Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006098/cv6105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006098/cv6105Isup2.hkl |
CCDC reference: 185792
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
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.
The Rint value is large. It is caused by the diffraction intensities of the crystal sample being too small. Information concerning crystal data collection and structure refinement of the compound is summarized in the CIF.
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.
Fig. 1. The molecular structure of (I) with displacement ellipsoids at the 30% probability level. |
C52H58N2P2 | Dx = 1.132 Mg m−3 |
Mr = 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 |
Bruker CCD area-detector diffractometer | 10453 independent reflections |
Radiation source: fine-focus sealed tube | 3189 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.105 |
ϕ and ω scans | θmax = 27.6°, θmin = 2.2° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −10→13 |
Tmin = 0.962, Tmax = 0.967 | k = −25→25 |
31371 measured reflections | l = −29→23 |
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(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max = 0.007 |
10453 reflections | Δρmax = 0.40 e Å−3 |
511 parameters | Δρmin = −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) |
C52H58N2P2 | V = 4534.4 (10) Å3 |
Mr = 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 |
Bruker CCD area-detector diffractometer | 10453 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3189 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.967 | Rint = 0.105 |
31371 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | Δρmax = 0.40 e Å−3 |
S = 0.85 | Δρmin = −0.30 e Å−3 |
10453 reflections | Absolute structure: Flack (1983) |
511 parameters | Absolute structure parameter: 0.09 (10) |
3 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.962, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31371, 10453, 3189 |
Rint | 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 |
Δρmax, Δρmin (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.
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.