Substituent-controlled regioselective arylation of carbazoles using dual catalysis.
Shahid, M.; Muthuraja, Perumal; Gopinath, Purushothaman; Organic & biomolecular chemistry 22 (2024) 753–758; doi:10.1039/d3ob01827j

data_7159733
_publ_section_title
;
 Substituent-controlled regioselective arylation of carbazoles using dual
 catalysis.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              753
_journal_page_last               758
_journal_paper_doi               10.1039/d3ob01827j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H17 N3 O2'
_chemical_formula_sum            'C24 H17 N3 O2'
_chemical_formula_weight         379.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-08-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7425(10)
_cell_length_b                   13.5862(11)
_cell_length_c                   10.3411(7)
_cell_measurement_reflns_used    5318
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.55
_cell_measurement_theta_min      2.20
_cell_volume                     1775.8(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            42328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.081
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_min         2.201
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7368
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0966 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.9522.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0292P)^2^+0.9354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2421
_reflns_number_total             3158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01827j2.cif
_cod_data_source_block           mo_gp_sm_212_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7159731--7159734.cif.'
_cod_database_code               7159733
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              26094
_olex2_submission_special_instructions 'No special instructions were received'