Transition Metal-Catalyzed Regioselective Functionalization of Carbazoles and Indolines with Maleimides
Cho, Eun Hee; Akhtar, Muhammad Saeed; Aslam, Mohammad; Thombal, Raju S.; Li, Xin; Shim, Jae-Jin; Lee, Yong Rok; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01077A

data_7158811
_publ_section_title
;
 Transition Metal-Catalyzed Regioselective Functionalization of Carbazoles
 and Indolines with Maleimides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01077A
_journal_year                    2022
_chemical_formula_moiety         'C22 H15 Br N4 O2'
_chemical_formula_sum            'C22 H15 Br N4 O2'
_chemical_formula_weight         447.29
_chemical_melting_point          514
_chemical_name_systematic
3-(5-Bromo-1-(pyrimidin-2-yl)-1H-indol-2-yl)-1-phenylpyrrolidine-2,5-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-08 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.315(11)
_cell_length_b                   7.025(5)
_cell_length_c                   17.444(11)
_cell_measurement_reflns_used    9228
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.37
_cell_volume                     2093(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41083
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_min         2.367
_exptl_absorpt_coefficient_mu    1.988
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate'
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+1.8044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3651
_reflns_number_total             5224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01077a2.cif
_cod_data_source_block           eh_141a_a_sq
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158811
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.640
_shelx_estimated_absorpt_t_max   0.768
_shelx_res_checksum              2067
_shelx_fab_checksum              98792