CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with a pivalamido directing group
Shangjun Cai; Chao Chen; Zelin Sun; Chanjuan Xi; Chem.Commun. 49 (2013) 4552–; doi:10.1039/c3cc41331d

data_7109266
_publ_section_title
;
 CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with
 a pivalamido directing group
;
_journal_name_full               Chem.Commun.
_journal_page_first              4552
_journal_paper_doi               10.1039/c3cc41331d
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         C13H16F3NO2
_chemical_formula_sum            'C13 H16 F3 N O2'
_chemical_formula_weight         275.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.11(3)
_cell_angle_beta                 75.27(3)
_cell_angle_gamma                73.23(3)
_cell_formula_units_Z            8
_cell_length_a                   12.572(3)
_cell_length_b                   13.249(3)
_cell_length_c                   18.106(4)
_cell_measurement_reflns_used    8416
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.61
_cell_volume                     2781.9(12)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       dtprofit.ref
_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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36225
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  .9758
_exptl_absorpt_correction_T_min  .9090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          .849
_exptl_crystal_size_mid          .232
_exptl_crystal_size_min          .215
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         12721
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_gt           0.0868
_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^)+(0.1347P)^2^+1.1033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2448
_refine_ls_wR_factor_ref         0.2775
_reflns_number_gt                10132
_reflns_number_total             12721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41331d.txt
_cod_data_source_block           try
_cod_original_cell_volume        2782.0(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7109266
_refine_ls_r_factor_ref          0.1112