Enantioselective Conjugate Additions of α-Amino Radicals via Cooperative Photoredox and Lewis Acid Catalysis.
Ruiz Espelt, Laura; McPherson, Iain S.; Wiensch, Eric M.; Yoon, Tehshik P.; Journal of the American Chemical Society 137 (2015) 2452–2455; doi:10.1021/ja512746q

data_4123439
_publ_section_title
;
 Enantioselective Conjugate Additions of \a-Amino Radicals via Cooperative
 Photoredox and Lewis Acid Catalysis.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2452
_journal_page_last               2455
_journal_paper_doi               10.1021/ja512746q
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H15 Br N O2, C8 H12 N'
_chemical_formula_sum            'C20 H27 Br N2 O2'
_chemical_formula_weight         407.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.35(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.787(4)
_cell_length_b                   6.031(2)
_cell_length_c                   15.094(4)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      3.14
_cell_volume                     999.4(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29437
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.316
_diffrn_reflns_theta_min         3.143
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.915
_exptl_absorpt_correction_T_max  0.3331
_exptl_absorpt_correction_T_min  0.1818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1025 before and 0.0336 after correction. The Ratio of minimum to maximum transmission is 0.5458. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.788
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0480P)^2^+0.5205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3875
_reflns_number_total             3904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja512746q_si_003.cif
_cod_data_source_block           yoon36
_cod_depositor_comments
'Adding full bibliography for 4123439--4123440.cif.'
_cod_original_cell_volume        999.5(6)
_cod_database_code               4123439
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.792
_shelx_estimated_absorpt_t_min   0.207
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A \\sim N2-H2C \\sim N2-H2B
 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
3.d Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
3.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              7509
_shelx_hkl_checksum              6253
_olex2_submission_special_instructions 'No special instructions were received'