#------------------------------------------------------------------------------
#$Date: 2022-01-02 10:39:39 +0200 (Sun, 02 Jan 2022) $
#$Revision: 271679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022781.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_4022781
loop_
_publ_author_name
'Devarajulu Sureshkumar'
'Thanikachalam Gunasundari'
'Venkataraman Ganesh'
'Srinivasan Chandrasekaran'
_publ_section_title
;
 Regio- and Stereospecific Synthesis of β-Sulfonamidodisulfides
 and β-Sulfonamidosulfides from Aziridines using Tetrathiomolybdate
 as a Sulfur Transfer Reagent
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2106
_journal_page_last               2117
_journal_paper_doi               10.1021/jo0624389
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C22 H32 N2 O4 S3'
_chemical_formula_sum            'C22 H32 N2 O4 S3'
_chemical_formula_weight         484.68
_chemical_melting_point          415.15
_chemical_name_common            beta-aminosulfide
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 117.134(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.687(6)
_cell_length_b                   7.638(2)
_cell_length_c                   19.331(6)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.37
_cell_volume                     2455.5(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8517
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0596
_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)+(0.1038P)²+3.6634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1796
_reflns_number_gt                1878
_reflns_number_total             2157
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo0624389si20070101_074737_01.cif
_cod_data_source_block           compound5d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '142 deg' was changed to '415.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

2022-01-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C14.67 H21.33 N1.33 O2.67 S2'
_cod_original_formula_weight         323.12
_cod_original_formula_moiety         'C14.67 H21.33 N1.33 O2.67 S2'
_cod_original_formula_units_Z            6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022781
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
H1 H 0.2147(19) 0.445(4) 0.2907(18) 0.035(9) Uiso 1 1 d .
C11 C 0.2140(4) 0.4949(8) 0.4629(3) 0.1089(18) Uani 1 1 d .
H11A H 0.1817 0.3975 0.4633 0.163 Uiso 1 1 calc R
H11B H 0.2265 0.5670 0.5076 0.163 Uiso 1 1 calc R
H11C H 0.2629 0.4525 0.4641 0.163 Uiso 1 1 calc R
S1 S 0.17578(5) 0.20031(10) 0.27193(4) 0.0468(3) Uani 1 1 d .
S2 S 0.0000 0.73733(19) 0.2500 0.0785(5) Uani 1 2 d S
C1 C 0.10054(18) 0.2033(4) 0.17440(17) 0.0419(7) Uani 1 1 d .
O2 O 0.14655(16) 0.0991(3) 0.31550(13) 0.0646(7) Uani 1 1 d .
O1 O 0.24943(14) 0.1527(4) 0.27115(15) 0.0684(7) Uani 1 1 d .
C2 C 0.1167(2) 0.2759(5) 0.1177(2) 0.0547(8) Uani 1 1 d .
H2 H 0.1675 0.3201 0.1302 0.066 Uiso 1 1 calc R
C6 C 0.02527(19) 0.1372(4) 0.15564(18) 0.0482(7) Uani 1 1 d .
H6 H 0.0145 0.0876 0.1939 0.058 Uiso 1 1 calc R
C4 C -0.0192(2) 0.2168(4) 0.02187(19) 0.0545(8) Uani 1 1 d .
C8 C 0.1283(2) 0.4924(5) 0.3185(2) 0.0574(9) Uani 1 1 d .
H8 H 0.0949 0.4047 0.3271 0.069 Uiso 1 1 calc R
C5 C -0.0340(2) 0.1452(5) 0.0797(2) 0.0551(8) Uani 1 1 d .
H5 H -0.0849 0.1015 0.0671 0.066 Uiso 1 1 calc R
C3 C 0.0565(2) 0.2819(5) 0.0423(2) 0.0608(9) Uani 1 1 d .
H3 H 0.0672 0.3314 0.0041 0.073 Uiso 1 1 calc R
N1 N 0.18913(16) 0.3974(4) 0.30463(16) 0.0484(7) Uani 1 1 d .
C9 C 0.0728(2) 0.5970(5) 0.2445(3) 0.0689(10) Uani 1 1 d .
H9A H 0.0447 0.5136 0.2030 0.083 Uiso 1 1 calc R
H9B H 0.1067 0.6672 0.2295 0.083 Uiso 1 1 calc R
C7 C -0.0846(3) 0.2262(6) -0.0608(2) 0.0772(12) Uani 1 1 d .
H7A H -0.1217 0.3176 -0.0653 0.116 Uiso 1 1 calc R
H7B H -0.1126 0.1163 -0.0750 0.116 Uiso 1 1 calc R
H7C H -0.0612 0.2505 -0.0948 0.116 Uiso 1 1 calc R
C10 C 0.1694(3) 0.5984(7) 0.3920(3) 0.0889(14) Uani 1 1 d .
H10A H 0.2064 0.6792 0.3863 0.107 Uiso 1 1 calc R
H10B H 0.1292 0.6674 0.3982 0.107 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
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
O2 S1 O1 119.95(17) .
O2 S1 N1 107.97(16) .
O1 S1 N1 105.34(16) .
O2 S1 C1 107.79(15) .
O1 S1 C1 107.08(15) .
N1 S1 C1 108.25(14) .
C9 S2 C9 105.6(3) 2
C6 C1 C2 120.4(3) .
C6 C1 S1 119.8(2) .
C2 C1 S1 119.8(3) .
C3 C2 C1 119.0(3) .
C3 C2 H2 120.5 .
C1 C2 H2 120.5 .
C1 C6 C5 119.4(3) .
C1 C6 H6 120.3 .
C5 C6 H6 120.3 .
C3 C4 C5 118.0(3) .
C3 C4 C7 121.2(4) .
C5 C4 C7 120.9(4) .
N1 C8 C10 109.4(3) .
N1 C8 C9 109.4(3) .
C10 C8 C9 115.6(4) .
N1 C8 H8 107.3 .
C10 C8 H8 107.3 .
C9 C8 H8 107.3 .
C4 C5 C6 121.3(3) .
C4 C5 H5 119.3 .
C6 C5 H5 119.3 .
C4 C3 C2 122.0(3) .
C4 C3 H3 119.0 .
C2 C3 H3 119.0 .
C8 N1 S1 122.6(2) .
C8 N1 H1 120(3) .
S1 N1 H1 109(3) .
C8 C9 S2 117.7(3) .
C8 C9 H9A 107.9 .
S2 C9 H9A 107.9 .
C8 C9 H9B 107.9 .
S2 C9 H9B 107.9 .
H9A C9 H9B 107.2 .
C4 C7 H7A 109.5 .
C4 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
C4 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C11 C10 C8 114.8(4) .
C11 C10 H10A 108.6 .
C8 C10 H10A 108.6 .
C11 C10 H10B 108.6 .
C8 C10 H10B 108.6 .
H10A C10 H10B 107.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C10 1.468(7) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
S1 O2 1.423(3) .
S1 O1 1.430(2) .
S1 N1 1.608(3) .
S1 C1 1.765(3) .
S2 C9 1.772(4) 2
S2 C9 1.772(4) .
C1 C6 1.378(4) .
C1 C2 1.379(5) .
C2 C3 1.377(5) .
C2 H2 0.9300 .
C6 C5 1.380(5) .
C6 H6 0.9300 .
C4 C3 1.376(5) .
C4 C5 1.380(5) .
C4 C7 1.507(5) .
C8 N1 1.472(4) .
C8 C10 1.506(6) .
C8 C9 1.552(5) .
C8 H8 0.9800 .
C5 H5 0.9300 .
C3 H3 0.9300 .
N1 H1 0.74(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
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_1
O2 S1 C1 C6 9.0(3) .
O1 S1 C1 C6 139.4(3) .
N1 S1 C1 C6 -107.5(3) .
O2 S1 C1 C2 -172.7(3) .
O1 S1 C1 C2 -42.3(3) .
N1 S1 C1 C2 70.8(3) .
C6 C1 C2 C3 0.3(5) .
S1 C1 C2 C3 -178.0(3) .
C2 C1 C6 C5 -0.4(5) .
S1 C1 C6 C5 177.9(2) .
C3 C4 C5 C6 -0.6(5) .
C7 C4 C5 C6 -179.5(3) .
C1 C6 C5 C4 0.6(5) .
C5 C4 C3 C2 0.5(5) .
C7 C4 C3 C2 179.4(3) .
C1 C2 C3 C4 -0.3(5) .
C10 C8 N1 S1 140.8(3) .
C9 C8 N1 S1 -91.6(4) .
O2 S1 N1 C8 -47.3(3) .
O1 S1 N1 C8 -176.6(3) .
C1 S1 N1 C8 69.1(3) .
N1 C8 C9 S2 -174.6(3) .
C10 C8 C9 S2 -50.6(5) .
C9 S2 C9 C8 -70.7(3) 2
N1 C8 C10 C11 -62.8(5) .
C9 C8 C10 C11 173.1(4) .
