Regio- and Enantioselective Friedel-Crafts Benzhydrylation of Indoles in Carbocyclic Ring with ortho-Quinomethanes: Access to Chiral Diarylindolylmethanes.
Chu, Ming-Ming; Chen, Xue-Yang; Wang, Yi-Feng; Qi, Suo-Suo; Jiang, Zhen-Hui; Xu, Dan-Qian; Xu, Zhen-Yuan; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03479

data_4038628
_publ_section_title
;
 Regio- and Enantioselective Friedel-Crafts Benzhydrylation of Indoles in
 Carbocyclic Ring with ortho-Quinomethanes: Access to Chiral
 Diarylindolylmethanes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03479
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H25 F6 N O9 S2'
_chemical_formula_weight         697.61
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.544(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.742(3)
_cell_length_b                   9.0469(19)
_cell_length_c                   26.924(6)
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      47.476
_cell_measurement_theta_min      4.676
_cell_volume                     3083.5(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.837
_diffrn_measured_fraction_theta_max 0.971
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.837
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9815
_diffrn_reflns_point_group_measured_fraction_full 0.705
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.905
_diffrn_reflns_theta_min         2.085
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.062
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
; 
 Flack x determined using 1683 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     835
_refine_ls_number_reflns         7860
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0878
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1503P)^2^+7.2359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2305
_refine_ls_wR_factor_ref         0.2687
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.553
_reflns_Friedel_fraction_max     0.646
_reflns_number_gt                5348
_reflns_number_total             7860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03479_si_002.cif
_cod_data_source_block           mo_dd19152_0m
_cod_original_cell_volume        3083.5(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038628
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              13453
_shelx_hkl_checksum              37573