Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C–H/N–H coupling for the synthesis of N–H indoles
Kim, Youyoung; Kim, Dongwook; Chang, Sukbok; Chemical Communications  (2021) –; doi:10.1039/D1CC05882G

data_7129202
_publ_section_title
;
 Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative
 C--H/N--H coupling for the synthesis of N--H indoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05882G
_journal_year                    2021
_chemical_formula_sum            'C19 H24 Ir N'
_chemical_formula_weight         458.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-03 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.834(3)
_cell_length_b                   8.0960(16)
_cell_length_c                   14.131(3)
_cell_measurement_reflns_used    45870
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      34.080
_cell_measurement_theta_min      0.372
_cell_volume                     1697.1(6)
_computing_cell_refinement       HKL3000sm
_computing_data_collection       'PAL BL2D-SMDC Program'
_computing_data_reduction        HKL3000sm
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.650
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12196
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        22.955
_diffrn_reflns_theta_max         23.996
_diffrn_reflns_theta_min         2.301
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    6.224
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.031
_refine_diff_density_max         1.241
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0193
_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^)+(0.0291P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0497
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3272
_reflns_number_total             3480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05882g2.cif
_cod_data_source_block           PO19049_029
_cod_database_code               7129202
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.780
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              68548
_shelx_hkl_checksum              49205