Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones.
Maddox, Sean M.; Dawson, Gregory A.; Rochester, Nicholas C.; Ayonon, Arianna B.; Moore, Curtis E.; Rheingold, Arnold L.; Gustafson, Jeffrey L.; ACS catalysis 8 (2018) 5443–5447; doi:10.1021/acscatal.8b00906

data_4515653
_publ_section_title
;
 Enantioselective Synthesis of Biaryl Atropisomers via the Addition of
 Thiophenols into Aryl-Naphthoquinones.
;
_journal_issue                   6
_journal_name_full               'ACS catalysis'
_journal_page_first              5443
_journal_page_last               5447
_journal_paper_doi               10.1021/acscatal.8b00906
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H18 Cl F3 O2 S'
_chemical_formula_sum            'C25 H18 Cl F3 O2 S'
_chemical_formula_weight         474.90
_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     dual
_audit_creation_date             2017-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8069(3)
_cell_length_b                   7.8369(2)
_cell_length_c                   35.3156(11)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.152
_cell_measurement_theta_min      5.783
_cell_volume                     2160.68(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         70.146
_diffrn_reflns_theta_min         5.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.883
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.4267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0864 before and 0.0639 after correction. The Ratio of minimum to maximum transmission is 0.8174. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0079P)^2^+5.4057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4005
_reflns_number_total             4116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b00906_si_003.cif
_cod_data_source_block           gustof02
_cod_database_code               4515653
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.625
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C12(H12), C4(H4), C5(H5), C13(H13), C14(H14), C20(H20),
 C3(H3), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              57927
_shelx_hkl_checksum              21147
_olex2_submission_special_instructions 'No special instructions were received'