Catalytic Enantioselective Synthesis of 1,4-Dihydropyridines via the Addition of C(1)-Ammonium Enolates to Pyridinium Salts
McLaughlin, Calum; Bitai, Jacqueline; Barber, Lydia; Slawin, Alexandra; Smith, Andrew D.; Chemical Science  (2021) –; doi:10.1039/D1SC03860E

data_1564333
_publ_section_title
;
 Catalytic Enantioselective Synthesis of 1,4-Dihydropyridines via the
 Addition of C(1)-Ammonium Enolates to Pyridinium Salts
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03860E
_journal_year                    2021
_chemical_formula_moiety         'C35 H34 Cl2 N2 O3 S'
_chemical_formula_sum            'C35 H34 Cl2 N2 O3 S'
_chemical_formula_weight         633.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-26
_audit_creation_method           'by CrystalStructure 4.3'
_audit_update_record
;
2021-06-23 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.078(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   27.4341(8)
_cell_length_b                   14.0679(4)
_cell_length_c                   16.1319(5)
_cell_measurement_reflns_used    20689
_cell_measurement_temperature    93
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.00
_cell_volume                     6191.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.016
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2656.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6726
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0623P)^2^+2.7228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5755
_reflns_number_total             6726
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d1sc03860e2.cif
_cod_data_source_block           31
_cod_database_code               1564333
_shelx_res_checksum              72655
_shelx_hkl_checksum              47246