A perfect double role of CF3 groups in activating substrates and stabilizing adducts: the chiral Brønsted acid-catalyzed direct arylation of trifluoromethyl ketones.
Nie, Jing; Zhang, Guang-Wu; Wang, Lian; Fu, Aiping; Zheng, Yan; Ma, Jun-An; Chemical communications (Cambridge, England) 34 (2009) 2356–2358; doi:10.1039/b900474b

data_7104366
_publ_section_title
;
 A perfect double role of CF3 groups in activating substrates and
 stabilizing adducts: the chiral Br\/onsted acid-catalyzed direct
 arylation of trifluoromethyl ketones.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2356
_journal_page_last               2358
_journal_paper_doi               10.1039/b900474b
_journal_volume                  34
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_sum            'C16 H11 Cl F3 N O'
_chemical_formula_weight         325.71
_chemical_name_common
1-(4-chlorophenyl)-2,2,2-trifluoro-1-(1H-indole-3-yl)ethanol
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4634(15)
_cell_length_b                   13.393(3)
_cell_length_c                   15.347(3)
_cell_measurement_reflns_used    12745
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.0
_cell_volume                     1534.0(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  SHELXL
_computing_structure_solution    DirectMethod
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       multi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16222
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.2240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2190
_reflns_number_total             3510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900474b.txt
_cod_data_source_block           1
_cod_database_code               7104366