Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619001839/ku3235sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32351asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32351bsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32352asup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32352bsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32353asup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32353bsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001839/ku32353csup8.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619001839/ku3235sup9.pdf | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32351asup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32351bsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32352asup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32352bsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32353asup14.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32353bsup15.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619001839/ku32353csup16.cml |
CCDC references: 1845720; 1845721; 1845722; 1845723; 1845724; 1845725; 1845726
For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 2012), PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: PLATON (Spek, 2009).
C22H23O4P | Dx = 1.318 Mg m−3 |
Mr = 382.37 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 4004 reflections |
a = 16.7332 (8) Å | θ = 4.5–27.9° |
b = 8.2012 (3) Å | µ = 0.17 mm−1 |
c = 28.0902 (13) Å | T = 173 K |
V = 3854.9 (3) Å3 | Block, colorless |
Z = 8 | 0.37 × 0.15 × 0.05 mm |
F(000) = 1616 |
Agilent Xcalibur Sapphire3 diffractometer | 4758 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3133 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.070 |
ω scans | θmax = 28.3°, θmin = 4.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −22→21 |
Tmin = 0.980, Tmax = 1.000 | k = −10→10 |
29616 measured reflections | l = −36→37 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0669P)2 + 1.3244P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4758 reflections | Δρmax = 0.45 e Å−3 |
265 parameters | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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. An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.86630 (3) | 0.11650 (7) | 0.74859 (2) | 0.02500 (16) | |
O1 | 0.88249 (10) | 0.28792 (18) | 0.76026 (6) | 0.0334 (4) | |
O2 | 0.83579 (9) | 0.00874 (17) | 0.79113 (5) | 0.0314 (4) | |
O3 | 0.79822 (9) | 0.09657 (16) | 0.71029 (5) | 0.0288 (4) | |
C5 | 1.02433 (14) | 0.1749 (3) | 0.58777 (8) | 0.0340 (5) | |
O4 | 1.01055 (11) | 0.0164 (2) | 0.76139 (6) | 0.0395 (4) | |
C10 | 0.71903 (14) | 0.1766 (3) | 0.64312 (9) | 0.0332 (5) | |
C3 | 1.03925 (14) | 0.1711 (3) | 0.67304 (9) | 0.0335 (5) | |
H3 | 1.0670 (8) | 0.2088 (10) | 0.7011 (8) | 0.040* | |
C11 | 0.73182 (17) | 0.1995 (3) | 0.59491 (10) | 0.0421 (6) | |
H11 | 0.7791 (15) | 0.2462 (15) | 0.5842 (4) | 0.051* | |
C1 | 0.95057 (13) | −0.0002 (3) | 0.72631 (8) | 0.0285 (5) | |
H1 | 0.9350 | −0.1175 | 0.7237 | 0.034* | |
C18 | 0.87025 (14) | 0.1879 (3) | 0.87877 (9) | 0.0363 (5) | |
H18 | 0.9039 (10) | 0.2212 (10) | 0.8520 (8) | 0.044* | |
C2 | 0.97640 (13) | 0.0618 (2) | 0.67771 (8) | 0.0272 (5) | |
C7 | 0.93737 (14) | 0.0092 (3) | 0.63681 (8) | 0.0303 (5) | |
H7 | 0.8948 (12) | −0.065 (2) | 0.63923 (10) | 0.036* | |
C4 | 1.06260 (15) | 0.2263 (3) | 0.62880 (9) | 0.0369 (6) | |
H4 | 1.1080 (12) | 0.305 (2) | 0.62631 (11) | 0.044* | |
C17 | 0.79922 (14) | 0.1056 (3) | 0.87028 (8) | 0.0308 (5) | |
C19 | 0.89383 (17) | 0.2232 (3) | 0.92481 (9) | 0.0398 (6) | |
H19 | 0.9437 (15) | 0.2807 (17) | 0.93039 (19) | 0.048* | |
C6 | 0.96076 (14) | 0.0661 (3) | 0.59253 (8) | 0.0339 (5) | |
H6 | 0.9318 (8) | 0.0289 (10) | 0.5637 (8) | 0.041* | |
C22 | 0.75307 (15) | 0.0584 (3) | 0.90880 (9) | 0.0366 (6) | |
H22 | 0.7036 (14) | −0.0020 (17) | 0.90344 (18) | 0.044* | |
C16 | 0.77049 (14) | 0.0704 (3) | 0.82078 (8) | 0.0334 (5) | |
H16A | 0.7267 (8) | −0.0121 (14) | 0.82201 (8) | 0.040* | |
H16B | 0.7485 (4) | 0.1722 (18) | 0.8064 (3) | 0.040* | |
C15 | 0.64759 (15) | 0.1085 (3) | 0.65822 (10) | 0.0381 (6) | |
H15 | 0.6377 (3) | 0.0941 (5) | 0.6925 (10) | 0.046* | |
C21 | 0.77629 (16) | 0.0958 (3) | 0.95484 (9) | 0.0439 (6) | |
H21 | 0.7423 (10) | 0.0644 (10) | 0.9818 (8) | 0.053* | |
C20 | 0.84685 (17) | 0.1770 (3) | 0.96282 (10) | 0.0439 (6) | |
H20 | 0.8624 (6) | 0.2000 (8) | 0.9928 (10) | 0.053* | |
C13 | 0.6045 (2) | 0.0829 (3) | 0.57840 (12) | 0.0545 (8) | |
H13 | 0.5656 (14) | 0.0496 (12) | 0.5561 (8) | 0.065* | |
C12 | 0.6739 (2) | 0.1524 (4) | 0.56281 (11) | 0.0543 (8) | |
H12 | 0.6819 (4) | 0.1678 (7) | 0.5310 (12) | 0.065* | |
C14 | 0.59054 (18) | 0.0609 (3) | 0.62603 (11) | 0.0496 (7) | |
H14 | 0.5416 (16) | 0.0130 (16) | 0.6367 (4) | 0.060* | |
C8 | 1.05096 (18) | 0.2326 (3) | 0.53963 (10) | 0.0510 (7) | |
H8A | 1.0775 (11) | 0.332 (2) | 0.54271 (13) | 0.076* | |
H8B | 1.0066 (8) | 0.246 (2) | 0.5200 (4) | 0.076* | |
H8C | 1.0853 (11) | 0.1559 (17) | 0.5263 (4) | 0.076* | |
C9 | 0.78111 (16) | 0.2317 (3) | 0.67775 (9) | 0.0365 (6) | |
H9A | 0.8320 (9) | 0.2650 (7) | 0.6600 (3) | 0.044* | |
H9B | 0.7608 (4) | 0.3304 (18) | 0.6965 (3) | 0.044* | |
H40 | 1.0494 (17) | −0.069 (3) | 0.7537 (9) | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0241 (3) | 0.0235 (3) | 0.0274 (3) | 0.0000 (2) | −0.0007 (2) | −0.0014 (2) |
O1 | 0.0343 (10) | 0.0261 (8) | 0.0398 (10) | −0.0042 (6) | −0.0002 (7) | −0.0049 (6) |
O2 | 0.0307 (9) | 0.0317 (8) | 0.0318 (9) | 0.0046 (7) | 0.0043 (7) | 0.0026 (6) |
O3 | 0.0263 (8) | 0.0233 (7) | 0.0368 (9) | −0.0008 (6) | −0.0052 (6) | 0.0032 (6) |
C5 | 0.0316 (13) | 0.0319 (12) | 0.0385 (14) | 0.0058 (10) | 0.0097 (10) | 0.0033 (10) |
O4 | 0.0338 (10) | 0.0462 (10) | 0.0385 (10) | 0.0099 (8) | −0.0069 (7) | −0.0040 (7) |
C10 | 0.0333 (14) | 0.0245 (11) | 0.0417 (14) | 0.0078 (9) | −0.0096 (10) | 0.0001 (9) |
C3 | 0.0285 (13) | 0.0348 (12) | 0.0371 (13) | −0.0001 (9) | −0.0003 (10) | −0.0092 (10) |
C11 | 0.0348 (15) | 0.0412 (14) | 0.0503 (17) | 0.0066 (11) | 0.0032 (12) | 0.0078 (11) |
C1 | 0.0293 (12) | 0.0288 (11) | 0.0274 (12) | 0.0041 (9) | −0.0030 (9) | −0.0032 (8) |
C18 | 0.0315 (14) | 0.0395 (13) | 0.0379 (14) | 0.0007 (10) | 0.0035 (10) | 0.0022 (10) |
C2 | 0.0273 (12) | 0.0253 (10) | 0.0291 (12) | 0.0046 (9) | 0.0008 (9) | −0.0027 (8) |
C7 | 0.0295 (13) | 0.0295 (11) | 0.0320 (12) | −0.0046 (9) | 0.0000 (9) | −0.0016 (9) |
C4 | 0.0314 (14) | 0.0321 (12) | 0.0472 (15) | −0.0043 (10) | 0.0073 (11) | −0.0036 (10) |
C17 | 0.0264 (12) | 0.0300 (11) | 0.0359 (13) | 0.0063 (9) | 0.0029 (9) | 0.0002 (9) |
C19 | 0.0376 (15) | 0.0400 (14) | 0.0417 (15) | 0.0007 (11) | −0.0044 (11) | 0.0001 (11) |
C6 | 0.0356 (14) | 0.0360 (12) | 0.0302 (13) | 0.0009 (10) | −0.0026 (10) | −0.0040 (9) |
C22 | 0.0312 (14) | 0.0390 (13) | 0.0395 (15) | 0.0023 (10) | 0.0060 (10) | 0.0030 (10) |
C16 | 0.0274 (13) | 0.0374 (12) | 0.0355 (13) | 0.0003 (10) | 0.0059 (9) | 0.0000 (10) |
C15 | 0.0391 (15) | 0.0325 (13) | 0.0428 (15) | 0.0028 (10) | 0.0006 (11) | 0.0084 (10) |
C21 | 0.0387 (15) | 0.0571 (17) | 0.0358 (14) | 0.0085 (12) | 0.0103 (11) | 0.0075 (11) |
C20 | 0.0468 (17) | 0.0520 (15) | 0.0331 (14) | 0.0113 (13) | −0.0048 (12) | −0.0001 (11) |
C13 | 0.0544 (19) | 0.0442 (16) | 0.065 (2) | 0.0061 (14) | −0.0302 (16) | −0.0060 (14) |
C12 | 0.069 (2) | 0.0599 (18) | 0.0341 (15) | 0.0163 (16) | −0.0069 (14) | 0.0032 (12) |
C14 | 0.0355 (16) | 0.0376 (14) | 0.076 (2) | −0.0033 (11) | −0.0111 (14) | 0.0075 (13) |
C8 | 0.0470 (17) | 0.0616 (18) | 0.0443 (17) | 0.0012 (14) | 0.0132 (13) | 0.0092 (13) |
C9 | 0.0404 (15) | 0.0244 (11) | 0.0447 (14) | 0.0007 (10) | −0.0088 (11) | 0.0073 (10) |
P1—O1 | 1.4687 (16) | C7—H7 | 0.94 (3) |
P1—O2 | 1.5716 (16) | C4—H4 | 1.00 (3) |
P1—O3 | 1.5754 (15) | C17—C22 | 1.385 (3) |
P1—C1 | 1.815 (2) | C17—C16 | 1.499 (3) |
O2—C16 | 1.464 (3) | C19—C20 | 1.379 (4) |
O3—C9 | 1.465 (3) | C19—H19 | 0.97 (3) |
C5—C4 | 1.384 (3) | C6—H6 | 0.99 (3) |
C5—C6 | 1.395 (3) | C22—C21 | 1.385 (4) |
C5—C8 | 1.501 (3) | C22—H22 | 0.98 (3) |
O4—C1 | 1.413 (3) | C16—H16A | 0.998 (17) |
O4—H40 | 0.98 (3) | C16—H16B | 0.998 (17) |
C10—C11 | 1.384 (4) | C15—C14 | 1.372 (4) |
C10—C15 | 1.386 (3) | C15—H15 | 0.98 (3) |
C10—C9 | 1.493 (3) | C21—C20 | 1.374 (4) |
C3—C4 | 1.379 (3) | C21—H21 | 0.98 (3) |
C3—C2 | 1.388 (3) | C20—H20 | 0.90 (3) |
C3—H3 | 0.97 (3) | C13—C12 | 1.365 (4) |
C11—C12 | 1.379 (4) | C13—C14 | 1.370 (4) |
C11—H11 | 0.93 (3) | C13—H13 | 0.94 (3) |
C1—C2 | 1.520 (3) | C12—H12 | 0.91 (3) |
C1—H1 | 1.0000 | C14—H14 | 0.96 (3) |
C18—C19 | 1.383 (4) | C8—H8A | 0.930 (16) |
C18—C17 | 1.388 (3) | C8—H8B | 0.930 (15) |
C18—H18 | 0.98 (3) | C8—H8C | 0.930 (15) |
C2—C7 | 1.390 (3) | C9—H9A | 1.024 (18) |
C7—C6 | 1.385 (3) | C9—H9B | 1.024 (18) |
O1—P1—O2 | 115.37 (9) | C18—C19—H19 | 119.9 |
O1—P1—O3 | 112.66 (9) | C7—C6—C5 | 121.1 (2) |
O2—P1—O3 | 103.06 (8) | C7—C6—H6 | 119.4 |
O1—P1—C1 | 115.99 (10) | C5—C6—H6 | 119.4 |
O2—P1—C1 | 102.59 (9) | C17—C22—C21 | 120.8 (2) |
O3—P1—C1 | 105.77 (9) | C17—C22—H22 | 119.6 |
C16—O2—P1 | 118.73 (13) | C21—C22—H22 | 119.6 |
C9—O3—P1 | 119.27 (13) | O2—C16—C17 | 110.78 (19) |
C4—C5—C6 | 117.9 (2) | O2—C16—H16A | 109.5 |
C4—C5—C8 | 121.1 (2) | C17—C16—H16A | 109.5 |
C6—C5—C8 | 121.0 (2) | O2—C16—H16B | 109.5 |
C1—O4—H40 | 104.4 (15) | C17—C16—H16B | 109.5 |
C11—C10—C15 | 119.2 (2) | H16A—C16—H16B | 108.1 |
C11—C10—C9 | 119.3 (2) | C14—C15—C10 | 120.9 (3) |
C15—C10—C9 | 121.5 (2) | C14—C15—H15 | 119.6 |
C4—C3—C2 | 120.8 (2) | C10—C15—H15 | 119.6 |
C4—C3—H3 | 119.6 | C20—C21—C22 | 120.0 (2) |
C2—C3—H3 | 119.6 | C20—C21—H21 | 120.0 |
C12—C11—C10 | 119.6 (3) | C22—C21—H21 | 120.0 |
C12—C11—H11 | 120.2 | C21—C20—C19 | 119.8 (3) |
C10—C11—H11 | 120.2 | C21—C20—H20 | 120.1 |
O4—C1—C2 | 113.10 (19) | C19—C20—H20 | 120.1 |
O4—C1—P1 | 105.11 (14) | C12—C13—C14 | 120.9 (3) |
C2—C1—P1 | 110.74 (14) | C12—C13—H13 | 119.6 |
O4—C1—H1 | 109.3 | C14—C13—H13 | 119.6 |
C2—C1—H1 | 109.3 | C13—C12—C11 | 120.3 (3) |
P1—C1—H1 | 109.3 | C13—C12—H12 | 119.8 |
C19—C18—C17 | 120.5 (2) | C11—C12—H12 | 119.8 |
C19—C18—H18 | 119.8 | C13—C14—C15 | 119.2 (3) |
C17—C18—H18 | 119.8 | C13—C14—H14 | 120.4 |
C3—C2—C7 | 118.6 (2) | C15—C14—H14 | 120.4 |
C3—C2—C1 | 121.1 (2) | C5—C8—H8A | 109.5 |
C7—C2—C1 | 120.3 (2) | C5—C8—H8B | 109.5 |
C6—C7—C2 | 120.3 (2) | H8A—C8—H8B | 109.5 |
C6—C7—H7 | 119.8 | C5—C8—H8C | 109.5 |
C2—C7—H7 | 119.8 | H8A—C8—H8C | 109.5 |
C3—C4—C5 | 121.2 (2) | H8B—C8—H8C | 109.5 |
C3—C4—H4 | 119.4 | O3—C9—C10 | 108.29 (18) |
C5—C4—H4 | 119.4 | O3—C9—H9A | 110.0 |
C22—C17—C18 | 118.6 (2) | C10—C9—H9A | 110.0 |
C22—C17—C16 | 119.5 (2) | O3—C9—H9B | 110.0 |
C18—C17—C16 | 121.9 (2) | C10—C9—H9B | 110.0 |
C20—C19—C18 | 120.3 (3) | H9A—C9—H9B | 108.4 |
C20—C19—H19 | 119.9 | ||
O1—P1—O2—C16 | 48.40 (18) | C8—C5—C4—C3 | −178.7 (2) |
O3—P1—O2—C16 | −74.80 (17) | C19—C18—C17—C22 | −0.6 (3) |
C1—P1—O2—C16 | 175.47 (16) | C19—C18—C17—C16 | 177.9 (2) |
O1—P1—O3—C9 | 23.70 (19) | C17—C18—C19—C20 | −0.1 (4) |
O2—P1—O3—C9 | 148.69 (16) | C2—C7—C6—C5 | 1.0 (3) |
C1—P1—O3—C9 | −103.97 (17) | C4—C5—C6—C7 | −1.0 (3) |
C15—C10—C11—C12 | −0.8 (4) | C8—C5—C6—C7 | 178.3 (2) |
C9—C10—C11—C12 | −178.4 (2) | C18—C17—C22—C21 | 1.5 (3) |
O1—P1—C1—O4 | 55.39 (17) | C16—C17—C22—C21 | −177.0 (2) |
O2—P1—C1—O4 | −71.29 (16) | P1—O2—C16—C17 | −113.16 (18) |
O3—P1—C1—O4 | −178.96 (13) | C22—C17—C16—O2 | −136.4 (2) |
O1—P1—C1—C2 | −67.08 (17) | C18—C17—C16—O2 | 45.1 (3) |
O2—P1—C1—C2 | 166.25 (15) | C11—C10—C15—C14 | 1.3 (4) |
O3—P1—C1—C2 | 58.57 (17) | C9—C10—C15—C14 | 178.9 (2) |
C4—C3—C2—C7 | 0.0 (3) | C17—C22—C21—C20 | −1.7 (4) |
C4—C3—C2—C1 | 179.7 (2) | C22—C21—C20—C19 | 1.0 (4) |
O4—C1—C2—C3 | −20.6 (3) | C18—C19—C20—C21 | −0.1 (4) |
P1—C1—C2—C3 | 97.0 (2) | C14—C13—C12—C11 | 1.0 (4) |
O4—C1—C2—C7 | 159.11 (19) | C10—C11—C12—C13 | −0.4 (4) |
P1—C1—C2—C7 | −83.2 (2) | C12—C13—C14—C15 | −0.5 (4) |
C3—C2—C7—C6 | −0.4 (3) | C10—C15—C14—C13 | −0.7 (4) |
C1—C2—C7—C6 | 179.8 (2) | P1—O3—C9—C10 | 175.76 (15) |
C2—C3—C4—C5 | 0.0 (4) | C11—C10—C9—O3 | −129.7 (2) |
C6—C5—C4—C3 | 0.5 (3) | C15—C10—C9—O3 | 52.6 (3) |
C21H20ClO4P | F(000) = 420 |
Mr = 402.79 | Dx = 1.393 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4239 (8) Å | Cell parameters from 2191 reflections |
b = 7.8757 (5) Å | θ = 4.4–25.4° |
c = 12.0461 (7) Å | µ = 0.31 mm−1 |
β = 103.775 (7)° | T = 133 K |
V = 960.49 (11) Å3 | Block, colorless |
Z = 2 | 0.30 × 0.22 × 0.20 mm |
Agilent Xcalibur Sapphire3 diffractometer | 3407 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2955 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.028 |
ω scans | θmax = 26.4°, θmin = 4.3° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −9→13 |
Tmin = 0.991, Tmax = 1.000 | k = −8→9 |
6934 measured reflections | l = −15→15 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2038P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.34 e Å−3 |
3407 reflections | Δρmin = −0.20 e Å−3 |
255 parameters | Absolute structure: Refined as an inversion twin |
1 restraint | Absolute structure parameter: 0.35 (12) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.39196 (10) | 0.20951 (14) | 0.13606 (8) | 0.0314 (3) | |
Cl1 | 0.87251 (14) | 0.3666 (2) | 0.47865 (10) | 0.0640 (4) | |
O2 | 0.4032 (3) | 0.2610 (4) | 0.2646 (2) | 0.0368 (7) | |
O4 | 0.5090 (3) | 0.2690 (5) | −0.0254 (2) | 0.0483 (9) | |
H4 | 0.5506 | 0.3370 | −0.0576 | 0.072* | |
O1 | 0.3842 (3) | 0.0246 (4) | 0.1175 (2) | 0.0404 (7) | |
O3 | 0.2705 (3) | 0.3148 (4) | 0.0693 (3) | 0.0458 (8) | |
C2 | 0.6585 (4) | 0.2610 (5) | 0.1657 (3) | 0.0315 (9) | |
C3 | 0.7023 (4) | 0.3308 (6) | 0.2740 (4) | 0.0357 (9) | |
H3 | 0.652 (3) | 0.410 (5) | 0.2999 (15) | 0.043* | |
C9 | 0.4049 (4) | 0.2024 (6) | 0.4615 (3) | 0.0366 (9) | |
C4 | 0.8229 (4) | 0.2798 (7) | 0.3431 (4) | 0.0405 (10) | |
C5 | 0.9030 (5) | 0.1650 (6) | 0.3042 (4) | 0.0444 (12) | |
H5 | 0.986 (5) | 0.1341 (18) | 0.350 (3) | 0.053* | |
C14 | 0.2867 (4) | 0.2884 (7) | 0.4557 (4) | 0.0464 (11) | |
H14 | 0.2292 | 0.3133 | 0.3837 | 0.056* | |
C21 | −0.0793 (4) | 0.2817 (6) | −0.0668 (4) | 0.0407 (10) | |
H21 | −0.1135 (18) | 0.337 (3) | −0.011 (3) | 0.049* | |
C20 | −0.1603 (5) | 0.2497 (7) | −0.1726 (4) | 0.0483 (12) | |
H20 | −0.245 (5) | 0.2777 (18) | −0.1868 (9) | 0.058* | |
C13 | 0.2537 (5) | 0.3374 (7) | 0.5567 (5) | 0.0565 (14) | |
H13 | 0.1733 | 0.3965 | 0.5528 | 0.068* | |
C10 | 0.4860 (5) | 0.1684 (6) | 0.5690 (4) | 0.0409 (11) | |
H10 | 0.5671 | 0.1100 | 0.5752 | 0.049* | |
C17 | 0.1022 (5) | 0.1597 (6) | −0.1257 (4) | 0.0397 (11) | |
H17 | 0.192 (5) | 0.1288 (17) | −0.1098 (9) | 0.048* | |
C1 | 0.5270 (4) | 0.3155 (6) | 0.0922 (3) | 0.0363 (10) | |
H1 | 0.5172 | 0.4412 | 0.0983 | 0.044* | |
C16 | 0.0516 (4) | 0.2340 (6) | −0.0423 (3) | 0.0364 (10) | |
C11 | 0.4485 (5) | 0.2199 (7) | 0.6674 (4) | 0.0502 (12) | |
H11 | 0.5044 | 0.1964 | 0.7404 | 0.060* | |
C18 | 0.0214 (5) | 0.1302 (7) | −0.2335 (4) | 0.0481 (12) | |
H18 | 0.058 (2) | 0.079 (3) | −0.292 (3) | 0.058* | |
C8 | 0.4424 (5) | 0.1376 (6) | 0.3573 (4) | 0.0460 (11) | |
H8A | 0.548 (4) | 0.1175 (10) | 0.3753 (7) | 0.055* | |
H8B | 0.3941 (17) | 0.018 (4) | 0.3320 (9) | 0.055* | |
C15 | 0.1368 (4) | 0.2643 (7) | 0.0766 (4) | 0.0454 (12) | |
H15A | 0.0933 (15) | 0.364 (3) | 0.1186 (15) | 0.054* | |
H15B | 0.1420 (4) | 0.149 (4) | 0.1272 (18) | 0.054* | |
C7 | 0.7381 (4) | 0.1431 (6) | 0.1276 (4) | 0.0419 (10) | |
H7 | 0.7094 | 0.0942 | 0.0538 | 0.050* | |
C19 | −0.1103 (5) | 0.1741 (7) | −0.2565 (4) | 0.0494 (13) | |
H19 | −0.164 (3) | 0.1531 (14) | −0.327 (4) | 0.059* | |
C6 | 0.8590 (5) | 0.0974 (6) | 0.1974 (4) | 0.0470 (12) | |
H6 | 0.918 (3) | 0.009 (5) | 0.1677 (16) | 0.056* | |
C12 | 0.3337 (6) | 0.3025 (8) | 0.6596 (5) | 0.0594 (15) | |
H12 | 0.3088 | 0.3365 | 0.7272 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0336 (5) | 0.0304 (6) | 0.0304 (5) | −0.0026 (4) | 0.0082 (4) | 0.0004 (4) |
Cl1 | 0.0613 (8) | 0.0802 (11) | 0.0410 (6) | −0.0028 (7) | −0.0065 (5) | −0.0050 (6) |
O2 | 0.0463 (17) | 0.0322 (17) | 0.0348 (14) | 0.0037 (12) | 0.0154 (12) | 0.0014 (12) |
O4 | 0.060 (2) | 0.056 (2) | 0.0313 (15) | −0.0126 (16) | 0.0151 (14) | −0.0007 (14) |
O1 | 0.0498 (19) | 0.0327 (18) | 0.0408 (16) | −0.0045 (14) | 0.0149 (14) | −0.0031 (13) |
O3 | 0.0353 (16) | 0.047 (2) | 0.0509 (17) | −0.0045 (14) | 0.0029 (13) | 0.0120 (15) |
C2 | 0.030 (2) | 0.031 (2) | 0.0358 (19) | −0.0061 (16) | 0.0123 (16) | 0.0046 (16) |
C3 | 0.032 (2) | 0.030 (2) | 0.046 (2) | −0.0003 (17) | 0.0084 (18) | 0.0003 (18) |
C9 | 0.046 (2) | 0.030 (2) | 0.038 (2) | −0.010 (2) | 0.0198 (18) | −0.005 (2) |
C4 | 0.039 (2) | 0.041 (3) | 0.039 (2) | −0.0078 (19) | 0.0048 (18) | 0.0057 (19) |
C5 | 0.034 (2) | 0.032 (3) | 0.067 (3) | −0.0012 (18) | 0.012 (2) | 0.011 (2) |
C14 | 0.043 (3) | 0.042 (3) | 0.053 (3) | 0.000 (2) | 0.008 (2) | −0.002 (2) |
C21 | 0.041 (2) | 0.035 (3) | 0.051 (3) | 0.0006 (19) | 0.020 (2) | 0.003 (2) |
C20 | 0.036 (2) | 0.047 (3) | 0.059 (3) | 0.002 (2) | 0.007 (2) | 0.005 (2) |
C13 | 0.049 (3) | 0.045 (3) | 0.086 (4) | −0.008 (2) | 0.038 (3) | −0.015 (3) |
C10 | 0.042 (2) | 0.033 (3) | 0.048 (2) | −0.0031 (18) | 0.0109 (19) | 0.0041 (18) |
C17 | 0.039 (2) | 0.042 (3) | 0.039 (2) | 0.0072 (19) | 0.0093 (18) | 0.0051 (18) |
C1 | 0.039 (2) | 0.037 (3) | 0.033 (2) | −0.0066 (19) | 0.0087 (17) | 0.0011 (17) |
C16 | 0.033 (2) | 0.036 (3) | 0.041 (2) | −0.0009 (18) | 0.0114 (17) | 0.0069 (19) |
C11 | 0.072 (3) | 0.042 (3) | 0.038 (2) | −0.021 (3) | 0.014 (2) | −0.005 (2) |
C18 | 0.060 (3) | 0.042 (3) | 0.045 (2) | 0.002 (2) | 0.019 (2) | −0.005 (2) |
C8 | 0.063 (3) | 0.037 (3) | 0.043 (2) | 0.014 (2) | 0.022 (2) | 0.010 (2) |
C15 | 0.036 (2) | 0.059 (3) | 0.045 (2) | −0.002 (2) | 0.0163 (19) | 0.001 (2) |
C7 | 0.044 (3) | 0.038 (3) | 0.048 (2) | −0.007 (2) | 0.019 (2) | −0.0059 (19) |
C19 | 0.055 (3) | 0.047 (3) | 0.039 (2) | −0.006 (2) | −0.003 (2) | 0.001 (2) |
C6 | 0.043 (3) | 0.034 (3) | 0.070 (3) | 0.001 (2) | 0.026 (2) | −0.001 (2) |
C12 | 0.080 (4) | 0.055 (4) | 0.055 (3) | −0.022 (3) | 0.038 (3) | −0.022 (3) |
P1—O1 | 1.473 (3) | C20—C19 | 1.378 (7) |
P1—O3 | 1.566 (3) | C20—H20 | 0.88 (5) |
P1—O2 | 1.578 (3) | C13—C12 | 1.347 (8) |
P1—C1 | 1.819 (4) | C13—H13 | 0.9500 |
Cl1—C4 | 1.732 (5) | C10—C11 | 1.394 (6) |
O2—C8 | 1.463 (5) | C10—H10 | 0.9500 |
O4—C1 | 1.432 (5) | C17—C16 | 1.372 (6) |
O4—H4 | 0.8400 | C17—C18 | 1.389 (6) |
O3—C15 | 1.472 (5) | C17—H17 | 0.94 (5) |
C2—C3 | 1.389 (6) | C1—H1 | 1.0000 |
C2—C7 | 1.394 (6) | C16—C15 | 1.514 (6) |
C2—C1 | 1.506 (6) | C11—C12 | 1.346 (8) |
C3—C4 | 1.391 (6) | C11—H11 | 0.9500 |
C3—H3 | 0.92 (5) | C18—C19 | 1.379 (7) |
C9—C14 | 1.393 (6) | C18—H18 | 0.97 (5) |
C9—C10 | 1.393 (6) | C8—H8A | 1.08 (4) |
C9—C8 | 1.492 (6) | C8—H8B | 1.08 (4) |
C4—C5 | 1.386 (7) | C15—H15A | 1.09 (4) |
C5—C6 | 1.367 (7) | C15—H15B | 1.09 (4) |
C5—H5 | 0.94 (5) | C7—C6 | 1.386 (7) |
C14—C13 | 1.395 (7) | C7—H7 | 0.9500 |
C14—H14 | 0.9500 | C19—H19 | 0.92 (5) |
C21—C20 | 1.374 (7) | C6—H6 | 1.04 (5) |
C21—C16 | 1.377 (6) | C12—H12 | 0.9500 |
C21—H21 | 0.94 (5) | ||
O1—P1—O3 | 115.92 (18) | C18—C17—H17 | 119.9 |
O1—P1—O2 | 113.06 (17) | O4—C1—C2 | 113.3 (3) |
O3—P1—O2 | 103.29 (17) | O4—C1—P1 | 104.0 (3) |
O1—P1—C1 | 115.33 (19) | C2—C1—P1 | 110.9 (3) |
O3—P1—C1 | 101.24 (19) | O4—C1—H1 | 109.5 |
O2—P1—C1 | 106.57 (18) | C2—C1—H1 | 109.5 |
C8—O2—P1 | 121.3 (3) | P1—C1—H1 | 109.5 |
C1—O4—H4 | 109.5 | C17—C16—C21 | 119.6 (4) |
C15—O3—P1 | 119.2 (3) | C17—C16—C15 | 121.2 (4) |
C3—C2—C7 | 119.0 (4) | C21—C16—C15 | 119.2 (4) |
C3—C2—C1 | 119.3 (4) | C12—C11—C10 | 120.4 (5) |
C7—C2—C1 | 121.7 (4) | C12—C11—H11 | 119.8 |
C2—C3—C4 | 119.7 (4) | C10—C11—H11 | 119.8 |
C2—C3—H3 | 120.2 | C19—C18—C17 | 119.9 (5) |
C4—C3—H3 | 120.2 | C19—C18—H18 | 120.0 |
C14—C9—C10 | 118.3 (4) | C17—C18—H18 | 120.0 |
C14—C9—C8 | 122.0 (4) | O2—C8—C9 | 109.5 (4) |
C10—C9—C8 | 119.6 (4) | O2—C8—H8A | 109.8 |
C5—C4—C3 | 121.2 (4) | C9—C8—H8A | 109.8 |
C5—C4—Cl1 | 120.5 (4) | O2—C8—H8B | 109.8 |
C3—C4—Cl1 | 118.3 (4) | C9—C8—H8B | 109.8 |
C6—C5—C4 | 118.6 (5) | H8A—C8—H8B | 108.2 |
C6—C5—H5 | 120.7 | O3—C15—C16 | 109.7 (3) |
C4—C5—H5 | 120.7 | O3—C15—H15A | 109.7 |
C9—C14—C13 | 119.3 (5) | C16—C15—H15A | 109.7 |
C9—C14—H14 | 120.3 | O3—C15—H15B | 109.7 |
C13—C14—H14 | 120.3 | C16—C15—H15B | 109.7 |
C20—C21—C16 | 120.5 (4) | H15A—C15—H15B | 108.2 |
C20—C21—H21 | 119.8 | C6—C7—C2 | 120.0 (4) |
C16—C21—H21 | 119.8 | C6—C7—H7 | 120.0 |
C21—C20—C19 | 120.3 (4) | C2—C7—H7 | 120.0 |
C21—C20—H20 | 119.9 | C20—C19—C18 | 119.5 (4) |
C19—C20—H20 | 119.9 | C20—C19—H19 | 120.2 |
C12—C13—C14 | 121.2 (5) | C18—C19—H19 | 120.2 |
C12—C13—H13 | 119.4 | C5—C6—C7 | 121.5 (4) |
C14—C13—H13 | 119.4 | C5—C6—H6 | 119.2 |
C9—C10—C11 | 120.3 (5) | C7—C6—H6 | 119.2 |
C9—C10—H10 | 119.9 | C11—C12—C13 | 120.5 (5) |
C11—C10—H10 | 119.9 | C11—C12—H12 | 119.7 |
C16—C17—C18 | 120.2 (4) | C13—C12—H12 | 119.7 |
C16—C17—H17 | 119.9 | ||
O1—P1—O2—C8 | 17.5 (4) | O2—P1—C1—O4 | −178.1 (3) |
O3—P1—O2—C8 | 143.6 (3) | O1—P1—C1—C2 | −66.5 (3) |
C1—P1—O2—C8 | −110.2 (3) | O3—P1—C1—C2 | 167.5 (3) |
O1—P1—O3—C15 | 51.4 (4) | O2—P1—C1—C2 | 59.8 (3) |
O2—P1—O3—C15 | −72.8 (3) | C18—C17—C16—C21 | −1.1 (7) |
C1—P1—O3—C15 | 177.0 (3) | C18—C17—C16—C15 | 178.7 (4) |
C7—C2—C3—C4 | −1.3 (6) | C20—C21—C16—C17 | 2.4 (7) |
C1—C2—C3—C4 | 179.3 (4) | C20—C21—C16—C15 | −177.4 (5) |
C2—C3—C4—C5 | 2.5 (6) | C9—C10—C11—C12 | 0.1 (7) |
C2—C3—C4—Cl1 | −178.7 (3) | C16—C17—C18—C19 | −0.7 (7) |
C3—C4—C5—C6 | −2.3 (7) | P1—O2—C8—C9 | −162.5 (3) |
Cl1—C4—C5—C6 | 178.9 (3) | C14—C9—C8—O2 | 39.0 (6) |
C10—C9—C14—C13 | 0.1 (7) | C10—C9—C8—O2 | −144.8 (4) |
C8—C9—C14—C13 | 176.4 (5) | P1—O3—C15—C16 | −124.0 (4) |
C16—C21—C20—C19 | −2.0 (7) | C17—C16—C15—O3 | 37.6 (6) |
C9—C14—C13—C12 | −0.3 (8) | C21—C16—C15—O3 | −142.6 (4) |
C14—C9—C10—C11 | 0.0 (7) | C3—C2—C7—C6 | −0.1 (6) |
C8—C9—C10—C11 | −176.4 (4) | C1—C2—C7—C6 | 179.4 (4) |
C3—C2—C1—O4 | 164.9 (4) | C21—C20—C19—C18 | 0.2 (8) |
C7—C2—C1—O4 | −14.5 (6) | C17—C18—C19—C20 | 1.1 (8) |
C3—C2—C1—P1 | −78.6 (4) | C4—C5—C6—C7 | 0.9 (7) |
C7—C2—C1—P1 | 102.0 (4) | C2—C7—C6—C5 | 0.2 (7) |
O1—P1—C1—O4 | 55.6 (3) | C10—C11—C12—C13 | −0.3 (8) |
O3—P1—C1—O4 | −70.4 (3) | C14—C13—C12—C11 | 0.4 (8) |
C21H20NO6P | Z = 4 |
Mr = 413.35 | F(000) = 864 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
a = 10.0795 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.8530 (6) Å | Cell parameters from 8023 reflections |
c = 15.9354 (5) Å | θ = 4.2–31.4° |
α = 111.110 (4)° | µ = 0.18 mm−1 |
β = 90.852 (3)° | T = 133 K |
γ = 106.326 (3)° | Block, colorless |
V = 1975.23 (13) Å3 | 0.43 × 0.30 × 0.25 mm |
Agilent Xcalibur Sapphire3 diffractometer | 11989 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 8512 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.038 |
ω scans | θmax = 30.5°, θmin = 4.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −14→14 |
Tmin = 0.980, Tmax = 1.000 | k = −19→19 |
39828 measured reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.5554P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
11989 reflections | Δρmax = 0.60 e Å−3 |
565 parameters | Δρmin = −0.30 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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. An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.34036 (4) | 0.33610 (3) | 0.24334 (2) | 0.01798 (9) | |
H400 | 0.484 (2) | 0.5613 (17) | 0.3690 (13) | 0.033 (5)* | |
P2 | 0.65755 (4) | 0.70132 (3) | 0.27149 (2) | 0.01823 (9) | |
H100 | 0.496 (2) | 0.4733 (18) | 0.1433 (14) | 0.049 (6)* | |
O9 | 0.81171 (10) | 0.77607 (8) | 0.30493 (7) | 0.0215 (2) | |
O2 | 0.19137 (10) | 0.25153 (8) | 0.20799 (7) | 0.0211 (2) | |
O8 | 0.59353 (10) | 0.76486 (8) | 0.22569 (7) | 0.0227 (2) | |
O4 | 0.44813 (11) | 0.50956 (9) | 0.38479 (7) | 0.0235 (2) | |
O3 | 0.41292 (10) | 0.28115 (9) | 0.29324 (8) | 0.0236 (2) | |
C23 | 0.78247 (15) | 0.60271 (11) | 0.11945 (10) | 0.0191 (3) | |
O10 | 0.53685 (11) | 0.53214 (9) | 0.12951 (7) | 0.0246 (2) | |
O7 | 0.57636 (11) | 0.67567 (9) | 0.34107 (7) | 0.0258 (2) | |
N1 | −0.00314 (13) | 0.38299 (11) | 0.28147 (9) | 0.0257 (3) | |
O5 | 0.06966 (12) | 0.42184 (10) | 0.23397 (8) | 0.0307 (3) | |
C22 | 0.67239 (15) | 0.58044 (11) | 0.18032 (10) | 0.0194 (3) | |
H22 | 0.6919 (4) | 0.5306 (9) | 0.2066 (5) | 0.023* | |
N2 | 0.98969 (14) | 0.62531 (11) | 0.22338 (9) | 0.0252 (3) | |
C24 | 0.92640 (15) | 0.62283 (12) | 0.13842 (10) | 0.0212 (3) | |
C7 | 0.25435 (16) | 0.42323 (12) | 0.47355 (10) | 0.0229 (3) | |
H7 | 0.3525 (19) | 0.4450 (4) | 0.4915 (4) | 0.027* | |
C1 | 0.31458 (14) | 0.45437 (11) | 0.33225 (9) | 0.0183 (3) | |
H1 | 0.2883 (5) | 0.5001 (8) | 0.3057 (5) | 0.022* | |
C16 | 0.03692 (16) | 0.07050 (12) | 0.12503 (10) | 0.0239 (3) | |
C2 | 0.20635 (14) | 0.42283 (11) | 0.39074 (9) | 0.0184 (3) | |
C37 | 0.40708 (15) | 0.77098 (13) | 0.13515 (11) | 0.0247 (3) | |
O1 | 0.41947 (11) | 0.36438 (9) | 0.17393 (7) | 0.0252 (2) | |
C4 | −0.03052 (17) | 0.35731 (14) | 0.42395 (11) | 0.0271 (3) | |
H4 | −0.126 (2) | 0.3347 (5) | 0.4066 (4) | 0.033* | |
C10 | 0.59503 (17) | 0.26396 (14) | 0.44355 (12) | 0.0303 (4) | |
H10 | 0.5792 (4) | 0.3293 (14) | 0.4789 (8) | 0.036* | |
C3 | 0.06145 (15) | 0.38843 (12) | 0.36733 (10) | 0.0207 (3) | |
C9 | 0.59567 (15) | 0.23593 (13) | 0.35077 (11) | 0.0247 (3) | |
O11 | 0.91432 (13) | 0.58963 (11) | 0.27171 (8) | 0.0348 (3) | |
O12 | 1.11618 (13) | 0.66325 (12) | 0.24296 (9) | 0.0416 (3) | |
C17 | −0.08745 (17) | 0.08349 (13) | 0.10044 (11) | 0.0281 (3) | |
H17 | −0.08650 (17) | 0.1468 (13) | 0.0867 (3) | 0.034* | |
C25 | 1.01936 (17) | 0.64088 (13) | 0.07796 (11) | 0.0275 (3) | |
H25 | 1.116 (2) | 0.6549 (3) | 0.0933 (3) | 0.033* | |
C28 | 0.73746 (17) | 0.60301 (12) | 0.03646 (10) | 0.0235 (3) | |
H28 | 0.6423 (19) | 0.5915 (3) | 0.0215 (3) | 0.028* | |
C36 | 0.44344 (16) | 0.74987 (15) | 0.21718 (12) | 0.0296 (4) | |
H36A | 0.4195 (4) | 0.8019 (7) | 0.2729 (7) | 0.036* | |
H36B | 0.3898 (7) | 0.6737 (10) | 0.20999 (14) | 0.036* | |
C14 | 0.62044 (16) | 0.13931 (13) | 0.29942 (11) | 0.0278 (3) | |
H14 | 0.62187 (17) | 0.1196 (4) | 0.2354 (13) | 0.033* | |
C31 | 1.00525 (19) | 1.04519 (13) | 0.37666 (11) | 0.0303 (4) | |
H31 | 0.9248 (17) | 1.0712 (6) | 0.37619 (11) | 0.036* | |
C8 | 0.56506 (16) | 0.30702 (14) | 0.30601 (13) | 0.0307 (4) | |
H8A | 0.6094 (6) | 0.3856 (10) | 0.3453 (5) | 0.037* | |
H8B | 0.6020 (5) | 0.2920 (2) | 0.2461 (8) | 0.037* | |
C21 | 0.03337 (19) | −0.01984 (14) | 0.14458 (11) | 0.0311 (4) | |
H21 | 0.1159 (19) | −0.0290 (2) | 0.1615 (4) | 0.037* | |
C30 | 0.98821 (15) | 0.94508 (12) | 0.38278 (10) | 0.0229 (3) | |
C26 | 0.97016 (18) | 0.63830 (14) | −0.00458 (11) | 0.0305 (4) | |
H26 | 1.0352 (13) | 0.6495 (3) | −0.0487 (9) | 0.037* | |
C35 | 1.10341 (17) | 0.90917 (14) | 0.38432 (11) | 0.0292 (3) | |
H35 | 1.0927 (3) | 0.8399 (15) | 0.38963 (16) | 0.035* | |
C29 | 0.84652 (17) | 0.87533 (13) | 0.38640 (11) | 0.0305 (4) | |
H29A | 0.84691 (17) | 0.8581 (3) | 0.4398 (8) | 0.037* | |
H29B | 0.7788 (10) | 0.9130 (5) | 0.38844 (12) | 0.037* | |
C19 | −0.21548 (19) | −0.08318 (14) | 0.11459 (11) | 0.0327 (4) | |
H19 | −0.3023 (19) | −0.1358 (11) | 0.11095 (14) | 0.039* | |
C42 | 0.39673 (17) | 0.69247 (14) | 0.04910 (12) | 0.0288 (3) | |
H42 | 0.4117 (3) | 0.6234 (14) | 0.04279 (17) | 0.035* | |
O6 | −0.12840 (13) | 0.33932 (14) | 0.26055 (10) | 0.0544 (4) | |
C6 | 0.16325 (17) | 0.39282 (14) | 0.53056 (11) | 0.0276 (3) | |
H6 | 0.1977 (8) | 0.39435 (14) | 0.5845 (12) | 0.033* | |
C18 | −0.21298 (18) | 0.00679 (14) | 0.09529 (12) | 0.0321 (4) | |
H18 | −0.3014 (19) | 0.0165 (3) | 0.0777 (4) | 0.038* | |
C11 | 0.61763 (19) | 0.19606 (16) | 0.48406 (13) | 0.0372 (4) | |
H11 | 0.61670 (19) | 0.2154 (5) | 0.5471 (14) | 0.045* | |
C27 | 0.82926 (18) | 0.61991 (14) | −0.02487 (11) | 0.0286 (3) | |
H27 | 0.7955 (7) | 0.61882 (14) | −0.0800 (12) | 0.034* | |
C20 | −0.0929 (2) | −0.09669 (14) | 0.13900 (12) | 0.0355 (4) | |
H20 | −0.0943 (2) | −0.1560 (14) | 0.1515 (3) | 0.043* | |
C5 | 0.02075 (18) | 0.36026 (14) | 0.50618 (11) | 0.0304 (4) | |
H5 | −0.0428 (13) | 0.3397 (4) | 0.5464 (8) | 0.036* | |
C38 | 0.38634 (18) | 0.86858 (15) | 0.14305 (12) | 0.0330 (4) | |
H38 | 0.3931 (2) | 0.9250 (12) | 0.2036 (13) | 0.040* | |
C15 | 0.17277 (18) | 0.15174 (14) | 0.12808 (12) | 0.0358 (4) | |
H15A | 0.2467 (11) | 0.1232 (4) | 0.13115 (12) | 0.043* | |
H15B | 0.17338 (19) | 0.1671 (3) | 0.0749 (8) | 0.043* | |
C41 | 0.36579 (19) | 0.71037 (16) | −0.02724 (12) | 0.0358 (4) | |
H41 | 0.3578 (3) | 0.6543 (12) | −0.0872 (13) | 0.043* | |
C34 | 1.23371 (19) | 0.97247 (17) | 0.37825 (12) | 0.0382 (4) | |
H34 | 1.3155 (18) | 0.9466 (6) | 0.37877 (12) | 0.046* | |
C13 | 0.64307 (19) | 0.07126 (15) | 0.33998 (12) | 0.0337 (4) | |
H13 | 0.6594 (4) | 0.0058 (15) | 0.3047 (8) | 0.040* | |
C33 | 1.2494 (2) | 1.07134 (17) | 0.37148 (12) | 0.0412 (5) | |
H33 | 1.337 (2) | 1.1134 (10) | 0.36705 (16) | 0.049* | |
C12 | 0.64167 (19) | 0.09951 (17) | 0.43228 (13) | 0.0368 (4) | |
H12 | 0.6571 (4) | 0.0532 (11) | 0.4601 (7) | 0.044* | |
C39 | 0.3561 (2) | 0.88701 (17) | 0.06609 (13) | 0.0415 (5) | |
H39 | 0.3421 (4) | 0.9554 (16) | 0.0719 (2) | 0.050* | |
C40 | 0.3460 (2) | 0.80819 (17) | −0.01888 (13) | 0.0411 (5) | |
H40 | 0.3252 (5) | 0.8212 (3) | −0.0722 (13) | 0.049* | |
C32 | 1.1362 (2) | 1.10841 (15) | 0.37123 (12) | 0.0387 (4) | |
H32 | 1.1473 (3) | 1.1748 (16) | 0.36747 (15) | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01575 (17) | 0.01667 (17) | 0.02039 (18) | 0.00240 (13) | 0.00380 (13) | 0.00764 (14) |
P2 | 0.01637 (17) | 0.01721 (17) | 0.01916 (18) | 0.00092 (13) | 0.00155 (13) | 0.00790 (14) |
O9 | 0.0162 (5) | 0.0184 (5) | 0.0230 (5) | 0.0006 (4) | −0.0003 (4) | 0.0035 (4) |
O2 | 0.0166 (5) | 0.0184 (5) | 0.0228 (5) | 0.0021 (4) | 0.0029 (4) | 0.0040 (4) |
O8 | 0.0172 (5) | 0.0242 (5) | 0.0291 (6) | 0.0043 (4) | 0.0033 (4) | 0.0145 (5) |
O4 | 0.0189 (5) | 0.0210 (5) | 0.0242 (5) | −0.0032 (4) | −0.0018 (4) | 0.0086 (4) |
O3 | 0.0146 (5) | 0.0244 (5) | 0.0361 (6) | 0.0051 (4) | 0.0053 (4) | 0.0169 (5) |
C23 | 0.0208 (7) | 0.0149 (6) | 0.0190 (7) | 0.0026 (5) | 0.0011 (5) | 0.0058 (5) |
O10 | 0.0203 (5) | 0.0218 (5) | 0.0253 (5) | −0.0033 (4) | −0.0036 (4) | 0.0093 (5) |
O7 | 0.0269 (6) | 0.0245 (5) | 0.0235 (5) | 0.0020 (4) | 0.0068 (4) | 0.0106 (4) |
N1 | 0.0200 (6) | 0.0308 (7) | 0.0273 (7) | 0.0079 (5) | 0.0010 (5) | 0.0119 (6) |
O5 | 0.0269 (6) | 0.0434 (7) | 0.0304 (6) | 0.0131 (5) | 0.0052 (5) | 0.0219 (5) |
C22 | 0.0190 (7) | 0.0165 (6) | 0.0196 (7) | 0.0009 (5) | −0.0006 (5) | 0.0071 (5) |
N2 | 0.0247 (7) | 0.0295 (7) | 0.0239 (6) | 0.0123 (6) | 0.0016 (5) | 0.0100 (6) |
C24 | 0.0221 (7) | 0.0208 (7) | 0.0197 (7) | 0.0064 (6) | 0.0013 (5) | 0.0067 (6) |
C7 | 0.0212 (7) | 0.0230 (7) | 0.0212 (7) | 0.0023 (6) | 0.0008 (6) | 0.0080 (6) |
C1 | 0.0172 (6) | 0.0167 (6) | 0.0194 (7) | 0.0019 (5) | 0.0017 (5) | 0.0075 (5) |
C16 | 0.0235 (7) | 0.0184 (7) | 0.0208 (7) | 0.0014 (6) | 0.0047 (6) | 0.0010 (6) |
C2 | 0.0187 (7) | 0.0161 (6) | 0.0192 (7) | 0.0039 (5) | 0.0033 (5) | 0.0066 (5) |
C37 | 0.0167 (7) | 0.0290 (8) | 0.0304 (8) | 0.0088 (6) | 0.0044 (6) | 0.0122 (7) |
O1 | 0.0262 (6) | 0.0236 (5) | 0.0251 (5) | 0.0040 (4) | 0.0088 (4) | 0.0110 (4) |
C4 | 0.0183 (7) | 0.0324 (8) | 0.0281 (8) | 0.0044 (6) | 0.0058 (6) | 0.0109 (7) |
C10 | 0.0227 (8) | 0.0283 (8) | 0.0328 (9) | 0.0087 (7) | 0.0030 (6) | 0.0031 (7) |
C3 | 0.0190 (7) | 0.0219 (7) | 0.0195 (7) | 0.0047 (6) | 0.0011 (5) | 0.0072 (6) |
C9 | 0.0137 (6) | 0.0247 (7) | 0.0340 (8) | 0.0043 (6) | 0.0010 (6) | 0.0106 (7) |
O11 | 0.0323 (6) | 0.0561 (8) | 0.0299 (6) | 0.0225 (6) | 0.0096 (5) | 0.0252 (6) |
O12 | 0.0249 (6) | 0.0562 (9) | 0.0417 (7) | 0.0060 (6) | −0.0060 (5) | 0.0215 (7) |
C17 | 0.0320 (9) | 0.0220 (7) | 0.0316 (8) | 0.0091 (6) | 0.0073 (7) | 0.0109 (7) |
C25 | 0.0222 (8) | 0.0307 (8) | 0.0276 (8) | 0.0075 (6) | 0.0055 (6) | 0.0093 (7) |
C28 | 0.0230 (7) | 0.0239 (7) | 0.0216 (7) | 0.0028 (6) | 0.0000 (6) | 0.0097 (6) |
C36 | 0.0200 (7) | 0.0417 (10) | 0.0339 (9) | 0.0135 (7) | 0.0076 (6) | 0.0188 (8) |
C14 | 0.0252 (8) | 0.0303 (8) | 0.0250 (8) | 0.0107 (7) | 0.0007 (6) | 0.0056 (7) |
C31 | 0.0330 (9) | 0.0247 (8) | 0.0271 (8) | 0.0053 (7) | −0.0001 (7) | 0.0059 (7) |
C8 | 0.0143 (7) | 0.0323 (9) | 0.0500 (11) | 0.0047 (6) | 0.0049 (7) | 0.0223 (8) |
C21 | 0.0345 (9) | 0.0292 (8) | 0.0265 (8) | 0.0112 (7) | −0.0011 (7) | 0.0060 (7) |
C30 | 0.0206 (7) | 0.0213 (7) | 0.0180 (7) | 0.0000 (6) | 0.0011 (5) | 0.0025 (6) |
C26 | 0.0301 (8) | 0.0344 (9) | 0.0251 (8) | 0.0056 (7) | 0.0079 (7) | 0.0125 (7) |
C35 | 0.0295 (8) | 0.0281 (8) | 0.0282 (8) | 0.0079 (7) | 0.0047 (7) | 0.0091 (7) |
C29 | 0.0236 (8) | 0.0265 (8) | 0.0243 (8) | −0.0039 (6) | 0.0043 (6) | −0.0011 (6) |
C19 | 0.0346 (9) | 0.0247 (8) | 0.0277 (8) | −0.0018 (7) | 0.0076 (7) | 0.0055 (7) |
C42 | 0.0247 (8) | 0.0255 (8) | 0.0354 (9) | 0.0107 (6) | 0.0045 (7) | 0.0085 (7) |
O6 | 0.0215 (6) | 0.0889 (12) | 0.0506 (9) | −0.0042 (7) | −0.0089 (6) | 0.0404 (9) |
C6 | 0.0279 (8) | 0.0330 (8) | 0.0205 (7) | 0.0042 (7) | 0.0028 (6) | 0.0127 (7) |
C18 | 0.0260 (8) | 0.0335 (9) | 0.0319 (9) | 0.0082 (7) | 0.0036 (7) | 0.0077 (7) |
C11 | 0.0357 (10) | 0.0486 (11) | 0.0265 (9) | 0.0158 (9) | 0.0033 (7) | 0.0113 (8) |
C27 | 0.0320 (9) | 0.0307 (8) | 0.0216 (7) | 0.0042 (7) | 0.0017 (6) | 0.0125 (7) |
C20 | 0.0543 (12) | 0.0212 (8) | 0.0293 (9) | 0.0062 (8) | 0.0048 (8) | 0.0119 (7) |
C5 | 0.0277 (8) | 0.0350 (9) | 0.0264 (8) | 0.0038 (7) | 0.0095 (7) | 0.0135 (7) |
C38 | 0.0359 (9) | 0.0319 (9) | 0.0304 (9) | 0.0171 (8) | 0.0012 (7) | 0.0062 (7) |
C15 | 0.0307 (9) | 0.0243 (8) | 0.0328 (9) | −0.0021 (7) | 0.0109 (7) | −0.0038 (7) |
C41 | 0.0367 (10) | 0.0427 (10) | 0.0282 (9) | 0.0221 (8) | 0.0050 (7) | 0.0061 (8) |
C34 | 0.0230 (8) | 0.0537 (12) | 0.0311 (9) | 0.0096 (8) | 0.0042 (7) | 0.0101 (8) |
C13 | 0.0360 (9) | 0.0317 (9) | 0.0345 (9) | 0.0186 (8) | 0.0004 (7) | 0.0076 (7) |
C33 | 0.0300 (9) | 0.0445 (11) | 0.0302 (9) | −0.0106 (8) | 0.0033 (7) | 0.0095 (8) |
C12 | 0.0356 (10) | 0.0463 (11) | 0.0381 (10) | 0.0201 (9) | 0.0009 (8) | 0.0214 (9) |
C39 | 0.0545 (12) | 0.0402 (10) | 0.0408 (10) | 0.0311 (10) | 0.0054 (9) | 0.0155 (9) |
C40 | 0.0489 (12) | 0.0548 (12) | 0.0339 (10) | 0.0331 (10) | 0.0084 (8) | 0.0198 (9) |
C32 | 0.0515 (12) | 0.0240 (8) | 0.0293 (9) | −0.0042 (8) | 0.0022 (8) | 0.0094 (7) |
P1—O1 | 1.4749 (11) | C28—C27 | 1.391 (2) |
P1—O2 | 1.5670 (10) | C28—H28 | 0.940 (18) |
P1—O3 | 1.5743 (11) | C36—H36A | 1.005 (13) |
P1—C1 | 1.8269 (14) | C36—H36B | 1.005 (13) |
P2—O7 | 1.4739 (11) | C14—C13 | 1.383 (2) |
P2—O9 | 1.5634 (10) | C14—H14 | 0.958 (19) |
P2—O8 | 1.5785 (11) | C31—C32 | 1.387 (2) |
P2—C22 | 1.8255 (15) | C31—C30 | 1.388 (2) |
O9—C29 | 1.4590 (18) | C31—H31 | 0.98 (2) |
O2—C15 | 1.4653 (18) | C8—H8A | 1.002 (13) |
O8—C36 | 1.4654 (18) | C8—H8B | 1.002 (13) |
O4—C1 | 1.4228 (17) | C21—C20 | 1.388 (2) |
O4—H400 | 0.83 (2) | C21—H21 | 0.93 (2) |
O3—C8 | 1.4665 (18) | C30—C35 | 1.389 (2) |
C23—C28 | 1.394 (2) | C30—C29 | 1.498 (2) |
C23—C24 | 1.405 (2) | C26—C27 | 1.382 (2) |
C23—C22 | 1.5238 (19) | C26—H26 | 0.992 (19) |
O10—C22 | 1.4257 (17) | C35—C34 | 1.386 (2) |
O10—H100 | 0.91 (2) | C35—H35 | 0.97 (2) |
N1—O6 | 1.2182 (17) | C29—H29A | 0.963 (13) |
N1—O5 | 1.2202 (17) | C29—H29B | 0.963 (13) |
N1—C3 | 1.4740 (19) | C19—C20 | 1.372 (3) |
C22—H22 | 0.987 (17) | C19—C18 | 1.381 (3) |
N2—O12 | 1.2216 (17) | C19—H19 | 0.95 (2) |
N2—O11 | 1.2229 (17) | C42—C41 | 1.374 (2) |
N2—C24 | 1.4729 (19) | C42—H42 | 0.98 (2) |
C24—C25 | 1.392 (2) | C6—C5 | 1.382 (2) |
C7—C6 | 1.389 (2) | C6—H6 | 0.913 (19) |
C7—C2 | 1.396 (2) | C18—H18 | 0.99 (2) |
C7—H7 | 0.955 (18) | C11—C12 | 1.386 (3) |
C1—C2 | 1.5183 (19) | C11—H11 | 0.94 (2) |
C1—H1 | 0.968 (17) | C27—H27 | 0.93 (2) |
C16—C17 | 1.386 (2) | C20—H20 | 0.91 (2) |
C16—C21 | 1.386 (2) | C5—H5 | 0.971 (19) |
C16—C15 | 1.495 (2) | C38—C39 | 1.386 (3) |
C2—C3 | 1.401 (2) | C38—H38 | 0.99 (2) |
C37—C38 | 1.387 (2) | C15—H15A | 0.945 (14) |
C37—C42 | 1.390 (2) | C15—H15B | 0.945 (14) |
C37—C36 | 1.500 (2) | C41—C40 | 1.384 (3) |
C4—C5 | 1.384 (2) | C41—H41 | 0.98 (2) |
C4—C3 | 1.393 (2) | C34—C33 | 1.377 (3) |
C4—H4 | 0.926 (19) | C34—H34 | 0.99 (2) |
C10—C11 | 1.381 (3) | C13—C12 | 1.380 (3) |
C10—C9 | 1.387 (2) | C13—H13 | 0.94 (2) |
C10—H10 | 0.94 (2) | C33—C32 | 1.378 (3) |
C9—C14 | 1.389 (2) | C33—H33 | 0.93 (2) |
C9—C8 | 1.498 (2) | C12—H12 | 0.94 (2) |
C17—C18 | 1.384 (2) | C39—C40 | 1.380 (3) |
C17—H17 | 0.98 (2) | C39—H39 | 0.97 (2) |
C25—C26 | 1.383 (2) | C40—H40 | 0.96 (2) |
C25—H25 | 0.948 (19) | C32—H32 | 0.92 (2) |
O1—P1—O2 | 115.93 (6) | C32—C31—C30 | 120.22 (17) |
O1—P1—O3 | 113.27 (6) | C32—C31—H31 | 119.9 |
O2—P1—O3 | 102.41 (6) | C30—C31—H31 | 119.9 |
O1—P1—C1 | 112.69 (6) | O3—C8—C9 | 106.44 (12) |
O2—P1—C1 | 105.42 (6) | O3—C8—H8A | 110.4 |
O3—P1—C1 | 106.07 (6) | C9—C8—H8A | 110.4 |
O7—P2—O9 | 116.27 (6) | O3—C8—H8B | 110.4 |
O7—P2—O8 | 112.73 (6) | C9—C8—H8B | 110.4 |
O9—P2—O8 | 102.91 (6) | H8A—C8—H8B | 108.6 |
O7—P2—C22 | 112.87 (6) | C16—C21—C20 | 120.52 (17) |
O9—P2—C22 | 104.04 (6) | C16—C21—H21 | 119.7 |
O8—P2—C22 | 107.00 (6) | C20—C21—H21 | 119.7 |
C29—O9—P2 | 121.07 (9) | C31—C30—C35 | 119.51 (15) |
C15—O2—P1 | 119.34 (9) | C31—C30—C29 | 120.41 (15) |
C36—O8—P2 | 121.24 (9) | C35—C30—C29 | 120.07 (15) |
C1—O4—H400 | 106.0 (14) | C27—C26—C25 | 119.23 (15) |
C8—O3—P1 | 121.25 (9) | C27—C26—H26 | 120.4 |
C28—C23—C24 | 116.06 (13) | C25—C26—H26 | 120.4 |
C28—C23—C22 | 117.55 (13) | C34—C35—C30 | 119.92 (17) |
C24—C23—C22 | 126.39 (13) | C34—C35—H35 | 120.0 |
C22—O10—H100 | 105.9 (14) | C30—C35—H35 | 120.0 |
O6—N1—O5 | 122.33 (14) | O9—C29—C30 | 107.49 (12) |
O6—N1—C3 | 118.26 (13) | O9—C29—H29A | 110.2 |
O5—N1—C3 | 119.42 (12) | C30—C29—H29A | 110.2 |
O10—C22—C23 | 110.48 (11) | O9—C29—H29B | 110.2 |
O10—C22—P2 | 103.59 (9) | C30—C29—H29B | 110.2 |
C23—C22—P2 | 114.88 (10) | H29A—C29—H29B | 108.5 |
O10—C22—H22 | 109.2 | C20—C19—C18 | 119.87 (16) |
C23—C22—H22 | 109.2 | C20—C19—H19 | 120.1 |
P2—C22—H22 | 109.2 | C18—C19—H19 | 120.1 |
O12—N2—O11 | 122.37 (14) | C41—C42—C37 | 120.89 (16) |
O12—N2—C24 | 118.50 (13) | C41—C42—H42 | 119.6 |
O11—N2—C24 | 119.13 (13) | C37—C42—H42 | 119.6 |
C25—C24—C23 | 122.44 (14) | C5—C6—C7 | 120.42 (15) |
C25—C24—N2 | 115.16 (13) | C5—C6—H6 | 119.8 |
C23—C24—N2 | 122.40 (13) | C7—C6—H6 | 119.8 |
C6—C7—C2 | 121.76 (14) | C19—C18—C17 | 120.38 (17) |
C6—C7—H7 | 119.1 | C19—C18—H18 | 119.8 |
C2—C7—H7 | 119.1 | C17—C18—H18 | 119.8 |
O4—C1—C2 | 110.39 (11) | C10—C11—C12 | 120.18 (17) |
O4—C1—P1 | 103.70 (9) | C10—C11—H11 | 119.9 |
C2—C1—P1 | 112.43 (9) | C12—C11—H11 | 119.9 |
O4—C1—H1 | 110.1 | C26—C27—C28 | 120.53 (15) |
C2—C1—H1 | 110.1 | C26—C27—H27 | 119.7 |
P1—C1—H1 | 110.1 | C28—C27—H27 | 119.7 |
C17—C16—C21 | 119.06 (15) | C19—C20—C21 | 120.02 (17) |
C17—C16—C15 | 120.16 (16) | C19—C20—H20 | 120.0 |
C21—C16—C15 | 120.76 (16) | C21—C20—H20 | 120.0 |
C7—C2—C3 | 116.59 (13) | C6—C5—C4 | 119.38 (15) |
C7—C2—C1 | 117.57 (13) | C6—C5—H5 | 120.3 |
C3—C2—C1 | 125.77 (13) | C4—C5—H5 | 120.3 |
C38—C37—C42 | 118.93 (16) | C39—C38—C37 | 120.22 (17) |
C38—C37—C36 | 121.39 (15) | C39—C38—H38 | 119.9 |
C42—C37—C36 | 119.67 (15) | C37—C38—H38 | 119.9 |
C5—C4—C3 | 119.88 (15) | O2—C15—C16 | 109.09 (12) |
C5—C4—H4 | 120.1 | O2—C15—H15A | 109.9 |
C3—C4—H4 | 120.1 | C16—C15—H15A | 109.9 |
C11—C10—C9 | 120.30 (16) | O2—C15—H15B | 109.9 |
C11—C10—H10 | 119.9 | C16—C15—H15B | 109.9 |
C9—C10—H10 | 119.9 | H15A—C15—H15B | 108.3 |
C4—C3—C2 | 121.95 (14) | C42—C41—C40 | 119.88 (17) |
C4—C3—N1 | 115.85 (13) | C42—C41—H41 | 120.1 |
C2—C3—N1 | 122.20 (13) | C40—C41—H41 | 120.1 |
C10—C9—C14 | 119.18 (16) | C33—C34—C35 | 120.16 (18) |
C10—C9—C8 | 120.42 (15) | C33—C34—H34 | 119.9 |
C14—C9—C8 | 120.37 (15) | C35—C34—H34 | 119.9 |
C18—C17—C16 | 120.15 (16) | C12—C13—C14 | 119.93 (17) |
C18—C17—H17 | 119.9 | C12—C13—H13 | 120.0 |
C16—C17—H17 | 119.9 | C14—C13—H13 | 120.0 |
C26—C25—C24 | 119.74 (15) | C34—C33—C32 | 120.37 (17) |
C26—C25—H25 | 120.1 | C34—C33—H33 | 119.8 |
C24—C25—H25 | 120.1 | C32—C33—H33 | 119.8 |
C27—C28—C23 | 121.98 (15) | C13—C12—C11 | 119.87 (18) |
C27—C28—H28 | 119.0 | C13—C12—H12 | 120.1 |
C23—C28—H28 | 119.0 | C11—C12—H12 | 120.1 |
O8—C36—C37 | 107.48 (12) | C40—C39—C38 | 120.17 (18) |
O8—C36—H36A | 110.2 | C40—C39—H39 | 119.9 |
C37—C36—H36A | 110.2 | C38—C39—H39 | 119.9 |
O8—C36—H36B | 110.2 | C39—C40—C41 | 119.91 (18) |
C37—C36—H36B | 110.2 | C39—C40—H40 | 120.0 |
H36A—C36—H36B | 108.5 | C41—C40—H40 | 120.0 |
C13—C14—C9 | 120.53 (16) | C33—C32—C31 | 119.81 (18) |
C13—C14—H14 | 119.7 | C33—C32—H32 | 120.1 |
C9—C14—H14 | 119.7 | C31—C32—H32 | 120.1 |
O7—P2—O9—C29 | −46.67 (14) | C11—C10—C9—C8 | 177.34 (15) |
O8—P2—O9—C29 | 77.05 (13) | C21—C16—C17—C18 | −0.2 (2) |
C22—P2—O9—C29 | −171.44 (12) | C15—C16—C17—C18 | 178.28 (15) |
O1—P1—O2—C15 | 47.15 (14) | C23—C24—C25—C26 | −0.6 (2) |
O3—P1—O2—C15 | −76.68 (13) | N2—C24—C25—C26 | 178.85 (15) |
C1—P1—O2—C15 | 172.54 (12) | C24—C23—C28—C27 | 1.3 (2) |
O7—P2—O8—C36 | −29.37 (13) | C22—C23—C28—C27 | −178.43 (14) |
O9—P2—O8—C36 | −155.41 (11) | P2—O8—C36—C37 | −151.53 (11) |
C22—P2—O8—C36 | 95.30 (12) | C38—C37—C36—O8 | −101.89 (17) |
O1—P1—O3—C8 | 30.14 (14) | C42—C37—C36—O8 | 76.69 (18) |
O2—P1—O3—C8 | 155.73 (12) | C10—C9—C14—C13 | 0.5 (2) |
C1—P1—O3—C8 | −93.98 (12) | C8—C9—C14—C13 | −177.33 (15) |
C28—C23—C22—O10 | 17.28 (18) | P1—O3—C8—C9 | −176.94 (10) |
C24—C23—C22—O10 | −162.46 (13) | C10—C9—C8—O3 | −80.39 (18) |
C28—C23—C22—P2 | −99.44 (14) | C14—C9—C8—O3 | 97.46 (16) |
C24—C23—C22—P2 | 80.82 (17) | C17—C16—C21—C20 | 0.5 (2) |
O7—P2—C22—O10 | 73.45 (10) | C15—C16—C21—C20 | −178.07 (15) |
O9—P2—C22—O10 | −159.63 (9) | C32—C31—C30—C35 | 0.6 (2) |
O8—P2—C22—O10 | −51.13 (10) | C32—C31—C30—C29 | −178.51 (15) |
O7—P2—C22—C23 | −165.96 (10) | C24—C25—C26—C27 | 1.3 (3) |
O9—P2—C22—C23 | −39.04 (12) | C31—C30—C35—C34 | −1.1 (2) |
O8—P2—C22—C23 | 69.46 (11) | C29—C30—C35—C34 | 178.09 (15) |
C28—C23—C24—C25 | −0.7 (2) | P2—O9—C29—C30 | −161.51 (11) |
C22—C23—C24—C25 | 179.04 (14) | C31—C30—C29—O9 | 115.86 (16) |
C28—C23—C24—N2 | 179.89 (13) | C35—C30—C29—O9 | −63.28 (19) |
C22—C23—C24—N2 | −0.4 (2) | C38—C37—C42—C41 | −0.3 (2) |
O12—N2—C24—C25 | 14.3 (2) | C36—C37—C42—C41 | −178.94 (15) |
O11—N2—C24—C25 | −165.73 (14) | C2—C7—C6—C5 | 0.4 (2) |
O12—N2—C24—C23 | −166.23 (14) | C20—C19—C18—C17 | 0.0 (3) |
O11—N2—C24—C23 | 13.7 (2) | C16—C17—C18—C19 | 0.0 (2) |
O1—P1—C1—O4 | −74.02 (10) | C9—C10—C11—C12 | 0.3 (3) |
O2—P1—C1—O4 | 158.60 (9) | C25—C26—C27—C28 | −0.7 (3) |
O3—P1—C1—O4 | 50.46 (10) | C23—C28—C27—C26 | −0.7 (2) |
O1—P1—C1—C2 | 166.73 (10) | C18—C19—C20—C21 | 0.2 (3) |
O2—P1—C1—C2 | 39.35 (12) | C16—C21—C20—C19 | −0.4 (3) |
O3—P1—C1—C2 | −68.79 (11) | C7—C6—C5—C4 | 0.6 (3) |
C6—C7—C2—C3 | −1.0 (2) | C3—C4—C5—C6 | −0.9 (3) |
C6—C7—C2—C1 | −178.26 (14) | C42—C37—C38—C39 | −0.1 (3) |
O4—C1—C2—C7 | −17.19 (18) | C36—C37—C38—C39 | 178.44 (16) |
P1—C1—C2—C7 | 98.08 (14) | P1—O2—C15—C16 | 162.34 (11) |
O4—C1—C2—C3 | 165.85 (13) | C17—C16—C15—O2 | 73.8 (2) |
P1—C1—C2—C3 | −78.88 (16) | C21—C16—C15—O2 | −107.72 (17) |
C5—C4—C3—C2 | 0.2 (2) | C37—C42—C41—C40 | 0.7 (3) |
C5—C4—C3—N1 | −179.72 (15) | C30—C35—C34—C33 | 0.6 (3) |
C7—C2—C3—C4 | 0.7 (2) | C9—C14—C13—C12 | −0.3 (3) |
C1—C2—C3—C4 | 177.68 (14) | C35—C34—C33—C32 | 0.4 (3) |
C7—C2—C3—N1 | −179.35 (13) | C14—C13—C12—C11 | 0.0 (3) |
C1—C2—C3—N1 | −2.4 (2) | C10—C11—C12—C13 | 0.0 (3) |
O6—N1—C3—C4 | −9.3 (2) | C37—C38—C39—C40 | 0.3 (3) |
O5—N1—C3—C4 | 170.73 (14) | C38—C39—C40—C41 | 0.1 (3) |
O6—N1—C3—C2 | 170.71 (16) | C42—C41—C40—C39 | −0.6 (3) |
O5—N1—C3—C2 | −9.2 (2) | C34—C33—C32—C31 | −0.8 (3) |
C11—C10—C9—C14 | −0.5 (2) | C30—C31—C32—C33 | 0.3 (3) |
C10H14NO6P | Z = 2 |
Mr = 275.19 | F(000) = 288 |
Triclinic, P1 | Dx = 1.450 Mg m−3 |
a = 8.1800 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4006 (6) Å | Cell parameters from 3426 reflections |
c = 9.9661 (4) Å | θ = 4.6–31.3° |
α = 102.173 (5)° | µ = 0.24 mm−1 |
β = 94.897 (4)° | T = 173 K |
γ = 107.504 (5)° | Block, colorless |
V = 630.26 (6) Å3 | 0.40 × 0.35 × 0.20 mm |
Agilent Xcalibur Sapphire3 diffractometer | 3827 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3070 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.028 |
ω scans | θmax = 30.5°, θmin = 4.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −11→11 |
Tmin = 0.948, Tmax = 1.000 | k = −11→11 |
12564 measured reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1729P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3827 reflections | Δρmax = 0.34 e Å−3 |
176 parameters | Δρmin = −0.28 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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. An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.25993 (4) | 0.15887 (5) | 0.41073 (4) | 0.02383 (11) | |
O4 | −0.01562 (13) | 0.24691 (13) | 0.42662 (11) | 0.0275 (2) | |
C3 | 0.12907 (16) | 0.32849 (17) | 0.24037 (13) | 0.0214 (2) | |
O2 | 0.37141 (13) | 0.12800 (15) | 0.29430 (11) | 0.0336 (3) | |
C5 | 0.07201 (16) | 0.18886 (17) | 0.31853 (13) | 0.0207 (2) | |
O1 | 0.21030 (13) | 0.02257 (14) | 0.48551 (11) | 0.0315 (2) | |
O3 | 0.37375 (14) | 0.33881 (14) | 0.50550 (11) | 0.0367 (3) | |
C8 | 0.22597 (19) | 0.57705 (19) | 0.09385 (15) | 0.0274 (3) | |
C9 | 0.10946 (19) | 0.48879 (18) | 0.28755 (15) | 0.0279 (3) | |
H9 | 0.0657 (9) | 0.5115 (5) | 0.3667 (17) | 0.033* | |
C10 | −0.04346 (18) | 0.01791 (18) | 0.22095 (15) | 0.0272 (3) | |
H10A | −0.0811 (12) | −0.0655 (10) | 0.2735 (6) | 0.041* | |
H10B | 0.0208 (8) | −0.0219 (9) | 0.1534 (10) | 0.041* | |
H10C | −0.1422 (13) | 0.0343 (4) | 0.1749 (10) | 0.041* | |
C11 | 0.20148 (18) | 0.29652 (18) | 0.11999 (14) | 0.0258 (3) | |
H11 | 0.2176 (3) | 0.185 (2) | 0.0872 (6) | 0.031* | |
N1 | 0.27623 (19) | 0.70781 (18) | 0.01358 (14) | 0.0357 (3) | |
C13 | 0.25077 (19) | 0.42079 (19) | 0.04627 (15) | 0.0282 (3) | |
H13 | 0.2968 (10) | 0.4007 (5) | −0.0291 (16) | 0.034* | |
O6 | 0.2299 (2) | 0.83360 (17) | 0.04140 (15) | 0.0505 (3) | |
C15 | 0.1568 (2) | 0.6144 (2) | 0.21369 (16) | 0.0312 (3) | |
H15 | 0.1421 (4) | 0.723 (2) | 0.2447 (7) | 0.037* | |
O5 | 0.3616 (3) | 0.6835 (2) | −0.07774 (19) | 0.0765 (6) | |
C17 | 0.5299 (2) | 0.0903 (3) | 0.3215 (2) | 0.0542 (6) | |
H17A | 0.6078 (14) | 0.1807 (16) | 0.3884 (15) | 0.081* | |
H17B | 0.5770 (13) | 0.075 (2) | 0.2408 (12) | 0.081* | |
H17C | 0.5063 (5) | −0.0089 (18) | 0.3526 (17) | 0.081* | |
C18 | 0.3562 (3) | 0.3990 (3) | 0.64670 (19) | 0.0507 (5) | |
H18A | 0.2565 (18) | 0.429 (2) | 0.64949 (19) | 0.076* | |
H18B | 0.4518 (17) | 0.4942 (18) | 0.6898 (8) | 0.076* | |
H18C | 0.349 (2) | 0.3126 (14) | 0.6924 (8) | 0.076* | |
H1A | −0.069 (3) | 0.159 (3) | 0.456 (3) | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01850 (16) | 0.02768 (19) | 0.02616 (18) | 0.00507 (13) | 0.00364 (12) | 0.01212 (14) |
O4 | 0.0301 (5) | 0.0268 (5) | 0.0299 (5) | 0.0110 (4) | 0.0150 (4) | 0.0100 (4) |
C3 | 0.0201 (6) | 0.0243 (6) | 0.0213 (6) | 0.0088 (5) | 0.0027 (4) | 0.0072 (5) |
O2 | 0.0254 (5) | 0.0518 (7) | 0.0353 (6) | 0.0211 (5) | 0.0108 (4) | 0.0208 (5) |
C5 | 0.0190 (5) | 0.0221 (6) | 0.0225 (6) | 0.0075 (5) | 0.0058 (4) | 0.0065 (5) |
O1 | 0.0246 (5) | 0.0351 (6) | 0.0406 (6) | 0.0087 (4) | 0.0068 (4) | 0.0225 (5) |
O3 | 0.0315 (6) | 0.0364 (6) | 0.0300 (5) | −0.0065 (5) | −0.0012 (4) | 0.0105 (5) |
C8 | 0.0290 (7) | 0.0301 (7) | 0.0275 (7) | 0.0110 (6) | 0.0065 (5) | 0.0137 (6) |
C9 | 0.0340 (7) | 0.0280 (7) | 0.0276 (7) | 0.0147 (6) | 0.0130 (6) | 0.0097 (5) |
C10 | 0.0236 (6) | 0.0252 (7) | 0.0293 (7) | 0.0048 (5) | 0.0022 (5) | 0.0051 (5) |
C11 | 0.0311 (7) | 0.0252 (6) | 0.0231 (6) | 0.0119 (5) | 0.0063 (5) | 0.0058 (5) |
N1 | 0.0443 (8) | 0.0364 (7) | 0.0346 (7) | 0.0165 (6) | 0.0127 (6) | 0.0189 (6) |
C13 | 0.0345 (7) | 0.0333 (7) | 0.0216 (6) | 0.0149 (6) | 0.0096 (5) | 0.0090 (5) |
O6 | 0.0756 (10) | 0.0413 (7) | 0.0533 (8) | 0.0321 (7) | 0.0246 (7) | 0.0267 (6) |
C15 | 0.0400 (8) | 0.0279 (7) | 0.0333 (7) | 0.0170 (6) | 0.0134 (6) | 0.0120 (6) |
O5 | 0.1234 (15) | 0.0685 (10) | 0.0812 (11) | 0.0551 (11) | 0.0753 (11) | 0.0527 (9) |
C17 | 0.0344 (9) | 0.0907 (16) | 0.0652 (13) | 0.0394 (10) | 0.0210 (9) | 0.0448 (12) |
C18 | 0.0494 (11) | 0.0493 (11) | 0.0326 (9) | −0.0051 (8) | 0.0025 (8) | −0.0009 (8) |
P1—O1 | 1.4708 (10) | C9—H9 | 0.902 (18) |
P1—O2 | 1.5625 (11) | C10—H10A | 0.955 (10) |
P1—O3 | 1.5636 (11) | C10—H10B | 0.955 (10) |
P1—C5 | 1.8330 (13) | C10—H10C | 0.955 (10) |
O4—C5 | 1.4258 (15) | C11—C13 | 1.3831 (19) |
O4—H1A | 0.86 (3) | C11—H11 | 0.979 (17) |
C3—C9 | 1.3914 (19) | N1—O6 | 1.2135 (18) |
C3—C11 | 1.3940 (18) | N1—O5 | 1.2137 (19) |
C3—C5 | 1.5228 (18) | C13—H13 | 0.876 (19) |
O2—C17 | 1.4414 (18) | C15—H15 | 0.944 (19) |
C5—C10 | 1.5292 (19) | C17—H17A | 0.922 (13) |
O3—C18 | 1.426 (2) | C17—H17B | 0.922 (13) |
C8—C13 | 1.380 (2) | C17—H17C | 0.922 (13) |
C8—C15 | 1.382 (2) | C18—H18A | 0.926 (13) |
C8—N1 | 1.4732 (18) | C18—H18B | 0.926 (13) |
C9—C15 | 1.3916 (19) | C18—H18C | 0.926 (13) |
O1—P1—O2 | 115.61 (6) | C5—C10—H10C | 109.5 |
O1—P1—O3 | 114.01 (6) | H10A—C10—H10C | 109.5 |
O2—P1—O3 | 102.79 (6) | H10B—C10—H10C | 109.5 |
O1—P1—C5 | 112.77 (6) | C13—C11—C3 | 120.80 (13) |
O2—P1—C5 | 103.31 (6) | C13—C11—H11 | 119.6 |
O3—P1—C5 | 107.26 (6) | C3—C11—H11 | 119.6 |
C5—O4—H1A | 107.4 (16) | O6—N1—O5 | 123.31 (14) |
C9—C3—C11 | 119.21 (12) | O6—N1—C8 | 118.61 (13) |
C9—C3—C5 | 120.69 (12) | O5—N1—C8 | 118.08 (13) |
C11—C3—C5 | 120.10 (12) | C8—C13—C11 | 118.65 (13) |
C17—O2—P1 | 121.67 (11) | C8—C13—H13 | 120.7 |
O4—C5—C3 | 108.65 (10) | C11—C13—H13 | 120.7 |
O4—C5—C10 | 111.20 (10) | C8—C15—C9 | 118.46 (13) |
C3—C5—C10 | 111.47 (11) | C8—C15—H15 | 120.8 |
O4—C5—P1 | 104.11 (8) | C9—C15—H15 | 120.8 |
C3—C5—P1 | 111.08 (8) | O2—C17—H17A | 109.5 |
C10—C5—P1 | 110.10 (9) | O2—C17—H17B | 109.5 |
C18—O3—P1 | 123.59 (11) | H17A—C17—H17B | 109.5 |
C13—C8—C15 | 122.26 (13) | O2—C17—H17C | 109.5 |
C13—C8—N1 | 118.35 (13) | H17A—C17—H17C | 109.5 |
C15—C8—N1 | 119.39 (13) | H17B—C17—H17C | 109.5 |
C3—C9—C15 | 120.60 (13) | O3—C18—H18A | 109.5 |
C3—C9—H9 | 119.7 | O3—C18—H18B | 109.5 |
C15—C9—H9 | 119.7 | H18A—C18—H18B | 109.5 |
C5—C10—H10A | 109.5 | O3—C18—H18C | 109.5 |
C5—C10—H10B | 109.5 | H18A—C18—H18C | 109.5 |
H10A—C10—H10B | 109.5 | H18B—C18—H18C | 109.5 |
O1—P1—O2—C17 | −53.42 (16) | O1—P1—O3—C18 | −33.54 (16) |
O3—P1—O2—C17 | 71.43 (15) | O2—P1—O3—C18 | −159.44 (14) |
C5—P1—O2—C17 | −177.09 (14) | C5—P1—O3—C18 | 92.04 (15) |
C9—C3—C5—O4 | 6.74 (17) | C11—C3—C9—C15 | 1.8 (2) |
C11—C3—C5—O4 | −173.11 (11) | C5—C3—C9—C15 | −178.05 (13) |
C9—C3—C5—C10 | 129.61 (13) | C9—C3—C11—C13 | −1.1 (2) |
C11—C3—C5—C10 | −50.23 (16) | C5—C3—C11—C13 | 178.70 (12) |
C9—C3—C5—P1 | −107.20 (13) | C13—C8—N1—O6 | 168.34 (15) |
C11—C3—C5—P1 | 72.95 (14) | C15—C8—N1—O6 | −12.0 (2) |
O1—P1—C5—O4 | 64.33 (10) | C13—C8—N1—O5 | −11.3 (2) |
O2—P1—C5—O4 | −170.16 (8) | C15—C8—N1—O5 | 168.37 (18) |
O3—P1—C5—O4 | −62.00 (10) | C15—C8—C13—C11 | 1.3 (2) |
O1—P1—C5—C3 | −178.91 (9) | N1—C8—C13—C11 | −179.05 (13) |
O2—P1—C5—C3 | −53.40 (10) | C3—C11—C13—C8 | −0.4 (2) |
O3—P1—C5—C3 | 54.76 (10) | C13—C8—C15—C9 | −0.6 (2) |
O1—P1—C5—C10 | −54.94 (11) | N1—C8—C15—C9 | 179.69 (13) |
O2—P1—C5—C10 | 70.57 (10) | C3—C9—C15—C8 | −0.9 (2) |
O3—P1—C5—C10 | 178.73 (9) |
C10H15O4P | F(000) = 488 |
Mr = 230.19 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4780 (3) Å | Cell parameters from 8846 reflections |
b = 17.2370 (6) Å | θ = 4.4–32.3° |
c = 8.1357 (3) Å | µ = 0.23 mm−1 |
β = 106.484 (4)° | T = 173 K |
V = 1140.05 (7) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.35 × 0.25 mm |
Agilent Xcalibur Sapphire3 diffractometer | 3450 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3080 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 30.5°, θmin = 4.3° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −12→12 |
Tmin = 0.933, Tmax = 1.000 | k = −24→24 |
22954 measured reflections | l = −11→11 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.2717P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3450 reflections | Δρmax = 0.35 e Å−3 |
150 parameters | Δρmin = −0.19 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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. An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.81342 (3) | 0.05200 (2) | 0.72375 (3) | 0.01989 (8) | |
O4 | 0.74312 (9) | 0.04889 (5) | 1.01317 (9) | 0.02685 (16) | |
O3 | 0.66366 (9) | 0.00078 (4) | 0.62661 (10) | 0.02942 (17) | |
O2 | 0.81828 (10) | 0.11643 (4) | 0.58901 (9) | 0.02953 (17) | |
C1 | 0.75367 (11) | 0.10611 (5) | 0.89008 (11) | 0.02041 (17) | |
C3 | 0.58302 (11) | 0.14067 (5) | 0.81672 (12) | 0.02116 (17) | |
C2 | 0.88556 (13) | 0.16627 (7) | 0.97005 (14) | 0.0311 (2) | |
H2A | 0.8507 (6) | 0.1966 (5) | 1.0536 (12) | 0.047* | |
H2B | 0.9018 (9) | 0.2002 (5) | 0.8813 (9) | 0.047* | |
H2C | 0.9878 (10) | 0.1401 (3) | 1.0259 (12) | 0.047* | |
C8 | 0.44531 (12) | 0.10121 (6) | 0.83454 (13) | 0.0263 (2) | |
H8 | 0.4588 (2) | 0.0529 (7) | 0.8961 (9) | 0.032* | |
C7 | 0.28845 (13) | 0.13134 (7) | 0.76373 (16) | 0.0346 (2) | |
H7 | 0.1968 (16) | 0.1046 (5) | 0.7770 (3) | 0.042* | |
C6 | 0.26717 (15) | 0.20044 (7) | 0.67392 (17) | 0.0387 (3) | |
H6 | 0.1594 (19) | 0.2211 (4) | 0.6262 (8) | 0.046* | |
C5 | 0.40312 (16) | 0.23950 (7) | 0.65363 (16) | 0.0375 (3) | |
H5 | 0.3892 (3) | 0.2861 (8) | 0.5917 (11) | 0.045* | |
C4 | 0.55997 (14) | 0.20979 (6) | 0.72474 (14) | 0.0300 (2) | |
H4 | 0.6522 (15) | 0.2369 (4) | 0.7105 (3) | 0.036* | |
C10 | 0.64171 (17) | −0.07743 (7) | 0.67685 (18) | 0.0402 (3) | |
H10A | 0.7407 (11) | −0.1029 (3) | 0.7034 (14) | 0.060* | |
H10B | 0.5680 (13) | −0.1025 (3) | 0.5883 (11) | 0.060* | |
H10C | 0.6025 (14) | −0.07680 (7) | 0.7709 (14) | 0.060* | |
C9 | 0.8454 (2) | 0.09599 (9) | 0.42782 (16) | 0.0458 (3) | |
H9A | 0.9519 (13) | 0.0810 (7) | 0.4456 (3) | 0.069* | |
H9B | 0.8243 (14) | 0.1378 (5) | 0.3565 (10) | 0.069* | |
H9C | 0.7773 (13) | 0.0563 (6) | 0.3793 (9) | 0.069* | |
O1 | 0.96698 (9) | 0.00774 (5) | 0.79093 (9) | 0.02834 (16) | |
H1A | 0.834 (2) | 0.0365 (9) | 1.059 (2) | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01892 (12) | 0.02348 (13) | 0.01659 (12) | 0.00242 (8) | 0.00395 (8) | −0.00086 (7) |
O4 | 0.0205 (3) | 0.0382 (4) | 0.0223 (3) | 0.0058 (3) | 0.0068 (3) | 0.0099 (3) |
O3 | 0.0266 (3) | 0.0256 (4) | 0.0292 (4) | 0.0006 (3) | −0.0032 (3) | −0.0042 (3) |
O2 | 0.0403 (4) | 0.0299 (4) | 0.0225 (3) | 0.0049 (3) | 0.0154 (3) | 0.0024 (3) |
C1 | 0.0182 (4) | 0.0251 (4) | 0.0184 (4) | −0.0002 (3) | 0.0060 (3) | −0.0005 (3) |
C3 | 0.0218 (4) | 0.0218 (4) | 0.0202 (4) | 0.0020 (3) | 0.0064 (3) | −0.0010 (3) |
C2 | 0.0264 (5) | 0.0357 (5) | 0.0301 (5) | −0.0071 (4) | 0.0061 (4) | −0.0110 (4) |
C8 | 0.0220 (4) | 0.0273 (5) | 0.0297 (5) | 0.0022 (3) | 0.0077 (4) | 0.0032 (4) |
C7 | 0.0207 (5) | 0.0405 (6) | 0.0416 (6) | 0.0033 (4) | 0.0070 (4) | 0.0007 (5) |
C6 | 0.0316 (5) | 0.0393 (6) | 0.0400 (6) | 0.0145 (5) | 0.0018 (5) | 0.0007 (5) |
C5 | 0.0462 (7) | 0.0269 (5) | 0.0361 (6) | 0.0116 (5) | 0.0065 (5) | 0.0058 (4) |
C4 | 0.0346 (5) | 0.0237 (4) | 0.0325 (5) | 0.0007 (4) | 0.0106 (4) | 0.0031 (4) |
C10 | 0.0422 (6) | 0.0278 (5) | 0.0454 (7) | −0.0065 (5) | 0.0040 (5) | −0.0034 (5) |
C9 | 0.0717 (9) | 0.0474 (7) | 0.0268 (5) | 0.0092 (6) | 0.0277 (6) | 0.0031 (5) |
O1 | 0.0212 (3) | 0.0388 (4) | 0.0240 (3) | 0.0085 (3) | 0.0048 (3) | −0.0004 (3) |
P1—O1 | 1.4738 (7) | C8—C7 | 1.3911 (14) |
P1—O3 | 1.5641 (8) | C8—H8 | 0.962 (14) |
P1—O2 | 1.5692 (8) | C7—C6 | 1.3821 (18) |
P1—C1 | 1.8294 (9) | C7—H7 | 0.936 (16) |
O4—C1 | 1.4265 (11) | C6—C5 | 1.385 (2) |
O4—H1A | 0.787 (16) | C6—H6 | 0.955 (16) |
O3—C10 | 1.4362 (14) | C5—C4 | 1.3887 (16) |
O2—C9 | 1.4381 (13) | C5—H5 | 0.938 (17) |
C1—C3 | 1.5212 (13) | C4—H4 | 0.946 (15) |
C1—C2 | 1.5284 (13) | C10—H10A | 0.917 (10) |
C3—C4 | 1.3910 (14) | C10—H10B | 0.917 (10) |
C3—C8 | 1.3938 (13) | C10—H10C | 0.917 (10) |
C2—H2A | 0.968 (9) | C9—H9A | 0.910 (11) |
C2—H2B | 0.968 (9) | C9—H9B | 0.910 (11) |
C2—H2C | 0.968 (9) | C9—H9C | 0.910 (11) |
O1—P1—O3 | 113.59 (5) | C3—C8—H8 | 119.8 |
O1—P1—O2 | 115.46 (4) | C6—C7—C8 | 120.44 (11) |
O3—P1—O2 | 103.00 (4) | C6—C7—H7 | 119.8 |
O1—P1—C1 | 112.98 (4) | C8—C7—H7 | 119.8 |
O3—P1—C1 | 107.82 (4) | C7—C6—C5 | 119.60 (11) |
O2—P1—C1 | 102.92 (4) | C7—C6—H6 | 120.2 |
C1—O4—H1A | 105.5 (11) | C5—C6—H6 | 120.2 |
C10—O3—P1 | 122.56 (7) | C6—C5—C4 | 120.14 (11) |
C9—O2—P1 | 120.42 (8) | C6—C5—H5 | 119.9 |
O4—C1—C3 | 107.70 (7) | C4—C5—H5 | 119.9 |
O4—C1—C2 | 110.75 (8) | C5—C4—C3 | 120.78 (10) |
C3—C1—C2 | 113.63 (8) | C5—C4—H4 | 119.6 |
O4—C1—P1 | 104.62 (6) | C3—C4—H4 | 119.6 |
C3—C1—P1 | 109.97 (6) | O3—C10—H10A | 109.5 |
C2—C1—P1 | 109.76 (7) | O3—C10—H10B | 109.5 |
C4—C3—C8 | 118.68 (9) | H10A—C10—H10B | 109.5 |
C4—C3—C1 | 121.28 (9) | O3—C10—H10C | 109.5 |
C8—C3—C1 | 119.97 (8) | H10A—C10—H10C | 109.5 |
C1—C2—H2A | 109.5 | H10B—C10—H10C | 109.5 |
C1—C2—H2B | 109.5 | O2—C9—H9A | 109.5 |
H2A—C2—H2B | 109.5 | O2—C9—H9B | 109.5 |
C1—C2—H2C | 109.5 | H9A—C9—H9B | 109.5 |
H2A—C2—H2C | 109.5 | O2—C9—H9C | 109.5 |
H2B—C2—H2C | 109.5 | H9A—C9—H9C | 109.5 |
C7—C8—C3 | 120.35 (10) | H9B—C9—H9C | 109.5 |
C7—C8—H8 | 119.8 | ||
O1—P1—O3—C10 | 34.73 (11) | O4—C1—C3—C4 | 164.60 (9) |
O2—P1—O3—C10 | 160.34 (9) | C2—C1—C3—C4 | 41.53 (12) |
C1—P1—O3—C10 | −91.28 (10) | P1—C1—C3—C4 | −81.95 (10) |
O1—P1—O2—C9 | 62.50 (11) | O4—C1—C3—C8 | −18.28 (11) |
O3—P1—O2—C9 | −61.89 (10) | C2—C1—C3—C8 | −141.34 (9) |
C1—P1—O2—C9 | −173.93 (10) | P1—C1—C3—C8 | 95.17 (9) |
O1—P1—C1—O4 | −56.46 (7) | C4—C3—C8—C7 | −1.01 (15) |
O3—P1—C1—O4 | 69.91 (6) | C1—C3—C8—C7 | −178.21 (9) |
O2—P1—C1—O4 | 178.34 (6) | C3—C8—C7—C6 | 0.44 (17) |
O1—P1—C1—C3 | −171.88 (6) | C8—C7—C6—C5 | 0.42 (19) |
O3—P1—C1—C3 | −45.51 (7) | C7—C6—C5—C4 | −0.70 (19) |
O2—P1—C1—C3 | 62.92 (7) | C6—C5—C4—C3 | 0.12 (18) |
O1—P1—C1—C2 | 62.41 (8) | C8—C3—C4—C5 | 0.73 (15) |
O3—P1—C1—C2 | −171.22 (7) | C1—C3—C4—C5 | 177.90 (10) |
O2—P1—C1—C2 | −62.79 (8) |
C11H17O6P | F(000) = 1168 |
Mr = 276.21 | Dx = 1.388 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 39.464 (3) Å | Cell parameters from 2697 reflections |
b = 8.5132 (4) Å | θ = 4.9–30.5° |
c = 8.0044 (3) Å | µ = 0.23 mm−1 |
β = 100.620 (5)° | T = 173 K |
V = 2643.2 (2) Å3 | Block, colorless |
Z = 8 | 0.30 × 0.20 × 0.05 mm |
Agilent Xcalibur Sapphire3 diffractometer | 4023 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2812 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.049 |
ω scans | θmax = 30.5°, θmin = 4.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −56→52 |
Tmin = 0.956, Tmax = 1.000 | k = −9→12 |
13696 measured reflections | l = −8→11 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0536P)2 + 1.0539P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
4023 reflections | Δρmax = 0.40 e Å−3 |
178 parameters | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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. An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.56049 (2) | 0.22453 (5) | 0.55325 (5) | 0.02391 (13) | |
O5 | 0.69582 (3) | 0.23316 (15) | 0.89486 (15) | 0.0296 (3) | |
O3 | 0.56238 (3) | 0.39780 (15) | 0.48490 (15) | 0.0307 (3) | |
O2 | 0.52552 (3) | 0.16331 (17) | 0.44805 (17) | 0.0345 (3) | |
C1 | 0.59193 (5) | 0.1112 (2) | 0.4634 (2) | 0.0250 (3) | |
H1 | 0.58536 (13) | 0.1140 (2) | 0.334 (2) | 0.030* | |
O6 | 0.72468 (3) | 0.37616 (17) | 0.67767 (17) | 0.0361 (3) | |
C5 | 0.69270 (5) | 0.3178 (2) | 0.6143 (2) | 0.0263 (4) | |
C2 | 0.62749 (4) | 0.1814 (2) | 0.5161 (2) | 0.0240 (3) | |
O4 | 0.59076 (4) | −0.04869 (15) | 0.51955 (17) | 0.0326 (3) | |
C6 | 0.67557 (5) | 0.3291 (2) | 0.4488 (2) | 0.0309 (4) | |
H6 | 0.6857 (2) | 0.3837 (13) | 0.3684 (18) | 0.037* | |
C4 | 0.67689 (5) | 0.23697 (19) | 0.7345 (2) | 0.0235 (3) | |
C7 | 0.64311 (5) | 0.2601 (2) | 0.3991 (2) | 0.0280 (4) | |
H7 | 0.6329 (3) | 0.2664 (3) | 0.296 (3) | 0.034* | |
C3 | 0.64461 (4) | 0.1704 (2) | 0.6854 (2) | 0.0229 (3) | |
H3 | 0.6339 (2) | 0.1161 (11) | 0.7680 (17) | 0.028* | |
C11 | 0.49302 (6) | 0.2215 (3) | 0.4808 (3) | 0.0526 (6) | |
H11A | 0.4912 (2) | 0.200 (2) | 0.592 (2) | 0.079* | |
H11B | 0.4751 (3) | 0.1731 (18) | 0.408 (2) | 0.079* | |
H11C | 0.4918 (2) | 0.3290 (18) | 0.463 (2) | 0.079* | |
C10 | 0.58384 (6) | 0.5159 (2) | 0.5824 (3) | 0.0385 (5) | |
H10A | 0.5758 (3) | 0.5353 (13) | 0.6871 (17) | 0.058* | |
H10B | 0.5827 (3) | 0.6118 (15) | 0.5174 (11) | 0.058* | |
H10C | 0.6074 (3) | 0.4793 (9) | 0.6075 (16) | 0.058* | |
C9 | 0.74214 (5) | 0.4591 (3) | 0.5627 (3) | 0.0408 (5) | |
H9A | 0.7451 (4) | 0.3913 (11) | 0.4715 (17) | 0.061* | |
H9B | 0.7642 (4) | 0.4929 (17) | 0.6217 (10) | 0.061* | |
H9C | 0.7288 (3) | 0.5483 (16) | 0.5184 (17) | 0.061* | |
C8 | 0.68164 (6) | 0.1518 (3) | 1.0207 (2) | 0.0416 (5) | |
H8A | 0.6591 (4) | 0.1996 (13) | 1.0309 (14) | 0.062* | |
H8B | 0.6977 (3) | 0.1593 (16) | 1.1319 (16) | 0.062* | |
H8C | 0.6782 (4) | 0.0395 (16) | 0.9877 (11) | 0.062* | |
O1 | 0.56403 (3) | 0.21578 (15) | 0.73921 (16) | 0.0307 (3) | |
H1A | 0.5808 (6) | −0.101 (3) | 0.434 (3) | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0241 (2) | 0.0244 (2) | 0.0232 (2) | 0.00164 (18) | 0.00415 (16) | 0.00097 (17) |
O5 | 0.0308 (7) | 0.0330 (7) | 0.0233 (6) | −0.0076 (6) | 0.0009 (5) | 0.0031 (5) |
O3 | 0.0371 (7) | 0.0265 (6) | 0.0277 (6) | 0.0023 (6) | 0.0042 (5) | 0.0041 (5) |
O2 | 0.0236 (6) | 0.0410 (8) | 0.0383 (7) | −0.0003 (6) | 0.0043 (6) | −0.0048 (6) |
C1 | 0.0261 (8) | 0.0247 (8) | 0.0236 (8) | 0.0011 (7) | 0.0034 (7) | −0.0020 (6) |
O6 | 0.0300 (7) | 0.0413 (8) | 0.0373 (7) | −0.0113 (6) | 0.0071 (6) | 0.0067 (6) |
C5 | 0.0259 (8) | 0.0237 (8) | 0.0302 (9) | −0.0010 (7) | 0.0078 (7) | 0.0013 (7) |
C2 | 0.0236 (8) | 0.0238 (8) | 0.0249 (8) | 0.0029 (7) | 0.0054 (6) | −0.0031 (6) |
O4 | 0.0377 (8) | 0.0238 (6) | 0.0343 (7) | −0.0005 (6) | 0.0010 (6) | −0.0050 (5) |
C6 | 0.0328 (10) | 0.0323 (9) | 0.0299 (9) | 0.0021 (8) | 0.0114 (8) | 0.0065 (8) |
C4 | 0.0269 (8) | 0.0208 (7) | 0.0233 (8) | 0.0007 (7) | 0.0057 (6) | −0.0004 (6) |
C7 | 0.0282 (9) | 0.0344 (10) | 0.0216 (8) | 0.0045 (8) | 0.0049 (7) | 0.0015 (7) |
C3 | 0.0248 (8) | 0.0214 (7) | 0.0237 (8) | 0.0006 (7) | 0.0075 (7) | −0.0003 (6) |
C11 | 0.0258 (10) | 0.0718 (17) | 0.0603 (15) | 0.0026 (11) | 0.0086 (10) | −0.0110 (12) |
C10 | 0.0515 (12) | 0.0224 (9) | 0.0418 (11) | −0.0006 (9) | 0.0089 (10) | −0.0023 (8) |
C9 | 0.0329 (10) | 0.0377 (11) | 0.0538 (12) | −0.0058 (9) | 0.0131 (9) | 0.0176 (10) |
C8 | 0.0386 (11) | 0.0609 (14) | 0.0251 (9) | −0.0103 (10) | 0.0053 (8) | 0.0068 (9) |
O1 | 0.0356 (7) | 0.0311 (7) | 0.0267 (6) | 0.0046 (6) | 0.0088 (5) | 0.0039 (5) |
P1—O1 | 1.4711 (13) | C6—C7 | 1.399 (3) |
P1—O2 | 1.5676 (14) | C6—H6 | 0.94 (2) |
P1—O3 | 1.5797 (13) | C4—C3 | 1.383 (2) |
P1—C1 | 1.8213 (18) | C7—H7 | 0.85 (2) |
O5—C4 | 1.362 (2) | C3—H3 | 0.967 (19) |
O5—C8 | 1.420 (2) | C11—H11A | 0.926 (15) |
O3—C10 | 1.447 (2) | C11—H11B | 0.926 (15) |
O2—C11 | 1.443 (2) | C11—H11C | 0.926 (15) |
C1—O4 | 1.437 (2) | C10—H10A | 0.965 (13) |
C1—C2 | 1.512 (2) | C10—H10B | 0.965 (13) |
C1—H1 | 1.018 (19) | C10—H10C | 0.965 (13) |
O6—C5 | 1.364 (2) | C9—H9A | 0.954 (13) |
O6—C9 | 1.433 (2) | C9—H9B | 0.954 (14) |
C5—C6 | 1.375 (3) | C9—H9C | 0.954 (13) |
C5—C4 | 1.417 (2) | C8—H8A | 0.995 (13) |
C2—C7 | 1.385 (2) | C8—H8B | 0.995 (13) |
C2—C3 | 1.401 (2) | C8—H8C | 0.995 (13) |
O4—H1A | 0.85 (2) | ||
O1—P1—O2 | 115.90 (8) | C2—C7—H7 | 119.7 |
O1—P1—O3 | 113.32 (7) | C6—C7—H7 | 119.7 |
O2—P1—O3 | 102.56 (8) | C4—C3—C2 | 120.14 (15) |
O1—P1—C1 | 115.36 (8) | C4—C3—H3 | 119.9 |
O2—P1—C1 | 102.01 (8) | C2—C3—H3 | 119.9 |
O3—P1—C1 | 106.20 (8) | O2—C11—H11A | 109.5 |
C4—O5—C8 | 117.46 (14) | O2—C11—H11B | 109.5 |
C10—O3—P1 | 121.49 (12) | H11A—C11—H11B | 109.5 |
C11—O2—P1 | 120.82 (14) | O2—C11—H11C | 109.5 |
O4—C1—C2 | 111.66 (14) | H11A—C11—H11C | 109.5 |
O4—C1—P1 | 108.34 (11) | H11B—C11—H11C | 109.5 |
C2—C1—P1 | 110.16 (11) | O3—C10—H10A | 109.5 |
O4—C1—H1 | 108.9 | O3—C10—H10B | 109.5 |
C2—C1—H1 | 108.9 | H10A—C10—H10B | 109.5 |
P1—C1—H1 | 108.9 | O3—C10—H10C | 109.5 |
C5—O6—C9 | 117.53 (15) | H10A—C10—H10C | 109.5 |
O6—C5—C6 | 126.12 (16) | H10B—C10—H10C | 109.5 |
O6—C5—C4 | 114.67 (16) | O6—C9—H9A | 109.5 |
C6—C5—C4 | 119.21 (17) | O6—C9—H9B | 109.5 |
C7—C2—C3 | 119.39 (16) | H9A—C9—H9B | 109.5 |
C7—C2—C1 | 120.54 (16) | O6—C9—H9C | 109.5 |
C3—C2—C1 | 120.05 (15) | H9A—C9—H9C | 109.5 |
C1—O4—H1A | 106.1 (15) | H9B—C9—H9C | 109.5 |
C5—C6—C7 | 120.41 (17) | O5—C8—H8A | 109.5 |
C5—C6—H6 | 119.8 | O5—C8—H8B | 109.5 |
C7—C6—H6 | 119.8 | H8A—C8—H8B | 109.5 |
O5—C4—C3 | 125.08 (15) | O5—C8—H8C | 109.5 |
O5—C4—C5 | 114.69 (15) | H8A—C8—H8C | 109.5 |
C3—C4—C5 | 120.23 (16) | H8B—C8—H8C | 109.5 |
C2—C7—C6 | 120.61 (17) | ||
O1—P1—O3—C10 | 33.33 (16) | P1—C1—C2—C3 | 70.10 (18) |
O2—P1—O3—C10 | 159.02 (14) | O6—C5—C6—C7 | 178.26 (17) |
C1—P1—O3—C10 | −94.32 (15) | C4—C5—C6—C7 | −0.8 (3) |
O1—P1—O2—C11 | 52.68 (19) | C8—O5—C4—C3 | 1.3 (3) |
O3—P1—O2—C11 | −71.31 (18) | C8—O5—C4—C5 | −179.03 (17) |
C1—P1—O2—C11 | 178.83 (17) | O6—C5—C4—O5 | 1.2 (2) |
O1—P1—C1—O4 | 54.60 (14) | C6—C5—C4—O5 | −179.60 (16) |
O2—P1—C1—O4 | −71.91 (13) | O6—C5—C4—C3 | −179.11 (15) |
O3—P1—C1—O4 | −178.97 (11) | C6—C5—C4—C3 | 0.0 (3) |
O1—P1—C1—C2 | −67.82 (14) | C3—C2—C7—C6 | −0.5 (3) |
O2—P1—C1—C2 | 165.67 (12) | C1—C2—C7—C6 | 178.12 (16) |
O3—P1—C1—C2 | 58.62 (13) | C5—C6—C7—C2 | 1.0 (3) |
C9—O6—C5—C6 | 0.8 (3) | O5—C4—C3—C2 | −179.91 (16) |
C9—O6—C5—C4 | 179.93 (16) | C5—C4—C3—C2 | 0.5 (3) |
O4—C1—C2—C7 | 131.07 (17) | C7—C2—C3—C4 | −0.3 (3) |
P1—C1—C2—C7 | −108.49 (16) | C1—C2—C3—C4 | −178.88 (15) |
O4—C1—C2—C3 | −50.3 (2) |
C9H13O4P | F(000) = 456 |
Mr = 216.16 | Dx = 1.354 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4039 (5) Å | Cell parameters from 4166 reflections |
b = 7.7007 (3) Å | θ = 4.6–30.9° |
c = 16.6012 (7) Å | µ = 0.25 mm−1 |
β = 99.149 (4)° | T = 173 K |
V = 1060.69 (9) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.20 × 0.04 mm |
Agilent Xcalibur Sapphire3 diffractometer | 3209 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2491 reflections with I > 2σ(I) |
Detector resolution: 15.9809 pixels mm-1 | Rint = 0.041 |
ω scans | θmax = 30.5°, θmin = 4.1° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −12→12 |
Tmin = 0.846, Tmax = 1.000 | k = −10→10 |
20344 measured reflections | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.2064P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3209 reflections | Δρmax = 0.33 e Å−3 |
139 parameters | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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. An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F2 using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.88836 (4) | 0.22015 (5) | 0.36890 (2) | 0.02690 (11) | |
O4 | 0.69794 (12) | 0.26302 (13) | 0.23287 (6) | 0.0324 (2) | |
O2 | 0.74859 (13) | 0.27837 (13) | 0.41599 (6) | 0.0360 (2) | |
O1 | 0.90892 (11) | 0.03033 (13) | 0.36664 (5) | 0.0307 (2) | |
O3 | 1.03594 (13) | 0.32532 (14) | 0.41315 (6) | 0.0371 (2) | |
C1 | 0.85171 (16) | 0.32552 (17) | 0.26993 (8) | 0.0278 (3) | |
H1 | 0.8441 (2) | 0.451 (2) | 0.27822 (17) | 0.033* | |
C2 | 0.98395 (16) | 0.29140 (17) | 0.22002 (8) | 0.0278 (3) | |
C3 | 0.97089 (19) | 0.1600 (2) | 0.16223 (8) | 0.0349 (3) | |
H3 | 0.8787 (18) | 0.0862 (14) | 0.15465 (17) | 0.042* | |
C8 | 0.6006 (2) | 0.1790 (2) | 0.40829 (11) | 0.0458 (4) | |
H8A | 0.5292 | 0.2134 | 0.3583 | 0.069* | |
H8B | 0.5471 | 0.2013 | 0.4556 | 0.069* | |
H8C | 0.6254 | 0.0549 | 0.4058 | 0.069* | |
C4 | 1.0920 (2) | 0.1360 (3) | 0.11544 (10) | 0.0473 (4) | |
H4 | 1.0819 (3) | 0.047 (2) | 0.0756 (9) | 0.057* | |
C7 | 1.12124 (19) | 0.3953 (2) | 0.23104 (10) | 0.0408 (3) | |
H7 | 1.1322 (3) | 0.4860 (19) | 0.2714 (8) | 0.049* | |
C9 | 1.1277 (2) | 0.2684 (3) | 0.48861 (11) | 0.0541 (5) | |
H9A | 1.0634 (10) | 0.2545 (19) | 0.5249 (6) | 0.081* | |
H9B | 1.2013 (16) | 0.3464 (15) | 0.5061 (6) | 0.081* | |
H9C | 1.1747 (16) | 0.1692 (18) | 0.4810 (2) | 0.081* | |
C6 | 1.2420 (2) | 0.3695 (3) | 0.18461 (11) | 0.0515 (5) | |
H6 | 1.333 (2) | 0.4388 (17) | 0.1927 (2) | 0.062* | |
C5 | 1.2269 (2) | 0.2405 (3) | 0.12611 (11) | 0.0523 (5) | |
H5 | 1.313 (2) | 0.2229 (5) | 0.0918 (8) | 0.063* | |
H1A | 0.653 (3) | 0.334 (3) | 0.1967 (13) | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.03003 (18) | 0.02395 (17) | 0.02590 (17) | −0.00095 (12) | 0.00192 (12) | −0.00101 (12) |
O4 | 0.0263 (5) | 0.0321 (5) | 0.0364 (5) | −0.0014 (4) | −0.0027 (4) | 0.0061 (4) |
O2 | 0.0401 (6) | 0.0332 (5) | 0.0364 (5) | −0.0027 (4) | 0.0116 (4) | −0.0085 (4) |
O1 | 0.0361 (5) | 0.0253 (5) | 0.0297 (5) | 0.0015 (4) | 0.0020 (4) | 0.0011 (4) |
O3 | 0.0405 (6) | 0.0364 (5) | 0.0310 (5) | −0.0091 (4) | −0.0049 (4) | 0.0013 (4) |
C1 | 0.0286 (6) | 0.0221 (6) | 0.0310 (6) | −0.0013 (5) | −0.0005 (5) | 0.0013 (5) |
C2 | 0.0288 (6) | 0.0267 (6) | 0.0261 (6) | −0.0014 (5) | −0.0010 (5) | 0.0071 (5) |
C3 | 0.0392 (8) | 0.0368 (7) | 0.0285 (6) | −0.0040 (6) | 0.0046 (5) | 0.0017 (5) |
C8 | 0.0396 (8) | 0.0516 (10) | 0.0493 (9) | −0.0081 (7) | 0.0172 (7) | −0.0115 (7) |
C4 | 0.0526 (10) | 0.0572 (11) | 0.0341 (8) | 0.0033 (8) | 0.0129 (7) | 0.0006 (7) |
C7 | 0.0357 (8) | 0.0413 (8) | 0.0434 (8) | −0.0100 (6) | 0.0001 (6) | 0.0031 (7) |
C9 | 0.0508 (10) | 0.0636 (12) | 0.0408 (9) | −0.0117 (9) | −0.0145 (8) | 0.0096 (8) |
C6 | 0.0335 (8) | 0.0672 (12) | 0.0531 (10) | −0.0107 (8) | 0.0050 (7) | 0.0173 (9) |
C5 | 0.0421 (9) | 0.0774 (13) | 0.0404 (8) | 0.0057 (9) | 0.0159 (7) | 0.0189 (9) |
P1—O1 | 1.4731 (10) | C8—H8A | 0.9800 |
P1—O3 | 1.5633 (10) | C8—H8B | 0.9800 |
P1—O2 | 1.5760 (11) | C8—H8C | 0.9800 |
P1—C1 | 1.8144 (14) | C4—C5 | 1.378 (3) |
O4—C1 | 1.4238 (16) | C4—H4 | 0.95 (2) |
O4—H1A | 0.85 (2) | C7—C6 | 1.383 (2) |
O2—C8 | 1.4485 (19) | C7—H7 | 0.962 (19) |
O3—C9 | 1.4315 (19) | C9—H9A | 0.878 (13) |
C1—C2 | 1.5111 (19) | C9—H9B | 0.878 (13) |
C1—H1 | 0.977 (17) | C9—H9C | 0.878 (13) |
C2—C3 | 1.386 (2) | C6—C5 | 1.381 (3) |
C2—C7 | 1.3918 (19) | C6—H6 | 0.92 (2) |
C3—C4 | 1.388 (2) | C5—H5 | 1.00 (2) |
C3—H3 | 0.953 (18) | ||
O1—P1—O3 | 116.01 (6) | H8A—C8—H8B | 109.5 |
O1—P1—O2 | 113.24 (6) | O2—C8—H8C | 109.5 |
O3—P1—O2 | 102.58 (6) | H8A—C8—H8C | 109.5 |
O1—P1—C1 | 115.11 (6) | H8B—C8—H8C | 109.5 |
O3—P1—C1 | 101.63 (6) | C5—C4—C3 | 120.78 (17) |
O2—P1—C1 | 106.82 (6) | C5—C4—H4 | 119.6 |
C1—O4—H1A | 110.7 (15) | C3—C4—H4 | 119.6 |
C8—O2—P1 | 120.21 (10) | C6—C7—C2 | 120.72 (16) |
C9—O3—P1 | 121.95 (10) | C6—C7—H7 | 119.6 |
O4—C1—C2 | 113.60 (11) | C2—C7—H7 | 119.6 |
O4—C1—P1 | 104.58 (9) | O3—C9—H9A | 109.5 |
C2—C1—P1 | 112.65 (9) | O3—C9—H9B | 109.5 |
O4—C1—H1 | 108.6 | H9A—C9—H9B | 109.5 |
C2—C1—H1 | 108.6 | O3—C9—H9C | 109.5 |
P1—C1—H1 | 108.6 | H9A—C9—H9C | 109.5 |
C3—C2—C7 | 118.89 (14) | H9B—C9—H9C | 109.5 |
C3—C2—C1 | 121.47 (12) | C5—C6—C7 | 120.09 (17) |
C7—C2—C1 | 119.63 (13) | C5—C6—H6 | 120.0 |
C2—C3—C4 | 120.01 (15) | C7—C6—H6 | 120.0 |
C2—C3—H3 | 120.0 | C4—C5—C6 | 119.50 (17) |
C4—C3—H3 | 120.0 | C4—C5—H5 | 120.2 |
O2—C8—H8A | 109.5 | C6—C5—H5 | 120.2 |
O2—C8—H8B | 109.5 | ||
O1—P1—O2—C8 | −38.37 (13) | O4—C1—C2—C3 | −22.67 (17) |
O3—P1—O2—C8 | −164.16 (12) | P1—C1—C2—C3 | 96.02 (13) |
C1—P1—O2—C8 | 89.38 (13) | O4—C1—C2—C7 | 156.34 (12) |
O1—P1—O3—C9 | −42.43 (15) | P1—C1—C2—C7 | −84.97 (14) |
O2—P1—O3—C9 | 81.54 (14) | C7—C2—C3—C4 | −1.3 (2) |
C1—P1—O3—C9 | −168.06 (14) | C1—C2—C3—C4 | 177.76 (13) |
O1—P1—C1—O4 | 66.37 (10) | C2—C3—C4—C5 | 0.6 (2) |
O3—P1—C1—O4 | −167.41 (9) | C3—C2—C7—C6 | 0.7 (2) |
O2—P1—C1—O4 | −60.28 (10) | C1—C2—C7—C6 | −178.31 (14) |
O1—P1—C1—C2 | −57.47 (11) | C2—C7—C6—C5 | 0.5 (3) |
O3—P1—C1—C2 | 68.76 (10) | C3—C4—C5—C6 | 0.6 (3) |
O2—P1—C1—C2 | 175.88 (9) | C7—C6—C5—C4 | −1.1 (3) |
Product | Time (min) | Yield (%) | δP | δP (reference) | M.p. (°C) | M.p. (reference) (°C) | [M + H]+ | Entry |
1a | 10 | 95 | 23.8 | 24.3a | 100–101 | 101–102e,f | 217.1g | 1 |
1b | 120 | 86 | 24.1 | 23.8b | 125–126 | 124b | 277.1g | 2# |
3a | 30 | 91 | 21.1 | 21.1c | 124–125 | - | 414.1114c | 3 |
3b | 30 | 88 | 22.3 | 22.3c | 103–104 | - | 403.0881c | 4 |
3c | 330 | 94 | 22.4 | 22.4d | 110–111 | 87–88d | 383.1392c | 5 |
Notes: (#) In this case, 0.3 equivalents of triethylamine was used. References: (a) Rowe & Spilling (2001); (b) Hudson et al. (2008); (c) Rádai et al. (2018); (d) Pawar et al. (2006); (e) Keglevich et al. (2011); (f) Abramov (1952); (g) Keglevich et al. (2017). |
Product | Time (h) | Yield (%) | δP | δP (literature) | M.p. (°C) | M.p. (literature) (°C) | [M + H]+ | Entry |
2a | 7 | 48 | 26.2 | 26.0a | 130–131 | 130c | 231.1b | 1 |
2b | 2 | 82 | 24.8 | 24.8b | 167–168 | 170–171b | 276.1b | 2# |
Notes: (#) 13C NMR (CDCl3): δ 25.8 (d, 2J = 3.3 Hz, CH3), 53.8 (d, 2J = 8.0 Hz, OCH3), 54.7 (d, 2J = 7.3 Hz, OCH3), 73.7 (d, 1J = 160.1 Hz, PCH), 123.1 (d, 4J = 2.7 Hz, C3), 126.8 (d, 3J = 4.2 Hz, C2), 147.2 (d, 5J = 3.3 Hz, C4), 148.6 (C1). References: (a) Seven et al. (2011); (b) Keglevich et al. (2017); (c) Hudson et al. (2008). |
Compound | Solvent | Precipitant | Crystallization time |
1aa | methanol | pentane | 5 min |
1bb | acetone | – | 48 h |
2ab | acetone | – | 48 h |
2bb | acetone | – | 48 h |
3ab | diethyl ether | – | 24 h |
3bb | diethyl ether | – | 24 h |
3cb | diethyl ether | – | 72 h |
Notes: (a) crystals were obtained from the reaction mixture; (b) crystals were obtained by recrystallization. |
Compound 3a has two independent molecules in the asymmetric unit hence the two values. |
Compound | OPCO | Torsion (°) |
1a | O1 P1 C1 O4 | 66.4 (1) |
1b | O1 P1 C1 O4 | 54.6 (1) |
2a | O1 P1 C1 O4 | -56.5 (1) |
2b | O1 P1 C5 O4 | 64.3 (1) |
3a | O1 P1 C1 O4 | -74.0 (1) |
3a | O7 P2 C22 O10 | 73.5 (1) |
3b | O1 P1 C1 O4 | 55.5 (3) |
3c | O1 P1 C1 O4 | 55.4 (2) |
Extracted from a full table and rounded appropriately to integer numbers. The most relevant numbers are printed in bold. |
Count | Min (°) | Max (°) | Mean (°) | Sample std dev. (°) | Mean std dev. (°) | Skewness | Kurtosis | Median (°) | |
OPCO | 36 | 48 | 83 | 64 | 9 | 7 | 0.56 | -0.49 | 61 |
35 crystal structures yielded 42 independent fragments containing the search moiety (the table is restricted to the most known parameters only). AHD is the P═O···H—O hydrogen-bridge angle and d is the O···H distance. The angular values are rounded to whole degrees. |
Name | Count | Min. | Max. | Mean | Sample std dev. | Mean dev. | Median |
AHD (°) | 42 | 136 | 178 | 166 | 11 | 9 | 170 |
d (Å) | 42 | 2.59 | 2.77 | 2.70 | 0.04 | 0.03 | 2.70 |
Primary contacts are O—H···O hydrogen-bond bridges, while secondary contacts accomplish additional C—H···O hydrogen-bond bridges involving those used in the primary contact as well (for a graphical overview, see Table ST2 in the supporting information) |
Compound | Primary GS | Secondary GS |
1a | C(5) | R22(8) |
1b | C(5) | R22(8) |
2a | R22(10) | R22(10) |
2b | R22(10) | R22(10) |
3a | R22(10) | R22(10), with S(6) and S(5) |
3b | C(5) | R22(8) |
3c | C(5) | C(8), C22(13), with S(7) |