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_4038575
_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_moiety         'C27 H27 O3 P S'
_chemical_formula_sum            'C27 H27 O3 P S'
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_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
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9005(3)
_cell_length_b                   15.1026(4)
_cell_length_c                   17.3570(5)
_cell_measurement_reflns_used    9107
_cell_measurement_temperature    78(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      1.6
_cell_volume                     2333.14(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      78(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \f-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0209
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_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.787
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       Block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0465P)^2^+0.3734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5177
_reflns_number_total             5360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00687_si_001.cif
_cod_data_source_block           KK876
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038575
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              90407
_shelx_hkl_checksum              62048