NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
Davies, Alyn T.; Greenhalgh, Mark D.; Slawin, Alexandra M. Z.; Smith, Andrew D.; Beilstein Journal of Organic Chemistry 16 (2020) 1572–1578; doi:10.3762/bjoc.16.129

data_4038540
_publ_section_title
;
 NHC-catalyzed enantioselective synthesis of
 \b-trifluoromethyl-\b-hydroxyamides
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              1572
_journal_page_last               1578
_journal_paper_doi               10.3762/bjoc.16.129
_journal_volume                  16
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H15 Br F3 N O2'
_chemical_formula_sum            'C14 H15 Br F3 N O2'
_chemical_formula_weight         366.18
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.812(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.928(3)
_cell_length_b                   7.168(2)
_cell_length_c                   21.272(7)
_cell_measurement_reflns_used    4955
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      1.90
_cell_volume                     1512.0(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11621
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.457
_diffrn_reflns_theta_min         1.917
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.762
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             736.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.05
_refine_diff_density_min         -0.70
_refine_ls_abs_structure_details
;
 Flack x determined using 1778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5388
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                4653
_reflns_number_total             5388
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            1860-5397-16-129-S2.cif
_cod_data_source_block           12
_cod_depositor_comments          'Adding full bibliography for 4038540.cif.'
_cod_database_code               4038540