(S)-2,2′-Bis­[bis(3,5-di­methyl­phenyl)­phosphinoyl]-5,5′,6,6′,7,7′,8,8′-octa­hydro-1,1′-bi­naphthyl

Guo, R.; Wu, J.; Kowk, W.; Chen, J.; Choi, M.C.K.; Zhou, Z.

doi:10.1107/S1600536802001010

(S)-2,2'-Bis[bis(3,5-dimethylphenyl)phosphinoyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl

R. Guo, J. Wu, W. Kowk, J. Chen, M. C. K. Choi and Z. Zhou

The title compound, C₅₂H₅₆O₂P₂, was synthesized conveniently from (S)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl and bis(3,5-dimethylphenyl)phosphine chloride in high yield. The molecule has crystallographic twofold rotation symmetry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001010/ob6106sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001010/ob6106Isup2.hkl Contains datablock I

CCDC reference: 182616

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.128
Data-to-parameter ratio = 20.3

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No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.55
         From the CIF: _reflns_number_total               5134
         Count of symmetry unique reflns         2918
         Completeness (_total/calc)            175.94%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2216
         Fraction of Friedel pairs measured     0.759
         Are heavy atom types Z>Si present          yes
          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.

Comment top

The phosphinite ligands exhibit good to excellent enantioselectivity and high reactivity in the hydrogenation of prochiral olefines (Zhang et al., 1998; Chan et al., 1997). The phosphinite (I) can be conveniently obtained by reacting (S)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (H8-BINOL) with bis(3,5-dimethylphenyl)phosphine chloride. Recent research shows that the phosphinite ligands derived from bis(3,5-dimethylphenyl)phosphine chloride exhibit higher enantioselectivity in the catalytic hydrogenation reaction than that derived from chlorodiphenylphosphine, due to the steric and electronic modulation of the substitute groups on the P atom (Trabesinger et al., 1997; RajanBabu et al., 1997). As part of our efforts investigating this phenomenon, we present the crystal structure of (I).

As shown in Fig. 1, the title molecule has crystallographic twofold rotation symmetry. The lengths of the Csp³—Csp³ bonds C7—C8, C8—C9 and C9—C10 [1.476 (3), 1.441 (3) and 1.463 (3) Å, respectively] are shorter than the normal Csp³—Csp³ bond (1.51–1.55 Å) and differ significantly from the Csp³—Csp² bonds C3—-C7 and C4–C10 [1.513 (4) and 1.510 (4) Å, respectively] in the H8-naphthyl unit. The disorder is persumed to be due to the puckering of the ring, which is suggested by the high U_eq values of the C8 and C9 atoms.

Experimental top

All reactions were carried out under N₂ using Schlenk techniques. (S)-2,2'-Dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (0.30 g, 1.0 mmol) and 4-N,N-dimethylaminopyridine (15 mg) were added in a 50 ml round-bottomed Schlenk flask with a stir bar. The atmosphere was replaced with N₂ several times, and 0.8 ml dry Et₃N and 30 ml dry Et₂O were added. The mixture cooled to 273 K with ice-bath, followed by dropping in bis(3,5-dimethylphenyl)phosphine chloride (0.6 ml, 2.5 mmol) within 20 min. The solvent was removed under vacuum after stirring at room temperature for another 3 h. The residues were dissolved in 15 ml toluene and purified with flash silica-gel column (30 ml toluene as eluent). Toluene was removed and 670 mg white solid obtained (yield: 87%). Colorless crystals suitable for X-ray diffraction were obtained by recrystallization of a solution in Et₂O/CH₂Cl₂ (5:1). ³¹P NMR (CDCl₃): δ 109.7. ¹³C NMR (CDCl₃): δ 21.39, 21.48, 23.22, 23.30, 27.80, 29.76, 115.28, 115.41, 127.36, 127.54, 127.65, 127.84, 129.09, 130.85, 131.01, 131.33, 137.03, 137.59, 142.11, 142.26. ¹H NMR (500 MHz, CDCl₃): δ 1.52–1.68 (m, 8H), 2.21 (s, 12H), 2.19 (s, 12H), 2.14–2.23 (m, 2H), 2.38–2.42 (m, 2H), 2.60–2.64 (m, 2H), 2.69–2.75 (m, 2H).

Computing details top

Data collection: SMART (Bruker, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Bruker, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Figures top

Fig. 1. The molecular structure of (I) showing ellipsoids at the 30% probability level.

2,2'-Bis[bis(3,5-dimethylphenyl)phosphinoyl]-5,5',6,6',7,7',8,8'-Octahydro -1,1'-Binaphthyl top

Crystal data top

C₅₂H₅₆O₂P₂	D_x = 1.159 Mg m⁻³
M_r = 774.91	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2	Cell parameters from 5442 reflections
a = 13.1983 (18) Å	θ = 1–27.5°
b = 19.015 (3) Å	µ = 0.14 mm⁻¹
c = 8.8486 (12) Å	T = 294 K
V = 2220.7 (5) Å³	Block, colorless
Z = 2	0.34 × 0.28 × 0.26 mm
F(000) = 828

Data collection top

Bruker CCD area-detector diffractometer	5134 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −17→11
T_min = 0.955, T_max = 0.965	k = −24→24
15328 measured reflections	l = −11→11

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0656P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
5134 reflections	Δρ_max = 0.27 e Å⁻³
253 parameters	Δρ_min = −0.28 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 2216 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (12)

Crystal data top

C₅₂H₅₆O₂P₂	V = 2220.7 (5) Å³
M_r = 774.91	Z = 2
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 13.1983 (18) Å	µ = 0.14 mm⁻¹
b = 19.015 (3) Å	T = 294 K
c = 8.8486 (12) Å	0.34 × 0.28 × 0.26 mm

Data collection top

Bruker CCD area-detector diffractometer	5134 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	3079 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.965	R_int = 0.045
15328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.128	Δρ_max = 0.27 e Å⁻³
S = 0.93	Δρ_min = −0.28 e Å⁻³
5134 reflections	Absolute structure: Flack (1983), 2216 Friedel pairs
253 parameters	Absolute structure parameter: −0.03 (12)
3 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. The crystal structure of the compound was determined by the direct method (or Patterson function) which yielded the positions of part of non-hydrogen atoms and subsequent difference Fourier syntheses were employed to locate all of the remaining non-hydrogen atoms which did not show up in the initial structure. Hydrogen atoms were located basing on Difference Fourier Syntheses connecting geometrical analysis. All of non-hydrogen atoms were refined anisotropically. All of hydrogen atoms were refined with fixed individual displacement parameters. All experiment and computation were performed on a Bruker CCD Area Detector Diffractomrter and PC computer with program of Bruker Smart and Bruker SHELXTL packages. 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	0.25399 (5)	0.04515 (3)	0.63295 (8)	0.04504 (19)
O1	0.37731 (12)	0.03915 (9)	0.6105 (2)	0.0479 (5)
C1	0.44142 (18)	0.07676 (13)	0.7069 (3)	0.0388 (6)
C2	0.50291 (17)	0.03932 (12)	0.8033 (3)	0.0357 (6)
C3	0.57059 (17)	0.07564 (13)	0.8971 (3)	0.0395 (6)
C4	0.57599 (19)	0.14848 (13)	0.8897 (3)	0.0452 (7)
C5	0.5118 (2)	0.18387 (14)	0.7915 (4)	0.0551 (8)
H5A	0.5142	0.2327	0.7880	0.066*
C6	0.4453 (2)	0.14923 (14)	0.7000 (4)	0.0551 (8)
H6A	0.4034	0.1740	0.6343	0.066*
C7	0.6382 (2)	0.03482 (14)	1.0038 (3)	0.0531 (8)
H7A	0.5972	0.0008	1.0580	0.064*
H7B	0.6877	0.0090	0.9449	0.064*
C8	0.6920 (3)	0.07922 (18)	1.1146 (5)	0.0989 (14)
H8A	0.6475	0.0870	1.2002	0.119*
H8B	0.7504	0.0533	1.1511	0.119*
C9	0.7263 (3)	0.14666 (16)	1.0607 (5)	0.1041 (15)
H9A	0.7535	0.1728	1.1456	0.125*
H9B	0.7812	0.1391	0.9897	0.125*
C10	0.6488 (2)	0.18970 (14)	0.9872 (4)	0.0638 (9)
H10A	0.6820	0.2248	0.9250	0.077*
H10B	0.6105	0.2143	1.0644	0.077*
C11	0.22009 (19)	−0.04828 (14)	0.6221 (3)	0.0469 (6)
C12	0.2805 (2)	−0.09767 (14)	0.5532 (3)	0.0517 (7)
H12A	0.3411	−0.0839	0.5087	0.062*
C13	0.2518 (3)	−0.16836 (14)	0.5493 (3)	0.0603 (8)
C14	0.1611 (3)	−0.18645 (16)	0.6172 (4)	0.0699 (10)
H14A	0.1411	−0.2333	0.6151	0.084*
C15	0.0987 (2)	−0.13820 (18)	0.6881 (4)	0.0643 (9)
C16	0.1307 (2)	−0.06902 (16)	0.6912 (3)	0.0565 (8)
H16A	0.0913	−0.0356	0.7408	0.068*
C17	0.3180 (3)	−0.22299 (16)	0.4754 (5)	0.0879 (12)
H17A	0.2862	−0.2682	0.4833	0.132*
H17B	0.3826	−0.2242	0.5251	0.132*
H17C	0.3273	−0.2113	0.3708	0.132*
C18	0.0027 (3)	−0.1618 (2)	0.7629 (5)	0.1041 (14)
H18A	−0.0060	−0.2114	0.7477	0.156*
H18B	−0.0537	−0.1370	0.7199	0.156*
H18C	0.0064	−0.1521	0.8693	0.156*
C19	0.21828 (19)	0.07338 (12)	0.4439 (3)	0.0438 (7)
C20	0.1160 (2)	0.07499 (14)	0.4076 (3)	0.0532 (8)
H20A	0.0688	0.0594	0.4782	0.064*
C21	0.0828 (2)	0.09904 (15)	0.2698 (4)	0.0612 (9)
C22	0.1542 (2)	0.12326 (14)	0.1666 (4)	0.0613 (9)
H22A	0.1326	0.1392	0.0726	0.074*
C23	0.2572 (2)	0.12426 (13)	0.2001 (3)	0.0537 (7)
C24	0.2871 (2)	0.09915 (13)	0.3400 (3)	0.0471 (7)
H24A	0.3556	0.0996	0.3648	0.057*
C25	−0.0300 (2)	0.1007 (2)	0.2327 (5)	0.0970 (14)
H25A	−0.0677	0.0819	0.3162	0.146*
H25B	−0.0426	0.0728	0.1442	0.146*
H25C	−0.0507	0.1483	0.2145	0.146*
C26	0.3327 (3)	0.15355 (16)	0.0901 (4)	0.0719 (10)
H26A	0.3997	0.1495	0.1316	0.108*
H26B	0.3177	0.2022	0.0712	0.108*
H26C	0.3291	0.1277	−0.0030	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0420 (4)	0.0433 (3)	0.0498 (4)	0.0021 (4)	−0.0049 (4)	0.0002 (3)
O1	0.0413 (9)	0.0471 (10)	0.0554 (12)	0.0041 (9)	−0.0095 (9)	−0.0049 (10)
C1	0.0364 (13)	0.0346 (13)	0.0454 (16)	−0.0021 (11)	−0.0025 (12)	−0.0012 (12)
C2	0.0340 (13)	0.0309 (12)	0.0423 (14)	−0.0009 (11)	0.0028 (11)	−0.0006 (11)
C3	0.0340 (13)	0.0385 (13)	0.0461 (16)	−0.0026 (11)	0.0027 (12)	−0.0028 (12)
C4	0.0400 (14)	0.0371 (14)	0.0586 (18)	−0.0027 (12)	0.0067 (14)	−0.0063 (14)
C5	0.0606 (19)	0.0305 (14)	0.074 (2)	−0.0027 (14)	−0.0019 (17)	−0.0033 (14)
C6	0.0556 (18)	0.0422 (16)	0.068 (2)	0.0070 (14)	−0.0066 (16)	0.0076 (15)
C7	0.0494 (17)	0.0507 (16)	0.059 (2)	−0.0009 (14)	−0.0105 (15)	−0.0018 (14)
C8	0.110 (3)	0.084 (2)	0.103 (3)	−0.023 (2)	−0.062 (3)	0.007 (2)
C9	0.093 (3)	0.073 (2)	0.146 (4)	−0.002 (2)	−0.059 (3)	−0.036 (3)
C10	0.059 (2)	0.0508 (17)	0.082 (3)	−0.0116 (16)	−0.0077 (18)	−0.0160 (17)
C11	0.0459 (14)	0.0498 (14)	0.0448 (15)	−0.0048 (13)	−0.0101 (12)	0.0092 (15)
C12	0.0565 (19)	0.0470 (16)	0.0516 (17)	−0.0060 (14)	−0.0030 (14)	0.0024 (14)
C13	0.077 (2)	0.0453 (15)	0.0583 (18)	−0.0033 (18)	−0.018 (2)	0.0002 (14)
C14	0.086 (3)	0.0542 (19)	0.069 (2)	−0.0280 (19)	−0.016 (2)	0.0134 (18)
C15	0.062 (2)	0.065 (2)	0.065 (2)	−0.0183 (18)	−0.0073 (17)	0.0180 (17)
C16	0.0520 (17)	0.0593 (18)	0.058 (2)	−0.0034 (15)	−0.0019 (15)	0.0111 (15)
C17	0.120 (3)	0.0550 (19)	0.089 (3)	0.002 (2)	−0.009 (3)	−0.0100 (19)
C18	0.085 (3)	0.104 (3)	0.123 (4)	−0.036 (2)	0.022 (3)	0.015 (3)
C19	0.0417 (15)	0.0309 (12)	0.0589 (17)	0.0006 (11)	−0.0051 (13)	0.0025 (13)
C20	0.0444 (16)	0.0483 (15)	0.067 (2)	−0.0081 (13)	−0.0099 (14)	0.0153 (15)
C21	0.0536 (18)	0.0512 (17)	0.079 (2)	−0.0046 (15)	−0.0190 (17)	0.0127 (17)
C22	0.072 (2)	0.0481 (17)	0.063 (2)	−0.0026 (15)	−0.0194 (18)	0.0115 (15)
C23	0.065 (2)	0.0373 (14)	0.0584 (18)	0.0095 (15)	0.0057 (17)	0.0019 (12)
C24	0.0421 (14)	0.0422 (14)	0.0570 (19)	0.0055 (12)	0.0009 (13)	−0.0004 (14)
C25	0.062 (2)	0.107 (3)	0.123 (4)	−0.022 (2)	−0.043 (2)	0.040 (3)
C26	0.083 (2)	0.0602 (19)	0.072 (2)	0.0107 (18)	0.015 (2)	0.0082 (17)

Geometric parameters (Å, º) top

P1—O1	1.6437 (18)	C13—C14	1.383 (5)
P1—C19	1.819 (3)	C13—C17	1.506 (5)
P1—C11	1.834 (3)	C14—C15	1.384 (5)
O1—C1	1.398 (3)	C14—H14A	0.9300
C1—C2	1.376 (3)	C15—C16	1.382 (4)
C1—C6	1.380 (4)	C15—C18	1.498 (5)
C2—C3	1.402 (3)	C16—H16A	0.9300
C2—C2ⁱ	1.497 (4)	C17—H17A	0.9600
C3—C4	1.389 (3)	C17—H17B	0.9600
C3—C7	1.513 (4)	C17—H17C	0.9600
C4—C5	1.387 (4)	C18—H18A	0.9600
C4—C10	1.510 (4)	C18—H18B	0.9600
C5—C6	1.364 (4)	C18—H18C	0.9600
C5—H5A	0.9300	C19—C24	1.382 (4)
C6—H6A	0.9300	C19—C20	1.388 (4)
C7—C8	1.476 (3)	C20—C21	1.374 (4)
C7—H7A	0.9700	C20—H20A	0.9300
C7—H7B	0.9700	C21—C22	1.391 (5)
C8—C9	1.441 (3)	C21—C25	1.524 (4)
C8—H8A	0.9700	C22—C23	1.391 (4)
C8—H8B	0.9700	C22—H22A	0.9300
C9—C10	1.463 (3)	C23—C24	1.384 (4)
C9—H9A	0.9700	C23—C26	1.500 (4)
C9—H9B	0.9700	C24—H24A	0.9300
C10—H10A	0.9700	C25—H25A	0.9600
C10—H10B	0.9700	C25—H25B	0.9600
C11—C12	1.374 (4)	C25—H25C	0.9600
C11—C16	1.387 (4)	C26—H26A	0.9600
C12—C13	1.397 (4)	C26—H26B	0.9600
C12—H12A	0.9300	C26—H26C	0.9600

O1—P1—C19	99.55 (11)	C14—C13—C17	121.2 (3)
O1—P1—C11	99.67 (11)	C12—C13—C17	121.2 (3)
C19—P1—C11	100.04 (12)	C15—C14—C13	123.2 (3)
C1—O1—P1	119.36 (16)	C15—C14—H14A	118.4
C2—C1—C6	121.5 (2)	C13—C14—H14A	118.4
C2—C1—O1	118.1 (2)	C16—C15—C14	117.3 (3)
C6—C1—O1	120.4 (2)	C16—C15—C18	122.3 (4)
C1—C2—C3	119.2 (2)	C14—C15—C18	120.4 (3)
C1—C2—C2ⁱ	119.1 (2)	C15—C16—C11	121.5 (3)
C3—C2—C2ⁱ	121.6 (2)	C15—C16—H16A	119.3
C4—C3—C2	119.7 (2)	C11—C16—H16A	119.3
C4—C3—C7	120.7 (2)	C13—C17—H17A	109.5
C2—C3—C7	119.5 (2)	C13—C17—H17B	109.5
C5—C4—C3	118.8 (2)	H17A—C17—H17B	109.5
C5—C4—C10	119.6 (2)	C13—C17—H17C	109.5
C3—C4—C10	121.6 (3)	H17A—C17—H17C	109.5
C6—C5—C4	122.0 (2)	H17B—C17—H17C	109.5
C6—C5—H5A	119.0	C15—C18—H18A	109.5
C4—C5—H5A	119.0	C15—C18—H18B	109.5
C5—C6—C1	118.7 (3)	H18A—C18—H18B	109.5
C5—C6—H6A	120.7	C15—C18—H18C	109.5
C1—C6—H6A	120.7	H18A—C18—H18C	109.5
C8—C7—C3	113.9 (2)	H18B—C18—H18C	109.5
C8—C7—H7A	108.8	C24—C19—C20	118.5 (3)
C3—C7—H7A	108.8	C24—C19—P1	123.1 (2)
C8—C7—H7B	108.8	C20—C19—P1	118.1 (2)
C3—C7—H7B	108.8	C21—C20—C19	121.5 (3)
H7A—C7—H7B	107.7	C21—C20—H20A	119.2
C9—C8—C7	116.1 (3)	C19—C20—H20A	119.2
C9—C8—H8A	108.3	C20—C21—C22	118.5 (3)
C7—C8—H8A	108.3	C20—C21—C25	120.6 (3)
C9—C8—H8B	108.3	C22—C21—C25	120.9 (3)
C7—C8—H8B	108.3	C21—C22—C23	121.8 (3)
H8A—C8—H8B	107.4	C21—C22—H22A	119.1
C10—C9—C8	115.2 (3)	C23—C22—H22A	119.1
C10—C9—H9A	108.5	C24—C23—C22	117.7 (3)
C8—C9—H9A	108.5	C24—C23—C26	121.3 (3)
C10—C9—H9B	108.5	C22—C23—C26	121.0 (3)
C8—C9—H9B	108.5	C19—C24—C23	122.0 (3)
H9A—C9—H9B	107.5	C19—C24—H24A	119.0
C9—C10—C4	114.1 (2)	C23—C24—H24A	119.0
C9—C10—H10A	108.7	C21—C25—H25A	109.5
C4—C10—H10A	108.7	C21—C25—H25B	109.5
C9—C10—H10B	108.7	H25A—C25—H25B	109.5
C4—C10—H10B	108.7	C21—C25—H25C	109.5
H10A—C10—H10B	107.6	H25A—C25—H25C	109.5
C12—C11—C16	119.7 (3)	H25B—C25—H25C	109.5
C12—C11—P1	122.9 (2)	C23—C26—H26A	109.5
C16—C11—P1	117.4 (2)	C23—C26—H26B	109.5
C11—C12—C13	120.8 (3)	H26A—C26—H26B	109.5
C11—C12—H12A	119.6	C23—C26—H26C	109.5
C13—C12—H12A	119.6	H26A—C26—H26C	109.5
C14—C13—C12	117.6 (3)	H26B—C26—H26C	109.5

C19—P1—O1—C1	124.38 (19)	O1—P1—C11—C16	155.9 (2)
C11—P1—O1—C1	−133.61 (19)	C19—P1—C11—C16	−102.5 (2)
P1—O1—C1—C2	114.1 (2)	C16—C11—C12—C13	1.3 (4)
P1—O1—C1—C6	−68.5 (3)	P1—C11—C12—C13	179.3 (2)
C6—C1—C2—C3	0.4 (4)	C11—C12—C13—C14	−0.1 (4)
O1—C1—C2—C3	177.7 (2)	C11—C12—C13—C17	−179.4 (3)
C6—C1—C2—C2ⁱ	−178.6 (2)	C12—C13—C14—C15	−0.2 (5)
O1—C1—C2—C2ⁱ	−1.3 (3)	C17—C13—C14—C15	179.1 (3)
C1—C2—C3—C4	−1.2 (4)	C13—C14—C15—C16	−0.7 (5)
C2ⁱ—C2—C3—C4	177.8 (2)	C13—C14—C15—C18	−178.3 (3)
C1—C2—C3—C7	179.8 (2)	C14—C15—C16—C11	2.0 (5)
C2ⁱ—C2—C3—C7	−1.3 (3)	C18—C15—C16—C11	179.6 (3)
C2—C3—C4—C5	1.7 (4)	C12—C11—C16—C15	−2.3 (4)
C7—C3—C4—C5	−179.3 (3)	P1—C11—C16—C15	179.6 (2)
C2—C3—C4—C10	−179.2 (3)	O1—P1—C19—C24	−15.2 (2)
C7—C3—C4—C10	−0.1 (4)	C11—P1—C19—C24	−116.9 (2)
C3—C4—C5—C6	−1.4 (4)	O1—P1—C19—C20	170.8 (2)
C10—C4—C5—C6	179.4 (3)	C11—P1—C19—C20	69.1 (2)
C4—C5—C6—C1	0.6 (4)	C24—C19—C20—C21	2.4 (4)
C2—C1—C6—C5	−0.1 (4)	P1—C19—C20—C21	176.7 (2)
O1—C1—C6—C5	−177.4 (2)	C19—C20—C21—C22	−1.1 (5)
C4—C3—C7—C8	11.3 (4)	C19—C20—C21—C25	−179.7 (3)
C2—C3—C7—C8	−169.6 (3)	C20—C21—C22—C23	−0.6 (5)
C3—C7—C8—C9	−36.9 (5)	C25—C21—C22—C23	178.0 (3)
C7—C8—C9—C10	52.0 (6)	C21—C22—C23—C24	1.0 (4)
C8—C9—C10—C4	−38.5 (5)	C21—C22—C23—C26	−177.2 (3)
C5—C4—C10—C9	−167.6 (3)	C20—C19—C24—C23	−2.0 (4)
C3—C4—C10—C9	13.3 (5)	P1—C19—C24—C23	−176.03 (19)
O1—P1—C11—C12	−22.1 (3)	C22—C23—C24—C19	0.4 (4)
C19—P1—C11—C12	79.5 (2)	C26—C23—C24—C19	178.6 (3)

Symmetry code: (i) −x+1, −y, z.

Experimental details

Crystal data
Chemical formula	C₅₂H₅₆O₂P₂
M_r	774.91
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	294
a, b, c (Å)	13.1983 (18), 19.015 (3), 8.8486 (12)
V (Å³)	2220.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.34 × 0.28 × 0.26

Data collection
Diffractometer	Bruker CCD area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	15328, 5134, 3079
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.128, 0.93
No. of reflections	5134
No. of parameters	253
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28
Absolute structure	Flack (1983), 2216 Friedel pairs
Absolute structure parameter	−0.03 (12)

Computer programs: SMART (Bruker, 1995), SMART, SHELXTL-NT (Bruker, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-NT.

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(S)-2,2'-Bis­[bis(3,5-di­methyl­phenyl)­phosphinoyl]-5,5',6,6',7,7',8,8'-octa­hydro-1,1'-bi­naphthyl

Supporting information

Key indicators

checkCIF results

(S)-2,2'-Bis[bis(3,5-dimethylphenyl)phosphinoyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl