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The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C
9H
13O
4P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C
11H
17O
6P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C
10H
15O
4P, dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate, C
10H
14NO
6P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C
21H
20NO
6P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C
21H
20ClO
4P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, C
22H
23O
4P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C—OH
O=P chain-linked packing and the dimeric types of hydrogen-bond bridges of intermolecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper (
i.e. secondary graph sets of the C—H
O type) revealed a similarity in the graph-set descriptors, suggesting a fine interplay of substituent- and shape-dependent effects on strong–weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary Cα atom, but also by the nature and crowding of the
ortho substituents of the α-aryl group.
Supporting information
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).
Dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate (3c)
top
Crystal data top
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 | |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate (3b)
top
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate (3a)
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate (2b)
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Dimethyl (1-hydroxy-1-phenylethyl)phosphonate (2a)
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate (1b)
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Dimethyl [(hydroxy)(phenyl)methyl]phosphonate (1a)
top
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Experimental details for the preparation and characterization of
α-hydroxyphosphonates 1 and 3 topProduct | 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). |
Experimental details for the preparation and characterization of
α-hydroxyphosphonates 2a and 2b. topProduct | 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). |
Crystallization summary of compounds 1, 2 and 3 at 26 °C topCompound | 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. |
OPCO torsion angles in 1a–3c with their standard deviations
in parentheses topCompound 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) |
Statistic descriptors of the 36 OPCO values around the sc conformation range in
the CSD topExtracted 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 |
Hydrogen-bridge statistics table of the intermolecular hydrogen bridges of
acyclic esters of hydroxyphosphonate fragments in the CSD top35 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 |
Hydrogen-bond graph-set descriptors in compounds 1a–3c topPrimary 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) |
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