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_7158777
_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_moiety         'C20 H18 Cl2 N4 O2'
_chemical_formula_sum            'C20 H18 Cl2 N4 O2'
_chemical_formula_weight         417.27
_chemical_name_systematic
(3aS,3bR,11bS)-9-chloro-3-(3-chlorophenyl)-1,5-dimethyl-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_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                92.661(3)
_cell_angle_beta                 109.964(3)
_cell_angle_gamma                107.892(3)
_cell_formula_units_Z            4
_cell_length_a                   10.8202(9)
_cell_length_b                   12.3589(10)
_cell_length_c                   15.5997(14)
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.25
_cell_volume                     1839.0(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 1.000
_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  0.0718
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.058
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1794 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.9082.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       plank
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         8012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0432P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5302
_reflns_number_total             8012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01031c2.cif
_cod_data_source_block           dp9_0m_a
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C6.67 H6 Cl0.67 N1.33 O0.67'
_cod_original_formula_weight         139.09
_cod_original_formula_moiety         '0.333(C20 H18 Cl2 N4 O2)'
_cod_original_formula_units_Z            12
_cod_database_code               7158777
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.875
_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
2.a Ternary CH refined with riding coordinates:
 C2B(H2B), C3A(H3A), C2A(H2A), C11A(H11A), C3B(H3B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C20B(H20B), C18B(H18B), C10A(H10A), C10B(H10B), C20A(H20A), C17B(H17B),
 C6A(H6A), C6B(H6B), C18A(H18A), C7B(H7B), C8B(H8B), C7A(H7A), C17A(H17A),
 C8A(H8A)
2.d Idealised Me refined as rotating group:
 C4B(H4BA,H4BB,H4BC), C14B(H14D,H14E,H14F), C14A(H14A,H14B,H14C), C4A(H4AA,
 H4AB,H4AC)
;
_shelx_res_checksum              7873
_olex2_submission_special_instructions 'No special instructions were received'