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_4515654
_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         'C26 H21 F3 O2 S'
_chemical_formula_sum            'C26 H21 F3 O2 S'
_chemical_formula_weight         454.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.144(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7702(4)
_cell_length_b                   7.7862(4)
_cell_length_c                   17.9926(8)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      2.49
_cell_volume                     1071.54(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi 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  0.0443
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9800
_diffrn_reflns_point_group_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.304
_diffrn_reflns_theta_min         2.495
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.759
_exptl_absorpt_correction_T_max  0.5210
_exptl_absorpt_correction_T_min  0.4165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.7994.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.072(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0365P)^2^+0.2130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.485
_reflns_Friedel_fraction_full    0.572
_reflns_Friedel_fraction_max     0.568
_reflns_number_gt                3027
_reflns_number_total             3155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b00906_si_002.cif
_cod_data_source_block           gustof01r_0m_a
_cod_database_code               4515654
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.639
_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:
 C7(H7), C22(H22), C13(H13), C15(H15), C20(H20), C21(H21), C4(H4), C16(H16),
 C14(H14), C19(H19), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              46736
_shelx_hkl_checksum              22438
_olex2_submission_special_instructions 'No special instructions were received'