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

Guo, R.; Ao-Yueng, T.T.L.; Choi, M.C.K.; Zhou, Z.

doi:10.1107/S1600536802006098

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

R. Guo, T. T. L. Ao-Yueng, M. C. K. Choi and Z. Zhou

The title molecule, C₅₂H₅₈N₂P₂, has a non-crystallographic twofold axis. The bond lengths and angles are within expected ranges.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006098/cv6105sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006098/cv6105Isup2.hkl Contains datablock I

CCDC reference: 185792

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R factor = 0.051
wR factor = 0.102
Data-to-parameter ratio = 20.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.105

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(5)   -   C(6)   =       1.43 Ang.

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(6)   -   C(7)   =       1.37 Ang.

PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(1A)             ?

PLAT_420  Alert C D-H Without Acceptor       N(2)   -   H(2A)             ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.59
         From the CIF: _reflns_number_total              10453
         Count of symmetry unique reflns         5821
         Completeness (_total/calc)            179.57%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      4632
         Fraction of Friedel pairs measured     0.796
         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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 5 Alert Level C = Please check

Comment top

The aminophosphine ligands exhibit excellent enantioselectivity and high reactivity in the hydrogenation of prochiral olefines (Zhang et al., 1998; Chan et al., 1997). Recent studies show that the aminophosphine ligands derived from BINAM or H₈-BINAM give different enantioselectivity in the catalytic hydrogenation reaction due to the steric and electronic modulation of the binaphthyl unit or H₈-binaphthyl unit (Zhang et al., 1998). As part of our efforts in investigating of this phenomenon, we present the crystal structure of the title compound, (I).

The molecular structure of (I) (Fig. 1) shows the title molecule has a non-crystallographic twofold axis. The torsion angles C9—C10—C11—C12 and C1—C10—C11—C20 are 89.6 (5) and 86.0 (5)°, respectively.

Experimental top

All reactions were carried out under N₂ using Schlenk techniques. (R)-2,2'-Diamino-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (292 mg, 1.0 mmol) and 4-N,N-dimethylaminopyridine (15 mg) were added to a 50 ml round-bottomed Schlenk flask with a stirrer bar. The atmosphere was replaced with N₂ several times and 0.8 ml dry Et₃N and 30 ml dry CH₂Cl₂ were added. The mixture cooled to 273 K in an ice bath, and bis(3,5-dimethylphenyl)phosphine chloride (2.5 mmol) was added dropwise over a period of 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). The toluene was removed and 645 mg white solid obtained (yield: 85%). Colorless crystal suitable for X-ray diffraction were obtained by recrystallization from a solution in Et₂O. ³¹P NMR (CDCl₃): δ 25.2 p.p.m.

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) with displacement ellipsoids at the 30% probability level.

(R)-2,2'-bis[bis(3,5-dimethylphenyl)phosphinoamino]- 5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl top

Crystal data top

C₅₂H₅₈N₂P₂	D_x = 1.132 Mg m⁻³
M_r = 772.98	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 5067 reflections
a = 10.1595 (12) Å	θ = 1–27.5°
b = 19.961 (2) Å	µ = 0.13 mm⁻¹
c = 22.360 (3) Å	T = 294 K
V = 4534.4 (10) Å³	Prism, colorless
Z = 4	0.30 × 0.28 × 0.26 mm
F(000) = 1656

Data collection top

Bruker CCD area-detector diffractometer	10453 independent reflections
Radiation source: fine-focus sealed tube	3189 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.105
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −10→13
T_min = 0.962, T_max = 0.967	k = −25→25
31371 measured reflections	l = −29→23

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max = 0.007
10453 reflections	Δρ_max = 0.40 e Å⁻³
511 parameters	Δρ_min = −0.30 e Å⁻³
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (10)

Crystal data top

C₅₂H₅₈N₂P₂	V = 4534.4 (10) Å³
M_r = 772.98	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.1595 (12) Å	µ = 0.13 mm⁻¹
b = 19.961 (2) Å	T = 294 K
c = 22.360 (3) Å	0.30 × 0.28 × 0.26 mm

Data collection top

Bruker CCD area-detector diffractometer	10453 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	3189 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.967	R_int = 0.105
31371 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	Δρ_max = 0.40 e Å⁻³
S = 0.85	Δρ_min = −0.30 e Å⁻³
10453 reflections	Absolute structure: Flack (1983)
511 parameters	Absolute structure parameter: 0.09 (10)
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 were refined. 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	0.03763 (11)	0.12584 (5)	0.17884 (5)	0.0523 (3)
P2	0.36366 (12)	0.27424 (6)	0.35576 (6)	0.0621 (4)
N1	0.1484 (3)	0.18901 (15)	0.17365 (15)	0.0548 (10)
H1A	0.1941	0.1794	0.1423	0.066*
N2	0.3263 (3)	0.28799 (14)	0.28226 (15)	0.0580 (10)
H2A	0.3186	0.3308	0.2791	0.070*
C1	0.1181 (4)	0.25710 (19)	0.16662 (17)	0.0460 (11)
C2	−0.0110 (4)	0.2796 (2)	0.15880 (18)	0.0568 (12)
H2B	−0.0800	0.2491	0.1566	0.068*
C3	−0.0352 (4)	0.3465 (2)	0.15447 (18)	0.0625 (13)
H3A	−0.1216	0.3608	0.1491	0.075*
C4	0.0634 (5)	0.3942 (2)	0.1577 (2)	0.0588 (13)
C5	0.0278 (5)	0.4670 (2)	0.1542 (3)	0.102 (2)
H5A	0.0047	0.4778	0.1132	0.122*
H5B	−0.0492	0.4749	0.1788	0.122*
C6	0.1309 (7)	0.5107 (3)	0.1733 (3)	0.145 (3)
H6A	0.1379	0.5451	0.1428	0.174*
H6B	0.0988	0.5327	0.2091	0.174*
C7	0.2574 (7)	0.4910 (3)	0.1857 (3)	0.139 (3)
H7A	0.2716	0.4982	0.2282	0.167*
H7B	0.3158	0.5214	0.1647	0.167*
C8	0.3027 (4)	0.4212 (2)	0.1719 (2)	0.0799 (16)
H8A	0.3595	0.4057	0.2039	0.096*
H8B	0.3542	0.4219	0.1354	0.096*
C9	0.1902 (4)	0.3721 (2)	0.16454 (18)	0.0497 (11)
C10	0.2210 (4)	0.3046 (2)	0.16855 (18)	0.0444 (11)
C11	0.3557 (4)	0.27871 (18)	0.1761 (2)	0.0450 (10)
C12	0.4061 (4)	0.2695 (2)	0.2340 (2)	0.0507 (11)
C13	0.5300 (4)	0.24241 (19)	0.2412 (2)	0.0619 (13)
H13A	0.5651	0.2384	0.2794	0.074*
C14	0.6027 (4)	0.2211 (2)	0.1926 (2)	0.0658 (14)
H14A	0.6843	0.2011	0.1986	0.079*
C15	0.5559 (4)	0.2293 (2)	0.1354 (2)	0.0517 (12)
C16	0.6366 (4)	0.2054 (2)	0.0826 (2)	0.0792 (16)
H16A	0.7012	0.2394	0.0727	0.095*
H16B	0.6838	0.1651	0.0940	0.095*
C17	0.5562 (5)	0.1909 (3)	0.0287 (2)	0.1001 (19)
H17A	0.6144	0.1833	−0.0050	0.120*
H17B	0.5065	0.1501	0.0353	0.120*
C18	0.4655 (5)	0.2446 (3)	0.0138 (2)	0.0848 (16)
H18A	0.4115	0.2303	−0.0196	0.102*
H18B	0.5161	0.2831	0.0008	0.102*
C19	0.3748 (4)	0.2664 (2)	0.06478 (19)	0.0625 (13)
H19A	0.3519	0.3131	0.0590	0.075*
H19B	0.2942	0.2405	0.0626	0.075*
C20	0.4325 (4)	0.25831 (18)	0.1263 (2)	0.0474 (12)
C21	0.0238 (5)	0.09310 (18)	0.10322 (19)	0.0485 (12)
C22	−0.0922 (4)	0.0626 (2)	0.0866 (2)	0.0629 (14)
H22A	−0.1586	0.0577	0.1149	0.075*
C23	−0.1132 (5)	0.0389 (3)	0.0293 (2)	0.0720 (15)
C24	−0.0144 (5)	0.0469 (2)	−0.0127 (2)	0.0671 (14)
H24A	−0.0276	0.0315	−0.0515	0.080*
C25	0.1037 (5)	0.0773 (2)	0.0019 (2)	0.0534 (12)
C26	0.1216 (4)	0.09954 (19)	0.0599 (2)	0.0605 (13)
H26A	0.2012	0.1194	0.0703	0.073*
C27	−0.2443 (4)	0.0069 (3)	0.0116 (2)	0.111 (2)
H27A	−0.2507	−0.0368	0.0292	0.167*
H27B	−0.2489	0.0031	−0.0312	0.167*
H27C	−0.3155	0.0343	0.0256	0.167*
C28	0.2096 (5)	0.0882 (2)	−0.04485 (19)	0.0862 (17)
H28A	0.2177	0.0487	−0.0691	0.129*
H28B	0.2920	0.0971	−0.0254	0.129*
H28C	0.1862	0.1256	−0.0696	0.129*
C29	0.1477 (4)	0.0647 (2)	0.21294 (19)	0.0518 (12)
C30	0.1507 (4)	−0.0023 (2)	0.1956 (2)	0.0641 (14)
H30A	0.0996	−0.0160	0.1634	0.077*
C31	0.2268 (5)	−0.0488 (2)	0.2248 (2)	0.0639 (14)
C32	0.3053 (4)	−0.0269 (2)	0.2719 (2)	0.0695 (14)
H32A	0.3599	−0.0578	0.2907	0.083*
C33	0.3061 (4)	0.0394 (3)	0.2923 (2)	0.0681 (14)
C34	0.2247 (4)	0.0838 (2)	0.2614 (2)	0.0572 (12)
H34A	0.2218	0.1282	0.2739	0.069*
C35	0.2292 (4)	−0.12072 (19)	0.2051 (2)	0.0962 (18)
H35A	0.1407	−0.1371	0.2017	0.144*
H35B	0.2764	−0.1471	0.2339	0.144*
H35C	0.2721	−0.1240	0.1669	0.144*
C36	0.3896 (4)	0.0629 (2)	0.3426 (2)	0.0892 (17)
H36A	0.3384	0.0910	0.3686	0.134*
H36B	0.4628	0.0879	0.3271	0.134*
H36C	0.4215	0.0250	0.3647	0.134*
C37	0.1976 (4)	0.2814 (2)	0.3862 (2)	0.0573 (12)
C38	0.1722 (5)	0.3129 (2)	0.4398 (2)	0.0728 (15)
H38A	0.2407	0.3346	0.4594	0.087*
C39	0.0496 (7)	0.3132 (3)	0.4651 (3)	0.0854 (17)
C40	−0.0517 (5)	0.2807 (3)	0.4366 (3)	0.0800 (16)
H40A	−0.1347	0.2808	0.4541	0.096*
C41	−0.0344 (6)	0.2479 (2)	0.3826 (3)	0.0752 (15)
C42	0.0917 (5)	0.2493 (2)	0.3581 (2)	0.0671 (14)
H42A	0.1061	0.2281	0.3216	0.080*
C43	0.0258 (5)	0.3503 (3)	0.5240 (2)	0.126 (2)
H43A	0.0846	0.3334	0.5541	0.189*
H43B	−0.0635	0.3435	0.5366	0.189*
H43C	0.0415	0.3973	0.5184	0.189*
C44	−0.1450 (5)	0.2115 (2)	0.3512 (3)	0.117 (2)
H44A	−0.2279	0.2293	0.3641	0.176*
H44B	−0.1408	0.1646	0.3606	0.176*
H44C	−0.1363	0.2174	0.3087	0.176*
C45	0.4383 (4)	0.3516 (2)	0.3825 (2)	0.0594 (13)
C46	0.5125 (4)	0.3476 (2)	0.4342 (2)	0.0742 (15)
H46A	0.5211	0.3063	0.4530	0.089*
C47	0.5742 (5)	0.4026 (3)	0.4588 (3)	0.0819 (17)
C48	0.5647 (5)	0.4627 (3)	0.4275 (3)	0.0904 (19)
H48A	0.6081	0.5002	0.4424	0.109*
C49	0.4935 (5)	0.4692 (3)	0.3751 (3)	0.0743 (16)
C50	0.4291 (4)	0.4125 (3)	0.3537 (2)	0.0669 (14)
H50A	0.3785	0.4158	0.3192	0.080*
C51	0.6505 (5)	0.3998 (3)	0.5156 (3)	0.144 (3)
H51B	0.6046	0.4243	0.5461	0.216*
H51C	0.7358	0.4193	0.5095	0.216*
H51D	0.6603	0.3540	0.5279	0.216*
C52	0.4800 (5)	0.5356 (2)	0.3433 (2)	0.106 (2)
H52B	0.3899	0.5500	0.3447	0.160*
H52C	0.5071	0.5308	0.3024	0.160*
H52D	0.5346	0.5683	0.3627	0.160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0472 (8)	0.0510 (7)	0.0587 (8)	−0.0016 (6)	0.0011 (7)	−0.0031 (7)
P2	0.0688 (9)	0.0644 (9)	0.0532 (9)	0.0031 (7)	−0.0028 (7)	−0.0068 (7)
N1	0.053 (2)	0.040 (2)	0.072 (3)	−0.0039 (18)	0.011 (2)	−0.006 (2)
N2	0.080 (3)	0.050 (2)	0.044 (3)	0.007 (2)	0.003 (2)	−0.009 (2)
C1	0.050 (3)	0.041 (3)	0.048 (3)	0.007 (2)	0.001 (2)	−0.006 (2)
C2	0.047 (3)	0.060 (3)	0.064 (3)	0.014 (3)	−0.009 (2)	−0.004 (3)
C3	0.053 (3)	0.071 (3)	0.063 (3)	0.027 (3)	−0.007 (3)	0.002 (3)
C4	0.073 (4)	0.048 (3)	0.055 (3)	0.024 (3)	0.014 (3)	0.011 (2)
C5	0.108 (5)	0.056 (4)	0.143 (6)	0.030 (3)	0.014 (4)	−0.003 (4)
C6	0.205 (9)	0.081 (5)	0.149 (5)	0.035 (6)	−0.005 (6)	−0.008 (5)
C7	0.224 (9)	0.068 (5)	0.126 (5)	−0.005 (5)	−0.073 (6)	−0.007 (4)
C8	0.095 (4)	0.052 (3)	0.093 (4)	−0.001 (3)	0.041 (3)	0.000 (3)
C9	0.055 (3)	0.044 (3)	0.050 (3)	0.001 (3)	0.010 (2)	0.002 (2)
C10	0.036 (3)	0.041 (3)	0.056 (3)	0.005 (2)	0.009 (2)	0.005 (2)
C11	0.051 (3)	0.040 (2)	0.044 (3)	0.000 (2)	−0.001 (3)	−0.003 (2)
C12	0.047 (3)	0.049 (3)	0.056 (3)	−0.001 (2)	0.001 (3)	−0.005 (3)
C13	0.052 (3)	0.069 (3)	0.065 (4)	0.008 (3)	−0.011 (3)	−0.012 (3)
C14	0.039 (3)	0.072 (3)	0.086 (5)	0.010 (3)	0.008 (3)	−0.006 (3)
C15	0.042 (3)	0.054 (3)	0.059 (4)	−0.001 (3)	0.007 (3)	−0.003 (3)
C16	0.061 (4)	0.093 (4)	0.084 (4)	0.002 (3)	0.024 (3)	−0.008 (3)
C17	0.103 (5)	0.121 (5)	0.076 (5)	0.036 (4)	0.033 (4)	−0.017 (4)
C18	0.078 (4)	0.109 (4)	0.068 (4)	0.013 (4)	0.017 (3)	−0.006 (3)
C19	0.068 (3)	0.067 (3)	0.052 (3)	0.013 (3)	0.005 (3)	0.005 (3)
C20	0.047 (3)	0.040 (3)	0.056 (4)	−0.002 (2)	0.006 (2)	0.001 (2)
C21	0.054 (3)	0.037 (3)	0.055 (3)	−0.010 (2)	0.003 (3)	0.003 (2)
C22	0.050 (3)	0.068 (3)	0.070 (4)	−0.003 (3)	0.007 (3)	−0.002 (3)
C23	0.061 (4)	0.084 (4)	0.071 (4)	−0.015 (3)	−0.007 (3)	−0.014 (3)
C24	0.076 (4)	0.062 (3)	0.063 (4)	0.006 (3)	−0.011 (3)	−0.005 (3)
C25	0.061 (4)	0.054 (3)	0.045 (3)	−0.003 (3)	0.008 (3)	0.003 (3)
C26	0.061 (4)	0.048 (3)	0.073 (4)	−0.012 (2)	0.003 (3)	0.001 (3)
C27	0.072 (4)	0.168 (5)	0.094 (5)	−0.050 (4)	0.004 (3)	−0.046 (4)
C28	0.101 (4)	0.094 (4)	0.063 (4)	−0.017 (3)	0.020 (3)	0.000 (3)
C29	0.053 (3)	0.055 (3)	0.047 (3)	0.000 (3)	0.001 (2)	0.007 (2)
C30	0.071 (4)	0.062 (3)	0.059 (4)	0.000 (3)	−0.002 (3)	−0.001 (3)
C31	0.078 (4)	0.055 (3)	0.059 (4)	0.008 (3)	0.005 (3)	0.009 (3)
C32	0.069 (4)	0.068 (4)	0.071 (4)	0.014 (3)	0.015 (3)	0.018 (3)
C33	0.059 (4)	0.078 (4)	0.067 (4)	−0.008 (3)	0.005 (3)	0.011 (3)
C34	0.058 (3)	0.055 (3)	0.059 (4)	−0.003 (3)	0.000 (3)	−0.005 (3)
C35	0.121 (4)	0.049 (3)	0.118 (5)	0.021 (3)	0.011 (3)	−0.010 (3)
C36	0.097 (4)	0.097 (4)	0.073 (4)	0.008 (3)	−0.027 (3)	0.007 (3)
C37	0.068 (4)	0.055 (3)	0.048 (3)	0.003 (3)	0.011 (3)	−0.008 (3)
C38	0.071 (4)	0.078 (4)	0.070 (4)	−0.013 (3)	0.015 (3)	−0.002 (3)
C39	0.095 (5)	0.084 (4)	0.077 (5)	−0.004 (4)	0.015 (4)	−0.002 (3)
C40	0.066 (4)	0.072 (4)	0.102 (5)	0.003 (3)	0.025 (4)	0.013 (4)
C41	0.085 (5)	0.055 (3)	0.086 (5)	−0.008 (3)	0.009 (4)	−0.003 (3)
C42	0.076 (4)	0.059 (3)	0.066 (4)	−0.002 (3)	0.008 (3)	−0.010 (3)
C43	0.134 (5)	0.142 (6)	0.101 (5)	−0.024 (4)	0.053 (4)	−0.040 (4)
C44	0.076 (4)	0.101 (4)	0.175 (6)	−0.018 (4)	−0.008 (4)	−0.021 (4)
C45	0.046 (3)	0.079 (4)	0.053 (3)	−0.005 (3)	0.000 (2)	−0.014 (3)
C46	0.066 (4)	0.077 (4)	0.080 (4)	−0.007 (3)	−0.011 (3)	−0.021 (3)
C47	0.074 (5)	0.092 (4)	0.080 (5)	0.008 (4)	−0.014 (3)	−0.011 (4)
C48	0.067 (4)	0.098 (5)	0.106 (6)	−0.014 (4)	0.017 (4)	−0.041 (5)
C49	0.067 (4)	0.067 (4)	0.088 (5)	−0.012 (3)	0.032 (3)	−0.019 (4)
C50	0.069 (4)	0.070 (3)	0.062 (4)	0.001 (3)	0.014 (3)	−0.010 (3)
C51	0.117 (5)	0.169 (6)	0.146 (6)	0.014 (4)	−0.081 (5)	−0.066 (5)
C52	0.136 (5)	0.074 (4)	0.109 (5)	−0.014 (4)	0.048 (4)	−0.004 (4)

Geometric parameters (Å, º) top

P1—N1	1.694 (3)	C25—C26	1.383 (5)
P1—C21	1.818 (4)	C25—C28	1.516 (5)
P1—C29	1.822 (4)	C26—H26A	0.9300
P2—N2	1.709 (3)	C27—H27A	0.9600
P2—C45	1.822 (4)	C27—H27B	0.9600
P2—C37	1.825 (4)	C27—H27C	0.9600
N1—C1	1.402 (4)	C28—H28A	0.9600
N1—H1A	0.8617	C28—H28B	0.9600
N2—C12	1.399 (5)	C28—H28C	0.9600
N2—H2A	0.8619	C29—C34	1.390 (5)
C1—C2	1.397 (4)	C29—C30	1.393 (5)
C1—C10	1.413 (4)	C30—C31	1.374 (5)
C2—C3	1.362 (5)	C30—H30A	0.9300
C2—H2B	0.9300	C31—C32	1.391 (6)
C3—C4	1.384 (5)	C31—C35	1.502 (5)
C3—H3A	0.9300	C32—C33	1.400 (6)
C4—C9	1.369 (5)	C32—H32A	0.9300
C4—C5	1.499 (5)	C33—C34	1.394 (5)
C5—C6	1.428 (5)	C33—C36	1.484 (6)
C5—H5A	0.9700	C34—H34A	0.9300
C5—H5B	0.9700	C35—H35A	0.9600
C6—C7	1.373 (6)	C35—H35B	0.9600
C6—H6A	0.9700	C35—H35C	0.9600
C6—H6B	0.9700	C36—H36A	0.9600
C7—C8	1.499 (5)	C36—H36B	0.9600
C7—H7A	0.9700	C36—H36C	0.9600
C7—H7B	0.9700	C37—C38	1.376 (5)
C8—C9	1.514 (5)	C37—C42	1.402 (5)
C8—H8A	0.9700	C38—C39	1.368 (6)
C8—H8B	0.9700	C38—H38A	0.9300
C9—C10	1.387 (5)	C39—C40	1.373 (6)
C10—C11	1.472 (5)	C39—C43	1.531 (6)
C11—C12	1.404 (5)	C40—C41	1.384 (6)
C11—C20	1.418 (5)	C40—H40A	0.9300
C12—C13	1.380 (5)	C41—C42	1.394 (6)
C13—C14	1.381 (5)	C41—C44	1.512 (6)
C13—H13A	0.9300	C42—H42A	0.9300
C14—C15	1.373 (5)	C43—H43A	0.9600
C14—H14A	0.9300	C43—H43B	0.9600
C15—C20	1.396 (5)	C43—H43C	0.9600
C15—C16	1.515 (5)	C44—H44A	0.9600
C16—C17	1.485 (5)	C44—H44B	0.9600
C16—H16A	0.9700	C44—H44C	0.9600
C16—H16B	0.9700	C45—C50	1.379 (5)
C17—C18	1.452 (6)	C45—C46	1.381 (5)
C17—H17A	0.9700	C46—C47	1.379 (6)
C17—H17B	0.9700	C46—H46A	0.9300
C18—C19	1.528 (5)	C47—C48	1.394 (7)
C18—H18A	0.9700	C47—C51	1.488 (6)
C18—H18B	0.9700	C48—C49	1.383 (7)
C19—C20	1.504 (5)	C48—H48A	0.9300
C19—H19A	0.9700	C49—C50	1.391 (6)
C19—H19B	0.9700	C49—C52	1.510 (6)
C21—C22	1.378 (5)	C50—H50A	0.9300
C21—C26	1.394 (5)	C51—H51B	0.9600
C22—C23	1.382 (6)	C51—H51C	0.9600
C22—H22A	0.9300	C51—H51D	0.9600
C23—C24	1.384 (6)	C52—H52B	0.9600
C23—C27	1.529 (5)	C52—H52C	0.9600
C24—C25	1.383 (5)	C52—H52D	0.9600
C24—H24A	0.9300

N1—P1—C21	104.78 (18)	C26—C25—C24	118.5 (4)
N1—P1—C29	96.85 (17)	C26—C25—C28	120.5 (4)
C21—P1—C29	101.3 (2)	C24—C25—C28	121.1 (5)
N2—P2—C45	105.8 (2)	C25—C26—C21	121.9 (4)
N2—P2—C37	98.1 (2)	C25—C26—H26A	119.1
C45—P2—C37	101.3 (2)	C21—C26—H26A	119.1
C1—N1—P1	125.7 (3)	C23—C27—H27A	109.5
C1—N1—H1A	104.0	C23—C27—H27B	109.5
P1—N1—H1A	104.4	H27A—C27—H27B	109.5
C12—N2—P2	124.8 (3)	C23—C27—H27C	109.5
C12—N2—H2A	104.4	H27A—C27—H27C	109.5
P2—N2—H2A	105.0	H27B—C27—H27C	109.5
C2—C1—N1	122.1 (4)	C25—C28—H28A	109.5
C2—C1—C10	118.9 (4)	C25—C28—H28B	109.5
N1—C1—C10	118.9 (4)	H28A—C28—H28B	109.5
C3—C2—C1	119.6 (4)	C25—C28—H28C	109.5
C3—C2—H2B	120.2	H28A—C28—H28C	109.5
C1—C2—H2B	120.2	H28B—C28—H28C	109.5
C2—C3—C4	122.7 (4)	C34—C29—C30	117.8 (4)
C2—C3—H3A	118.7	C34—C29—P1	119.3 (3)
C4—C3—H3A	118.7	C30—C29—P1	122.7 (4)
C9—C4—C3	117.8 (4)	C31—C30—C29	122.0 (4)
C9—C4—C5	123.0 (5)	C31—C30—H30A	119.0
C3—C4—C5	119.2 (5)	C29—C30—H30A	119.0
C6—C5—C4	113.5 (5)	C30—C31—C32	118.0 (4)
C6—C5—H5A	108.9	C30—C31—C35	121.0 (5)
C4—C5—H5A	108.9	C32—C31—C35	121.0 (5)
C6—C5—H5B	108.9	C31—C32—C33	123.2 (5)
C4—C5—H5B	108.9	C31—C32—H32A	118.4
H5A—C5—H5B	107.7	C33—C32—H32A	118.4
C7—C6—C5	124.9 (6)	C34—C33—C32	115.8 (5)
C7—C6—H6A	106.1	C34—C33—C36	120.9 (5)
C5—C6—H6A	106.1	C32—C33—C36	123.3 (5)
C7—C6—H6B	106.1	C29—C34—C33	123.1 (4)
C5—C6—H6B	106.1	C29—C34—H34A	118.4
H6A—C6—H6B	106.3	C33—C34—H34A	118.4
C6—C7—C8	120.8 (6)	C31—C35—H35A	109.5
C6—C7—H7A	107.1	C31—C35—H35B	109.5
C8—C7—H7A	107.1	H35A—C35—H35B	109.5
C6—C7—H7B	107.1	C31—C35—H35C	109.5
C8—C7—H7B	107.1	H35A—C35—H35C	109.5
H7A—C7—H7B	106.8	H35B—C35—H35C	109.5
C7—C8—C9	113.1 (4)	C33—C36—H36A	109.5
C7—C8—H8A	109.0	C33—C36—H36B	109.5
C9—C8—H8A	109.0	H36A—C36—H36B	109.5
C7—C8—H8B	109.0	C33—C36—H36C	109.5
C9—C8—H8B	109.0	H36A—C36—H36C	109.5
H8A—C8—H8B	107.8	H36B—C36—H36C	109.5
C4—C9—C10	122.2 (4)	C38—C37—C42	117.1 (4)
C4—C9—C8	120.9 (4)	C38—C37—P2	122.3 (4)
C10—C9—C8	116.8 (4)	C42—C37—P2	120.4 (4)
C9—C10—C1	118.9 (4)	C39—C38—C37	122.2 (5)
C9—C10—C11	124.0 (4)	C39—C38—H38A	118.9
C1—C10—C11	117.2 (3)	C37—C38—H38A	118.9
C12—C11—C20	119.0 (4)	C38—C39—C40	119.2 (5)
C12—C11—C10	119.3 (4)	C38—C39—C43	120.2 (6)
C20—C11—C10	121.5 (4)	C40—C39—C43	120.6 (6)
C13—C12—N2	122.8 (4)	C39—C40—C41	122.2 (5)
C13—C12—C11	119.4 (4)	C39—C40—H40A	118.9
N2—C12—C11	117.8 (4)	C41—C40—H40A	118.9
C12—C13—C14	121.1 (4)	C40—C41—C42	116.8 (5)
C12—C13—H13A	119.5	C40—C41—C44	122.6 (5)
C14—C13—H13A	119.5	C42—C41—C44	120.6 (5)
C15—C14—C13	120.7 (4)	C41—C42—C37	122.5 (5)
C15—C14—H14A	119.6	C41—C42—H42A	118.8
C13—C14—H14A	119.6	C37—C42—H42A	118.8
C14—C15—C20	119.7 (4)	C39—C43—H43A	109.5
C14—C15—C16	120.1 (4)	C39—C43—H43B	109.5
C20—C15—C16	120.2 (4)	H43A—C43—H43B	109.5
C17—C16—C15	113.4 (4)	C39—C43—H43C	109.5
C17—C16—H16A	108.9	H43A—C43—H43C	109.5
C15—C16—H16A	108.9	H43B—C43—H43C	109.5
C17—C16—H16B	108.9	C41—C44—H44A	109.5
C15—C16—H16B	108.9	C41—C44—H44B	109.5
H16A—C16—H16B	107.7	H44A—C44—H44B	109.5
C18—C17—C16	113.0 (4)	C41—C44—H44C	109.5
C18—C17—H17A	109.0	H44A—C44—H44C	109.5
C16—C17—H17A	109.0	H44B—C44—H44C	109.5
C18—C17—H17B	109.0	C50—C45—C46	118.6 (4)
C16—C17—H17B	109.0	C50—C45—P2	124.4 (4)
H17A—C17—H17B	107.8	C46—C45—P2	116.9 (4)
C17—C18—C19	115.0 (4)	C47—C46—C45	122.4 (5)
C17—C18—H18A	108.5	C47—C46—H46A	118.8
C19—C18—H18A	108.5	C45—C46—H46A	118.8
C17—C18—H18B	108.5	C46—C47—C48	116.9 (5)
C19—C18—H18B	108.5	C46—C47—C51	123.2 (6)
H18A—C18—H18B	107.5	C48—C47—C51	119.9 (6)
C20—C19—C18	114.6 (4)	C49—C48—C47	122.9 (5)
C20—C19—H19A	108.6	C49—C48—H48A	118.6
C18—C19—H19A	108.6	C47—C48—H48A	118.6
C20—C19—H19B	108.6	C48—C49—C50	117.4 (5)
C18—C19—H19B	108.6	C48—C49—C52	121.8 (5)
H19A—C19—H19B	107.6	C50—C49—C52	120.7 (6)
C15—C20—C11	119.9 (4)	C45—C50—C49	121.6 (5)
C15—C20—C19	121.8 (4)	C45—C50—H50A	119.2
C11—C20—C19	118.2 (4)	C49—C50—H50A	119.2
C22—C21—C26	117.6 (4)	C47—C51—H51B	109.5
C22—C21—P1	118.4 (4)	C47—C51—H51C	109.5
C26—C21—P1	123.9 (4)	H51B—C51—H51C	109.5
C21—C22—C23	122.2 (4)	C47—C51—H51D	109.5
C21—C22—H22A	118.9	H51B—C51—H51D	109.5
C23—C22—H22A	118.9	H51C—C51—H51D	109.5
C22—C23—C24	118.5 (5)	C49—C52—H52B	109.5
C22—C23—C27	121.1 (5)	C49—C52—H52C	109.5
C24—C23—C27	120.3 (5)	H52B—C52—H52C	109.5
C25—C24—C23	121.3 (5)	C49—C52—H52D	109.5
C25—C24—H24A	119.3	H52B—C52—H52D	109.5
C23—C24—H24A	119.3	H52C—C52—H52D	109.5

C21—P1—N1—C1	95.7 (4)	N1—P1—C21—C26	24.1 (4)
C29—P1—N1—C1	−160.6 (3)	C29—P1—C21—C26	−76.2 (4)
C45—P2—N2—C12	95.8 (3)	C26—C21—C22—C23	−0.2 (7)
C37—P2—N2—C12	−160.0 (3)	P1—C21—C22—C23	177.1 (4)
P1—N1—C1—C2	−4.7 (6)	C21—C22—C23—C24	−0.6 (7)
P1—N1—C1—C10	174.2 (3)	C21—C22—C23—C27	−178.4 (4)
N1—C1—C2—C3	177.5 (4)	C22—C23—C24—C25	0.5 (7)
C10—C1—C2—C3	−1.4 (6)	C27—C23—C24—C25	178.3 (4)
C1—C2—C3—C4	−0.3 (7)	C23—C24—C25—C26	0.3 (7)
C2—C3—C4—C9	1.2 (7)	C23—C24—C25—C28	−177.7 (4)
C2—C3—C4—C5	−178.3 (4)	C24—C25—C26—C21	−1.0 (6)
C9—C4—C5—C6	−14.7 (8)	C28—C25—C26—C21	177.0 (4)
C3—C4—C5—C6	164.7 (5)	C22—C21—C26—C25	1.0 (6)
C4—C5—C6—C7	8.9 (11)	P1—C21—C26—C25	−176.1 (3)
C5—C6—C7—C8	8.5 (13)	N1—P1—C29—C34	47.8 (4)
C6—C7—C8—C9	−19.7 (9)	C21—P1—C29—C34	154.4 (4)
C3—C4—C9—C10	−0.4 (7)	N1—P1—C29—C30	−137.6 (3)
C5—C4—C9—C10	179.1 (4)	C21—P1—C29—C30	−31.0 (4)
C3—C4—C9—C8	−176.6 (4)	C34—C29—C30—C31	−0.2 (6)
C5—C4—C9—C8	2.9 (7)	P1—C29—C30—C31	−174.9 (3)
C7—C8—C9—C4	14.0 (6)	C29—C30—C31—C32	−1.8 (7)
C7—C8—C9—C10	−162.3 (4)	C29—C30—C31—C35	−179.5 (4)
C4—C9—C10—C1	−1.2 (6)	C30—C31—C32—C33	2.7 (7)
C8—C9—C10—C1	175.1 (4)	C35—C31—C32—C33	−179.6 (4)
C4—C9—C10—C11	−179.8 (4)	C31—C32—C33—C34	−1.5 (7)
C8—C9—C10—C11	−3.5 (6)	C31—C32—C33—C36	179.9 (4)
C2—C1—C10—C9	2.1 (6)	C30—C29—C34—C33	1.5 (7)
N1—C1—C10—C9	−176.9 (4)	P1—C29—C34—C33	176.4 (3)
C2—C1—C10—C11	−179.2 (4)	C32—C33—C34—C29	−0.7 (7)
N1—C1—C10—C11	1.8 (6)	C36—C33—C34—C29	178.0 (4)
C9—C10—C11—C12	89.6 (5)	N2—P2—C37—C38	−140.6 (4)
C1—C10—C11—C12	−89.0 (5)	C45—P2—C37—C38	−32.6 (4)
C9—C10—C11—C20	−94.9 (5)	N2—P2—C37—C42	45.4 (4)
C1—C10—C11—C20	86.4 (5)	C45—P2—C37—C42	153.4 (4)
P2—N2—C12—C13	−5.2 (5)	C42—C37—C38—C39	0.0 (7)
P2—N2—C12—C11	174.2 (3)	P2—C37—C38—C39	−174.2 (4)
C20—C11—C12—C13	1.5 (6)	C37—C38—C39—C40	0.5 (8)
C10—C11—C12—C13	177.1 (4)	C37—C38—C39—C43	−178.6 (4)
C20—C11—C12—N2	−177.9 (3)	C38—C39—C40—C41	−0.4 (8)
C10—C11—C12—N2	−2.3 (5)	C43—C39—C40—C41	178.6 (5)
N2—C12—C13—C14	176.1 (4)	C39—C40—C41—C42	−0.1 (7)
C11—C12—C13—C14	−3.2 (6)	C39—C40—C41—C44	179.4 (5)
C12—C13—C14—C15	3.0 (7)	C40—C41—C42—C37	0.7 (7)
C13—C14—C15—C20	−1.2 (7)	C44—C41—C42—C37	−178.9 (4)
C13—C14—C15—C16	−179.7 (4)	C38—C37—C42—C41	−0.7 (7)
C14—C15—C16—C17	155.7 (5)	P2—C37—C42—C41	173.7 (3)
C20—C15—C16—C17	−22.8 (6)	N2—P2—C45—C50	16.7 (4)
C15—C16—C17—C18	49.1 (6)	C37—P2—C45—C50	−85.1 (4)
C16—C17—C18—C19	−53.6 (6)	N2—P2—C45—C46	−161.0 (3)
C17—C18—C19—C20	30.3 (6)	C37—P2—C45—C46	97.1 (4)
C14—C15—C20—C11	−0.5 (6)	C50—C45—C46—C47	2.0 (7)
C16—C15—C20—C11	178.0 (4)	P2—C45—C46—C47	179.9 (4)
C14—C15—C20—C19	−178.0 (4)	C45—C46—C47—C48	−3.4 (8)
C16—C15—C20—C19	0.5 (6)	C45—C46—C47—C51	177.7 (5)
C12—C11—C20—C15	0.3 (6)	C46—C47—C48—C49	2.3 (8)
C10—C11—C20—C15	−175.2 (4)	C51—C47—C48—C49	−178.8 (5)
C12—C11—C20—C19	177.9 (4)	C47—C48—C49—C50	0.2 (8)
C10—C11—C20—C19	2.5 (5)	C47—C48—C49—C52	177.4 (4)
C18—C19—C20—C15	−3.7 (6)	C46—C45—C50—C49	0.7 (7)
C18—C19—C20—C11	178.7 (4)	P2—C45—C50—C49	−177.0 (3)
N1—P1—C21—C22	−153.0 (3)	C48—C49—C50—C45	−1.7 (7)
C29—P1—C21—C22	106.8 (3)	C52—C49—C50—C45	−179.0 (4)

Experimental details

Crystal data
Chemical formula	C₅₂H₅₈N₂P₂
M_r	772.98
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	10.1595 (12), 19.961 (2), 22.360 (3)
V (Å³)	4534.4 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 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	0.962, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	31371, 10453, 3189
R_int	0.105
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.102, 0.85
No. of reflections	10453
No. of parameters	511
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30
Absolute structure	Flack (1983)
Absolute structure parameter	0.09 (10)

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

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