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The structures of six cyclic oxazaphospholidines and three cyclic oxazaphosphinanes have been determined and their supramolecular structures have been compared. The molecules differ with respect to the functional groups attached to the central five- or six-membered rings, but have one phosphoryl group in common. The predominant feature in the supramolecular structures is the existence of relatively weak intermolecular phosphoryl XH...O=P (X = C, N) hydrogen bonds, creating in nearly all cases linear zigzag or double molecular chains. The molecular chains are in general linked to each other via very weak CH...π or usual hydrogen-bond interactions. A survey of the Cambridge Structural Database on similar XH...O=P interactions shows a very large flexibility of the XH...O angle, which is in agreement with the DFT calculation reported elsewhere. The strength of the XH...O=P interaction can therefore be considered as relatively weak to moderately strong, and is expected to play at least a role in the formation of secondary substructures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107061770/gp5020sup1.cif
Contains datablocks I, II, III, IV, V, VI, VII, VIII, IX

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020IIsup3.hkl
Contains datablock CRYSTALS_cif

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020IIIsup4.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020IVsup5.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020VIsup7.hkl
Contains datablock CRYSTALS_cif

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020VIIsup8.hkl
Contains datablock CRYSTALS_cif

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020VIIIsup9.hkl
Contains datablock CRYSTALS_cif

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107061770/gp5020IXsup10.hkl
Contains datablock CRYSTALS_cif

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768107061770/gp5020sup11.pdf
Supplementary material

CCDC references: 685139; 685140; 685141; 685142; 685143; 685144; 685145; 685146; 685147

Comment top

P-chiral organophosphorous compounds are used as ligands in catalysts for asymmetric organic synthesis and they are also functional as antibiotics, antitumorals and fungicides. We synthesized

Refinement top

In the absence of significant anomalous scattering, Friedel pairs were merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090–1098.

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, N—H in the range 0.86–0.89 N—H to 0.86 O—H = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Computing details top

Data collection: SMART (Siemens, 1993) for (I), (II); P3/PC. (Siemens,1993) for (III), (IV); Enraf-Nonius (1989) for (V), (VI); CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) for (VII); CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (VIII), (IX). Cell refinement: SAINT (Siemens ,1995) for (I), (II); P3/PC. (Siemens,1993) for (III), (IV); Enraf-Nonius (1989) for (V), (VI); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) for (VII); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (VIII), (IX). Data reduction: SAINT (Siemens ,1995) for (I), (II); P3/PC. (Siemens,1993) for (III), (IV); XCAD4 (Harms, K. \& Wocadlo, S., 1995) for (V), (VI); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) for (VII); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (VIII), (IX). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (I), (III), (IV), (V), (VI); SIR2002 (Burla et al., 2003) for (II), (VII), (IX); Superflip (Palatinus, 2006) for (VIII). For all compounds, program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
[Figure 13]
[Figure 14]
[Figure 15]
[Figure 16]
Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
(I) (2R,4S,5R)-3-tert-butyl-2-ethyl-4,5-diphenyl- [1,3,2]-oxazaphospholidine2-oxide top
Crystal data top
C20H26NO2PF(000) = 1472
Mr = 343.39Dx = 1.215 Mg m3
Orthorhombic, PbcaSynchrotron radiation, λ = 0.50606 Å
Hall symbol: -P 2ac 2abCell parameters from 9727 reflections
a = 10.5381 (8) Åθ = 2.5–15.5°
b = 15.7519 (14) ŵ = 0.07 mm1
c = 22.626 (2) ÅT = 120 K
V = 3755.8 (6) Å3Needle, translucent pale white
Z = 80.50 × 0.05 × 0.05 mm
Data collection top
Bruker SMART
diffractometer
4671 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.072
ω scansθmax = 20.8°, θmin = 1.2°
Absorption correction: multi-scan
SADABS (Siemens, 1996)
h = 1514
Tmin = 0.89, Tmax = 1.00k = 1922
22025 measured reflectionsl = 3133
6228 independent reflections
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.052 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.490 0.521 0.215
wR(F2) = 0.052(Δ/σ)max = 0.001
S = 0.99Δρmax = 0.36 e Å3
4671 reflectionsΔρmin = 0.67 e Å3
218 parametersExtinction correction: Larson (1970), Equation 22
0 restraintsExtinction coefficient: 8606.704
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H26NO2PV = 3755.8 (6) Å3
Mr = 343.39Z = 8
Orthorhombic, PbcaSynchrotron radiation, λ = 0.50606 Å
a = 10.5381 (8) ŵ = 0.07 mm1
b = 15.7519 (14) ÅT = 120 K
c = 22.626 (2) Å0.50 × 0.05 × 0.05 mm
Data collection top
Bruker SMART
diffractometer
6228 independent reflections
Absorption correction: multi-scan
SADABS (Siemens, 1996)
4671 reflections with I > 2.0σ(I)
Tmin = 0.89, Tmax = 1.00Rint = 0.072
22025 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.052H-atom parameters constrained
S = 0.99Δρmax = 0.36 e Å3
4671 reflectionsΔρmin = 0.67 e Å3
218 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.20146 (6)0.26635 (4)0.34674 (3)0.0191
P20.27888 (2)0.184807 (17)0.324450 (11)0.0160
N30.15860 (6)0.11694 (5)0.33016 (3)0.0154
C40.03773 (5)0.16098 (5)0.34174 (3)0.0141
C50.06840 (5)0.25675 (5)0.33148 (4)0.0159
O60.34005 (6)0.19264 (5)0.26596 (3)0.0230
C70.15291 (7)0.03521 (5)0.29651 (4)0.0185
C80.04833 (4)0.02094 (4)0.32232 (3)0.0243
C90.12636 (4)0.05319 (4)0.23100 (3)0.0233
C100.27949 (4)0.01118 (4)0.30347 (4)0.0286
C110.39522 (5)0.17025 (5)0.38171 (4)0.0242
C120.50525 (4)0.23301 (4)0.37534 (4)0.0299
C130.01815 (6)0.14236 (5)0.40205 (4)0.0148
C140.05647 (6)0.12382 (5)0.45115 (4)0.0208
C150.00059 (6)0.11188 (5)0.50639 (4)0.0264
C160.12979 (6)0.11829 (5)0.51322 (4)0.0250
C170.20476 (6)0.13579 (5)0.46432 (4)0.0222
C180.14936 (5)0.14741 (5)0.40907 (4)0.0184
C190.01076 (7)0.31753 (5)0.36688 (4)0.0165
C200.03056 (6)0.34779 (5)0.42134 (4)0.0235
C210.04800 (6)0.39979 (5)0.45509 (4)0.0292
C220.16764 (6)0.42159 (5)0.43454 (5)0.0299
C230.20932 (6)0.39115 (5)0.38023 (4)0.0284
C240.13078 (6)0.33921 (5)0.34610 (4)0.0225
H250.02350.14480.31240.0500*
H260.05700.26800.29010.0500*
H270.42710.11310.38030.0500*
H280.35670.18020.41930.0500*
H290.47480.28940.37480.0500*
H300.56140.22640.40830.0500*
H310.55050.22380.33850.0500*
H320.34770.02150.28680.0500*
H330.27250.06300.28210.0500*
H340.29470.02350.34350.0500*
H350.19800.08070.21390.0500*
H360.11060.00230.21130.0500*
H370.05550.08850.22740.0500*
H380.06220.03010.36270.0500*
H390.03350.00330.31640.0500*
H400.05310.07440.30310.0500*
H410.14390.11860.44670.0500*
H420.05110.09680.53940.0500*
H430.16660.11050.55030.0500*
H440.29080.13940.46860.0500*
H450.19950.16130.37640.0500*
H460.15650.31770.31130.0500*
H470.28720.40460.36670.0500*
H480.21800.45670.45730.0500*
H490.02120.41930.49150.0500*
H500.11120.33400.43460.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.01197 (7)0.02140 (9)0.02380 (9)0.00045 (9)0.00212 (9)0.00062 (9)
P20.01047 (6)0.02233 (7)0.01516 (7)0.00164 (6)0.00186 (6)0.00170 (6)
N30.01180 (7)0.01935 (9)0.01509 (9)0.00216 (9)0.00222 (9)0.00071 (9)
C40.01089 (7)0.01962 (9)0.01166 (9)0.00192 (9)0.00088 (9)0.00096 (9)
C50.01260 (7)0.02025 (9)0.01478 (9)0.00231 (9)0.00112 (9)0.00272 (9)
O60.01727 (7)0.03161 (9)0.02005 (9)0.00062 (9)0.00755 (9)0.00340 (9)
C70.01707 (7)0.01956 (9)0.01876 (9)0.00228 (9)0.00370 (9)0.00010 (9)
C80.02436 (7)0.02216 (9)0.02642 (9)0.00229 (9)0.00471 (9)0.00206 (9)
C90.02626 (7)0.02744 (9)0.01630 (9)0.00026 (9)0.00373 (9)0.00290 (9)
C100.02264 (7)0.02454 (9)0.03856 (10)0.00774 (9)0.00336 (9)0.00052 (9)
C110.01570 (7)0.03357 (9)0.02339 (9)0.00302 (9)0.00415 (9)0.00190 (9)
C120.01659 (7)0.03512 (10)0.03811 (10)0.00085 (9)0.00507 (9)0.00560 (9)
C130.01286 (7)0.01897 (9)0.01266 (9)0.00077 (9)0.00081 (9)0.00141 (9)
C140.01406 (7)0.03414 (9)0.01418 (9)0.00420 (9)0.00078 (9)0.00454 (9)
C150.02026 (7)0.04497 (10)0.01404 (9)0.00709 (9)0.00130 (9)0.00670 (9)
C160.02120 (7)0.03760 (10)0.01611 (9)0.00363 (9)0.00556 (9)0.00576 (9)
C170.01380 (7)0.03351 (9)0.01920 (9)0.00096 (9)0.00466 (9)0.00355 (9)
C180.01260 (7)0.02742 (9)0.01512 (9)0.00017 (9)0.00049 (9)0.00171 (9)
C190.01417 (7)0.01757 (9)0.01789 (9)0.00135 (9)0.00227 (9)0.00206 (9)
C200.01888 (7)0.02824 (9)0.02333 (9)0.00113 (9)0.00083 (9)0.00585 (9)
C210.02826 (7)0.02801 (9)0.03129 (9)0.00291 (9)0.00766 (9)0.01001 (9)
C220.02754 (7)0.02284 (9)0.03938 (10)0.00372 (9)0.01536 (9)0.00148 (9)
C230.02037 (7)0.02922 (9)0.03549 (10)0.00918 (9)0.00734 (9)0.00759 (9)
C240.01727 (7)0.02677 (9)0.02338 (9)0.00599 (9)0.00115 (9)0.00522 (9)
Geometric parameters (Å, º) top
O1—P21.6030 (7)C11—H280.956
O1—C51.4520 (8)C12—H290.944
P2—N31.6632 (7)C12—H300.957
P2—O61.4772 (7)C12—H310.972
P2—C111.7984 (8)C13—C141.3920 (11)
N3—C41.4739 (9)C13—C181.3940 (9)
N3—C71.4969 (12)C14—C151.3944 (11)
C4—C51.5602 (10)C14—H410.931
C4—C131.5147 (11)C15—C161.3863 (9)
C4—H250.959C15—H420.948
C5—C191.5012 (11)C16—C171.3871 (11)
C5—H260.961C16—H430.932
C7—C81.5290 (10)C17—C181.3918 (11)
C7—C91.5347 (12)C17—H440.914
C7—C101.5291 (9)C18—H450.935
C8—H380.937C19—C201.3912 (12)
C8—H390.953C19—C241.3919 (10)
C8—H400.949C20—C211.3926 (11)
C9—H350.953C20—H500.927
C9—H360.932C21—C221.3870 (10)
C9—H370.935C21—H490.924
C10—H320.961C22—C231.3901 (14)
C10—H330.951C22—H480.923
C10—H340.939C23—C241.3968 (11)
C11—C121.5306 (8)C23—H470.902
C11—H270.962C24—H460.898
P2—O1—C5109.47 (5)P2—C11—H27109.5
O1—P2—N395.90 (4)C12—C11—H27109.7
O1—P2—O6115.91 (4)P2—C11—H28109.3
N3—P2—O6117.12 (4)C12—C11—H28107.5
O1—P2—C11102.86 (4)H27—C11—H28109.3
N3—P2—C11112.43 (4)C11—C12—H29110.6
O6—P2—C11111.02 (4)C11—C12—H30108.9
P2—N3—C4111.71 (5)H29—C12—H30108.9
P2—N3—C7122.95 (5)C11—C12—H31110.9
C4—N3—C7117.43 (6)H29—C12—H31107.2
N3—C4—C5104.46 (5)H30—C12—H31110.4
N3—C4—C13113.89 (6)C4—C13—C14122.68 (6)
C5—C4—C13113.69 (6)C4—C13—C18118.50 (7)
N3—C4—H25109.4C14—C13—C18118.77 (7)
C5—C4—H25107.1C13—C14—C15120.34 (6)
C13—C4—H25108.0C13—C14—H41119.4
C4—C5—O1105.39 (5)C15—C14—H41120.2
C4—C5—C19114.97 (6)C14—C15—C16120.57 (7)
O1—C5—C19110.09 (6)C14—C15—H42120.2
C4—C5—H26107.3C16—C15—H42119.2
O1—C5—H26109.4C15—C16—C17119.34 (7)
C19—C5—H26109.5C15—C16—H43120.2
N3—C7—C8109.40 (6)C17—C16—H43120.4
N3—C7—C9109.86 (7)C16—C17—C18120.24 (6)
C8—C7—C9110.14 (6)C16—C17—H44119.5
N3—C7—C10108.88 (6)C18—C17—H44120.2
C8—C7—C10108.25 (6)C13—C18—C17120.72 (7)
C9—C7—C10110.28 (6)C13—C18—H45118.9
C7—C8—H38110.4C17—C18—H45120.3
C7—C8—H39111.5C5—C19—C20121.14 (6)
H38—C8—H39110.0C5—C19—C24118.77 (8)
C7—C8—H40107.5C20—C19—C24119.97 (7)
H38—C8—H40107.5C19—C20—C21120.07 (7)
H39—C8—H40109.9C19—C20—H50119.6
C7—C9—H35109.4C21—C20—H50120.3
C7—C9—H36109.6C20—C21—C22120.14 (8)
H35—C9—H36109.8C20—C21—H49120.2
C7—C9—H37109.8C22—C21—H49119.6
H35—C9—H37109.1C21—C22—C23119.88 (7)
H36—C9—H37109.1C21—C22—H48119.0
C7—C10—H32110.9C23—C22—H48121.2
C7—C10—H33106.9C22—C23—C24120.23 (7)
H32—C10—H33108.5C22—C23—H47120.5
C7—C10—H34110.3C24—C23—H47119.3
H32—C10—H34111.1C23—C24—C19119.70 (8)
H33—C10—H34109.0C23—C24—H46121.8
P2—C11—C12111.48 (5)C19—C24—H46118.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H25···O6i0.962.403.244 (2)146
Symmetry code: (i) x1/2, y, z+1/2.
(II) (2S,4S,5R)and(2R,4R,5S)-3-tert-butyl-2-ethyl-4,5- diphenyl-[1,3,2]-oxazaphospholidine2-oxide top
Crystal data top
C20H26NO2PZ = 4
Mr = 343.39F(000) = 736
Triclinic, P1Dx = 1.224 Mg m3
Hall symbol: -P 1Synchrotron radiation, λ = 0.50606 Å
a = 6.7231 (5) ÅCell parameters from 11434 reflections
b = 11.9766 (6) Åθ = 2.5–16.5°
c = 23.6865 (16) ŵ = 0.07 mm1
α = 97.644 (3)°T = 120 K
β = 93.038 (2)°Needle, translucent pale white
γ = 98.742 (2)°0.40 × 0.05 × 0.05 mm
V = 1863.1 (2) Å3
Data collection top
Bruker SMART
diffractometer
7201 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.073
ω scansθmax = 20.9°, θmin = 1.2°
Absorption correction: multi-scan
SADABS (Siemens, 1996)
h = 99
Tmin = 0.91, Tmax = 1.00k = 1717
32894 measured reflectionsl = 3433
11718 independent reflections
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.507 0.574 0.220
wR(F2) = 0.053(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.48 e Å3
7201 reflectionsΔρmin = 0.58 e Å3
434 parametersExtinction correction: Larson (1970), Equation 22
0 restraintsExtinction coefficient: 660 (90)
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H26NO2Pγ = 98.742 (2)°
Mr = 343.39V = 1863.1 (2) Å3
Triclinic, P1Z = 4
a = 6.7231 (5) ÅSynchrotron radiation, λ = 0.50606 Å
b = 11.9766 (6) ŵ = 0.07 mm1
c = 23.6865 (16) ÅT = 120 K
α = 97.644 (3)°0.40 × 0.05 × 0.05 mm
β = 93.038 (2)°
Data collection top
Bruker SMART
diffractometer
11718 independent reflections
Absorption correction: multi-scan
SADABS (Siemens, 1996)
7201 reflections with I > 2.0σ(I)
Tmin = 0.91, Tmax = 1.00Rint = 0.073
32894 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.053H-atom parameters constrained
S = 1.06Δρmax = 0.48 e Å3
7201 reflectionsΔρmin = 0.58 e Å3
434 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.77651 (15)0.31881 (9)0.42493 (5)0.0209
P20.81472 (5)0.18934 (3)0.410737 (16)0.0171
N30.59819 (16)0.14115 (10)0.37339 (5)0.0160
C40.47693 (18)0.23247 (11)0.36808 (6)0.0144
C50.56125 (19)0.32181 (11)0.42069 (6)0.0167
O61.00407 (15)0.17922 (11)0.38347 (5)0.0285
C70.5095 (2)0.02075 (12)0.35146 (7)0.0197
C80.6752 (2)0.05377 (13)0.34813 (7)0.0266
C90.3515 (3)0.02224 (14)0.39119 (9)0.0346
C100.4092 (3)0.01434 (14)0.29150 (8)0.0321
C110.8173 (2)0.13664 (14)0.47865 (7)0.0249
C121.0154 (3)0.17880 (18)0.51469 (8)0.0358
C130.4924 (2)0.28161 (11)0.31219 (6)0.0161
C140.3241 (2)0.31951 (13)0.28902 (7)0.0220
C150.3346 (3)0.37081 (14)0.23960 (7)0.0290
C160.5133 (3)0.38401 (15)0.21295 (7)0.0326
C170.6823 (3)0.34621 (16)0.23553 (7)0.0315
C180.6713 (2)0.29432 (14)0.28493 (6)0.0233
C190.5196 (2)0.44037 (12)0.41757 (6)0.0194
C200.3338 (3)0.46618 (14)0.43280 (7)0.0279
C210.2833 (3)0.57296 (16)0.42753 (9)0.0380
C220.4205 (3)0.65441 (15)0.40754 (8)0.0389
C230.6063 (3)0.62959 (14)0.39270 (8)0.0346
C240.6570 (3)0.52238 (13)0.39744 (7)0.0260
O250.75529 (14)0.70375 (8)0.06658 (4)0.0184
P260.71085 (5)0.83190 (3)0.081143 (15)0.0150
N270.93126 (16)0.88544 (9)0.11615 (5)0.0147
C281.05303 (18)0.79439 (11)0.12373 (5)0.0134
C290.97127 (18)0.70373 (11)0.07130 (6)0.0150
O300.52514 (15)0.84066 (10)0.11036 (5)0.0249
C310.9832 (2)1.00090 (11)0.15068 (6)0.0174
C320.8722 (3)1.08434 (13)0.12286 (8)0.0282
C331.2104 (2)1.04049 (13)0.15114 (7)0.0243
C340.9180 (2)0.99958 (14)0.21169 (7)0.0257
C350.6924 (2)0.87958 (13)0.01208 (6)0.0218
C360.5017 (2)0.81638 (14)0.02358 (7)0.0278
C371.03775 (19)0.74499 (11)0.17934 (6)0.0149
C380.8540 (2)0.71596 (13)0.20296 (6)0.0219
C390.8468 (2)0.66298 (15)0.25174 (7)0.0280
C401.0230 (3)0.63861 (15)0.27774 (7)0.0307
C411.2053 (3)0.66725 (15)0.25460 (7)0.0278
C421.2132 (2)0.72004 (12)0.20559 (6)0.0194
C431.01773 (19)0.58654 (11)0.07508 (6)0.0155
C440.8778 (2)0.50090 (12)0.09169 (6)0.0200
C450.9311 (2)0.39454 (12)0.09658 (7)0.0232
C461.1236 (2)0.37327 (13)0.08559 (7)0.0248
C471.2625 (2)0.45848 (13)0.06876 (7)0.0256
C481.2102 (2)0.56452 (12)0.06352 (7)0.0212
H490.50670.29490.45470.0500*
H500.34270.20310.37340.0500*
H510.71230.16640.49850.0500*
H520.78810.05610.47230.0500*
H531.00610.15120.54940.0500*
H541.12040.14960.49480.0500*
H551.03970.25840.51950.0500*
H560.77470.02820.32490.0500*
H570.73140.05610.38540.0500*
H580.61290.12890.33090.0500*
H590.41970.02390.42700.0500*
H600.28810.09760.37620.0500*
H610.25530.02590.39610.0500*
H620.35080.05880.27840.0500*
H630.30560.05810.29300.0500*
H640.50160.03850.26610.0500*
H650.78410.26810.30010.0500*
H660.20910.31130.30690.0500*
H670.22610.39630.22510.0500*
H680.52230.41720.18080.0500*
H690.80370.35300.21730.0500*
H700.24230.41130.44650.0500*
H710.16340.58920.43760.0500*
H720.38990.72490.40460.0500*
H730.69530.68180.37780.0500*
H740.77750.50520.38700.0500*
H751.18680.82070.11810.0500*
H761.02660.72940.03820.0500*
H770.80920.86720.00680.0500*
H780.68850.95790.01800.0500*
H790.38850.83520.00540.0500*
H800.50210.83920.05940.0500*
H810.49900.73690.02730.0500*
H820.73461.06370.12080.0500*
H830.91411.08940.08570.0500*
H840.90621.15750.14420.0500*
H851.28260.99360.16930.0500*
H861.24111.11660.17040.0500*
H871.25261.04010.11360.0500*
H880.94121.07450.23130.0500*
H890.99190.95160.23060.0500*
H900.78010.97100.21170.0500*
H911.33280.73630.18950.0500*
H921.32090.65020.27190.0500*
H931.01530.60230.30990.0500*
H940.72590.64640.26760.0500*
H950.73790.73230.18620.0500*
H961.30320.62150.05290.0500*
H971.38530.44540.06050.0500*
H981.16060.30490.09000.0500*
H990.83510.33760.10900.0500*
H1000.75170.51520.10070.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0148 (5)0.0197 (5)0.0279 (5)0.0016 (4)0.0040 (4)0.0055 (4)
P20.01208 (16)0.02038 (18)0.02088 (18)0.00461 (13)0.00099 (13)0.00844 (15)
N30.0135 (5)0.0147 (5)0.0215 (6)0.0052 (4)0.0004 (4)0.0056 (5)
C40.0110 (5)0.0139 (6)0.0193 (6)0.0035 (4)0.0019 (5)0.0048 (5)
C50.0154 (6)0.0178 (6)0.0180 (6)0.0044 (5)0.0004 (5)0.0049 (5)
O60.0135 (5)0.0382 (7)0.0373 (7)0.0073 (4)0.0053 (4)0.0138 (6)
C70.0196 (6)0.0143 (6)0.0263 (7)0.0047 (5)0.0025 (5)0.0042 (6)
C80.0310 (8)0.0228 (7)0.0295 (8)0.0145 (6)0.0022 (6)0.0044 (7)
C90.0289 (8)0.0210 (7)0.0569 (12)0.0029 (6)0.0141 (8)0.0138 (8)
C100.0366 (9)0.0200 (7)0.0369 (9)0.0071 (6)0.0140 (7)0.0024 (7)
C110.0259 (7)0.0284 (8)0.0231 (7)0.0075 (6)0.0016 (6)0.0109 (7)
C120.0329 (9)0.0445 (11)0.0314 (9)0.0122 (8)0.0108 (7)0.0094 (8)
C130.0165 (6)0.0138 (6)0.0179 (6)0.0022 (5)0.0015 (5)0.0035 (5)
C140.0207 (7)0.0218 (7)0.0239 (7)0.0060 (5)0.0039 (5)0.0049 (6)
C150.0335 (9)0.0272 (8)0.0279 (8)0.0089 (7)0.0075 (7)0.0096 (7)
C160.0441 (10)0.0303 (9)0.0248 (8)0.0019 (7)0.0024 (7)0.0151 (7)
C170.0310 (8)0.0400 (10)0.0253 (8)0.0014 (7)0.0057 (6)0.0152 (8)
C180.0197 (7)0.0292 (8)0.0229 (7)0.0043 (6)0.0029 (5)0.0103 (6)
C190.0246 (7)0.0165 (6)0.0167 (6)0.0049 (5)0.0027 (5)0.0012 (5)
C200.0295 (8)0.0251 (8)0.0305 (8)0.0112 (6)0.0016 (6)0.0019 (7)
C210.0464 (11)0.0317 (9)0.0388 (10)0.0245 (8)0.0028 (8)0.0031 (8)
C220.0655 (14)0.0214 (8)0.0316 (9)0.0197 (8)0.0090 (9)0.0009 (7)
C230.0564 (12)0.0176 (7)0.0282 (8)0.0026 (7)0.0063 (8)0.0051 (7)
C240.0328 (8)0.0182 (7)0.0270 (8)0.0030 (6)0.0021 (6)0.0057 (6)
O250.0137 (4)0.0160 (5)0.0252 (5)0.0019 (4)0.0023 (4)0.0045 (4)
P260.00939 (15)0.01635 (16)0.02064 (18)0.00295 (12)0.00081 (12)0.00666 (14)
N270.0117 (5)0.0124 (5)0.0208 (5)0.0029 (4)0.0006 (4)0.0043 (4)
C280.0098 (5)0.0136 (5)0.0180 (6)0.0036 (4)0.0015 (4)0.0047 (5)
C290.0109 (5)0.0160 (6)0.0187 (6)0.0025 (4)0.0013 (5)0.0037 (5)
O300.0119 (5)0.0308 (6)0.0343 (6)0.0054 (4)0.0061 (4)0.0090 (5)
C310.0173 (6)0.0131 (6)0.0226 (7)0.0035 (5)0.0014 (5)0.0038 (5)
C320.0332 (9)0.0174 (7)0.0357 (9)0.0100 (6)0.0041 (7)0.0051 (7)
C330.0189 (7)0.0199 (7)0.0316 (8)0.0031 (5)0.0017 (6)0.0023 (6)
C340.0289 (8)0.0255 (7)0.0231 (7)0.0072 (6)0.0070 (6)0.0002 (6)
C350.0196 (7)0.0230 (7)0.0240 (7)0.0025 (5)0.0018 (5)0.0099 (6)
C360.0245 (7)0.0290 (8)0.0304 (8)0.0045 (6)0.0091 (6)0.0099 (7)
C370.0145 (6)0.0133 (6)0.0173 (6)0.0030 (5)0.0001 (5)0.0033 (5)
C380.0174 (6)0.0279 (7)0.0223 (7)0.0032 (5)0.0038 (5)0.0103 (6)
C390.0280 (8)0.0330 (9)0.0254 (8)0.0013 (7)0.0060 (6)0.0150 (7)
C400.0377 (9)0.0318 (9)0.0257 (8)0.0057 (7)0.0014 (7)0.0152 (7)
C410.0279 (8)0.0308 (8)0.0264 (8)0.0081 (6)0.0053 (6)0.0097 (7)
C420.0166 (6)0.0195 (6)0.0233 (7)0.0057 (5)0.0021 (5)0.0053 (6)
C430.0161 (6)0.0133 (6)0.0175 (6)0.0038 (5)0.0004 (5)0.0029 (5)
C440.0182 (6)0.0173 (6)0.0253 (7)0.0021 (5)0.0004 (5)0.0070 (6)
C450.0268 (7)0.0174 (7)0.0256 (7)0.0019 (6)0.0013 (6)0.0066 (6)
C460.0306 (8)0.0166 (6)0.0278 (8)0.0089 (6)0.0040 (6)0.0017 (6)
C470.0207 (7)0.0198 (7)0.0366 (9)0.0087 (5)0.0002 (6)0.0005 (7)
C480.0183 (6)0.0166 (6)0.0289 (7)0.0045 (5)0.0035 (5)0.0017 (6)
Geometric parameters (Å, º) top
P2—O11.605 (2)C17—H690.9400
P2—O61.472 (2)C18—H650.9400
P2—N31.645 (2)C20—H700.9300
P2—C111.805 (3)C21—H710.8900
P26—O301.470 (2)C22—H720.9100
P26—N271.654 (2)C23—H730.9200
P26—O251.605 (2)C24—H740.9000
P26—C351.807 (3)C28—C291.553 (3)
O1—C51.451 (3)C28—C371.516 (3)
O25—C291.450 (3)C29—C431.498 (3)
N3—C41.475 (3)C31—C321.529 (4)
N3—C71.486 (3)C31—C331.529 (4)
N27—C311.491 (3)C31—C341.534 (4)
N27—C281.483 (3)C35—C361.533 (4)
C4—C131.521 (3)C37—C381.400 (4)
C4—C51.551 (3)C37—C421.395 (4)
C5—C191.498 (3)C38—C391.390 (4)
C7—C101.527 (4)C39—C401.395 (5)
C7—C81.529 (4)C40—C411.384 (5)
C7—C91.532 (5)C41—C421.394 (4)
C11—C121.522 (4)C43—C441.395 (4)
C13—C141.396 (4)C43—C481.393 (4)
C13—C181.392 (4)C44—C451.393 (3)
C14—C151.392 (4)C45—C461.388 (4)
C15—C161.384 (5)C46—C471.389 (4)
C16—C171.391 (5)C47—C481.387 (3)
C17—C181.397 (4)C28—H750.9300
C19—C201.387 (4)C29—H760.9500
C19—C241.394 (4)C32—H820.9200
C20—C211.392 (5)C32—H830.9500
C21—C221.388 (6)C32—H840.9400
C22—C231.380 (6)C33—H850.9300
C23—C241.395 (4)C33—H860.9500
C4—H500.9400C33—H870.9500
C5—H490.9800C34—H880.9400
C8—H570.9500C34—H890.9500
C8—H560.9300C34—H900.9400
C8—H580.9600C35—H770.9500
C9—H590.9500C35—H780.9300
C9—H600.9500C36—H790.9400
C9—H610.9300C36—H800.9300
C10—H620.9100C36—H810.9400
C10—H630.9300C38—H950.9200
C10—H640.9300C39—H940.9200
C11—H510.9600C40—H930.9300
C11—H520.9500C41—H920.9200
C12—H530.9300C42—H910.9100
C12—H540.9500C44—H1000.9200
C12—H550.9300C45—H990.9500
C14—H660.9000C46—H980.9100
C15—H670.9000C47—H970.8900
C16—H680.9100C48—H960.9200
O1—P2—O6113.21 (13)C21—C20—H70120.00
O1—P2—N396.02 (11)C19—C20—H70120.00
O1—P2—C11105.03 (14)C22—C21—H71120.00
O6—P2—N3119.21 (12)C20—C21—H71120.00
O6—P2—C11111.04 (13)C21—C22—H72120.00
N3—P2—C11110.67 (12)C23—C22—H72119.00
N27—P26—C35111.18 (12)C22—C23—H73121.00
O25—P26—N2796.46 (11)C24—C23—H73119.00
O25—P26—C35103.73 (11)C19—C24—H74120.00
O25—P26—O30113.94 (12)C23—C24—H74121.00
O30—P26—C35110.75 (13)N27—C28—C29101.51 (17)
O30—P26—N27119.06 (12)N27—C28—C37116.56 (19)
P2—O1—C5109.54 (16)C29—C28—C37112.0 (2)
P26—O25—C29109.59 (15)O25—C29—C28104.99 (18)
P2—N3—C7128.14 (18)O25—C29—C43111.17 (19)
P2—N3—C4111.97 (16)C28—C29—C43114.9 (2)
C4—N3—C7119.54 (19)N27—C31—C32109.0 (2)
C28—N27—C31121.12 (19)N27—C31—C33108.7 (2)
P26—N27—C31125.57 (17)N27—C31—C34111.2 (2)
P26—N27—C28111.09 (15)C32—C31—C33108.9 (2)
C5—C4—C13112.6 (2)C32—C31—C34108.0 (2)
N3—C4—C13114.38 (19)C33—C31—C34110.8 (2)
N3—C4—C5102.21 (18)P26—C35—C36110.86 (19)
O1—C5—C4104.65 (19)C28—C37—C38122.7 (2)
O1—C5—C19111.3 (2)C28—C37—C42118.2 (2)
C4—C5—C19115.1 (2)C38—C37—C42118.9 (2)
N3—C7—C10109.4 (2)C37—C38—C39120.3 (3)
C8—C7—C9110.2 (2)C38—C39—C40120.4 (3)
C8—C7—C10108.4 (2)C39—C40—C41119.5 (3)
C9—C7—C10109.4 (3)C40—C41—C42120.3 (3)
N3—C7—C8110.1 (2)C37—C42—C41120.5 (3)
N3—C7—C9109.3 (2)C29—C43—C44122.2 (2)
P2—C11—C12112.6 (2)C29—C43—C48118.3 (2)
C14—C13—C18119.3 (2)C44—C43—C48119.5 (2)
C4—C13—C14118.6 (2)C43—C44—C45119.9 (2)
C4—C13—C18122.1 (2)C44—C45—C46120.4 (2)
C13—C14—C15120.6 (3)C45—C46—C47119.6 (2)
C14—C15—C16119.9 (3)C46—C47—C48120.3 (3)
C15—C16—C17120.1 (3)C43—C48—C47120.3 (2)
C16—C17—C18120.0 (3)N27—C28—H75109.00
C13—C18—C17120.2 (3)C29—C28—H75106.00
C5—C19—C20118.1 (2)C37—C28—H75111.00
C5—C19—C24122.2 (2)O25—C29—H76109.00
C20—C19—C24119.6 (3)C28—C29—H76108.00
C19—C20—C21120.4 (3)C43—C29—H76109.00
C20—C21—C22119.8 (4)C31—C32—H82113.00
C21—C22—C23120.1 (3)C31—C32—H83110.00
C22—C23—C24120.4 (3)C31—C32—H84109.00
C19—C24—C23119.8 (3)H82—C32—H83109.00
C5—C4—H50108.00H82—C32—H84108.00
N3—C4—H50108.00H83—C32—H84107.00
C13—C4—H50111.00C31—C33—H85111.00
C19—C5—H49110.00C31—C33—H86108.00
C4—C5—H49108.00C31—C33—H87111.00
O1—C5—H49107.00H85—C33—H86110.00
C7—C8—H56112.00H85—C33—H87108.00
C7—C8—H57110.00H86—C33—H87108.00
C7—C8—H58107.00C31—C34—H88109.00
H57—C8—H58110.00C31—C34—H89109.00
H56—C8—H57111.00C31—C34—H90111.00
H56—C8—H58107.00H88—C34—H89111.00
C7—C9—H59108.00H88—C34—H90108.00
H59—C9—H60109.00H89—C34—H90108.00
C7—C9—H60110.00P26—C35—H77109.00
C7—C9—H61111.00P26—C35—H78108.00
H60—C9—H61110.00C36—C35—H77111.00
H59—C9—H61109.00C36—C35—H78110.00
C7—C10—H64112.00H77—C35—H78109.00
C7—C10—H63109.00C35—C36—H79109.00
H63—C10—H64111.00C35—C36—H80108.00
H62—C10—H63107.00C35—C36—H81111.00
H62—C10—H64109.00H79—C36—H80110.00
C7—C10—H62110.00H79—C36—H81110.00
P2—C11—H52109.00H80—C36—H81109.00
C12—C11—H51108.00C37—C38—H95120.00
C12—C11—H52112.00C39—C38—H95120.00
H51—C11—H52110.00C38—C39—H94120.00
P2—C11—H51106.00C40—C39—H94120.00
C11—C12—H53109.00C39—C40—H93119.00
C11—C12—H54108.00C41—C40—H93121.00
H54—C12—H55110.00C40—C41—H92119.00
H53—C12—H55112.00C42—C41—H92121.00
C11—C12—H55109.00C37—C42—H91119.00
H53—C12—H54110.00C41—C42—H91120.00
C15—C14—H66121.00C43—C44—H100120.00
C13—C14—H66119.00C45—C44—H100120.00
C14—C15—H67120.00C44—C45—H99119.00
C16—C15—H67120.00C46—C45—H99121.00
C15—C16—H68121.00C45—C46—H98121.00
C17—C16—H68119.00C47—C46—H98120.00
C18—C17—H69119.00C46—C47—H97121.00
C16—C17—H69121.00C48—C47—H97119.00
C13—C18—H65119.00C43—C48—H96119.00
C17—C18—H65120.00C47—C48—H96120.00
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H50···O6i0.942.283.196 (3)165
C28—H75···O30ii0.932.273.179 (3)165
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
(III) (2S,4S,5R)-3-tert-butyl-2-[(1S)-1-?uoro-1-methyl- 2-oxo-propyl]-4,5-diphenyl-[1,3,2]-oxazaphospholidine2- oxide top
Crystal data top
C22H27FNO3PF(000) = 856
Mr = 403.43Dx = 1.231 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15 reflections
a = 6.411 (2) Åθ = 4–10°
b = 16.206 (4) ŵ = 0.16 mm1
c = 21.242 (5) ÅT = 293 K
β = 99.51 (2)°Needle, translucent pale white
V = 2176.7 (10) Å30.40 × 0.05 × 0.02 mm
Z = 4
Data collection top
Siemens P3
diffractometer
Rint = 0.057
Graphite monochromatorθmax = 21.1°, θmin = 1.6°
ω/2θ scansh = 06
Absorption correction: ψ scan
?
k = 016
Tmin = 0.86, Tmax = 0.96l = 2121
2740 measured reflections2 standard reflections every 60 min
2355 independent reflections intensity decay: 4.0%
558 reflections with I > 2.0σ(I)
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.128H-atom parameters constrained
wR(F2) = 0.144 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.701 0.529 0.357
S = 1.10(Δ/σ)max = 0.006
558 reflectionsΔρmax = 0.47 e Å3
113 parametersΔρmin = 0.56 e Å3
11 restraints
Crystal data top
C22H27FNO3PV = 2176.7 (10) Å3
Mr = 403.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.411 (2) ŵ = 0.16 mm1
b = 16.206 (4) ÅT = 293 K
c = 21.242 (5) Å0.40 × 0.05 × 0.02 mm
β = 99.51 (2)°
Data collection top
Siemens P3
diffractometer
558 reflections with I > 2.0σ(I)
Absorption correction: ψ scan
?
Rint = 0.057
Tmin = 0.86, Tmax = 0.96θmax = 21.1°
2740 measured reflections2 standard reflections every 60 min
2355 independent reflections intensity decay: 4.0%
Refinement top
R[F2 > 2σ(F2)] = 0.12811 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.10Δρmax = 0.47 e Å3
558 reflectionsΔρmin = 0.56 e Å3
113 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.185 (3)0.0205 (12)0.7567 (9)0.058 (6)*
P20.0609 (14)0.0838 (6)0.7064 (4)0.045 (3)*
N30.225 (4)0.1564 (14)0.7211 (10)0.036 (7)*
C40.402 (5)0.1421 (18)0.7719 (12)0.044 (9)*
C50.404 (5)0.0479 (18)0.7790 (13)0.043 (9)*
O60.167 (3)0.1005 (12)0.7122 (9)0.057 (6)*
C70.079 (5)0.030 (2)0.6328 (14)0.055 (10)*
F80.301 (3)0.0326 (12)0.6251 (9)0.089 (7)*
C90.022 (5)0.062 (2)0.6355 (15)0.073 (11)*
C100.059 (6)0.065 (2)0.5700 (17)0.075 (12)*
O110.048 (4)0.0947 (15)0.5309 (11)0.087 (8)*
C120.279 (5)0.055 (2)0.5596 (16)0.079 (12)*
C130.510 (4)0.0086 (18)0.8395 (13)0.043 (9)*
C140.381 (4)0.0333 (17)0.8758 (12)0.053 (9)*
C150.475 (4)0.066 (2)0.9343 (13)0.072 (11)*
C160.690 (4)0.0602 (19)0.9573 (14)0.065 (11)*
C170.829 (5)0.022 (2)0.9223 (16)0.080 (12)*
C180.725 (4)0.015 (2)0.8632 (15)0.068 (11)*
C190.388 (4)0.183 (2)0.8342 (14)0.049 (10)*
C200.205 (5)0.183 (2)0.8616 (13)0.064 (11)*
C210.186 (5)0.2242 (19)0.9183 (13)0.074 (11)*
C220.373 (4)0.259 (2)0.9501 (16)0.084 (13)*
C230.564 (5)0.264 (2)0.9274 (14)0.079 (12)*
C240.563 (6)0.223 (2)0.8693 (14)0.086 (13)*
C250.203 (8)0.246 (3)0.689 (2)0.107 (15)*
C260.383 (10)0.241 (4)0.641 (3)0.22 (3)*
C270.250 (10)0.309 (4)0.728 (3)0.24 (3)*
C280.035 (7)0.249 (2)0.6367 (19)0.121 (17)*
H290.48360.02760.74650.0399*
H300.53350.16020.75810.0549*
H310.11900.08840.66860.0791*
H320.03150.08760.59530.0791*
H330.11960.06760.64420.0791*
H340.33470.06710.59790.0895*
H350.31280.00120.54730.0895*
H360.34320.09120.52620.0895*
H370.23770.04060.86120.0478*
H380.38800.09250.95930.0779*
H390.73980.08320.99710.0690*
H400.97570.02110.93500.0943*
H410.80320.04800.83980.0691*
H420.08660.15520.84130.0703*
H430.06020.22890.93410.0776*
H440.36640.28080.99020.1019*
H450.68020.29180.94950.0877*
H460.68800.22210.85240.1146*
H470.53040.25540.67040.1789*
H480.34010.28570.60460.1789*
H490.37920.18010.62320.1789*
H500.40230.31430.73650.1829*
H510.19750.30040.76760.1829*
H520.18830.35810.70740.1829*
H530.03470.19930.61190.1185*
H540.09800.25380.65150.1185*
H550.05470.29540.61060.1185*
Geometric parameters (Å, º) top
O1—P21.60 (2)C16—C171.400 (10)
O1—C51.47 (3)C16—H390.930
P2—N31.58 (2)C17—C181.45 (4)
P2—O61.51 (2)C17—H400.932
P2—C71.81 (3)C18—H410.930
N3—C41.45 (3)C19—C201.395 (10)
N3—C251.60 (4)C19—C241.396 (10)
C4—C51.53 (4)C20—C211.398 (10)
C4—C191.50 (3)C20—H420.929
C4—H300.982C21—C221.390 (10)
C5—C131.49 (3)C21—H430.929
C5—H290.980C22—C231.395 (10)
C7—F81.46 (3)C22—H440.930
C7—C91.53 (4)C23—C241.400 (10)
C7—C101.58 (4)C23—H450.928
C9—H310.960C24—H460.930
C9—H320.962C25—C261.66 (6)
C9—H330.962C25—C271.31 (6)
C10—O111.26 (3)C25—C281.42 (5)
C10—C121.41 (4)C26—H471.065
C12—H340.961C26—H481.064
C12—H350.960C26—H491.065
C12—H360.960C27—H500.965
C13—C141.395 (9)C27—H510.965
C13—C181.393 (10)C27—H520.964
C14—C151.393 (10)C28—H530.959
C14—H370.929C28—H540.960
C15—C161.389 (10)C28—H550.960
C15—H380.932
P2—O1—C5111.4 (17)C15—C16—C17122 (3)
O1—P2—N395.9 (13)C15—C16—H39117.7
O1—P2—O6116.3 (12)C17—C16—H39120.4
N3—P2—O6118.2 (13)C16—C17—C18114 (3)
O1—P2—C799.8 (14)C16—C17—H40123.5
N3—P2—C7113.4 (13)C18—C17—H40122.9
O6—P2—C7111.0 (14)C17—C18—C13125 (3)
P2—N3—C4116 (2)C17—C18—H41119.3
P2—N3—C25126 (2)C13—C18—H41116.0
C4—N3—C25118 (3)C4—C19—C20123 (3)
N3—C4—C5103 (2)C4—C19—C24121 (2)
N3—C4—C19116 (2)C20—C19—C24116 (3)
C5—C4—C19111 (2)C19—C20—C21124 (3)
N3—C4—H30109.5C19—C20—H42119.1
C5—C4—H30109.4C21—C20—H42116.9
C19—C4—H30108.0C20—C21—C22115 (3)
C4—C5—O1106 (2)C20—C21—H43123.8
C4—C5—C13120 (3)C22—C21—H43121.3
O1—C5—C13115 (2)C21—C22—C23126 (3)
C4—C5—H29105.2C21—C22—H44115.9
O1—C5—H29104.6C23—C22—H44118.0
C13—C5—H29104.4C22—C23—C24114 (3)
P2—C7—F8106 (2)C22—C23—H45122.1
P2—C7—C9113 (2)C24—C23—H45124.3
F8—C7—C9106 (3)C23—C24—C19125 (3)
P2—C7—C10116 (2)C23—C24—H46117.8
F8—C7—C10108 (2)C19—C24—H46116.9
C9—C7—C10107 (3)N3—C25—C26101 (3)
C7—C9—H31109.5N3—C25—C27116 (5)
C7—C9—H32109.7C26—C25—C27108 (5)
H31—C9—H32109.2N3—C25—C28111 (4)
C7—C9—H33109.9C26—C25—C2892 (4)
H31—C9—H33109.4C27—C25—C28123 (5)
H32—C9—H33109.2C25—C26—H47106.2
C7—C10—O11114 (3)C25—C26—H48107.4
C7—C10—C12120 (3)H47—C26—H48112.0
O11—C10—C12126 (3)C25—C26—H49107.1
C10—C12—H34110.1H47—C26—H49111.9
C10—C12—H35109.3H48—C26—H49112.0
H34—C12—H35109.2C25—C27—H50107.9
C10—C12—H36109.6C25—C27—H51110.9
H34—C12—H36109.2H50—C27—H51110.0
H35—C12—H36109.3C25—C27—H52108.5
C5—C13—C14117 (2)H50—C27—H52109.7
C5—C13—C18124 (3)H51—C27—H52109.7
C14—C13—C18119 (3)C25—C28—H53110.1
C13—C14—C15118 (3)C25—C28—H54110.1
C13—C14—H37121.4H53—C28—H54109.3
C15—C14—H37120.3C25—C28—H55108.9
C14—C15—C16123 (3)H53—C28—H55109.2
C14—C15—H38118.4H54—C28—H55109.2
C16—C15—H38118.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H30···O6i0.982.493.30 (4)139
Symmetry code: (i) x+1, y, z.
(IV) (2R,4R,5S)-3-tert-butyl-2-[(1S)-1-fluoro-1-methyl- 2-oxo-propyl]-4,5-diphenyl-[1,3,2]-oxazaphospholidine2- oxide. top
Crystal data top
C22H27FNO3PF(000) = 856
Mr = 403.43Dx = 1.248 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13 reflections
a = 19.252 (2) Åθ = 4.2–12.3°
b = 6.584 (1) ŵ = 0.16 mm1
c = 17.295 (2) ÅT = 293 K
β = 101.73 (2)°Needle, translucent pale white
V = 2146.5 (5) Å30.20 × 0.06 × 0.04 mm
Z = 4
Data collection top
Siemens P3
diffractometer
Rint = 0.041
Graphite monochromatorθmax = 23.1°, θmin = 2.2°
ω/2θ scansh = 2120
Absorption correction: ψ scan
?
k = 70
Tmin = 0.85, Tmax = 0.94l = 019
3395 measured reflections3 standard reflections every 60 min
2972 independent reflections intensity decay: 0.2%
660 reflections with I > 2.0σ(I)
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.113H-atom parameters constrained
wR(F2) = 0.126 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.676 0.602 0.331
S = 1.18(Δ/σ)max = 0.000028
660 reflectionsΔρmax = 0.71 e Å3
113 parametersΔρmin = 0.63 e Å3
11 restraints
Crystal data top
C22H27FNO3PV = 2146.5 (5) Å3
Mr = 403.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.252 (2) ŵ = 0.16 mm1
b = 6.584 (1) ÅT = 293 K
c = 17.295 (2) Å0.20 × 0.06 × 0.04 mm
β = 101.73 (2)°
Data collection top
Siemens P3
diffractometer
660 reflections with I > 2.0σ(I)
Absorption correction: ψ scan
?
Rint = 0.041
Tmin = 0.85, Tmax = 0.94θmax = 23.1°
3395 measured reflections3 standard reflections every 60 min
2972 independent reflections intensity decay: 0.2%
Refinement top
R[F2 > 2σ(F2)] = 0.11311 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.18Δρmax = 0.71 e Å3
660 reflectionsΔρmin = 0.63 e Å3
113 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2699 (7)0.1501 (18)0.7518 (8)0.043 (4)*
P20.3135 (3)0.0756 (11)0.8359 (4)0.051 (2)*
N30.2917 (8)0.266 (2)0.8846 (10)0.039 (5)*
C40.2426 (9)0.409 (3)0.8394 (11)0.036 (5)*
C50.2556 (11)0.366 (3)0.7548 (12)0.041 (7)*
O60.3015 (8)0.139 (2)0.8554 (9)0.061 (5)*
C70.4082 (10)0.084 (3)0.8207 (11)0.031 (5)*
F80.4234 (6)0.298 (2)0.8233 (7)0.066 (4)*
C90.4624 (13)0.018 (4)0.8840 (15)0.084 (9)*
C100.4086 (12)0.015 (4)0.7363 (15)0.057 (8)*
O110.4224 (10)0.141 (3)0.6923 (12)0.092 (6)*
C120.3993 (13)0.203 (4)0.7251 (15)0.080 (9)*
C130.1992 (10)0.426 (3)0.6856 (11)0.049 (6)*
C140.1503 (10)0.288 (4)0.6446 (11)0.058 (7)*
C150.0974 (11)0.343 (3)0.5802 (11)0.056 (7)*
C160.0990 (12)0.541 (3)0.5529 (14)0.065 (7)*
C170.1483 (12)0.682 (4)0.5902 (14)0.071 (8)*
C180.2004 (12)0.623 (3)0.6574 (14)0.062 (7)*
C190.1676 (11)0.385 (3)0.8387 (14)0.060 (8)*
C200.1271 (10)0.559 (4)0.8379 (13)0.063 (7)*
C210.0545 (10)0.563 (4)0.8357 (15)0.085 (8)*
C220.0235 (13)0.376 (3)0.8445 (15)0.076 (8)*
C230.0597 (10)0.192 (4)0.8495 (14)0.074 (8)*
C240.1317 (10)0.206 (3)0.8474 (13)0.060 (7)*
C250.3178 (11)0.302 (4)0.9738 (13)0.057 (7)*
C260.2598 (13)0.402 (4)1.0065 (16)0.089 (9)*
C270.3345 (13)0.098 (4)1.0165 (15)0.083 (9)*
C280.3811 (12)0.445 (4)0.9839 (15)0.075 (8)*
H290.29900.43790.74950.0532*
H300.25770.54830.85500.0474*
H310.46310.04670.93380.0792*
H320.50850.00690.87110.0792*
H330.45050.15920.88740.0792*
H340.35130.23910.72690.0995*
H350.40910.24080.67490.0995*
H360.43120.27350.76630.0995*
H370.15220.15380.66200.0610*
H380.06330.25000.55630.0687*
H390.06540.58070.50880.0811*
H400.14860.81290.57010.0955*
H410.23300.71630.68390.0939*
H420.15000.68350.83770.1030*
H430.02830.68270.82850.1202*
H440.02390.37390.84860.0973*
H450.03750.06780.85230.0841*
H460.15750.08540.85070.0714*
H470.36820.56950.95560.0890*
H480.39710.47461.03900.0890*
H490.41840.37970.96400.0890*
H500.34860.12211.07230.1182*
H510.37220.03170.99790.1182*
H520.29310.01361.00650.1182*
H530.27330.40641.06310.0813*
H540.25220.53860.98640.0813*
H550.21690.32520.99130.0813*
Geometric parameters (Å, º) top
O1—P21.602 (14)C16—C171.390 (9)
O1—C51.45 (2)C16—H390.932
P2—N31.613 (17)C17—C181.43 (3)
P2—O61.483 (16)C17—H400.931
P2—C71.896 (19)C18—H410.931
N3—C41.45 (2)C19—C201.388 (9)
N3—C251.54 (2)C19—C241.389 (9)
C4—C51.56 (3)C20—C211.390 (9)
C4—C191.45 (3)C20—H420.929
C4—H300.981C21—C221.390 (9)
C5—C131.50 (3)C21—H430.928
C5—H290.980C22—C231.394 (9)
C7—F81.44 (2)C22—H440.930
C7—C91.51 (3)C23—C241.397 (9)
C7—C101.53 (3)C23—H450.929
C9—H310.959C24—H460.930
C9—H320.961C25—C261.50 (3)
C9—H330.961C25—C271.53 (3)
C10—O111.19 (3)C25—C281.52 (3)
C10—C121.46 (3)C26—H530.962
C12—H340.960C26—H540.961
C12—H350.958C26—H550.960
C12—H360.958C27—H500.960
C13—C141.391 (9)C27—H510.959
C13—C181.387 (9)C27—H520.960
C14—C151.394 (9)C28—H470.961
C14—H370.933C28—H480.959
C15—C161.389 (9)C28—H490.959
C15—H380.929
P2—O1—C5109.6 (13)C15—C16—C17122 (2)
O1—P2—N395.3 (8)C15—C16—H39119.0
O1—P2—O6114.9 (9)C17—C16—H39119.0
N3—P2—O6123.7 (9)C16—C17—C18120 (2)
O1—P2—C7101.9 (8)C16—C17—H40120.2
N3—P2—C7114.2 (9)C18—C17—H40120.1
O6—P2—C7104.9 (10)C17—C18—C13119 (2)
P2—N3—C4115.9 (13)C17—C18—H41120.7
P2—N3—C25125.1 (14)C13—C18—H41120.3
C4—N3—C25119.0 (17)C4—C19—C20117.6 (18)
N3—C4—C5100.1 (15)C4—C19—C24127.6 (19)
N3—C4—C19118.1 (17)C20—C19—C24114 (2)
C5—C4—C19108.7 (17)C19—C20—C21125 (2)
N3—C4—H30109.5C19—C20—H42117.6
C5—C4—H30109.5C21—C20—H42117.2
C19—C4—H30110.3C20—C21—C22116 (3)
C4—C5—O1106.3 (16)C20—C21—H43122.3
C4—C5—C13118.3 (16)C22—C21—H43122.1
O1—C5—C13109.9 (17)C21—C22—C23124 (2)
C4—C5—H29107.5C21—C22—H44118.2
O1—C5—H29107.3C23—C22—H44117.8
C13—C5—H29107.0C22—C23—C24115 (2)
P2—C7—F8102.7 (13)C22—C23—H45122.7
P2—C7—C9115.5 (14)C24—C23—H45122.0
F8—C7—C9107.9 (17)C23—C24—C19125 (2)
P2—C7—C10108.4 (14)C23—C24—H46117.6
F8—C7—C10106.2 (17)C19—C24—H46117.2
C9—C7—C10115.0 (18)N3—C25—C26109.1 (18)
C7—C9—H31109.5N3—C25—C27109.9 (19)
C7—C9—H32109.5C26—C25—C27108 (2)
H31—C9—H32109.2N3—C25—C28107.5 (17)
C7—C9—H33109.7C26—C25—C28109 (2)
H31—C9—H33109.6C27—C25—C28113.6 (19)
H32—C9—H33109.4C25—C26—H53109.1
C7—C10—O11117 (2)C25—C26—H54110.1
C7—C10—C12113 (2)H53—C26—H54109.5
O11—C10—C12130 (3)C25—C26—H55109.1
C10—C12—H34109.3H53—C26—H55109.4
C10—C12—H35109.5H54—C26—H55109.6
H34—C12—H35109.5C25—C27—H50109.3
C10—C12—H36109.5C25—C27—H51109.8
H34—C12—H36109.5H50—C27—H51109.4
H35—C12—H36109.5C25—C27—H52109.7
C5—C13—C14122.9 (16)H50—C27—H52109.2
C5—C13—C18117.7 (18)H51—C27—H52109.4
C14—C13—C18119 (2)C25—C28—H47110.5
C13—C14—C15123 (2)C25—C28—H48109.1
C13—C14—H37118.3H47—C28—H48109.3
C15—C14—H37118.4C25—C28—H49108.8
C14—C15—C16117 (2)H47—C28—H49109.6
C14—C15—H38121.5H48—C28—H49109.6
C16—C15—H38121.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H30···O6i0.982.223.18 (2)163
C28—H48···O11ii0.962.713.57 (3)151
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2.
(V) (2R,4R,5S)-3-tert-butyl-2-[(1R)-1-methyl-2-oxo- propyl]-4,5-diphenyl-[1,3,2]-oxazaphospholidine2-oxide top
Crystal data top
C22H28NO3PF(000) = 824
Mr = 385.44Dx = 1.225 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.109 (3) Åθ = 6–11°
b = 14.047 (3) ŵ = 0.15 mm1
c = 13.206 (6) ÅT = 175 K
β = 111.48 (3)°Needle, translucent pale white
V = 2090.3 (12) Å30.50 × 0.06 × 0.04 mm
Z = 4
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.018
Graphite monochromatorθmax = 22.0°, θmin = 2.2°
ω/2θ scansh = 012
Absorption correction: ψ scan
?
k = 014
Tmin = 0.84, Tmax = 0.92l = 1312
2836 measured reflections3 standard reflections every 60 min
2561 independent reflections intensity decay: 0.5%
1019 reflections with I > 2.0σ(I)
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.065 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 1.36 0.232 0.960
S = 1.14(Δ/σ)max = 0.006
1019 reflectionsΔρmax = 0.44 e Å3
244 parametersΔρmin = 0.30 e Å3
0 restraints
Crystal data top
C22H28NO3PV = 2090.3 (12) Å3
Mr = 385.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.109 (3) ŵ = 0.15 mm1
b = 14.047 (3) ÅT = 175 K
c = 13.206 (6) Å0.50 × 0.06 × 0.04 mm
β = 111.48 (3)°
Data collection top
Enraf-Nonius CAD4
diffractometer
1019 reflections with I > 2.0σ(I)
Absorption correction: ψ scan
?
Rint = 0.018
Tmin = 0.84, Tmax = 0.92θmax = 22.0°
2836 measured reflections3 standard reflections every 60 min
2561 independent reflections intensity decay: 0.5%
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.065H-atom parameters constrained
S = 1.14Δρmax = 0.44 e Å3
1019 reflectionsΔρmin = 0.30 e Å3
244 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1346 (5)0.2809 (4)0.3581 (4)0.0391
P20.1103 (2)0.16993 (18)0.3591 (2)0.0407
N30.1662 (6)0.1411 (4)0.2664 (5)0.0409
C40.2351 (7)0.2219 (6)0.2473 (6)0.0371
C50.1687 (8)0.3096 (6)0.2692 (6)0.0359
O60.1603 (5)0.1267 (4)0.4669 (5)0.0571
C70.1780 (9)0.0419 (7)0.2290 (8)0.0532
C80.2793 (16)0.0080 (9)0.3124 (14)0.1773
C90.188 (2)0.0466 (9)0.1231 (14)0.1943
C100.0692 (14)0.0156 (8)0.2208 (13)0.1206
C110.0519 (8)0.1583 (6)0.3063 (7)0.0445
C120.1133 (8)0.2097 (7)0.1988 (7)0.0626
C130.0941 (8)0.1913 (8)0.3973 (8)0.0528
O140.1316 (6)0.2721 (6)0.3943 (7)0.0813
C150.0911 (9)0.1221 (7)0.4827 (8)0.0560
C160.3657 (8)0.2233 (6)0.3119 (7)0.0402
C170.4442 (9)0.2519 (6)0.2630 (8)0.0490
C180.5637 (10)0.2615 (7)0.3213 (10)0.0594
C190.6091 (10)0.2415 (7)0.4306 (10)0.0652
C200.5333 (10)0.2100 (8)0.4789 (9)0.0662
C210.4142 (9)0.2006 (5)0.4235 (8)0.0450
C220.2429 (8)0.3995 (6)0.2968 (7)0.0403
C230.2729 (8)0.4428 (6)0.2180 (8)0.0484
C240.3450 (8)0.5227 (7)0.2434 (8)0.0521
C250.3845 (8)0.5608 (7)0.3463 (9)0.0564
C260.3548 (9)0.5180 (7)0.4250 (8)0.0609
C270.2825 (8)0.4371 (7)0.4003 (9)0.0536
H280.35500.02760.31920.1674*
H290.28780.07480.28480.1674*
H300.26990.01170.38150.1674*
H310.26170.08550.13030.2534*
H320.19760.01810.09620.2534*
H330.11760.07890.07040.2534*
H340.07210.08300.19430.1491*
H350.00420.01570.16400.1491*
H360.05600.01830.29080.1491*
H370.08280.19010.14140.0704*
H380.09440.28200.21260.0704*
H390.20110.20340.17160.0704*
H400.07750.08800.28390.0608*
H440.09750.32680.19880.0520*
H450.23760.21700.17220.0492*
H460.35790.17680.46090.0504*
H470.56830.19060.56120.0794*
H480.69740.25430.47480.0826*
H490.62100.28080.28180.0699*
H500.41090.26630.18170.0638*
H510.24470.41470.14010.0540*
H520.36700.55610.18240.0606*
H530.44040.61730.36520.0683*
H540.38350.54620.50050.0635*
H550.26240.40410.46000.0613*
H430.13750.06000.44750.0500*
H410.10550.15450.54360.0500*
H420.00700.10120.52070.0749*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.041 (4)0.038 (4)0.042 (3)0.005 (3)0.019 (3)0.006 (3)
P20.0485 (17)0.0396 (16)0.0353 (15)0.0072 (14)0.0170 (12)0.0023 (13)
N30.064 (5)0.029 (5)0.041 (4)0.010 (4)0.032 (4)0.010 (4)
C40.047 (6)0.035 (5)0.032 (5)0.003 (5)0.018 (5)0.011 (4)
C50.043 (6)0.040 (6)0.020 (5)0.013 (4)0.006 (4)0.002 (4)
O60.054 (4)0.078 (5)0.040 (4)0.020 (3)0.018 (3)0.014 (3)
C70.070 (7)0.038 (6)0.069 (7)0.003 (5)0.047 (6)0.007 (5)
C80.223 (19)0.059 (9)0.175 (17)0.070 (11)0.015 (15)0.048 (10)
C90.44 (3)0.052 (8)0.193 (17)0.088 (14)0.24 (2)0.072 (10)
C100.201 (16)0.050 (8)0.171 (14)0.029 (9)0.138 (13)0.038 (9)
C110.054 (6)0.036 (6)0.050 (6)0.026 (5)0.027 (5)0.009 (5)
C120.045 (6)0.076 (8)0.055 (7)0.019 (6)0.005 (5)0.015 (6)
C130.038 (6)0.053 (7)0.068 (8)0.010 (5)0.020 (6)0.003 (5)
O140.091 (6)0.050 (5)0.132 (7)0.010 (5)0.075 (6)0.020 (5)
C150.063 (7)0.059 (7)0.055 (6)0.009 (5)0.033 (6)0.000 (5)
C160.046 (6)0.032 (5)0.053 (6)0.007 (5)0.030 (5)0.002 (5)
C170.045 (7)0.044 (7)0.053 (6)0.002 (4)0.012 (5)0.009 (5)
C180.056 (8)0.060 (7)0.075 (8)0.007 (5)0.040 (7)0.004 (6)
C190.052 (8)0.061 (8)0.076 (9)0.015 (6)0.016 (7)0.018 (7)
C200.044 (8)0.085 (9)0.064 (7)0.011 (6)0.012 (6)0.020 (6)
C210.058 (8)0.041 (6)0.042 (6)0.009 (5)0.025 (5)0.008 (5)
C220.051 (6)0.045 (6)0.020 (5)0.011 (5)0.007 (5)0.006 (5)
C230.060 (7)0.036 (6)0.043 (6)0.009 (5)0.011 (5)0.008 (5)
C240.055 (7)0.049 (7)0.050 (7)0.007 (5)0.017 (5)0.003 (6)
C250.052 (7)0.041 (6)0.074 (8)0.014 (5)0.021 (6)0.001 (6)
C260.072 (8)0.053 (7)0.044 (6)0.017 (6)0.004 (6)0.015 (5)
C270.060 (7)0.051 (7)0.061 (7)0.006 (6)0.036 (6)0.003 (6)
Geometric parameters (Å, º) top
O1—P21.587 (6)C12—H390.994
O1—C51.437 (9)C13—O141.218 (10)
P2—N31.652 (7)C13—C151.479 (12)
P2—O61.459 (6)C15—H431.050
P2—C111.836 (9)C15—H410.994
N3—C41.484 (10)C15—H421.000
N3—C71.502 (11)C16—C171.389 (11)
C4—C51.554 (11)C16—C211.409 (12)
C4—C161.497 (11)C17—C181.374 (13)
C4—H451.006C17—H501.020
C5—C221.515 (11)C18—C191.373 (13)
C5—H441.039C18—H491.045
C7—C81.490 (16)C19—C201.368 (13)
C7—C91.448 (15)C19—H481.029
C7—C101.515 (14)C20—C211.363 (12)
C8—H281.019C20—H471.049
C8—H291.026C21—H461.034
C8—H300.962C22—C231.365 (11)
C9—H311.024C22—C271.377 (12)
C9—H320.999C23—C241.386 (12)
C9—H330.988C23—H511.036
C10—H341.015C24—C251.374 (13)
C10—H351.028C24—H521.047
C10—H360.993C25—C261.357 (13)
C11—C121.522 (11)C25—H531.013
C11—C131.540 (13)C26—C271.398 (12)
C11—H401.044C26—H541.009
C12—H370.996C27—H551.019
C12—H381.042
P2—O1—C5113.1 (5)C11—C12—H37112.8
O1—P2—N396.1 (3)C11—C12—H38107.4
O1—P2—O6113.9 (4)H37—C12—H38106.5
N3—P2—O6119.0 (4)C11—C12—H39112.8
O1—P2—C11105.1 (4)H37—C12—H39110.3
N3—P2—C11111.6 (4)H38—C12—H39106.7
O6—P2—C11109.7 (4)C11—C13—O14118.8 (9)
P2—N3—C4110.3 (5)C11—C13—C15118.3 (9)
P2—N3—C7125.8 (5)O14—C13—C15122.8 (10)
C4—N3—C7121.8 (6)C13—C15—H43110.4
N3—C4—C5102.3 (6)C13—C15—H41110.7
N3—C4—C16117.1 (8)H43—C15—H41121.0
C5—C4—C16113.2 (7)C13—C15—H42108.1
N3—C4—H45109.7H43—C15—H42105.1
C5—C4—H45116.3H41—C15—H42100.1
C16—C4—H4599.0C4—C16—C17119.9 (8)
C4—C5—O1104.7 (6)C4—C16—C21122.8 (8)
C4—C5—C22113.8 (7)C17—C16—C21117.2 (9)
O1—C5—C22111.0 (6)C16—C17—C18121.8 (9)
C4—C5—H44109.5C16—C17—H50118.2
O1—C5—H44113.9C18—C17—H50120.0
C22—C5—H44104.2C17—C18—C19120.2 (10)
N3—C7—C8110.1 (9)C17—C18—H49120.1
N3—C7—C9109.1 (8)C19—C18—H49119.6
C8—C7—C9113.5 (12)C18—C19—C20118.5 (10)
N3—C7—C10109.5 (7)C18—C19—H48119.6
C8—C7—C10105.2 (11)C20—C19—H48121.8
C9—C7—C10109.4 (12)C19—C20—C21122.7 (11)
C7—C8—H28107.8C19—C20—H47118.8
C7—C8—H29109.3C21—C20—H47118.5
H28—C8—H29106.0C16—C21—C20119.5 (9)
C7—C8—H30112.0C16—C21—H46118.5
H28—C8—H30111.0C20—C21—H46122.0
H29—C8—H30110.4C5—C22—C23119.2 (8)
C7—C9—H31108.2C5—C22—C27121.3 (8)
C7—C9—H32111.4C23—C22—C27119.5 (9)
H31—C9—H32107.7C22—C23—C24119.8 (9)
C7—C9—H33110.4C22—C23—H51120.3
H31—C9—H33108.5C24—C23—H51119.9
H32—C9—H33110.6C23—C24—C25121.0 (10)
C7—C10—H34112.5C23—C24—H52119.4
C7—C10—H35108.7C25—C24—H52119.5
H34—C10—H35106.1C24—C25—C26119.4 (9)
C7—C10—H36112.6C24—C25—H53120.5
H34—C10—H36108.8C26—C25—H53120.0
H35—C10—H36107.7C25—C26—C27120.0 (9)
P2—C11—C12113.7 (6)C25—C26—H54119.4
P2—C11—C13106.9 (6)C27—C26—H54120.6
C12—C11—C13113.4 (8)C26—C27—C22120.3 (9)
P2—C11—H40110.9C26—C27—H55119.7
C12—C11—H40101.1C22—C27—H55119.9
C13—C11—H40110.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H51···O6i1.042.213.240 (12)170
C10—H34···O14ii1.012.583.552 (16)161
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2.
(VI) (2R,4S,5R)-3-tert-butyl-2-benzyl-4,5-diphenyl- [1,3,2]-oxazaphospholidine2-oxide top
Crystal data top
C25H28NO2PF(000) = 864
Mr = 405.48Dx = 1.103 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23 reflections
a = 10.284 (2) Åθ = 10.1–16.2°
b = 21.262 (4) ŵ = 0.13 mm1
c = 12.768 (2) ÅT = 175 K
β = 119.04 (2)°Needle, translucent pale white
V = 2440.9 (9) Å30.37 × 0.07 × 0.04 mm
Z = 4
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.04
Graphite monochromatorθmax = 22.0°, θmin = 2.1°
ω/2θ scansh = 1010
Absorption correction: ψ scan
?
k = 210
Tmin = 0.81, Tmax = 0.91l = 912
2619 measured reflections3 standard reflections every 0 reflections
2576 independent reflections intensity decay: 0.4%
1037 reflections with I > 2.0σ(I)
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.091 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 17.0 7.24 12.9 7.66 1.45
S = 1.16(Δ/σ)max = 0.000081
1037 reflectionsΔρmax = 0.46 e Å3
132 parametersΔρmin = 0.52 e Å3
19 restraints
Crystal data top
C25H28NO2PV = 2440.9 (9) Å3
Mr = 405.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.284 (2) ŵ = 0.13 mm1
b = 21.262 (4) ÅT = 175 K
c = 12.768 (2) Å0.37 × 0.07 × 0.04 mm
β = 119.04 (2)°
Data collection top
Enraf-Nonius CAD4
diffractometer
1037 reflections with I > 2.0σ(I)
Absorption correction: ψ scan
?
Rint = 0.04
Tmin = 0.81, Tmax = 0.91θmax = 22.0°
2619 measured reflections3 standard reflections every 0 reflections
2576 independent reflections intensity decay: 0.4%
Refinement top
R[F2 > 2σ(F2)] = 0.08519 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.16Δρmax = 0.46 e Å3
1037 reflectionsΔρmin = 0.52 e Å3
132 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8002 (8)0.0350 (3)0.6399 (8)0.0321
P20.6633 (3)0.08665 (14)0.5753 (3)0.0246
N30.7835 (10)0.1483 (4)0.6371 (8)0.026 (3)*
C40.9529 (12)0.1281 (5)0.7093 (8)0.025 (3)*
C50.9364 (12)0.0603 (5)0.6500 (11)0.023 (3)*
O60.5496 (8)0.0837 (4)0.4280 (7)0.0317
C70.7392 (12)0.2114 (5)0.5688 (10)0.022 (3)*
C80.8529 (13)0.2599 (5)0.6696 (11)0.030 (3)*
C90.7382 (14)0.2116 (6)0.4434 (12)0.038 (3)*
C100.5789 (12)0.2293 (6)0.5374 (11)0.030 (3)*
C110.5700 (12)0.0688 (5)0.6634 (11)0.027 (3)*
C120.4261 (11)0.1119 (5)0.6198 (8)0.024 (3)*
C130.2991 (10)0.1080 (5)0.5022 (9)0.026 (3)*
C140.1754 (13)0.1481 (5)0.4626 (11)0.043 (4)*
C150.1901 (13)0.1906 (6)0.5526 (9)0.039 (4)*
C160.3141 (11)0.1926 (6)0.6716 (10)0.036 (3)*
C170.4374 (12)0.1522 (5)0.7126 (10)0.033 (3)*
C181.0752 (12)0.0169 (5)0.7358 (9)0.026 (3)*
C191.1034 (13)0.0132 (5)0.8432 (9)0.032 (3)*
C201.2290 (11)0.0492 (5)0.9196 (11)0.038 (4)*
C211.3397 (14)0.0548 (6)0.8862 (11)0.045 (4)*
C221.3141 (13)0.0253 (6)0.7786 (10)0.046 (4)*
C231.1868 (11)0.0107 (6)0.7037 (11)0.035 (3)*
C241.0479 (10)0.1345 (5)0.8555 (8)0.021 (3)*
C250.9904 (13)0.1347 (5)0.9367 (9)0.032 (3)*
C261.0755 (11)0.1353 (5)1.0652 (9)0.033 (3)*
C271.2335 (11)0.1358 (6)1.1331 (12)0.038 (4)*
C281.2958 (15)0.1383 (6)1.0567 (10)0.048 (4)*
C291.2069 (10)0.1369 (5)0.9282 (9)0.030 (3)*
H570.92760.06400.56970.0312*
H581.00410.15360.67740.0302*
H320.83230.30230.63900.0386*
H310.95330.24970.68980.0386*
H300.84450.25810.74140.0386*
H370.71120.25240.40650.0468*
H380.83560.20130.45630.0468*
H360.66900.18100.38990.0468*
H350.55410.26910.49630.0369*
H330.57250.23240.61010.0369*
H340.51050.19800.48570.0369*
H510.63840.07520.74780.0344*
H500.53910.02510.64890.0344*
H560.29760.07780.44900.0327*
H550.09360.14660.38590.0492*
H530.31440.22210.72550.0440*
H520.51530.15200.79020.0385*
H451.03100.00860.86610.0432*
H461.23840.06830.98840.0504*
H471.42660.07690.93300.0559*
H491.17660.03010.63440.0426*
H390.88780.13440.90300.0409*
H411.28900.13481.21610.0452*
H431.39840.14101.09080.0538*
H401.02330.13551.10750.0389*
H441.25810.13780.88490.0391*
H481.38630.03000.75530.0568*
H540.11320.21900.53260.0515*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.020 (5)0.010 (4)0.059 (6)0.004 (3)0.013 (5)0.002 (4)
P20.0208 (18)0.0154 (15)0.036 (2)0.0010 (16)0.0123 (17)0.0005 (17)
O60.040 (5)0.028 (5)0.035 (6)0.000 (4)0.024 (5)0.002 (4)
Geometric parameters (Å, º) top
O1—P21.655 (8)C13—H560.929
O1—C51.447 (13)C14—C151.413 (9)
P2—N31.710 (10)C14—H550.931
P2—O61.665 (9)C15—C161.434 (9)
P2—C111.837 (11)C15—H540.927
N3—C41.585 (14)C16—C171.406 (9)
N3—C71.542 (14)C16—H530.930
C4—C51.599 (15)C17—H520.923
C4—C241.640 (9)C18—C191.409 (9)
C4—H580.972C18—C231.400 (9)
C5—C181.604 (15)C19—C201.409 (9)
C5—H570.987C19—H450.928
C7—C81.621 (15)C20—C211.401 (9)
C7—C91.597 (17)C20—H460.929
C7—C101.544 (15)C21—C221.413 (9)
C8—H320.964C21—H470.927
C8—H310.960C22—C231.413 (9)
C8—H300.962C22—H480.930
C9—H370.960C23—H490.936
C9—H380.958C24—C251.420 (9)
C9—H360.961C24—C291.436 (9)
C10—H350.962C25—C261.437 (9)
C10—H330.964C25—H390.927
C10—H340.960C26—C271.423 (9)
C11—C121.594 (14)C26—H400.928
C11—H510.969C27—C281.404 (9)
C11—H500.969C27—H410.928
C12—C131.437 (9)C28—C291.440 (9)
C12—C171.420 (9)C28—H430.928
C13—C141.405 (9)C29—H440.931
P2—O1—C5110.5 (6)C11—C12—C17111.7 (8)
O1—P2—N391.6 (4)C13—C12—C17124.8 (10)
O1—P2—O6120.0 (5)C12—C13—C14123.1 (10)
N3—P2—O6120.2 (5)C12—C13—H56119.2
O1—P2—C1197.3 (5)C14—C13—H56117.6
N3—P2—C11110.6 (5)C13—C14—C15112.0 (11)
O6—P2—C11113.3 (5)C13—C14—H55123.8
P2—N3—C4113.9 (7)C15—C14—H55124.1
P2—N3—C7117.2 (7)C14—C15—C16124.7 (12)
C4—N3—C7120.3 (8)C14—C15—H54116.9
N3—C4—C597.8 (7)C16—C15—H54118.3
N3—C4—C24121.3 (8)C15—C16—C17123.6 (12)
C5—C4—C24118.8 (9)C15—C16—H53119.0
N3—C4—H58105.8C17—C16—H53117.3
C5—C4—H58105.0C12—C17—C16111.4 (10)
C24—C4—H58106.6C12—C17—H52124.8
C4—C5—O1104.6 (8)C16—C17—H52123.8
C4—C5—C18109.9 (9)C5—C18—C19128.3 (9)
O1—C5—C18110.5 (9)C5—C18—C23116.0 (9)
C4—C5—H57110.7C19—C18—C23115.5 (11)
O1—C5—H57110.0C18—C19—C20127.4 (12)
C18—C5—H57111.0C18—C19—H45116.2
N3—C7—C8101.7 (9)C20—C19—H45116.4
N3—C7—C9115.3 (9)C19—C20—C21116.2 (12)
C8—C7—C9116.4 (9)C19—C20—H46122.1
N3—C7—C10110.3 (9)C21—C20—H46121.7
C8—C7—C10108.5 (9)C20—C21—C22117.6 (12)
C9—C7—C10104.6 (9)C20—C21—H47121.2
C7—C8—H32109.9C22—C21—H47121.3
C7—C8—H31109.7C21—C22—C23124.9 (12)
H32—C8—H31108.5C21—C22—H48117.5
C7—C8—H30111.5C23—C22—H48117.6
H32—C8—H30108.6C22—C23—C18118.3 (11)
H31—C8—H30108.5C22—C23—H49121.4
C7—C9—H37110.7C18—C23—H49120.2
C7—C9—H38109.2C4—C24—C25127.0 (9)
H37—C9—H38108.7C4—C24—C29126.9 (9)
C7—C9—H36110.6C25—C24—C29106.0 (9)
H37—C9—H36108.9C24—C25—C26126.5 (11)
H38—C9—H36108.6C24—C25—H39116.5
C7—C10—H35109.0C26—C25—H39117.0
C7—C10—H33109.2C25—C26—C27125.3 (12)
H35—C10—H33110.0C25—C26—H40117.5
C7—C10—H34109.9C27—C26—H40117.2
H35—C10—H34108.8C26—C27—C28110.4 (12)
H33—C10—H34109.8C26—C27—H41125.7
P2—C11—C12109.8 (7)C28—C27—H41123.9
P2—C11—H51109.9C27—C28—C29122.6 (13)
C12—C11—H51110.9C27—C28—H43118.4
P2—C11—H50107.6C29—C28—H43119.0
C12—C11—H50108.7C28—C29—C24129.1 (11)
H51—C11—H50109.9C28—C29—H44116.6
C11—C12—C13123.4 (9)C24—C29—H44114.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H50···O6i0.972.513.463 (14)169
C13—H56···O1i0.932.643.432 (13)143
Symmetry code: (i) x+1, y, z+1.
(VII) (2R,3S,5S)-3,5-diphenyl-2-(4-methoxyphenyl)- [1,4,2]-oxazaphosphorinane2-oxide top
Crystal data top
C22H22NO3PF(000) = 400
Mr = 379.40Dx = 1.316 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5384 reflections
a = 10.0104 (3) Åθ = 3.0–32.2°
b = 8.1056 (1) ŵ = 0.17 mm1
c = 12.5372 (3) ÅT = 175 K
β = 109.717 (5)°Prism, translucent pale white
V = 957.63 (5) Å30.32 × 0.30 × 0.20 mm
Z = 2
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
3438 reflections with I > 2.0σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.028
Graphite monochromatorθmax = 32.2°, θmin = 3.3°
ω scansh = 1414
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1112
Tmin = 0.952, Tmax = 0.967l = 1818
12688 measured reflectionsStandard reflections: 4 frames; every 25 frames reflections
5435 independent reflections intensity decay: none
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 18.4 -27.6 15.3 -5.81
wR(F2) = 0.046(Δ/σ)max = 0.000432
S = 1.11Δρmax = 0.23 e Å3
3438 reflectionsΔρmin = 0.31 e Å3
245 parametersAbsolute structure: Flack (1983), 2104 Friedel-pairs
1 restraintAbsolute structure parameter: 0.18 (12)
Primary atom site location: structure-invariant direct methods
Crystal data top
C22H22NO3PV = 957.63 (5) Å3
Mr = 379.40Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.0104 (3) ŵ = 0.17 mm1
b = 8.1056 (1) ÅT = 175 K
c = 12.5372 (3) Å0.32 × 0.30 × 0.20 mm
β = 109.717 (5)°
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
3438 reflections with I > 2.0σ(I)
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Rint = 0.028
Tmin = 0.952, Tmax = 0.967Standard reflections: 4 frames; every 25 frames reflections
12688 measured reflections intensity decay: none
5435 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.046Δρmax = 0.23 e Å3
S = 1.11Δρmin = 0.31 e Å3
3438 reflectionsAbsolute structure: Flack (1983), 2104 Friedel-pairs
245 parametersAbsolute structure parameter: 0.18 (12)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0586 (2)0.3623 (3)0.70204 (17)0.0324
P20.17060 (7)0.29948 (12)0.64536 (6)0.0264
C30.0934 (3)0.1060 (4)0.5795 (2)0.0249
N40.0470 (2)0.0104 (3)0.66095 (18)0.0252
C50.0662 (3)0.0962 (4)0.6903 (2)0.0277
C60.0044 (3)0.2494 (4)0.7600 (3)0.0344
O70.1877 (2)0.4236 (3)0.56487 (17)0.0359
C80.3354 (3)0.2597 (3)0.7574 (2)0.0232
C90.4500 (3)0.3598 (4)0.7613 (2)0.0275
C100.5794 (3)0.3441 (4)0.8479 (2)0.0306
C110.5949 (3)0.2265 (4)0.9319 (2)0.0292
C120.4836 (3)0.1235 (4)0.9289 (2)0.0286
C130.3545 (3)0.1402 (3)0.8415 (2)0.0282
O140.7256 (2)0.2236 (3)1.01393 (18)0.0428
C150.7473 (4)0.1052 (5)1.1036 (3)0.0508
C160.1243 (3)0.0169 (4)0.7597 (2)0.0299
C170.2701 (3)0.0354 (4)0.7342 (3)0.0381
C180.3220 (4)0.1385 (5)0.8005 (3)0.0487
C190.2307 (4)0.2228 (5)0.8906 (3)0.0516
C200.0846 (4)0.2057 (6)0.9169 (3)0.0466
C210.0332 (3)0.1028 (4)0.8517 (3)0.0370
C220.1987 (3)0.0132 (4)0.5395 (2)0.0250
C230.2648 (3)0.1298 (4)0.5915 (2)0.0312
C240.3631 (3)0.2097 (5)0.5538 (3)0.0385
C250.3984 (3)0.1446 (4)0.4645 (3)0.0369
C260.3319 (3)0.0031 (4)0.4109 (3)0.0356
C270.2325 (3)0.0744 (4)0.4476 (2)0.0316
H280.08280.30700.77540.0439*
H290.06750.21390.83150.0439*
H300.14350.12710.61990.0330*
H310.01650.08800.62250.0500*
H320.01030.13770.51400.0327*
H330.27830.06900.83860.0344*
H340.49480.04180.98510.0348*
H350.65490.41410.84930.0364*
H360.43850.44100.70480.0340*
H370.68200.12911.14330.0564*
H380.84380.11681.15430.0564*
H390.73380.00691.07280.0564*
H400.33200.02110.67270.0459*
H410.42050.14790.78320.0656*
H420.26640.29170.93470.0614*
H430.02100.26390.97870.0601*
H440.06460.08990.86960.0441*
H450.24430.17310.65340.0366*
H460.40390.30740.58830.0486*
H470.46800.19830.44130.0471*
H480.35380.04090.34890.0466*
H490.18660.17070.41060.0395*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (10)0.0273 (10)0.0379 (11)0.0056 (9)0.0094 (9)0.0018 (9)
P20.0260 (3)0.0255 (3)0.0239 (3)0.0013 (4)0.0031 (2)0.0023 (3)
C30.0255 (13)0.0306 (15)0.0185 (11)0.0032 (11)0.0073 (10)0.0003 (10)
N40.0274 (12)0.0297 (12)0.0217 (11)0.0031 (10)0.0122 (9)0.0037 (9)
C50.0211 (13)0.0363 (16)0.0234 (13)0.0019 (12)0.0046 (10)0.0010 (12)
C60.0340 (15)0.0398 (18)0.0292 (14)0.0029 (13)0.0104 (12)0.0019 (12)
O70.0367 (12)0.0344 (11)0.0317 (11)0.0001 (10)0.0052 (9)0.0100 (9)
C80.0245 (12)0.0247 (15)0.0184 (11)0.0004 (10)0.0048 (9)0.0027 (9)
C90.0294 (13)0.0276 (13)0.0258 (13)0.0014 (12)0.0097 (11)0.0053 (11)
C100.0248 (13)0.0321 (16)0.0343 (14)0.0052 (11)0.0093 (11)0.0066 (11)
C110.0263 (14)0.0318 (15)0.0245 (13)0.0003 (12)0.0022 (10)0.0013 (11)
C120.0300 (14)0.0282 (15)0.0263 (13)0.0028 (12)0.0077 (11)0.0068 (11)
C130.0293 (15)0.0251 (14)0.0273 (14)0.0062 (12)0.0058 (11)0.0023 (11)
O140.0319 (12)0.0490 (14)0.0374 (12)0.0085 (11)0.0016 (9)0.0168 (11)
C150.049 (2)0.053 (2)0.0354 (17)0.0080 (18)0.0063 (15)0.0194 (16)
C160.0238 (13)0.0403 (17)0.0277 (14)0.0009 (12)0.0114 (11)0.0071 (12)
C170.0246 (14)0.049 (2)0.0413 (17)0.0015 (14)0.0119 (12)0.0060 (15)
C180.0351 (17)0.067 (2)0.051 (2)0.0172 (17)0.0226 (15)0.0189 (18)
C190.058 (2)0.062 (3)0.0475 (18)0.017 (2)0.0346 (17)0.0074 (18)
C200.0529 (19)0.057 (2)0.0348 (15)0.001 (2)0.0210 (14)0.0038 (19)
C210.0274 (15)0.055 (2)0.0309 (15)0.0008 (14)0.0123 (12)0.0044 (14)
C220.0262 (13)0.0278 (13)0.0207 (12)0.0046 (12)0.0077 (10)0.0039 (10)
C230.0319 (14)0.0341 (15)0.0300 (14)0.0013 (13)0.0137 (11)0.0068 (12)
C240.0398 (15)0.0362 (16)0.0426 (16)0.0095 (17)0.0180 (13)0.0048 (17)
C250.0365 (16)0.0368 (16)0.0431 (17)0.0012 (14)0.0209 (14)0.0065 (14)
C260.0403 (17)0.0374 (17)0.0354 (16)0.0070 (14)0.0213 (13)0.0020 (13)
C270.0376 (16)0.0303 (15)0.0289 (14)0.0028 (13)0.0140 (12)0.0017 (12)
Geometric parameters (Å, º) top
O1—P21.600 (2)O14—C151.438 (4)
O1—C61.440 (4)C15—H370.965
P2—C31.818 (3)C15—H380.965
P2—O71.475 (2)C15—H390.978
P2—C81.799 (3)C16—C171.393 (4)
C3—N41.476 (3)C16—C211.392 (4)
C3—C221.512 (4)C17—C181.396 (5)
C3—H320.986C17—H400.931
N4—C51.478 (4)C18—C191.372 (6)
N4—H310.928C18—H410.938
C5—C61.524 (4)C19—C201.394 (5)
C5—C161.509 (4)C19—H420.937
C5—H300.990C20—C211.383 (5)
C6—H280.987C20—H430.947
C6—H290.984C21—H440.933
C8—C91.393 (4)C22—C231.384 (4)
C8—C131.397 (4)C22—C271.397 (4)
C9—C101.387 (4)C23—C241.388 (4)
C9—H360.945C23—H450.935
C10—C111.390 (4)C24—C251.387 (4)
C10—H350.941C24—H460.929
C11—C121.382 (4)C25—C261.382 (5)
C11—O141.365 (3)C25—H470.947
C12—C131.390 (4)C26—C271.381 (4)
C12—H340.946C26—H480.945
C13—H330.948C27—H490.944
P2—O1—C6120.91 (19)C12—C13—H33119.6
O1—P2—C3102.82 (12)C11—O14—C15117.0 (3)
O1—P2—O7110.31 (13)O14—C15—H37108.6
C3—P2—O7114.03 (13)O14—C15—H38107.7
O1—P2—C8107.80 (12)H37—C15—H38110.0
C3—P2—C8109.70 (12)O14—C15—H39110.3
O7—P2—C8111.67 (13)H37—C15—H39111.2
P2—C3—N4108.90 (17)H38—C15—H39108.9
P2—C3—C22110.02 (18)C5—C16—C17120.7 (3)
N4—C3—C22112.7 (2)C5—C16—C21120.6 (3)
P2—C3—H32105.3C17—C16—C21118.7 (3)
N4—C3—H32109.8C16—C17—C18120.0 (3)
C22—C3—H32109.9C16—C17—H40119.4
C3—N4—C5111.8 (2)C18—C17—H40120.7
C3—N4—H31102.5C17—C18—C19120.7 (3)
C5—N4—H31112.8C17—C18—H41119.0
N4—C5—C6109.2 (2)C19—C18—H41120.3
N4—C5—C16109.6 (2)C18—C19—C20120.0 (3)
C6—C5—C16109.0 (2)C18—C19—H42120.2
N4—C5—H30109.3C20—C19—H42119.9
C6—C5—H30110.4C19—C20—C21119.4 (3)
C16—C5—H30109.3C19—C20—H43120.5
C5—C6—O1113.0 (2)C21—C20—H43120.2
C5—C6—H28107.6C16—C21—C20121.4 (3)
O1—C6—H28108.1C16—C21—H44119.0
C5—C6—H29108.3C20—C21—H44119.6
O1—C6—H29109.6C3—C22—C23122.4 (2)
H28—C6—H29110.2C3—C22—C27119.1 (3)
P2—C8—C9116.75 (19)C23—C22—C27118.4 (3)
P2—C8—C13124.7 (2)C22—C23—C24120.8 (3)
C9—C8—C13118.5 (2)C22—C23—H45120.1
C8—C9—C10120.9 (2)C24—C23—H45119.1
C8—C9—H36119.3C23—C24—C25120.0 (3)
C10—C9—H36119.7C23—C24—H46119.4
C9—C10—C11119.5 (3)C25—C24—H46120.6
C9—C10—H35119.5C24—C25—C26119.8 (3)
C11—C10—H35121.0C24—C25—H47119.2
C10—C11—C12120.7 (2)C26—C25—H47121.1
C10—C11—O14114.6 (3)C25—C26—C27119.9 (3)
C12—C11—O14124.7 (3)C25—C26—H48120.4
C11—C12—C13119.3 (3)C27—C26—H48119.7
C11—C12—H34120.7C22—C27—C26121.1 (3)
C13—C12—H34120.0C22—C27—H49119.1
C8—C13—C12121.1 (3)C26—C27—H49119.9
C8—C13—H33119.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H31···O7i0.932.543.089 (3)118
C3—H32···O7i0.992.573.153 (4)118
C21—H44···O14ii0.932.603.286 (4)131
Symmetry codes: (i) x, y1/2, z+1; (ii) x+1, y1/2, z+2.
(VIII) (2S,3S,5S)-2,3,5-triphenyl-[1,4,2]-oxazaphosphorinane 2-oxide top
Crystal data top
C21H20NO2PF(000) = 736
Mr = 349.37Dx = 1.184 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 0 reflections
a = 5.6212 (6) Åθ = 0–0°
b = 25.714 (2) ŵ = 0.15 mm1
c = 13.561 (2) ÅT = 175 K
V = 1960.2 (4) Å3Needle, translucent pale white
Z = 40.33 × 0.05 × 0.05 mm
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
6347 independent reflections
Radiation source: Enhance (Mo) X-ray Source496 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.203
Detector resolution: 8.4205 pixels mm-1θmax = 32.5°, θmin = 2.8°
ω scansh = 87
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 3738
Tmin = 0.91, Tmax = 0.99l = 2019
33616 measured reflections
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.131 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 11.7 3.40 8.76 4.60 0.792
wR(F2) = 0.119(Δ/σ)max = 0.000049
S = 1.00Δρmax = 1.86 e Å3
496 reflectionsΔρmin = 0.51 e Å3
87 parametersAbsolute structure: Flack (1983), 2610 Friedel-pairs
6 restraintsAbsolute structure parameter: 0.0 (15)
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H20NO2PV = 1960.2 (4) Å3
Mr = 349.37Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.6212 (6) ŵ = 0.15 mm1
b = 25.714 (2) ÅT = 175 K
c = 13.561 (2) Å0.33 × 0.05 × 0.05 mm
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
6347 independent reflections
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
496 reflections with I > 2.0σ(I)
Tmin = 0.91, Tmax = 0.99Rint = 0.203
33616 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.131H-atom parameters constrained
wR(F2) = 0.119Δρmax = 1.86 e Å3
S = 1.00Δρmin = 0.51 e Å3
496 reflectionsAbsolute structure: Flack (1983), 2610 Friedel-pairs
87 parametersAbsolute structure parameter: 0.0 (15)
6 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.284 (3)0.2630 (8)0.093 (2)0.038 (7)*
P20.360 (2)0.2893 (4)0.1912 (9)0.040 (3)*
C30.152 (7)0.3456 (12)0.203 (3)0.029 (9)*
N40.196 (4)0.3761 (11)0.097 (3)0.042 (9)*
C50.150 (8)0.3409 (12)0.014 (2)0.038 (10)*
C60.305 (6)0.2923 (14)0.001 (2)0.037 (11)*
O70.612 (4)0.3030 (7)0.2028 (16)0.034 (7)*
C80.171 (7)0.3688 (13)0.086 (3)0.048 (5)*
C90.021 (8)0.3699 (14)0.152 (3)0.048 (5)*
C100.003 (8)0.4002 (14)0.236 (2)0.048 (5)*
C110.199 (7)0.4324 (16)0.263 (3)0.048 (5)*
C120.384 (7)0.4341 (13)0.186 (3)0.048 (5)*
C130.355 (7)0.4047 (12)0.103 (3)0.048 (5)*
C140.194 (6)0.3792 (15)0.287 (3)0.038 (5)*
C150.394 (6)0.4102 (13)0.286 (2)0.037 (5)*
C160.433 (6)0.4410 (13)0.374 (2)0.038 (5)*
C170.248 (6)0.4412 (14)0.439 (3)0.038 (5)*
C180.060 (6)0.4115 (14)0.433 (2)0.037 (5)*
C190.036 (7)0.3810 (13)0.357 (3)0.038 (5)*
C200.265 (5)0.2455 (14)0.283 (2)0.041 (5)*
C210.050 (5)0.2184 (11)0.285 (2)0.041 (5)*
C220.005 (6)0.1824 (12)0.358 (2)0.041 (5)*
C230.131 (6)0.1807 (13)0.444 (2)0.041 (5)*
C240.349 (6)0.2066 (13)0.444 (2)0.041 (5)*
C250.409 (6)0.2392 (12)0.365 (2)0.041 (5)*
H260.25030.27200.05430.0390*
H270.47060.30190.00880.0390*
H280.01490.32850.01930.0490*
H290.22830.40880.09410.0450*
H300.01130.33210.20570.0350*
H310.15530.34990.14050.0600*
H320.13000.39920.27960.0600*
H330.20900.45070.32230.0600*
H340.51790.45500.19370.0600*
H350.47070.40760.05490.0600*
H360.50280.40990.23430.0600*
H370.56970.46080.38370.0600*
H380.25780.46350.49270.0600*
H390.05500.41270.48200.0600*
H400.09800.35990.35360.0600*
H410.06060.22450.23560.0600*
H420.13140.15950.34990.0600*
H430.07790.16290.49940.0600*
H440.45510.20210.49560.0600*
H450.55170.25760.36840.0600*
Geometric parameters (Å, º) top
O1—P21.56 (3)C12—H340.930
O1—C61.45 (4)C13—H350.931
P2—C31.87 (3)C14—C151.38 (4)
P2—O71.46 (2)C14—C191.30 (4)
P2—C201.76 (3)C15—C161.44 (4)
C3—N41.66 (5)C15—H360.932
C3—C141.45 (5)C16—C171.36 (4)
C3—H300.983C16—H370.931
N4—C51.46 (4)C17—C181.31 (4)
N4—H290.860C17—H380.932
C5—C61.53 (4)C18—C191.29 (4)
C5—C81.54 (5)C18—H390.931
C5—H280.984C19—H400.929
C6—H260.969C20—C211.394 (10)
C6—H270.970C20—C251.395 (10)
C8—C91.41 (5)C21—C221.389 (10)
C8—C131.40 (4)C21—H410.929
C9—C101.38 (4)C22—C231.392 (10)
C9—H310.930C22—H420.929
C10—C111.45 (5)C23—C241.396 (10)
C10—H320.926C23—H430.934
C11—C121.48 (5)C24—C251.392 (10)
C11—H330.929C24—H440.929
C12—C131.36 (4)C25—H450.931
P2—O1—C6119 (2)C11—C12—H34119.9
O1—P2—C3103.7 (15)C13—C12—H34121.4
O1—P2—O7117.5 (14)C8—C13—C12127 (4)
C3—P2—O7114.1 (14)C8—C13—H35116.6
O1—P2—C20104.2 (15)C12—C13—H35116.7
C3—P2—C20104.1 (17)C3—C14—C15118 (4)
O7—P2—C20111.9 (14)C3—C14—C19119 (3)
P2—C3—N4102 (2)C15—C14—C19123 (3)
P2—C3—C14115 (3)C14—C15—C16116 (3)
N4—C3—C14112 (3)C14—C15—H36122.6
P2—C3—H30108.4C16—C15—H36121.8
N4—C3—H30109.7C15—C16—C17115 (3)
C14—C3—H30109.3C15—C16—H37123.0
C3—N4—C5110 (3)C17—C16—H37122.3
C3—N4—H29121.9C16—C17—C18125 (4)
C5—N4—H29127.6C16—C17—H38117.7
N4—C5—C6119 (3)C18—C17—H38117.1
N4—C5—C8112 (3)C17—C18—C19119 (4)
C6—C5—C8104 (3)C17—C18—H39119.9
N4—C5—H28108.3C19—C18—H39120.9
C6—C5—H28106.2C14—C19—C18122 (4)
C8—C5—H28106.7C14—C19—H40119.4
C5—C6—O1106 (3)C18—C19—H40118.9
C5—C6—H26110.2P2—C20—C21127 (3)
O1—C6—H26111.0P2—C20—C25118 (2)
C5—C6—H27110.6C21—C20—C25115 (3)
O1—C6—H27109.3C20—C21—C22123 (3)
H26—C6—H27109.5C20—C21—H41118.6
C5—C8—C9121 (3)C22—C21—H41118.5
C5—C8—C13121 (4)C21—C22—C23119 (3)
C9—C8—C13116 (3)C21—C22—H42120.6
C8—C9—C10119 (4)C23—C22—H42120.0
C8—C9—H31120.1C22—C23—C24118 (3)
C10—C9—H31120.9C22—C23—H43120.9
C9—C10—C11126 (4)C24—C23—H43121.1
C9—C10—H32117.0C23—C24—C25120 (3)
C11—C10—H32117.0C23—C24—H44120.1
C10—C11—C12113 (3)C25—C24—H44119.9
C10—C11—H33123.8C20—C25—C24123 (3)
C12—C11—H33123.7C20—C25—H45118.4
C11—C12—C13119 (4)C24—C25—H45118.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H30···O7i0.982.253.23 (5)177
Symmetry code: (i) x1, y, z.
(IX) (2R,3S,5S)-3,5-diphenyl-[1,4,2]-oxazaphosphorinane 2-oxide. top
Crystal data top
C15H16NO2PF(000) = 576
Mr = 273.27Dx = 1.326 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2867 reflections
a = 5.3914 (2) Åθ = 2.8–32.4°
b = 11.7559 (4) ŵ = 0.20 mm1
c = 21.6032 (8) ÅT = 175 K
V = 1369.23 (9) Å3Prism, translucent pale white
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
4506 independent reflections
Radiation source: Enhance (Mo) X-ray Source1197 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 8.4205 pixels mm-1θmax = 32.5°, θmin = 3.3°
ω scansh = 87
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1716
Tmin = 0.940, Tmax = 0.961l = 3129
26882 measured reflections
Refinement top
Refinement on FHydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.028 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 27.8 -41.7 34.0 -14.2 6.83
wR(F2) = 0.029(Δ/σ)max = 0.014
S = 1.11Δρmax = 0.12 e Å3
1197 reflectionsΔρmin = 0.18 e Å3
173 parametersAbsolute structure: Flack (1983), 1866 Friedel-pairs
0 restraintsAbsolute structure parameter: 0.10 (16)
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H16NO2PV = 1369.23 (9) Å3
Mr = 273.27Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.3914 (2) ŵ = 0.20 mm1
b = 11.7559 (4) ÅT = 175 K
c = 21.6032 (8) Å0.30 × 0.20 × 0.20 mm
Data collection top
Oxford Diffraction XCALIBUR
diffractometer
4506 independent reflections
Absorption correction: multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
1197 reflections with I > 2.0σ(I)
Tmin = 0.940, Tmax = 0.961Rint = 0.057
26882 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.029Δρmax = 0.12 e Å3
S = 1.11Δρmin = 0.18 e Å3
1197 reflectionsAbsolute structure: Flack (1983), 1866 Friedel-pairs
173 parametersAbsolute structure parameter: 0.10 (16)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2584 (5)0.02455 (16)0.84333 (9)0.0464
P20.2897 (2)0.03856 (7)0.77056 (4)0.0449
C30.4148 (6)0.1804 (3)0.76198 (14)0.0349
N40.2608 (5)0.25689 (19)0.79954 (10)0.0345
C50.2697 (6)0.2298 (2)0.86558 (12)0.0365
C60.1378 (7)0.1162 (3)0.87593 (15)0.0407
O70.4345 (5)0.0532 (2)0.74238 (10)0.0629
C80.4170 (6)0.2124 (3)0.69417 (15)0.0359
C90.2314 (7)0.2759 (3)0.66782 (14)0.0398
C100.2332 (9)0.3003 (3)0.60526 (16)0.0509
C110.4257 (8)0.2620 (3)0.56872 (18)0.0545
C120.6093 (8)0.1980 (3)0.59410 (16)0.0523
C130.6079 (7)0.1737 (3)0.65689 (15)0.0449
C140.1392 (6)0.3206 (3)0.90303 (14)0.0356
C150.2224 (7)0.3493 (3)0.96196 (14)0.0420
C160.1000 (8)0.4300 (3)0.99651 (16)0.0475
C170.1063 (8)0.4844 (3)0.97243 (17)0.0492
C180.1890 (7)0.4578 (3)0.91430 (15)0.0478
C190.0676 (7)0.3747 (3)0.87953 (17)0.0438
H200.04730.04290.74670.0419*
H210.58480.18060.77820.0422*
H230.44260.22610.87960.0431*
H240.03470.12490.85970.0495*
H250.13730.09840.92010.0494*
H260.73320.13020.67350.0540*
H270.74020.17050.56990.0619*
H280.42640.27960.52640.0658*
H290.10640.34170.58820.0599*
H300.10300.30370.69230.0474*
H310.36510.31410.97670.0504*
H320.15620.44911.03660.0558*
H330.19230.53980.99520.0582*
H340.32630.49470.89750.0578*
H350.12540.35590.83990.0519*
H220.32760.34060.79510.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0721 (18)0.0329 (11)0.0340 (11)0.0117 (14)0.0004 (14)0.0039 (10)
P20.0662 (7)0.0338 (4)0.0345 (4)0.0085 (5)0.0050 (5)0.0013 (4)
C30.0274 (18)0.0393 (17)0.0380 (19)0.0005 (15)0.0024 (16)0.0008 (16)
N40.0400 (15)0.0321 (12)0.0315 (13)0.0005 (15)0.0057 (14)0.0017 (10)
C50.036 (2)0.0417 (17)0.0321 (16)0.0018 (19)0.0031 (18)0.0012 (14)
C60.054 (3)0.0385 (17)0.0293 (16)0.0063 (17)0.0032 (17)0.0054 (15)
O70.099 (2)0.0465 (14)0.0426 (15)0.0252 (16)0.0013 (14)0.0032 (12)
C80.038 (2)0.0387 (18)0.0305 (16)0.0066 (17)0.0003 (17)0.0006 (15)
C90.039 (2)0.0448 (17)0.0360 (17)0.005 (2)0.0028 (19)0.0015 (14)
C100.057 (3)0.052 (2)0.044 (2)0.002 (2)0.012 (2)0.0083 (17)
C110.067 (3)0.061 (2)0.036 (2)0.027 (2)0.006 (2)0.0077 (19)
C120.057 (3)0.061 (2)0.039 (2)0.013 (2)0.0104 (19)0.0034 (19)
C130.036 (2)0.056 (2)0.043 (2)0.0057 (19)0.0013 (16)0.0003 (18)
C140.038 (2)0.0355 (16)0.0332 (17)0.0004 (17)0.0067 (16)0.0051 (15)
C150.043 (2)0.0442 (17)0.0388 (19)0.0005 (19)0.0019 (19)0.0012 (15)
C160.064 (3)0.043 (2)0.0360 (19)0.007 (2)0.0056 (18)0.0067 (15)
C170.062 (3)0.036 (2)0.049 (2)0.0012 (18)0.018 (2)0.0025 (16)
C180.050 (2)0.0447 (18)0.048 (2)0.016 (2)0.0068 (18)0.0082 (18)
C190.048 (2)0.044 (2)0.0400 (19)0.0024 (19)0.0047 (19)0.0006 (16)
Geometric parameters (Å, º) top
O1—P21.590 (2)C10—C111.379 (5)
O1—C61.442 (4)C10—H290.916
P2—C31.808 (3)C11—C121.359 (5)
P2—O71.464 (2)C11—H280.937
P2—H201.406C12—C131.386 (5)
C3—N41.469 (4)C12—H270.936
C3—C81.513 (4)C13—H260.921
C3—H210.981C14—C151.391 (4)
N4—C51.463 (4)C14—C191.380 (5)
N4—H221.052C15—C161.375 (4)
C5—C61.529 (4)C15—H310.930
C5—C141.513 (4)C16—C171.385 (5)
C5—H230.981C16—H320.944
C6—H240.999C17—C181.369 (5)
C6—H250.978C17—H330.939
C8—C91.372 (5)C18—C191.396 (5)
C8—C131.384 (5)C18—H340.931
C9—C101.382 (5)C19—H350.938
C9—H300.930
P2—O1—C6116.95 (18)C8—C9—H30119.9
O1—P2—C3103.67 (13)C10—C9—H30119.2
O1—P2—O7113.04 (13)C9—C10—C11119.8 (4)
C3—P2—O7115.96 (16)C9—C10—H29119.8
O1—P2—H20105.6C11—C10—H29120.3
C3—P2—H20106.0C10—C11—C12119.8 (4)
O7—P2—H20111.7C10—C11—H28119.3
P2—C3—N4107.3 (2)C12—C11—H28120.8
P2—C3—C8109.4 (2)C11—C12—C13120.3 (4)
N4—C3—C8112.8 (3)C11—C12—H27121.0
P2—C3—H21108.4C13—C12—H27118.7
N4—C3—H21109.2C12—C13—C8120.4 (4)
C8—C3—H21109.7C12—C13—H26119.5
C3—N4—C5112.8 (2)C8—C13—H26120.1
C3—N4—H22109.2C5—C14—C15120.7 (3)
C5—N4—H22106.3C5—C14—C19120.3 (3)
N4—C5—C6108.5 (2)C15—C14—C19119.0 (3)
N4—C5—C14110.6 (2)C14—C15—C16120.6 (4)
C6—C5—C14108.8 (3)C14—C15—H31118.2
N4—C5—H23110.0C16—C15—H31121.2
C6—C5—H23111.0C15—C16—C17120.0 (3)
C14—C5—H23107.9C15—C16—H32120.5
C5—C6—O1111.8 (3)C17—C16—H32119.5
C5—C6—H24107.0C16—C17—C18120.1 (3)
O1—C6—H24109.0C16—C17—H33121.4
C5—C6—H25109.4C18—C17—H33118.6
O1—C6—H25108.5C17—C18—C19120.1 (3)
H24—C6—H25111.2C17—C18—H34120.6
C3—C8—C9122.1 (3)C19—C18—H34119.3
C3—C8—C13119.2 (3)C18—C19—C14120.2 (3)
C9—C8—C13118.7 (3)C18—C19—H35120.0
C8—C9—C10120.9 (4)C14—C19—H35119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H22···O7i1.051.962.916 (2)149
Symmetry code: (i) x+1, y+1/2, z+3/2.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC20H26NO2PC20H26NO2PC22H27FNO3PC22H27FNO3P
Mr343.39343.39403.43403.43
Crystal system, space groupOrthorhombic, PbcaTriclinic, P1Monoclinic, P21/cMonoclinic, P21/c
Temperature (K)120120293293
a, b, c (Å)10.5381 (8), 15.7519 (14), 22.626 (2)6.7231 (5), 11.9766 (6), 23.6865 (16)6.411 (2), 16.206 (4), 21.242 (5)19.252 (2), 6.584 (1), 17.295 (2)
α, β, γ (°)90, 90, 9097.644 (3), 93.038 (2), 98.742 (2)90, 99.51 (2), 9090, 101.73 (2), 90
V3)3755.8 (6)1863.1 (2)2176.7 (10)2146.5 (5)
Z8444
Radiation typeSynchrotron, λ = 0.50606 ÅSynchrotron, λ = 0.50606 ÅMo KαMo Kα
µ (mm1)0.070.070.160.16
Crystal size (mm)0.50 × 0.05 × 0.050.40 × 0.05 × 0.050.40 × 0.05 × 0.020.20 × 0.06 × 0.04
Data collection
DiffractometerBruker SMART
diffractometer
Bruker SMART
diffractometer
Siemens P3
diffractometer
Siemens P3
diffractometer
Absorption correctionMulti-scan
SADABS (Siemens, 1996)
Multi-scan
SADABS (Siemens, 1996)
ψ scanψ scan
Tmin, Tmax0.89, 1.000.91, 1.000.86, 0.960.85, 0.94
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
22025, 6228, 4671 32894, 11718, 7201 2740, 2355, 558 3395, 2972, 660
Rint0.0720.0730.0570.041
θmax (°)20.820.921.123.1
(sin θ/λ)max1)0.7020.7040.5050.551
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.052, 0.99 0.050, 0.053, 1.06 0.128, 0.144, 1.10 0.113, 0.126, 1.18
No. of reflections46717201558660
No. of parameters218434113113
No. of restraints001111
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.670.48, 0.580.47, 0.560.71, 0.63
Absolute structure????
Absolute structure parameter????


(V)(VI)(VII)(VIII)
Crystal data
Chemical formulaC22H28NO3PC25H28NO2PC22H22NO3PC21H20NO2P
Mr385.44405.48379.40349.37
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21Orthorhombic, P212121
Temperature (K)175175175175
a, b, c (Å)12.109 (3), 14.047 (3), 13.206 (6)10.284 (2), 21.262 (4), 12.768 (2)10.0104 (3), 8.1056 (1), 12.5372 (3)5.6212 (6), 25.714 (2), 13.561 (2)
α, β, γ (°)90, 111.48 (3), 9090, 119.04 (2), 9090, 109.717 (5), 9090, 90, 90
V3)2090.3 (12)2440.9 (9)957.63 (5)1960.2 (4)
Z4424
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.150.130.170.15
Crystal size (mm)0.50 × 0.06 × 0.040.37 × 0.07 × 0.040.32 × 0.30 × 0.200.33 × 0.05 × 0.05
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Enraf-Nonius CAD4
diffractometer
Oxford Diffraction XCALIBUR
diffractometer
Oxford Diffraction XCALIBUR
diffractometer
Absorption correctionψ scanψ scanMulti-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Multi-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Tmin, Tmax0.84, 0.920.81, 0.910.952, 0.9670.91, 0.99
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
2836, 2561, 1019 2619, 2576, 1037 12688, 5435, 3438 33616, 6347, 496
Rint0.0180.040.0280.203
θmax (°)22.022.032.232.5
(sin θ/λ)max1)0.5260.5260.7500.755
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.065, 1.14 0.085, 0.091, 1.16 0.048, 0.046, 1.11 0.131, 0.119, 1.00
No. of reflections101910373438496
No. of parameters24413224587
No. of restraints01916
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.300.46, 0.520.23, 0.311.86, 0.51
Absolute structure??Flack (1983), 2104 Friedel-pairsFlack (1983), 2610 Friedel-pairs
Absolute structure parameter??0.18 (12)0.0 (15)


(IX)
Crystal data
Chemical formulaC15H16NO2P
Mr273.27
Crystal system, space groupOrthorhombic, P212121
Temperature (K)175
a, b, c (Å)5.3914 (2), 11.7559 (4), 21.6032 (8)
α, β, γ (°)90, 90, 90
V3)1369.23 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerOxford Diffraction XCALIBUR
diffractometer
Absorption correctionMulti-scan
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Tmin, Tmax0.940, 0.961
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
26882, 4506, 1197
Rint0.057
θmax (°)32.5
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.029, 1.11
No. of reflections1197
No. of parameters173
No. of restraints0
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.18
Absolute structureFlack (1983), 1866 Friedel-pairs
Absolute structure parameter0.10 (16)

Computer programs: SMART (Siemens, 1993), P3/PC. (Siemens,1993), Enraf-Nonius (1989), CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34), CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17), SAINT (Siemens ,1995), CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34), CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17), XCAD4 (Harms, K. \& Wocadlo, S., 1995), SIR92 (Altomare et al., 1994), SIR2002 (Burla et al., 2003), Superflip (Palatinus, 2006), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Selected geometric parameters (Å, º) for (I) top
O1—P21.6030 (7)C11—C121.5306 (8)
O1—C51.4520 (8)C13—C141.3920 (11)
P2—N31.6632 (7)C13—C181.3940 (9)
P2—O61.4772 (7)C14—C151.3944 (11)
P2—C111.7984 (8)C15—C161.3863 (9)
N3—C41.4739 (9)C16—C171.3871 (11)
N3—C71.4969 (12)C17—C181.3918 (11)
C4—C51.5602 (10)C19—C201.3912 (12)
C4—C131.5147 (11)C19—C241.3919 (10)
C5—C191.5012 (11)C20—C211.3926 (11)
C7—C81.5290 (10)C21—C221.3870 (10)
C7—C91.5347 (12)C22—C231.3901 (14)
C7—C101.5291 (9)C23—C241.3968 (11)
P2—O1—C5109.47 (5)C8—C7—C10108.25 (6)
O1—P2—N395.90 (4)C9—C7—C10110.28 (6)
O1—P2—O6115.91 (4)P2—C11—C12111.48 (5)
N3—P2—O6117.12 (4)C4—C13—C14122.68 (6)
O1—P2—C11102.86 (4)C4—C13—C18118.50 (7)
N3—P2—C11112.43 (4)C14—C13—C18118.77 (7)
O6—P2—C11111.02 (4)C13—C14—C15120.34 (6)
P2—N3—C4111.71 (5)C14—C15—C16120.57 (7)
P2—N3—C7122.95 (5)C15—C16—C17119.34 (7)
C4—N3—C7117.43 (6)C16—C17—C18120.24 (6)
N3—C4—C5104.46 (5)C13—C18—C17120.72 (7)
N3—C4—C13113.89 (6)C5—C19—C20121.14 (6)
C5—C4—C13113.69 (6)C5—C19—C24118.77 (8)
C4—C5—O1105.39 (5)C20—C19—C24119.97 (7)
C4—C5—C19114.97 (6)C19—C20—C21120.07 (7)
O1—C5—C19110.09 (6)C20—C21—C22120.14 (8)
N3—C7—C8109.40 (6)C21—C22—C23119.88 (7)
N3—C7—C9109.86 (7)C22—C23—C24120.23 (7)
C8—C7—C9110.14 (6)C23—C24—C19119.70 (8)
N3—C7—C10108.88 (6)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C4—H25···O6i0.96002.40003.244 (2)146.00
Symmetry code: (i) x1/2, y, z+1/2.
Selected geometric parameters (Å, º) for (II) top
P2—O11.605 (2)P26—C351.807 (3)
P2—O61.472 (2)O1—C51.451 (3)
P2—N31.645 (2)O25—C291.450 (3)
P2—C111.805 (3)N3—C41.475 (3)
P26—O301.470 (2)N3—C71.486 (3)
P26—N271.654 (2)N27—C311.491 (3)
P26—O251.605 (2)N27—C281.483 (3)
O1—P2—O6113.21 (13)P26—N27—C31125.57 (17)
O1—P2—N396.02 (11)P26—N27—C28111.09 (15)
O1—P2—C11105.03 (14)N3—C4—C13114.38 (19)
O6—P2—N3119.21 (12)N3—C4—C5102.21 (18)
O6—P2—C11111.04 (13)O1—C5—C4104.65 (19)
N3—P2—C11110.67 (12)O1—C5—C19111.3 (2)
N27—P26—C35111.18 (12)N3—C7—C10109.4 (2)
O25—P26—N2796.46 (11)N3—C7—C8110.1 (2)
O25—P26—C35103.73 (11)N3—C7—C9109.3 (2)
O25—P26—O30113.94 (12)P2—C11—C12112.6 (2)
O30—P26—C35110.75 (13)N27—C28—C29101.51 (17)
O30—P26—N27119.06 (12)N27—C28—C37116.56 (19)
P2—O1—C5109.54 (16)O25—C29—C28104.99 (18)
P26—O25—C29109.59 (15)O25—C29—C43111.17 (19)
P2—N3—C7128.14 (18)N27—C31—C32109.0 (2)
P2—N3—C4111.97 (16)N27—C31—C33108.7 (2)
C4—N3—C7119.54 (19)N27—C31—C34111.2 (2)
C28—N27—C31121.12 (19)P26—C35—C36110.86 (19)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
C4—H50···O6i0.94002.28003.196 (3)165.00
C28—H75···O30ii0.93002.27003.179 (3)165.00
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
Selected geometric parameters (Å, º) for (III) top
O1—P21.60 (2)C13—C141.395 (9)
O1—C51.47 (3)C13—C181.393 (10)
P2—N31.58 (2)C14—C151.393 (10)
P2—O61.51 (2)C15—C161.389 (10)
P2—C71.81 (3)C16—C171.400 (10)
N3—C41.45 (3)C17—C181.45 (4)
N3—C251.60 (4)C19—C201.395 (10)
C4—C51.53 (4)C19—C241.396 (10)
C4—C191.50 (3)C20—C211.398 (10)
C5—C131.49 (3)C21—C221.390 (10)
C7—F81.46 (3)C22—C231.395 (10)
C7—C91.53 (4)C23—C241.400 (10)
C7—C101.58 (4)C25—C261.66 (6)
C10—O111.26 (3)C25—C271.31 (6)
C10—C121.41 (4)C25—C281.42 (5)
P2—O1—C5111.4 (17)O11—C10—C12126 (3)
O1—P2—N395.9 (13)C5—C13—C14117 (2)
O1—P2—O6116.3 (12)C5—C13—C18124 (3)
N3—P2—O6118.2 (13)C14—C13—C18119 (3)
O1—P2—C799.8 (14)C13—C14—C15118 (3)
N3—P2—C7113.4 (13)C14—C15—C16123 (3)
O6—P2—C7111.0 (14)C15—C16—C17122 (3)
P2—N3—C4116 (2)C16—C17—C18114 (3)
P2—N3—C25126 (2)C17—C18—C13125 (3)
C4—N3—C25118 (3)C4—C19—C20123 (3)
N3—C4—C5103 (2)C4—C19—C24121 (2)
N3—C4—C19116 (2)C20—C19—C24116 (3)
C5—C4—C19111 (2)C19—C20—C21124 (3)
C4—C5—O1106 (2)C20—C21—C22115 (3)
C4—C5—C13120 (3)C21—C22—C23126 (3)
O1—C5—C13115 (2)C22—C23—C24114 (3)
P2—C7—F8106 (2)C23—C24—C19125 (3)
P2—C7—C9113 (2)N3—C25—C26101 (3)
F8—C7—C9106 (3)N3—C25—C27116 (5)
P2—C7—C10116 (2)C26—C25—C27108 (5)
F8—C7—C10108 (2)N3—C25—C28111 (4)
C9—C7—C10107 (3)C26—C25—C2892 (4)
C7—C10—O11114 (3)C27—C25—C28123 (5)
C7—C10—C12120 (3)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
C4—H30···O6i0.98002.49003.30 (4)139.00
Symmetry code: (i) x+1, y, z.
Selected geometric parameters (Å, º) for (IV) top
O1—P21.602 (14)C13—C141.391 (9)
O1—C51.45 (2)C13—C181.387 (9)
P2—N31.613 (17)C14—C151.394 (9)
P2—O61.483 (16)C15—C161.389 (9)
P2—C71.896 (19)C16—C171.390 (9)
N3—C41.45 (2)C17—C181.43 (3)
N3—C251.54 (2)C19—C201.388 (9)
C4—C51.56 (3)C19—C241.389 (9)
C4—C191.45 (3)C20—C211.390 (9)
C5—C131.50 (3)C21—C221.390 (9)
C7—F81.44 (2)C22—C231.394 (9)
C7—C91.51 (3)C23—C241.397 (9)
C7—C101.53 (3)C25—C261.50 (3)
C10—O111.19 (3)C25—C271.53 (3)
C10—C121.46 (3)C25—C281.52 (3)
P2—O1—C5109.6 (13)O11—C10—C12130 (3)
O1—P2—N395.3 (8)C5—C13—C14122.9 (16)
O1—P2—O6114.9 (9)C5—C13—C18117.7 (18)
N3—P2—O6123.7 (9)C14—C13—C18119 (2)
O1—P2—C7101.9 (8)C13—C14—C15123 (2)
N3—P2—C7114.2 (9)C14—C15—C16117 (2)
O6—P2—C7104.9 (10)C15—C16—C17122 (2)
P2—N3—C4115.9 (13)C16—C17—C18120 (2)
P2—N3—C25125.1 (14)C17—C18—C13119 (2)
C4—N3—C25119.0 (17)C4—C19—C20117.6 (18)
N3—C4—C5100.1 (15)C4—C19—C24127.6 (19)
N3—C4—C19118.1 (17)C20—C19—C24114 (2)
C5—C4—C19108.7 (17)C19—C20—C21125 (2)
C4—C5—O1106.3 (16)C20—C21—C22116 (3)
C4—C5—C13118.3 (16)C21—C22—C23124 (2)
O1—C5—C13109.9 (17)C22—C23—C24115 (2)
P2—C7—F8102.7 (13)C23—C24—C19125 (2)
P2—C7—C9115.5 (14)N3—C25—C26109.1 (18)
F8—C7—C9107.9 (17)N3—C25—C27109.9 (19)
P2—C7—C10108.4 (14)C26—C25—C27108 (2)
F8—C7—C10106.2 (17)N3—C25—C28107.5 (17)
C9—C7—C10115.0 (18)C26—C25—C28109 (2)
C7—C10—O11117 (2)C27—C25—C28113.6 (19)
C7—C10—C12113 (2)
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
C4—H30···O6i0.98002.22003.18 (2)163.00
C28—H48···O11ii0.962.71003.57 (3)150.83
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2.
Selected geometric parameters (Å, º) for (V) top
O1—P21.587 (6)C13—O141.218 (10)
O1—C51.437 (9)C13—C151.479 (12)
P2—N31.652 (7)C16—C171.389 (11)
P2—O61.459 (6)C16—C211.409 (12)
P2—C111.836 (9)C17—C181.374 (13)
N3—C41.484 (10)C18—C191.373 (13)
N3—C71.502 (11)C19—C201.368 (13)
C4—C51.554 (11)C20—C211.363 (12)
C4—C161.497 (11)C22—C231.365 (11)
C5—C221.515 (11)C22—C271.377 (12)
C7—C81.490 (16)C23—C241.386 (12)
C7—C91.448 (15)C24—C251.374 (13)
C7—C101.515 (14)C25—C261.357 (13)
C11—C121.522 (11)C26—C271.398 (12)
C11—C131.540 (13)
P2—O1—C5113.1 (5)P2—C11—C12113.7 (6)
O1—P2—N396.1 (3)P2—C11—C13106.9 (6)
O1—P2—O6113.9 (4)C12—C11—C13113.4 (8)
N3—P2—O6119.0 (4)C11—C13—O14118.8 (9)
O1—P2—C11105.1 (4)C11—C13—C15118.3 (9)
N3—P2—C11111.6 (4)O14—C13—C15122.8 (10)
O6—P2—C11109.7 (4)C4—C16—C17119.9 (8)
P2—N3—C4110.3 (5)C4—C16—C21122.8 (8)
P2—N3—C7125.8 (5)C17—C16—C21117.2 (9)
C4—N3—C7121.8 (6)C16—C17—C18121.8 (9)
N3—C4—C5102.3 (6)C17—C18—C19120.2 (10)
N3—C4—C16117.1 (8)C18—C19—C20118.5 (10)
C5—C4—C16113.2 (7)C19—C20—C21122.7 (11)
C4—C5—O1104.7 (6)C16—C21—C20119.5 (9)
C4—C5—C22113.8 (7)C5—C22—C23119.2 (8)
O1—C5—C22111.0 (6)C5—C22—C27121.3 (8)
N3—C7—C8110.1 (9)C23—C22—C27119.5 (9)
N3—C7—C9109.1 (8)C22—C23—C24119.8 (9)
C8—C7—C9113.5 (12)C23—C24—C25121.0 (10)
N3—C7—C10109.5 (7)C24—C25—C26119.4 (9)
C8—C7—C10105.2 (11)C25—C26—C27120.0 (9)
C9—C7—C10109.4 (12)C26—C27—C22120.3 (9)
Hydrogen-bond geometry (Å, º) for (V) top
D—H···AD—HH···AD···AD—H···A
C23—H51···O6i1.04002.21003.240 (12)170.00
C10—H34···O14ii1.01002.58003.552 (16)161.00
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2.
Selected geometric parameters (Å, º) for (VI) top
O1—P21.655 (8)C13—C141.405 (9)
O1—C51.447 (13)C14—C151.413 (9)
P2—N31.710 (10)C15—C161.434 (9)
P2—O61.665 (9)C16—C171.406 (9)
P2—C111.837 (11)C18—C191.409 (9)
N3—C41.585 (14)C18—C231.400 (9)
N3—C71.542 (14)C19—C201.409 (9)
C4—C51.599 (15)C20—C211.401 (9)
C4—C241.640 (9)C21—C221.413 (9)
C5—C181.604 (15)C22—C231.413 (9)
C7—C81.621 (15)C24—C251.420 (9)
C7—C91.597 (17)C24—C291.436 (9)
C7—C101.544 (15)C25—C261.437 (9)
C11—C121.594 (14)C26—C271.423 (9)
C12—C131.437 (9)C27—C281.404 (9)
C12—C171.420 (9)C28—C291.440 (9)
P2—O1—C5110.5 (6)C11—C12—C17111.7 (8)
O1—P2—N391.6 (4)C13—C12—C17124.8 (10)
O1—P2—O6120.0 (5)C12—C13—C14123.1 (10)
N3—P2—O6120.2 (5)C13—C14—C15112.0 (11)
O1—P2—C1197.3 (5)C14—C15—C16124.7 (12)
N3—P2—C11110.6 (5)C15—C16—C17123.6 (12)
O6—P2—C11113.3 (5)C12—C17—C16111.4 (10)
P2—N3—C4113.9 (7)C5—C18—C19128.3 (9)
P2—N3—C7117.2 (7)C5—C18—C23116.0 (9)
C4—N3—C7120.3 (8)C19—C18—C23115.5 (11)
N3—C4—C597.8 (7)C18—C19—C20127.4 (12)
N3—C4—C24121.3 (8)C19—C20—C21116.2 (12)
C5—C4—C24118.8 (9)C20—C21—C22117.6 (12)
C4—C5—O1104.6 (8)C21—C22—C23124.9 (12)
C4—C5—C18109.9 (9)C22—C23—C18118.3 (11)
O1—C5—C18110.5 (9)C4—C24—C25127.0 (9)
N3—C7—C8101.7 (9)C4—C24—C29126.9 (9)
N3—C7—C9115.3 (9)C25—C24—C29106.0 (9)
C8—C7—C9116.4 (9)C24—C25—C26126.5 (11)
N3—C7—C10110.3 (9)C25—C26—C27125.3 (12)
C8—C7—C10108.5 (9)C26—C27—C28110.4 (12)
C9—C7—C10104.6 (9)C27—C28—C29122.6 (13)
P2—C11—C12109.8 (7)C28—C29—C24129.1 (11)
C11—C12—C13123.4 (9)
Hydrogen-bond geometry (Å, º) for (VI) top
D—H···AD—HH···AD···AD—H···A
C11—H50···O6i0.97002.51003.463 (14)169.00
C13—H56···O1i0.93002.64003.432 (13)143.00
Symmetry code: (i) x+1, y, z+1.
Selected geometric parameters (Å, º) for (VII) top
O1—P21.600 (2)C11—O141.365 (3)
O1—C61.440 (4)C12—C131.390 (4)
P2—C31.818 (3)O14—C151.438 (4)
P2—O71.475 (2)C16—C171.393 (4)
P2—C81.799 (3)C16—C211.392 (4)
C3—N41.476 (3)C17—C181.396 (5)
C3—C221.512 (4)C18—C191.372 (6)
N4—C51.478 (4)C19—C201.394 (5)
C5—C61.524 (4)C20—C211.383 (5)
C5—C161.509 (4)C22—C231.384 (4)
C8—C91.393 (4)C22—C271.397 (4)
C8—C131.397 (4)C23—C241.388 (4)
C9—C101.387 (4)C24—C251.387 (4)
C10—C111.390 (4)C25—C261.382 (5)
C11—C121.382 (4)C26—C271.381 (4)
P2—O1—C6120.91 (19)C10—C11—O14114.6 (3)
O1—P2—C3102.82 (12)C12—C11—O14124.7 (3)
O1—P2—O7110.31 (13)C11—C12—C13119.3 (3)
C3—P2—O7114.03 (13)C8—C13—C12121.1 (3)
O1—P2—C8107.80 (12)C11—O14—C15117.0 (3)
C3—P2—C8109.70 (12)C5—C16—C17120.7 (3)
O7—P2—C8111.67 (13)C5—C16—C21120.6 (3)
P2—C3—N4108.90 (17)C17—C16—C21118.7 (3)
P2—C3—C22110.02 (18)C16—C17—C18120.0 (3)
N4—C3—C22112.7 (2)C17—C18—C19120.7 (3)
C3—N4—C5111.8 (2)C18—C19—C20120.0 (3)
N4—C5—C6109.2 (2)C19—C20—C21119.4 (3)
N4—C5—C16109.6 (2)C16—C21—C20121.4 (3)
C6—C5—C16109.0 (2)C3—C22—C23122.4 (2)
C5—C6—O1113.0 (2)C3—C22—C27119.1 (3)
P2—C8—C9116.75 (19)C23—C22—C27118.4 (3)
P2—C8—C13124.7 (2)C22—C23—C24120.8 (3)
C9—C8—C13118.5 (2)C23—C24—C25120.0 (3)
C8—C9—C10120.9 (2)C24—C25—C26119.8 (3)
C9—C10—C11119.5 (3)C25—C26—C27119.9 (3)
C10—C11—C12120.7 (2)C22—C27—C26121.1 (3)
Hydrogen-bond geometry (Å, º) for (VII) top
D—H···AD—HH···AD···AD—H···A
N4—H31···O7i0.93002.54003.089 (3)118.00
C3—H32···O7i0.99002.57003.153 (4)118.00
C21—H44···O14ii0.93002.60003.286 (4)131.00
Symmetry codes: (i) x, y1/2, z+1; (ii) x+1, y1/2, z+2.
Selected geometric parameters (Å, º) for (VIII) top
O1—P21.56 (3)C11—C121.48 (5)
O1—C61.45 (4)C12—C131.36 (4)
P2—C31.87 (3)C14—C151.38 (4)
P2—O71.46 (2)C14—C191.30 (4)
P2—C201.76 (3)C15—C161.44 (4)
C3—N41.66 (5)C16—C171.36 (4)
C3—C141.45 (5)C17—C181.31 (4)
N4—C51.46 (4)C18—C191.29 (4)
C5—C61.53 (4)C20—C211.394 (10)
C5—C81.54 (5)C20—C251.395 (10)
C8—C91.41 (5)C21—C221.389 (10)
C8—C131.40 (4)C22—C231.392 (10)
C9—C101.38 (4)C23—C241.396 (10)
C10—C111.45 (5)C24—C251.392 (10)
P2—O1—C6119 (2)C10—C11—C12113 (3)
O1—P2—C3103.7 (15)C11—C12—C13119 (4)
O1—P2—O7117.5 (14)C8—C13—C12127 (4)
C3—P2—O7114.1 (14)C3—C14—C15118 (4)
O1—P2—C20104.2 (15)C3—C14—C19119 (3)
C3—P2—C20104.1 (17)C15—C14—C19123 (3)
O7—P2—C20111.9 (14)C14—C15—C16116 (3)
P2—C3—N4102 (2)C15—C16—C17115 (3)
P2—C3—C14115 (3)C16—C17—C18125 (4)
N4—C3—C14112 (3)C17—C18—C19119 (4)
C3—N4—C5110 (3)C14—C19—C18122 (4)
N4—C5—C6119 (3)P2—C20—C21127 (3)
N4—C5—C8112 (3)P2—C20—C25118 (2)
C6—C5—C8104 (3)C21—C20—C25115 (3)
C5—C6—O1106 (3)C20—C21—C22123 (3)
C5—C8—C9121 (3)C21—C22—C23119 (3)
C5—C8—C13121 (4)C22—C23—C24118 (3)
C9—C8—C13116 (3)C23—C24—C25120 (3)
C8—C9—C10119 (4)C20—C25—C24123 (3)
C9—C10—C11126 (4)
Hydrogen-bond geometry (Å, º) for (VIII) top
D—H···AD—HH···AD···AD—H···A
C3—H30···O7i0.982.253.23 (5)177
Symmetry code: (i) x1, y, z.
Selected geometric parameters (Å, º) for (IX) top
O1—P21.590 (2)C9—C101.382 (5)
O1—C61.442 (4)C10—C111.379 (5)
P2—C31.808 (3)C11—C121.359 (5)
P2—O71.464 (2)C12—C131.386 (5)
C3—N41.469 (4)C14—C151.391 (4)
C3—C81.513 (4)C14—C191.380 (5)
N4—C51.463 (4)C15—C161.375 (4)
C5—C61.529 (4)C16—C171.385 (5)
C5—C141.513 (4)C17—C181.369 (5)
C8—C91.372 (5)C18—C191.396 (5)
C8—C131.384 (5)
P2—O1—C6116.95 (18)C9—C8—C13118.7 (3)
O1—P2—C3103.67 (13)C8—C9—C10120.9 (4)
O1—P2—O7113.04 (13)C9—C10—C11119.8 (4)
C3—P2—O7115.96 (16)C10—C11—C12119.8 (4)
P2—C3—N4107.3 (2)C11—C12—C13120.3 (4)
P2—C3—C8109.4 (2)C12—C13—C8120.4 (4)
N4—C3—C8112.8 (3)C5—C14—C15120.7 (3)
C3—N4—C5112.8 (2)C5—C14—C19120.3 (3)
N4—C5—C6108.5 (2)C15—C14—C19119.0 (3)
N4—C5—C14110.6 (2)C14—C15—C16120.6 (4)
C6—C5—C14108.8 (3)C15—C16—C17120.0 (3)
C5—C6—O1111.8 (3)C16—C17—C18120.1 (3)
C3—C8—C9122.1 (3)C17—C18—C19120.1 (3)
C3—C8—C13119.2 (3)C18—C19—C14120.2 (3)
Hydrogen-bond geometry (Å, º) for (IX) top
D—H···AD—HH···AD···AD—H···A
N4—H22···O7i1.051.962.916 (2)149
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

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