Synthesis of 5-aryl-3,3′-bis-indolyl and bis-7-aza-indolyl methanone derivatives from 5-bromo-7-azaindoles via sequential methylenation using microwave irradiation, CAN oxidation, and Suzuki coupling reactions
Pavithra, Elavarasan; Kannadasan, Sathananthan; Shanmugam, Ponnusamy; RSC Advances 12 (2022) 30712–30721; doi:10.1039/D2RA05849A

data_7245732
_publ_section_title
;
 Synthesis of 5-aryl-3,3&#x2032;-bis-indolyl and bis-7-aza-indolyl
 methanone derivatives from 5-bromo-7-azaindoles via sequential
 methylenation using microwave irradiation, CAN oxidation, and Suzuki
 coupling reactions
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              30712
_journal_page_last               30721
_journal_paper_doi               10.1039/D2RA05849A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C17 H14 Br2 N4'
_chemical_formula_sum            'C17 H14 Br2 N4'
_chemical_formula_weight         434.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-20 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                100.609(3)
_cell_angle_beta                 105.510(3)
_cell_angle_gamma                95.703(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8514(7)
_cell_length_b                   8.4149(7)
_cell_length_c                   13.4259(12)
_cell_measurement_reflns_used    9566
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.66
_cell_volume                     829.71(13)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23280
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.493
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    4.889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.117
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0446P)^2^+0.7248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2985
_reflns_number_total             4105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05849a2.cif
_cod_data_source_block           EP3_66_010722_0m_a
_cod_database_code               7245732
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              80297