Enantioselective synthesis of tricyclic oxoquinolines <i>via</i> NHC-catalyzed Michael-aldol-lactamization-dehydration cascade.
Barik, Shilpa; Sankar, Ganga; Biju, Akkattu T.; Chemical communications (Cambridge, England) 60 (2024) 4290–4293; doi:10.1039/d4cc00502c

data_7132777
_publ_section_title
;
 Enantioselective synthesis of tricyclic oxoquinolines <i>via</i>
 NHC-catalyzed Michael-aldol-lactamization-dehydration cascade.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4290
_journal_page_last               4293
_journal_paper_doi               10.1039/d4cc00502c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C41 H33 N O7 S'
_chemical_formula_sum            'C41 H33 N O7 S'
_chemical_formula_weight         683.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-01-04 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1592(3)
_cell_length_b                   17.6405(5)
_cell_length_c                   10.2784(3)
_cell_measurement_reflns_used    6959
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.04
_cell_measurement_theta_min      2.30
_cell_volume                     1656.27(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0703
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            48772
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.140
_diffrn_reflns_theta_max         25.140
_diffrn_reflns_theta_min         1.987
_exptl_absorpt_coefficient_mu    0.154
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0411P)^2^+0.1247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5025
_reflns_number_total             5903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00502c2.cif
_cod_data_source_block           GS_GA_43_reduced1_a
_cod_depositor_comments          'Adding full bibliography for 7132777.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132777
_shelx_shelxl_version_number     2019/1
_shelx_res_checksum              75488
_shelx_hkl_checksum              97077