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In the title compound, C39H32O2P2·0.5C7H8, there are two distinct phosphorus centers. The P-C bond lengths around the di­phenyl­phosphino group are around 0.04 Å larger than those in the phosphine oxide moiety. This corresponds to smaller C-P-C bond angles of 101.2 (15)° compared to 108.4 (9)° for the latter. The rigid dibenzo­pyran backbone is folded at an angle of 158.9 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020419/na6032sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020419/na6032Isup2.hkl
Contains datablock I

CCDC reference: 155904

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • H-atom completeness 99%
  • Disorder in solvent or counterion
  • R factor = 0.058
  • wR factor = 0.168
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry
Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent disorder ....................... 12.00 Perc. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C42.5 H36 O2 P2 Atom count from the _atom_site data: C42.5 H35.5 O2 P2 CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C42.50 H36 O2 P2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 85.00 85.00 0.00 H 72.00 71.00 1.00 O 4.00 4.00 0.00 P 4.00 4.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title structure, (I), is similar to the bis(diphenylphosphino) derivative, (II) (Hillebrand et al., 1995; Kranenburg et al., 1995), and the bis(methylphenylphosphine) oxide compound (Hamada et al., 1997). The atoms in the xanthane backbone of (I) do not have the symmetry associated with (II), but are folded at a similar angle, 158.9 (1)° [cf. 156.6° in (II)], due to the steric congestion between the diphenylphosphine groups and the xanthane unit.

The geometry around each P atom is distinct due to the different oxidation states: the P—C bond distances [mean 1.802 (11) Å] around P1, formally PV, are shorter than those at P2 [PIII; mean 1.843 (6) Å]. The C—P1—C bond angles tend towards tetrahedral [average 108.4 (9)°] whilst the corresponding ones around P2 are more acute [average 101.2 (15)°].

The lone pair and oxide group on the P atoms in (I) have an in–out orientation, whereas in (II), the lone pairs point towards each other (in–in), so that only a small adjustment is required for metal chelation (Kranenburg et al., 1995). This can be correlated with the distance between the P atoms which increases from 4.045 (1) Å in (II) to 4.693 (2) Å in (I).

The asymmetry of the ligand is also shown by the C—C—P angles at the substituted C atoms of the xanthane unit, namely C2 and C8. In (I), the angle deformation is again dependent on the nature of the phosphine; thus, those around C2 are 113.4 (2) and 129.2 (2)° (for P1), whilst around C8 are 120.9 (2) and 121.6 (2)° (for P2). In the (more) symmetric ligand (II), the C—C—P angles are 118.4 (2) and 125.1 (3)°, i.e. the reverse situation is present.

Experimental top

The title compound was obtained as a by-product in the attempted synthesis of (xantphos)nickel dicyanide. Colorless crystals were obtained by recrystallization from toluene of a solution containing styrene and cyclooctadiene.

Refinement top

Aromatic H atoms were constrained and allowed to ride on their C atoms with Uiso(H) = 1.2Ueq(C). The methyl H atoms were constrained to an ideal geometry with Uiso(H) = 1.5Ueq(C), and allowed to rotate freely about the C—C bonds. The toluene solvent was located near an inversion centre, so the methyl group was disordered over two sites, and refined with a site-occupancy factor of 50%. The H atom, at the same position as the disordered methyl group, was not refined.

Computing details top

Data collection: Locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: PLATON (Spek, 2000).

Figures top
[Figure 1] Fig. 1. PLATON/ORTEP representation (Spek, 2000) of (I) with displacement ellipsoids at 50% probability level. H atoms have been omitted for clarity.
(I) top
Crystal data top
C39H32O2P2·0.5C7H8Z = 2
Mr = 640.15F(000) = 673
Triclinic, P1Dx = 1.288 Mg m3
a = 10.7700 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1547 (11) ÅCell parameters from 25 reflections
c = 15.941 (3) Åθ = 9.9–13.9°
α = 91.088 (11)°µ = 0.17 mm1
β = 102.471 (11)°T = 150 K
γ = 116.993 (7)°Wedge, colorless
V = 1651.1 (4) Å30.40 × 0.28 × 0.18 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.053
Radiation source: rotating anodeθmax = 25.1°, θmin = 1.3°
Graphite monochromatorh = 1211
ω scansk = 013
6185 measured reflectionsl = 1818
5855 independent reflections3 standard reflections every 60 min
4099 reflections with I > 2σ(I)' intensity decay: <1%
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0952P)2 + 0.4293P]
where P = (Fo2 + 2Fc2)/3
5855 reflections(Δ/σ)max < 0.001
427 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C39H32O2P2·0.5C7H8γ = 116.993 (7)°
Mr = 640.15V = 1651.1 (4) Å3
Triclinic, P1Z = 2
a = 10.7700 (11) ÅMo Kα radiation
b = 11.1547 (11) ŵ = 0.17 mm1
c = 15.941 (3) ÅT = 150 K
α = 91.088 (11)°0.40 × 0.28 × 0.18 mm
β = 102.471 (11)°
Data collection top
Nonius CAD4
diffractometer
Rint = 0.053
6185 measured reflections3 standard reflections every 60 min
5855 independent reflections intensity decay: <1%
4099 reflections with I > 2σ(I)'
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 1.01Δρmax = 0.51 e Å3
5855 reflectionsΔρmin = 0.46 e Å3
427 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.20793 (9)0.94189 (8)0.29904 (5)0.0212 (2)
P20.30943 (9)0.70846 (9)0.09805 (5)0.0236 (2)
O10.4584 (2)0.8873 (2)0.26752 (14)0.0228 (5)
O20.1413 (2)1.0221 (2)0.32667 (15)0.0280 (5)
C10.5061 (3)0.9973 (3)0.3310 (2)0.0200 (7)
C20.3998 (3)1.0270 (3)0.3475 (2)0.0202 (7)
C30.4443 (4)1.1379 (3)0.4095 (2)0.0267 (7)
H30.37451.16070.42180.032*
C40.5864 (4)1.2151 (3)0.4531 (2)0.0315 (8)
H40.61491.29130.49430.038*
C50.6874 (4)1.1800 (3)0.4361 (2)0.0258 (7)
H50.78521.23160.46750.031*
C60.6498 (3)1.0712 (3)0.3742 (2)0.0222 (7)
C70.5597 (3)0.8773 (3)0.2304 (2)0.0209 (7)
C80.5045 (3)0.7940 (3)0.1504 (2)0.0213 (7)
C90.6025 (3)0.7806 (3)0.1116 (2)0.0249 (7)
H90.56850.72450.05770.030*
C100.7480 (4)0.8478 (3)0.1505 (2)0.0284 (8)
H100.81360.83880.12270.034*
C110.7993 (3)0.9284 (3)0.2298 (2)0.0246 (7)
H110.89980.97300.25630.030*
C120.7058 (3)0.9452 (3)0.2715 (2)0.0202 (7)
C130.1818 (3)0.9226 (3)0.1839 (2)0.0229 (7)
C140.2784 (4)1.0227 (3)0.1462 (2)0.0299 (8)
H140.36551.09310.18180.036*
C150.2483 (4)1.0203 (4)0.0572 (2)0.0350 (9)
H150.31431.08940.03180.042*
C160.1231 (4)0.9180 (4)0.0053 (2)0.0337 (8)
H160.10270.91680.05580.040*
C170.0266 (4)0.8166 (4)0.0419 (2)0.0308 (8)
H170.06010.74620.00600.037*
C180.0571 (3)0.8184 (3)0.1308 (2)0.0255 (7)
H180.00780.74770.15580.031*
C190.1290 (3)0.7746 (3)0.3319 (2)0.0236 (7)
C200.1798 (4)0.6817 (3)0.3275 (2)0.0283 (8)
H200.26090.70360.30460.034*
C210.1139 (4)0.5572 (3)0.3560 (2)0.0353 (9)
H210.15070.49460.35390.042*
C220.0056 (4)0.5239 (4)0.3876 (2)0.0384 (9)
H220.05130.43820.40700.046*
C230.0586 (4)0.6143 (4)0.3910 (2)0.0422 (10)
H230.14090.59070.41290.051*
C240.0068 (4)0.7398 (4)0.3629 (2)0.0336 (8)
H240.03120.80160.36470.040*
C250.3134 (3)0.6801 (3)0.0154 (2)0.0235 (7)
C260.3458 (4)0.7916 (4)0.0607 (2)0.0325 (8)
H260.36770.87670.03180.039*
C270.3466 (4)0.7801 (4)0.1466 (3)0.0420 (10)
H270.37110.85790.17600.050*
C280.3123 (4)0.6576 (4)0.1906 (2)0.0445 (10)
H280.31120.65010.25020.053*
C290.2795 (5)0.5460 (4)0.1471 (3)0.0498 (11)
H290.25710.46110.17660.060*
C300.2789 (4)0.5569 (4)0.0599 (2)0.0379 (9)
H300.25450.47900.03070.045*
C310.2556 (4)0.5393 (3)0.1322 (2)0.0269 (8)
C320.3418 (5)0.4774 (4)0.1485 (3)0.0473 (11)
H320.43600.52160.13970.057*
C330.2937 (5)0.3521 (4)0.1773 (3)0.0566 (12)
H330.35600.31220.18940.068*
C340.1571 (5)0.2844 (4)0.1887 (2)0.0475 (11)
H340.12440.19800.20840.057*
C350.0690 (5)0.3426 (4)0.1713 (2)0.0449 (11)
H350.02600.29620.17870.054*
C360.1165 (4)0.4691 (4)0.1428 (2)0.0368 (9)
H360.05340.50810.13050.044*
C430.9075 (4)1.1511 (4)0.3689 (3)0.0451 (11)
H43A0.97661.12010.36120.068*
H43B0.94061.20330.42660.068*
H43C0.89961.20870.32460.068*
C440.7747 (5)0.9380 (4)0.4297 (2)0.0411 (10)
H44A0.84700.91070.42280.062*
H44B0.68170.85690.42290.062*
H44C0.80460.98870.48750.062*
C450.7605 (3)1.0285 (3)0.3603 (2)0.0235 (7)
C460.4044 (5)0.4421 (4)0.4208 (3)0.0476 (11)
H460.33670.40200.36630.057*
C470.3631 (5)0.3993 (4)0.4959 (3)0.0476 (11)
H470.26860.32880.49180.057*
C480.5430 (5)0.5428 (4)0.4235 (3)0.0461 (10)
C490.5890 (10)0.5856 (8)0.3400 (6)0.050 (2)0.50
H49A0.69100.65330.35440.075*0.50
H49B0.53090.62490.30830.075*0.50
H49C0.57460.50610.30380.075*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0211 (4)0.0230 (4)0.0223 (4)0.0118 (4)0.0073 (3)0.0009 (3)
P20.0225 (5)0.0237 (4)0.0243 (5)0.0105 (4)0.0062 (4)0.0010 (3)
O10.0190 (11)0.0203 (11)0.0270 (12)0.0065 (9)0.0086 (9)0.0054 (9)
O20.0279 (13)0.0322 (13)0.0292 (13)0.0187 (11)0.0074 (10)0.0024 (10)
C10.0247 (17)0.0153 (15)0.0196 (16)0.0081 (13)0.0077 (13)0.0028 (12)
C20.0214 (16)0.0188 (15)0.0201 (16)0.0087 (13)0.0063 (13)0.0011 (13)
C30.0273 (18)0.0277 (18)0.0265 (18)0.0142 (15)0.0071 (15)0.0020 (14)
C40.034 (2)0.0241 (18)0.033 (2)0.0122 (16)0.0054 (16)0.0096 (15)
C50.0232 (17)0.0241 (17)0.0222 (17)0.0064 (14)0.0018 (14)0.0019 (14)
C60.0250 (17)0.0226 (17)0.0205 (16)0.0110 (14)0.0088 (13)0.0054 (13)
C70.0233 (17)0.0186 (15)0.0255 (17)0.0110 (14)0.0124 (14)0.0063 (13)
C80.0204 (16)0.0209 (16)0.0239 (17)0.0107 (14)0.0053 (13)0.0048 (13)
C90.0275 (18)0.0288 (18)0.0215 (17)0.0155 (15)0.0074 (14)0.0008 (14)
C100.0284 (18)0.0355 (19)0.0307 (19)0.0194 (16)0.0152 (15)0.0067 (15)
C110.0215 (17)0.0286 (18)0.0255 (18)0.0127 (15)0.0070 (14)0.0064 (14)
C120.0228 (17)0.0175 (15)0.0219 (16)0.0096 (13)0.0084 (13)0.0047 (13)
C130.0245 (17)0.0243 (17)0.0262 (17)0.0149 (14)0.0106 (14)0.0023 (14)
C140.0314 (19)0.0242 (18)0.0306 (19)0.0097 (15)0.0087 (15)0.0016 (15)
C150.040 (2)0.0292 (19)0.033 (2)0.0116 (17)0.0139 (17)0.0097 (16)
C160.042 (2)0.035 (2)0.0240 (18)0.0185 (18)0.0092 (16)0.0028 (15)
C170.0282 (19)0.036 (2)0.0266 (19)0.0149 (16)0.0060 (15)0.0007 (15)
C180.0216 (17)0.0294 (18)0.0272 (18)0.0122 (15)0.0086 (14)0.0019 (14)
C190.0247 (17)0.0269 (17)0.0164 (16)0.0112 (14)0.0022 (13)0.0001 (13)
C200.0310 (19)0.0258 (18)0.0273 (18)0.0114 (15)0.0101 (15)0.0020 (14)
C210.047 (2)0.0246 (18)0.032 (2)0.0140 (17)0.0107 (17)0.0043 (15)
C220.048 (2)0.0232 (18)0.0280 (19)0.0030 (17)0.0105 (17)0.0010 (15)
C230.034 (2)0.042 (2)0.040 (2)0.0051 (18)0.0197 (18)0.0017 (18)
C240.031 (2)0.032 (2)0.035 (2)0.0109 (16)0.0132 (16)0.0028 (16)
C250.0185 (16)0.0279 (18)0.0217 (17)0.0104 (14)0.0018 (13)0.0003 (14)
C260.036 (2)0.0316 (19)0.036 (2)0.0198 (17)0.0100 (17)0.0068 (16)
C270.038 (2)0.050 (2)0.041 (2)0.021 (2)0.0131 (18)0.020 (2)
C280.037 (2)0.061 (3)0.024 (2)0.013 (2)0.0093 (17)0.0047 (19)
C290.056 (3)0.042 (2)0.036 (2)0.008 (2)0.017 (2)0.0120 (19)
C300.046 (2)0.0247 (19)0.032 (2)0.0054 (17)0.0158 (18)0.0021 (15)
C310.0288 (18)0.0269 (18)0.0214 (17)0.0107 (15)0.0050 (14)0.0002 (14)
C320.042 (2)0.031 (2)0.073 (3)0.0167 (19)0.022 (2)0.023 (2)
C330.053 (3)0.034 (2)0.078 (3)0.019 (2)0.010 (2)0.020 (2)
C340.061 (3)0.030 (2)0.031 (2)0.006 (2)0.007 (2)0.0081 (17)
C350.047 (2)0.034 (2)0.032 (2)0.0021 (19)0.0176 (19)0.0023 (17)
C360.036 (2)0.031 (2)0.035 (2)0.0069 (17)0.0147 (17)0.0052 (16)
C430.0217 (19)0.043 (2)0.054 (3)0.0007 (17)0.0130 (18)0.0219 (19)
C440.058 (3)0.059 (3)0.0228 (19)0.043 (2)0.0051 (18)0.0027 (18)
C450.0184 (16)0.0251 (17)0.0233 (17)0.0082 (14)0.0033 (13)0.0023 (13)
C460.066 (3)0.049 (3)0.036 (2)0.041 (2)0.000 (2)0.0012 (19)
C470.057 (3)0.041 (2)0.052 (3)0.030 (2)0.009 (2)0.003 (2)
C480.063 (3)0.041 (2)0.049 (3)0.037 (2)0.013 (2)0.007 (2)
C490.055 (5)0.036 (5)0.054 (5)0.019 (4)0.008 (4)0.002 (4)
Geometric parameters (Å, º) top
P1—O21.488 (2)C22—C231.371 (6)
P1—C21.809 (3)C22—H220.9500
P1—C131.790 (3)C23—C241.386 (5)
P1—C191.808 (3)C23—H230.9500
P2—C81.848 (3)C24—H240.9500
P2—C251.844 (3)C25—C301.383 (5)
P2—C311.837 (3)C25—C261.392 (5)
O1—C71.392 (4)C26—C271.376 (5)
O1—C11.396 (4)C26—H260.9500
C1—C61.382 (4)C27—C281.373 (6)
C1—C21.400 (4)C27—H270.9500
C2—C31.396 (4)C28—C291.377 (6)
C3—C41.374 (5)C28—H280.9500
C3—H30.9500C29—C301.395 (5)
C4—C51.386 (5)C29—H290.9500
C4—H40.9500C30—H300.9500
C5—C61.395 (4)C31—C321.375 (5)
C5—H50.9500C31—C361.392 (5)
C6—C451.524 (4)C32—C331.380 (5)
C7—C121.390 (4)C32—H320.9500
C7—C81.403 (4)C33—C341.371 (6)
C8—C91.393 (4)C33—H330.9500
C9—C101.378 (5)C34—C351.360 (6)
C9—H90.9500C34—H340.9500
C10—C111.384 (5)C35—C361.388 (5)
C10—H100.9500C35—H350.9500
C11—C121.395 (4)C36—H360.9500
C11—H110.9500C43—C451.526 (5)
C12—C451.519 (4)C43—H43A0.9800
C13—C181.387 (5)C43—H43B0.9800
C13—C141.389 (4)C43—H43C0.9800
C14—C151.383 (5)C44—C451.542 (5)
C14—H140.9500C44—H44A0.9800
C15—C161.374 (5)C44—H44B0.9800
C15—H150.9500C44—H44C0.9800
C16—C171.385 (5)C46—C471.384 (6)
C16—H160.9500C46—C481.393 (6)
C17—C181.382 (5)C46—H460.9500
C17—H170.9500C47—C48i1.380 (6)
C18—H180.9500C47—H470.9500
C19—C201.382 (5)C48—C47i1.380 (6)
C19—C241.397 (5)C48—C491.530 (9)
C20—C211.381 (5)C49—H49A0.9800
C20—H200.9500C49—H49B0.9800
C21—C221.379 (5)C49—H49C0.9800
C21—H210.9500
O2—P1—C2110.04 (14)C22—C23—C24120.7 (4)
O2—P1—C13111.59 (14)C22—C23—H23119.6
O2—P1—C19110.03 (14)C24—C23—H23119.6
C13—P1—C2107.61 (14)C23—C24—C19119.4 (3)
C19—P1—C2109.31 (15)C23—C24—H24120.3
C13—P1—C19108.21 (15)C19—C24—H24120.3
C25—P2—C899.94 (14)C30—C25—C26118.1 (3)
C31—P2—C8100.80 (15)C30—C25—P2125.6 (3)
C31—P2—C25102.83 (15)C26—C25—P2116.2 (3)
C7—O1—C1118.0 (2)C27—C26—C25120.9 (3)
C6—C1—O1121.3 (3)C27—C26—H26119.6
C6—C1—C2122.8 (3)C25—C26—H26119.6
O1—C1—C2115.9 (3)C28—C27—C26120.9 (4)
C3—C2—C1117.4 (3)C28—C27—H27119.6
C1—C2—P1129.2 (2)C26—C27—H27119.6
C3—C2—P1113.4 (2)C27—C28—C29119.2 (4)
C4—C3—C2121.7 (3)C27—C28—H28120.4
C4—C3—H3119.2C29—C28—H28120.4
C2—C3—H3119.2C28—C29—C30120.3 (4)
C3—C4—C5119.0 (3)C28—C29—H29119.9
C3—C4—H4120.5C30—C29—H29119.9
C5—C4—H4120.5C25—C30—C29120.7 (4)
C4—C5—C6122.0 (3)C25—C30—H30119.6
C4—C5—H5119.0C29—C30—H30119.6
C6—C5—H5119.0C32—C31—C36117.7 (3)
C1—C6—C5117.2 (3)C32—C31—P2125.3 (3)
C1—C6—C45121.3 (3)C36—C31—P2117.0 (3)
C5—C6—C45121.3 (3)C31—C32—C33121.1 (4)
C12—C7—O1121.3 (3)C31—C32—H32119.4
C12—C7—C8122.9 (3)C33—C32—H32119.4
O1—C7—C8115.8 (3)C34—C33—C32120.7 (4)
C9—C8—C7117.5 (3)C34—C33—H33119.6
C7—C8—P2120.9 (2)C32—C33—H33119.6
C9—C8—P2121.6 (2)C35—C34—C33119.1 (4)
C10—C9—C8120.9 (3)C35—C34—H34120.5
C10—C9—H9119.6C33—C34—H34120.5
C8—C9—H9119.6C34—C35—C36120.7 (4)
C9—C10—C11120.4 (3)C34—C35—H35119.6
C9—C10—H10119.8C36—C35—H35119.6
C11—C10—H10119.8C35—C36—C31120.6 (4)
C10—C11—C12121.0 (3)C35—C36—H36119.7
C10—C11—H11119.5C31—C36—H36119.7
C12—C11—H11119.5C45—C43—H43A109.5
C7—C12—C11117.4 (3)C45—C43—H43B109.5
C7—C12—C45121.2 (3)H43A—C43—H43B109.5
C11—C12—C45121.3 (3)C45—C43—H43C109.5
C18—C13—C14119.1 (3)H43A—C43—H43C109.5
C18—C13—P1120.9 (2)H43B—C43—H43C109.5
C14—C13—P1119.5 (3)C45—C44—H44A109.5
C15—C14—C13120.3 (3)C45—C44—H44B109.5
C15—C14—H14119.9H44A—C44—H44B109.5
C13—C14—H14119.9C45—C44—H44C109.5
C16—C15—C14120.1 (3)H44A—C44—H44C109.5
C16—C15—H15119.9H44B—C44—H44C109.5
C14—C15—H15119.9C12—C45—C6108.9 (3)
C15—C16—C17120.3 (3)C12—C45—C43110.9 (3)
C15—C16—H16119.9C6—C45—C43111.6 (3)
C17—C16—H16119.9C12—C45—C44108.5 (3)
C18—C17—C16119.6 (3)C6—C45—C44108.0 (3)
C18—C17—H17120.2C43—C45—C44109.0 (3)
C16—C17—H17120.2C47—C46—C48121.4 (4)
C17—C18—C13120.6 (3)C47—C46—H46119.3
C17—C18—H18119.7C48—C46—H46119.3
C13—C18—H18119.7C48i—C47—C46121.1 (4)
C20—C19—C24119.3 (3)C48i—C47—H47119.4
C20—C19—P1124.9 (3)C46—C47—H47119.4
C24—C19—P1115.8 (3)C47i—C48—C46117.4 (4)
C21—C20—C19120.6 (3)C47i—C48—C49121.6 (5)
C21—C20—H20119.7C46—C48—C49120.9 (5)
C19—C20—H20119.7C48—C49—H49A109.5
C22—C21—C20119.9 (4)C48—C49—H49B109.5
C22—C21—H21120.1H49A—C49—H49B109.5
C20—C21—H21120.1C48—C49—H49C109.5
C23—C22—C21120.1 (3)H49A—C49—H49C109.5
C23—C22—H22120.0H49B—C49—H49C109.5
C21—C22—H22120.0
C7—O1—C1—C618.6 (4)P1—C13—C18—C17169.4 (3)
C7—O1—C1—C2161.4 (3)O2—P1—C19—C20170.4 (3)
C6—C1—C2—C31.1 (5)C13—P1—C19—C2067.5 (3)
O1—C1—C2—C3178.8 (3)C2—P1—C19—C2049.4 (3)
C6—C1—C2—P1179.3 (2)O2—P1—C19—C2410.3 (3)
O1—C1—C2—P10.7 (4)C13—P1—C19—C24111.8 (3)
O2—P1—C2—C38.5 (3)C2—P1—C19—C24131.3 (3)
C13—P1—C2—C3130.3 (2)C24—C19—C20—C212.2 (5)
C19—P1—C2—C3112.4 (2)P1—C19—C20—C21178.6 (3)
O2—P1—C2—C1171.1 (3)C19—C20—C21—C221.3 (5)
C13—P1—C2—C149.3 (3)C20—C21—C22—C230.3 (6)
C19—P1—C2—C168.0 (3)C21—C22—C23—C240.0 (6)
C1—C2—C3—C40.3 (5)C22—C23—C24—C190.8 (6)
P1—C2—C3—C4179.9 (3)C20—C19—C24—C231.9 (5)
C2—C3—C4—C51.2 (5)P1—C19—C24—C23178.8 (3)
C3—C4—C5—C61.9 (5)C31—P2—C25—C301.5 (3)
O1—C1—C6—C5179.5 (3)C8—P2—C25—C30105.1 (3)
C2—C1—C6—C50.4 (5)C31—P2—C25—C26177.4 (3)
O1—C1—C6—C455.5 (4)C8—P2—C25—C2679.0 (3)
C2—C1—C6—C45174.6 (3)C30—C25—C26—C271.4 (5)
C4—C5—C6—C11.1 (5)P2—C25—C26—C27177.7 (3)
C4—C5—C6—C45176.1 (3)C25—C26—C27—C281.5 (6)
C1—O1—C7—C1220.0 (4)C26—C27—C28—C291.2 (6)
C1—O1—C7—C8160.5 (3)C27—C28—C29—C301.0 (6)
C12—C7—C8—C90.1 (5)C26—C25—C30—C291.2 (6)
O1—C7—C8—C9179.5 (3)P2—C25—C30—C29177.1 (3)
C12—C7—C8—P2178.9 (2)C28—C29—C30—C251.1 (6)
O1—C7—C8—P21.6 (4)C25—P2—C31—C3272.7 (4)
C31—P2—C8—C983.9 (3)C8—P2—C31—C3230.2 (4)
C25—P2—C8—C921.3 (3)C25—P2—C31—C36107.7 (3)
C31—P2—C8—C797.3 (3)C8—P2—C31—C36149.4 (3)
C25—P2—C8—C7157.5 (3)C36—C31—C32—C332.2 (6)
C7—C8—C9—C100.5 (5)P2—C31—C32—C33177.3 (3)
P2—C8—C9—C10178.3 (2)C31—C32—C33—C341.5 (7)
C8—C9—C10—C111.0 (5)C32—C33—C34—C350.2 (7)
C9—C10—C11—C121.0 (5)C33—C34—C35—C360.3 (6)
O1—C7—C12—C11179.5 (3)C34—C35—C36—C310.5 (6)
C8—C7—C12—C110.1 (4)C32—C31—C36—C351.8 (5)
O1—C7—C12—C452.6 (4)P2—C31—C36—C35177.8 (3)
C8—C7—C12—C45176.8 (3)C7—C12—C45—C623.6 (4)
C10—C11—C12—C70.4 (5)C11—C12—C45—C6159.7 (3)
C10—C11—C12—C45177.3 (3)C7—C12—C45—C43146.6 (3)
O2—P1—C13—C1885.5 (3)C11—C12—C45—C4336.6 (4)
C19—P1—C13—C1835.7 (3)C7—C12—C45—C4493.7 (3)
C2—P1—C13—C18153.7 (3)C11—C12—C45—C4483.1 (4)
O2—P1—C13—C1486.1 (3)C1—C6—C45—C1225.0 (4)
C19—P1—C13—C14152.7 (3)C5—C6—C45—C12160.2 (3)
C2—P1—C13—C1434.7 (3)C1—C6—C45—C43147.7 (3)
C18—C13—C14—C151.9 (5)C5—C6—C45—C4337.6 (4)
P1—C13—C14—C15170.0 (3)C1—C6—C45—C4492.6 (4)
C13—C14—C15—C160.6 (6)C5—C6—C45—C4482.2 (4)
C14—C15—C16—C170.2 (6)C48—C46—C47—C48i1.6 (7)
C15—C16—C17—C180.3 (5)C47—C46—C48—C47i1.6 (6)
C16—C17—C18—C131.6 (5)C47—C46—C48—C49177.7 (5)
C14—C13—C18—C172.3 (5)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC39H32O2P2·0.5C7H8
Mr640.15
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)10.7700 (11), 11.1547 (11), 15.941 (3)
α, β, γ (°)91.088 (11), 102.471 (11), 116.993 (7)
V3)1651.1 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.40 × 0.28 × 0.18
Data collection
DiffractometerNonius CAD4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)'] reflections
6185, 5855, 4099
Rint0.053
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.168, 1.01
No. of reflections5855
No. of parameters427
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.46

Computer programs: Locally modified CAD-4 Software (Enraf-Nonius, 1989), SET4 (de Boer & Duisenberg, 1984), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2000).

Selected geometric parameters (Å, º) top
P1—O21.488 (2)P2—C81.848 (3)
P1—C21.809 (3)P2—C251.844 (3)
P1—C131.790 (3)P2—C311.837 (3)
P1—C191.808 (3)
O2—P1—C2110.04 (14)C31—P2—C8100.80 (15)
O2—P1—C13111.59 (14)C31—P2—C25102.83 (15)
O2—P1—C19110.03 (14)C1—C2—P1129.2 (2)
C13—P1—C2107.61 (14)C3—C2—P1113.4 (2)
C19—P1—C2109.31 (15)C7—C8—P2120.9 (2)
C13—P1—C19108.21 (15)C9—C8—P2121.6 (2)
C25—P2—C899.94 (14)
 

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