#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028774.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4028774
loop_
_publ_author_name
'Pradeep Kumar'
'Vishwajeet Jha'
'Rajesh Gonnade'
_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/[σ²(Fo²)+(0.0506P)²+0.4823P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.28710(5) 0.20706(6) 0.13506(3) 0.04831(17) Uani 1 1 d .
O1 O 0.27625(18) 0.32105(16) 0.09486(9) 0.0667(5) Uani 1 1 d .
O2 O 0.40671(15) 0.1501(2) 0.14536(10) 0.0716(6) Uani 1 1 d .
N1 N 0.20346(16) 0.10252(16) 0.09393(9) 0.0438(4) Uani 1 1 d .
H1N H 0.2346 0.0291 0.0870 0.053 Uiso 1 1 d R
C1 C -0.0203(2) 0.0998(2) 0.12942(13) 0.0553(5) Uani 1 1 d .
H1A H -0.0121 0.0140 0.1447 0.083 Uiso 1 1 calc R
H1B H -0.1035 0.1139 0.1111 0.083 Uiso 1 1 calc R
H1C H -0.0050 0.1540 0.1708 0.083 Uiso 1 1 calc R
C2 C 0.07451(18) 0.12768(18) 0.06857(11) 0.0406(4) Uani 1 1 d .
H2 H 0.0679 0.2164 0.0551 0.049 Uiso 1 1 calc R
C3 C 0.04830(18) 0.04830(18) 0.0000 0.0431(6) Uani 1 2 d S
H3A H 0.0594 -0.0391 0.0133 0.052 Uiso 0.50 1 calc PR
H3B H -0.0391 0.0594 -0.0133 0.052 Uiso 0.50 1 calc PR
C4 C 0.22445(19) 0.23510(19) 0.22374(11) 0.0434(5) Uani 1 1 d .
C5 C 0.1499(2) 0.3398(2) 0.23613(12) 0.0473(5) Uani 1 1 d .
H5 H 0.1317 0.3947 0.1977 0.057 Uiso 1 1 calc R
C6 C 0.1029(2) 0.3613(2) 0.30647(13) 0.0503(5) Uani 1 1 d .
H6 H 0.0523 0.4310 0.3148 0.060 Uiso 1 1 calc R
C7 C 0.1297(2) 0.2812(2) 0.36462(12) 0.0482(5) Uani 1 1 d .
C8 C 0.2010(2) 0.1761(2) 0.35016(12) 0.0532(5) Uani 1 1 d .
H8 H 0.2178 0.1201 0.3883 0.064 Uiso 1 1 calc R
C9 C 0.2478(2) 0.1522(2) 0.28090(12) 0.0487(5) Uani 1 1 d .
H9 H 0.2950 0.0804 0.2724 0.058 Uiso 1 1 calc R
C10 C 0.0842(3) 0.3096(3) 0.44145(14) 0.0701(8) Uani 1 1 d .
H10A H 0.0501 0.2349 0.4632 0.105 Uiso 1 1 calc R
H10B H 0.0204 0.3730 0.4393 0.105 Uiso 1 1 calc R
H10C H 0.1529 0.3390 0.4710 0.105 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
O1 S1 O2 120.28(12) .
O1 S1 N1 108.11(11) .
O2 S1 N1 105.16(11) .
O1 S1 C4 106.82(12) .
O2 S1 C4 107.01(11) .
N1 S1 C4 109.14(10) .
C2 N1 S1 122.31(13) .
C2 N1 H1N 118.7 .
S1 N1 H1N 119.0 .
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N1 C2 C1 111.02(17) .
N1 C2 C3 108.81(15) .
C1 C2 C3 110.91(18) .
N1 C2 H2 108.7 .
C1 C2 H2 108.7 .
C3 C2 H2 108.7 .
C2 C3 C2 117.2(2) 6
C2 C3 H3A 108.0 6
C2 C3 H3A 108.0 .
C2 C3 H3B 108.0 6
C2 C3 H3B 108.0 .
H3A C3 H3B 107.3 .
C9 C4 C5 119.7(2) .
C9 C4 S1 120.23(18) .
C5 C4 S1 120.02(17) .
C6 C5 C4 119.2(2) .
C6 C5 H5 120.4 .
C4 C5 H5 120.4 .
C7 C6 C5 121.3(2) .
C7 C6 H6 119.4 .
C5 C6 H6 119.4 .
C8 C7 C6 118.1(2) .
C8 C7 C10 121.2(2) .
C6 C7 C10 120.7(2) .
C9 C8 C7 121.7(2) .
C9 C8 H8 119.2 .
C7 C8 H8 119.2 .
C8 C9 C4 119.9(2) .
C8 C9 H9 120.1 .
C4 C9 H9 120.1 .
C7 C10 H10A 109.5 .
C7 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C7 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.421(2) .
S1 O2 1.425(2) .
S1 N1 1.610(2) .
S1 C4 1.763(3) .
N1 C2 1.474(3) .
N1 H1N 0.8596 .
C1 C2 1.524(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.527(3) .
C2 H2 0.9800 .
C3 C2 1.527(3) 6
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C9 1.383(3) .
C4 C5 1.389(3) .
C5 C6 1.387(3) .
C5 H5 0.9300 .
C6 C7 1.385(3) .
C6 H6 0.9300 .
C7 C8 1.379(4) .
C7 C10 1.503(3) .
C8 C9 1.372(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
O1 S1 N1 C2 -46.10(18) .
O2 S1 N1 C2 -175.76(16) .
C4 S1 N1 C2 69.73(17) .
S1 N1 C2 C1 -88.3(2) .
S1 N1 C2 C3 149.32(14) .
N1 C2 C3 C2 -63.31(12) 6
C1 C2 C3 C2 174.29(19) 6
O1 S1 C4 C9 -164.85(17) .
O2 S1 C4 C9 -34.8(2) .
N1 S1 C4 C9 78.49(18) .
O1 S1 C4 C5 16.11(19) .
O2 S1 C4 C5 146.14(17) .
N1 S1 C4 C5 -100.55(18) .
C9 C4 C5 C6 1.9(3) .
S1 C4 C5 C6 -179.08(16) .
C4 C5 C6 C7 0.5(3) .
C5 C6 C7 C8 -2.4(3) .
C5 C6 C7 C10 176.5(2) .
C6 C7 C8 C9 1.8(3) .
C10 C7 C8 C9 -177.0(2) .
C7 C8 C9 C4 0.5(3) .
C5 C4 C9 C8 -2.4(3) .
S1 C4 C9 C8 178.55(17) .
