Synthesis of dihydroindazolo[2,3-f]phenanthridin-5(6H)-ones via Rh(iii)-catalyzed C–H activation of 2-aryl indazoles and annulation with iodonium ylides
Liang, Jiazhi; Huang, Jian; Yang, Qin; Fu, Yang; Ding, Qiuping; Peng, Yiyuan; Green Chemistry 24 (2022) 8441–8446; doi:10.1039/D2GC03020A

data_7245574
_publ_section_title
;
 Synthesis of dihydroindazolo[2,3-f]phenanthridin-5(6H)-ones via
 Rh(iii)-catalyzed C--H activation of 2-aryl indazoles and annulation with
 iodonium ylides
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              8441
_journal_page_last               8446
_journal_paper_doi               10.1039/D2GC03020A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C23 H22 N2 O3, C H Cl3'
_chemical_formula_sum            'C24 H23 Cl3 N2 O3'
_chemical_formula_weight         493.79
_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_method           SHELXL-2018/3
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                92.796(4)
_cell_angle_beta                 92.658(3)
_cell_angle_gamma                95.189(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8190(2)
_cell_length_b                   9.8242(4)
_cell_length_c                   20.3104(10)
_cell_measurement_reflns_used    5633
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9430
_cell_measurement_theta_min      3.7650
_cell_volume                     1153.44(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0353
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12533
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.096
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_min         3.520
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       lump
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0559P)^2^+0.2380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3270
_reflns_number_total             4077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03020a2.cif
_cod_data_source_block           ljz-1_a
_cod_depositor_comments          'Adding full bibliography for 7245574.cif.'
_cod_database_code               7245574
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.927
_shelx_res_checksum              4609