One-pot three-component synthesis of benzo[<i>h</i>]isoquinolin-3-ones <i>via</i> rhodium(III)-catalyzed C-H activation.
Song, Weihong; Jiang, Xiaomei; Yu, Weiguo; Xiang, ZiWei; Organic & biomolecular chemistry 23 (2025) 9587–9591; doi:10.1039/d5ob01222h

data_7160752
_publ_section_title
;
 One-pot three-component synthesis of benzo[<i>h</i>]isoquinolin-3-ones
 <i>via</i> rhodium(III)-catalyzed C-H activation.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9587
_journal_page_last               9591
_journal_paper_doi               10.1039/d5ob01222h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_chemical_name_common            Benzo[h]isoquinolin-3-ones
_chemical_name_systematic
'ethyl 2-cyclohexyl-3-oxo-2,3-dihydrobenzo[h]isoquinoline-4-carboxylate'
_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             2025-07-17
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-07-18 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.568(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7981(12)
_cell_length_b                   12.8375(14)
_cell_length_c                   12.4903(13)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      3.87
_cell_volume                     1830.9(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29650
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.281
_diffrn_reflns_theta_min         3.871
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.8445.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0460P)^2^+0.4144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2886
_reflns_number_total             3347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01222h2.cif
_cod_data_source_block           t1
_cod_depositor_comments          'Adding full bibliography for 7160752.cif.'
_cod_database_code               7160752
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C2(H2A,H2B), C9(H9A,H9B), C10(H10A,
 H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C19(H19), C22(H22), C15(H15), C20(H20), C21(H21), C16(H16)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              59826
_olex2_submission_special_instructions 'No special instructions were received'