RhIII-Catalyzed C–H Heteroarylation and C–N Cleavage: Direct Access to C2-heteroarylated (NH)-indoles
Wang, Huaiwei; Liu, Zhen-Ang; Guan, Xiao; Su, Xiao-Wen; Dong, Yu-Tong; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00059B

data_7161058
_publ_section_title
;
 Rh<sup>III</sup>-catalyzed C-H heteroarylation and C-N cleavage: direct
 access to C2-heteroarylated (NH)-indoles.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2951
_journal_page_last               2962
_journal_paper_doi               10.1039/d6ob00059b
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C14 H11 Br N2 O'
_chemical_formula_sum            'C14 H11 Br N2 O'
_chemical_formula_weight         303.16
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2025-09-25
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.11.29 svn.rc9064207 for OlexSys, GUI svn.r7097)
;
_audit_update_record
;
2025-11-12 deposited with the CCDC.	2026-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.228(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.027(14)
_cell_length_b                   11.291(16)
_cell_length_c                   11.805(16)
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      25.014
_cell_measurement_theta_min      2.319
_cell_volume                     1262(3)
_computing_cell_refinement       'SAINT v6.02A (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.319
_diffrn_source_current           35.0
_diffrn_source_power             0.875
_diffrn_source_voltage           25.0
_exptl_absorpt_coefficient_mu    3.246
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      0.783
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0523
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1349
_reflns_number_total             2221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00059b2.cif
_cod_data_source_block           250919a
_cod_depositor_comments          'Adding full bibliography for 7161058.cif.'
_cod_database_code               7161058
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.737
_shelx_estimated_absorpt_t_min   0.697
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C10(H10), C12(H12), C3(H3), C2(H2A), C4(H4), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              73987
_shelx_hkl_checksum              34416
_olex2_submission_special_instructions 'No special instructions were received'