Proline-Catalyzed Asymmetric Synthesis of syn- and anti-1,3-Diamines
Pradeep Kumar; Vishwajeet Jha; Rajesh Gonnade; Journal of Organic Chemistry 78 (2013) 11756–11764; doi:10.1021/jo401722e

data_4028774
_publ_section_title
;
 Proline-Catalyzed Asymmetric Synthesis of syn- and anti-1,3-Diamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11756
_journal_page_last               11764
_journal_paper_doi               10.1021/jo401722e
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H26 N2 O4 S2'
_chemical_formula_sum            'C19 H26 N2 O4 S2'
_chemical_formula_weight         410.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.666(10)
_cell_length_b                   10.666(10)
_cell_length_c                   18.087(17)
_cell_measurement_reflns_used    6451
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.69
_cell_volume                     2058(3)
_computing_cell_refinement       'APEX2(BRUKER, 2006)'
_computing_data_collection       'APEX2(BRUKER, 2006)'
_computing_data_reduction        'APEX2(BRUKER, 2006)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD AREA DETECTOR'
_diffrn_measurement_method       'OMEGA AND PHI SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18655
_diffrn_reflns_theta_full        26.88
_diffrn_reflns_theta_max         26.88
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.9531
_exptl_absorpt_correction_T_min  0.8871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2006)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.4823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1996
_reflns_number_total             2208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401722e_si_002.cif
_cod_data_source_block           rahul2_2
_cod_database_code               4028774