Unexpectedly Stable (Chlorocarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane, and Related Compounds That Model the Zumach-Weiss-Kühle (ZWK) Reaction for Synthesis of 1,2,4-Dithiazolidine-3,5-diones.
Barany, George; Britton, Doyle; Chen, Lin; Hammer, Robert P.; Henley, Matthew J.; Schrader, Alex M.; Young, Jr, Victor G; The Journal of organic chemistry 80 (2015) 11313–11321; doi:10.1021/acs.joc.5b01826

data_4036403
_publ_section_title
;
 Unexpectedly Stable (Chlorocarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane,
 and Related Compounds That Model the Zumach-Weiss-K\"uhle (ZWK) Reaction
 for Synthesis of 1,2,4-Dithiazolidine-3,5-diones.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11313
_journal_page_last               11321
_journal_paper_doi               10.1021/acs.joc.5b01826
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C14 H18 N2 O4 S2'
_chemical_formula_sum            'C14 H18 N2 O4 S2'
_chemical_formula_weight         342.42
_chemical_name_common            031026z
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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                 118.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.338(6)
_cell_length_b                   9.106(2)
_cell_length_c                   21.687(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      17.8
_cell_volume                     3357(2)
_computing_cell_refinement       'Collect (Enraf-Nonius)'
_computing_data_collection       'Collect (Enraf-Nonius)'
_computing_data_reduction        'Collect (Enraf-Nonius)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2000)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 2000)'
_computing_structure_refinement  'SHELXTL (Bruker-AXS, 2000)'
_computing_structure_solution    Texsan
_diffrn_ambient_temperature      172(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf-Nonus CAD4'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.1011
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4032
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.8777
_exptl_absorpt_correction_T_min  0.7994
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   Texsan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0412P)^2^+0.6006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                2386
_reflns_number_total             4032
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {572d350b-c438-4677-a174-1631dae1ba04}
_cod_data_source_file            jo5b01826_si_001.cif
_cod_data_source_block           031026z
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036403