Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay.
Fu, Liang; Zhou, Song; Wan, Xiaolong; Chen, Pinhong; Liu, Guosheng; Journal of the American Chemical Society 140 (2018) 10965–10969; doi:10.1021/jacs.8b07436

data_4132931
_publ_section_title
;
 Enantioselective Trifluoromethylalkynylation of Alkenes via
 Copper-Catalyzed Radical Relay.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10965
_journal_page_last               10969
_journal_paper_doi               10.1021/jacs.8b07436
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 Br F3 N4 O3 S'
_chemical_formula_weight         517.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5448(11)
_cell_length_b                   10.370(2)
_cell_length_c                   37.244(8)
_cell_measurement_reflns_used    2856
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      41.274
_cell_measurement_theta_min      4.496
_cell_volume                     2141.5(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            15439
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         2.039
_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
; 
 Flack x determined using 794 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0903P)^2^+0.6805P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2497
_reflns_number_total             4201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07436_si_003.cif
_cod_data_source_block           mo_dm18035_0m
_cod_original_cell_volume        2141.4(7)
_cod_database_code               4132931
_shelx_estimated_absorpt_t_min   0.682
_shelx_estimated_absorpt_t_max   0.820
_shelxl_version_number           2013-4
_shelx_res_checksum              91434
_shelx_hkl_checksum              66471