Asymmetric Library Synthesis of P-Chiral t-Butyl-Substituted Secondary and Tertiary Phosphine Oxides.
Li, Shi-Guang; Yuan, Minglei; Topic, Filip; Han, Zhengxu S.; Senanayake, Chris H.; Tsantrizos, Youla S.; The Journal of organic chemistry 84 (2019) 7291–7302; doi:10.1021/acs.joc.9b00945

data_4034622
_publ_section_title
;
 Asymmetric Library Synthesis of P-Chiral t-Butyl-Substituted Secondary
 and Tertiary Phosphine Oxides.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7291
_journal_page_last               7302
_journal_paper_doi               10.1021/acs.joc.9b00945
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H25 Cl N O4 P S'
_chemical_formula_sum            'C19 H25 Cl N O4 P S'
_chemical_formula_weight         429.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1288(12)
_cell_length_b                   16.100(3)
_cell_length_c                   22.181(4)
_cell_measurement_reflns_used    6582
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      79.72
_cell_measurement_theta_min      3.39
_cell_volume                     2188.7(7)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15841
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         80.561
_diffrn_reflns_theta_min         3.392
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_exptl_absorpt_coefficient_mu    3.327
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3664
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.733
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(14)
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0673P)^2^+0.5519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4010
_reflns_number_total             4605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00945_si_001.cif
_cod_data_source_block           3_RT
_cod_database_code               4034622
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.194
_shelx_estimated_absorpt_t_max   0.862
_shelx_res_checksum              50701
_shelx_hkl_checksum              75550