Synthesis of 6-arylpyrimido[4,5-<i>e</i>]indolizine-2,4(1<i>H</i>,3<i>H</i>)-diones through InCl<sub>3</sub>-catalyzed cycloisomerization.
Figueira de Abreu, Ruben Manuel; Villinger, Alexander; Ehlers, Peter; Langer, Peter; Organic & biomolecular chemistry 23 (2025) 5215–5223; doi:10.1039/d5ob00436e

data_7160528
_publ_section_title
;
 Synthesis of
 6-arylpyrimido[4,5-<i>e</i>]indolizine-2,4(1<i>H</i>,3<i>H</i>)-diones
 through InCl<sub>3</sub>-catalyzed cycloisomerization.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5215
_journal_page_last               5223
_journal_paper_doi               10.1039/d5ob00436e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.123(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5685(10)
_cell_length_b                   7.0647(4)
_cell_length_c                   16.3807(11)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.50
_cell_measurement_theta_min      3.28
_cell_volume                     1513.72(17)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            65236
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.996
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS-2016/2; Sheldrick, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0732P)^2^+0.4982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4157
_reflns_number_total             4820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00436e2.cif
_cod_data_source_block           is_c8dd1
_cod_depositor_comments          'Adding full bibliography for 7160528.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160528
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              8051
_shelx_hkl_checksum              45688