Diastereoselective intramolecular cyclization/Povarov reaction cascade for the one-pot synthesis of polycyclic quinolines.
Kuznetsova, E. A.; Smolobochkin, A. V.; Rizbayeva, T. S.; Gazizov, A. S.; Voronina, J. K.; Lodochnikova, O. A.; Gerasimova, D. P.; Dobrynin, A. B.; Syakaev, V. V.; Shurpik, D. N.; Stoikov, I. I.; Burilov, A. R.; Pudovik, M. A.; Sinyashin, O. G.; Organic & biomolecular chemistry 20 (2022) 5515–5519; doi:10.1039/d2ob01031c

data_7158783
_publ_section_title
;
 Diastereoselective intramolecular cyclization/Povarov reaction cascade
 for the one-pot synthesis of polycyclic quinolines.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5515
_journal_page_last               5519
_journal_paper_doi               10.1039/d2ob01031c
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C32 H26 Br2 N4 O2'
_chemical_formula_weight         658.39
_chemical_name_systematic
(3aS,3bR,11bS)-3,5-bis(4-bromobenzyl)-1-phenyl-1,3a,3b,4,5,11b-hexahydro-2H-diimidazo[1,5-a:4',5'-c]quinoline-2,6(3H)-dione
_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-2014/7
_audit_update_record
;
2022-04-08 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                91.874(2)
_cell_angle_beta                 106.844(2)
_cell_angle_gamma                112.114(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6635(7)
_cell_length_b                   11.4629(8)
_cell_length_c                   14.1743(10)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.39
_cell_volume                     1374.29(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.943
_diffrn_reflns_theta_min         1.521
_exptl_absorpt_coefficient_mu    2.987
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.102
_refine_diff_density_max         1.194
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.814
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0842P)^2^+3.8551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4984
_reflns_number_total             6591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01031c2.cif
_cod_data_source_block           SAB1_0m_a
_cod_database_code               7158783
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.485
_shelx_estimated_absorpt_t_max   0.750
_shelx_res_checksum              47148