Copper-Catalysed Enantioselective Michael Addition of Malonic Esters to β-Trifluoromethyl-α,β-Unsaturated Imines
Espinosa, Miguel; Herrera, Jorge; Blay, Gonzalo; Cardona, Luz; Muñoz, M Carmen; Pedro, Jose R.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00595D

data_7155566
_publ_section_title
;
 Copper-Catalysed Enantioselective Michael Addition of Malonic Esters to
 \b-Trifluoromethyl-\a,\b-Unsaturated Imines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00595D
_journal_year                    2017
_chemical_formula_sum            'C17 H14 F3 N O2 S'
_chemical_formula_weight         353.35
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.094(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2978(3)
_cell_length_b                   8.3344(3)
_cell_length_c                   37.1632(15)
_cell_measurement_reflns_used    2830
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      28.3700
_cell_measurement_theta_min      3.6650
_cell_volume                     1640.60(13)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'SuperNova, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            13051
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.943
_diffrn_reflns_theta_min         3.284
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0489P)^2^+0.8382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2760
_reflns_number_total             4244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00595d2.cif
_cod_data_source_block           shelx
_cod_database_code               7155566
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2014-1
_shelx_res_checksum              68497