Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines.
Li, Kangnan; Weber, Alexandria E.; Tseng, Luke; Malcolmson, Steven J.; Organic letters 19 (2017) 4239–4242; doi:10.1021/acs.orglett.7b01886

data_1547079
_publ_section_title
;
 Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via
 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4239
_journal_page_last               4242
_journal_paper_doi               10.1021/acs.orglett.7b01886
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N2 O2 S, H2 O'
_chemical_formula_sum            'C22 H26 N2 O3 S'
_chemical_formula_weight         398.51
_chemical_name_common            AEW-II-133
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6401(7)
_cell_length_b                   15.5044(18)
_cell_length_c                   23.257(3)
_cell_measurement_reflns_used    403
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.8945
_cell_measurement_theta_min      2.7285
_cell_volume                     2033.7(4)
_computing_cell_refinement       'APEX3 v2015.5-2 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            46044
_diffrn_reflns_theta_full        29.23
_diffrn_reflns_theta_max         29.23
_diffrn_reflns_theta_min         1.58
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.301
_refine_ls_abs_structure_details
;

Flack x determined using 1992 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0575P)^2^+0.3889P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                4961
_reflns_number_total             5499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01886_si_001.cif
_cod_data_source_block           rds504
_cod_database_code               1547079
_shelx_res_checksum              90280
_shelx_hkl_checksum              76269