Enantioselective Friedel-Crafts Alkylation of Indoles with Trifluoroethylidene Malonates by Copper-Bis(oxazoline) Complexes: Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Center
Lele Wen; Qilong Shen; Xiaolong Wan; Long Lu; Journal of Organic Chemistry 76 (2011) 2282–2285; doi:10.1021/jo1024333

data_4026159
_publ_section_title
;
 Enantioselective Friedel-Crafts Alkylation of Indoles with
 Trifluoroethylidene Malonates by Copper-Bis(oxazoline) Complexes:
 Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon
 Center
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2282
_journal_page_last               2285
_journal_paper_doi               10.1021/jo1024333
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C25 H21 F3 N2 O2 S'
_chemical_formula_weight         470.50
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.810(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7183(14)
_cell_length_b                   8.8432(12)
_cell_length_c                   12.4477(17)
_cell_measurement_reflns_used    1699
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.989
_cell_measurement_theta_min      5.708
_cell_volume                     1145.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0764
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6811
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.811
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4721
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.811
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                3067
_reflns_number_total             4721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024333_si_003.cif
_cod_data_source_block           cd201372
_cod_database_code               4026159