Pd-catalyzed efficient synthesis of 3-formylindole derivatives with diaziridinone.
Wang, Jianjun; Yang, E.; Liu, Wei; Zhang, Shiwei; Shi, Yian; Organic & biomolecular chemistry 23 (2025) 5006–5015; doi:10.1039/d5ob00246j

data_7160513
_publ_section_title
;
 Pd-catalyzed efficient synthesis of 3-formylindole derivatives with
 diaziridinone.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5006
_journal_page_last               5015
_journal_paper_doi               10.1039/d5ob00246j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H29 N O2'
_chemical_formula_sum            'C24 H29 N O2'
_chemical_formula_weight         363.48
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-23
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2024-07-05 deposited with the CCDC.	2025-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   31.5114(3)
_cell_length_b                   31.5114(3)
_cell_length_c                   9.2754(2)
_cell_measurement_reflns_used    6858
_cell_measurement_temperature    293
_cell_measurement_theta_max      116.174
_cell_measurement_theta_min      5.659
_cell_volume                     9210.2(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.1971
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            51855
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.112
_diffrn_reflns_theta_min         2.804
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.3813
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.049
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2531
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00246j2.cif
_cod_data_source_block           cu_d8v23455_0m
_cod_depositor_comments
'Adding full bibliography for 7160513--7160514.cif.'
_cod_original_cell_volume        9210.2(3)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7160513
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.922
_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: 
 C19(H19) 
2.b Secondary CH2 refined with riding coordinates: 
 C20(H20A,H20B), C22(H22A,H22B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), 
 C14(H14) 
2.d Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B, 
 H23C), C24(H24A,H24B,H24C) 
;
_shelx_res_checksum              723
_shelx_fab_checksum              33888
_olex2_submission_special_instructions 'No special instructions were received'