Di­phenyl (3,3-di­phenoxy­cyclo­hexyl)­phospho­nate

Guzei, I.A.; Stockland, R. Jr; Tennis, T.W.

doi:10.1107/S160053680202370X

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Diphenyl (3,3-diphenoxycyclohexyl)phosphonate

I. A. Guzei, R. Stockland Jr and T. W. Tennis

The solid-state structure of the title compound, C₃₀H₂₉O₅P, has been determined at 100 K. The generalized puckering coordinates, Q₂ (0.587), φ₂ (286.82°) and θ₂ (178.9°), confirm that the cyclohexane ring is in the chair conformation ²C₅. The phosphine ligand is equatorial to the ring, with the P atom in a slightly distorted tetrahedral configuration.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680202370X/fl6013sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680202370X/fl6013Isup2.hkl Contains datablock I

CCDC reference: 204678

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.010 Å
R factor = 0.069
wR factor = 0.165
Data-to-parameter ratio = 9.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5833

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.49
         From the CIF: _reflns_number_total               3050
         Count of symmetry unique reflns         2284
         Completeness (_total/calc)            133.54%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       766
         Fraction of Friedel pairs measured     0.335
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Over the last few decades, P—C bond forming reactions have received considerable attention since the resulting compounds have applications in organic and medicinal chemistry (Jung & McClure, 1991; Mori et al., 1995; Errington et al., 1997). Much of the recent work is complementary to the existing Arbusov and Pudovick processes (Bhattacharya & Thyagarajan, 1981, Pudovik & Konovalova, 1979), however, a limitation of all of this chemistry is the fact that triarylphosphites are generally unreactive. For example, it is well known that trialkylphosphites such as P(OEt)₃ are converted into γ-keto phosphonates upon treatment with Michael acceptors, while analogous reactions employing triarylphosphites are rare (Harvey, 1996). In order to probe this reaction further, we have studied the reaction of cyclohexenenone with triphenylphosphite.

Heating a solution of cyclohexenone in phenol with triphenylphosphite afforded a dark solid. Distillation (0.05 mm H g) of this residue followed by purification (column chromatography) afforded a colorless solid. Instead of generating the addition product, the title compound, (I), was isolated. While a number of complexes containing this gem-aryloxide group have been reported, few contain a cyclohexane ring (Peters et al., 1998; Gawronski et al., 1989; Harada et al., 1994, 1997).

This work presents a noteworthy side reaction available to triarylphosphites, although the precise mechanism is not clear,

The central six-membered ring in (I) is in the chair conformation. Four ring C atoms C1, C3, C4, and C6 are coplanar within 0.01 Å, while C2 is situated 0.69 (1) Å above and C5 − 0.68 (1) Å below the plane. The C2 and C5 dihedral flap angles are 51.8 (4) and 51.2 (4)° relative to the four-carbon plane, respectively. This yields an almost undistorted ²C₅ conformation for the central six-membered ring, which is reaffirmed by the generalized puckering coordinates q₂ [0.0115 (7)], ϕ₂ [−75 (34)°] and θ₂ [178.9 (7)°] (Nardelli, 1995; Giacovazzo et al., 1998).

A Cambridge Structural Database (Allen, 2002) search returned three relevant molecules with the phosphine–cyclohexane skeleton and similar substitution pattern to that of (I). These molecules, 1-hydroxycyclohexanephosphonic acid, (II) (Ohms et al., 1996), 8-cyclohexyl-16H-dinaphto[2,1 − d:1',2'-g][1,3,2]dioxaphosphocine-8-oxide, (III) (Naidu et al. 1992), and (-)-diethyl3-hydroxy-3-(2-trityl-1,2,4-triazol-3-yl)cyclohexylphosphonate, (IV) (Mori et al., 1995), contain equatorial phosphine ligands and low-energy chair conformation cyclohexane rings.

The phosphine ligand is bound to atom C1, the only chiral C atom in the molecule. The absolute configuration about the chiral atom could not be unequivocally established. Bond distances for the phosphine ligand are listed below and are in good agreement with the corresponding averages of (II)–(IV) given in brackets: 1.467 (5) Å for P═O₁ [average 1.47 (2) Å], 1.595 (4) Å for P—O [average 1.58 (3) Å], and 1.797 (6) Å for P—C₁ [average 1.80 (2)]. The P atom is in a slightly distorted tetrahedral configuration with the angles about it ranging between 101.0 (2)–116.0 (2)°.

Experimental top

Phenol (50.0 ml, dried) was heated to 323 K in a clean dry flask under nitrogen. While stirring, triphenylphosphite (8.7 mmol; Aldrich) and cyclohexenone (10.3 mmol; Aldrich) were added and the temperature was increased to 373 K for 36 h. The product was distilled under vacuum (0.05 mm H g) and purified by column chromatography (silica gel; hexane/EtOAc 7:3). After collecting fractions, the product crystallized from the solution. The crystals were collected on a filterm washed with hexanes and dried (0.020 g).

Computing details top

Data collection: SMART (Bruker, 2000-2001); cell refinement: SAINT (Bruker, 2000-2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000-2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I). The displacement ellipsoids are shown at the 50% probability level.

(3, 3-dephenoxy-cyclohexyl)-phosphonic acid diphenyl ester top

Crystal data top

C₃₀H₂₉O₅P	F(000) = 528
M_r = 500.50	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 13.612 (3) Å	Cell parameters from 528 reflections
b = 5.8536 (11) Å	θ = 2.4–24.5°
c = 16.900 (3) Å	µ = 0.15 mm⁻¹
β = 112.63 (1)°	T = 100 K
V = 1242.9 (4) Å³	Needle, colorless
Z = 2	0.52 × 0.12 × 0.10 mm

Data collection top

Bruker CCD-1000 area-detector diffractometer	3050 independent reflections
Radiation source: fine-focus sealed tube	2482 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ϕ and ω scans	θ_max = 24.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000-2001)	h = −15→15
T_min = 0.926, T_max = 0.985	k = −6→6
5397 measured reflections	l = −19→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0897P)² + 0.2739P] where P = (F_o² + 2F_c²)/3
3050 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.48 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₃₀H₂₉O₅P	V = 1242.9 (4) Å³
M_r = 500.50	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 13.612 (3) Å	µ = 0.15 mm⁻¹
b = 5.8536 (11) Å	T = 100 K
c = 16.900 (3) Å	0.52 × 0.12 × 0.10 mm
β = 112.63 (1)°

Data collection top

Bruker CCD-1000 area-detector diffractometer	3050 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000-2001)	2482 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.985	R_int = 0.064
5397 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.165	H-atom parameters constrained
S = 1.02	Δρ_max = 0.48 e Å⁻³
3050 reflections	Δρ_min = −0.32 e Å⁻³
325 parameters

Special details top

Experimental. SADABS V.2.03, Bruker-AXS, 2001.

¹H NMR (300 mHz, CDCl₃, 25 °C): δ 7.2 − 6.7 (m, 1H, Ar—H), 2.81 (m, 1H, –CH₂–), 2.50–2.23 (m, 2H, –CH₂–), 2.17(m, 1H, –CH₂–), 1.85 (m, 1H, CHP(O)), 1.17 (m, 1H, –CH₂–), 1.57 (m, 2H, –CH₂–). ³¹P{¹H} NMR (121 mHz, CDCl₃, 25 °C): δ 24.9 p.p.m..

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P	0.49776 (11)	0.6966 (3)	0.30138 (10)	0.0190 (4)
O1	0.5337 (3)	0.8969 (7)	0.3574 (3)	0.0243 (11)
O2	0.5894 (3)	0.5132 (7)	0.3122 (2)	0.0206 (10)
O3	0.4551 (3)	0.7453 (7)	0.2012 (3)	0.0230 (11)
O4	0.2211 (3)	0.0327 (7)	0.2045 (2)	0.0211 (10)
O5	0.1743 (3)	0.3938 (7)	0.2442 (2)	0.0201 (10)
C1	0.3893 (5)	0.5426 (12)	0.3121 (4)	0.0200 (14)
H1	0.3295	0.6529	0.3017	0.024*
C2	0.3471 (4)	0.3453 (11)	0.2472 (4)	0.0177 (15)
H2A	0.3221	0.4061	0.1881	0.021*
H2B	0.4050	0.2347	0.2548	0.021*
C3	0.2567 (4)	0.2273 (11)	0.2612 (4)	0.0188 (15)
C4	0.2910 (5)	0.1352 (10)	0.3510 (4)	0.0187 (15)
H4A	0.3479	0.0202	0.3610	0.022*
H4B	0.2300	0.0591	0.3581	0.022*
C5	0.3322 (4)	0.3280 (12)	0.4166 (4)	0.0226 (15)
H5A	0.2737	0.4369	0.4095	0.027*
H5B	0.3566	0.2638	0.4752	0.027*
C6	0.4232 (5)	0.4523 (11)	0.4052 (4)	0.0226 (16)
H6A	0.4844	0.3473	0.4183	0.027*
H6B	0.4459	0.5820	0.4458	0.027*
C7	0.6882 (4)	0.5091 (11)	0.3821 (4)	0.0170 (14)
C8	0.7552 (4)	0.6977 (13)	0.3980 (4)	0.0233 (15)
H8	0.7353	0.8302	0.3630	0.028*
C9	0.8519 (5)	0.6849 (13)	0.4671 (4)	0.0265 (16)
H9	0.8988	0.8122	0.4807	0.032*
C10	0.8809 (5)	0.4908 (14)	0.5162 (4)	0.0292 (17)
H10	0.9479	0.4841	0.5630	0.035*
C11	0.8135 (5)	0.3065 (12)	0.4979 (4)	0.0269 (16)
H11	0.8341	0.1722	0.5319	0.032*
C12	0.7161 (5)	0.3150 (11)	0.4307 (4)	0.0222 (15)
H12	0.6690	0.1882	0.4182	0.027*
C13	0.5246 (4)	0.7947 (11)	0.1603 (4)	0.0203 (16)
C14	0.5382 (5)	0.6380 (12)	0.1049 (4)	0.0306 (18)
H14	0.5007	0.4971	0.0953	0.037*
C15	0.6044 (5)	0.6816 (13)	0.0637 (4)	0.0316 (17)
H15	0.6120	0.5723	0.0249	0.038*
C16	0.6603 (5)	0.8827 (13)	0.0779 (4)	0.0328 (18)
H16	0.7082	0.9114	0.0504	0.039*
C17	0.6460 (5)	1.0447 (13)	0.1331 (4)	0.0302 (17)
H17	0.6829	1.1861	0.1416	0.036*
C18	0.5791 (4)	1.0024 (12)	0.1754 (4)	0.0221 (15)
H18	0.5704	1.1116	0.2138	0.026*
C19	0.1878 (4)	0.0602 (12)	0.1171 (4)	0.0192 (15)
C20	0.1299 (5)	0.2436 (12)	0.0703 (4)	0.0294 (17)
H20	0.1140	0.3691	0.0990	0.035*
C21	0.0952 (5)	0.2441 (12)	−0.0184 (4)	0.0281 (17)
H21	0.0567	0.3714	−0.0503	0.034*
C22	0.1166 (5)	0.0605 (13)	−0.0606 (4)	0.0304 (17)
H22	0.0919	0.0594	−0.1214	0.036*
C23	0.1734 (5)	−0.1185 (13)	−0.0140 (4)	0.0322 (17)
H23	0.1890	−0.2439	−0.0429	0.039*
C24	0.2085 (5)	−0.1224 (13)	0.0736 (4)	0.0286 (17)
H24	0.2473	−0.2506	0.1046	0.034*
C25	0.0850 (4)	0.3503 (11)	0.2601 (3)	0.0179 (15)
C26	0.0252 (5)	0.1469 (10)	0.2362 (4)	0.0206 (15)
H26	0.0484	0.0246	0.2107	0.025*
C27	−0.0682 (5)	0.1291 (12)	0.2507 (4)	0.0280 (17)
H27	−0.1098	−0.0060	0.2340	0.034*
C28	−0.1019 (5)	0.3054 (13)	0.2891 (4)	0.0337 (18)
H28	−0.1653	0.2911	0.2995	0.040*
C29	−0.0421 (5)	0.5000 (14)	0.3115 (4)	0.0330 (18)
H29	−0.0644	0.6209	0.3383	0.040*
C30	0.0491 (5)	0.5248 (13)	0.2964 (4)	0.0275 (16)
H30	0.0880	0.6638	0.3110	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0229 (8)	0.0140 (10)	0.0159 (9)	−0.0017 (8)	0.0028 (6)	0.0001 (8)
O1	0.033 (2)	0.014 (3)	0.019 (2)	−0.005 (2)	0.0027 (19)	−0.008 (2)
O2	0.023 (2)	0.016 (3)	0.015 (2)	−0.0009 (19)	−0.0014 (18)	−0.002 (2)
O3	0.019 (2)	0.023 (3)	0.023 (2)	−0.0047 (19)	0.0037 (18)	0.004 (2)
O4	0.035 (2)	0.009 (2)	0.012 (2)	−0.004 (2)	0.0010 (18)	0.002 (2)
O5	0.023 (2)	0.015 (2)	0.016 (2)	0.0036 (19)	0.0007 (18)	−0.004 (2)
C1	0.025 (3)	0.014 (4)	0.014 (3)	0.000 (3)	0.000 (3)	−0.002 (3)
C2	0.023 (3)	0.016 (4)	0.008 (3)	0.007 (3)	0.000 (2)	0.001 (3)
C3	0.026 (3)	0.012 (4)	0.016 (3)	−0.001 (3)	0.004 (3)	0.002 (3)
C4	0.024 (3)	0.010 (4)	0.024 (4)	−0.005 (3)	0.010 (3)	0.000 (3)
C5	0.029 (3)	0.027 (4)	0.013 (3)	0.000 (3)	0.010 (3)	0.007 (3)
C6	0.030 (4)	0.017 (4)	0.012 (3)	0.000 (3)	−0.002 (3)	0.000 (3)
C7	0.014 (3)	0.015 (4)	0.018 (3)	0.002 (3)	0.002 (3)	−0.001 (3)
C8	0.023 (3)	0.019 (4)	0.024 (3)	0.002 (3)	0.006 (3)	−0.003 (4)
C9	0.029 (3)	0.025 (4)	0.021 (4)	−0.005 (4)	0.006 (3)	−0.008 (4)
C10	0.017 (3)	0.040 (5)	0.024 (4)	0.005 (3)	0.001 (3)	−0.003 (4)
C11	0.035 (4)	0.021 (4)	0.019 (3)	0.012 (3)	0.004 (3)	0.005 (3)
C12	0.035 (4)	0.014 (4)	0.015 (3)	0.001 (3)	0.008 (3)	0.001 (3)
C13	0.018 (3)	0.013 (4)	0.019 (4)	−0.001 (3)	−0.006 (3)	0.005 (3)
C14	0.040 (4)	0.027 (5)	0.016 (4)	−0.005 (3)	0.001 (3)	−0.001 (3)
C15	0.046 (4)	0.022 (4)	0.025 (4)	0.006 (4)	0.013 (3)	−0.005 (4)
C16	0.035 (4)	0.031 (5)	0.030 (4)	0.001 (4)	0.009 (3)	0.009 (4)
C17	0.029 (4)	0.021 (4)	0.032 (4)	−0.002 (3)	0.002 (3)	0.013 (4)
C18	0.022 (3)	0.020 (4)	0.016 (3)	0.005 (3)	−0.001 (3)	−0.001 (3)
C19	0.021 (3)	0.018 (4)	0.016 (3)	−0.003 (3)	0.004 (3)	−0.003 (3)
C20	0.039 (4)	0.020 (4)	0.024 (4)	0.005 (3)	0.007 (3)	−0.003 (4)
C21	0.035 (4)	0.022 (4)	0.022 (4)	−0.004 (3)	0.004 (3)	0.002 (4)
C22	0.035 (4)	0.041 (5)	0.013 (3)	−0.012 (4)	0.006 (3)	−0.007 (4)
C23	0.037 (4)	0.029 (5)	0.026 (4)	0.003 (4)	0.007 (3)	−0.011 (4)
C24	0.026 (4)	0.029 (4)	0.028 (4)	0.002 (3)	0.006 (3)	−0.006 (4)
C25	0.022 (3)	0.022 (4)	0.008 (3)	0.011 (3)	0.005 (3)	0.000 (3)
C26	0.035 (4)	0.005 (4)	0.017 (3)	−0.002 (3)	0.004 (3)	−0.002 (3)
C27	0.027 (4)	0.026 (4)	0.026 (4)	−0.006 (3)	0.004 (3)	−0.003 (3)
C28	0.030 (4)	0.044 (5)	0.026 (4)	0.008 (4)	0.008 (3)	0.006 (4)
C29	0.040 (4)	0.031 (5)	0.021 (4)	0.006 (4)	0.005 (3)	−0.007 (4)
C30	0.028 (4)	0.033 (4)	0.018 (4)	0.005 (3)	0.004 (3)	−0.003 (4)

Geometric parameters (Å, º) top

P—O1	1.468 (4)	C12—H12	0.9500
P—O3	1.589 (4)	C13—C14	1.372 (9)
P—O2	1.602 (4)	C13—C18	1.396 (9)
P—C1	1.798 (6)	C14—C15	1.359 (9)
O2—C7	1.408 (6)	C14—H14	0.9500
O3—C13	1.401 (7)	C15—C16	1.371 (10)
O4—C19	1.378 (7)	C15—H15	0.9500
O4—C3	1.447 (7)	C16—C17	1.395 (10)
O5—C25	1.366 (7)	C16—H16	0.9500
O5—C3	1.429 (7)	C17—C18	1.379 (9)
C1—C2	1.543 (9)	C17—H17	0.9500
C1—C6	1.552 (8)	C18—H18	0.9500
C1—H1	1.0000	C19—C24	1.387 (9)
C2—C3	1.507 (8)	C19—C20	1.385 (9)
C2—H2A	0.9900	C20—C21	1.388 (9)
C2—H2B	0.9900	C20—H20	0.9500
C3—C4	1.506 (8)	C21—C22	1.381 (10)
C4—C5	1.529 (9)	C21—H21	0.9500
C4—H4A	0.9900	C22—C23	1.359 (10)
C4—H4B	0.9900	C22—H22	0.9500
C5—C6	1.511 (8)	C23—C24	1.370 (9)
C5—H5A	0.9900	C23—H23	0.9500
C5—H5B	0.9900	C24—H24	0.9500
C6—H6A	0.9900	C25—C30	1.374 (9)
C6—H6B	0.9900	C25—C26	1.411 (9)
C7—C12	1.367 (9)	C26—C27	1.388 (9)
C7—C8	1.391 (9)	C26—H26	0.9500
C8—C9	1.385 (8)	C27—C28	1.387 (9)
C8—H8	0.9500	C27—H27	0.9500
C9—C10	1.372 (10)	C28—C29	1.366 (10)
C9—H9	0.9500	C28—H28	0.9500
C10—C11	1.373 (10)	C29—C30	1.369 (9)
C10—H10	0.9500	C29—H29	0.9500
C11—C12	1.375 (8)	C30—H30	0.9500
C11—H11	0.9500

O1—P—O3	116.0 (2)	C10—C11—H11	119.8
O1—P—O2	114.2 (2)	C12—C11—H11	119.8
O3—P—O2	101.0 (2)	C7—C12—C11	118.9 (6)
O1—P—C1	114.7 (3)	C7—C12—H12	120.5
O3—P—C1	102.7 (2)	C11—C12—H12	120.5
O2—P—C1	106.6 (3)	C14—C13—C18	120.3 (6)
C7—O2—P	123.9 (4)	C14—C13—O3	119.5 (5)
C13—O3—P	121.6 (3)	C18—C13—O3	120.2 (6)
C19—O4—C3	120.4 (5)	C15—C14—C13	120.9 (6)
C25—O5—C3	121.5 (5)	C15—C14—H14	119.5
C2—C1—C6	110.5 (5)	C13—C14—H14	119.5
C2—C1—P	113.5 (4)	C14—C15—C16	120.3 (7)
C6—C1—P	109.7 (4)	C14—C15—H15	119.9
C2—C1—H1	107.6	C16—C15—H15	119.9
C6—C1—H1	107.6	C15—C16—C17	119.3 (6)
P—C1—H1	107.6	C15—C16—H16	120.3
C3—C2—C1	109.6 (5)	C17—C16—H16	120.3
C3—C2—H2A	109.8	C18—C17—C16	120.9 (7)
C1—C2—H2A	109.8	C18—C17—H17	119.5
C3—C2—H2B	109.8	C16—C17—H17	119.5
C1—C2—H2B	109.8	C17—C18—C13	118.2 (6)
H2A—C2—H2B	108.2	C17—C18—H18	120.9
O5—C3—O4	111.5 (4)	C13—C18—H18	120.9
O5—C3—C4	111.2 (5)	O4—C19—C24	115.3 (6)
O4—C3—C4	106.3 (5)	O4—C19—C20	125.6 (6)
O5—C3—C2	106.3 (5)	C24—C19—C20	118.8 (6)
O4—C3—C2	110.1 (5)	C19—C20—C21	120.0 (6)
C4—C3—C2	111.5 (5)	C19—C20—H20	120.0
C3—C4—C5	110.6 (5)	C21—C20—H20	120.0
C3—C4—H4A	109.5	C22—C21—C20	120.3 (6)
C5—C4—H4A	109.5	C22—C21—H21	119.9
C3—C4—H4B	109.5	C20—C21—H21	119.9
C5—C4—H4B	109.5	C23—C22—C21	119.1 (6)
H4A—C4—H4B	108.1	C23—C22—H22	120.4
C6—C5—C4	110.6 (5)	C21—C22—H22	120.4
C6—C5—H5A	109.5	C22—C23—C24	121.5 (7)
C4—C5—H5A	109.5	C22—C23—H23	119.2
C6—C5—H5B	109.5	C24—C23—H23	119.2
C4—C5—H5B	109.5	C23—C24—C19	120.1 (7)
H5A—C5—H5B	108.1	C23—C24—H24	119.9
C5—C6—C1	110.8 (5)	C19—C24—H24	119.9
C5—C6—H6A	109.5	O5—C25—C30	116.4 (6)
C1—C6—H6A	109.5	O5—C25—C26	124.1 (5)
C5—C6—H6B	109.5	C30—C25—C26	119.4 (5)
C1—C6—H6B	109.5	C27—C26—C25	118.7 (6)
H6A—C6—H6B	108.1	C27—C26—H26	120.7
C12—C7—C8	122.2 (5)	C25—C26—H26	120.7
C12—C7—O2	118.3 (5)	C26—C27—C28	121.1 (6)
C8—C7—O2	119.5 (5)	C26—C27—H27	119.5
C9—C8—C7	117.4 (6)	C28—C27—H27	119.5
C9—C8—H8	121.3	C29—C28—C27	118.8 (6)
C7—C8—H8	121.3	C29—C28—H28	120.6
C10—C9—C8	120.9 (7)	C27—C28—H28	120.6
C10—C9—H9	119.5	C28—C29—C30	121.5 (7)
C8—C9—H9	119.5	C28—C29—H29	119.2
C11—C10—C9	120.2 (6)	C30—C29—H29	119.2
C11—C10—H10	119.9	C29—C30—C25	120.5 (7)
C9—C10—H10	119.9	C29—C30—H30	119.7
C10—C11—C12	120.4 (6)	C25—C30—H30	119.7

O1—P—O2—C7	15.4 (5)	C8—C9—C10—C11	−0.7 (9)
O3—P—O2—C7	140.6 (4)	C9—C10—C11—C12	−0.4 (10)
C1—P—O2—C7	−112.4 (5)	C8—C7—C12—C11	0.3 (9)
O1—P—O3—C13	75.2 (5)	O2—C7—C12—C11	178.5 (5)
O2—P—O3—C13	−48.9 (5)	C10—C11—C12—C7	0.6 (9)
C1—P—O3—C13	−159.0 (5)	P—O3—C13—C14	110.4 (5)
O1—P—C1—C2	175.2 (4)	P—O3—C13—C18	−70.0 (7)
O3—P—C1—C2	48.4 (5)	C18—C13—C14—C15	−0.2 (9)
O2—P—C1—C2	−57.3 (5)	O3—C13—C14—C15	179.5 (6)
O1—P—C1—C6	−60.7 (5)	C13—C14—C15—C16	1.0 (10)
O3—P—C1—C6	172.6 (4)	C14—C15—C16—C17	−1.9 (10)
O2—P—C1—C6	66.8 (5)	C15—C16—C17—C18	2.0 (10)
C6—C1—C2—C3	56.3 (6)	C16—C17—C18—C13	−1.2 (9)
P—C1—C2—C3	−179.9 (4)	C14—C13—C18—C17	0.2 (8)
C25—O5—C3—O4	67.4 (6)	O3—C13—C18—C17	−179.4 (5)
C25—O5—C3—C4	−51.1 (7)	C3—O4—C19—C24	147.4 (5)
C25—O5—C3—C2	−172.6 (5)	C3—O4—C19—C20	−37.6 (8)
C19—O4—C3—O5	60.9 (6)	O4—C19—C20—C21	−175.8 (5)
C19—O4—C3—C4	−177.7 (4)	C24—C19—C20—C21	−1.0 (9)
C19—O4—C3—C2	−56.8 (6)	C19—C20—C21—C22	1.1 (9)
C1—C2—C3—O5	62.8 (5)	C20—C21—C22—C23	−1.1 (9)
C1—C2—C3—O4	−176.3 (4)	C21—C22—C23—C24	0.9 (10)
C1—C2—C3—C4	−58.5 (7)	C22—C23—C24—C19	−0.9 (10)
O5—C3—C4—C5	−59.4 (6)	O4—C19—C24—C23	176.2 (6)
O4—C3—C4—C5	179.1 (4)	C20—C19—C24—C23	0.9 (9)
C2—C3—C4—C5	59.1 (7)	C3—O5—C25—C30	138.4 (5)
C3—C4—C5—C6	−57.3 (6)	C3—O5—C25—C26	−46.2 (7)
C4—C5—C6—C1	55.8 (7)	O5—C25—C26—C27	−175.6 (5)
C2—C1—C6—C5	−55.8 (7)	C30—C25—C26—C27	−0.3 (8)
P—C1—C6—C5	178.3 (5)	C25—C26—C27—C28	−1.0 (9)
P—O2—C7—C12	121.8 (5)	C26—C27—C28—C29	0.9 (10)
P—O2—C7—C8	−60.0 (7)	C27—C28—C29—C30	0.5 (10)
C12—C7—C8—C9	−1.4 (9)	C28—C29—C30—C25	−1.9 (10)
O2—C7—C8—C9	−179.5 (5)	O5—C25—C30—C29	177.5 (5)
C7—C8—C9—C10	1.5 (9)	C26—C25—C30—C29	1.8 (9)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₉O₅P
M_r	500.50
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	13.612 (3), 5.8536 (11), 16.900 (3)
β (°)	112.63 (1)
V (Å³)	1242.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.52 × 0.12 × 0.10

Data collection
Diffractometer	Bruker CCD-1000 area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000-2001)
T_min, T_max	0.926, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5397, 3050, 2482
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.583

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.165, 1.02
No. of reflections	3050
No. of parameters	325
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.32

Computer programs: SMART (Bruker, 2000-2001), SAINT (Bruker, 2000-2001), SAINT, SHELXTL (Bruker, 2000-2001), SHELXTL.

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