Copper-Catalyzed para-Selective C–H Amination of Electron-Rich Arenes
Berzina, Beatrise; Sokolovs, Igors; Suna, Edgars; ACS Catalysis 5 (2015) 7008–; doi:10.1021/acscatal.5b01992

data_4516690
_publ_section_title
;
 Copper-Catalyzed para-Selective C--H Amination of Electron-Rich Arenes
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7008
_journal_paper_doi               10.1021/acscatal.5b01992
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C23 H32 I, C F3 O3 S '
_chemical_formula_sum            'C24 H32 F3 I O3 S'
_chemical_formula_weight         584.46
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5647(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6451(2)
_cell_length_b                   25.6279(5)
_cell_length_c                   10.7472(2)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     2592.91(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w 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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11048
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         1.5
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle '
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.810
_refine_diff_density_min         -1.156
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0357P)^2^+12.4754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1377
_reflns_d_resolution_high        0.7582
_reflns_number_gt                4854
_reflns_number_total             6087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs5b01992_si_002.cif
_cod_data_source_block           bb274
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4516690
_shelx_title                     ' Compound BB-274'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            388.09
_shelx_f_squared_multiplier      1.000