Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.
Gribble, Jr, Michael W; Pirnot, Michael T.; Bandar, Jeffrey S.; Liu, Richard Y.; Buchwald, Stephen L.; Journal of the American Chemical Society 139 (2017) 2192–2195; doi:10.1021/jacs.6b13029

data_4125589
_publ_section_title
;
 Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of
 Vinylarenes and Vinyl Heterocycles.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2192
_journal_page_last               2195
_journal_paper_doi               10.1021/jacs.6b13029
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H26 N2 O Si'
_chemical_formula_weight         374.55
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.6050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5002(2)
_cell_length_b                   12.7386(3)
_cell_length_c                   16.6006(4)
_cell_measurement_reflns_used    9321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.03
_cell_measurement_theta_min      2.66
_cell_volume                     2008.88(8)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            78682
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.073
_diffrn_reflns_theta_min         2.662
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    1.136
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.219
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 3539 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Classic Flack x: 0.061(21)
 Hooft y: 0.047(5)
 100% probability for correct assignement by Bijvoet-pair analysis
;
_refine_ls_abs_structure_Flack   0.041(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7602
_refine_ls_number_restraints     291
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0527P)^2^+0.4746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7561
_reflns_number_total             7602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13029_si_002.cif
_cod_data_source_block           X16217
_cod_depositor_comments          'Adding full bibliography for 4125589.cif.'
_cod_database_code               4125589
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.720
_shelx_estimated_absorpt_t_max   0.789
_shelx_res_checksum              8953
_shelx_hkl_checksum              13582