Rhodium-catalyzed C-H activation and three-component tandem annulation leading to isoquinolones.
Liu, Xiao; Yan, Kelu; Wen, Jiangwei; Li, Qiuyun; Shang, Wenxu; Yu, Xinming; Wang, Xiu; Organic & biomolecular chemistry 23 (2025) 4694–4701; doi:10.1039/d5ob00419e

data_7160493
_publ_section_title
;
 Rhodium-catalyzed C-H activation and three-component tandem annulation
 leading to isoquinolones.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4694
_journal_page_last               4701
_journal_paper_doi               10.1039/d5ob00419e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_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_date             2024-08-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-08-03 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                99.451(4)
_cell_angle_beta                 100.327(3)
_cell_angle_gamma                107.469(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3081(8)
_cell_length_b                   8.5016(9)
_cell_length_c                   14.2301(15)
_cell_measurement_reflns_used    3466
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.863
_cell_measurement_theta_min      2.667
_cell_volume                     806.98(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0708
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.582
_exptl_absorpt_coefficient_mu    2.561
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.8215.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1536
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0246P)^2^+0.2399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1776
_reflns_number_total             4008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00419e2.cif
_cod_data_source_block           2-20240803
_cod_depositor_comments          'Adding full bibliography for 7160493.cif.'
_cod_database_code               7160493
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C1(H1), C18(H18), C14(H14), C15(H15), C9(H9), C3(H3),
 C17(H17), C2(H2)
;
_shelx_res_checksum              43079
_olex2_submission_special_instructions 'No special instructions were received'