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_4034621
_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 H23 Cl N O4 P S'
_chemical_formula_sum            'C19 H23 Cl N O4 P S'
_chemical_formula_weight         427.86
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_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                120
_cell_formula_units_Z            6
_cell_length_a                   12.8491(3)
_cell_length_b                   12.8491(3)
_cell_length_c                   22.5713(5)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    253.0(1)
_cell_measurement_theta_max      80.01
_cell_measurement_theta_min      6.89
_cell_volume                     3227.25(13)
_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      253.0(1)
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.975
_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  0.0518
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            42140
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         80.672
_diffrn_reflns_theta_min         6.892
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_exptl_absorpt_coefficient_mu    3.384
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.2686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.990
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0502P)^2^+0.3297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4506
_reflns_number_total             4588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00945_si_001.cif
_cod_data_source_block           2b_253K
_cod_original_cell_volume        3227.25(17)
_cod_database_code               4034621
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.135
_shelx_estimated_absorpt_t_max   0.534
_shelx_res_checksum              75774
_shelx_hkl_checksum              23523