(R,R)-Ethyl­enebis[(2-methyl­phen­yl)­phenyl­phosphine oxide] (`o-Tolyl DiPAMPO')

King, G.; Bergin, E.; Müller-Bunz, H.; Gilheany, D.G.

doi:10.1107/S1600536807029479

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(R,R)-Ethylenebis[(2-methylphenyl)phenylphosphine oxide] (`o-Tolyl DiPAMPO')

G. King, E. Bergin, H. Müller-Bunz and D. G. Gilheany

In the course of studies on the synthesis of P-chiral phosphine ligands, a simple route to enantiopure DiPAMP analogues has been developed. The crystal structure of the title compound, C₂₈H₂₈O₂P₂, shows it to be the R,R enantiomer of the bisphosphine oxide, prior to reduction to the corresponding bisphosphine. This is believed to be the first example of a crystal structure of an enantiopure DiPAMPO-type compound.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029479/wk2065sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029479/wk2065Isup2.hkl Contains datablock I

CCDC reference: 655007

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.113
Data-to-parameter ratio = 23.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.717     0.989
            Tmin(prime) and Tmax expected:      0.896     0.989
            RR(prime) =      0.800
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.38
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C22

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               6693
           Count of symmetry unique reflns         3835
           Completeness (_total/calc)            174.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2858
           Fraction of Friedel pairs measured     0.745
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of P1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of P2     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

This crystal structure establishes that in our recently developed method for the construction of P-stereogenic phosphine oxides (Bergin et al., 2007), the use of (-)-menthol gives rise to the R-configured phosphine oxide.

The PO and PC bond lengths are both at the high ends of the ranges expected for phosphine oxides, (147.5–149) and (179–181) pm respectively (Gilheany, 1992). The bond angles at phosphorus (CPO 111–113.5° and CPC 106–106.5°) show the expected deviation from the tetrahedral values consistent with the shorter PO distance (Gilheany, 1992).

Related literature top

For related literature, see: Bergin et al. (2007); Gilheany (1992).

Experimental top

The title compound was synthesized by our recently developed method for the generation of P-stereogenic phosphorus compounds (Bergin et al., 2007). The corresponding monophosphine oxide was produced in good ee (80%) from the reaction of the racemic phosphine with (-)-menthol in the presence of hexachloroacetone. It was subsequently oxidatively coupled to yield the bisphosphine oxide in 98% ee. X-ray quality crystals were obtained by crystallizing from benzene. To the best of our knowledge this is the first crystal structure of an enantiomerically pure DiPAMPO analogue.

Structure description top

For related literature, see: Bergin et al. (2007); Gilheany (1992).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-hydrogen atoms.

(R,R)-Ethylenebis[(2-methylphenyl)phenylphosphine oxide] top

Crystal data top

C₂₈H₂₈O₂P₂	D_x = 1.324 Mg m⁻³
M_r = 458.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 5179 reflections
a = 5.7941 (5) Å	θ = 2.5–30.8°
b = 17.2455 (15) Å	µ = 0.21 mm⁻¹
c = 23.012 (2) Å	T = 100 K
V = 2299.4 (3) Å³	Lath, colourless
Z = 4	0.50 × 0.50 × 0.05 mm
F(000) = 968

Data collection top

Bruker APEX CCD area-detector diffractometer	6693 independent reflections
Radiation source: fine-focus sealed tube	5820 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
φ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.717, T_max = 0.989	k = −24→24
24918 measured reflections	l = −32→32

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
6693 reflections	Δρ_max = 0.56 e Å⁻³
289 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (8)

Crystal data top

C₂₈H₂₈O₂P₂	V = 2299.4 (3) Å³
M_r = 458.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.7941 (5) Å	µ = 0.21 mm⁻¹
b = 17.2455 (15) Å	T = 100 K
c = 23.012 (2) Å	0.50 × 0.50 × 0.05 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	6693 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5820 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.989	R_int = 0.054
24918 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.113	Δρ_max = 0.56 e Å⁻³
S = 1.09	Δρ_min = −0.23 e Å⁻³
6693 reflections	Absolute structure: Flack (1983)
289 parameters	Absolute structure parameter: −0.02 (8)
0 restraints

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

	x	y	z	U_iso*/U_eq
P1	0.33886 (9)	0.29398 (3)	0.21588 (2)	0.01480 (11)
O1	0.5851 (3)	0.29881 (9)	0.19807 (6)	0.0211 (3)
C1	0.2408 (4)	0.19598 (11)	0.22940 (9)	0.0171 (4)
C2	0.0501 (4)	0.16736 (13)	0.19982 (10)	0.0265 (5)
H2A	−0.0349	0.2006	0.1748	0.032*
C3	−0.0176 (5)	0.09058 (14)	0.20643 (12)	0.0350 (6)
H3A	−0.1479	0.0714	0.1859	0.042*
C4	0.1036 (4)	0.04265 (13)	0.24256 (11)	0.0318 (6)
H4A	0.0591	−0.0101	0.2465	0.038*
C5	0.2907 (5)	0.07055 (13)	0.27351 (10)	0.0308 (6)
H5A	0.3714	0.0369	0.2991	0.037*
C6	0.3631 (4)	0.14753 (12)	0.26775 (9)	0.0223 (4)
C7	0.5636 (5)	0.17576 (14)	0.30295 (11)	0.0333 (6)
H7A	0.6237	0.1331	0.3267	0.050*
H7B	0.5132	0.2181	0.3283	0.050*
H7C	0.6851	0.1945	0.2769	0.050*
C8	0.2867 (3)	0.34813 (11)	0.28190 (9)	0.0174 (4)
C9	0.4561 (4)	0.39914 (12)	0.30008 (10)	0.0251 (5)
H9A	0.5929	0.4052	0.2778	0.030*
C10	0.4266 (5)	0.44147 (14)	0.35085 (12)	0.0338 (6)
H10A	0.5431	0.4766	0.3631	0.041*
C11	0.2307 (5)	0.43278 (14)	0.38321 (11)	0.0315 (6)
H11A	0.2124	0.4612	0.4183	0.038*
C12	0.0594 (5)	0.38282 (13)	0.36513 (10)	0.0303 (5)
H12A	−0.0768	0.3772	0.3877	0.036*
C13	0.0843 (4)	0.34061 (13)	0.31418 (10)	0.0244 (5)
H13A	−0.0352	0.3069	0.3014	0.029*
C14	0.1437 (4)	0.33385 (12)	0.16196 (9)	0.0185 (4)
H14A	0.1397	0.2991	0.1277	0.022*
H14B	−0.0140	0.3362	0.1784	0.022*
C15	0.2170 (4)	0.41508 (11)	0.14268 (9)	0.0161 (4)
H15A	0.3778	0.4134	0.1282	0.019*
H15B	0.2120	0.4507	0.1764	0.019*
P2	0.02887 (8)	0.45118 (3)	0.08600 (2)	0.01335 (11)
O2	−0.2200 (2)	0.44574 (9)	0.10142 (6)	0.0188 (3)
C16	0.1036 (3)	0.39833 (11)	0.02016 (8)	0.0141 (4)
C17	0.2915 (3)	0.34797 (11)	0.01890 (9)	0.0169 (4)
H17A	0.3940	0.3461	0.0511	0.020*
C18	0.3312 (4)	0.30052 (12)	−0.02873 (9)	0.0209 (4)
H18A	0.4604	0.2666	−0.0291	0.025*
C19	0.1830 (4)	0.30256 (12)	−0.07545 (9)	0.0224 (4)
H19A	0.2045	0.2681	−0.1072	0.027*
C20	0.0026 (4)	0.35514 (12)	−0.07596 (9)	0.0204 (4)
H20A	−0.0940	0.3581	−0.1093	0.024*
C21	−0.0409 (3)	0.40357 (11)	−0.02912 (9)	0.0171 (4)
C22	−0.2408 (4)	0.45922 (12)	−0.03249 (9)	0.0212 (4)
H22A	−0.3182	0.4535	−0.0701	0.032*
H22B	−0.1839	0.5125	−0.0284	0.032*
H22C	−0.3503	0.4479	−0.0012	0.032*
C23	0.1147 (3)	0.55056 (11)	0.07362 (8)	0.0151 (4)
C24	0.3295 (4)	0.57026 (12)	0.05179 (10)	0.0236 (4)
H24A	0.4410	0.5310	0.0448	0.028*
C25	0.3826 (4)	0.64718 (13)	0.04011 (10)	0.0265 (5)
H25A	0.5286	0.6603	0.0241	0.032*
C26	0.2232 (4)	0.70479 (13)	0.05178 (10)	0.0253 (5)
H26A	0.2609	0.7574	0.0442	0.030*
C27	0.0107 (4)	0.68623 (12)	0.07428 (11)	0.0281 (5)
H27A	−0.0982	0.7260	0.0823	0.034*
C28	−0.0452 (4)	0.60876 (12)	0.08534 (10)	0.0225 (4)
H28A	−0.1923	0.5958	0.1008	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0144 (2)	0.0150 (2)	0.0149 (2)	−0.00059 (19)	−0.00002 (19)	0.0026 (2)
O1	0.0179 (7)	0.0223 (7)	0.0233 (7)	−0.0003 (6)	0.0016 (6)	0.0029 (6)
C1	0.0193 (9)	0.0163 (9)	0.0155 (9)	−0.0014 (8)	0.0032 (7)	−0.0003 (7)
C2	0.0242 (11)	0.0252 (11)	0.0302 (12)	−0.0040 (9)	−0.0034 (10)	−0.0015 (9)
C3	0.0314 (13)	0.0284 (12)	0.0452 (15)	−0.0101 (10)	0.0038 (12)	−0.0093 (11)
C4	0.0398 (14)	0.0168 (10)	0.0387 (13)	−0.0074 (10)	0.0160 (11)	−0.0048 (10)
C5	0.0485 (15)	0.0187 (10)	0.0253 (12)	0.0056 (10)	0.0111 (11)	0.0037 (9)
C6	0.0302 (12)	0.0193 (9)	0.0175 (9)	0.0037 (9)	0.0033 (9)	0.0000 (8)
C7	0.0459 (15)	0.0262 (11)	0.0279 (12)	0.0052 (11)	−0.0154 (11)	0.0025 (9)
C8	0.0189 (9)	0.0139 (8)	0.0194 (9)	0.0021 (7)	−0.0022 (8)	0.0031 (8)
C9	0.0210 (10)	0.0240 (10)	0.0302 (11)	−0.0036 (9)	−0.0033 (9)	−0.0046 (9)
C10	0.0341 (13)	0.0286 (12)	0.0386 (13)	0.0017 (10)	−0.0104 (11)	−0.0124 (11)
C11	0.0479 (15)	0.0266 (12)	0.0200 (11)	0.0101 (11)	−0.0042 (10)	−0.0051 (9)
C12	0.0393 (14)	0.0255 (11)	0.0261 (12)	0.0032 (11)	0.0099 (10)	0.0017 (9)
C13	0.0277 (12)	0.0181 (9)	0.0274 (11)	−0.0025 (8)	0.0056 (9)	−0.0001 (9)
C14	0.0206 (10)	0.0187 (9)	0.0161 (9)	−0.0008 (8)	−0.0015 (8)	0.0049 (7)
C15	0.0182 (10)	0.0147 (9)	0.0153 (9)	−0.0005 (7)	−0.0011 (7)	0.0016 (7)
P2	0.0129 (2)	0.0126 (2)	0.0145 (2)	0.00024 (18)	0.00076 (18)	0.00101 (18)
O2	0.0156 (7)	0.0192 (7)	0.0217 (7)	0.0000 (6)	0.0028 (5)	−0.0001 (6)
C16	0.0153 (9)	0.0119 (8)	0.0151 (9)	−0.0020 (7)	0.0023 (7)	0.0012 (7)
C17	0.0175 (9)	0.0155 (9)	0.0177 (9)	0.0004 (7)	0.0007 (7)	0.0018 (8)
C18	0.0192 (9)	0.0186 (9)	0.0250 (10)	0.0026 (8)	0.0057 (9)	−0.0016 (8)
C19	0.0261 (11)	0.0217 (10)	0.0192 (10)	−0.0036 (9)	0.0067 (8)	−0.0044 (8)
C20	0.0214 (10)	0.0245 (10)	0.0152 (9)	−0.0056 (8)	0.0004 (8)	−0.0005 (8)
C21	0.0151 (9)	0.0173 (8)	0.0188 (9)	−0.0019 (7)	0.0016 (8)	0.0024 (7)
C22	0.0187 (10)	0.0248 (10)	0.0202 (10)	0.0020 (8)	−0.0026 (8)	0.0033 (9)
C23	0.0190 (9)	0.0128 (8)	0.0133 (8)	−0.0011 (8)	−0.0022 (7)	0.0005 (7)
C24	0.0227 (10)	0.0186 (9)	0.0296 (11)	0.0007 (9)	0.0045 (9)	−0.0008 (8)
C25	0.0269 (12)	0.0216 (10)	0.0309 (12)	−0.0042 (9)	0.0025 (9)	0.0022 (9)
C26	0.0310 (12)	0.0143 (9)	0.0307 (11)	−0.0020 (9)	−0.0093 (9)	0.0051 (9)
C27	0.0281 (12)	0.0177 (9)	0.0384 (13)	0.0069 (9)	−0.0040 (10)	−0.0009 (9)
C28	0.0179 (9)	0.0198 (9)	0.0296 (11)	0.0026 (8)	0.0002 (9)	0.0002 (9)

Geometric parameters (Å, º) top

P1—O1	1.4870 (15)	C15—P2	1.810 (2)
P1—C8	1.809 (2)	C15—H15A	0.9900
P1—C1	1.810 (2)	C15—H15B	0.9900
P1—C14	1.814 (2)	P2—O2	1.4878 (14)
C1—C2	1.388 (3)	P2—C16	1.820 (2)
C1—C6	1.407 (3)	P2—C23	1.807 (2)
C2—C3	1.389 (3)	C16—C17	1.393 (3)
C2—H2A	0.9500	C16—C21	1.413 (3)
C3—C4	1.367 (4)	C17—C18	1.387 (3)
C3—H3A	0.9500	C17—H17A	0.9500
C4—C5	1.383 (4)	C18—C19	1.376 (3)
C4—H4A	0.9500	C18—H18A	0.9500
C5—C6	1.398 (3)	C19—C20	1.384 (3)
C5—H5A	0.9500	C19—H19A	0.9500
C6—C7	1.498 (3)	C20—C21	1.387 (3)
C7—H7A	0.9800	C20—H20A	0.9500
C7—H7B	0.9800	C21—C22	1.506 (3)
C7—H7C	0.9800	C22—H22A	0.9800
C8—C13	1.394 (3)	C22—H22B	0.9800
C8—C9	1.383 (3)	C22—H22C	0.9800
C9—C10	1.388 (3)	C23—C24	1.384 (3)
C9—H9A	0.9500	C23—C28	1.392 (3)
C10—C11	1.366 (4)	C24—C25	1.388 (3)
C10—H10A	0.9500	C24—H24A	0.9500
C11—C12	1.379 (4)	C25—C26	1.383 (3)
C11—H11A	0.9500	C25—H25A	0.9500
C12—C13	1.387 (3)	C26—C27	1.374 (3)
C12—H12A	0.9500	C26—H26A	0.9500
C13—H13A	0.9500	C27—C28	1.398 (3)
C14—C15	1.530 (3)	C27—H27A	0.9500
C14—H14A	0.9900	C28—H28A	0.9500
C14—H14B	0.9900

O1—P1—C8	111.28 (9)	C14—C15—P2	110.90 (13)
O1—P1—C1	113.64 (9)	C14—C15—H15A	109.5
C8—P1—C1	106.57 (9)	P2—C15—H15A	109.5
O1—P1—C14	112.86 (9)	C14—C15—H15B	109.5
C8—P1—C14	105.93 (9)	P2—C15—H15B	109.5
C1—P1—C14	106.01 (9)	H15A—C15—H15B	108.0
C2—C1—C6	119.8 (2)	O2—P2—C15	112.96 (9)
C2—C1—P1	119.83 (16)	O2—P2—C16	113.42 (9)
C6—C1—P1	120.29 (16)	C15—P2—C16	106.51 (9)
C1—C2—C3	120.7 (2)	O2—P2—C23	111.36 (9)
C1—C2—H2A	119.7	C15—P2—C23	105.90 (9)
C3—C2—H2A	119.7	C16—P2—C23	106.15 (9)
C4—C3—C2	119.9 (2)	C17—C16—C21	119.10 (18)
C4—C3—H3A	120.1	C17—C16—P2	121.03 (15)
C2—C3—H3A	120.1	C21—C16—P2	119.68 (14)
C3—C4—C5	120.4 (2)	C18—C17—C16	120.91 (19)
C3—C4—H4A	119.8	C18—C17—H17A	119.5
C5—C4—H4A	119.8	C16—C17—H17A	119.5
C4—C5—C6	121.1 (2)	C19—C18—C17	119.9 (2)
C4—C5—H5A	119.5	C19—C18—H18A	120.0
C6—C5—H5A	119.5	C17—C18—H18A	120.0
C5—C6—C1	118.2 (2)	C20—C19—C18	119.64 (19)
C5—C6—C7	119.3 (2)	C20—C19—H19A	120.2
C1—C6—C7	122.5 (2)	C18—C19—H19A	120.2
C6—C7—H7A	109.5	C19—C20—C21	121.68 (19)
C6—C7—H7B	109.5	C19—C20—H20A	119.2
H7A—C7—H7B	109.5	C21—C20—H20A	119.2
C6—C7—H7C	109.5	C20—C21—C16	118.55 (18)
H7A—C7—H7C	109.5	C20—C21—C22	118.90 (18)
H7B—C7—H7C	109.5	C16—C21—C22	122.55 (18)
C13—C8—C9	119.7 (2)	C21—C22—H22A	109.5
C13—C8—P1	122.69 (16)	C21—C22—H22B	109.5
C9—C8—P1	117.64 (16)	H22A—C22—H22B	109.5
C8—C9—C10	120.1 (2)	C21—C22—H22C	109.5
C8—C9—H9A	119.9	H22A—C22—H22C	109.5
C10—C9—H9A	119.9	H22B—C22—H22C	109.5
C11—C10—C9	120.2 (2)	C24—C23—C28	119.46 (18)
C11—C10—H10A	119.9	C24—C23—P2	122.50 (15)
C9—C10—H10A	119.9	C28—C23—P2	118.02 (15)
C10—C11—C12	120.2 (2)	C23—C24—C25	120.3 (2)
C10—C11—H11A	119.9	C23—C24—H24A	119.9
C12—C11—H11A	119.9	C25—C24—H24A	119.9
C11—C12—C13	120.5 (2)	C26—C25—C24	120.1 (2)
C11—C12—H12A	119.7	C26—C25—H25A	120.0
C13—C12—H12A	119.7	C24—C25—H25A	120.0
C8—C13—C12	119.3 (2)	C25—C26—C27	120.3 (2)
C8—C13—H13A	120.4	C25—C26—H26A	119.8
C12—C13—H13A	120.4	C27—C26—H26A	119.8
C15—C14—P1	111.86 (14)	C26—C27—C28	119.9 (2)
C15—C14—H14A	109.2	C26—C27—H27A	120.0
P1—C14—H14A	109.2	C28—C27—H27A	120.0
C15—C14—H14B	109.2	C23—C28—C27	120.0 (2)
P1—C14—H14B	109.2	C23—C28—H28A	120.0
H14A—C14—H14B	107.9	C27—C28—H28A	120.0

O1—P1—C1—C2	−124.41 (18)	C14—C15—P2—O2	51.52 (16)
C8—P1—C1—C2	112.66 (18)	C14—C15—P2—C16	−73.63 (15)
C14—P1—C1—C2	0.1 (2)	C14—C15—P2—C23	173.66 (14)
O1—P1—C1—C6	52.70 (19)	O2—P2—C16—C17	−131.23 (16)
C8—P1—C1—C6	−70.23 (19)	C15—P2—C16—C17	−6.35 (18)
C14—P1—C1—C6	177.22 (17)	C23—P2—C16—C17	106.19 (16)
C6—C1—C2—C3	−1.8 (3)	O2—P2—C16—C21	43.77 (17)
P1—C1—C2—C3	175.28 (19)	C15—P2—C16—C21	168.64 (15)
C1—C2—C3—C4	0.3 (4)	C23—P2—C16—C21	−78.82 (16)
C2—C3—C4—C5	1.3 (4)	C21—C16—C17—C18	−3.2 (3)
C3—C4—C5—C6	−1.3 (4)	P2—C16—C17—C18	171.82 (15)
C4—C5—C6—C1	−0.2 (3)	C16—C17—C18—C19	−0.3 (3)
C4—C5—C6—C7	178.8 (2)	C17—C18—C19—C20	3.6 (3)
C2—C1—C6—C5	1.8 (3)	C18—C19—C20—C21	−3.3 (3)
P1—C1—C6—C5	−175.33 (16)	C19—C20—C21—C16	−0.2 (3)
C2—C1—C6—C7	−177.2 (2)	C19—C20—C21—C22	−179.76 (19)
P1—C1—C6—C7	5.7 (3)	C17—C16—C21—C20	3.4 (3)
O1—P1—C8—C13	−166.69 (16)	P2—C16—C21—C20	−171.66 (15)
C1—P1—C8—C13	−42.30 (19)	C17—C16—C21—C22	−177.02 (18)
C14—P1—C8—C13	70.29 (19)	P2—C16—C21—C22	7.9 (3)
O1—P1—C8—C9	13.8 (2)	O2—P2—C23—C24	−171.85 (16)
C1—P1—C8—C9	138.15 (17)	C15—P2—C23—C24	65.00 (19)
C14—P1—C8—C9	−109.26 (18)	C16—P2—C23—C24	−47.96 (19)
C13—C8—C9—C10	1.3 (3)	O2—P2—C23—C28	6.53 (18)
P1—C8—C9—C10	−179.16 (18)	C15—P2—C23—C28	−116.62 (17)
C8—C9—C10—C11	0.2 (4)	C16—P2—C23—C28	130.42 (16)
C9—C10—C11—C12	−1.0 (4)	C28—C23—C24—C25	−1.8 (3)
C10—C11—C12—C13	0.3 (4)	P2—C23—C24—C25	176.51 (18)
C9—C8—C13—C12	−2.0 (3)	C23—C24—C25—C26	1.8 (4)
P1—C8—C13—C12	178.48 (17)	C24—C25—C26—C27	−0.8 (4)
C11—C12—C13—C8	1.2 (3)	C25—C26—C27—C28	−0.1 (4)
O1—P1—C14—C15	−50.63 (17)	C24—C23—C28—C27	0.9 (3)
C8—P1—C14—C15	71.38 (16)	P2—C23—C28—C27	−177.55 (17)
C1—P1—C14—C15	−175.64 (14)	C26—C27—C28—C23	0.1 (3)
P1—C14—C15—P2	176.78 (11)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈O₂P₂
M_r	458.44
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.7941 (5), 17.2455 (15), 23.012 (2)
V (Å³)	2299.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.50 × 0.50 × 0.05

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.717, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	24918, 6693, 5820
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.113, 1.09
No. of reflections	6693
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.23
Absolute structure	Flack (1983)
Absolute structure parameter	−0.02 (8)

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

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