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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 P\bar 1, 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613034781/bi5030sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613034781/bi5030Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613034781/bi5030IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613034781/bi5030IIIsup4.hkl
Contains datablock III

CCDC references: 978938; 978939; 978940

Computing details top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(I) top
Crystal data top
C3H11FNO14P3U2·4(H2O)F(000) = 3408
Mr = 945.16Dx = 3.170 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 76640 reflections
a = 25.8297 (10) Åθ = 3.6–29.1°
b = 8.7560 (3) ŵ = 16.71 mm1
c = 17.7432 (7) ÅT = 150 K
β = 99.951 (2)°Plate, yellow
V = 3952.5 (3) Å30.05 × 0.03 × 0.01 mm
Z = 8
Data collection top
Bruker X8 Kappa CCD APEX-II
diffractometer
5310 independent reflections
Radiation source: fine-focus sealed tube4724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ω and φ scansθmax = 29.1°, θmin = 3.6°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 3535
Tmin = 0.489, Tmax = 0.921k = 1111
76767 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0206P)2 + 49.9087P]
where P = (Fo2 + 2Fc2)/3
5310 reflections(Δ/σ)max = 0.002
255 parametersΔρmax = 1.52 e Å3
5 restraintsΔρmin = 1.04 e Å3
Crystal data top
C3H11FNO14P3U2·4(H2O)V = 3952.5 (3) Å3
Mr = 945.16Z = 8
Monoclinic, C2/cMo Kα radiation
a = 25.8297 (10) ŵ = 16.71 mm1
b = 8.7560 (3) ÅT = 150 K
c = 17.7432 (7) Å0.05 × 0.03 × 0.01 mm
β = 99.951 (2)°
Data collection top
Bruker X8 Kappa CCD APEX-II
diffractometer
5310 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
4724 reflections with I > 2σ(I)
Tmin = 0.489, Tmax = 0.921Rint = 0.074
76767 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0265 restraints
wR(F2) = 0.059H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0206P)2 + 49.9087P]
where P = (Fo2 + 2Fc2)/3
5310 reflectionsΔρmax = 1.52 e Å3
255 parametersΔρmin = 1.04 e Å3
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. 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 (Å2) top
xyzUiso*/UeqOcc. (<1)
U10.433256 (7)0.59178 (2)0.358471 (10)0.01488 (5)
U20.254508 (7)0.349092 (19)0.400318 (9)0.00984 (5)
C10.37456 (19)0.5151 (6)0.1095 (3)0.0139 (9)
H1A0.36580.61440.13080.017*
H1B0.37830.53340.05560.017*
C20.3155 (2)0.3731 (6)0.1867 (3)0.0148 (10)
H2A0.34620.32100.21710.018*
H2B0.28570.30010.18010.018*
C30.33065 (19)0.2642 (5)0.0650 (3)0.0128 (9)
H3A0.30140.19720.07370.015*
H3B0.36390.21120.08570.015*
F10.23279 (12)0.1321 (3)0.46641 (15)0.0163 (6)
N10.32812 (16)0.4101 (5)0.1090 (2)0.0106 (7)
H1Z0.3002 (16)0.466 (6)0.080 (3)0.016*
O10.43693 (15)0.4568 (5)0.2463 (2)0.0210 (8)
O20.47483 (15)0.5797 (5)0.1385 (2)0.0246 (9)
O30.45060 (16)0.3005 (5)0.1315 (2)0.0253 (9)
H3Z0.437 (3)0.2283 (12)0.164 (3)0.038*
O40.34733 (15)0.5936 (5)0.2926 (2)0.0210 (8)
O50.25783 (14)0.4716 (4)0.28612 (19)0.0152 (7)
O60.27386 (15)0.6555 (4)0.18543 (19)0.0161 (7)
O70.28498 (14)0.4047 (4)0.0612 (2)0.0156 (7)
O80.30686 (17)0.1300 (4)0.0688 (2)0.0206 (8)
H8X0.336 (3)0.062 (12)0.062 (8)0.031*0.50
H8Y0.316 (5)0.088 (15)0.114 (5)0.031*0.50
O90.38037 (15)0.3232 (5)0.0544 (2)0.0234 (9)
O100.43696 (15)0.7738 (5)0.3171 (2)0.0241 (8)
O110.43183 (16)0.4109 (5)0.4025 (2)0.0236 (8)
O120.32043 (14)0.2868 (5)0.4084 (2)0.0202 (8)
O130.18893 (14)0.4123 (4)0.3939 (2)0.0172 (7)
O1W0.48309 (16)0.6959 (6)0.4817 (2)0.0297 (10)
P10.43900 (5)0.45588 (16)0.16175 (7)0.0149 (2)
P20.29844 (5)0.53666 (14)0.24144 (7)0.0104 (2)
P30.32701 (5)0.28900 (14)0.03694 (7)0.0110 (2)
O2W0.4438 (3)0.8888 (7)0.1220 (4)0.0325 (7)*0.70
O3W0.5271 (3)0.0930 (7)0.1467 (4)0.0325 (7)*0.70
O4W0.3383 (4)0.0683 (11)0.2091 (6)0.0325 (7)*0.50
O5W0.3402 (5)0.0180 (14)0.1848 (7)0.0325 (7)*0.40
O6W0.4024 (5)0.0557 (14)0.2286 (7)0.0325 (7)*0.40
O7W0.4228 (5)0.0839 (14)0.2203 (7)0.0325 (7)*0.40
O8W0.3955 (4)0.0687 (11)0.0405 (6)0.0325 (7)*0.50
O9W0.4128 (7)0.1051 (19)0.0197 (9)0.0325 (7)*0.30
O10W0.50000.126 (4)0.25000.0325 (7)*0.20
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
U10.01005 (9)0.02227 (10)0.01238 (9)0.00138 (7)0.00209 (6)0.00142 (7)
U20.01298 (9)0.01007 (8)0.00684 (8)0.00170 (6)0.00276 (6)0.00023 (6)
C10.011 (2)0.014 (2)0.016 (2)0.0033 (18)0.0019 (18)0.0031 (18)
C20.017 (2)0.016 (2)0.012 (2)0.0006 (19)0.0046 (18)0.0053 (18)
C30.011 (2)0.012 (2)0.015 (2)0.0007 (17)0.0028 (18)0.0027 (17)
F10.0282 (17)0.0133 (14)0.0067 (13)0.0068 (12)0.0012 (11)0.0007 (10)
N10.0123 (19)0.0116 (18)0.0081 (17)0.0001 (15)0.0022 (15)0.0036 (14)
O10.0146 (18)0.034 (2)0.0142 (18)0.0028 (16)0.0028 (14)0.0039 (16)
O20.0119 (18)0.033 (2)0.030 (2)0.0044 (16)0.0051 (16)0.0103 (18)
O30.021 (2)0.025 (2)0.029 (2)0.0051 (17)0.0015 (17)0.0033 (17)
O40.0142 (18)0.032 (2)0.0163 (18)0.0038 (16)0.0022 (14)0.0076 (16)
O50.0180 (18)0.0181 (17)0.0110 (16)0.0037 (14)0.0070 (13)0.0043 (13)
O60.026 (2)0.0128 (16)0.0095 (16)0.0039 (15)0.0044 (14)0.0047 (13)
O70.0186 (18)0.0155 (17)0.0127 (16)0.0064 (14)0.0021 (14)0.0023 (13)
O80.032 (2)0.0126 (18)0.0178 (18)0.0020 (15)0.0069 (16)0.0049 (14)
O90.0137 (18)0.039 (2)0.0179 (19)0.0030 (16)0.0051 (15)0.0084 (17)
O100.0176 (19)0.026 (2)0.029 (2)0.0029 (16)0.0055 (16)0.0024 (17)
O110.020 (2)0.026 (2)0.024 (2)0.0030 (16)0.0043 (16)0.0004 (16)
O120.0125 (18)0.024 (2)0.024 (2)0.0019 (15)0.0036 (15)0.0004 (16)
O130.0149 (18)0.0202 (18)0.0169 (18)0.0033 (14)0.0039 (14)0.0006 (14)
O1W0.0132 (19)0.049 (3)0.025 (2)0.0003 (18)0.0028 (16)0.0107 (19)
P10.0108 (6)0.0194 (6)0.0144 (6)0.0004 (5)0.0021 (5)0.0012 (5)
P20.0116 (6)0.0130 (5)0.0066 (5)0.0000 (5)0.0016 (4)0.0028 (4)
P30.0122 (6)0.0105 (5)0.0103 (5)0.0005 (4)0.0018 (4)0.0008 (4)
Geometric parameters (Å, º) top
U1—O101.764 (4)C2—P21.826 (5)
U1—O111.769 (4)C2—H2A0.9900
U1—O42.323 (4)C2—H2B0.9900
U1—O12.331 (4)C3—N11.505 (6)
U1—O9i2.354 (4)C3—P31.808 (5)
U1—O2ii2.368 (4)C3—H3A0.9900
U1—O1W2.510 (4)C3—H3B0.9900
U2—O131.767 (4)N1—H1Z0.945 (10)
U2—O121.770 (4)O1—P11.510 (4)
U2—O52.307 (3)O2—P11.527 (4)
U2—O6iii2.311 (3)O3—P11.511 (4)
U2—F1iv2.336 (3)O3—H3Z0.956 (10)
U2—F12.351 (3)O4—P21.507 (4)
U2—O7i2.355 (4)O5—P21.530 (3)
U2—U2iv3.9829 (3)O6—P21.502 (4)
C1—N11.510 (6)O7—P31.493 (4)
C1—P11.835 (5)O8—P31.558 (4)
C1—H1A0.9900O8—H8X0.949 (10)
C1—H1B0.9900O8—H8Y0.949 (10)
C2—N11.507 (6)O9—P31.494 (4)
O10—U1—O11177.74 (19)N1—C1—H1B107.6
O10—U1—O484.27 (17)P1—C1—H1B107.6
O11—U1—O497.91 (17)H1A—C1—H1B107.1
O10—U1—O195.15 (17)N1—C2—P2115.3 (3)
O11—U1—O186.01 (16)N1—C2—H2A108.4
O4—U1—O175.54 (13)P2—C2—H2A108.4
O10—U1—O9i93.82 (17)N1—C2—H2B108.4
O11—U1—O9i86.23 (17)P2—C2—H2B108.4
O4—U1—O9i73.50 (13)H2A—C2—H2B107.5
O1—U1—O9i146.64 (13)N1—C3—P3114.7 (3)
O10—U1—O2ii85.63 (17)N1—C3—H3A108.6
O11—U1—O2ii92.70 (17)P3—C3—H3A108.6
O4—U1—O2ii151.51 (14)N1—C3—H3B108.6
O1—U1—O2ii78.94 (13)P3—C3—H3B108.6
O9i—U1—O2ii133.83 (13)H3A—C3—H3B107.6
O10—U1—O1W88.73 (18)U2iv—F1—U2116.37 (11)
O11—U1—O1W89.24 (17)C3—N1—C2109.1 (4)
O4—U1—O1W137.52 (13)C3—N1—C1114.5 (4)
O1—U1—O1W146.92 (13)C2—N1—C1115.1 (4)
O9i—U1—O1W65.24 (13)C3—N1—H1Z105 (4)
O2ii—U1—O1W68.60 (13)C2—N1—H1Z110 (4)
O13—U2—O12179.02 (17)C1—N1—H1Z103 (4)
O13—U2—O588.77 (15)P1—O1—U1149.9 (3)
O12—U2—O591.88 (15)P1—O2—U1ii132.6 (2)
O13—U2—O6iii89.78 (15)P1—O3—H3Z105.6 (10)
O12—U2—O6iii91.04 (16)P2—O4—U1158.3 (3)
O5—U2—O6iii79.54 (12)P2—O5—U2139.6 (2)
O13—U2—F1iv90.48 (14)P2—O6—U2v173.5 (2)
O12—U2—F1iv88.57 (15)P3—O7—U2vi153.5 (2)
O5—U2—F1iv146.73 (11)P3—O8—H8X108 (9)
O6iii—U2—F1iv133.72 (11)P3—O8—H8Y122 (8)
O13—U2—F188.66 (14)H8X—O8—H8Y64 (10)
O12—U2—F191.14 (15)P3—O9—U1vi149.3 (2)
O5—U2—F1149.54 (11)O1—P1—O3113.6 (2)
O6iii—U2—F170.11 (11)O1—P1—O2113.1 (2)
F1iv—U2—F163.63 (11)O3—P1—O2112.1 (2)
O13—U2—O7i90.02 (15)O1—P1—C1108.4 (2)
O12—U2—O7i89.43 (16)O3—P1—C1107.0 (2)
O5—U2—O7i76.57 (12)O2—P1—C1101.7 (2)
O6iii—U2—O7i156.11 (12)O6—P2—O4112.6 (2)
F1iv—U2—O7i70.17 (11)O6—P2—O5110.6 (2)
F1—U2—O7i133.77 (11)O4—P2—O5112.9 (2)
O13—U2—U2iv89.49 (12)O6—P2—C2107.7 (2)
O12—U2—U2iv89.83 (12)O4—P2—C2109.0 (2)
O5—U2—U2iv177.80 (9)O5—P2—C2103.5 (2)
O6iii—U2—U2iv101.80 (9)O7—P3—O9117.1 (2)
F1iv—U2—U2iv31.93 (7)O7—P3—O8108.7 (2)
F1—U2—U2iv31.71 (7)O9—P3—O8111.5 (2)
O7i—U2—U2iv102.08 (8)O7—P3—C3106.2 (2)
N1—C1—P1118.8 (3)O9—P3—C3109.9 (2)
N1—C1—H1A107.6O8—P3—C3102.2 (2)
P1—C1—H1A107.6
O13—U2—F1—U2iv91.20 (17)O7i—U2—O5—P267.8 (3)
O12—U2—F1—U2iv87.84 (18)U1—O1—P1—O3169.7 (4)
O5—U2—F1—U2iv176.50 (18)U1—O1—P1—O240.5 (5)
O6iii—U2—F1—U2iv178.54 (18)U1—O1—P1—C171.4 (5)
F1iv—U2—F1—U2iv0.001 (2)U1ii—O2—P1—O183.1 (4)
O7i—U2—F1—U2iv2.5 (2)U1ii—O2—P1—O346.9 (4)
P3—C3—N1—C2163.4 (3)U1ii—O2—P1—C1160.9 (3)
P3—C3—N1—C166.0 (5)N1—C1—P1—O168.3 (4)
P2—C2—N1—C3168.8 (3)N1—C1—P1—O354.6 (4)
P2—C2—N1—C161.0 (5)N1—C1—P1—O2172.4 (4)
P1—C1—N1—C368.4 (5)U1—O4—P2—O6134.5 (6)
P1—C1—N1—C259.2 (5)U1—O4—P2—O599.4 (6)
O10—U1—O1—P13.3 (5)U1—O4—P2—C215.0 (7)
O11—U1—O1—P1178.7 (5)U2—O5—P2—O6157.2 (3)
O4—U1—O1—P179.5 (5)U2—O5—P2—O430.1 (4)
O9i—U1—O1—P1101.7 (5)U2—O5—P2—C287.6 (4)
O2ii—U1—O1—P187.8 (5)N1—C2—P2—O629.2 (4)
O1W—U1—O1—P198.9 (5)N1—C2—P2—O493.3 (4)
O10—U1—O4—P2131.0 (7)N1—C2—P2—O5146.3 (3)
O11—U1—O4—P249.6 (7)U2vi—O7—P3—O918.8 (6)
O1—U1—O4—P234.1 (6)U2vi—O7—P3—O8146.2 (4)
O9i—U1—O4—P2133.3 (7)U2vi—O7—P3—C3104.4 (5)
O2ii—U1—O4—P261.2 (8)U1vi—O9—P3—O745.2 (6)
O1W—U1—O4—P2147.2 (6)U1vi—O9—P3—O880.9 (5)
O13—U2—O5—P2158.1 (3)U1vi—O9—P3—C3166.5 (5)
O12—U2—O5—P221.2 (4)N1—C3—P3—O743.0 (4)
O6iii—U2—O5—P2111.9 (3)N1—C3—P3—O984.6 (4)
F1iv—U2—O5—P269.1 (4)N1—C3—P3—O8156.9 (3)
F1—U2—O5—P2116.7 (3)
Symmetry codes: (i) x, y+1, z+1/2; (ii) x+1, y, z+1/2; (iii) x+1/2, y1/2, 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, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1Z···F1v0.95 (1)1.81 (3)2.705 (5)157 (5)
O3—H3Z···O6W0.96 (1)2.19 (2)3.139 (13)175 (6)
O3—H3Z···O7W0.96 (1)1.70 (2)2.643 (13)171 (5)
O8—H8Y···O4W0.95 (1)1.88 (4)2.802 (10)163 (13)
O8—H8Y···O5W0.95 (1)1.62 (3)2.560 (13)171 (14)
O8—H8X···O8W0.95 (1)1.90 (2)2.850 (11)176 (13)
O8—H8X···O9W0.95 (1)2.48 (3)3.415 (17)170 (12)
Symmetry code: (v) x+1/2, y+1/2, z+1/2.
(II) top
Crystal data top
C8H10O8P2UF(000) = 488
Mr = 534.13Dx = 2.714 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8989 reflections
a = 10.9522 (13) Åθ = 3.7–33.1°
b = 6.4691 (7) ŵ = 12.69 mm1
c = 9.2802 (10) ÅT = 296 K
β = 96.333 (9)°Plate, yellow
V = 653.50 (13) Å30.03 × 0.02 × 0.01 mm
Z = 2
Data collection top
Bruker X8 Kappa CCD APEX-II
diffractometer
2475 independent reflections
Radiation source: fine-focus sealed tube1556 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω and φ scansθmax = 33.1°, θmin = 3.7°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 1616
Tmin = 0.702, Tmax = 0.939k = 99
8989 measured reflectionsl = 1314
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0205P)2]
where P = (Fo2 + 2Fc2)/3
2475 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 1.91 e Å3
1 restraintΔρmin = 2.74 e Å3
Crystal data top
C8H10O8P2UV = 653.50 (13) Å3
Mr = 534.13Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.9522 (13) ŵ = 12.69 mm1
b = 6.4691 (7) ÅT = 296 K
c = 9.2802 (10) Å0.03 × 0.02 × 0.01 mm
β = 96.333 (9)°
Data collection top
Bruker X8 Kappa CCD APEX-II
diffractometer
2475 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
1556 reflections with I > 2σ(I)
Tmin = 0.702, Tmax = 0.939Rint = 0.055
8989 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 1.91 e Å3
2475 reflectionsΔρmin = 2.74 e Å3
91 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
xyzUiso*/Ueq
U10.50000.00001.00000.01518 (7)
P10.70512 (12)0.3134 (2)0.81343 (14)0.0175 (3)
O30.6449 (3)0.4402 (5)0.6896 (4)0.0260 (9)
O40.5598 (4)0.2530 (5)0.9798 (4)0.0273 (9)
O10.6318 (3)0.1263 (6)0.8481 (4)0.0264 (8)
O20.7302 (4)0.4518 (5)0.9517 (4)0.0270 (9)
H2Z0.671 (3)0.529 (7)0.962 (7)0.041*
C10.8534 (5)0.2358 (8)0.7741 (5)0.0227 (11)
H1A0.84400.15290.68640.027*
H1B0.89940.35860.75370.027*
C20.9290 (5)0.1135 (8)0.8917 (5)0.0172 (11)
C30.8957 (5)0.0858 (9)0.9271 (6)0.0232 (12)
H30.82530.14500.87880.028*
C41.0343 (5)0.1976 (8)0.9667 (6)0.0228 (11)
H41.05800.33110.94510.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
U10.01212 (10)0.01505 (11)0.01776 (11)0.00108 (18)0.00114 (7)0.00388 (16)
P10.0131 (6)0.0221 (6)0.0164 (6)0.0029 (5)0.0015 (5)0.0021 (5)
O30.0175 (19)0.034 (2)0.0248 (19)0.0051 (15)0.0033 (15)0.0050 (15)
O40.028 (2)0.0198 (19)0.034 (2)0.0064 (17)0.0030 (17)0.0047 (16)
O10.020 (2)0.028 (2)0.032 (2)0.0052 (17)0.0050 (16)0.0005 (17)
O20.027 (2)0.025 (2)0.026 (2)0.0110 (16)0.0074 (16)0.0061 (15)
C10.020 (3)0.029 (3)0.018 (3)0.006 (2)0.002 (2)0.007 (2)
C20.012 (3)0.024 (3)0.016 (3)0.005 (2)0.0025 (19)0.002 (2)
C30.016 (3)0.027 (3)0.026 (3)0.000 (2)0.002 (2)0.001 (2)
C40.021 (3)0.019 (2)0.028 (3)0.000 (2)0.003 (2)0.001 (2)
Geometric parameters (Å, º) top
U1—O41.781 (3)O2—H2Z0.834 (10)
U1—O4i1.781 (3)C1—C21.518 (7)
U1—O3ii2.269 (4)C1—H1A0.9700
U1—O3iii2.269 (4)C1—H1B0.9700
U1—O12.278 (3)C2—C31.389 (7)
U1—O1i2.278 (3)C2—C41.390 (7)
P1—O31.504 (4)C3—C4v1.384 (7)
P1—O11.507 (4)C3—H30.9300
P1—O21.564 (4)C4—C3v1.384 (7)
P1—C11.776 (5)C4—H40.9300
O3—U1iv2.269 (4)
O4—U1—O4i179.999 (2)P1—O1—U1144.0 (2)
O4—U1—O3ii90.25 (15)P1—O2—H2Z111 (4)
O4—U1—O3iii89.75 (15)C2—C1—P1115.9 (3)
O3ii—U1—O3iii180.0C2—C1—H1A108.3
O4—U1—O189.93 (15)P1—C1—H1A108.3
O3ii—U1—O188.95 (14)C2—C1—H1B108.3
O3iii—U1—O191.05 (14)P1—C1—H1B108.3
O4—U1—O1i90.07 (15)H1A—C1—H1B107.4
O3ii—U1—O1i91.05 (14)C3—C2—C4118.0 (5)
O3iii—U1—O1i88.95 (14)C3—C2—C1121.2 (5)
O1—U1—O1i179.9990 (10)C4—C2—C1120.8 (5)
O3—P1—O1113.7 (2)C4v—C3—C2120.9 (6)
O3—P1—O2109.7 (2)C4v—C3—H3119.5
O1—P1—O2109.5 (2)C2—C3—H3119.5
O3—P1—C1109.3 (2)C3v—C4—C2121.1 (5)
O1—P1—C1109.7 (2)C3v—C4—H4119.5
O2—P1—C1104.4 (2)C2—C4—H4119.5
P1—O3—U1iv153.6 (2)
O1—P1—O3—U1iv9.1 (6)O3—P1—C1—C2177.5 (4)
O2—P1—O3—U1iv132.2 (5)O1—P1—C1—C257.2 (5)
C1—P1—O3—U1iv113.9 (5)O2—P1—C1—C260.2 (4)
O3—P1—O1—U199.5 (4)P1—C1—C2—C368.5 (6)
O2—P1—O1—U123.7 (5)P1—C1—C2—C4112.0 (5)
C1—P1—O1—U1137.7 (4)C4—C2—C3—C4v0.4 (8)
O4—U1—O1—P1149.5 (4)C1—C2—C3—C4v179.2 (5)
O4i—U1—O1—P130.5 (4)C3—C2—C4—C3v0.4 (8)
O3ii—U1—O1—P159.3 (4)C1—C2—C4—C3v179.2 (5)
O3iii—U1—O1—P1120.7 (4)
Symmetry codes: (i) x+1, y, z+2; (ii) x, y+1/2, z+1/2; (iii) x+1, y1/2, z+3/2; (iv) x+1, y+1/2, z+3/2; (v) x+2, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2Z···O4vi0.83 (1)1.88 (2)2.703 (5)168 (5)
Symmetry code: (vi) x, y+1, z.
(III) top
Crystal data top
C9H14O13P3U1.50·7(H2O)Z = 2
Mr = 906.27F(000) = 850
Triclinic, P1Dx = 2.416 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7982 (3) ÅCell parameters from 54948 reflections
b = 11.8876 (4) Åθ = 2.3–25.4°
c = 12.6446 (4) ŵ = 10.03 mm1
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) Å3
Data collection top
Bruker X8 Kappa CCD APEX-II
diffractometer
4560 independent reflections
Radiation source: fine-focus sealed tube4004 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω and φ scansθmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 1010
Tmin = 0.825, Tmax = 0.906k = 1414
54948 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.041H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0095P)2 + 3.2581P]
where P = (Fo2 + 2Fc2)/3
4560 reflections(Δ/σ)max < 0.001
380 parametersΔρmax = 0.63 e Å3
32 restraintsΔρmin = 0.76 e Å3
Crystal data top
C9H14O13P3U1.50·7(H2O)γ = 96.980 (2)°
Mr = 906.27V = 1245.89 (7) Å3
Triclinic, P1Z = 2
a = 8.7982 (3) ÅMo Kα radiation
b = 11.8876 (4) ŵ = 10.03 mm1
c = 12.6446 (4) ÅT = 150 K
α = 95.219 (2)°0.02 × 0.02 × 0.01 mm
β = 106.752 (2)°
Data collection top
Bruker X8 Kappa CCD APEX-II
diffractometer
4560 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
4004 reflections with I > 2σ(I)
Tmin = 0.825, Tmax = 0.906Rint = 0.064
54948 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02132 restraints
wR(F2) = 0.041H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.63 e Å3
4560 reflectionsΔρmin = 0.76 e Å3
380 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. 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 (Å2) top
xyzUiso*/UeqOcc. (<1)
U10.50000.50000.50000.01107 (6)
U20.15561 (2)0.094400 (13)0.246091 (13)0.01209 (5)
C10.1205 (5)0.2793 (4)0.6569 (3)0.0138 (9)
C20.0910 (5)0.3915 (4)0.6589 (3)0.0154 (10)
H20.07010.42550.59210.018*
C30.0914 (5)0.4548 (4)0.7573 (3)0.0131 (9)
C40.1225 (5)0.4048 (4)0.8552 (3)0.0151 (10)
H40.12380.44760.92270.018*
C50.1520 (6)0.2919 (4)0.8546 (4)0.0169 (10)
C60.1499 (5)0.2295 (4)0.7556 (3)0.0160 (10)
H60.16850.15250.75490.019*
C70.1242 (5)0.2123 (4)0.5505 (3)0.0161 (10)
H7A0.05840.24400.48590.019*
H7B0.07610.13170.54670.019*
C80.0550 (5)0.5754 (4)0.7577 (4)0.0155 (10)
H8A0.09240.61060.69980.019*
H8B0.11700.61980.83070.019*
C90.1723 (6)0.2354 (4)0.9593 (3)0.0185 (10)
H9A0.22530.29291.02560.022*
H9B0.24140.17550.95930.022*
O10.4047 (4)0.3408 (2)0.5652 (2)0.0178 (7)
O20.3229 (4)0.1517 (2)0.4340 (2)0.0137 (6)
O30.4207 (4)0.1588 (3)0.6416 (2)0.0174 (7)
H3Z0.407 (6)0.0785 (10)0.625 (4)0.026*
O40.1757 (4)0.7081 (3)0.7196 (3)0.0222 (7)
O50.2546 (4)0.5022 (2)0.6310 (2)0.0155 (7)
O60.1925 (4)0.5485 (3)0.8384 (2)0.0203 (7)
H6Z0.298 (2)0.511 (4)0.826 (4)0.030*
O70.1304 (4)0.2686 (3)0.9521 (2)0.0187 (7)
H7Z0.183 (5)0.278 (4)0.8779 (16)0.028*
O80.0910 (4)0.0778 (3)0.8701 (2)0.0247 (8)
O90.0071 (4)0.1393 (3)1.0798 (2)0.0177 (7)
O100.5602 (4)0.4138 (2)0.4020 (2)0.0175 (7)
O110.3323 (4)0.1138 (3)0.2055 (2)0.0201 (7)
O120.0193 (4)0.0760 (3)0.2884 (2)0.0196 (7)
O1W0.2308 (4)0.0671 (3)0.3499 (3)0.0265 (8)
H1X0.291 (5)0.059 (3)0.4262 (14)0.040*
H1Y0.211 (6)0.1448 (14)0.319 (3)0.040*
P10.32400 (14)0.21704 (9)0.54220 (9)0.0118 (2)
P20.15338 (14)0.58652 (9)0.73305 (9)0.0134 (2)
P30.02035 (15)0.17263 (9)0.96548 (9)0.0149 (2)
O2W0.5155 (9)0.0534 (7)0.1215 (6)0.118 (2)
H2X0.468 (10)0.115 (6)0.063 (6)0.176*
H2Y0.434 (8)0.026 (9)0.148 (8)0.176*
O3W0.4836 (5)0.5382 (4)0.1702 (3)0.0422 (10)
H3X0.510 (4)0.483 (3)0.122 (3)0.063*
H3Y0.559 (5)0.546 (3)0.2421 (19)0.063*
O4W0.2630 (4)0.2818 (3)0.7338 (3)0.0251 (8)
H4X0.3760 (15)0.260 (4)0.711 (4)0.038*
H4Y0.237 (5)0.347 (3)0.701 (4)0.038*
O5W0.7331 (5)0.2286 (4)0.3410 (3)0.0475 (11)
H5X0.675 (7)0.290 (4)0.345 (4)0.071*
H5Y0.713 (6)0.199 (2)0.2649 (14)0.071*
O6W0.6083 (4)0.0599 (3)0.4279 (3)0.0195 (7)
H6X0.668 (4)0.113 (3)0.398 (3)0.029*
H6Y0.511 (3)0.085 (3)0.429 (4)0.029*
O7W0.6745 (6)0.1567 (5)0.1119 (4)0.0407 (13)0.75
H7X0.638 (7)0.0785 (15)0.114 (2)0.061*0.75
H7Y0.782 (4)0.164 (5)0.108 (7)0.061*0.75
O8W0.5588 (8)0.3654 (5)0.0372 (5)0.0576 (16)0.75
H8X0.580 (12)0.292 (4)0.057 (7)0.086*0.75
H8Y0.559 (13)0.367 (7)0.038 (3)0.086*0.75
O9W0.564 (2)0.2765 (14)0.0465 (13)0.042 (4)0.25
O10W0.5434 (17)0.3060 (13)0.1697 (12)0.037 (4)0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
U10.01322 (13)0.00870 (12)0.01014 (11)0.00166 (9)0.00232 (9)0.00060 (9)
U20.01707 (10)0.00951 (9)0.00910 (8)0.00292 (7)0.00280 (7)0.00082 (6)
C10.009 (2)0.015 (2)0.018 (2)0.0011 (18)0.0057 (18)0.0003 (18)
C20.013 (2)0.021 (2)0.011 (2)0.003 (2)0.0011 (18)0.0054 (19)
C30.010 (2)0.014 (2)0.016 (2)0.0050 (18)0.0032 (18)0.0033 (18)
C40.015 (2)0.018 (2)0.011 (2)0.0029 (19)0.0014 (18)0.0013 (18)
C50.020 (3)0.018 (2)0.015 (2)0.008 (2)0.006 (2)0.0053 (19)
C60.013 (2)0.017 (2)0.019 (2)0.005 (2)0.0047 (19)0.0025 (19)
C70.021 (3)0.015 (2)0.012 (2)0.002 (2)0.0046 (19)0.0014 (18)
C80.016 (2)0.014 (2)0.014 (2)0.0010 (19)0.0020 (19)0.0002 (18)
C90.028 (3)0.016 (2)0.013 (2)0.011 (2)0.006 (2)0.0009 (19)
O10.0248 (19)0.0107 (16)0.0160 (15)0.0023 (14)0.0057 (14)0.0002 (13)
O20.0158 (17)0.0132 (16)0.0101 (14)0.0020 (13)0.0021 (13)0.0015 (12)
O30.0221 (18)0.0169 (17)0.0125 (15)0.0058 (15)0.0020 (13)0.0050 (13)
O40.026 (2)0.0097 (16)0.0252 (18)0.0065 (14)0.0025 (15)0.0019 (14)
O50.0157 (17)0.0106 (15)0.0153 (15)0.0015 (13)0.0014 (13)0.0030 (12)
O60.0194 (19)0.0256 (19)0.0165 (16)0.0015 (15)0.0072 (14)0.0028 (14)
O70.0230 (19)0.0160 (17)0.0171 (16)0.0085 (14)0.0025 (14)0.0061 (14)
O80.044 (2)0.0106 (16)0.0133 (16)0.0049 (16)0.0004 (15)0.0009 (13)
O90.0254 (19)0.0162 (16)0.0106 (15)0.0045 (14)0.0022 (13)0.0056 (13)
O100.0207 (18)0.0143 (16)0.0164 (16)0.0025 (14)0.0052 (14)0.0023 (13)
O110.0219 (19)0.0232 (18)0.0177 (16)0.0066 (15)0.0084 (14)0.0027 (14)
O120.0192 (18)0.0249 (18)0.0138 (15)0.0015 (15)0.0041 (14)0.0034 (14)
O1W0.044 (2)0.0113 (17)0.0150 (16)0.0050 (16)0.0052 (16)0.0018 (13)
P10.0148 (6)0.0104 (6)0.0097 (5)0.0018 (5)0.0029 (5)0.0004 (4)
P20.0149 (6)0.0099 (6)0.0136 (5)0.0029 (5)0.0016 (5)0.0002 (4)
P30.0239 (7)0.0091 (6)0.0095 (5)0.0039 (5)0.0013 (5)0.0011 (4)
O2W0.114 (6)0.128 (6)0.119 (6)0.006 (5)0.066 (5)0.022 (5)
O3W0.029 (2)0.056 (3)0.043 (2)0.003 (2)0.0134 (19)0.009 (2)
O4W0.026 (2)0.0145 (18)0.0270 (19)0.0012 (15)0.0032 (16)0.0030 (14)
O5W0.058 (3)0.039 (3)0.050 (3)0.006 (2)0.026 (2)0.012 (2)
O6W0.0227 (19)0.0186 (17)0.0192 (16)0.0078 (15)0.0063 (15)0.0070 (14)
O7W0.031 (3)0.056 (4)0.040 (3)0.012 (3)0.015 (3)0.009 (3)
O8W0.048 (4)0.053 (4)0.072 (4)0.013 (3)0.016 (4)0.008 (3)
O9W0.056 (11)0.040 (10)0.037 (9)0.013 (9)0.020 (8)0.015 (8)
O10W0.016 (8)0.048 (10)0.039 (9)0.008 (7)0.006 (7)0.005 (7)
Geometric parameters (Å, º) top
U1—O101.774 (3)C9—H9B0.9900
U1—O12.294 (3)O1—P11.517 (3)
U1—O5i2.307 (3)O2—P11.507 (3)
U2—O121.765 (3)O3—P11.571 (3)
U2—O111.769 (3)O3—H3Z0.944 (10)
U2—O8ii2.316 (3)O4—P21.500 (3)
U2—O4iii2.324 (3)O5—P21.533 (3)
U2—O9iv2.326 (3)O6—P21.561 (3)
U2—O22.392 (3)O6—H6Z0.944 (10)
U2—O1W2.472 (3)O7—P31.574 (3)
C1—C21.388 (6)O7—H7Z0.943 (10)
C1—C61.400 (6)O8—P31.503 (3)
C1—C71.511 (6)O9—P31.510 (3)
C2—C31.393 (6)O1W—H1X0.948 (10)
C2—H20.9500O1W—H1Y0.945 (10)
C3—C41.393 (6)O2W—H2X0.954 (10)
C3—C81.505 (6)O2W—H2Y0.951 (10)
C4—C51.398 (6)O3W—H3X0.952 (10)
C4—H40.9500O3W—H3Y0.946 (10)
C5—C61.389 (6)O4W—H4X0.947 (10)
C5—C91.513 (6)O4W—H4Y0.948 (10)
C6—H60.9500O5W—H5X0.949 (10)
C7—P11.786 (5)O5W—H5Y0.953 (10)
C7—H7A0.9900O6W—H6X0.942 (10)
C7—H7B0.9900O6W—H6Y0.945 (10)
C8—P21.793 (5)O7W—H7X0.953 (10)
C8—H8A0.9900O7W—H7Y0.951 (10)
C8—H8B0.9900O8W—H8X0.954 (10)
C9—P31.794 (5)O8W—H8Y0.955 (10)
C9—H9A0.9900
O10—U1—O10v179.9990 (10)C1—C7—H7A109.2
O10—U1—O191.00 (12)P1—C7—H7A109.2
O10v—U1—O189.01 (12)C1—C7—H7B109.2
O10—U1—O1v89.00 (12)P1—C7—H7B109.2
O10v—U1—O1v90.99 (12)H7A—C7—H7B107.9
O1—U1—O1v180.00 (8)C3—C8—P2114.4 (3)
O10—U1—O5i89.89 (12)C3—C8—H8A108.7
O10v—U1—O5i90.11 (12)P2—C8—H8A108.7
O1—U1—O5i88.08 (11)C3—C8—H8B108.7
O1v—U1—O5i91.92 (11)P2—C8—H8B108.7
O10—U1—O5iii90.11 (12)H8A—C8—H8B107.6
O10v—U1—O5iii89.89 (12)C5—C9—P3109.7 (3)
O1—U1—O5iii91.92 (11)C5—C9—H9A109.7
O1v—U1—O5iii88.08 (11)P3—C9—H9A109.7
O5i—U1—O5iii180.0000 (10)C5—C9—H9B109.7
O12—U2—O11179.23 (14)P3—C9—H9B109.7
O12—U2—O8ii94.99 (13)H9A—C9—H9B108.2
O11—U2—O8ii85.65 (13)P1—O1—U1149.04 (18)
O12—U2—O4iii90.71 (13)P1—O2—U2141.33 (18)
O11—U2—O4iii88.91 (13)P1—O3—H3Z113 (3)
O8ii—U2—O4iii153.07 (10)P2—O4—U2iii162.3 (2)
O12—U2—O9iv86.61 (12)P2—O5—U1vi133.58 (17)
O11—U2—O9iv93.96 (12)P2—O6—H6Z116 (3)
O8ii—U2—O9iv76.92 (10)P3—O7—H7Z115 (3)
O4iii—U2—O9iv77.17 (10)P3—O8—U2ii165.0 (2)
O12—U2—O291.82 (12)P3—O9—U2vii147.9 (2)
O11—U2—O287.43 (12)U2—O1W—H1X124 (2)
O8ii—U2—O2132.79 (10)U2—O1W—H1Y126 (2)
O4iii—U2—O273.10 (10)H1X—O1W—H1Y109.8 (16)
O9iv—U2—O2150.20 (10)O2—P1—O1115.78 (17)
O12—U2—O1W85.23 (13)O2—P1—O3108.96 (17)
O11—U2—O1W94.61 (13)O1—P1—O3105.05 (18)
O8ii—U2—O1W68.03 (10)O2—P1—C7110.48 (19)
O4iii—U2—O1W138.80 (11)O1—P1—C7108.69 (19)
O9iv—U2—O1W143.08 (11)O3—P1—C7107.47 (19)
O2—U2—O1W66.10 (10)O4—P2—O5112.64 (17)
C2—C1—C6119.1 (4)O4—P2—O6112.24 (18)
C2—C1—C7120.7 (4)O5—P2—O6108.73 (18)
C6—C1—C7120.2 (4)O4—P2—C8108.8 (2)
C1—C2—C3121.1 (4)O5—P2—C8109.52 (19)
C1—C2—H2119.5O6—P2—C8104.60 (19)
C3—C2—H2119.5O8—P3—O9115.57 (18)
C4—C3—C2119.4 (4)O8—P3—O7109.37 (18)
C4—C3—C8120.1 (4)O9—P3—O7105.10 (17)
C2—C3—C8120.5 (4)O8—P3—C9108.7 (2)
C3—C4—C5120.3 (4)O9—P3—C9110.43 (19)
C3—C4—H4119.8O7—P3—C9107.39 (19)
C5—C4—H4119.8H2X—O2W—H2Y109.2 (16)
C6—C5—C4119.6 (4)H3X—O3W—H3Y109.2 (16)
C6—C5—C9120.4 (4)H4X—O4W—H4Y109.4 (16)
C4—C5—C9119.8 (4)H5X—O5W—H5Y109.3 (16)
C5—C6—C1120.6 (4)H6X—O6W—H6Y110.1 (15)
C5—C6—H6119.7H7X—O7W—H7Y108.8 (16)
C1—C6—H6119.7H8X—O8W—H8Y108.3 (16)
C1—C7—P1111.9 (3)H8X—O9W—H8Y81.8 (17)
C6—C1—C2—C30.5 (7)U2—O2—P1—O196.7 (3)
C7—C1—C2—C3178.4 (4)U2—O2—P1—O3145.2 (2)
C1—C2—C3—C40.2 (7)U2—O2—P1—C727.3 (3)
C1—C2—C3—C8178.4 (4)U1—O1—P1—O217.6 (5)
C2—C3—C4—C50.4 (7)U1—O1—P1—O3137.8 (4)
C8—C3—C4—C5178.2 (4)U1—O1—P1—C7107.4 (4)
C3—C4—C5—C60.1 (7)C1—C7—P1—O2178.7 (3)
C3—C4—C5—C9175.1 (4)C1—C7—P1—O150.6 (3)
C4—C5—C6—C10.8 (7)C1—C7—P1—O362.6 (3)
C9—C5—C6—C1175.8 (4)U2iii—O4—P2—O5178.5 (6)
C2—C1—C6—C51.0 (7)U2iii—O4—P2—O655.3 (7)
C7—C1—C6—C5177.9 (4)U2iii—O4—P2—C859.9 (7)
C2—C1—C7—P195.9 (4)U1vi—O5—P2—O431.0 (3)
C6—C1—C7—P182.9 (5)U1vi—O5—P2—O694.1 (2)
C4—C3—C8—P288.3 (5)U1vi—O5—P2—C8152.2 (2)
C2—C3—C8—P290.4 (5)C3—C8—P2—O4172.1 (3)
C6—C5—C9—P388.1 (5)C3—C8—P2—O548.6 (3)
C4—C5—C9—P386.9 (5)C3—C8—P2—O667.8 (3)
O10—U1—O1—P134.8 (4)U2ii—O8—P3—O944.4 (9)
O10v—U1—O1—P1145.2 (4)U2ii—O8—P3—O7162.8 (8)
O5i—U1—O1—P1124.7 (4)U2ii—O8—P3—C980.3 (9)
O5iii—U1—O1—P155.3 (4)U2vii—O9—P3—O8102.3 (4)
O12—U2—O2—P135.5 (3)U2vii—O9—P3—O7137.0 (3)
O11—U2—O2—P1144.4 (3)U2vii—O9—P3—C921.5 (4)
O8ii—U2—O2—P1134.0 (3)C5—C9—P3—O864.9 (3)
O4iii—U2—O2—P154.7 (3)C5—C9—P3—O9167.4 (3)
O9iv—U2—O2—P150.9 (4)C5—C9—P3—O753.3 (3)
O1W—U2—O2—P1119.4 (3)
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y+1, z+1; (iv) x, y, z1; (v) x+1, y+1, z+1; (vi) x1, y, z; (vii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3Z···O6Wviii0.94 (1)1.69 (1)2.625 (4)168 (4)
O6—H6Z···O3Wiii0.94 (1)1.68 (1)2.609 (5)168 (4)
O7—H7Z···O4W0.94 (1)1.76 (1)2.696 (4)171 (5)
O1W—H1X···O6Wviii0.95 (1)1.80 (1)2.747 (4)173 (4)
O1W—H1Y···O4Wii0.95 (1)1.86 (2)2.752 (5)156 (5)
O2W—H2X···O7Wix0.95 (1)2.18 (6)3.002 (9)144 (8)
O2W—H2Y···O110.95 (1)2.15 (5)3.010 (8)150 (9)
O3W—H3X···O8W0.95 (1)1.85 (1)2.799 (7)175 (4)
O3W—H3Y···O100.95 (1)2.67 (4)3.336 (5)128 (4)
O3W—H3Y···O1v0.95 (1)2.59 (3)3.333 (5)136 (3)
O4W—H4X···O3vi0.95 (1)1.95 (2)2.841 (5)156 (4)
O4W—H4Y···O50.95 (1)2.12 (2)3.031 (4)161 (4)
O5W—H5X···O100.95 (1)2.07 (2)2.989 (5)163 (4)
O5W—H5Y···O7W0.95 (1)1.87 (1)2.823 (7)174 (3)
O6W—H6X···O5W0.94 (1)1.73 (2)2.645 (5)164 (3)
O6W—H6Y···O20.95 (1)1.93 (1)2.875 (4)175 (4)
O7W—H7X···O2W0.95 (1)1.81 (2)2.741 (10)163 (6)
O7W—H7Y···O9x0.95 (1)2.04 (2)2.972 (6)166 (6)
O8W—H8X···O7W0.95 (1)1.99 (3)2.927 (8)167 (9)
O8W—H8Y···O3Wxi0.96 (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) x1, y, z; (viii) x+1, y, z+1; (ix) x+1, y, z; (x) x+1, y, z1; (xi) x+1, y+1, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC3H11FNO14P3U2·4(H2O)C8H10O8P2UC9H14O13P3U1.50·7(H2O)
Mr945.16534.13906.27
Crystal system, space groupMonoclinic, C2/cMonoclinic, P21/cTriclinic, P1
Temperature (K)150296150
a, b, c (Å)25.8297 (10), 8.7560 (3), 17.7432 (7)10.9522 (13), 6.4691 (7), 9.2802 (10)8.7982 (3), 11.8876 (4), 12.6446 (4)
α, β, γ (°)90, 99.951 (2), 9090, 96.333 (9), 9095.219 (2), 106.752 (2), 96.980 (2)
V3)3952.5 (3)653.50 (13)1245.89 (7)
Z822
Radiation typeMo KαMo KαMo Kα
µ (mm1)16.7112.6910.03
Crystal size (mm)0.05 × 0.03 × 0.010.03 × 0.02 × 0.010.02 × 0.02 × 0.01
Data collection
DiffractometerBruker X8 Kappa CCD APEX-II
diffractometer
Bruker X8 Kappa CCD APEX-II
diffractometer
Bruker X8 Kappa CCD APEX-II
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2008)
Multi-scan
SADABS (Bruker, 2008)
Multi-scan
SADABS (Bruker, 2008)
Tmin, Tmax0.489, 0.9210.702, 0.9390.825, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections
76767, 5310, 4724 8989, 2475, 1556 54948, 4560, 4004
Rint0.0740.0550.064
(sin θ/λ)max1)0.6850.7690.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.059, 1.06 0.034, 0.060, 1.00 0.021, 0.041, 1.08
No. of reflections531024754560
No. of parameters25591380
No. of restraints5132
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0206P)2 + 49.9087P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0205P)2]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0095P)2 + 3.2581P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.52, 1.041.91, 2.740.63, 0.76

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009), SHELXTL (Bruker, 2008).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1Z···F1i0.945 (10)1.81 (3)2.705 (5)157 (5)
O3—H3Z···O6W0.956 (10)2.186 (17)3.139 (13)175 (6)
O3—H3Z···O7W0.956 (10)1.695 (18)2.643 (13)171 (5)
O8—H8Y···O4W0.949 (10)1.88 (4)2.802 (10)163 (13)
O8—H8Y···O5W0.949 (10)1.62 (3)2.560 (13)171 (14)
O8—H8X···O8W0.949 (10)1.902 (18)2.850 (11)176 (13)
O8—H8X···O9W0.949 (10)2.48 (3)3.415 (17)170 (12)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O2—H2Z···O4i0.834 (10)1.881 (15)2.703 (5)168 (5)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O3—H3Z···O6Wi0.944 (10)1.694 (14)2.625 (4)168 (4)
O6—H6Z···O3Wii0.944 (10)1.680 (14)2.609 (5)168 (4)
O7—H7Z···O4W0.943 (10)1.760 (13)2.696 (4)171 (5)
O1W—H1X···O6Wi0.948 (10)1.803 (13)2.747 (4)173 (4)
O1W—H1Y···O4Wiii0.945 (10)1.86 (2)2.752 (5)156 (5)
O2W—H2X···O7Wiv0.954 (10)2.18 (6)3.002 (9)144 (8)
O2W—H2Y···O110.951 (10)2.15 (5)3.010 (8)150 (9)
O3W—H3X···O8W0.952 (10)1.850 (14)2.799 (7)175 (4)
O3W—H3Y···O100.946 (10)2.67 (4)3.336 (5)128 (4)
O3W—H3Y···O1v0.946 (10)2.59 (3)3.333 (5)136 (3)
O4W—H4X···O3vi0.947 (10)1.95 (2)2.841 (5)156 (4)
O4W—H4Y···O50.948 (10)2.118 (19)3.031 (4)161 (4)
O5W—H5X···O100.949 (10)2.070 (17)2.989 (5)163 (4)
O5W—H5Y···O7W0.953 (10)1.874 (12)2.823 (7)174 (3)
O6W—H6X···O5W0.942 (10)1.725 (16)2.645 (5)164 (3)
O6W—H6Y···O20.945 (10)1.932 (12)2.875 (4)175 (4)
O7W—H7X···O2W0.953 (10)1.81 (2)2.741 (10)163 (6)
O7W—H7Y···O9vii0.951 (10)2.04 (2)2.972 (6)166 (6)
O8W—H8X···O7W0.954 (10)1.99 (3)2.927 (8)167 (9)
O8W—H8Y···O3Wviii0.955 (10)2.07 (5)2.901 (8)145 (7)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z+1; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y+1, z+1; (vi) x1, y, z; (vii) x+1, y, z1; (viii) x+1, y+1, z.
 

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