Visible-light-induced selenium-mediated cascade cyclization of 2-isocyanobenzonitriles with secondary amines to access indole-fused polycyclics
Xu, Dongping; Jin, Lizhen; Huang, Mengya; Zhang, Wu; Green Chemistry 27 (2025) 6880–6886; doi:10.1039/D5GC01245G

data_7250390
_publ_section_title
;
 Visible-light-induced selenium-mediated cascade cyclization of
 2-isocyanobenzonitriles with secondary amines to access indole-fused
 polycyclics
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              6880
_journal_page_last               6886
_journal_paper_doi               10.1039/D5GC01245G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C H Cl3, C25 H23 N3'
_chemical_formula_sum            'C26 H24 Cl3 N3'
_chemical_formula_weight         484.83
_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             2024-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.812(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.095(3)
_cell_length_b                   13.262(3)
_cell_length_c                   14.744(3)
_cell_measurement_reflns_used    2665
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      19.37
_cell_measurement_theta_min      2.22
_cell_volume                     2475.4(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      297.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16249
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.407
_diffrn_reflns_theta_max         24.407
_diffrn_reflns_theta_min         1.608
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6315
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8470.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0885P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1875
_reflns_number_total             3924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01245g2.cif
_cod_data_source_block           240110b_0m
_cod_depositor_comments
'Adding full bibliography for 7250388--7250391.cif.'
_cod_original_cell_volume        2475.6(9)
_cod_database_code               7250390
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(C26)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C26(H26)
3.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C15(H15), C17(H17), C18(H18), C13(H13), C14(H14), C2(H2),
 C5(H5), C4(H4), C3(H3)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              90083
_shelx_hkl_checksum              86351
_olex2_submission_special_instructions 'No special instructions were received'