Asymmetric Redox-Annulation of Cyclic Amines.
Kang, YoungKu; Chen, Weijie; Breugst, Martin; Seidel, Daniel; The Journal of organic chemistry 80 (2015) 9628–9640; doi:10.1021/acs.joc.5b01384

data_4036277
_publ_section_title
;
 Asymmetric Redox-Annulation of Cyclic Amines.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9628
_journal_page_last               9640
_journal_paper_doi               10.1021/acs.joc.5b01384
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 Br N2 O2, (C H4 O)'
_chemical_formula_sum            'C21 H25 Br N2 O3'
_chemical_formula_weight         433.34
_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
_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                   7.9265(14)
_cell_length_b                   10.5847(19)
_cell_length_c                   23.895(4)
_cell_measurement_reflns_used    6858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.55
_cell_measurement_theta_min      2.57
_cell_volume                     2004.8(6)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            28061
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.028
_diffrn_reflns_theta_min         1.704
_exptl_absorpt_coefficient_mu    2.074
_exptl_absorpt_correction_T_max  0.4348
_exptl_absorpt_correction_T_min  0.3594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
; 
 Flack x determined using 2566 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         6979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6356
_reflns_number_total             6979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01384_si_001.cif
_cod_data_source_block           major_P212121
_cod_database_code               4036277
_shelx_estimated_absorpt_t_min   0.469
_shelx_estimated_absorpt_t_max   0.789
_shelxl_version_number           2013-4
_shelx_res_checksum              94397
_shelx_hkl_checksum              93090