Asymmetric synthesis of dihydrocarbazoles through Friedel-Crafts alkylation/annulation sequential reaction of indoles
Hu, Linfeng; Cao, Weidi; Wang, Kaixuan; Liu, Xiaohua; Feng, Xiaoming; Chemical Communications  (2021) –; doi:10.1039/D1CC05099K

data_7129229
_publ_section_title
;
 Asymmetric synthesis of dihydrocarbazoles through Friedel-Crafts
 alkylation/annulation sequential reaction of indoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05099K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 N3 O3'
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-09 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.2220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9940(4)
_cell_length_b                   7.9399(2)
_cell_length_c                   18.0476(5)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      80.51
_cell_measurement_theta_min      3.32
_cell_volume                     2016.14(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40560
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         81.381
_diffrn_reflns_theta_min         2.609
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7970
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       flake
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EA, Hexane'
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 2812 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8393
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+1.2515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                7234
_reflns_number_total             8393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05099k2.cif
_cod_data_source_block           hlf004
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129229
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              89791
_shelx_fab_checksum              39914