Formation of 1,4,2-Dithiazolidines or 1,3-Thiazetidines from 1,1-Dichloro-2-nitroethene and Phenylthiourea Derivatives.
Feng, Yian; Zou, Minming; Song, Runjiang; Shao, Xusheng; Li, Zhong; Qian, Xuhong; The Journal of organic chemistry 81 (2016) 10321–10327; doi:10.1021/acs.joc.6b01307

data_4037026
_publ_section_title
;
 Formation of 1,4,2-Dithiazolidines or 1,3-Thiazetidines from
 1,1-Dichloro-2-nitroethene and Phenylthiourea Derivatives.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10321
_journal_page_last               10327
_journal_paper_doi               10.1021/acs.joc.6b01307
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C16 H12 N4 O4 S'
_chemical_formula_sum            'C16 H12 N4 O4 S'
_chemical_formula_weight         356.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.705(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.524(3)
_cell_length_b                   7.0624(9)
_cell_length_c                   19.532(3)
_cell_measurement_reflns_used    1630
_cell_measurement_temperature    130
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.260
_cell_volume                     3120.7(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24932
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         0.900
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0701 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.8349.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0494P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3840
_reflns_number_total             7166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01307_si_004.cif
_cod_data_source_block           dm15294
_cod_database_code               4037026
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              31447
_shelx_hkl_checksum              81194
_olex2_submission_special_instructions 'No special instructions were received'