Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)-ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis.
Zhang, Zong-Feng; Zhu, Dong-Xing; Chen, Wen-Wen; Xu, Bin; Xu, Ming-Hua; Organic letters 19 (2017) 2726–2729; doi:10.1021/acs.orglett.7b01070

data_1546217
_publ_section_title
;
 Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)-ones via
 One-Pot Asymmetric Rhodium/Palladium Relay Catalysis.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2726
_journal_page_last               2729
_journal_paper_doi               10.1021/acs.orglett.7b01070
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H15 F O2'
_chemical_formula_sum            'C21 H15 F O2'
_chemical_formula_weight         318.33
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-27
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5282)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.209(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2656(5)
_cell_length_b                   15.4462(11)
_cell_length_c                   8.1799(6)
_cell_measurement_reflns_used    5712
_cell_measurement_temperature    205
_cell_measurement_theta_max      70.16
_cell_measurement_theta_min      5.42
_cell_volume                     789.51(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      205
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7341
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        63.998
_diffrn_reflns_theta_max         63.998
_diffrn_reflns_theta_min         5.422
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1190 before and 0.0477 after correction. The Ratio of minimum to maximum transmission is 0.7957. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1070 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0600P)^2^+0.0520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                2394
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01070_si_002.cif
_cod_data_source_block           cu_2016891_0m
_cod_database_code               1546217
_shelx_shelxl_version_number     2014/7
_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:
 C10(H10), C14(H14), C11(H11), C17(H17), C20(H20), C16(H16), C4(H4), C1(H1),
 C12(H12), C19(H19), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'