Enantioselective N-heterocyclic carbene-catalyzed synthesis of trifluoromethyldihydropyridinones.
Wang, Dong-Ling; Liang, Zhi-Qin; Chen, Kun-Quan; Sun, De-Qun; Ye, Song; The Journal of organic chemistry 80 (2015) 5900–5905; doi:10.1021/acs.joc.5b00232

data_4036138
_publ_section_title
;
 Enantioselective N-heterocyclic carbene-catalyzed synthesis of
 trifluoromethyldihydropyridinones.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5900
_journal_page_last               5905
_journal_paper_doi               10.1021/acs.joc.5b00232
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 Br F3 N O3'
_chemical_formula_sum            'C24 H23 Br F3 N O3'
_chemical_formula_weight         510.34
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.971(2)
_cell_length_b                   11.971(2)
_cell_length_c                   16.556(3)
_cell_measurement_reflns_used    6779
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4817
_cell_measurement_theta_min      1.7006
_cell_volume                     2372.6(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0123
_diffrn_orient_matrix_UB_12      -0.0775
_diffrn_orient_matrix_UB_13      -0.0286
_diffrn_orient_matrix_UB_21      0.0562
_diffrn_orient_matrix_UB_22      0.0149
_diffrn_orient_matrix_UB_23      -0.0162
_diffrn_orient_matrix_UB_31      0.0279
_diffrn_orient_matrix_UB_32      -0.0233
_diffrn_orient_matrix_UB_33      0.0752
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18348
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.406
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.781
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0371P)^2^+0.4962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4994
_reflns_number_total             5395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00232_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        2372.7(10)
_cod_original_sg_symbol_Hall     'P 41'
_cod_database_code               4036138
_shelxl_version_number           2013-4
_diffrn_number_total             5618
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              88090
_shelx_hkl_checksum              85715