A Dual-Catalytic Strategy To Direct Asymmetric Radical Aminotrifluoromethylation of Alkenes.
Lin, Jin-Shun; Dong, Xiao-Yang; Li, Tao-Tao; Jiang, Na-Chuan; Tan, Bin; Liu, Xin-Yuan; Journal of the American Chemical Society 138 (2016) 9357–9360; doi:10.1021/jacs.6b04077

data_4130496
_publ_section_title
;
 A Dual-Catalytic Strategy To Direct Asymmetric Radical
 Aminotrifluoromethylation of Alkenes.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9357
_journal_page_last               9360
_journal_paper_doi               10.1021/jacs.6b04077
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 Br F3 N2 O'
_chemical_formula_sum            'C21 H22 Br F3 N2 O'
_chemical_formula_weight         455.31
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5823(10)
_cell_length_b                   16.3674(12)
_cell_length_c                   17.4983(12)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.43
_cell_measurement_theta_min      3.70
_cell_volume                     4176.4(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            67163
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.612
_diffrn_reflns_theta_max         67.612
_diffrn_reflns_theta_min         3.698
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.035
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1051 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.7704.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+1.3552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                7434
_reflns_number_total             7473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04077_si_002.cif
_cod_data_source_block           cxy391_0m
_cod_database_code               4130496
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C7(H7A,H7B), C22(H22A,H22B), C26(H26A,H26B),
 C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), N4(H4), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C38(H38), C39(H39), C41(H41), C42(H42)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'