Ruthenium(II)-catalyzed regioselective direct C4‒ and C5‒diamidation of indoles and mechanistic studies
Devkota, Shreedhar; Kim, Suyeon; Yoo, Seok Yeol; Mohandoss, Sonaimuthu; Baik, Mu-Hyun; Lee, Yong Rok; Chemical Science  (2021) –; doi:10.1039/D1SC02138A

data_1564243
_publ_section_title
;
 Ruthenium(II)-catalyzed regioselective direct C4-- and C5--diamidation of
 indoles and mechanistic studies
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02138A
_journal_year                    2021
_chemical_formula_moiety         'C35 H25 N3 O3'
_chemical_formula_sum            'C35 H25 N3 O3'
_chemical_formula_weight         535.58
_chemical_melting_point          536
_chemical_name_systematic
N,N'-(3-Formyl-1,2-diphenyl-1H-indole-4,5-diyl)dibenzamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-03-13 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_c                   24.7785(12)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.18
_cell_volume                     5546.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
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_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            223588
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_min         2.192
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/EtOAc'
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0505P)^2^+2.5484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5784
_reflns_number_total             6880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02138a2.cif
_cod_data_source_block           SD_736
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1564243
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              50818
_shelx_hkl_checksum              86723