Trapping of chiral enolates generated by Lewis acid promoted conjugate addition of Grignard reagents to unreactive Michael acceptors by various electrophiles
Vargová, Denisa; Perez, Juana M.; Harutyunyan, Syuzanna R.; Sebesta, Radovan; Chemical Communications  (2019) –; doi:10.1039/C9CC05041H

data_7124115
_publ_section_title
;
 Trapping of chiral enolates generated by Lewis acid promoted conjugate
 addition of Grignard reagents to unreactive Michael acceptors by various
 electrophiles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05041H
_journal_year                    2019
_chemical_formula_moiety         'C24 H21 N O S2'
_chemical_formula_sum            'C24 H21 N O S2'
_chemical_formula_weight         403.54
_chemical_name_systematic
2-(1-(benzo[d][1,3]dithiol-2-yl)-2-phenylbutyl)benzo[d]oxazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-06-28 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3601(5)
_cell_length_b                   8.9695(3)
_cell_length_c                   15.4933(5)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.51
_cell_measurement_theta_min      5.72
_cell_volume                     1971.33(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3495
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.584
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_min         3.115
_exptl_absorpt_coefficient_mu    2.554
_exptl_absorpt_correction_T_max  0.753817
_exptl_absorpt_correction_T_min  0.565842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v.2012/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Pentane, DCM'
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0275P)^2^+4.5661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3219
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05041h2.cif
_cod_data_source_block           twin5
_cod_database_code               7124115
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.471
_shelx_estimated_absorpt_t_max   0.662
_shelx_res_checksum              21058