Domino Reactions of 1,2-Diimidoyl-1,2-dichloroethanes. Synthesis of 3-Imino-1,2-dithia-3H-cyclopent-4-enes, 3-Amino-2-thioxo-2,5H-pyrrol-5-ones, 2,3-Diamino-4-thioxo-4H-thiopyrans, and 6-Imino-6H-1,3-oxazines
Esen Bellur; Helmar Görls; Peter Langer; Journal of Organic Chemistry 71 (2006) 2332–2338; doi:10.1021/jo052450l

data_4021555
_publ_contact_author
;
              Langer, Peter 
              Institut f\"ur Chemie 
              Universit\"at Rostock
              Albert-Einstein-Str. 3a
              D-18059 Rostock
              Germany
;
_publ_contact_author_email       'peter.langer@uni-rostock.de '
_publ_contact_author_fax         '+49 (0)381-4986412 '
_publ_contact_author_phone       '+49 (0)381-4986410 '
_publ_section_title
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 Domino Reactions of 1,2-Diimidoyl-1,2-dichloroethanes.
 Synthesis of 3-Imino-1,2-dithia-3H-cyclopent-4-enes,
 3-Amino-2-thioxo-2,5H-pyrrol-5-ones,
 2,3-Diamino-4-thioxo-4H-thiopyrans, and
 6-Imino-6H-1,3-oxazines
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2332
_journal_page_last               2338
_journal_paper_doi               10.1021/jo052450l
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C20 H20 N2 O S'
_chemical_formula_weight         336.44
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_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                   7.4665(2)
_cell_length_b                   14.5957(4)
_cell_length_c                   16.4508(5)
_cell_measurement_temperature    183(2)
_cell_volume                     1792.79(9)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3863
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9944
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.47(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0534P)^2^+0.4758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                3444
_reflns_number_total             3863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052450lsi20051128_054731_2.cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom/difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
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_cod_database_code               4021555