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_7158779
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H24 N4 O4'
_chemical_formula_weight         384.43
_chemical_name_systematic
1-methyl-4-(3-methyl-2-oxo-1-phenylimidazolidin-4-yl)-3-phenyl-1,3-dihydro-2H-imidazol-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-05 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5996(6)
_cell_length_b                   7.2670(3)
_cell_length_c                   42.5196(18)
_cell_measurement_reflns_used    9113
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.40
_cell_volume                     3893.1(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            44052
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         1.916
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5304
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.7110.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plank
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 3311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         8472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0593P)^2^+2.8097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7806
_reflns_number_total             8472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01031c2.cif
_cod_data_source_block           almir2_0m_a
_cod_database_code               7158779
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. 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, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B), O5(H5A,H5B), O3(H3C,H3D), O6(H6C,H6D)
2.b Ternary CH refined with riding coordinates:
 C11B(H11B), C11A(H11A)
2.c Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D)
2.d Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C17A(H17A), C20A(H20A), C16B(H16B), C20B(H20B), C17B(H17B),
 C6B(H6B), C18B(H18B), C16A(H16A), C19B(H19B), C6A(H6A), C18A(H18A), C19A(H19A),
  C10B(H10B), C10A(H10A), C7A(H7A), C3A(H3A), C9A(H9A), C9B(H9B), C8A(H8A),
 C7B(H7B), C8B(H8B)
2.e Idealised Me refined as rotating group:
 C14B(H14D,H14E,H14F), C4A(H4AA,H4AB,H4AC), C14A(H14A,H14B,H14C), C4B(H4BA,
 H4BB,H4BC)
;
_shelx_res_checksum              22068
_olex2_submission_special_instructions 'No special instructions were received'