Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613034781/bi5030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613034781/bi5030Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613034781/bi5030IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613034781/bi5030IIIsup4.hkl |
CCDC references: 978938; 978939; 978940
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).
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) Å3 | 0.05 × 0.03 × 0.01 mm |
Z = 8 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H 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 parameters | Δρmax = 1.52 e Å−3 |
5 restraints | Δρmin = −1.04 e Å−3 |
C3H11FNO14P3U2·4(H2O) | V = 3952.5 (3) Å3 |
Mr = 945.16 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.8297 (10) Å | µ = 16.71 mm−1 |
b = 8.7560 (3) Å | T = 150 K |
c = 17.7432 (7) Å | 0.05 × 0.03 × 0.01 mm |
β = 99.951 (2)° |
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 = 0.921 | Rint = 0.074 |
76767 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 5 restraints |
wR(F2) = 0.059 | H 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 | Δρmax = 1.52 e Å−3 |
255 parameters | Δρmin = −1.04 e Å−3 |
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. |
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 |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—O9i | 2.354 (4) | C3—P3 | 1.808 (5) |
U1—O2ii | 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—O6iii | 2.311 (3) | O3—P1 | 1.511 (4) |
U2—F1iv | 2.336 (3) | O3—H3Z | 0.956 (10) |
U2—F1 | 2.351 (3) | O4—P2 | 1.507 (4) |
U2—O7i | 2.355 (4) | O5—P2 | 1.530 (3) |
U2—U2iv | 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—O9i | 93.82 (17) | N1—C2—H2B | 108.4 |
O11—U1—O9i | 86.23 (17) | P2—C2—H2B | 108.4 |
O4—U1—O9i | 73.50 (13) | H2A—C2—H2B | 107.5 |
O1—U1—O9i | 146.64 (13) | N1—C3—P3 | 114.7 (3) |
O10—U1—O2ii | 85.63 (17) | N1—C3—H3A | 108.6 |
O11—U1—O2ii | 92.70 (17) | P3—C3—H3A | 108.6 |
O4—U1—O2ii | 151.51 (14) | N1—C3—H3B | 108.6 |
O1—U1—O2ii | 78.94 (13) | P3—C3—H3B | 108.6 |
O9i—U1—O2ii | 133.83 (13) | H3A—C3—H3B | 107.6 |
O10—U1—O1W | 88.73 (18) | U2iv—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) |
O9i—U1—O1W | 65.24 (13) | C3—N1—H1Z | 105 (4) |
O2ii—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—U1ii | 132.6 (2) |
O13—U2—O6iii | 89.78 (15) | P1—O3—H3Z | 105.6 (10) |
O12—U2—O6iii | 91.04 (16) | P2—O4—U1 | 158.3 (3) |
O5—U2—O6iii | 79.54 (12) | P2—O5—U2 | 139.6 (2) |
O13—U2—F1iv | 90.48 (14) | P2—O6—U2v | 173.5 (2) |
O12—U2—F1iv | 88.57 (15) | P3—O7—U2vi | 153.5 (2) |
O5—U2—F1iv | 146.73 (11) | P3—O8—H8X | 108 (9) |
O6iii—U2—F1iv | 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—U1vi | 149.3 (2) |
O5—U2—F1 | 149.54 (11) | O1—P1—O3 | 113.6 (2) |
O6iii—U2—F1 | 70.11 (11) | O1—P1—O2 | 113.1 (2) |
F1iv—U2—F1 | 63.63 (11) | O3—P1—O2 | 112.1 (2) |
O13—U2—O7i | 90.02 (15) | O1—P1—C1 | 108.4 (2) |
O12—U2—O7i | 89.43 (16) | O3—P1—C1 | 107.0 (2) |
O5—U2—O7i | 76.57 (12) | O2—P1—C1 | 101.7 (2) |
O6iii—U2—O7i | 156.11 (12) | O6—P2—O4 | 112.6 (2) |
F1iv—U2—O7i | 70.17 (11) | O6—P2—O5 | 110.6 (2) |
F1—U2—O7i | 133.77 (11) | O4—P2—O5 | 112.9 (2) |
O13—U2—U2iv | 89.49 (12) | O6—P2—C2 | 107.7 (2) |
O12—U2—U2iv | 89.83 (12) | O4—P2—C2 | 109.0 (2) |
O5—U2—U2iv | 177.80 (9) | O5—P2—C2 | 103.5 (2) |
O6iii—U2—U2iv | 101.80 (9) | O7—P3—O9 | 117.1 (2) |
F1iv—U2—U2iv | 31.93 (7) | O7—P3—O8 | 108.7 (2) |
F1—U2—U2iv | 31.71 (7) | O9—P3—O8 | 111.5 (2) |
O7i—U2—U2iv | 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—U2iv | −91.20 (17) | O7i—U2—O5—P2 | 67.8 (3) |
O12—U2—F1—U2iv | 87.84 (18) | U1—O1—P1—O3 | 169.7 (4) |
O5—U2—F1—U2iv | −176.50 (18) | U1—O1—P1—O2 | 40.5 (5) |
O6iii—U2—F1—U2iv | 178.54 (18) | U1—O1—P1—C1 | −71.4 (5) |
F1iv—U2—F1—U2iv | −0.001 (2) | U1ii—O2—P1—O1 | 83.1 (4) |
O7i—U2—F1—U2iv | −2.5 (2) | U1ii—O2—P1—O3 | −46.9 (4) |
P3—C3—N1—C2 | 163.4 (3) | U1ii—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) |
O9i—U1—O1—P1 | 101.7 (5) | U2—O5—P2—C2 | 87.6 (4) |
O2ii—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) | U2vi—O7—P3—O9 | −18.8 (6) |
O1—U1—O4—P2 | 34.1 (6) | U2vi—O7—P3—O8 | −146.2 (4) |
O9i—U1—O4—P2 | −133.3 (7) | U2vi—O7—P3—C3 | 104.4 (5) |
O2ii—U1—O4—P2 | 61.2 (8) | U1vi—O9—P3—O7 | −45.2 (6) |
O1W—U1—O4—P2 | −147.2 (6) | U1vi—O9—P3—O8 | 80.9 (5) |
O13—U2—O5—P2 | 158.1 (3) | U1vi—O9—P3—C3 | −166.5 (5) |
O12—U2—O5—P2 | −21.2 (4) | N1—C3—P3—O7 | −43.0 (4) |
O6iii—U2—O5—P2 | −111.9 (3) | N1—C3—P3—O9 | 84.6 (4) |
F1iv—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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1Z···F1v | 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. |
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) Å3 | 0.03 × 0.02 × 0.01 mm |
Z = 2 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H 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 parameters | Δρmax = 1.91 e Å−3 |
1 restraint | Δρmin = −2.74 e Å−3 |
C8H10O8P2U | V = 653.50 (13) Å3 |
Mr = 534.13 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9522 (13) Å | µ = 12.69 mm−1 |
b = 6.4691 (7) Å | T = 296 K |
c = 9.2802 (10) Å | 0.03 × 0.02 × 0.01 mm |
β = 96.333 (9)° |
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 = 0.939 | Rint = 0.055 |
8989 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 1 restraint |
wR(F2) = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 1.91 e Å−3 |
2475 reflections | Δρmin = −2.74 e Å−3 |
91 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
U1—O4 | 1.781 (3) | O2—H2Z | 0.834 (10) |
U1—O4i | 1.781 (3) | C1—C2 | 1.518 (7) |
U1—O3ii | 2.269 (4) | C1—H1A | 0.9700 |
U1—O3iii | 2.269 (4) | C1—H1B | 0.9700 |
U1—O1 | 2.278 (3) | C2—C3 | 1.389 (7) |
U1—O1i | 2.278 (3) | C2—C4 | 1.390 (7) |
P1—O3 | 1.504 (4) | C3—C4v | 1.384 (7) |
P1—O1 | 1.507 (4) | C3—H3 | 0.9300 |
P1—O2 | 1.564 (4) | C4—C3v | 1.384 (7) |
P1—C1 | 1.776 (5) | C4—H4 | 0.9300 |
O3—U1iv | 2.269 (4) | ||
O4—U1—O4i | 179.999 (2) | P1—O1—U1 | 144.0 (2) |
O4—U1—O3ii | 90.25 (15) | P1—O2—H2Z | 111 (4) |
O4—U1—O3iii | 89.75 (15) | C2—C1—P1 | 115.9 (3) |
O3ii—U1—O3iii | 180.0 | C2—C1—H1A | 108.3 |
O4—U1—O1 | 89.93 (15) | P1—C1—H1A | 108.3 |
O3ii—U1—O1 | 88.95 (14) | C2—C1—H1B | 108.3 |
O3iii—U1—O1 | 91.05 (14) | P1—C1—H1B | 108.3 |
O4—U1—O1i | 90.07 (15) | H1A—C1—H1B | 107.4 |
O3ii—U1—O1i | 91.05 (14) | C3—C2—C4 | 118.0 (5) |
O3iii—U1—O1i | 88.95 (14) | C3—C2—C1 | 121.2 (5) |
O1—U1—O1i | 179.9990 (10) | C4—C2—C1 | 120.8 (5) |
O3—P1—O1 | 113.7 (2) | C4v—C3—C2 | 120.9 (6) |
O3—P1—O2 | 109.7 (2) | C4v—C3—H3 | 119.5 |
O1—P1—O2 | 109.5 (2) | C2—C3—H3 | 119.5 |
O3—P1—C1 | 109.3 (2) | C3v—C4—C2 | 121.1 (5) |
O1—P1—C1 | 109.7 (2) | C3v—C4—H4 | 119.5 |
O2—P1—C1 | 104.4 (2) | C2—C4—H4 | 119.5 |
P1—O3—U1iv | 153.6 (2) | ||
O1—P1—O3—U1iv | −9.1 (6) | O3—P1—C1—C2 | 177.5 (4) |
O2—P1—O3—U1iv | −132.2 (5) | O1—P1—C1—C2 | −57.2 (5) |
C1—P1—O3—U1iv | 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—C4v | −0.4 (8) |
O4—U1—O1—P1 | −149.5 (4) | C1—C2—C3—C4v | 179.2 (5) |
O4i—U1—O1—P1 | 30.5 (4) | C3—C2—C4—C3v | 0.4 (8) |
O3ii—U1—O1—P1 | −59.3 (4) | C1—C2—C4—C3v | −179.2 (5) |
O3iii—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. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2Z···O4vi | 0.83 (1) | 1.88 (2) | 2.703 (5) | 168 (5) |
Symmetry code: (vi) x, y+1, z. |
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) Å3 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.021 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.041 | H 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 parameters | Δρmax = 0.63 e Å−3 |
32 restraints | Δρmin = −0.76 e Å−3 |
C9H14O13P3U1.50·7(H2O) | γ = 96.980 (2)° |
Mr = 906.27 | V = 1245.89 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.7982 (3) Å | Mo Kα radiation |
b = 11.8876 (4) Å | µ = 10.03 mm−1 |
c = 12.6446 (4) Å | T = 150 K |
α = 95.219 (2)° | 0.02 × 0.02 × 0.01 mm |
β = 106.752 (2)° |
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 = 0.906 | Rint = 0.064 |
54948 measured reflections |
R[F2 > 2σ(F2)] = 0.021 | 32 restraints |
wR(F2) = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.63 e Å−3 |
4560 reflections | Δρmin = −0.76 e Å−3 |
380 parameters |
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. |
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 |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
U1—O10 | 1.774 (3) | C9—H9B | 0.9900 |
U1—O1 | 2.294 (3) | O1—P1 | 1.517 (3) |
U1—O5i | 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—O8ii | 2.316 (3) | O4—P2 | 1.500 (3) |
U2—O4iii | 2.324 (3) | O5—P2 | 1.533 (3) |
U2—O9iv | 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—O10v | 179.9990 (10) | C1—C7—H7A | 109.2 |
O10—U1—O1 | 91.00 (12) | P1—C7—H7A | 109.2 |
O10v—U1—O1 | 89.01 (12) | C1—C7—H7B | 109.2 |
O10—U1—O1v | 89.00 (12) | P1—C7—H7B | 109.2 |
O10v—U1—O1v | 90.99 (12) | H7A—C7—H7B | 107.9 |
O1—U1—O1v | 180.00 (8) | C3—C8—P2 | 114.4 (3) |
O10—U1—O5i | 89.89 (12) | C3—C8—H8A | 108.7 |
O10v—U1—O5i | 90.11 (12) | P2—C8—H8A | 108.7 |
O1—U1—O5i | 88.08 (11) | C3—C8—H8B | 108.7 |
O1v—U1—O5i | 91.92 (11) | P2—C8—H8B | 108.7 |
O10—U1—O5iii | 90.11 (12) | H8A—C8—H8B | 107.6 |
O10v—U1—O5iii | 89.89 (12) | C5—C9—P3 | 109.7 (3) |
O1—U1—O5iii | 91.92 (11) | C5—C9—H9A | 109.7 |
O1v—U1—O5iii | 88.08 (11) | P3—C9—H9A | 109.7 |
O5i—U1—O5iii | 180.0000 (10) | C5—C9—H9B | 109.7 |
O12—U2—O11 | 179.23 (14) | P3—C9—H9B | 109.7 |
O12—U2—O8ii | 94.99 (13) | H9A—C9—H9B | 108.2 |
O11—U2—O8ii | 85.65 (13) | P1—O1—U1 | 149.04 (18) |
O12—U2—O4iii | 90.71 (13) | P1—O2—U2 | 141.33 (18) |
O11—U2—O4iii | 88.91 (13) | P1—O3—H3Z | 113 (3) |
O8ii—U2—O4iii | 153.07 (10) | P2—O4—U2iii | 162.3 (2) |
O12—U2—O9iv | 86.61 (12) | P2—O5—U1vi | 133.58 (17) |
O11—U2—O9iv | 93.96 (12) | P2—O6—H6Z | 116 (3) |
O8ii—U2—O9iv | 76.92 (10) | P3—O7—H7Z | 115 (3) |
O4iii—U2—O9iv | 77.17 (10) | P3—O8—U2ii | 165.0 (2) |
O12—U2—O2 | 91.82 (12) | P3—O9—U2vii | 147.9 (2) |
O11—U2—O2 | 87.43 (12) | U2—O1W—H1X | 124 (2) |
O8ii—U2—O2 | 132.79 (10) | U2—O1W—H1Y | 126 (2) |
O4iii—U2—O2 | 73.10 (10) | H1X—O1W—H1Y | 109.8 (16) |
O9iv—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) |
O8ii—U2—O1W | 68.03 (10) | O2—P1—C7 | 110.48 (19) |
O4iii—U2—O1W | 138.80 (11) | O1—P1—C7 | 108.69 (19) |
O9iv—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) | U2iii—O4—P2—O5 | 178.5 (6) |
C2—C1—C6—C5 | −1.0 (7) | U2iii—O4—P2—O6 | 55.3 (7) |
C7—C1—C6—C5 | 177.9 (4) | U2iii—O4—P2—C8 | −59.9 (7) |
C2—C1—C7—P1 | 95.9 (4) | U1vi—O5—P2—O4 | −31.0 (3) |
C6—C1—C7—P1 | −82.9 (5) | U1vi—O5—P2—O6 | 94.1 (2) |
C4—C3—C8—P2 | −88.3 (5) | U1vi—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) | U2ii—O8—P3—O9 | −44.4 (9) |
O10v—U1—O1—P1 | 145.2 (4) | U2ii—O8—P3—O7 | −162.8 (8) |
O5i—U1—O1—P1 | −124.7 (4) | U2ii—O8—P3—C9 | 80.3 (9) |
O5iii—U1—O1—P1 | 55.3 (4) | U2vii—O9—P3—O8 | 102.3 (4) |
O12—U2—O2—P1 | −35.5 (3) | U2vii—O9—P3—O7 | −137.0 (3) |
O11—U2—O2—P1 | 144.4 (3) | U2vii—O9—P3—C9 | −21.5 (4) |
O8ii—U2—O2—P1 | −134.0 (3) | C5—C9—P3—O8 | 64.9 (3) |
O4iii—U2—O2—P1 | 54.7 (3) | C5—C9—P3—O9 | −167.4 (3) |
O9iv—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. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3Z···O6Wviii | 0.94 (1) | 1.69 (1) | 2.625 (4) | 168 (4) |
O6—H6Z···O3Wiii | 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···O6Wviii | 0.95 (1) | 1.80 (1) | 2.747 (4) | 173 (4) |
O1W—H1Y···O4Wii | 0.95 (1) | 1.86 (2) | 2.752 (5) | 156 (5) |
O2W—H2X···O7Wix | 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···O1v | 0.95 (1) | 2.59 (3) | 3.333 (5) | 136 (3) |
O4W—H4X···O3vi | 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···O9x | 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···O3Wxi | 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. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C3H11FNO14P3U2·4(H2O) | C8H10O8P2U | C9H14O13P3U1.50·7(H2O) |
Mr | 945.16 | 534.13 | 906.27 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 150 | 296 | 150 |
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), 90 | 90, 96.333 (9), 90 | 95.219 (2), 106.752 (2), 96.980 (2) |
V (Å3) | 3952.5 (3) | 653.50 (13) | 1245.89 (7) |
Z | 8 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 16.71 | 12.69 | 10.03 |
Crystal size (mm) | 0.05 × 0.03 × 0.01 | 0.03 × 0.02 × 0.01 | 0.02 × 0.02 × 0.01 |
Data collection | |||
Diffractometer | Bruker X8 Kappa CCD APEX-II diffractometer | Bruker X8 Kappa CCD APEX-II diffractometer | Bruker X8 Kappa CCD APEX-II diffractometer |
Absorption correction | Multi-scan SADABS (Bruker, 2008) | Multi-scan SADABS (Bruker, 2008) | Multi-scan SADABS (Bruker, 2008) |
Tmin, Tmax | 0.489, 0.921 | 0.702, 0.939 | 0.825, 0.906 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 76767, 5310, 4724 | 8989, 2475, 1556 | 54948, 4560, 4004 |
Rint | 0.074 | 0.055 | 0.064 |
(sin θ/λ)max (Å−1) | 0.685 | 0.769 | 0.602 |
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 reflections | 5310 | 2475 | 4560 |
No. of parameters | 255 | 91 | 380 |
No. of restraints | 5 | 1 | 32 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H 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 Å−3) | 1.52, −1.04 | 1.91, −2.74 | 0.63, −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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1Z···F1i | 0.945 (10) | 1.81 (3) | 2.705 (5) | 157 (5) |
O3—H3Z···O6W | 0.956 (10) | 2.186 (17) | 3.139 (13) | 175 (6) |
O3—H3Z···O7W | 0.956 (10) | 1.695 (18) | 2.643 (13) | 171 (5) |
O8—H8Y···O4W | 0.949 (10) | 1.88 (4) | 2.802 (10) | 163 (13) |
O8—H8Y···O5W | 0.949 (10) | 1.62 (3) | 2.560 (13) | 171 (14) |
O8—H8X···O8W | 0.949 (10) | 1.902 (18) | 2.850 (11) | 176 (13) |
O8—H8X···O9W | 0.949 (10) | 2.48 (3) | 3.415 (17) | 170 (12) |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2Z···O4i | 0.834 (10) | 1.881 (15) | 2.703 (5) | 168 (5) |
Symmetry code: (i) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3Z···O6Wi | 0.944 (10) | 1.694 (14) | 2.625 (4) | 168 (4) |
O6—H6Z···O3Wii | 0.944 (10) | 1.680 (14) | 2.609 (5) | 168 (4) |
O7—H7Z···O4W | 0.943 (10) | 1.760 (13) | 2.696 (4) | 171 (5) |
O1W—H1X···O6Wi | 0.948 (10) | 1.803 (13) | 2.747 (4) | 173 (4) |
O1W—H1Y···O4Wiii | 0.945 (10) | 1.86 (2) | 2.752 (5) | 156 (5) |
O2W—H2X···O7Wiv | 0.954 (10) | 2.18 (6) | 3.002 (9) | 144 (8) |
O2W—H2Y···O11 | 0.951 (10) | 2.15 (5) | 3.010 (8) | 150 (9) |
O3W—H3X···O8W | 0.952 (10) | 1.850 (14) | 2.799 (7) | 175 (4) |
O3W—H3Y···O10 | 0.946 (10) | 2.67 (4) | 3.336 (5) | 128 (4) |
O3W—H3Y···O1v | 0.946 (10) | 2.59 (3) | 3.333 (5) | 136 (3) |
O4W—H4X···O3vi | 0.947 (10) | 1.95 (2) | 2.841 (5) | 156 (4) |
O4W—H4Y···O5 | 0.948 (10) | 2.118 (19) | 3.031 (4) | 161 (4) |
O5W—H5X···O10 | 0.949 (10) | 2.070 (17) | 2.989 (5) | 163 (4) |
O5W—H5Y···O7W | 0.953 (10) | 1.874 (12) | 2.823 (7) | 174 (3) |
O6W—H6X···O5W | 0.942 (10) | 1.725 (16) | 2.645 (5) | 164 (3) |
O6W—H6Y···O2 | 0.945 (10) | 1.932 (12) | 2.875 (4) | 175 (4) |
O7W—H7X···O2W | 0.953 (10) | 1.81 (2) | 2.741 (10) | 163 (6) |
O7W—H7Y···O9vii | 0.951 (10) | 2.04 (2) | 2.972 (6) | 166 (6) |
O8W—H8X···O7W | 0.954 (10) | 1.99 (3) | 2.927 (8) | 167 (9) |
O8W—H8Y···O3Wviii | 0.955 (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) x−1, y, z; (vii) x+1, y, z−1; (viii) −x+1, −y+1, −z. |