Nonepimerizing Alkylation of H-P Species to Stereospecifically Generate P-Stereogenic Phosphine Oxides: A Shortcut to Bidentate Tertiary Phosphine Ligands.
Nie, Shao-Zhen; Zhou, Zhong-Yang; Wang, Ji-Ping; Yan, Hui; Wen, Jing-Hong; Ye, Jing-Jing; Cui, Yun-Yao; Zhao, Chang-Qiu; The Journal of organic chemistry 82 (2017) 9425–9434; doi:10.1021/acs.joc.7b01413

data_4033093
_publ_section_title
;
 Nonepimerizing Alkylation of H-P Species to Stereospecifically Generate
 P-Stereogenic Phosphine Oxides: A Shortcut to Bidentate Tertiary
 Phosphine Ligands.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9425
_journal_page_last               9434
_journal_paper_doi               10.1021/acs.joc.7b01413
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration R
_chemical_formula_sum            'C23 H31 O P'
_chemical_formula_weight         354.45
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7510(2)
_cell_length_b                   8.5852(4)
_cell_length_c                   41.6195(17)
_cell_measurement_reflns_used    4980
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1890
_cell_measurement_theta_min      8.3360
_cell_volume                     2054.90(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            11598
_diffrn_reflns_theta_full        67.23
_diffrn_reflns_theta_max         67.23
_diffrn_reflns_theta_min         5.26
_exptl_absorpt_coefficient_mu    1.221
_exptl_absorpt_correction_T_max  0.8673
_exptl_absorpt_correction_T_min  0.8574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.3322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                3511
_reflns_number_total             3680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01413_si_002.cif
_cod_data_source_block           exp_7626
_cod_original_cell_volume        2054.91(14)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4033093