Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals.
Wu, Lianqian; Wang, Fei; Chen, Pinhong; Liu, Guosheng; Journal of the American Chemical Society 141 (2019) 1887–1892; doi:10.1021/jacs.8b13052

data_4127906
_publ_section_title
;
 Enantioselective Construction of Quaternary All-Carbon Centers via
 Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1887
_journal_page_last               1892
_journal_paper_doi               10.1021/jacs.8b13052
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H17 Br F3 N O'
_chemical_formula_sum            'C22 H17 Br F3 N O'
_chemical_formula_weight         448.27
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                107.9390(10)
_cell_angle_beta                 92.9350(10)
_cell_angle_gamma                116.2110(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0143(3)
_cell_length_b                   10.1957(3)
_cell_length_c                   11.7671(3)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      54.551
_cell_measurement_theta_min      3.522
_cell_volume                     1000.53(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      303.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24850
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.906
_diffrn_reflns_theta_min         3.521
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1412 before and 0.0829 after correction. The Ratio of minimum to maximum transmission is 0.6911. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.099
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 2533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.063(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7453
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0769P)^2^+0.4120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                6292
_reflns_number_total             7453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13052_si_003.cif
_cod_data_source_block           mjr18029_0m
_cod_database_code               4127906
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.739
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), N2(H2),
 C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37),
  C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
;
_shelx_res_checksum              69048
_shelx_hkl_checksum              94709
_olex2_submission_special_instructions 'No special instructions were received'