(S)-(−)-2,2′-Bis­(di­phenyl­phosphino)-1,1′-bi­naphthyl, a versatile chelating ligand

Jones, M.D.; Almeida Paz, F.A.; Davies, J.E.; Johnson, B.F.G.

doi:10.1107/S1600536803006019

(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, a versatile chelating ligand

M. D. Jones, F. A. Almeida Paz, J. E. Davies and B. F. G. Johnson

The crystal structure of the title compound, [(S)-(-)-BINAP] or C₄₄H₃₂P₂, is enantiomorphous to the previously reported (R)-(+)-BINAP [Deeming et al. (1997). Organometallics, 16, 6004-6009], with effectively no differences in the molecular geometry apart from being of opposite absolute configuration.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006019/cf6247sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006019/cf6247Isup2.hkl Contains datablock I

CCDC reference: 209977

checkCIF report

Key indicators

Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.004 Å
R factor = 0.042
wR factor = 0.088
Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.06
         From the CIF: _reflns_number_total               5303
         Count of symmetry unique reflns         3045
         Completeness (_total/calc)            174.15%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2258
         Fraction of Friedel pairs measured     0.742
         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 ability to selectively form one enantiomer in preference to the other (asymmetric catalysis) is undoubtedly one of the major advances in modern drug design and synthesis. In 2000, the total worldwide sales of single-enantiomer compounds was 123 billion US dollars (Stinson, 2001). In recognition of the outstanding contributions to this field, Noyori received the Nobel Prize for Chemistry in 2001, with much of his work being centred around the different chiral forms of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (Noyori, 2002). BINAP is a conformationally flexible atropisometric diphosphine, which is able to coordinate to several transition metal centres, such as rhodium (Ikariya et al., 1985), ruthenium (Touriumi et al., 1982) and palladium (Ozawa et al., 1992). Once BINAP is coordinated, the high steric hindrance around the metal centre affords complexes which are extremely potent for asymmetric hydrogenation (Noyori, 2002). An example of this is the synthesis of (-)-menthol, in which a [Rh-(S)-BINAP] derivative is utilized to induce chirality in the final product. A search in the Cambridge Structural Database (Allen, 2002) reveals that only the (R)-(+)-BINAP crystal structure has been reported so far (Deeming et al., 1997). We report here the structure of the S enantiomer of this renowned organic ligand.

[(S)-(-)-BINAP], (I), crystallizes in the monoclinic space group P2₁, with one molecule in the asymmetric unit, as depicted in Fig. 1. Individual molecules of (S)-(-)-BINAP are spatially arranged in close packing along the a direction (Figs. 2 and 3). The structures of the R and S enantiomers are essentially the same, except for being of opposite absolute configuration (Deeming et al., 1997).

Experimental top

(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl was purchased from Aldrich (99.99% purity). Crystals suitable for X-Ray diffraction analysis were obtained by recrystallization from methanol.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), showing the labelling scheme for all non-H atoms. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres.
	Fig. 2. Crystal packing of two (filled and hollow bonds) molecules of (I).
	Fig. 3. Perspective view of the crystal structure of (I) along the c direction.

(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl top

Crystal data top

C₄₄H₃₂P₂	F(000) = 652
M_r = 622.64	D_x = 1.244 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6595 reflections
a = 9.1206 (2) Å	θ = 1.0–25.0°
b = 18.7541 (7) Å	µ = 0.16 mm⁻¹
c = 9.9829 (3) Å	T = 180 K
β = 103.206 (2)°	Block, white
V = 1662.40 (9) Å³	0.23 × 0.21 × 0.16 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	4457 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Thin–slice ω and ϕ scans	θ_max = 25.1°, θ_min = 3.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −10→10
T_min = 0.934, T_max = 0.981	k = −22→20
11117 measured reflections	l = −11→11
5303 independent reflections

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0313P)² + 0.2494P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5303 reflections	Δρ_max = 0.22 e Å⁻³
415 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (8)

Crystal data top

C₄₄H₃₂P₂	V = 1662.40 (9) Å³
M_r = 622.64	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.1206 (2) Å	µ = 0.16 mm⁻¹
b = 18.7541 (7) Å	T = 180 K
c = 9.9829 (3) Å	0.23 × 0.21 × 0.16 mm
β = 103.206 (2)°

Data collection top

Nonius KappaCCD diffractometer	5303 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	4457 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.981	R_int = 0.043
11117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.22 e Å⁻³
S = 1.04	Δρ_min = −0.28 e Å⁻³
5303 reflections	Absolute structure: Flack (1983)
415 parameters	Absolute structure parameter: −0.04 (8)
1 restraint

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	0.09925 (8)	0.82894 (4)	0.86920 (7)	0.02977 (19)
P2	0.04783 (8)	0.66685 (4)	0.57059 (7)	0.02816 (18)
C1	0.2926 (3)	0.80354 (16)	0.9502 (3)	0.0302 (7)
C2	0.3464 (3)	0.73532 (18)	0.9371 (3)	0.0394 (8)
H2	0.2785	0.6988	0.8965	0.047*
C3	0.4990 (4)	0.7200 (2)	0.9829 (3)	0.0493 (9)
H3	0.5342	0.6728	0.9748	0.059*
C4	0.5995 (4)	0.7728 (2)	1.0399 (3)	0.0500 (10)
H4	0.7035	0.7621	1.0716	0.060*
C5	0.5478 (3)	0.8408 (2)	1.0505 (3)	0.0467 (9)
H5	0.6165	0.8776	1.0883	0.056*
C6	0.3958 (3)	0.85620 (18)	1.0064 (3)	0.0375 (7)
H6	0.3615	0.9035	1.0146	0.045*
C7	0.0489 (3)	0.88919 (17)	0.9967 (3)	0.0339 (7)
C8	0.1054 (4)	0.88449 (18)	1.1389 (3)	0.0437 (8)
H8	0.1738	0.8475	1.1758	0.052*
C9	0.0621 (5)	0.9335 (2)	1.2266 (4)	0.0578 (10)
H9	0.1021	0.9306	1.3230	0.069*
C10	−0.0393 (5)	0.9866 (2)	1.1729 (5)	0.0663 (11)
H10	−0.0686	1.0203	1.2328	0.080*
C11	−0.0982 (4)	0.9911 (2)	1.0334 (4)	0.0596 (10)
H11	−0.1698	1.0270	0.9974	0.071*
C12	−0.0526 (4)	0.94328 (18)	0.9465 (3)	0.0462 (9)
H12	−0.0914	0.9474	0.8500	0.055*
C13	−0.0104 (3)	0.74883 (15)	0.8877 (2)	0.0245 (6)
C14	0.0144 (3)	0.70897 (16)	1.0124 (3)	0.0295 (7)
H14	0.0908	0.7237	1.0890	0.035*
C15	−0.0696 (3)	0.64987 (16)	1.0237 (3)	0.0309 (7)
H15	−0.0494	0.6234	1.1071	0.037*
C16	−0.1864 (3)	0.62773 (15)	0.9125 (3)	0.0281 (6)
C17	−0.2770 (3)	0.56749 (16)	0.9217 (3)	0.0349 (7)
H17	−0.2548	0.5389	1.0024	0.042*
C18	−0.3952 (4)	0.54979 (17)	0.8171 (3)	0.0408 (8)
H18	−0.4550	0.5092	0.8252	0.049*
C19	−0.4287 (3)	0.59126 (17)	0.6976 (3)	0.0388 (8)
H19	−0.5134	0.5795	0.6260	0.047*
C20	−0.3412 (3)	0.64844 (16)	0.6825 (3)	0.0324 (7)
H20	−0.3643	0.6754	0.5998	0.039*
C21	−0.2164 (3)	0.66799 (16)	0.7890 (2)	0.0239 (6)
C22	−0.1223 (3)	0.72804 (14)	0.7773 (2)	0.0229 (6)
C23	−0.1477 (3)	0.76698 (14)	0.6422 (2)	0.0233 (6)
C24	−0.2449 (3)	0.82725 (16)	0.6205 (2)	0.0249 (6)
C25	−0.3236 (3)	0.85056 (16)	0.7199 (3)	0.0351 (7)
H25	−0.3155	0.8240	0.8023	0.042*
C26	−0.4107 (4)	0.91046 (18)	0.6992 (3)	0.0446 (8)
H26	−0.4608	0.9255	0.7679	0.054*
C27	−0.4271 (4)	0.94995 (19)	0.5781 (3)	0.0474 (9)
H27	−0.4883	0.9915	0.5648	0.057*
C28	−0.3554 (3)	0.92892 (17)	0.4792 (3)	0.0388 (8)
H28	−0.3672	0.9561	0.3971	0.047*
C29	−0.2636 (3)	0.86739 (15)	0.4965 (3)	0.0277 (6)
C30	−0.1878 (3)	0.84407 (16)	0.3957 (3)	0.0306 (7)
H30	−0.1994	0.8700	0.3122	0.037*
C31	−0.0985 (3)	0.78511 (17)	0.4164 (3)	0.0294 (7)
H31	−0.0499	0.7703	0.3465	0.035*
C32	−0.0766 (3)	0.74545 (15)	0.5399 (2)	0.0253 (6)
C33	−0.0651 (3)	0.60013 (16)	0.4583 (3)	0.0297 (7)
C34	−0.2049 (3)	0.61220 (17)	0.3717 (3)	0.0347 (7)
H34	−0.2477	0.6586	0.3653	0.042*
C35	−0.2830 (3)	0.55655 (19)	0.2939 (3)	0.0425 (8)
H35	−0.3793	0.5652	0.2357	0.051*
C36	−0.2214 (4)	0.4891 (2)	0.3008 (3)	0.0441 (8)
H36	−0.2744	0.4517	0.2463	0.053*
C37	−0.0839 (4)	0.47624 (19)	0.3862 (3)	0.0444 (8)
H37	−0.0418	0.4297	0.3919	0.053*
C38	−0.0060 (4)	0.53105 (18)	0.4645 (3)	0.0373 (8)
H38	0.0894	0.5216	0.5235	0.045*
C39	0.1880 (3)	0.69237 (17)	0.4727 (3)	0.0325 (7)
C40	0.2258 (3)	0.64990 (19)	0.3711 (3)	0.0402 (8)
H40	0.1746	0.6061	0.3459	0.048*
C41	0.3385 (4)	0.6715 (2)	0.3066 (3)	0.0521 (9)
H41	0.3642	0.6421	0.2379	0.062*
C42	0.4127 (4)	0.7349 (2)	0.3413 (3)	0.0572 (11)
H42	0.4882	0.7497	0.2957	0.069*
C43	0.3772 (4)	0.7771 (2)	0.4427 (4)	0.0544 (10)
H43	0.4285	0.8209	0.4674	0.065*
C44	0.2663 (3)	0.75509 (19)	0.5083 (3)	0.0437 (8)
H44	0.2438	0.7839	0.5793	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0307 (4)	0.0292 (5)	0.0286 (4)	−0.0031 (4)	0.0053 (3)	0.0013 (3)
P2	0.0286 (4)	0.0299 (4)	0.0259 (4)	0.0033 (4)	0.0063 (3)	0.0010 (3)
C1	0.0281 (16)	0.039 (2)	0.0238 (14)	−0.0027 (14)	0.0073 (11)	−0.0003 (12)
C2	0.0352 (18)	0.041 (2)	0.0445 (17)	0.0017 (15)	0.0134 (13)	−0.0071 (15)
C3	0.045 (2)	0.055 (3)	0.052 (2)	0.0124 (19)	0.0189 (16)	−0.0026 (17)
C4	0.0280 (18)	0.084 (3)	0.0390 (18)	0.0053 (19)	0.0101 (13)	0.0035 (18)
C5	0.0329 (19)	0.069 (3)	0.0366 (17)	−0.0127 (18)	0.0046 (13)	−0.0006 (16)
C6	0.0365 (18)	0.039 (2)	0.0350 (16)	−0.0053 (14)	0.0044 (13)	−0.0009 (13)
C7	0.0350 (18)	0.0294 (19)	0.0392 (18)	−0.0099 (15)	0.0124 (13)	−0.0020 (14)
C8	0.057 (2)	0.035 (2)	0.045 (2)	−0.0091 (17)	0.0239 (16)	−0.0021 (15)
C9	0.080 (3)	0.052 (3)	0.052 (2)	−0.019 (2)	0.0369 (19)	−0.0087 (19)
C10	0.086 (3)	0.045 (3)	0.087 (3)	−0.011 (2)	0.060 (2)	−0.019 (2)
C11	0.059 (3)	0.036 (2)	0.092 (3)	0.0029 (19)	0.035 (2)	−0.009 (2)
C12	0.042 (2)	0.037 (2)	0.060 (2)	−0.0022 (18)	0.0134 (16)	−0.0012 (17)
C13	0.0229 (15)	0.0253 (16)	0.0263 (14)	0.0008 (12)	0.0074 (11)	0.0002 (12)
C14	0.0271 (15)	0.0345 (19)	0.0246 (14)	0.0008 (14)	0.0011 (11)	0.0020 (13)
C15	0.0346 (17)	0.033 (2)	0.0248 (14)	0.0019 (14)	0.0062 (11)	0.0088 (12)
C16	0.0288 (16)	0.0258 (17)	0.0312 (15)	0.0044 (13)	0.0102 (12)	0.0029 (12)
C17	0.0429 (19)	0.0252 (18)	0.0368 (16)	−0.0001 (15)	0.0098 (13)	0.0089 (13)
C18	0.044 (2)	0.031 (2)	0.0467 (19)	−0.0152 (15)	0.0091 (15)	0.0021 (15)
C19	0.0411 (19)	0.034 (2)	0.0377 (17)	−0.0099 (15)	0.0020 (13)	−0.0013 (14)
C20	0.0397 (17)	0.031 (2)	0.0261 (15)	−0.0027 (14)	0.0059 (12)	0.0003 (12)
C21	0.0254 (14)	0.0227 (16)	0.0243 (13)	0.0039 (13)	0.0074 (10)	0.0014 (12)
C22	0.0255 (14)	0.0202 (16)	0.0238 (13)	0.0048 (12)	0.0069 (10)	0.0013 (11)
C23	0.0244 (14)	0.0219 (17)	0.0224 (13)	−0.0054 (12)	0.0029 (10)	0.0009 (11)
C24	0.0224 (14)	0.0243 (16)	0.0266 (13)	−0.0031 (13)	0.0029 (10)	0.0035 (12)
C25	0.0334 (16)	0.039 (2)	0.0351 (16)	0.0078 (15)	0.0117 (13)	0.0068 (13)
C26	0.044 (2)	0.046 (2)	0.0472 (19)	0.0141 (17)	0.0167 (15)	0.0033 (16)
C27	0.044 (2)	0.039 (2)	0.061 (2)	0.0193 (17)	0.0153 (16)	0.0158 (17)
C28	0.0323 (17)	0.039 (2)	0.0441 (18)	0.0020 (15)	0.0060 (13)	0.0151 (15)
C29	0.0232 (15)	0.0261 (18)	0.0321 (15)	−0.0027 (13)	0.0026 (11)	0.0036 (12)
C30	0.0296 (16)	0.035 (2)	0.0262 (15)	−0.0040 (14)	0.0034 (11)	0.0098 (12)
C31	0.0307 (17)	0.0361 (19)	0.0220 (14)	−0.0039 (14)	0.0073 (11)	−0.0014 (12)
C32	0.0263 (15)	0.0250 (17)	0.0237 (14)	−0.0021 (13)	0.0042 (11)	0.0009 (12)
C33	0.0332 (17)	0.0297 (19)	0.0291 (15)	−0.0024 (14)	0.0131 (12)	−0.0028 (12)
C34	0.0325 (17)	0.035 (2)	0.0359 (16)	0.0038 (14)	0.0065 (12)	−0.0022 (14)
C35	0.0290 (18)	0.051 (2)	0.0459 (19)	−0.0031 (17)	0.0047 (13)	−0.0082 (16)
C36	0.040 (2)	0.044 (2)	0.0511 (19)	−0.0089 (17)	0.0155 (15)	−0.0174 (16)
C37	0.050 (2)	0.032 (2)	0.0519 (19)	0.0018 (16)	0.0129 (16)	−0.0056 (16)
C38	0.0351 (18)	0.038 (2)	0.0380 (18)	0.0057 (15)	0.0060 (13)	−0.0007 (14)
C39	0.0232 (15)	0.043 (2)	0.0289 (15)	0.0045 (14)	0.0018 (11)	0.0066 (13)
C40	0.0362 (17)	0.050 (2)	0.0347 (16)	0.0063 (16)	0.0097 (13)	0.0016 (14)
C41	0.044 (2)	0.077 (3)	0.0396 (18)	0.014 (2)	0.0176 (14)	0.0061 (19)
C42	0.0342 (19)	0.091 (3)	0.050 (2)	0.004 (2)	0.0150 (15)	0.026 (2)
C43	0.0318 (19)	0.063 (3)	0.066 (2)	−0.0096 (18)	0.0066 (16)	0.014 (2)
C44	0.0310 (18)	0.056 (2)	0.0430 (18)	−0.0065 (17)	0.0064 (13)	−0.0030 (16)

Geometric parameters (Å, º) top

P1—C1	1.828 (3)	C20—H20	0.950
P1—C13	1.838 (3)	C21—C22	1.437 (4)
P1—C7	1.837 (3)	C22—C23	1.504 (3)
P2—C33	1.832 (3)	C23—C32	1.389 (3)
P2—C39	1.841 (3)	C23—C24	1.422 (4)
P2—C32	1.843 (3)	C24—C25	1.420 (4)
C1—C2	1.387 (4)	C24—C29	1.426 (4)
C1—C6	1.391 (4)	C25—C26	1.364 (4)
C2—C3	1.392 (4)	C25—H25	0.950
C2—H2	0.950	C26—C27	1.396 (4)
C3—C4	1.381 (5)	C26—H26	0.950
C3—H3	0.950	C27—C28	1.362 (4)
C4—C5	1.374 (5)	C27—H27	0.950
C4—H4	0.950	C28—C29	1.413 (4)
C5—C6	1.385 (4)	C28—H28	0.950
C5—H5	0.950	C29—C30	1.413 (4)
C6—H6	0.950	C30—C31	1.361 (4)
C7—C12	1.387 (4)	C30—H30	0.950
C7—C8	1.399 (4)	C31—C32	1.414 (4)
C8—C9	1.387 (5)	C31—H31	0.950
C8—H8	0.950	C33—C34	1.385 (4)
C9—C10	1.381 (6)	C33—C38	1.399 (4)
C9—H9	0.950	C34—C35	1.395 (4)
C10—C11	1.376 (5)	C34—H34	0.950
C10—H10	0.950	C35—C36	1.380 (5)
C11—C12	1.377 (5)	C35—H35	0.950
C11—H11	0.950	C36—C37	1.367 (4)
C12—H12	0.950	C36—H36	0.950
C13—C22	1.376 (3)	C37—C38	1.385 (4)
C13—C14	1.425 (4)	C37—H37	0.950
C14—C15	1.367 (4)	C38—H38	0.950
C14—H14	0.950	C39—C44	1.380 (4)
C15—C16	1.414 (4)	C39—C40	1.393 (4)
C15—H15	0.950	C40—C41	1.392 (4)
C16—C17	1.415 (4)	C40—H40	0.950
C16—C21	1.418 (4)	C41—C42	1.372 (5)
C17—C18	1.360 (4)	C41—H41	0.950
C17—H17	0.950	C42—C43	1.380 (5)
C18—C19	1.398 (4)	C42—H42	0.950
C18—H18	0.950	C43—C44	1.388 (4)
C19—C20	1.365 (4)	C43—H43	0.950
C19—H19	0.950	C44—H44	0.950
C20—C21	1.417 (4)

C1—P1—C13	103.59 (13)	C13—C22—C21	120.3 (2)
C1—P1—C7	102.88 (13)	C13—C22—C23	121.0 (2)
C13—P1—C7	101.83 (12)	C21—C22—C23	118.7 (2)
C33—P2—C39	102.39 (13)	C32—C23—C24	119.9 (2)
C33—P2—C32	101.88 (12)	C32—C23—C22	121.0 (2)
C39—P2—C32	100.36 (13)	C24—C23—C22	119.0 (2)
C2—C1—C6	118.2 (3)	C25—C24—C23	122.4 (2)
C2—C1—P1	121.7 (2)	C25—C24—C29	117.7 (3)
C6—C1—P1	119.3 (2)	C23—C24—C29	119.9 (2)
C1—C2—C3	120.5 (3)	C26—C25—C24	121.1 (3)
C1—C2—H2	119.7	C26—C25—H25	119.4
C3—C2—H2	119.7	C24—C25—H25	119.4
C4—C3—C2	120.5 (3)	C25—C26—C27	120.8 (3)
C4—C3—H3	119.8	C25—C26—H26	119.6
C2—C3—H3	119.8	C27—C26—H26	119.6
C5—C4—C3	119.4 (3)	C28—C27—C26	120.0 (3)
C5—C4—H4	120.3	C28—C27—H27	120.0
C3—C4—H4	120.3	C26—C27—H27	120.0
C4—C5—C6	120.4 (3)	C27—C28—C29	121.2 (3)
C4—C5—H5	119.8	C27—C28—H28	119.4
C6—C5—H5	119.8	C29—C28—H28	119.4
C5—C6—C1	121.1 (3)	C28—C29—C30	122.6 (2)
C5—C6—H6	119.5	C28—C29—C24	119.1 (2)
C1—C6—H6	119.5	C30—C29—C24	118.3 (2)
C12—C7—C8	118.3 (3)	C31—C30—C29	121.1 (2)
C12—C7—P1	116.8 (2)	C31—C30—H30	119.5
C8—C7—P1	124.9 (3)	C29—C30—H30	119.5
C9—C8—C7	120.5 (3)	C30—C31—C32	121.4 (2)
C9—C8—H8	119.8	C30—C31—H31	119.3
C7—C8—H8	119.8	C32—C31—H31	119.3
C10—C9—C8	119.6 (3)	C23—C32—C31	119.4 (2)
C10—C9—H9	120.2	C23—C32—P2	118.93 (19)
C8—C9—H9	120.2	C31—C32—P2	121.6 (2)
C11—C10—C9	120.7 (3)	C34—C33—C38	118.0 (3)
C11—C10—H10	119.7	C34—C33—P2	125.4 (2)
C9—C10—H10	119.7	C38—C33—P2	116.6 (2)
C10—C11—C12	119.5 (4)	C33—C34—C35	120.3 (3)
C10—C11—H11	120.2	C33—C34—H34	119.8
C12—C11—H11	120.2	C35—C34—H34	119.8
C11—C12—C7	121.4 (3)	C36—C35—C34	120.5 (3)
C11—C12—H12	119.3	C36—C35—H35	119.7
C7—C12—H12	119.3	C34—C35—H35	119.7
C22—C13—C14	119.5 (3)	C37—C36—C35	119.9 (3)
C22—C13—P1	118.16 (19)	C37—C36—H36	120.1
C14—C13—P1	122.35 (19)	C35—C36—H36	120.1
C15—C14—C13	121.1 (2)	C36—C37—C38	120.0 (3)
C15—C14—H14	119.4	C36—C37—H37	120.0
C13—C14—H14	119.4	C38—C37—H37	120.0
C14—C15—C16	120.6 (2)	C37—C38—C33	121.3 (3)
C14—C15—H15	119.7	C37—C38—H38	119.4
C16—C15—H15	119.7	C33—C38—H38	119.4
C17—C16—C15	122.0 (2)	C44—C39—C40	118.4 (3)
C17—C16—C21	118.8 (2)	C44—C39—P2	117.8 (2)
C15—C16—C21	119.2 (3)	C40—C39—P2	123.7 (2)
C18—C17—C16	121.1 (3)	C39—C40—C41	120.1 (3)
C18—C17—H17	119.4	C39—C40—H40	119.9
C16—C17—H17	119.4	C41—C40—H40	119.9
C17—C18—C19	120.0 (3)	C42—C41—C40	120.6 (3)
C17—C18—H18	120.0	C42—C41—H41	119.7
C19—C18—H18	120.0	C40—C41—H41	119.7
C20—C19—C18	120.7 (3)	C41—C42—C43	119.8 (3)
C20—C19—H19	119.6	C41—C42—H42	120.1
C18—C19—H19	119.6	C43—C42—H42	120.1
C19—C20—C21	120.7 (3)	C42—C43—C44	119.6 (4)
C19—C20—H20	119.6	C42—C43—H43	120.2
C21—C20—H20	119.6	C44—C43—H43	120.2
C20—C21—C16	118.5 (3)	C39—C44—C43	121.5 (3)
C20—C21—C22	122.3 (2)	C39—C44—H44	119.3
C16—C21—C22	119.2 (2)	C43—C44—H44	119.3

C7—P1—C1—C2	143.3 (2)	C13—C22—C23—C24	−87.6 (3)
C13—P1—C1—C2	37.6 (2)	C21—C22—C23—C24	92.9 (3)
C7—P1—C1—C6	−47.7 (2)	C32—C23—C24—C25	178.3 (3)
C13—P1—C1—C6	−153.5 (2)	C22—C23—C24—C25	−2.4 (4)
C6—C1—C2—C3	1.8 (4)	C32—C23—C24—C29	−2.9 (4)
P1—C1—C2—C3	170.9 (2)	C22—C23—C24—C29	176.3 (2)
C1—C2—C3—C4	−1.1 (5)	C23—C24—C25—C26	177.0 (3)
C2—C3—C4—C5	−0.4 (5)	C29—C24—C25—C26	−1.8 (4)
C3—C4—C5—C6	1.0 (4)	C24—C25—C26—C27	1.1 (5)
C4—C5—C6—C1	−0.2 (4)	C25—C26—C27—C28	−0.2 (5)
C2—C1—C6—C5	−1.2 (4)	C26—C27—C28—C29	−0.1 (5)
P1—C1—C6—C5	−170.5 (2)	C27—C28—C29—C30	179.9 (3)
C1—P1—C7—C12	149.1 (2)	C27—C28—C29—C24	−0.7 (4)
C13—P1—C7—C12	−103.8 (2)	C25—C24—C29—C28	1.5 (4)
C1—P1—C7—C8	−30.7 (3)	C23—C24—C29—C28	−177.3 (3)
C13—P1—C7—C8	76.4 (3)	C25—C24—C29—C30	−179.0 (3)
C12—C7—C8—C9	−0.9 (5)	C23—C24—C29—C30	2.2 (4)
P1—C7—C8—C9	178.9 (3)	C28—C29—C30—C31	179.1 (3)
C7—C8—C9—C10	1.1 (5)	C24—C29—C30—C31	−0.4 (4)
C8—C9—C10—C11	0.2 (6)	C29—C30—C31—C32	−0.8 (4)
C9—C10—C11—C12	−1.6 (6)	C24—C23—C32—C31	1.7 (4)
C10—C11—C12—C7	1.7 (5)	C22—C23—C32—C31	−177.5 (2)
C8—C7—C12—C11	−0.4 (5)	C24—C23—C32—P2	−179.64 (19)
P1—C7—C12—C11	179.7 (3)	C22—C23—C32—P2	1.2 (3)
C1—P1—C13—C22	−137.7 (2)	C30—C31—C32—C23	0.1 (4)
C7—P1—C13—C22	115.8 (2)	C30—C31—C32—P2	−178.5 (2)
C1—P1—C13—C14	43.7 (2)	C33—P2—C32—C23	107.5 (2)
C7—P1—C13—C14	−62.9 (2)	C39—P2—C32—C23	−147.4 (2)
C22—C13—C14—C15	0.8 (4)	C33—P2—C32—C31	−74.0 (2)
P1—C13—C14—C15	179.5 (2)	C39—P2—C32—C31	31.2 (2)
C13—C14—C15—C16	−1.6 (4)	C39—P2—C33—C34	−101.1 (3)
C14—C15—C16—C17	−179.0 (3)	C32—P2—C33—C34	2.4 (3)
C14—C15—C16—C21	−0.5 (4)	C39—P2—C33—C38	80.8 (2)
C15—C16—C17—C18	175.5 (3)	C32—P2—C33—C38	−175.6 (2)
C21—C16—C17—C18	−2.9 (4)	C38—C33—C34—C35	0.1 (4)
C16—C17—C18—C19	0.2 (5)	P2—C33—C34—C35	−177.9 (2)
C17—C18—C19—C20	2.0 (5)	C33—C34—C35—C36	−0.8 (5)
C18—C19—C20—C21	−1.4 (5)	C34—C35—C36—C37	1.1 (5)
C19—C20—C21—C16	−1.3 (4)	C35—C36—C37—C38	−0.7 (5)
C19—C20—C21—C22	−179.6 (3)	C36—C37—C38—C33	0.0 (5)
C15—C16—C21—C20	−175.1 (3)	C34—C33—C38—C37	0.3 (4)
C17—C16—C21—C20	3.4 (4)	P2—C33—C38—C37	178.5 (2)
C15—C16—C21—C22	3.3 (4)	C33—P2—C39—C44	162.8 (2)
C17—C16—C21—C22	−178.3 (2)	C32—P2—C39—C44	58.1 (2)
C14—C13—C22—C21	2.0 (4)	C33—P2—C39—C40	−21.3 (3)
P1—C13—C22—C21	−176.74 (19)	C32—P2—C39—C40	−126.1 (2)
C14—C13—C22—C23	−177.5 (2)	C44—C39—C40—C41	−1.0 (4)
P1—C13—C22—C23	3.8 (3)	P2—C39—C40—C41	−176.8 (2)
C20—C21—C22—C13	174.3 (3)	C39—C40—C41—C42	−0.5 (5)
C16—C21—C22—C13	−4.0 (4)	C40—C41—C42—C43	1.1 (5)
C20—C21—C22—C23	−6.3 (4)	C41—C42—C43—C44	−0.2 (5)
C16—C21—C22—C23	175.5 (2)	C40—C39—C44—C43	1.9 (4)
C13—C22—C23—C32	91.6 (3)	P2—C39—C44—C43	177.9 (2)
C21—C22—C23—C32	−87.9 (3)	C42—C43—C44—C39	−1.3 (5)

Experimental details

Crystal data
Chemical formula	C₄₄H₃₂P₂
M_r	622.64
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	180
a, b, c (Å)	9.1206 (2), 18.7541 (7), 9.9829 (3)
β (°)	103.206 (2)
V (Å³)	1662.40 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.23 × 0.21 × 0.16

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.934, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11117, 5303, 4457
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.088, 1.04
No. of reflections	5303
No. of parameters	415
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28
Absolute structure	Flack (1983)
Absolute structure parameter	−0.04 (8)

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top

P1—C1	1.828 (3)	P2—C39	1.841 (3)
P1—C13	1.838 (3)	P2—C32	1.843 (3)
P1—C7	1.837 (3)	C22—C23	1.504 (3)
P2—C33	1.832 (3)

C1—P1—C13	103.59 (13)	C33—P2—C39	102.39 (13)
C1—P1—C7	102.88 (13)	C33—P2—C32	101.88 (12)
C13—P1—C7	101.83 (12)	C39—P2—C32	100.36 (13)

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(S)-(-)-2,2'-Bis­(di­phenyl­phosphino)-1,1'-bi­naphthyl, a versatile chelating ligand

Supporting information

Key indicators

checkCIF results

(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, a versatile chelating ligand