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The title compound (2,2,2-tris­(cyclo­hexyl­oxy)­phen­anthro[9,10-d][1,3,2]­dioxa­phospho­le), C32H41O5P, displays trigonal-bipyramidal geometry at the central P atom. The P-O bond lengths (Å) are: in the five-membered ring 1.652 (2) Å equatorial and 1.744 (2) Å axial, and to the cyclo­hexyl­oxy groups 1.581 (2) and 1.589 (2) Å equatorial, and 1.624 (2) Å axial.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002398/na6138sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002398/na6138Isup2.hkl
Contains datablock I

CCDC reference: 182615

Key indicators

  • Single-crystal X-ray study
  • T = 143 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.119
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

We are interested in the correlation between structure and reactivity (see e.g. Amos et al., 1992). The structure of the title compound, (I), the adduct of tricyclohexyl phosphite and phenanthraquinone, was determined as part of a combined crystallographic and theoretical investigation of pKa values of pentaoxyphosphoranes (Davies et al., 2002).

The structure is shown in Fig. 1; a minor (11%) disorder component of the ring C11–16 is not shown. Of the three cyclohexyloxy groups, one is axial (O5, C31 etc.) and the other two are equatorial. This is reflected in the normal bond-length pattern for trigonal–bipyramidal geometry (axial bonds longer than equatorial), as was also observed in pentakis(cyclohexyloxy)phosphorane (Davies et al., 2001; average values in four independent molecules 1.662 Å for axial and 1.606 Å for equatorial P—O bonds). The triisopropyloxy analogue of the title compound was subjected to structure analysis in 1967. There were two modifications, of which the more precisely determined modification (Spratley et al., 1967) displayed a similar P—O bond-length pattern to the title compound: ring apical 1.751 (7) Å, equatorial 1.633 (7) Å; iPr apical 1.638 (6) Å, and equatorial 1.588 (7) and 1.574 (7) Å.

Experimental top

Compound I was prepared by adding triisopropyl phosphite to one equivalent of phenanthraquinone at room temperature, according to the method of Hamilton et al. (1967).

Refinement top

H atoms were positioned geometrically and refined using a riding model. Cyclohexyl ring C11–16 is disordered over two positions with a relative occupancy of ca 9:1. The minor component was refined isotropically with an appropriate system of restraints.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecule of the title compound in the crystal. The minor disorder component of the ring C11–C16 has been omitted. Ellipsoids represent 50% probability levels.
(I) top
Crystal data top
C32H41O5PF(000) = 1152
Mr = 536.62Dx = 1.251 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.665 (2) ÅCell parameters from 50 reflections
b = 15.394 (3) Åθ = 10–11.5°
c = 19.200 (4) ŵ = 0.14 mm1
β = 93.92 (2)°T = 143 K
V = 2850.1 (10) Å3Prism, colourless
Z = 40.65 × 0.30 × 0.30 mm
Data collection top
Stoe STADI-4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.2°
Graphite monochromatorh = 110
ω/θ scansk = 181
5588 measured reflectionsl = 2222
5037 independent reflections3 standard reflections every 60 min
3708 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0447P)2 + 1.4014P]
where P = (Fo2 + 2Fc2)/3
5037 reflections(Δ/σ)max < 0.001
368 parametersΔρmax = 0.21 e Å3
18 restraintsΔρmin = 0.31 e Å3
Crystal data top
C32H41O5PV = 2850.1 (10) Å3
Mr = 536.62Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.665 (2) ŵ = 0.14 mm1
b = 15.394 (3) ÅT = 143 K
c = 19.200 (4) Å0.65 × 0.30 × 0.30 mm
β = 93.92 (2)°
Data collection top
Stoe STADI-4
diffractometer
Rint = 0.024
5588 measured reflections3 standard reflections every 60 min
5037 independent reflections intensity decay: none
3708 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.04818 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.04Δρmax = 0.21 e Å3
5037 reflectionsΔρmin = 0.31 e Å3
368 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

The cyclohexyl ring C11–16 is disordered over two positions with relative occupancy ca 9:1. The minor component was refined isotropically with an appropriate system of restraints.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P0.22024 (6)0.74534 (4)0.55113 (3)0.02318 (16)
O10.29440 (15)0.65883 (10)0.50841 (8)0.0240 (4)
O20.06583 (16)0.70951 (10)0.52199 (8)0.0257 (4)
O30.28511 (17)0.81751 (10)0.50470 (8)0.0313 (4)
O40.31223 (16)0.71164 (10)0.61744 (8)0.0267 (4)
O50.14331 (16)0.81665 (10)0.59740 (8)0.0270 (4)
C10.1855 (2)0.63593 (16)0.44820 (12)0.0288 (6)
H10.19890.68570.47620.035*
C20.2968 (3)0.59791 (17)0.41217 (13)0.0333 (6)
H20.38690.62200.41440.040*
C30.2776 (3)0.52407 (18)0.37239 (13)0.0359 (6)
H30.35530.49780.34780.043*
C40.1483 (3)0.48844 (16)0.36806 (12)0.0306 (6)
H40.13800.43760.34080.037*
C4A0.0308 (2)0.52600 (15)0.40342 (11)0.0240 (5)
C4B0.1088 (2)0.49048 (15)0.39978 (11)0.0243 (5)
C50.1354 (3)0.41236 (16)0.36529 (12)0.0312 (6)
H50.06040.38180.34200.037*
C60.2667 (3)0.37925 (17)0.36439 (13)0.0362 (6)
H60.28110.32610.34090.043*
C70.3794 (3)0.42243 (16)0.39744 (12)0.0315 (6)
H70.47000.39860.39700.038*
C80.3586 (2)0.49965 (15)0.43068 (12)0.0260 (5)
H80.43560.53010.45220.031*
C8A0.2248 (2)0.53416 (15)0.43322 (11)0.0230 (5)
C90.1970 (2)0.61038 (14)0.47159 (11)0.0219 (5)
C100.0683 (2)0.63887 (14)0.47787 (11)0.0225 (5)
C10A0.0516 (2)0.60151 (15)0.44393 (11)0.0235 (5)
C110.3657 (4)0.8104 (2)0.4430 (2)0.0326 (9)0.892 (4)
H110.35320.75150.42150.039*0.892 (4)
C120.5167 (3)0.8257 (3)0.46510 (17)0.0506 (10)0.892 (4)
H12A0.55190.77720.49520.061*0.892 (4)
H12B0.52600.88000.49270.061*0.892 (4)
C130.6031 (4)0.8327 (3)0.4016 (2)0.0684 (13)0.892 (4)
H13A0.69990.84750.41740.082*0.892 (4)
H13B0.60390.77570.37770.082*0.892 (4)
C140.5463 (6)0.9011 (4)0.3506 (2)0.0570 (16)0.892 (4)
H14A0.55550.95920.37260.068*0.892 (4)
H14B0.60090.90100.30880.068*0.892 (4)
C150.3956 (4)0.8838 (3)0.32889 (17)0.0539 (10)0.892 (4)
H15A0.38730.82830.30290.065*0.892 (4)
H15B0.35930.93070.29750.065*0.892 (4)
C160.3103 (3)0.8792 (2)0.39259 (15)0.0416 (9)0.892 (4)
H16A0.31270.93630.41630.050*0.892 (4)
H16B0.21260.86600.37750.050*0.892 (4)
C11'0.397 (3)0.811 (2)0.4615 (12)0.024 (9)*0.108 (4)
H11'0.45730.76010.47470.028*0.108 (4)
C12'0.476 (2)0.8951 (15)0.4707 (11)0.037 (6)*0.108 (4)
H12C0.52400.89710.51790.044*0.108 (4)
H12D0.41110.94470.46610.044*0.108 (4)
C13'0.582 (3)0.903 (3)0.4162 (16)0.086 (12)*0.108 (4)
H13C0.62650.96060.42010.103*0.108 (4)
H13D0.65560.85850.42590.103*0.108 (4)
C14'0.520 (6)0.890 (3)0.3423 (16)0.072 (18)*0.108 (4)
H14C0.59480.89190.30950.086*0.108 (4)
H14D0.45550.93890.33010.086*0.108 (4)
C15'0.443 (3)0.8049 (18)0.3343 (12)0.053 (8)*0.108 (4)
H15C0.50810.75580.34200.064*0.108 (4)
H15D0.39770.79990.28650.064*0.108 (4)
C16'0.332 (2)0.8021 (17)0.3884 (12)0.043 (7)*0.108 (4)
H16C0.26510.84980.37880.051*0.108 (4)
H16D0.28140.74640.38410.051*0.108 (4)
C210.3493 (2)0.75975 (15)0.68163 (11)0.0264 (5)
H210.26570.79040.69730.032*
C220.4611 (3)0.82569 (16)0.66786 (13)0.0330 (6)
H22A0.42210.87090.63550.040*
H22B0.53770.79650.64540.040*
C230.5171 (3)0.86798 (17)0.73597 (13)0.0379 (6)
H23A0.59480.90720.72640.045*
H23B0.44320.90340.75510.045*
C240.5672 (3)0.80077 (18)0.78938 (13)0.0362 (6)
H24A0.59920.83010.83350.043*
H24B0.64670.76860.77210.043*
C250.4515 (3)0.73754 (18)0.80306 (12)0.0373 (6)
H25A0.37470.76910.82340.045*
H25B0.48660.69310.83720.045*
C260.3978 (3)0.69311 (16)0.73545 (11)0.0299 (6)
H26A0.47260.65750.71720.036*
H26B0.32000.65400.74490.036*
C310.0388 (3)0.87665 (16)0.56970 (13)0.0357 (6)
H310.03070.87330.51760.043*
C320.0980 (3)0.8529 (2)0.59833 (16)0.0509 (8)
H32A0.12220.79230.58500.061*
H32B0.17170.89140.57750.061*
C330.0918 (3)0.8612 (2)0.67717 (17)0.0601 (9)
H33A0.18430.84860.69390.072*
H33B0.02540.81810.69830.072*
C340.0470 (4)0.9517 (2)0.70027 (17)0.0666 (11)
H34A0.03780.95420.75190.080*
H34B0.11880.99420.68370.080*
C350.0903 (3)0.9757 (2)0.67149 (16)0.0544 (9)
H35A0.11391.03650.68440.065*
H35B0.16430.93770.69280.065*
C360.0849 (3)0.96641 (17)0.59272 (15)0.0484 (8)
H36A0.01981.00990.57120.058*
H36B0.17790.97820.57630.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0236 (3)0.0221 (3)0.0236 (3)0.0006 (3)0.0005 (2)0.0011 (3)
O10.0207 (8)0.0250 (8)0.0259 (8)0.0037 (7)0.0005 (7)0.0047 (7)
O20.0221 (9)0.0264 (9)0.0283 (8)0.0004 (7)0.0001 (7)0.0059 (7)
O30.0386 (10)0.0255 (9)0.0307 (9)0.0025 (8)0.0080 (8)0.0007 (7)
O40.0300 (9)0.0251 (9)0.0243 (8)0.0028 (7)0.0031 (7)0.0049 (7)
O50.0278 (9)0.0256 (9)0.0272 (9)0.0047 (7)0.0012 (7)0.0014 (7)
C10.0276 (13)0.0312 (14)0.0276 (12)0.0008 (11)0.0023 (10)0.0055 (11)
C20.0232 (13)0.0374 (15)0.0389 (14)0.0027 (11)0.0009 (11)0.0079 (12)
C30.0281 (14)0.0415 (16)0.0372 (15)0.0135 (12)0.0049 (11)0.0058 (12)
C40.0331 (14)0.0329 (14)0.0256 (12)0.0104 (12)0.0001 (11)0.0018 (11)
C4A0.0259 (13)0.0271 (12)0.0190 (11)0.0058 (10)0.0002 (9)0.0056 (10)
C4B0.0294 (13)0.0268 (13)0.0166 (11)0.0046 (10)0.0016 (10)0.0011 (9)
C50.0363 (15)0.0308 (14)0.0264 (13)0.0073 (12)0.0020 (11)0.0075 (11)
C60.0421 (16)0.0290 (14)0.0382 (15)0.0015 (12)0.0076 (12)0.0128 (12)
C70.0303 (14)0.0325 (14)0.0325 (13)0.0025 (11)0.0076 (11)0.0031 (11)
C80.0256 (13)0.0284 (13)0.0242 (12)0.0038 (10)0.0025 (10)0.0016 (10)
C8A0.0262 (13)0.0229 (12)0.0198 (11)0.0036 (10)0.0017 (9)0.0011 (9)
C90.0254 (13)0.0223 (12)0.0176 (11)0.0031 (10)0.0015 (9)0.0025 (9)
C100.0259 (13)0.0214 (12)0.0202 (11)0.0004 (10)0.0013 (10)0.0003 (9)
C10A0.0244 (13)0.0265 (12)0.0197 (11)0.0041 (10)0.0014 (9)0.0054 (10)
C110.039 (2)0.0306 (19)0.029 (2)0.0031 (15)0.0083 (19)0.0003 (15)
C120.0333 (19)0.069 (3)0.050 (2)0.0115 (17)0.0041 (15)0.0207 (18)
C130.046 (2)0.079 (3)0.084 (3)0.016 (2)0.024 (2)0.032 (2)
C140.051 (3)0.057 (3)0.068 (3)0.002 (2)0.034 (2)0.024 (2)
C150.062 (2)0.064 (2)0.0377 (18)0.0020 (19)0.0137 (17)0.0117 (17)
C160.0314 (17)0.054 (2)0.0389 (17)0.0004 (15)0.0005 (13)0.0122 (15)
C210.0268 (13)0.0299 (13)0.0222 (11)0.0024 (11)0.0017 (10)0.0066 (10)
C220.0365 (15)0.0305 (14)0.0316 (14)0.0008 (12)0.0014 (11)0.0029 (11)
C230.0378 (15)0.0355 (15)0.0398 (15)0.0032 (13)0.0006 (12)0.0123 (12)
C240.0310 (14)0.0484 (17)0.0281 (13)0.0039 (13)0.0046 (11)0.0134 (12)
C250.0408 (16)0.0481 (17)0.0228 (12)0.0071 (13)0.0007 (11)0.0035 (12)
C260.0328 (14)0.0324 (14)0.0242 (12)0.0009 (11)0.0009 (11)0.0003 (11)
C310.0406 (16)0.0315 (14)0.0336 (14)0.0140 (12)0.0068 (12)0.0043 (11)
C320.0329 (16)0.0533 (19)0.065 (2)0.0136 (14)0.0069 (14)0.0176 (16)
C330.0445 (19)0.076 (2)0.062 (2)0.0071 (17)0.0219 (16)0.0102 (18)
C340.069 (2)0.083 (3)0.0474 (19)0.036 (2)0.0006 (17)0.0202 (18)
C350.065 (2)0.0374 (17)0.0587 (19)0.0122 (16)0.0117 (17)0.0212 (15)
C360.062 (2)0.0275 (15)0.0547 (18)0.0104 (14)0.0015 (16)0.0024 (13)
Geometric parameters (Å, º) top
P—O31.581 (2)C2—H20.9500
P—O41.589 (2)C3—H30.9500
P—O51.624 (2)C4—H40.9500
P—O21.652 (2)C5—H50.9500
P—O11.744 (2)C6—H60.9500
O1—C91.361 (3)C7—H70.9500
O2—C101.380 (3)C8—H80.9500
O3—C11'1.41 (3)C11—H111.0000
O3—C111.466 (4)C12—H12A0.9900
O4—C211.461 (3)C12—H12B0.9900
O5—C311.443 (3)C13—H13A0.9900
C1—C21.370 (3)C13—H13B0.9900
C1—C10A1.406 (3)C14—H14A0.9900
C2—C31.389 (4)C14—H14B0.9900
C3—C41.373 (4)C15—H15A0.9900
C4—C4A1.408 (3)C15—H15B0.9900
C4A—C10A1.421 (3)C16—H16A0.9900
C4A—C4B1.462 (3)C16—H16B0.9900
C4B—C51.405 (3)C11'—H11'1.0000
C4B—C8A1.422 (3)C12'—H12C0.9900
C5—C61.369 (4)C12'—H12D0.9900
C6—C71.392 (4)C13'—H13C0.9900
C7—C81.370 (3)C13'—H13D0.9900
C8—C8A1.402 (3)C14'—H14C0.9900
C8A—C91.421 (3)C14'—H14D0.9900
C9—C101.332 (3)C15'—H15C0.9900
C10—C10A1.413 (3)C15'—H15D0.9900
C11—C161.508 (5)C16'—H16C0.9900
C11—C121.510 (5)C16'—H16D0.9900
C12—C131.527 (5)C21—H211.0000
C13—C141.515 (6)C22—H22A0.9900
C14—C151.511 (7)C22—H22B0.9900
C15—C161.523 (4)C23—H23A0.9900
C11'—C16'1.502 (18)C23—H23B0.9900
C11'—C12'1.507 (19)C24—H24A0.9900
C12'—C13'1.518 (19)C24—H24B0.9900
C13'—C14'1.515 (19)C25—H25A0.9900
C14'—C15'1.52 (2)C25—H25B0.9900
C15'—C16'1.539 (18)C26—H26A0.9900
C21—C261.508 (3)C26—H26B0.9900
C21—C221.518 (3)C31—H311.0000
C22—C231.527 (3)C32—H32A0.9900
C23—C241.513 (4)C32—H32B0.9900
C24—C251.519 (4)C33—H33A0.9900
C25—C261.527 (3)C33—H33B0.9900
C31—C361.509 (4)C34—H34A0.9900
C31—C321.511 (4)C34—H34B0.9900
C32—C331.516 (4)C35—H35A0.9900
C33—C341.516 (5)C35—H35B0.9900
C34—C351.518 (5)C36—H36A0.9900
C35—C361.516 (4)C36—H36B0.9900
C1—H10.9500
O3—P—O4117.35 (9)C12—C13—H13B109.3
O3—P—O592.73 (9)H13A—C13—H13B107.9
O4—P—O591.98 (8)C15—C14—H14A109.5
O3—P—O2115.31 (9)C13—C14—H14A109.5
O4—P—O2127.24 (9)C15—C14—H14B109.5
O5—P—O288.52 (8)C13—C14—H14B109.5
O3—P—O194.57 (8)H14A—C14—H14B108.1
O4—P—O184.38 (8)C14—C15—H15A109.5
O5—P—O1172.69 (9)C16—C15—H15A109.5
O2—P—O188.66 (8)C14—C15—H15B109.5
C9—O1—P111.78 (14)C16—C15—H15B109.5
C10—O2—P114.68 (14)H15A—C15—H15B108.1
C11'—O3—P129.2 (13)C11—C16—H16A109.4
C11—O3—P131.06 (18)C15—C16—H16A109.4
C21—O4—P126.99 (14)C11—C16—H16B109.4
C31—O5—P124.48 (14)C15—C16—H16B109.4
C2—C1—C10A120.2 (2)H16A—C16—H16B108.0
C1—C2—C3119.9 (2)O3—C11'—H11'111.2
C4—C3—C2121.1 (2)C16'—C11'—H11'111.2
C3—C4—C4A121.0 (2)C12'—C11'—H11'111.2
C4—C4A—C10A117.4 (2)C11'—C12'—H12C109.6
C4—C4A—C4B122.7 (2)C13'—C12'—H12C109.6
C10A—C4A—C4B119.9 (2)C11'—C12'—H12D109.6
C5—C4B—C8A117.0 (2)C13'—C12'—H12D109.6
C5—C4B—C4A122.8 (2)H12C—C12'—H12D108.1
C8A—C4B—C4A120.2 (2)C14'—C13'—H13C109.0
C6—C5—C4B121.6 (2)C12'—C13'—H13C109.0
C5—C6—C7120.9 (2)C14'—C13'—H13D109.0
C8—C7—C6119.4 (2)C12'—C13'—H13D109.0
C7—C8—C8A120.7 (2)H13C—C13'—H13D107.8
C8—C8A—C9122.6 (2)C13'—C14'—H14C109.4
C8—C8A—C4B120.4 (2)C15'—C14'—H14C109.4
C9—C8A—C4B117.0 (2)C13'—C14'—H14D109.4
C10—C9—O1112.9 (2)C15'—C14'—H14D109.4
C10—C9—C8A122.0 (2)H14C—C14'—H14D108.0
O1—C9—C8A125.0 (2)C14'—C15'—H15C110.0
C9—C10—O2111.76 (19)C16'—C15'—H15C110.0
C9—C10—C10A124.5 (2)C14'—C15'—H15D110.0
O2—C10—C10A123.8 (2)C16'—C15'—H15D110.0
C1—C10A—C10123.3 (2)H15C—C15'—H15D108.4
C1—C10A—C4A120.4 (2)C11'—C16'—H16C109.3
C10—C10A—C4A116.3 (2)C15'—C16'—H16C109.3
O3—C11—C16106.4 (3)C11'—C16'—H16D109.3
O3—C11—C12108.5 (3)C15'—C16'—H16D109.3
C16—C11—C12111.4 (3)H16C—C16'—H16D108.0
C11—C12—C13110.9 (3)O4—C21—H21109.6
C14—C13—C12111.8 (3)C26—C21—H21109.6
C15—C14—C13110.8 (4)C22—C21—H21109.6
C14—C15—C16110.6 (3)C21—C22—H22A109.5
C11—C16—C15111.1 (3)C23—C22—H22A109.5
O3—C11'—C16'106 (2)C21—C22—H22B109.5
O3—C11'—C12'106 (2)C23—C22—H22B109.5
C16'—C11'—C12'111.3 (19)H22A—C22—H22B108.1
C11'—C12'—C13'110.3 (19)C24—C23—H23A109.3
C14'—C13'—C12'113 (2)C22—C23—H23A109.3
C13'—C14'—C15'111 (2)C24—C23—H23B109.3
C14'—C15'—C16'108 (2)C22—C23—H23B109.3
C11'—C16'—C15'111.4 (19)H23A—C23—H23B108.0
O4—C21—C26106.26 (18)C23—C24—H24A109.6
O4—C21—C22109.17 (18)C25—C24—H24A109.6
C26—C21—C22112.5 (2)C23—C24—H24B109.6
C21—C22—C23110.5 (2)C25—C24—H24B109.6
C24—C23—C22111.6 (2)H24A—C24—H24B108.1
C23—C24—C25110.5 (2)C24—C25—H25A109.5
C24—C25—C26110.6 (2)C26—C25—H25A109.5
C21—C26—C25110.5 (2)C24—C25—H25B109.5
O5—C31—C36107.0 (2)C26—C25—H25B109.5
O5—C31—C32108.6 (2)H25A—C25—H25B108.1
C36—C31—C32111.3 (2)C21—C26—H26A109.6
C31—C32—C33111.5 (2)C25—C26—H26A109.6
C34—C33—C32111.2 (3)C21—C26—H26B109.6
C33—C34—C35110.9 (3)C25—C26—H26B109.6
C36—C35—C34111.6 (3)H26A—C26—H26B108.1
C31—C36—C35111.6 (2)O5—C31—H31110.0
C2—C1—H1119.9C36—C31—H31110.0
C10A—C1—H1119.9C32—C31—H31110.0
C1—C2—H2120.1C31—C32—H32A109.3
C3—C2—H2120.1C33—C32—H32A109.3
C4—C3—H3119.5C31—C32—H32B109.3
C2—C3—H3119.5C33—C32—H32B109.3
C3—C4—H4119.5H32A—C32—H32B108.0
C4A—C4—H4119.5C34—C33—H33A109.4
C6—C5—H5119.2C32—C33—H33A109.4
C4B—C5—H5119.2C34—C33—H33B109.4
C5—C6—H6119.5C32—C33—H33B109.4
C7—C6—H6119.5H33A—C33—H33B108.0
C8—C7—H7120.3C33—C34—H34A109.5
C6—C7—H7120.3C35—C34—H34A109.5
C7—C8—H8119.7C33—C34—H34B109.5
C8A—C8—H8119.7C35—C34—H34B109.5
O3—C11—H11110.2H34A—C34—H34B108.1
C16—C11—H11110.2C36—C35—H35A109.3
C12—C11—H11110.2C34—C35—H35A109.3
C11—C12—H12A109.5C36—C35—H35B109.3
C13—C12—H12A109.5C34—C35—H35B109.3
C11—C12—H12B109.5H35A—C35—H35B108.0
C13—C12—H12B109.5C31—C36—H36A109.3
H12A—C12—H12B108.0C35—C36—H36A109.3
C14—C13—H13A109.3C31—C36—H36B109.3
C12—C13—H13A109.3C35—C36—H36B109.3
C14—C13—H13B109.3H36A—C36—H36B108.0
O3—P—O1—C9112.19 (15)C2—C1—C10A—C10178.0 (2)
O4—P—O1—C9130.72 (15)C2—C1—C10A—C4A1.3 (3)
O2—P—O1—C93.09 (14)C9—C10—C10A—C1176.1 (2)
O3—P—O2—C1090.33 (16)O2—C10—C10A—C14.1 (3)
O4—P—O2—C1085.99 (16)C9—C10—C10A—C4A3.2 (3)
O5—P—O2—C10177.35 (15)O2—C10—C10A—C4A176.57 (19)
O1—P—O2—C104.09 (15)C4—C4A—C10A—C10.4 (3)
O4—P—O3—C11'68.5 (13)C4B—C4A—C10A—C1179.6 (2)
O5—P—O3—C11'162.2 (13)C4—C4A—C10A—C10178.9 (2)
O2—P—O3—C11'108.2 (13)C4B—C4A—C10A—C101.1 (3)
O1—P—O3—C11'17.5 (13)C11'—O3—C11—C16131 (4)
O4—P—O3—C1191.9 (3)P—O3—C11—C16137.5 (2)
O5—P—O3—C11174.4 (3)C11'—O3—C11—C1211 (4)
O2—P—O3—C1184.8 (3)P—O3—C11—C12102.6 (3)
O1—P—O3—C115.9 (3)O3—C11—C12—C13171.5 (3)
O3—P—O4—C2170.2 (2)C16—C11—C12—C1354.8 (4)
O5—P—O4—C2123.95 (19)C11—C12—C13—C1454.3 (5)
O2—P—O4—C21113.59 (18)C12—C13—C14—C1555.3 (6)
O1—P—O4—C21162.40 (18)C13—C14—C15—C1656.4 (5)
O3—P—O5—C3161.73 (19)O3—C11—C16—C15174.6 (3)
O4—P—O5—C31179.24 (19)C12—C11—C16—C1556.6 (4)
O2—P—O5—C3153.54 (19)C14—C15—C16—C1157.2 (5)
C10A—C1—C2—C31.3 (4)C11—O3—C11'—C16'3 (3)
C1—C2—C3—C40.4 (4)P—O3—C11'—C16'101 (2)
C2—C3—C4—C4A0.5 (4)C11—O3—C11'—C12'115 (5)
C3—C4—C4A—C10A0.5 (3)P—O3—C11'—C12'141.3 (14)
C3—C4—C4A—C4B179.5 (2)O3—C11'—C12'—C13'169 (2)
C4—C4A—C4B—C55.1 (3)C16'—C11'—C12'—C13'55 (3)
C10A—C4A—C4B—C5174.9 (2)C11'—C12'—C13'—C14'53 (4)
C4—C4A—C4B—C8A176.2 (2)C12'—C13'—C14'—C15'55 (5)
C10A—C4A—C4B—C8A3.8 (3)C13'—C14'—C15'—C16'56 (5)
C8A—C4B—C5—C60.6 (3)O3—C11'—C16'—C15'174 (2)
C4A—C4B—C5—C6178.1 (2)C12'—C11'—C16'—C15'59 (3)
C4B—C5—C6—C70.4 (4)C14'—C15'—C16'—C11'59 (3)
C5—C6—C7—C80.7 (4)P—O4—C21—C26163.00 (16)
C6—C7—C8—C8A1.7 (4)P—O4—C21—C2275.4 (2)
C7—C8—C8A—C9175.0 (2)O4—C21—C22—C23171.86 (19)
C7—C8—C8A—C4B1.6 (3)C26—C21—C22—C2354.2 (3)
C5—C4B—C8A—C80.4 (3)C21—C22—C23—C2454.5 (3)
C4A—C4B—C8A—C8179.1 (2)C22—C23—C24—C2556.9 (3)
C5—C4B—C8A—C9176.4 (2)C23—C24—C25—C2657.8 (3)
C4A—C4B—C8A—C92.3 (3)O4—C21—C26—C25174.94 (19)
P—O1—C9—C101.4 (2)C22—C21—C26—C2555.5 (3)
P—O1—C9—C8A177.88 (17)C24—C25—C26—C2156.9 (3)
C8—C8A—C9—C10174.9 (2)P—O5—C31—C36127.2 (2)
C4B—C8A—C9—C101.8 (3)P—O5—C31—C32112.5 (2)
C8—C8A—C9—O11.3 (3)O5—C31—C32—C3362.4 (3)
C4B—C8A—C9—O1178.00 (19)C36—C31—C32—C3355.2 (3)
O1—C9—C10—O21.6 (3)C31—C32—C33—C3455.8 (3)
C8A—C9—C10—O2175.00 (18)C32—C33—C34—C3555.4 (4)
O1—C9—C10—C10A178.6 (2)C33—C34—C35—C3654.9 (4)
C8A—C9—C10—C10A4.8 (3)O5—C31—C36—C3563.9 (3)
P—O2—C10—C94.2 (2)C32—C31—C36—C3554.6 (3)
P—O2—C10—C10A176.06 (17)C34—C35—C36—C3154.7 (3)

Experimental details

Crystal data
Chemical formulaC32H41O5P
Mr536.62
Crystal system, space groupMonoclinic, P21/n
Temperature (K)143
a, b, c (Å)9.665 (2), 15.394 (3), 19.200 (4)
β (°) 93.92 (2)
V3)2850.1 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.65 × 0.30 × 0.30
Data collection
DiffractometerStoe STADI-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5588, 5037, 3708
Rint0.024
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.119, 1.04
No. of reflections5037
No. of parameters368
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.31

Computer programs: DIF4 (Stoe & Cie, 1992), DIF4, REDU4 (Stoe & Cie, 1992), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) top
P—O31.581 (2)P—O21.652 (2)
P—O41.589 (2)P—O11.744 (2)
P—O51.624 (2)
O3—P—O4117.35 (9)O5—P—O288.52 (8)
O3—P—O592.73 (9)O3—P—O194.57 (8)
O4—P—O591.98 (8)O4—P—O184.38 (8)
O3—P—O2115.31 (9)O5—P—O1172.69 (9)
O4—P—O2127.24 (9)O2—P—O188.66 (8)
 

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