Tandem copper catalyzed regioselective <i>N</i>-arylation-amidation: synthesis of angularly fused dihydroimidazoquinazolinones and the anticancer agent TIC10/ONC201.
Honnanayakanavar, Jyoti M.; Nanubolu, Jagadeesh Babu; Suresh, Surisetti; Organic & biomolecular chemistry 19 (2021) 8497–8501; doi:10.1039/d1ob01561c

data_7158288
_publ_section_title
;
 Tandem copper catalyzed regioselective <i>N</i>-arylation-amidation:
 synthesis of angularly fused dihydroimidazoquinazolinones and the
 anticancer agent TIC10/ONC201.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8497
_journal_page_last               8501
_journal_paper_doi               10.1039/d1ob01561c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H16 N4 O'
_chemical_formula_sum            'C17 H16 N4 O'
_chemical_formula_weight         292.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-03 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                82.153(3)
_cell_angle_beta                 79.194(3)
_cell_angle_gamma                71.829(3)
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.251
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_cell_volume                     1443.1(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.209
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
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_exptl_crystal_description       block
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'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.340
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_refine_diff_density_max         0.216
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0445P)^2^+0.4552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3927
_reflns_number_total             5081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01561c2.cif
_cod_data_source_block           KA825_0m
_cod_depositor_comments
'Adding full bibliography for 7158288--7158291.cif.'
_cod_database_code               7158288
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              18538