The design of second generation MOP-phosphonites: efficient chiral hydrosilylation of functionalised styrenes.
Fleming, James T.; Ficks, Arne; Waddell, Paul G.; Harrington, Ross W.; Higham, Lee J.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 1886–1890; doi:10.1039/c5dt04475h

data_7037441
_publ_section_title
;
 The design of second generation MOP-phosphonites: efficient chiral
 hydrosilylation of functionalised styrenes.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1886
_journal_page_last               1890
_journal_paper_doi               10.1039/c5dt04475h
_journal_volume                  45
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H25 O3 P'
_chemical_formula_sum            'C33 H25 O3 P'
_chemical_formula_weight         500.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-02 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7963(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.57860(7)
_cell_length_b                   16.52575(9)
_cell_length_c                   14.80544(8)
_cell_measurement_reflns_used    35462
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.7940
_cell_measurement_theta_min      2.9820
_cell_volume                     2575.04(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -2.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   84.0000 -159.1169 26

  2 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   82.0000  -17.4601 26

  3 omega  -99.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  125.0000  -60.0000 81

  4 omega   -3.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905 -125.0000 -180.0000 99

  5 omega   22.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   38.0000  120.0000 93

  6 omega   67.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   38.0000   30.0000 43

  7 omega   16.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   38.0000   30.0000 45

  8 omega   16.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   38.0000  -90.0000 100

  9 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000 -119.6867 27

 10 omega   17.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000 -119.6867 26

 11 omega   20.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -163.2920 52

 12 omega  108.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   84.4926 25

 13 omega   21.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000   12.2847 30

 14 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -163.2920 26

 15 omega   20.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   84.4926 27

 16 omega   93.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000   39.6355 27

 17 omega   29.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000 -102.0116 32

 18 omega   28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  -40.8772 26

 19 omega   28.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000   39.6355 25

 20 omega  109.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  108.8742 30

 21 omega   28.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  108.8742 25

 22 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000 -102.0116 26

 23 omega   32.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  145.5481 27

 24 omega   33.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000 -144.2922 25

 25 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000  -72.6295 26

 26 omega   93.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  145.5481 26

 27 omega   33.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   77.9365 33

 28 omega   33.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000   -9.2834 26

 29 omega   36.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   79.0000  -41.5012 48

 30 omega   37.00   63.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   78.0000 -171.8373 26

 31 omega   53.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   58.0000   32.4916 25

 32 omega  129.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 42

 33 omega   74.00  162.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000 -180.0000 88

 34 omega   60.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 36

 35 omega   86.00  153.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 67

 36 omega   20.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -180.0000 61

 37 omega   60.00  151.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 91

 38 omega  104.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -90.0000 35

 39 omega   61.00  141.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 80

 40 omega   72.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -90.0000 26

 41 omega   82.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  105.7499 50

 42 omega   60.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 26

 43 omega   60.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 87

 44 omega   24.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  105.7499 45

 45 omega  104.00  129.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 25

 46 omega   60.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 31

 47 omega   58.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -98.6286 59

 48 omega   98.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 73

 49 omega  130.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 42

 50 omega   60.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 27

 51 omega   14.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -98.6286 31

 52 omega   60.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 112

 53 omega   16.00   62.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 46

 54 omega   87.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 26

 55 omega  125.00  151.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 26

 56 omega   47.00  133.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000    3.8576 86

 57 omega   35.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -30.0000 49

 58 omega   29.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -180.0000 51

 59 omega   60.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 39

 60 omega  100.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 70

 61 omega   98.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -37.0657 32

 62 omega   27.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 49

 63 omega   60.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 26

 64 omega  131.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 37

 65 omega    9.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -37.0657 68

 66 omega   60.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 54

 67 omega  113.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  150.0000 31

 68 omega   21.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 52

 69 omega   66.00  156.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   56.0000  169.8886 90

 70 omega   73.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  150.0000 27

 71 omega   60.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 87

 72 omega   29.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -156.0000  101.0000 46

 73 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   82.0000  -17.4601 26

 74 omega  -99.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  125.0000 -150.0000 81

 75 omega   16.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -58.9287 114

 76 omega   29.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000   19.5624 111

 77 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000   -9.2834 113

 78 omega   32.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000  124.5195 114

 79 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  167.3421 113

 80 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000 -144.2922 113

 81 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   77.9365 113

 82 omega   32.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   78.0000  -72.6295 113
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0719855000
_diffrn_orient_matrix_UB_12      0.0450577000
_diffrn_orient_matrix_UB_13      -0.0701608000
_diffrn_orient_matrix_UB_21      0.0569372000
_diffrn_orient_matrix_UB_22      -0.0807377000
_diffrn_orient_matrix_UB_23      -0.0285550000
_diffrn_orient_matrix_UB_31      -0.1140359000
_diffrn_orient_matrix_UB_32      -0.0118779000
_diffrn_orient_matrix_UB_33      -0.0721177000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            71384
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.999
_diffrn_reflns_theta_min         3.000
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         9138
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.2858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                8606
_reflns_number_total             9138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt04475h2.cif
_cod_data_source_block           ljh150068_fa
_cod_depositor_comments
'Adding full bibliography for 7037441--7037444.cif.'
_cod_database_code               7037441
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C33 H25 O3 P1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-C12B \\sim O1-C12A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12A) = Uanis(C12B)
Uanis(C11A) = Uanis(C11B)
Uanis(C16A) = Uanis(C16B)
Uanis(C15A) = Uanis(C15B)
Uanis(C14A) = Uanis(C14B)
Uanis(C13A) = Uanis(C13B)
4. Same fragment restrains
{C11A, C12A, C13A, C14A, C15A, C16A} sigma for 1-2: 0.02, 1-3: 0.02
as
{C11B, C12B, C13B, C14B, C15B, C16B}
5. Others
 Fixed Sof: C11A(0.57603) H11A(0.57603) C12A(0.57603) C13A(0.57603)
 H13A(0.57603) C14A(0.57603) H14A(0.57603) C15A(0.57603) H15A(0.57603)
 C16A(0.57603) H16A(0.57603) C11B(0.42397) H11B(0.42397) C12B(0.42397)
 C13B(0.42397) H13B(0.42397) C14B(0.42397) H14B(0.42397) C15B(0.42397)
 H15B(0.42397) C16B(0.42397) H16B(0.42397)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C5(H5), C5'(H5'), C6(H6), C6'(H6'),
 C7(H7), C7'(H7'), C8(H8), C8'(H8'), C11'(H11'), C13'(H13'), C14'(H14'),
 C15'(H15'), C16'(H16'), C20(H20), C20'(H20'), C21(H21), C21'(H21'), C22(H22),
 C22'(H22'), C23(H23), C23'(H23'), C24(H24), C24'(H24'), C25(H25), C25'(H25'),
 C28(H28), C28'(H28'), C30(H30), C30'(H30'), C31(H31), C31'(H31'), C32(H32),
 C32'(H32'), C33(H33), C33'(H33'), C11A(H11A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C11B(H11B), C13B(H13B), C14B(H14B), C15B(H15B),
 C16B(H16B)
6.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              39030
_olex2_submission_special_instructions 'No special instructions were received'