Synthesis of Electron-Deficient Chiral Biphenols and Their Applica-tions in Catalytic Asymmetric Reactions.
Yasumoto, Kento; Kano, Taichi; Maruoka, Keiji; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01116

data_4038578
_publ_section_title
;
 Synthesis of Electron-Deficient Chiral Biphenols and Their Applica-tions
 in Catalytic Asymmetric Reactions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01116
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C18 H12 F8 I2 O4'
_chemical_formula_sum            'C18 H12 F8 I2 O4'
_chemical_formula_weight         698.09
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.4936(4)
_cell_length_b                   20.3829(9)
_cell_length_c                   10.7259(5)
_cell_measurement_reflns_used    20682
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      4.12
_cell_volume                     2294.16(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         4.338
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    22.354
_exptl_absorpt_correction_T_max  0.094
_exptl_absorpt_correction_T_min  0.033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320.00
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.85
_refine_diff_density_min         -0.59
_refine_ls_abs_structure_details
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3652
_reflns_number_total             4183
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo0c01116_si_002.cif
_cod_data_source_block           200222-R
_cod_original_cell_volume        2294.15(17)
_cod_database_code               4038578
_shelx_res_checksum              56634
_shelx_hkl_checksum              13134