Site-Selective Rh-Catalyzed C-7 and C-6 Dual C-H Functionalization of Indolines: Synthesis of Functionalized Pyrrolocarbazoles.
Banerjee, Sonbidya; Vivek Kumar, Sundaravel; Punniyamurthy, Tharmalingam; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03180

data_4037824
_publ_section_title
;
 Site-Selective Rh-Catalyzed C-7 and C-6 Dual C-H Functionalization of
 Indolines: Synthesis of Functionalized Pyrrolocarbazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03180
_journal_year                    2020
_chemical_formula_moiety         'C32 H21 Br N4 O2 S'
_chemical_formula_sum            'C32 H21 Br N4 O2 S'
_chemical_formula_weight         605.50
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0736(9)
_cell_length_b                   14.0744(11)
_cell_length_c                   17.6490(13)
_cell_measurement_reflns_used    5432
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.67
_cell_measurement_theta_min      2.31
_cell_volume                     2750.7(4)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.2318
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            113515
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.040
_diffrn_reflns_theta_max         25.040
_diffrn_reflns_theta_min         1.851
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .15
_exptl_transmission_factor_max   0.786
_exptl_transmission_factor_min   0.623
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.835
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.835
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0429P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2350
_reflns_number_total             4863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03180_si_002.cif
_cod_data_source_block           SB-B-211B_0m_a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4037824
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              40977
_shelx_hkl_checksum              28568