Synthesis of 1,4-Dihydroquinolines and 4<i>H</i>-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of <i>para</i>-Quinone Methides and Ynals.
Wang, Junwei; Rong, Quanjin; Zhao, Lei; Pan, Xiang; Zhao, Lin; Zhao, Kun; Hu, Lihong; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01315

data_4038711
_publ_section_title
;
 Synthesis of 1,4-Dihydroquinolines and 4<i>H</i>-Chromenes via
 Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of
 <i>para</i>-Quinone Methides and Ynals.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01315
_journal_year                    2020
_chemical_formula_sum            'C37 H39 N O4 S'
_chemical_formula_weight         593.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.443(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0613(10)
_cell_length_b                   17.674(2)
_cell_length_c                   20.106(2)
_cell_measurement_reflns_used    2095
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      53.57
_cell_measurement_theta_min      11.93
_cell_volume                     3156.0(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22532
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.823
_diffrn_reflns_theta_min         2.922
_exptl_absorpt_coefficient_mu    0.800
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5695
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0628P)^2^+2.5638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4412
_reflns_number_total             5695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01315_si_002.cif
_cod_data_source_block           20191218LI_NZY_APa_0m_a
_cod_original_cell_volume        3156.1(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038711
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              6209
_shelx_hkl_checksum              52210