Chemo- and Stereoselective Alcoholysis of Binaphthyl Phosphonothioates: Straightforward Access to both Stereoisomers of Biologically Relevant P-Stereogenic Phosphonothioates.
Kuwabara, Kazuma; Maekawa, Yuuki; Minoura, Mao; Maruyama, Toshifumi; Murai, Toshiaki; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00687

data_4038576
_publ_section_title
;
 Chemo- and Stereoselective Alcoholysis of Binaphthyl Phosphonothioates:
 Straightforward Access to both Stereoisomers of Biologically Relevant
 P-Stereogenic Phosphonothioates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00687
_journal_year                    2020
_chemical_formula_sum            'C14 H25 O7 P S'
_chemical_formula_weight         368.37
_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   geom
_atom_sites_solution_primary     'SHELXT-2014 (Sheldrick 2014)'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9034(17)
_cell_length_b                   11.952(2)
_cell_length_c                   16.993(3)
_cell_measurement_reflns_used    178
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      10.11
_cell_measurement_theta_min      2.22
_cell_volume                     1808.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX3'
_computing_publication_material  'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Dectris PILATUS-CdTe'
_diffrn_measurement_method       'Phi scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4118
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        14.305
_diffrn_reflns_theta_max         15.505
_diffrn_reflns_theta_min         1.207
_diffrn_source                   'BL02B1 SPring-8'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.077(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0376P)^2^+0.4268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4117
_reflns_number_total             4143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00687_si_002.cif
_cod_data_source_block           191201_06_TM01_0m_a
_cod_database_code               4038576
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.999
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              67128
_shelx_hkl_checksum              53965