Synthesis of pyrido[1,2-a]indol-6(7H)-ones via a visible light-photocatalyzed formal (4 + 2) cycloaddition of indole-derived bromides and alkenes or alkynes
Wei, Minghui; Liu, Chengkou; Wang, Chang-Sheng; Li, Yuguang; Qiu, Peng; Dong, Quanxiao; Yang, Zhao; Fang, Zheng; Guo, Kai; Green Chemistry 25 (2023) 2453–2457; doi:10.1039/D2GC04491A

data_7246425
_publ_section_title
;
 Synthesis of pyrido[1,2-a]indol-6(7H)-ones via a visible
 light-photocatalyzed formal (4 + 2) cycloaddition of indole-derived
 bromides and alkenes or alkynes
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2453
_journal_page_last               2457
_journal_paper_doi               10.1039/D2GC04491A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H19 N O'
_chemical_formula_sum            'C20 H19 N O'
_chemical_formula_weight         289.36
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bg1gb
_audit_creation_date             2021-06-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-03-14 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.972(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.949(7)
_cell_length_b                   10.787(3)
_cell_length_c                   11.392(3)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    193
_cell_measurement_theta_max      24.544
_cell_measurement_theta_min      2.628
_cell_volume                     3119.4(15)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.1009
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23973
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.143
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0773 after correction.
The Ratio of minimum to maximum transmission is 0.7327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         7121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1969
_refine_ls_R_factor_gt           0.0996
_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^)+(0.0318P)^2^+7.7967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1989
_refine_ls_wR_factor_ref         0.2444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3313
_reflns_number_total             7121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04491a2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7246425.cif.'
_cod_original_cell_volume        3119.6(16)
_cod_database_code               7246425
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.835(2)
 0.165(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C9(H9), C29(H29)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C35(H35),
  C36(H36), C37(H37), C38(H38), C39(H39)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C)
;
_shelx_res_checksum              21197
_olex2_submission_special_instructions 'No special instructions were received'