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_4036402
_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         'C5 H6 Cl N O4 S2'
_chemical_formula_sum            'C5 H6 Cl N O4 S2'
_chemical_formula_weight         243.68
_chemical_name_common            04083z
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-06 # Formatted by publCIF

;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.509(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0223(18)
_cell_length_b                   11.561(4)
_cell_length_c                   16.488(6)
_cell_measurement_reflns_used    2896
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.49
_cell_volume                     951.2(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11066
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.9224
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,R.Blessing,1995
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.2794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0718
_reflns_number_gt                1928
_reflns_number_total             2183
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {fb1c8225-82e0-4076-8877-cedcdc49f46f}
_cod_data_source_file            jo5b01826_si_001.cif
_cod_data_source_block           04083z
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4036402