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The title compound, C42H41NOP2Si, used as a nixantphos-type ligand in homogeneous catalysis, crystallizes with one mol­ecule in the asymmetric unit. The mol­ecule has nearly mirror symmetry with N, O and Si on the pseudo-mirror plane, but it is not located on a crystallographic mirror plane. The most important feature of the mol­ecule is the intra­molecular P-P distance of 4.1453 (12) Å. The bond angles involving the P atoms are in the range 100.32 (14)-103.04 (15)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027121/bt6724sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027121/bt6724Isup2.hkl
Contains datablock I

CCDC reference: 287463

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.079
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc. PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 - C6 .. 8.94 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C15 - C16 .. 7.82 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C21 - C22 .. 7.28 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C3
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 6.91 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), is a diphosphine ligand used for highly regioselective hydroformylation reactions, one of the most important homogeneously catalysed industrial reactions, which produces mixtures of linear and branched aldehydes from olefins, carbon monoxide and hydrogen (Claver & van Leeuwen, 2000). In order to achieve high selectivity towards formation of one product, the appropriate ligand must be employed. van Leeuwen has pioneered the use of xanthene- and phenoxazine-based diphosphine ligands (Kranenburg et al., 1995; van der Veen et al., 1998), which give extremely regioselective rhodium catalysts that produce linear aldehydes.

As part of our investigation of structural modifications of hydroformylation catalysts, the title new ligand, (I), was prepared following a modified literature procedure (Antonio et al., 1989; Petrassi et al., 2000; van der Veen et al., 2000). According to the preliminary results, this compound was found to be superior over nixantphos as a ligand with regard to selectivity (Osiński & Eilbracht, 2005). It was believed that a crystal structure determination of this compound might allow for the determination of important ligand factors, such as the cone angle and the flexibility range of the natural bite angle.

Experimental top

At 273 K, n-butyllithium (16 ml of 2.5 M in hexanes, 39 mmol) was added dropwise to a stirred solution of 10-(tertbutyldimethylsilyl)phenoxazine (4.84 g, 16.3 mmol) and TMEDA [Please give name in full] (5.9 ml, 39 mmol) in diethyl ether (250 ml). The reaction mixture was slowly warmed to room temperature and stirred for 16 h. The maize-yellow suspension was then cooled to 273 K and a solution of chlorodiphenylphosphine (7.0 ml, 39 mmol) in hexanes (25 ml) was added dropwise. The reaction mixture decolourized and a light-brown precipitate was formed. After stirring for 16 h at room temperature, the reaction mixture was hydrolyzed with brine (50 ml). The water layer was removed and the organic layer was dried over MgSO4. The solvent was removed and the residue purified by chromatography (cyclohexane), followed by crystallization from dichloromethane–ethanol (Ratio?). Yield 7.91 g (73%) of colourless crystals of (I), m.p. 432–433 K. Spectroscopic analysis: 1H NMR (500 MHz, C6D6, δ, p.p.m.): 0.26 (s, 6H), 0.90 (s, 9H), 6.63 (d, 2H, J = 7.7 Hz), 6.71 (t, 2H, J = 7.7 Hz), 6.89 (d, 2H, J = 7.7 Hz), 7.1 (bs, 12H), 7.5 (bs, 8H); 13C NMR (125 MHz, C6D6, δ, p.p.m.): 0.9 (CH3), 21.7 (C), 28.7 (CH3), 124.3 (CH), 125.0 (CH), 128.2 (C), 128.3 (C), 128.4 (C), 129.4(CH), 129.8 (m, CH), 136.8 (m, CH), 138.4 (C), 139.0 (m, C); 31P NMR (81 MHz, CDCl3, δ, p.p.m.): −16.6; MS (FAB+ LR): m/z (%) = 666 (M)+, (20); exact mass (FAB+ HR): 665.2425 (M)+, calculated for C42H41ONSiP2: 665.2433.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.93–0.96 Å, and were refined as riding, with Uiso(H) = 1.5Ueq(C) for methyl groups and 1.2Ueq(C) for others; the methyl groups were allowed to rotate but not to tip.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the labelling of all non-H atoms. H atoms have been omitted for clarity. Displacement ellipsoids are shown at the 30% probability level.
10-(tert-Butyldimethylsilyl)-4,6-bis(diphenylphosphino)phenoxazine top
Crystal data top
C42H41NOP2SiF(000) = 1408
Mr = 665.79Dx = 1.191 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ynCell parameters from 32114 reflections
a = 18.8748 (18) Åθ = 3.2–25.0°
b = 10.8973 (10) ŵ = 0.18 mm1
c = 19.1042 (15) ÅT = 291 K
β = 109.139 (5)°Block, light yellow
V = 3712.2 (6) Å30.20 × 0.10 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2229 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.0°, θmin = 3.2°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 2222
ω scansk = 1212
32114 measured reflectionsl = 2221
6468 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 0.99 w = [exp{4.2(sinθ/λ)2}]/[σ2(Fo2)]
where P = 0.333Fo2 + 0.667Fc2
6468 reflections(Δ/σ)max < 0.001
429 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C42H41NOP2SiV = 3712.2 (6) Å3
Mr = 665.79Z = 4
Monoclinic, P21/nMo Kα radiation
a = 18.8748 (18) ŵ = 0.18 mm1
b = 10.8973 (10) ÅT = 291 K
c = 19.1042 (15) Å0.20 × 0.10 × 0.08 mm
β = 109.139 (5)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2229 reflections with I > 2σ(I)
32114 measured reflectionsRint = 0.041
6468 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 0.99Δρmax = 0.15 e Å3
6468 reflectionsΔρmin = 0.18 e Å3
429 parameters
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
xyzUiso*/Ueq
P10.22098 (5)0.52970 (8)0.04010 (5)0.0790 (3)
P20.39917 (5)0.74126 (8)0.02815 (5)0.0782 (3)
Si0.09955 (5)0.93450 (8)0.22507 (5)0.0861 (3)
O0.23899 (11)0.73431 (17)0.05367 (10)0.0728 (5)
N0.15712 (15)0.8019 (2)0.19669 (12)0.0734 (7)
C10.00025 (17)0.8857 (3)0.26512 (18)0.1211 (13)
H1A0.00610.83420.30740.182*
H1B0.03160.95680.28000.182*
H1C0.01450.84090.22860.182*
C20.1240 (2)1.0205 (3)0.29780 (17)0.1259 (13)
H2A0.17411.05180.27760.189*
H2B0.08961.08750.31490.189*
H2C0.12080.96670.33850.189*
C30.10914 (19)1.0389 (3)0.14562 (18)0.0855 (10)
C40.0563 (2)1.1502 (3)0.1719 (2)0.1463 (16)
H4A0.00541.12200.19220.219*
H4B0.06971.19430.20920.219*
H4C0.06081.20340.13060.219*
C50.1884 (2)1.0894 (3)0.1120 (2)0.1487 (17)
H5A0.18941.14840.07440.223*
H5B0.20341.12820.15000.223*
H5C0.22221.02350.09050.223*
C60.0875 (2)0.9749 (3)0.08525 (18)0.1187 (12)
H6A0.12310.91120.06370.178*
H6B0.03840.93970.10600.178*
H6C0.08731.03330.04770.178*
C110.16019 (16)0.5645 (3)0.05439 (15)0.0653 (8)
C120.09783 (18)0.4940 (3)0.09427 (19)0.0769 (9)
H120.08380.42730.07140.092*
C130.05708 (17)0.5215 (3)0.16640 (19)0.0806 (9)
H130.01670.47220.19200.097*
C140.07552 (18)0.6219 (3)0.20154 (16)0.0759 (9)
H140.04750.63960.25040.091*
C150.13545 (18)0.6958 (3)0.16409 (18)0.0686 (8)
C160.17685 (18)0.6632 (3)0.09248 (19)0.0670 (8)
C210.17432 (18)0.3967 (3)0.06417 (15)0.0718 (9)
C220.20826 (17)0.2839 (3)0.06824 (15)0.0781 (9)
H220.25310.27890.05800.094*
C230.1788 (2)0.1783 (3)0.08682 (18)0.0895 (10)
H230.20280.10330.08840.107*
C240.1128 (2)0.1860 (3)0.10315 (18)0.0983 (11)
H240.09190.11570.11590.118*
C250.07842 (19)0.2967 (4)0.10051 (19)0.0990 (11)
H250.03400.30130.11160.119*
C260.10822 (19)0.4010 (3)0.08185 (18)0.0915 (10)
H260.08420.47580.08090.110*
C310.1943 (2)0.6486 (3)0.09347 (19)0.0756 (9)
C320.1369 (2)0.7304 (3)0.06577 (19)0.0992 (11)
H320.10830.72550.01590.119*
C330.1198 (3)0.8195 (4)0.1085 (3)0.1285 (16)
H330.08050.87370.08750.154*
C340.1601 (3)0.8282 (4)0.1812 (3)0.1363 (18)
H340.14880.88850.21030.164*
C350.2171 (3)0.7485 (5)0.2115 (2)0.1246 (16)
H350.24460.75400.26170.150*
C360.2345 (2)0.6585 (4)0.1681 (2)0.1059 (12)
H360.27370.60440.18960.127*
C410.35536 (18)0.7928 (2)0.06731 (16)0.0690 (8)
C420.39207 (18)0.8436 (3)0.11312 (19)0.0795 (9)
H420.44360.85620.09430.095*
C430.3539 (2)0.8756 (3)0.18563 (19)0.0851 (10)
H430.38000.90870.21490.102*
C440.2777 (2)0.8586 (3)0.21488 (17)0.0811 (9)
H440.25290.87670.26450.097*
C450.23726 (19)0.8148 (3)0.17097 (18)0.0705 (9)
C460.27755 (19)0.7808 (3)0.09856 (17)0.0676 (8)
C510.39031 (16)0.8775 (3)0.07991 (17)0.0723 (9)
C520.40297 (18)0.9960 (4)0.06191 (18)0.0929 (10)
H520.41521.00990.01920.111*
C530.3981 (2)1.0952 (3)0.1055 (3)0.1059 (12)
H530.40781.17400.09240.127*
C540.3789 (2)1.0769 (4)0.1675 (2)0.1044 (12)
H540.37531.14310.19680.125*
C550.36526 (19)0.9610 (5)0.1862 (2)0.1046 (12)
H550.35220.94810.22850.126*
C560.37075 (16)0.8619 (4)0.1426 (2)0.0873 (10)
H560.36100.78330.15610.105*
C610.49927 (17)0.7405 (3)0.03746 (17)0.0705 (8)
C620.5531 (2)0.8103 (3)0.08804 (17)0.0753 (9)
H620.53850.87170.11420.090*
C630.6286 (2)0.7904 (3)0.10043 (19)0.0893 (10)
H630.66420.83720.13550.107*
C640.6517 (2)0.7016 (3)0.0611 (2)0.0900 (10)
H640.70250.68860.06940.108*
C650.5990 (2)0.6327 (3)0.0096 (2)0.0914 (10)
H650.61390.57300.01750.110*
C660.5239 (2)0.6523 (3)0.00184 (17)0.0834 (10)
H660.48860.60500.03690.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0682 (6)0.0870 (6)0.0849 (6)0.0005 (5)0.0292 (5)0.0145 (5)
P20.0736 (6)0.0800 (6)0.0802 (6)0.0107 (5)0.0241 (5)0.0105 (5)
Si0.0979 (8)0.0771 (6)0.0799 (7)0.0011 (6)0.0245 (6)0.0018 (5)
O0.0713 (14)0.0893 (14)0.0589 (13)0.0156 (12)0.0229 (12)0.0043 (11)
N0.077 (2)0.0775 (17)0.0626 (17)0.0054 (15)0.0185 (15)0.0091 (13)
C10.097 (3)0.102 (3)0.126 (3)0.006 (2)0.014 (2)0.024 (2)
C20.197 (4)0.094 (3)0.096 (3)0.035 (3)0.060 (3)0.027 (2)
C30.088 (3)0.089 (2)0.088 (2)0.017 (2)0.039 (2)0.007 (2)
C40.184 (5)0.090 (3)0.179 (4)0.022 (3)0.080 (3)0.015 (3)
C50.123 (3)0.171 (4)0.170 (4)0.071 (3)0.073 (3)0.093 (3)
C60.140 (3)0.119 (3)0.110 (3)0.026 (3)0.058 (3)0.028 (2)
C110.063 (2)0.064 (2)0.071 (2)0.0031 (17)0.0248 (18)0.0030 (18)
C120.085 (3)0.069 (2)0.082 (2)0.001 (2)0.034 (2)0.0017 (19)
C130.077 (2)0.074 (2)0.087 (3)0.0118 (19)0.022 (2)0.009 (2)
C140.076 (2)0.082 (2)0.065 (2)0.001 (2)0.0173 (19)0.008 (2)
C150.076 (2)0.071 (2)0.055 (2)0.0052 (19)0.0166 (19)0.0001 (18)
C160.063 (2)0.068 (2)0.074 (2)0.0094 (18)0.028 (2)0.0084 (19)
C210.070 (2)0.070 (2)0.080 (2)0.0089 (18)0.0302 (19)0.0058 (17)
C220.074 (2)0.088 (2)0.075 (2)0.002 (2)0.0283 (18)0.0013 (19)
C230.101 (3)0.072 (3)0.098 (3)0.006 (2)0.035 (2)0.002 (2)
C240.110 (3)0.077 (3)0.118 (3)0.022 (2)0.050 (3)0.005 (2)
C250.092 (3)0.082 (3)0.145 (3)0.009 (2)0.069 (2)0.002 (2)
C260.086 (3)0.074 (2)0.129 (3)0.003 (2)0.055 (2)0.004 (2)
C310.077 (2)0.080 (2)0.068 (3)0.014 (2)0.021 (2)0.005 (2)
C320.129 (3)0.097 (3)0.079 (3)0.010 (3)0.044 (2)0.008 (2)
C330.183 (5)0.114 (3)0.101 (3)0.025 (3)0.064 (4)0.004 (3)
C340.200 (6)0.116 (4)0.118 (5)0.031 (4)0.087 (4)0.026 (3)
C350.145 (5)0.163 (5)0.069 (3)0.053 (4)0.039 (3)0.012 (3)
C360.105 (3)0.137 (4)0.076 (3)0.024 (3)0.030 (3)0.003 (3)
C410.072 (2)0.071 (2)0.067 (2)0.0087 (17)0.0268 (19)0.0057 (16)
C420.079 (2)0.079 (2)0.082 (3)0.0115 (18)0.029 (2)0.0071 (19)
C430.097 (3)0.085 (2)0.082 (3)0.014 (2)0.041 (2)0.015 (2)
C440.092 (3)0.090 (2)0.062 (2)0.010 (2)0.027 (2)0.0069 (18)
C450.077 (3)0.075 (2)0.061 (2)0.0063 (19)0.024 (2)0.0015 (17)
C460.073 (2)0.075 (2)0.060 (2)0.0093 (18)0.028 (2)0.0063 (17)
C510.062 (2)0.085 (3)0.068 (2)0.0054 (17)0.0201 (18)0.0173 (18)
C520.115 (3)0.085 (3)0.092 (3)0.001 (2)0.051 (2)0.010 (2)
C530.112 (3)0.089 (3)0.127 (3)0.004 (2)0.052 (3)0.013 (3)
C540.089 (3)0.115 (4)0.115 (4)0.023 (2)0.041 (2)0.002 (3)
C550.097 (3)0.136 (4)0.093 (3)0.012 (3)0.048 (2)0.013 (3)
C560.071 (2)0.103 (3)0.092 (3)0.0025 (19)0.033 (2)0.013 (2)
C610.074 (2)0.066 (2)0.070 (2)0.008 (2)0.0223 (19)0.0048 (18)
C620.075 (3)0.075 (2)0.082 (3)0.010 (2)0.033 (2)0.0021 (18)
C630.076 (3)0.100 (3)0.088 (3)0.014 (2)0.022 (2)0.004 (2)
C640.070 (3)0.100 (3)0.105 (3)0.005 (2)0.036 (2)0.009 (2)
C650.089 (3)0.088 (3)0.104 (3)0.001 (2)0.040 (3)0.004 (2)
C660.088 (3)0.074 (2)0.087 (3)0.011 (2)0.027 (2)0.004 (2)
Geometric parameters (Å, º) top
P1—C311.819 (3)C24—C251.363 (4)
P1—C211.831 (3)C24—H240.9300
P1—C111.833 (3)C25—C261.366 (4)
P2—C511.822 (3)C25—H250.9300
P2—C411.826 (3)C26—H260.9300
P2—C611.839 (3)C31—C321.369 (4)
P1—P24.1453 (12)C31—C361.382 (4)
Si—N1.783 (2)C32—C331.373 (4)
Si—C21.855 (3)C32—H320.9300
Si—C31.858 (3)C33—C341.349 (5)
Si—C11.863 (3)C33—H330.9300
O—C461.390 (3)C34—C351.355 (5)
O—C161.399 (3)C34—H340.9300
N—C151.435 (3)C35—C361.392 (5)
N—C451.436 (3)C35—H350.9300
C1—H1A0.9600C36—H360.9300
C1—H1B0.9600C41—C421.396 (4)
C1—H1C0.9600C41—C461.398 (3)
C2—H2A0.9600C42—C431.380 (4)
C2—H2B0.9600C42—H420.9300
C2—H2C0.9600C43—C441.375 (4)
C3—C61.514 (4)C43—H430.9300
C3—C51.524 (4)C44—C451.390 (4)
C3—C41.546 (4)C44—H440.9300
C4—H4A0.9600C45—C461.393 (4)
C4—H4B0.9600C51—C561.374 (4)
C4—H4C0.9600C51—C521.377 (4)
C5—H5A0.9600C52—C531.385 (4)
C5—H5B0.9600C52—H520.9300
C5—H5C0.9600C53—C541.362 (4)
C6—H6A0.9600C53—H530.9300
C6—H6B0.9600C54—C551.360 (4)
C6—H6C0.9600C54—H540.9300
C11—C161.391 (3)C55—C561.390 (4)
C11—C121.403 (3)C55—H550.9300
C12—C131.373 (3)C56—H560.9300
C12—H120.9300C61—C621.379 (3)
C13—C141.387 (4)C61—C661.390 (4)
C13—H130.9300C62—C631.383 (4)
C14—C151.381 (3)C62—H620.9300
C14—H140.9300C63—C641.381 (4)
C15—C161.381 (4)C63—H630.9300
C21—C221.376 (3)C64—C651.370 (4)
C21—C261.396 (4)C64—H640.9300
C22—C231.374 (4)C65—C661.378 (4)
C22—H220.9300C65—H650.9300
C23—C241.382 (4)C66—H660.9300
C23—H230.9300
C31—P1—C21100.32 (14)C25—C24—H24120.0
C31—P1—C11101.88 (15)C23—C24—H24120.0
C21—P1—C11102.34 (14)C24—C25—C26120.9 (3)
C51—P2—C41101.49 (14)C24—C25—H25119.5
C51—P2—C61103.04 (15)C26—C25—H25119.5
C41—P2—C61102.27 (15)C25—C26—C21120.8 (3)
N—Si—C2111.17 (14)C25—C26—H26119.6
N—Si—C3111.19 (14)C21—C26—H26119.6
C2—Si—C3108.74 (15)C32—C31—C36116.4 (3)
N—Si—C1109.08 (13)C32—C31—P1125.2 (3)
C2—Si—C1107.61 (16)C36—C31—P1118.3 (3)
C3—Si—C1108.96 (15)C31—C32—C33122.8 (4)
C46—O—C16113.1 (2)C31—C32—H32118.6
C15—N—C45110.4 (2)C33—C32—H32118.6
C15—N—Si123.6 (2)C34—C33—C32119.9 (4)
C45—N—Si119.6 (2)C34—C33—H33120.1
Si—C1—H1A109.5C32—C33—H33120.1
Si—C1—H1B109.5C33—C34—C35119.7 (5)
H1A—C1—H1B109.5C33—C34—H34120.1
Si—C1—H1C109.5C35—C34—H34120.1
H1A—C1—H1C109.5C34—C35—C36120.4 (5)
H1B—C1—H1C109.5C34—C35—H35119.8
Si—C2—H2A109.5C36—C35—H35119.8
Si—C2—H2B109.5C31—C36—C35120.8 (4)
H2A—C2—H2B109.5C31—C36—H36119.6
Si—C2—H2C109.5C35—C36—H36119.6
H2A—C2—H2C109.5C42—C41—C46115.9 (3)
H2B—C2—H2C109.5C42—C41—P2126.3 (3)
C6—C3—C5108.6 (3)C46—C41—P2117.8 (2)
C6—C3—C4107.6 (3)C43—C42—C41121.8 (3)
C5—C3—C4107.0 (3)C43—C42—H42119.1
C6—C3—Si111.2 (2)C41—C42—H42119.1
C5—C3—Si112.6 (2)C44—C43—C42120.4 (3)
C4—C3—Si109.6 (2)C44—C43—H43119.8
C3—C4—H4A109.5C42—C43—H43119.8
C3—C4—H4B109.5C43—C44—C45120.6 (3)
H4A—C4—H4B109.5C43—C44—H44119.7
C3—C4—H4C109.5C45—C44—H44119.7
H4A—C4—H4C109.5C44—C45—C46117.5 (3)
H4B—C4—H4C109.5C44—C45—N123.5 (3)
C3—C5—H5A109.5C46—C45—N119.0 (3)
C3—C5—H5B109.5O—C46—C45119.0 (3)
H5A—C5—H5B109.5O—C46—C41117.4 (3)
C3—C5—H5C109.5C45—C46—C41123.7 (3)
H5A—C5—H5C109.5C56—C51—C52116.9 (3)
H5B—C5—H5C109.5C56—C51—P2118.1 (3)
C3—C6—H6A109.5C52—C51—P2125.1 (3)
C3—C6—H6B109.5C51—C52—C53122.0 (3)
H6A—C6—H6B109.5C51—C52—H52119.0
C3—C6—H6C109.5C53—C52—H52119.0
H6A—C6—H6C109.5C54—C53—C52119.8 (4)
H6B—C6—H6C109.5C54—C53—H53120.1
C16—C11—C12115.6 (3)C52—C53—H53120.1
C16—C11—P1120.0 (2)C55—C54—C53119.5 (4)
C12—C11—P1124.4 (3)C55—C54—H54120.3
C13—C12—C11121.3 (3)C53—C54—H54120.3
C13—C12—H12119.3C54—C55—C56120.4 (4)
C11—C12—H12119.3C54—C55—H55119.8
C12—C13—C14120.7 (3)C56—C55—H55119.8
C12—C13—H13119.6C51—C56—C55121.4 (3)
C14—C13—H13119.6C51—C56—H56119.3
C15—C14—C13120.1 (3)C55—C56—H56119.3
C15—C14—H14119.9C62—C61—C66117.4 (3)
C13—C14—H14119.9C62—C61—P2124.3 (3)
C16—C15—C14117.7 (3)C66—C61—P2117.8 (3)
C16—C15—N119.2 (3)C61—C62—C63121.0 (3)
C14—C15—N123.1 (3)C61—C62—H62119.5
C15—C16—C11124.4 (3)C63—C62—H62119.5
C15—C16—O119.1 (3)C64—C63—C62120.5 (3)
C11—C16—O116.4 (3)C64—C63—H63119.8
C22—C21—C26116.9 (3)C62—C63—H63119.8
C22—C21—P1117.9 (3)C65—C64—C63119.4 (3)
C26—C21—P1125.1 (3)C65—C64—H64120.3
C23—C22—C21122.8 (3)C63—C64—H64120.3
C23—C22—H22118.6C64—C65—C66119.7 (3)
C21—C22—H22118.6C64—C65—H65120.1
C22—C23—C24118.6 (3)C66—C65—H65120.1
C22—C23—H23120.7C65—C66—C61122.0 (3)
C24—C23—H23120.7C65—C66—H66119.0
C25—C24—C23119.9 (3)C61—C66—H66119.0
C2—Si—N—C15155.8 (2)P1—C31—C32—C33179.2 (3)
C3—Si—N—C1582.9 (3)C31—C32—C33—C340.5 (6)
C1—Si—N—C1537.3 (3)C32—C33—C34—C350.3 (7)
C2—Si—N—C4555.1 (3)C33—C34—C35—C360.5 (7)
C3—Si—N—C4566.2 (3)C32—C31—C36—C350.7 (5)
C1—Si—N—C45173.6 (2)P1—C31—C36—C35179.4 (3)
N—Si—C3—C659.1 (3)C34—C35—C36—C310.0 (6)
C2—Si—C3—C6178.2 (2)C51—P2—C41—C4293.8 (3)
C1—Si—C3—C661.2 (3)C61—P2—C41—C4212.5 (3)
N—Si—C3—C563.0 (3)C51—P2—C41—C4686.4 (2)
C2—Si—C3—C559.7 (3)C61—P2—C41—C46167.4 (2)
C1—Si—C3—C5176.7 (3)C46—C41—C42—C432.3 (4)
N—Si—C3—C4177.9 (2)P2—C41—C42—C43177.6 (2)
C2—Si—C3—C459.4 (3)C41—C42—C43—C440.4 (5)
C1—Si—C3—C457.7 (3)C42—C43—C44—C453.2 (5)
C31—P1—C11—C1675.7 (2)C43—C44—C45—C464.5 (4)
C21—P1—C11—C16179.2 (2)C43—C44—C45—N176.2 (3)
C31—P1—C11—C12107.4 (3)C15—N—C45—C44144.6 (3)
C21—P1—C11—C123.9 (3)Si—N—C45—C4462.5 (3)
C16—C11—C12—C130.6 (4)C15—N—C45—C4634.7 (3)
P1—C11—C12—C13176.4 (2)Si—N—C45—C46118.1 (3)
C11—C12—C13—C141.5 (4)C16—O—C46—C4535.0 (3)
C12—C13—C14—C150.0 (5)C16—O—C46—C41146.2 (3)
C13—C14—C15—C162.2 (4)C44—C45—C46—O178.7 (3)
C13—C14—C15—N179.2 (3)N—C45—C46—O0.6 (4)
C45—N—C15—C1634.5 (4)C44—C45—C46—C412.5 (4)
Si—N—C15—C16117.0 (3)N—C45—C46—C41178.1 (3)
C45—N—C15—C14144.1 (3)C42—C41—C46—O177.9 (2)
Si—N—C15—C1464.4 (3)P2—C41—C46—O2.2 (4)
C14—C15—C16—C113.2 (4)C42—C41—C46—C450.8 (4)
N—C15—C16—C11178.2 (3)P2—C41—C46—C45179.1 (2)
C14—C15—C16—O178.5 (2)C41—P2—C51—C56138.9 (2)
N—C15—C16—O0.2 (4)C61—P2—C51—C56115.5 (2)
C12—C11—C16—C151.8 (4)C41—P2—C51—C5242.3 (3)
P1—C11—C16—C15178.9 (2)C61—P2—C51—C5263.3 (3)
C12—C11—C16—O179.8 (2)C56—C51—C52—C531.4 (5)
P1—C11—C16—O2.7 (3)P2—C51—C52—C53177.4 (3)
C46—O—C16—C1535.4 (3)C51—C52—C53—C541.2 (5)
C46—O—C16—C11146.1 (3)C52—C53—C54—C550.4 (6)
C31—P1—C21—C22147.1 (2)C53—C54—C55—C560.1 (6)
C11—P1—C21—C22108.2 (2)C52—C51—C56—C551.0 (5)
C31—P1—C21—C2630.1 (3)P2—C51—C56—C55177.9 (2)
C11—P1—C21—C2674.6 (3)C54—C55—C56—C510.3 (5)
C26—C21—C22—C231.6 (5)C51—P2—C61—C6214.5 (3)
P1—C21—C22—C23179.1 (2)C41—P2—C61—C62119.6 (3)
C21—C22—C23—C241.0 (5)C51—P2—C61—C66174.5 (2)
C22—C23—C24—C250.1 (5)C41—P2—C61—C6669.5 (2)
C23—C24—C25—C260.0 (5)C66—C61—C62—C631.9 (4)
C24—C25—C26—C210.7 (5)P2—C61—C62—C63169.2 (2)
C22—C21—C26—C251.5 (5)C61—C62—C63—C641.4 (5)
P1—C21—C26—C25178.7 (3)C62—C63—C64—C650.2 (5)
C21—P1—C31—C3298.9 (3)C63—C64—C65—C660.4 (5)
C11—P1—C31—C326.2 (3)C64—C65—C66—C610.0 (5)
C21—P1—C31—C3681.0 (3)C62—C61—C66—C651.2 (4)
C11—P1—C31—C36173.9 (3)P2—C61—C66—C65170.4 (2)
C36—C31—C32—C330.9 (5)

Experimental details

Crystal data
Chemical formulaC42H41NOP2Si
Mr665.79
Crystal system, space groupMonoclinic, P21/n
Temperature (K)291
a, b, c (Å)18.8748 (18), 10.8973 (10), 19.1042 (15)
β (°) 109.139 (5)
V3)3712.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.20 × 0.10 × 0.08
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
32114, 6468, 2229
Rint0.041
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.079, 0.99
No. of reflections6468
No. of parameters429
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.18

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

 

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