Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis.
Martínez-Pardo, Pablo; Blay, Gonzalo; Vila, Carlos; Sanz-Marco, Amparo; Muñoz, M Carmen; Pedro, José R; The Journal of organic chemistry 84 (2019) 314–325; doi:10.1021/acs.joc.8b02808

data_4035880
_publ_section_title
;
 Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual
 Silver/Organocatalysis.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              314
_journal_page_last               325
_journal_paper_doi               10.1021/acs.joc.8b02808
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H15 Br F3 N O3'
_chemical_formula_weight         394.19
_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   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 118.539(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7236(5)
_cell_length_b                   11.9043(4)
_cell_length_c                   8.7256(4)
_cell_measurement_reflns_used    3336
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      27.5770
_cell_measurement_theta_min      4.3230
_cell_volume                     796.04(8)
_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 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6958
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.808
_diffrn_reflns_theta_min         3.423
_exptl_absorpt_coefficient_mu    2.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.812
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0566P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.783
_reflns_Friedel_fraction_max     0.630
_reflns_number_gt                3225
_reflns_number_total             3533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02808_si_003.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        796.03(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035880
_shelx_estimated_absorpt_t_min   0.743
_shelx_estimated_absorpt_t_max   0.817
_shelxl_version_number           2014-1
_shelx_res_checksum              91583
_shelx_hkl_checksum              50272