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_4515655
_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         'C23 H15 F3 O4 S, 0.7(C1 Cl3 D1)'
_chemical_formula_sum            'C23.7 H15 Cl2.1 D0.7 F3 O4 S'
_chemical_formula_weight         528.67
_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
_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                   9.3182(4)
_cell_length_b                   10.5061(5)
_cell_length_c                   24.8751(12)
_cell_measurement_reflns_used    2206
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.018
_cell_measurement_theta_min      2.334
_cell_volume                     2435.2(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12216
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         2.334
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.4910
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0481 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.8937.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       plate
_exptl_crystal_F_000             1074
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.305
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0694
_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^)+(0.1043P)^2^+1.9241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3743
_reflns_number_total             5163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b00906_si_004.cif
_cod_data_source_block           gust01_0m_a
_cod_original_formula_sum        'C23.70 H15 Cl2.10 D0.70 F3 O4 S'
_cod_database_code               4515655
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: Cl3(0.7) Cl2(0.7) Cl1(0.7) C24(0.7) D24(0.7)
3.a Ternary CH refined with riding coordinates:
 C24(D24)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C18(H18), C3(H3A), C10(H10), C6(H6), C21(H21), C19(H19), C4(H4A),
 C13(H13), C12(H12), C11(H11), C20(H20), C5(H5)
3.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_shelx_res_checksum              39906
_shelx_hkl_checksum              25937
_olex2_submission_special_instructions 'No special instructions were received'