Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers
Sean K. Liew; Zhi He; Jeffrey D. St. Denis; Andrei K. Yudin; Journal of Organic Chemistry 78 (2013) 11637–11645; doi:10.1021/jo401489q

data_4028770
_publ_section_title
;
 Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from
 Aziridine Aldehyde Dimers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11637
_journal_page_last               11645
_journal_paper_doi               10.1021/jo401489q
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H33 N3 O4'
_chemical_formula_sum            'C26 H33 N3 O4'
_chemical_formula_weight         451.55
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1020(6)
_cell_length_b                   10.1363(6)
_cell_length_c                   46.985(3)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      3.76
_cell_volume                     4811.1(5)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            31467
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.645
_diffrn_reflns_theta_min         1.880
_diffrn_source                   'Bruker ImuS'
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 3499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         8268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0319P)^2^+1.2848P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                8182
_reflns_number_total             8268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo401489q_si_001_1.cif
_cod_data_source_block           d1386
_cod_database_code               4028770
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.929
_shelxl_version_number           2013-2