A regioselective C7 bromination and C7 palladium-catalyzed Suzuki–Miyaura cross-coupling arylation of 4-substituted NH-free indazoles
Boujdi, Khalid; El Brahmi, Nabil; Graton, Jérôme; Dubreuil, Didier; Collet, Sylvain; Mathé-Allainmat, Monique; Akssira, Mohamed; Lebreton, Jacques; El Kazzouli, Saïd; RSC Advances 11 (2021) 7107–7114; doi:10.1039/D0RA08598G

data_7242251
_publ_section_title
;
 A regioselective C7 bromination and C7 palladium-catalyzed
 Suzuki--Miyaura cross-coupling arylation of 4-substituted NH-free
 indazoles
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              7107
_journal_page_last               7114
_journal_paper_doi               10.1039/D0RA08598G
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C14 H12 Br N3 O2 S'
_chemical_formula_sum            'C14 H12 Br N3 O2 S'
_chemical_formula_weight         366.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-10T16:07:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-08-02 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.002(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3718(4)
_cell_length_b                   5.0528(2)
_cell_length_c                   19.9057(6)
_cell_measurement_reflns_used    3065
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.68
_cell_measurement_theta_min      3.02
_cell_volume                     1444.63(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5496
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         71.842
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    5.306
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.60932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.024
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+1.0485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0
_reflns_number_gt                2528
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra08598g2.cif
_cod_data_source_block           kbn22-150k
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242251
_shelx_res_checksum              23933