Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides.
Liu, Xu-Teng; Zhang, Ya-Qian; Han, Xue-Yu; Sun, Shi-Ping; Zhang, Qing-Wei; Journal of the American Chemical Society 141 (2019) 16584–16589; doi:10.1021/jacs.9b08734

data_4127961
_publ_section_title
;
 Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16584
_journal_page_last               16589
_journal_paper_doi               10.1021/jacs.9b08734
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H23 O P'
_chemical_formula_sum            'C23 H23 O P'
_chemical_formula_weight         346.38
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.268(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5889(5)
_cell_length_b                   7.8356(7)
_cell_length_c                   22.0624(17)
_cell_measurement_reflns_used    4109
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      4.01
_cell_volume                     965.93(14)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      287(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6261
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        65.062
_diffrn_reflns_theta_max         65.062
_diffrn_reflns_theta_min         4.008
_exptl_absorpt_coefficient_mu    1.298
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6469
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1353P)^2^+0.3733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1980
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2480
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08734_si_002.cif
_cod_data_source_block           t_a
_cod_database_code               4127961
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.781
_shelx_estimated_absorpt_t_max   0.819
_shelx_res_checksum              33225
_shelx_hkl_checksum              13414