Synthesis of Tri(di)fluoroethylanilines via Copper-Catalyzed Coupling Reaction of Tri(di)fluoroethylamine with (Hetero)Aromatic Bromides
Chen, Suo; Wang, Hui; Jiang, Wei; Rui, Pei-Xin; Hu, Xiang-Guo; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02271F

data_7157180
_publ_section_title
;
 Synthesis of Tri(di)fluoroethylanilines via Copper-Catalyzed Coupling
 Reaction of Tri(di)fluoroethylamine with (Hetero)Aromatic Bromides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02271F
_journal_year                    2019
_chemical_formula_moiety         C11H9F3N2
_chemical_formula_sum            'C11 H9 F3 N2'
_chemical_formula_weight         226.20
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-05-09 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   23.510(2)
_cell_length_b                   23.510(2)
_cell_length_c                   4.8517(6)
_cell_measurement_reflns_used    3024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5920
_cell_measurement_theta_min      4.5410
_cell_volume                     2322.4(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4751
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.464
_diffrn_reflns_theta_min         3.466
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.7143
_exptl_transmission_factor_min   0.6345
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+0.3143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1728
_reflns_number_total             1914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02271f2.cif
_cod_data_source_block           WH20190409-1
_cod_original_cell_volume        2322.4(5)
_cod_database_code               7157180
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              32731