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_7250388
_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_absolute_configuration unk
_chemical_formula_moiety         'C17 H15 N3'
_chemical_formula_sum            'C17 H15 N3'
_chemical_formula_weight         261.329
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-26
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1053(13)
_cell_length_b                   13.209(3)
_cell_length_c                   16.219(4)
_cell_measurement_reflns_used    2668
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.128
_cell_measurement_theta_min      2.511
_cell_volume                     1308.0(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8026
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9967
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.99
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8050.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             552.313
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2144
_refine_diff_density_min         -0.2557
_refine_diff_density_rms         0.0477
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.1(18)
_refine_ls_d_res_high            0.7702
_refine_ls_d_res_low             10.2422
_refine_ls_goodness_of_fit_ref   0.8525
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8525
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.994
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              21
_reflns_limit_l_min              -20
_reflns_number_gt                2250
_reflns_number_total             2984
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5gc01245g2.cif
_cod_data_source_block           240831b_0m
_cod_depositor_comments
'Adding full bibliography for 7250388--7250391.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7250388
_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.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C9(H9a,H9b,H9c)
;
_olex2_submission_special_instructions 'No special instructions were received'