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_7250389
_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         '2(C15 H13 N3 Se)'
_chemical_formula_sum            'C30 H26 N6 Se2'
_chemical_formula_weight         628.49
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-09-16
_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                 113.010(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.961(3)
_cell_length_b                   9.6920(17)
_cell_length_c                   16.557(3)
_cell_measurement_reflns_used    5352
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.206
_cell_measurement_theta_min      2.404
_cell_volume                     2800.6(8)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         1.167
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0954 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.6203. 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    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0576P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4297
_reflns_number_total             6438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01245g2.cif
_cod_data_source_block           240915bbb_a
_cod_depositor_comments
'Adding full bibliography for 7250388--7250391.cif.'
_cod_original_cell_volume        2800.6(9)
_cod_database_code               7250389
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.617
_shelx_estimated_absorpt_t_min   0.591
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), N005(H005), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00B,H00C), C00W(H00D,H00F,H00G)
;
_shelx_res_checksum              75504
_shelx_hkl_checksum              48396
_olex2_submission_special_instructions 'No special instructions were received'