Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines.
Beaud, Rodolphe; Phipps, Robert J.; Gaunt, Matthew J.; Journal of the American Chemical Society 138 (2016) 13183–13186; doi:10.1021/jacs.6b09334

data_4131117
_publ_section_title
;
 Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides
 with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13183
_journal_page_last               13186
_journal_paper_doi               10.1021/jacs.6b09334
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H23 O P'
_chemical_formula_sum            'C18 H23 O P'
_chemical_formula_weight         286.33
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.642(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3113(3)
_cell_length_b                   11.2268(5)
_cell_length_c                   9.8191(4)
_cell_measurement_reflns_used    10640
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     851.63(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7771
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         4.036
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
Flack x determined using 1260 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.1818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                3197
_reflns_number_total             3582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09334_si_002.cif
_cod_data_source_block           mg_k3_0031
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131117
_cambridge_user_name             'Rudolphe Beaud'
_cambridge_user_crsid            rb755
_cambridge_supervisor_name       'Matthew Gaunt'
_cambridge_supervisor_crsid      mjg32
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             RB_2_049_ET
_cambridge_data_id               MG_K3_0031
_ccdc_publ_extra_info
;
_cambridge_sample_id RB_2_049_ET
_cambridge_data_id MG_K3_0031
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              29565
_shelx_hkl_checksum              99403