One-pot asymmetric synthesis of a hexahydrophenanthridine scaffold containing five stereocenters via an organocatalytic quadruple-cascade reaction
Zhang, Xiao-Long; Feng, Kai-Xiang; Hu, Jian-Liang; Shen, Qiao-Yu; Huang, Wang-Sheng; Xia, Ai-Bao; Li, Chen; Xu, Dan-Qian; New Journal of Chemistry 45 (2021) 1168–1171; doi:10.1039/D0NJ03946B

data_7060168
_publ_section_title
;
 One-pot asymmetric synthesis of a hexahydrophenanthridine scaffold
 containing five stereocenters via an organocatalytic quadruple-cascade
 reaction
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1168
_journal_page_last               1171
_journal_paper_doi               10.1039/D0NJ03946B
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_compound_source        'organic synthesis'
_chemical_formula_moiety         'C28 H18 Cl3 F3 N2 O4'
_chemical_formula_sum            'C28 H18 Cl3 F3 N2 O4'
_chemical_formula_weight         609.79
_chemical_melting_point          298
_chemical_name_common
'tricyclic compounds containing trihydro-quinoline'
_chemical_name_systematic
'tricyclic compounds containing trihydro-quinoline'
_chemical_properties_physical    Oxygen-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-10-07 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3488(9)
_cell_length_b                   10.4603(11)
_cell_length_c                   29.766(3)
_cell_measurement_reflns_used    4813
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.750
_cell_measurement_theta_min      2.38
_cell_volume                     2599.5(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            23723
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.910
_diffrn_reflns_theta_min         2.064
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0664 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.9161.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0305P)^2^+0.2648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5545
_reflns_number_total             6831
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03946b2.cif
_cod_data_source_block           mo_dm16283_0m
_cod_depositor_comments          'Adding full bibliography for 7060168.cif.'
_cod_database_code               7060168
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.922
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C12(H12), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              96958
_shelx_hkl_checksum              49301
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'