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_7159731
_publ_section_title
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 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         '2(C23 H14 F3 N3)'
_chemical_formula_sum            'C46 H28 F6 N6'
_chemical_formula_weight         778.74
_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
_audit_creation_date             2023-06-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-06 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.097(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4774(17)
_cell_length_b                   12.0444(11)
_cell_length_c                   16.5411(15)
_cell_measurement_reflns_used    4971
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.237
_cell_measurement_theta_min      1.088
_cell_volume                     3728.3(6)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  Bruker_D8_venture
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25773
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_min         2.011
_exptl_absorpt_coefficient_mu    0.104
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         7429
_refine_ls_number_restraints     360
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0699P)^2^+0.4690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4971
_reflns_number_total             7429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01827j2.cif
_cod_data_source_block           mo_gpsm892_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7159731--7159734.cif.'
_cod_database_code               7159731
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C24-F1B \\sim C24-F2B \\sim C24-F3B \\sim C24-F4B \\sim C24-F5B \\sim C24-F6B
 with sigma of 0.02
 F1B-F2B \\sim F2B-F3B \\sim F3B-F1B \\sim F4B-F5B \\sim F5B-F6B \\sim F6B-F4B
 with sigma of 0.04
 C21-F1B \\sim C21-F2B \\sim C21-F3B \\sim C21-F4B \\sim C21-F5B \\sim C21-F6B
 with sigma of 0.1
 C47-F1A \\sim C47-F2A \\sim C47-F3A \\sim C47-F4A \\sim C47-F5A \\sim C47-F6A
 with sigma of 0.02
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.04
 C7-F1A \\sim C7-F2A \\sim C7-F3A \\sim C7-F4A \\sim C7-F5A \\sim C7-F6A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C21 \\sim C24 \\sim F1B \\sim F2B \\sim F3B \\sim F4B \\sim F5B \\sim F6B:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C7 \\sim C47 \\sim F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C21, C24, F1B, F2B, F3B, F4B, F5B, F6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C47, F1A, F2A, F3A, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(2)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C34(H34), C35(H35), C36(H36), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
;
_shelx_res_checksum              36403
_olex2_submission_special_instructions 'No special instructions were received'