disordered water molecules, while in (III) the cavity is a two-dimensional layer with more ordered water molecules. All compounds have been studied in the solid state using FT-IR spectroscopy. Topological studies show that compounds (I) and (III) are trinodal, with 3,6,6- and 4,4,6-connected networks, respectively. Compound (II) is instead a 4-connected uninodal network of the type cds.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL (Bruker, 2008).

Figures

(I)

Crystal data

C3H11FNO14P3U2·4(H2O)	F(000) = 3408
Mr = 945.16	Dx = 3.170 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 76640 reflections
a = 25.8297 (10) Å	θ = 3.6–29.1°
b = 8.7560 (3) Å	µ = 16.71 mm^−1
c = 17.7432 (7) Å	T = 150 K
β = 99.951 (2)°	Plate, yellow
V = 3952.5 (3) Å^3	0.05 × 0.03 × 0.01 mm
Z = 8

Data collection

Bruker X8 Kappa CCD APEX-II diffractometer	5310 independent reflections
Radiation source: fine-focus sealed tube	4724 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ω and φ scans	θmax = 29.1°, θmin = 3.6°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −35→35
Tmin = 0.489, Tmax = 0.921	k = −11→11
76767 measured reflections	l = −24→24

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0206P)^2 + 49.9087P] where P = (Fo^2 + 2Fc^2)/3
5310 reflections	(Δ/σ)max = 0.002
255 parameters	Δρmax = 1.52 e Å^−3
5 restraints	Δρmin = −1.04 e Å^−3

Special details

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. Water molecules of crystallization were refined isotropically with a common displacement factor. The assignment of electron densities around the oxygen atoms of the solvent waters did not allow the convergence to a stable and credible solution. H-atoms near N1, O3 and O8 were located and placed with N—H and O—H distances constrained to 0.84 (1) A, and P—H distances to be higher than 2.0 (1) A. The two sites of protonation of O8 were assigned to a half occupation value each. The second paramenter of the recommended weighting scheme oscillated between values around 5 and values around 50 with no foreseeable convergence. The value around 50 was used arbitrarily.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
U1	0.433256 (7)	0.59178 (2)	0.358471 (10)	0.01488 (5)
U2	0.254508 (7)	0.349092 (19)	0.400318 (9)	0.00984 (5)
C1	0.37456 (19)	0.5151 (6)	0.1095 (3)	0.0139 (9)
H1A	0.3658	0.6144	0.1308	0.017*
H1B	0.3783	0.5334	0.0556	0.017*
C2	0.3155 (2)	0.3731 (6)	0.1867 (3)	0.0148 (10)
H2A	0.3462	0.3210	0.2171	0.018*
H2B	0.2857	0.3001	0.1801	0.018*
C3	0.33065 (19)	0.2642 (5)	0.0650 (3)	0.0128 (9)
H3A	0.3014	0.1972	0.0737	0.015*
H3B	0.3639	0.2112	0.0857	0.015*
F1	0.23279 (12)	0.1321 (3)	0.46641 (15)	0.0163 (6)
N1	0.32812 (16)	0.4101 (5)	0.1090 (2)	0.0106 (7)
H1Z	0.3002 (16)	0.466 (6)	0.080 (3)	0.016*
O1	0.43693 (15)	0.4568 (5)	0.2463 (2)	0.0210 (8)
O2	0.47483 (15)	0.5797 (5)	0.1385 (2)	0.0246 (9)
O3	0.45060 (16)	0.3005 (5)	0.1315 (2)	0.0253 (9)
H3Z	0.437 (3)	0.2283 (12)	0.164 (3)	0.038*
O4	0.34733 (15)	0.5936 (5)	0.2926 (2)	0.0210 (8)
O5	0.25783 (14)	0.4716 (4)	0.28612 (19)	0.0152 (7)
O6	0.27386 (15)	0.6555 (4)	0.18543 (19)	0.0161 (7)
O7	0.28498 (14)	0.4047 (4)	−0.0612 (2)	0.0156 (7)
O8	0.30686 (17)	0.1300 (4)	−0.0688 (2)	0.0206 (8)
H8X	0.336 (3)	0.062 (12)	−0.062 (8)	0.031*	0.50
H8Y	0.316 (5)	0.088 (15)	−0.114 (5)	0.031*	0.50
O9	0.38037 (15)	0.3232 (5)	−0.0544 (2)	0.0234 (9)
O10	0.43696 (15)	0.7738 (5)	0.3171 (2)	0.0241 (8)
O11	0.43183 (16)	0.4109 (5)	0.4025 (2)	0.0236 (8)
O12	0.32043 (14)	0.2868 (5)	0.4084 (2)	0.0202 (8)
O13	0.18893 (14)	0.4123 (4)	0.3939 (2)	0.0172 (7)
O1W	0.48309 (16)	0.6959 (6)	0.4817 (2)	0.0297 (10)
P1	0.43900 (5)	0.45588 (16)	0.16175 (7)	0.0149 (2)
P2	0.29844 (5)	0.53666 (14)	0.24144 (7)	0.0104 (2)
P3	0.32701 (5)	0.28900 (14)	−0.03694 (7)	0.0110 (2)
O2W	0.4438 (3)	0.8888 (7)	0.1220 (4)	0.0325 (7)*	0.70
O3W	0.5271 (3)	0.0930 (7)	0.1467 (4)	0.0325 (7)*	0.70
O4W	0.3383 (4)	0.0683 (11)	−0.2091 (6)	0.0325 (7)*	0.50
O5W	0.3402 (5)	0.0180 (14)	−0.1848 (7)	0.0325 (7)*	0.40
O6W	0.4024 (5)	0.0557 (14)	0.2286 (7)	0.0325 (7)*	0.40
O7W	0.4228 (5)	0.0839 (14)	0.2203 (7)	0.0325 (7)*	0.40
O8W	0.3955 (4)	−0.0687 (11)	−0.0405 (6)	0.0325 (7)*	0.50
O9W	0.4128 (7)	−0.1051 (19)	−0.0197 (9)	0.0325 (7)*	0.30
O10W	0.5000	0.126 (4)	0.2500	0.0325 (7)*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
U1	0.01005 (9)	0.02227 (10)	0.01238 (9)	0.00138 (7)	0.00209 (6)	−0.00142 (7)
U2	0.01298 (9)	0.01007 (8)	0.00684 (8)	−0.00170 (6)	0.00276 (6)	−0.00023 (6)
C1	0.011 (2)	0.014 (2)	0.016 (2)	−0.0033 (18)	0.0019 (18)	0.0031 (18)
C2	0.017 (2)	0.016 (2)	0.012 (2)	0.0006 (19)	0.0046 (18)	0.0053 (18)
C3	0.011 (2)	0.012 (2)	0.015 (2)	0.0007 (17)	0.0028 (18)	0.0027 (17)
F1	0.0282 (17)	0.0133 (14)	0.0067 (13)	−0.0068 (12)	0.0012 (11)	−0.0007 (10)
N1	0.0123 (19)	0.0116 (18)	0.0081 (17)	0.0001 (15)	0.0022 (15)	0.0036 (14)
O1	0.0146 (18)	0.034 (2)	0.0142 (18)	0.0028 (16)	0.0028 (14)	−0.0039 (16)
O2	0.0119 (18)	0.033 (2)	0.030 (2)	−0.0044 (16)	0.0051 (16)	0.0103 (18)
O3	0.021 (2)	0.025 (2)	0.029 (2)	0.0051 (17)	0.0015 (17)	−0.0033 (17)
O4	0.0142 (18)	0.032 (2)	0.0163 (18)	−0.0038 (16)	0.0022 (14)	−0.0076 (16)
O5	0.0180 (18)	0.0181 (17)	0.0110 (16)	−0.0037 (14)	0.0070 (13)	0.0043 (13)
O6	0.026 (2)	0.0128 (16)	0.0095 (16)	0.0039 (15)	0.0044 (14)	0.0047 (13)
O7	0.0186 (18)	0.0155 (17)	0.0127 (16)	0.0064 (14)	0.0021 (14)	0.0023 (13)
O8	0.032 (2)	0.0126 (18)	0.0178 (18)	−0.0020 (15)	0.0069 (16)	−0.0049 (14)
O9	0.0137 (18)	0.039 (2)	0.0179 (19)	−0.0030 (16)	0.0051 (15)	0.0084 (17)
O10	0.0176 (19)	0.026 (2)	0.029 (2)	−0.0029 (16)	0.0055 (16)	0.0024 (17)
O11	0.020 (2)	0.026 (2)	0.024 (2)	0.0030 (16)	0.0043 (16)	−0.0004 (16)
O12	0.0125 (18)	0.024 (2)	0.024 (2)	−0.0019 (15)	0.0036 (15)	−0.0004 (16)
O13	0.0149 (18)	0.0202 (18)	0.0169 (18)	−0.0033 (14)	0.0039 (14)	0.0006 (14)
O1W	0.0132 (19)	0.049 (3)	0.025 (2)	0.0003 (18)	−0.0028 (16)	−0.0107 (19)
P1	0.0108 (6)	0.0194 (6)	0.0144 (6)	0.0004 (5)	0.0021 (5)	−0.0012 (5)
P2	0.0116 (6)	0.0130 (5)	0.0066 (5)	0.0000 (5)	0.0016 (4)	0.0028 (4)
P3	0.0122 (6)	0.0105 (5)	0.0103 (5)	0.0005 (4)	0.0018 (4)	0.0008 (4)

Geometric parameters (Å, º)

U1—O10	1.764 (4)	C2—P2	1.826 (5)
U1—O11	1.769 (4)	C2—H2A	0.9900
U1—O4	2.323 (4)	C2—H2B	0.9900
U1—O1	2.331 (4)	C3—N1	1.505 (6)
U1—O9^i	2.354 (4)	C3—P3	1.808 (5)
U1—O2^ii	2.368 (4)	C3—H3A	0.9900
U1—O1W	2.510 (4)	C3—H3B	0.9900
U2—O13	1.767 (4)	N1—H1Z	0.945 (10)
U2—O12	1.770 (4)	O1—P1	1.510 (4)
U2—O5	2.307 (3)	O2—P1	1.527 (4)
U2—O6^iii	2.311 (3)	O3—P1	1.511 (4)
U2—F1^iv	2.336 (3)	O3—H3Z	0.956 (10)
U2—F1	2.351 (3)	O4—P2	1.507 (4)
U2—O7^i	2.355 (4)	O5—P2	1.530 (3)
U2—U2^iv	3.9829 (3)	O6—P2	1.502 (4)
C1—N1	1.510 (6)	O7—P3	1.493 (4)
C1—P1	1.835 (5)	O8—P3	1.558 (4)
C1—H1A	0.9900	O8—H8X	0.949 (10)
C1—H1B	0.9900	O8—H8Y	0.949 (10)
C2—N1	1.507 (6)	O9—P3	1.494 (4)
O10—U1—O11	177.74 (19)	N1—C1—H1B	107.6
O10—U1—O4	84.27 (17)	P1—C1—H1B	107.6
O11—U1—O4	97.91 (17)	H1A—C1—H1B	107.1
O10—U1—O1	95.15 (17)	N1—C2—P2	115.3 (3)
O11—U1—O1	86.01 (16)	N1—C2—H2A	108.4
O4—U1—O1	75.54 (13)	P2—C2—H2A	108.4
O10—U1—O9^i	93.82 (17)	N1—C2—H2B	108.4
O11—U1—O9^i	86.23 (17)	P2—C2—H2B	108.4
O4—U1—O9^i	73.50 (13)	H2A—C2—H2B	107.5
O1—U1—O9^i	146.64 (13)	N1—C3—P3	114.7 (3)
O10—U1—O2^ii	85.63 (17)	N1—C3—H3A	108.6
O11—U1—O2^ii	92.70 (17)	P3—C3—H3A	108.6
O4—U1—O2^ii	151.51 (14)	N1—C3—H3B	108.6
O1—U1—O2^ii	78.94 (13)	P3—C3—H3B	108.6
O9^i—U1—O2^ii	133.83 (13)	H3A—C3—H3B	107.6
O10—U1—O1W	88.73 (18)	U2^iv—F1—U2	116.37 (11)
O11—U1—O1W	89.24 (17)	C3—N1—C2	109.1 (4)
O4—U1—O1W	137.52 (13)	C3—N1—C1	114.5 (4)
O1—U1—O1W	146.92 (13)	C2—N1—C1	115.1 (4)
O9^i—U1—O1W	65.24 (13)	C3—N1—H1Z	105 (4)
O2^ii—U1—O1W	68.60 (13)	C2—N1—H1Z	110 (4)
O13—U2—O12	179.02 (17)	C1—N1—H1Z	103 (4)
O13—U2—O5	88.77 (15)	P1—O1—U1	149.9 (3)
O12—U2—O5	91.88 (15)	P1—O2—U1^ii	132.6 (2)
O13—U2—O6^iii	89.78 (15)	P1—O3—H3Z	105.6 (10)
O12—U2—O6^iii	91.04 (16)	P2—O4—U1	158.3 (3)
O5—U2—O6^iii	79.54 (12)	P2—O5—U2	139.6 (2)
O13—U2—F1^iv	90.48 (14)	P2—O6—U2^v	173.5 (2)
O12—U2—F1^iv	88.57 (15)	P3—O7—U2^vi	153.5 (2)
O5—U2—F1^iv	146.73 (11)	P3—O8—H8X	108 (9)
O6^iii—U2—F1^iv	133.72 (11)	P3—O8—H8Y	122 (8)
O13—U2—F1	88.66 (14)	H8X—O8—H8Y	64 (10)
O12—U2—F1	91.14 (15)	P3—O9—U1^vi	149.3 (2)
O5—U2—F1	149.54 (11)	O1—P1—O3	113.6 (2)
O6^iii—U2—F1	70.11 (11)	O1—P1—O2	113.1 (2)
F1^iv—U2—F1	63.63 (11)	O3—P1—O2	112.1 (2)
O13—U2—O7^i	90.02 (15)	O1—P1—C1	108.4 (2)
O12—U2—O7^i	89.43 (16)	O3—P1—C1	107.0 (2)
O5—U2—O7^i	76.57 (12)	O2—P1—C1	101.7 (2)
O6^iii—U2—O7^i	156.11 (12)	O6—P2—O4	112.6 (2)
F1^iv—U2—O7^i	70.17 (11)	O6—P2—O5	110.6 (2)
F1—U2—O7^i	133.77 (11)	O4—P2—O5	112.9 (2)
O13—U2—U2^iv	89.49 (12)	O6—P2—C2	107.7 (2)
O12—U2—U2^iv	89.83 (12)	O4—P2—C2	109.0 (2)
O5—U2—U2^iv	177.80 (9)	O5—P2—C2	103.5 (2)
O6^iii—U2—U2^iv	101.80 (9)	O7—P3—O9	117.1 (2)
F1^iv—U2—U2^iv	31.93 (7)	O7—P3—O8	108.7 (2)
F1—U2—U2^iv	31.71 (7)	O9—P3—O8	111.5 (2)
O7^i—U2—U2^iv	102.08 (8)	O7—P3—C3	106.2 (2)
N1—C1—P1	118.8 (3)	O9—P3—C3	109.9 (2)
N1—C1—H1A	107.6	O8—P3—C3	102.2 (2)
P1—C1—H1A	107.6
O13—U2—F1—U2^iv	−91.20 (17)	O7^i—U2—O5—P2	67.8 (3)
O12—U2—F1—U2^iv	87.84 (18)	U1—O1—P1—O3	169.7 (4)
O5—U2—F1—U2^iv	−176.50 (18)	U1—O1—P1—O2	40.5 (5)
O6^iii—U2—F1—U2^iv	178.54 (18)	U1—O1—P1—C1	−71.4 (5)
F1^iv—U2—F1—U2^iv	−0.001 (2)	U1^ii—O2—P1—O1	83.1 (4)
O7^i—U2—F1—U2^iv	−2.5 (2)	U1^ii—O2—P1—O3	−46.9 (4)
P3—C3—N1—C2	163.4 (3)	U1^ii—O2—P1—C1	−160.9 (3)
P3—C3—N1—C1	−66.0 (5)	N1—C1—P1—O1	−68.3 (4)
P2—C2—N1—C3	−168.8 (3)	N1—C1—P1—O3	54.6 (4)
P2—C2—N1—C1	61.0 (5)	N1—C1—P1—O2	172.4 (4)
P1—C1—N1—C3	−68.4 (5)	U1—O4—P2—O6	−134.5 (6)
P1—C1—N1—C2	59.2 (5)	U1—O4—P2—O5	99.4 (6)
O10—U1—O1—P1	−3.3 (5)	U1—O4—P2—C2	−15.0 (7)
O11—U1—O1—P1	178.7 (5)	U2—O5—P2—O6	−157.2 (3)
O4—U1—O1—P1	79.5 (5)	U2—O5—P2—O4	−30.1 (4)
O9^i—U1—O1—P1	101.7 (5)	U2—O5—P2—C2	87.6 (4)
O2^ii—U1—O1—P1	−87.8 (5)	N1—C2—P2—O6	29.2 (4)
O1W—U1—O1—P1	−98.9 (5)	N1—C2—P2—O4	−93.3 (4)
O10—U1—O4—P2	131.0 (7)	N1—C2—P2—O5	146.3 (3)
O11—U1—O4—P2	−49.6 (7)	U2^vi—O7—P3—O9	−18.8 (6)
O1—U1—O4—P2	34.1 (6)	U2^vi—O7—P3—O8	−146.2 (4)
O9^i—U1—O4—P2	−133.3 (7)	U2^vi—O7—P3—C3	104.4 (5)
O2^ii—U1—O4—P2	61.2 (8)	U1^vi—O9—P3—O7	−45.2 (6)
O1W—U1—O4—P2	−147.2 (6)	U1^vi—O9—P3—O8	80.9 (5)
O13—U2—O5—P2	158.1 (3)	U1^vi—O9—P3—C3	−166.5 (5)
O12—U2—O5—P2	−21.2 (4)	N1—C3—P3—O7	−43.0 (4)
O6^iii—U2—O5—P2	−111.9 (3)	N1—C3—P3—O9	84.6 (4)
F1^iv—U2—O5—P2	69.1 (4)	N1—C3—P3—O8	−156.9 (3)
F1—U2—O5—P2	−116.7 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1Z···F1^v	0.95 (1)	1.81 (3)	2.705 (5)	157 (5)
O3—H3Z···O6W	0.96 (1)	2.19 (2)	3.139 (13)	175 (6)
O3—H3Z···O7W	0.96 (1)	1.70 (2)	2.643 (13)	171 (5)
O8—H8Y···O4W	0.95 (1)	1.88 (4)	2.802 (10)	163 (13)
O8—H8Y···O5W	0.95 (1)	1.62 (3)	2.560 (13)	171 (14)
O8—H8X···O8W	0.95 (1)	1.90 (2)	2.850 (11)	176 (13)
O8—H8X···O9W	0.95 (1)	2.48 (3)	3.415 (17)	170 (12)

Symmetry code: (v) −x+1/2, y+1/2, −z+1/2.

(II)

Crystal data

C8H10O8P2U	F(000) = 488
Mr = 534.13	Dx = 2.714 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8989 reflections
a = 10.9522 (13) Å	θ = 3.7–33.1°
b = 6.4691 (7) Å	µ = 12.69 mm^−1
c = 9.2802 (10) Å	T = 296 K
β = 96.333 (9)°	Plate, yellow
V = 653.50 (13) Å^3	0.03 × 0.02 × 0.01 mm
Z = 2

Data collection

Bruker X8 Kappa CCD APEX-II diffractometer	2475 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω and φ scans	θmax = 33.1°, θmin = 3.7°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −16→16
Tmin = 0.702, Tmax = 0.939	k = −9→9
8989 measured reflections	l = −13→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0205P)^2] where P = (Fo^2 + 2Fc^2)/3
2475 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 1.91 e Å^−3
1 restraint	Δρmin = −2.74 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
U1	0.5000	0.0000	1.0000	0.01518 (7)
P1	0.70512 (12)	0.3134 (2)	0.81343 (14)	0.0175 (3)
O3	0.6449 (3)	0.4402 (5)	0.6896 (4)	0.0260 (9)
O4	0.5598 (4)	−0.2530 (5)	0.9798 (4)	0.0273 (9)
O1	0.6318 (3)	0.1263 (6)	0.8481 (4)	0.0264 (8)
O2	0.7302 (4)	0.4518 (5)	0.9517 (4)	0.0270 (9)
H2Z	0.671 (3)	0.529 (7)	0.962 (7)	0.041*
C1	0.8534 (5)	0.2358 (8)	0.7741 (5)	0.0227 (11)
H1A	0.8440	0.1529	0.6864	0.027*
H1B	0.8994	0.3586	0.7537	0.027*
C2	0.9290 (5)	0.1135 (8)	0.8917 (5)	0.0172 (11)
C3	0.8957 (5)	−0.0858 (9)	0.9271 (6)	0.0232 (12)
H3	0.8253	−0.1450	0.8788	0.028*
C4	1.0343 (5)	0.1976 (8)	0.9667 (6)	0.0228 (11)
H4	1.0580	0.3311	0.9451	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
U1	0.01212 (10)	0.01505 (11)	0.01776 (11)	−0.00108 (18)	−0.00114 (7)	−0.00388 (16)
P1	0.0131 (6)	0.0221 (6)	0.0164 (6)	0.0029 (5)	−0.0015 (5)	0.0021 (5)
O3	0.0175 (19)	0.034 (2)	0.0248 (19)	0.0051 (15)	−0.0033 (15)	0.0050 (15)
O4	0.028 (2)	0.0198 (19)	0.034 (2)	0.0064 (17)	0.0030 (17)	−0.0047 (16)
O1	0.020 (2)	0.028 (2)	0.032 (2)	−0.0052 (17)	0.0050 (16)	0.0005 (17)
O2	0.027 (2)	0.025 (2)	0.026 (2)	0.0110 (16)	−0.0074 (16)	−0.0061 (15)
C1	0.020 (3)	0.029 (3)	0.018 (3)	0.006 (2)	−0.002 (2)	0.007 (2)
C2	0.012 (3)	0.024 (3)	0.016 (3)	0.005 (2)	0.0025 (19)	0.002 (2)
C3	0.016 (3)	0.027 (3)	0.026 (3)	0.000 (2)	−0.002 (2)	0.001 (2)
C4	0.021 (3)	0.019 (2)	0.028 (3)	0.000 (2)	0.003 (2)	0.001 (2)

Geometric parameters (Å, º)

U1—O4	1.781 (3)	O2—H2Z	0.834 (10)
U1—O4^i	1.781 (3)	C1—C2	1.518 (7)
U1—O3^ii	2.269 (4)	C1—H1A	0.9700
U1—O3^iii	2.269 (4)	C1—H1B	0.9700
U1—O1	2.278 (3)	C2—C3	1.389 (7)
U1—O1^i	2.278 (3)	C2—C4	1.390 (7)
P1—O3	1.504 (4)	C3—C4^v	1.384 (7)
P1—O1	1.507 (4)	C3—H3	0.9300
P1—O2	1.564 (4)	C4—C3^v	1.384 (7)
P1—C1	1.776 (5)	C4—H4	0.9300
O3—U1^iv	2.269 (4)
O4—U1—O4^i	179.999 (2)	P1—O1—U1	144.0 (2)
O4—U1—O3^ii	90.25 (15)	P1—O2—H2Z	111 (4)
O4—U1—O3^iii	89.75 (15)	C2—C1—P1	115.9 (3)
O3^ii—U1—O3^iii	180.0	C2—C1—H1A	108.3
O4—U1—O1	89.93 (15)	P1—C1—H1A	108.3
O3^ii—U1—O1	88.95 (14)	C2—C1—H1B	108.3
O3^iii—U1—O1	91.05 (14)	P1—C1—H1B	108.3
O4—U1—O1^i	90.07 (15)	H1A—C1—H1B	107.4
O3^ii—U1—O1^i	91.05 (14)	C3—C2—C4	118.0 (5)
O3^iii—U1—O1^i	88.95 (14)	C3—C2—C1	121.2 (5)
O1—U1—O1^i	179.9990 (10)	C4—C2—C1	120.8 (5)
O3—P1—O1	113.7 (2)	C4^v—C3—C2	120.9 (6)
O3—P1—O2	109.7 (2)	C4^v—C3—H3	119.5
O1—P1—O2	109.5 (2)	C2—C3—H3	119.5
O3—P1—C1	109.3 (2)	C3^v—C4—C2	121.1 (5)
O1—P1—C1	109.7 (2)	C3^v—C4—H4	119.5
O2—P1—C1	104.4 (2)	C2—C4—H4	119.5
P1—O3—U1^iv	153.6 (2)
O1—P1—O3—U1^iv	−9.1 (6)	O3—P1—C1—C2	177.5 (4)
O2—P1—O3—U1^iv	−132.2 (5)	O1—P1—C1—C2	−57.2 (5)
C1—P1—O3—U1^iv	113.9 (5)	O2—P1—C1—C2	60.2 (4)
O3—P1—O1—U1	−99.5 (4)	P1—C1—C2—C3	68.5 (6)
O2—P1—O1—U1	23.7 (5)	P1—C1—C2—C4	−112.0 (5)
C1—P1—O1—U1	137.7 (4)	C4—C2—C3—C4^v	−0.4 (8)
O4—U1—O1—P1	−149.5 (4)	C1—C2—C3—C4^v	179.2 (5)
O4^i—U1—O1—P1	30.5 (4)	C3—C2—C4—C3^v	0.4 (8)
O3^ii—U1—O1—P1	−59.3 (4)	C1—C2—C4—C3^v	−179.2 (5)
O3^iii—U1—O1—P1	120.7 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2Z···O4^vi	0.83 (1)	1.88 (2)	2.703 (5)	168 (5)

Symmetry code: (vi) x, y+1, z.

(III)

Crystal data

C9H14O13P3U1.50·7(H2O)	Z = 2
Mr = 906.27	F(000) = 850
Triclinic, P1	Dx = 2.416 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7982 (3) Å	Cell parameters from 54948 reflections
b = 11.8876 (4) Å	θ = 2.3–25.4°
c = 12.6446 (4) Å	µ = 10.03 mm^−1
α = 95.219 (2)°	T = 150 K
β = 106.752 (2)°	Block, yellow
γ = 96.980 (2)°	0.02 × 0.02 × 0.01 mm
V = 1245.89 (7) Å^3

Data collection

Bruker X8 Kappa CCD APEX-II diffractometer	4560 independent reflections
Radiation source: fine-focus sealed tube	4004 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ω and φ scans	θmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −10→10
Tmin = 0.825, Tmax = 0.906	k = −14→14
54948 measured reflections	l = −15→15

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.041	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0095P)^2 + 3.2581P] where P = (Fo^2 + 2Fc^2)/3
4560 reflections	(Δ/σ)max < 0.001
380 parameters	Δρmax = 0.63 e Å^−3
32 restraints	Δρmin = −0.76 e Å^−3

Special details

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. The low occupancy (1/4) water molecules of crystallization were refined isotropically with a common displacement factor. Most of H-atoms near Oxygen atoms were located and placed with O—H distances constrained to 0.95 (1) A P—H distances to be higher than 2.16 (1) A, and for water molecules a H···H of 1.55 (1) A. Additionally, the distances H3Y···O1 and H3Y···O1 were constrained to be approximately equal with the command SADI.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
U1	0.5000	0.5000	0.5000	0.01107 (6)
U2	0.15561 (2)	0.094400 (13)	0.246091 (13)	0.01209 (5)
C1	0.1205 (5)	0.2793 (4)	0.6569 (3)	0.0138 (9)
C2	0.0910 (5)	0.3915 (4)	0.6589 (3)	0.0154 (10)
H2	0.0701	0.4255	0.5921	0.018*
C3	0.0914 (5)	0.4548 (4)	0.7573 (3)	0.0131 (9)
C4	0.1225 (5)	0.4048 (4)	0.8552 (3)	0.0151 (10)
H4	0.1238	0.4476	0.9227	0.018*
C5	0.1520 (6)	0.2919 (4)	0.8546 (4)	0.0169 (10)
C6	0.1499 (5)	0.2295 (4)	0.7556 (3)	0.0160 (10)
H6	0.1685	0.1525	0.7549	0.019*
C7	0.1242 (5)	0.2123 (4)	0.5505 (3)	0.0161 (10)
H7A	0.0584	0.2440	0.4859	0.019*
H7B	0.0761	0.1317	0.5467	0.019*
C8	0.0550 (5)	0.5754 (4)	0.7577 (4)	0.0155 (10)
H8A	0.0924	0.6106	0.6998	0.019*
H8B	0.1170	0.6198	0.8307	0.019*
C9	0.1723 (6)	0.2354 (4)	0.9593 (3)	0.0185 (10)
H9A	0.2253	0.2929	1.0256	0.022*
H9B	0.2414	0.1755	0.9593	0.022*
O1	0.4047 (4)	0.3408 (2)	0.5652 (2)	0.0178 (7)
O2	0.3229 (4)	0.1517 (2)	0.4340 (2)	0.0137 (6)
O3	0.4207 (4)	0.1588 (3)	0.6416 (2)	0.0174 (7)
H3Z	0.407 (6)	0.0785 (10)	0.625 (4)	0.026*
O4	−0.1757 (4)	0.7081 (3)	0.7196 (3)	0.0222 (7)
O5	−0.2546 (4)	0.5022 (2)	0.6310 (2)	0.0155 (7)
O6	−0.1925 (4)	0.5485 (3)	0.8384 (2)	0.0203 (7)
H6Z	−0.298 (2)	0.511 (4)	0.826 (4)	0.030*
O7	−0.1304 (4)	0.2686 (3)	0.9521 (2)	0.0187 (7)
H7Z	−0.183 (5)	0.278 (4)	0.8779 (16)	0.028*
O8	−0.0910 (4)	0.0778 (3)	0.8701 (2)	0.0247 (8)
O9	−0.0071 (4)	0.1393 (3)	1.0798 (2)	0.0177 (7)
O10	0.5602 (4)	0.4138 (2)	0.4020 (2)	0.0175 (7)
O11	0.3323 (4)	0.1138 (3)	0.2055 (2)	0.0201 (7)
O12	−0.0193 (4)	0.0760 (3)	0.2884 (2)	0.0196 (7)
O1W	0.2308 (4)	−0.0671 (3)	0.3499 (3)	0.0265 (8)
H1X	0.291 (5)	−0.059 (3)	0.4262 (14)	0.040*
H1Y	0.211 (6)	−0.1448 (14)	0.319 (3)	0.040*
P1	0.32400 (14)	0.21704 (9)	0.54220 (9)	0.0118 (2)
P2	−0.15338 (14)	0.58652 (9)	0.73305 (9)	0.0134 (2)
P3	−0.02035 (15)	0.17263 (9)	0.96548 (9)	0.0149 (2)
O2W	0.5155 (9)	−0.0534 (7)	0.1215 (6)	0.118 (2)
H2X	0.468 (10)	−0.115 (6)	0.063 (6)	0.176*
H2Y	0.434 (8)	−0.026 (9)	0.148 (8)	0.176*
O3W	0.4836 (5)	0.5382 (4)	0.1702 (3)	0.0422 (10)
H3X	0.510 (4)	0.483 (3)	0.122 (3)	0.063*
H3Y	0.559 (5)	0.546 (3)	0.2421 (19)	0.063*
O4W	−0.2630 (4)	0.2818 (3)	0.7338 (3)	0.0251 (8)
H4X	−0.3760 (15)	0.260 (4)	0.711 (4)	0.038*
H4Y	−0.237 (5)	0.347 (3)	0.701 (4)	0.038*
O5W	0.7331 (5)	0.2286 (4)	0.3410 (3)	0.0475 (11)
H5X	0.675 (7)	0.290 (4)	0.345 (4)	0.071*
H5Y	0.713 (6)	0.199 (2)	0.2649 (14)	0.071*
O6W	0.6083 (4)	0.0599 (3)	0.4279 (3)	0.0195 (7)
H6X	0.668 (4)	0.113 (3)	0.398 (3)	0.029*
H6Y	0.511 (3)	0.085 (3)	0.429 (4)	0.029*
O7W	0.6745 (6)	0.1567 (5)	0.1119 (4)	0.0407 (13)	0.75
H7X	0.638 (7)	0.0785 (15)	0.114 (2)	0.061*	0.75
H7Y	0.782 (4)	0.164 (5)	0.108 (7)	0.061*	0.75
O8W	0.5588 (8)	0.3654 (5)	0.0372 (5)	0.0576 (16)	0.75
H8X	0.580 (12)	0.292 (4)	0.057 (7)	0.086*	0.75
H8Y	0.559 (13)	0.367 (7)	−0.038 (3)	0.086*	0.75
O9W	0.564 (2)	0.2765 (14)	−0.0465 (13)	0.042 (4)	0.25
O10W	0.5434 (17)	0.3060 (13)	0.1697 (12)	0.037 (4)	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
U1	0.01322 (13)	0.00870 (12)	0.01014 (11)	0.00166 (9)	0.00232 (9)	−0.00060 (9)
U2	0.01707 (10)	0.00951 (9)	0.00910 (8)	0.00292 (7)	0.00280 (7)	0.00082 (6)
C1	0.009 (2)	0.015 (2)	0.018 (2)	0.0011 (18)	0.0057 (18)	0.0003 (18)
C2	0.013 (2)	0.021 (2)	0.011 (2)	0.003 (2)	0.0011 (18)	0.0054 (19)
C3	0.010 (2)	0.014 (2)	0.016 (2)	0.0050 (18)	0.0032 (18)	0.0033 (18)
C4	0.015 (2)	0.018 (2)	0.011 (2)	0.0029 (19)	0.0014 (18)	−0.0013 (18)
C5	0.020 (3)	0.018 (2)	0.015 (2)	0.008 (2)	0.006 (2)	0.0053 (19)
C6	0.013 (2)	0.017 (2)	0.019 (2)	0.005 (2)	0.0047 (19)	0.0025 (19)
C7	0.021 (3)	0.015 (2)	0.012 (2)	0.002 (2)	0.0046 (19)	−0.0014 (18)
C8	0.016 (2)	0.014 (2)	0.014 (2)	−0.0010 (19)	0.0020 (19)	−0.0002 (18)
C9	0.028 (3)	0.016 (2)	0.013 (2)	0.011 (2)	0.006 (2)	−0.0009 (19)
O1	0.0248 (19)	0.0107 (16)	0.0160 (15)	−0.0023 (14)	0.0057 (14)	−0.0002 (13)
O2	0.0158 (17)	0.0132 (16)	0.0101 (14)	0.0020 (13)	0.0021 (13)	−0.0015 (12)
O3	0.0221 (18)	0.0169 (17)	0.0125 (15)	0.0058 (15)	0.0020 (13)	0.0050 (13)
O4	0.026 (2)	0.0097 (16)	0.0252 (18)	0.0065 (14)	−0.0025 (15)	0.0019 (14)
O5	0.0157 (17)	0.0106 (15)	0.0153 (15)	0.0015 (13)	−0.0014 (13)	−0.0030 (12)
O6	0.0194 (19)	0.0256 (19)	0.0165 (16)	0.0015 (15)	0.0072 (14)	0.0028 (14)
O7	0.0230 (19)	0.0160 (17)	0.0171 (16)	0.0085 (14)	0.0025 (14)	0.0061 (14)
O8	0.044 (2)	0.0106 (16)	0.0133 (16)	0.0049 (16)	−0.0004 (15)	−0.0009 (13)
O9	0.0254 (19)	0.0162 (16)	0.0106 (15)	0.0045 (14)	0.0022 (13)	0.0056 (13)
O10	0.0207 (18)	0.0143 (16)	0.0164 (16)	0.0025 (14)	0.0052 (14)	−0.0023 (13)
O11	0.0219 (19)	0.0232 (18)	0.0177 (16)	0.0066 (15)	0.0084 (14)	0.0027 (14)
O12	0.0192 (18)	0.0249 (18)	0.0138 (15)	0.0015 (15)	0.0041 (14)	0.0034 (14)
O1W	0.044 (2)	0.0113 (17)	0.0150 (16)	0.0050 (16)	−0.0052 (16)	0.0018 (13)
P1	0.0148 (6)	0.0104 (6)	0.0097 (5)	0.0018 (5)	0.0029 (5)	0.0004 (4)
P2	0.0149 (6)	0.0099 (6)	0.0136 (5)	0.0029 (5)	0.0016 (5)	−0.0002 (4)
P3	0.0239 (7)	0.0091 (6)	0.0095 (5)	0.0039 (5)	0.0013 (5)	0.0011 (4)
O2W	0.114 (6)	0.128 (6)	0.119 (6)	0.006 (5)	0.066 (5)	−0.022 (5)
O3W	0.029 (2)	0.056 (3)	0.043 (2)	0.003 (2)	0.0134 (19)	0.009 (2)
O4W	0.026 (2)	0.0145 (18)	0.0270 (19)	0.0012 (15)	−0.0032 (16)	0.0030 (14)
O5W	0.058 (3)	0.039 (3)	0.050 (3)	−0.006 (2)	0.026 (2)	0.012 (2)
O6W	0.0227 (19)	0.0186 (17)	0.0192 (16)	0.0078 (15)	0.0063 (15)	0.0070 (14)
O7W	0.031 (3)	0.056 (4)	0.040 (3)	0.012 (3)	0.015 (3)	0.009 (3)
O8W	0.048 (4)	0.053 (4)	0.072 (4)	0.013 (3)	0.016 (4)	0.008 (3)
O9W	0.056 (11)	0.040 (10)	0.037 (9)	0.013 (9)	0.020 (8)	0.015 (8)
O10W	0.016 (8)	0.048 (10)	0.039 (9)	−0.008 (7)	0.006 (7)	−0.005 (7)

Geometric parameters (Å, º)

U1—O10	1.774 (3)	C9—H9B	0.9900
U1—O1	2.294 (3)	O1—P1	1.517 (3)
U1—O5^i	2.307 (3)	O2—P1	1.507 (3)
U2—O12	1.765 (3)	O3—P1	1.571 (3)
U2—O11	1.769 (3)	O3—H3Z	0.944 (10)
U2—O8^ii	2.316 (3)	O4—P2	1.500 (3)
U2—O4^iii	2.324 (3)	O5—P2	1.533 (3)
U2—O9^iv	2.326 (3)	O6—P2	1.561 (3)
U2—O2	2.392 (3)	O6—H6Z	0.944 (10)
U2—O1W	2.472 (3)	O7—P3	1.574 (3)
C1—C2	1.388 (6)	O7—H7Z	0.943 (10)
C1—C6	1.400 (6)	O8—P3	1.503 (3)
C1—C7	1.511 (6)	O9—P3	1.510 (3)
C2—C3	1.393 (6)	O1W—H1X	0.948 (10)
C2—H2	0.9500	O1W—H1Y	0.945 (10)
C3—C4	1.393 (6)	O2W—H2X	0.954 (10)
C3—C8	1.505 (6)	O2W—H2Y	0.951 (10)
C4—C5	1.398 (6)	O3W—H3X	0.952 (10)
C4—H4	0.9500	O3W—H3Y	0.946 (10)
C5—C6	1.389 (6)	O4W—H4X	0.947 (10)
C5—C9	1.513 (6)	O4W—H4Y	0.948 (10)
C6—H6	0.9500	O5W—H5X	0.949 (10)
C7—P1	1.786 (5)	O5W—H5Y	0.953 (10)
C7—H7A	0.9900	O6W—H6X	0.942 (10)
C7—H7B	0.9900	O6W—H6Y	0.945 (10)
C8—P2	1.793 (5)	O7W—H7X	0.953 (10)
C8—H8A	0.9900	O7W—H7Y	0.951 (10)
C8—H8B	0.9900	O8W—H8X	0.954 (10)
C9—P3	1.794 (5)	O8W—H8Y	0.955 (10)
C9—H9A	0.9900
O10—U1—O10^v	179.9990 (10)	C1—C7—H7A	109.2
O10—U1—O1	91.00 (12)	P1—C7—H7A	109.2
O10^v—U1—O1	89.01 (12)	C1—C7—H7B	109.2
O10—U1—O1^v	89.00 (12)	P1—C7—H7B	109.2
O10^v—U1—O1^v	90.99 (12)	H7A—C7—H7B	107.9
O1—U1—O1^v	180.00 (8)	C3—C8—P2	114.4 (3)
O10—U1—O5^i	89.89 (12)	C3—C8—H8A	108.7
O10^v—U1—O5^i	90.11 (12)	P2—C8—H8A	108.7
O1—U1—O5^i	88.08 (11)	C3—C8—H8B	108.7
O1^v—U1—O5^i	91.92 (11)	P2—C8—H8B	108.7
O10—U1—O5^iii	90.11 (12)	H8A—C8—H8B	107.6
O10^v—U1—O5^iii	89.89 (12)	C5—C9—P3	109.7 (3)
O1—U1—O5^iii	91.92 (11)	C5—C9—H9A	109.7
O1^v—U1—O5^iii	88.08 (11)	P3—C9—H9A	109.7
O5^i—U1—O5^iii	180.0000 (10)	C5—C9—H9B	109.7
O12—U2—O11	179.23 (14)	P3—C9—H9B	109.7
O12—U2—O8^ii	94.99 (13)	H9A—C9—H9B	108.2
O11—U2—O8^ii	85.65 (13)	P1—O1—U1	149.04 (18)
O12—U2—O4^iii	90.71 (13)	P1—O2—U2	141.33 (18)
O11—U2—O4^iii	88.91 (13)	P1—O3—H3Z	113 (3)
O8^ii—U2—O4^iii	153.07 (10)	P2—O4—U2^iii	162.3 (2)
O12—U2—O9^iv	86.61 (12)	P2—O5—U1^vi	133.58 (17)
O11—U2—O9^iv	93.96 (12)	P2—O6—H6Z	116 (3)
O8^ii—U2—O9^iv	76.92 (10)	P3—O7—H7Z	115 (3)
O4^iii—U2—O9^iv	77.17 (10)	P3—O8—U2^ii	165.0 (2)
O12—U2—O2	91.82 (12)	P3—O9—U2^vii	147.9 (2)
O11—U2—O2	87.43 (12)	U2—O1W—H1X	124 (2)
O8^ii—U2—O2	132.79 (10)	U2—O1W—H1Y	126 (2)
O4^iii—U2—O2	73.10 (10)	H1X—O1W—H1Y	109.8 (16)
O9^iv—U2—O2	150.20 (10)	O2—P1—O1	115.78 (17)
O12—U2—O1W	85.23 (13)	O2—P1—O3	108.96 (17)
O11—U2—O1W	94.61 (13)	O1—P1—O3	105.05 (18)
O8^ii—U2—O1W	68.03 (10)	O2—P1—C7	110.48 (19)
O4^iii—U2—O1W	138.80 (11)	O1—P1—C7	108.69 (19)
O9^iv—U2—O1W	143.08 (11)	O3—P1—C7	107.47 (19)
O2—U2—O1W	66.10 (10)	O4—P2—O5	112.64 (17)
C2—C1—C6	119.1 (4)	O4—P2—O6	112.24 (18)
C2—C1—C7	120.7 (4)	O5—P2—O6	108.73 (18)
C6—C1—C7	120.2 (4)	O4—P2—C8	108.8 (2)
C1—C2—C3	121.1 (4)	O5—P2—C8	109.52 (19)
C1—C2—H2	119.5	O6—P2—C8	104.60 (19)
C3—C2—H2	119.5	O8—P3—O9	115.57 (18)
C4—C3—C2	119.4 (4)	O8—P3—O7	109.37 (18)
C4—C3—C8	120.1 (4)	O9—P3—O7	105.10 (17)
C2—C3—C8	120.5 (4)	O8—P3—C9	108.7 (2)
C3—C4—C5	120.3 (4)	O9—P3—C9	110.43 (19)
C3—C4—H4	119.8	O7—P3—C9	107.39 (19)
C5—C4—H4	119.8	H2X—O2W—H2Y	109.2 (16)
C6—C5—C4	119.6 (4)	H3X—O3W—H3Y	109.2 (16)
C6—C5—C9	120.4 (4)	H4X—O4W—H4Y	109.4 (16)
C4—C5—C9	119.8 (4)	H5X—O5W—H5Y	109.3 (16)
C5—C6—C1	120.6 (4)	H6X—O6W—H6Y	110.1 (15)
C5—C6—H6	119.7	H7X—O7W—H7Y	108.8 (16)
C1—C6—H6	119.7	H8X—O8W—H8Y	108.3 (16)
C1—C7—P1	111.9 (3)	H8X—O9W—H8Y	81.8 (17)
C6—C1—C2—C3	0.5 (7)	U2—O2—P1—O1	−96.7 (3)
C7—C1—C2—C3	−178.4 (4)	U2—O2—P1—O3	145.2 (2)
C1—C2—C3—C4	0.2 (7)	U2—O2—P1—C7	27.3 (3)
C1—C2—C3—C8	−178.4 (4)	U1—O1—P1—O2	17.6 (5)
C2—C3—C4—C5	−0.4 (7)	U1—O1—P1—O3	137.8 (4)
C8—C3—C4—C5	178.2 (4)	U1—O1—P1—C7	−107.4 (4)
C3—C4—C5—C6	−0.1 (7)	C1—C7—P1—O2	−178.7 (3)
C3—C4—C5—C9	−175.1 (4)	C1—C7—P1—O1	−50.6 (3)
C4—C5—C6—C1	0.8 (7)	C1—C7—P1—O3	62.6 (3)
C9—C5—C6—C1	175.8 (4)	U2^iii—O4—P2—O5	178.5 (6)
C2—C1—C6—C5	−1.0 (7)	U2^iii—O4—P2—O6	55.3 (7)
C7—C1—C6—C5	177.9 (4)	U2^iii—O4—P2—C8	−59.9 (7)
C2—C1—C7—P1	95.9 (4)	U1^vi—O5—P2—O4	−31.0 (3)
C6—C1—C7—P1	−82.9 (5)	U1^vi—O5—P2—O6	94.1 (2)
C4—C3—C8—P2	−88.3 (5)	U1^vi—O5—P2—C8	−152.2 (2)
C2—C3—C8—P2	90.4 (5)	C3—C8—P2—O4	−172.1 (3)
C6—C5—C9—P3	−88.1 (5)	C3—C8—P2—O5	−48.6 (3)
C4—C5—C9—P3	86.9 (5)	C3—C8—P2—O6	67.8 (3)
O10—U1—O1—P1	−34.8 (4)	U2^ii—O8—P3—O9	−44.4 (9)
O10^v—U1—O1—P1	145.2 (4)	U2^ii—O8—P3—O7	−162.8 (8)
O5^i—U1—O1—P1	−124.7 (4)	U2^ii—O8—P3—C9	80.3 (9)
O5^iii—U1—O1—P1	55.3 (4)	U2^vii—O9—P3—O8	102.3 (4)
O12—U2—O2—P1	−35.5 (3)	U2^vii—O9—P3—O7	−137.0 (3)
O11—U2—O2—P1	144.4 (3)	U2^vii—O9—P3—C9	−21.5 (4)
O8^ii—U2—O2—P1	−134.0 (3)	C5—C9—P3—O8	64.9 (3)
O4^iii—U2—O2—P1	54.7 (3)	C5—C9—P3—O9	−167.4 (3)
O9^iv—U2—O2—P1	50.9 (4)	C5—C9—P3—O7	−53.3 (3)
O1W—U2—O2—P1	−119.4 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x, y, z−1; (v) −x+1, −y+1, −z+1; (vi) x−1, y, z; (vii) x, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3Z···O6W^viii	0.94 (1)	1.69 (1)	2.625 (4)	168 (4)
O6—H6Z···O3W^iii	0.94 (1)	1.68 (1)	2.609 (5)	168 (4)
O7—H7Z···O4W	0.94 (1)	1.76 (1)	2.696 (4)	171 (5)
O1W—H1X···O6W^viii	0.95 (1)	1.80 (1)	2.747 (4)	173 (4)
O1W—H1Y···O4W^ii	0.95 (1)	1.86 (2)	2.752 (5)	156 (5)
O2W—H2X···O7W^ix	0.95 (1)	2.18 (6)	3.002 (9)	144 (8)
O2W—H2Y···O11	0.95 (1)	2.15 (5)	3.010 (8)	150 (9)
O3W—H3X···O8W	0.95 (1)	1.85 (1)	2.799 (7)	175 (4)
O3W—H3Y···O10	0.95 (1)	2.67 (4)	3.336 (5)	128 (4)
O3W—H3Y···O1^v	0.95 (1)	2.59 (3)	3.333 (5)	136 (3)
O4W—H4X···O3^vi	0.95 (1)	1.95 (2)	2.841 (5)	156 (4)
O4W—H4Y···O5	0.95 (1)	2.12 (2)	3.031 (4)	161 (4)
O5W—H5X···O10	0.95 (1)	2.07 (2)	2.989 (5)	163 (4)
O5W—H5Y···O7W	0.95 (1)	1.87 (1)	2.823 (7)	174 (3)
O6W—H6X···O5W	0.94 (1)	1.73 (2)	2.645 (5)	164 (3)
O6W—H6Y···O2	0.95 (1)	1.93 (1)	2.875 (4)	175 (4)
O7W—H7X···O2W	0.95 (1)	1.81 (2)	2.741 (10)	163 (6)
O7W—H7Y···O9^x	0.95 (1)	2.04 (2)	2.972 (6)	166 (6)
O8W—H8X···O7W	0.95 (1)	1.99 (3)	2.927 (8)	167 (9)
O8W—H8Y···O3W^xi	0.96 (1)	2.07 (5)	2.901 (8)	145 (7)

Symmetry codes: (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vi) x−1, y, z; (viii) −x+1, −y, −z+1; (ix) −x+1, −y, −z; (x) x+1, y, z−1; (xi) −x+1, −y+1, −z.