Bi(OTf)<sub>3</sub>-Catalyzed Diastereoselective One-Pot Synthesis of 1,3-Diamines with Three Continuous Stereogenic Centers.
Halli, Juliette; Kramer, Philipp; Grimmer, Jennifer; Bolte, Michael; Manolikakes, Georg; The Journal of organic chemistry 83 (2018) 12007–12022; doi:10.1021/acs.joc.8b01925

data_4035232
_publ_section_title
;
 Bi(OTf)<sub>3</sub>-Catalyzed Diastereoselective One-Pot Synthesis of
 1,3-Diamines with Three Continuous Stereogenic Centers.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12007
_journal_page_last               12022
_journal_paper_doi               10.1021/acs.joc.8b01925
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H26 N2 O3 S'
_chemical_formula_sum            'C27 H26 N2 O3 S'
_chemical_formula_weight         458.56
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.12421(8)
_cell_length_b                   18.4100(3)
_cell_length_c                   24.5471(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      134.729
_cell_measurement_theta_min      5.996
_cell_volume                     2315.69(6)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'APEX2 CCD three-circle diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36604
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.018
_diffrn_reflns_theta_min         3.000
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    1.498
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0785
_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^)+(0.1319P)^2^+2.4519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2190
_refine_ls_wR_factor_ref         0.2271
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3556
_reflns_number_total             4183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01925_si_001.cif
_cod_data_source_block           ma96
_cod_database_code               4035232
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              54526
_shelx_hkl_checksum              97129