Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl ketones with trimethylsilyl trifluoromethane.
Kawai, Hiroyuki; Tachi, Kentaro; Tokunaga, Etsuko; Shiro, Motoo; Shibata, Norio; Organic letters 12 (2010) 5104–5107; doi:10.1021/ol102189c

data_1503277
_publ_section_title
;
 Cinchona alkaloid-catalyzed asymmetric trifluoromethylation of alkynyl
 ketones with trimethylsilyl trifluoromethane.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5104
_journal_page_last               5107
_journal_paper_doi               10.1021/ol102189c
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 Br F3 O2 '
_chemical_formula_sum            'C24 H20 Br F3 O2'
_chemical_formula_weight         477.32
_space_group_IT_number           4
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.493(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.90935(16)
_cell_length_b                   21.6684(4)
_cell_length_c                   11.1899(8)
_cell_measurement_reflns_used    8534
_cell_measurement_temperature    153.1
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      4.0
_cell_volume                     2159.49(16)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            51205
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_exptl_absorpt_coefficient_mu    2.980
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             968.00
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.03
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3714 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.002(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     548
_refine_ls_number_reflns         7782
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.4515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                7634
_reflns_number_total             7782
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol102189c_si_001.cif
_cod_data_source_block           '_0602_NITECH'
_cod_original_cell_volume        2159.50(16)
_cod_original_formula_sum        'C24 H20 Br F3 O2 '
_cod_database_code               1503277