Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomünchnones
Michael, Joseph P.; de Koning, Charles B.; van der Westhuyzen, Christiaan W.; Fernandes, Manuel A.; Journal of the Chemical Society, Perkin Transactions 1  (2001) 2055–; doi:10.1039/b103560f

data_7213486
_publ_section_title
;
 Influence of ring size on the outcome of sulfide contraction reactions
 with thiolactams. Isolation of bicyclic ketene S,N-acetals and
 thioisom\"unchnones
;
_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2055
_journal_paper_doi               10.1039/b103560f
_journal_year                    2001
_chemical_formula_moiety         'C26 H32 N2 O10 S2'
_chemical_formula_sum            'C26 H32 N2 O10 S2'
_chemical_formula_weight         596.66
_chemical_name_systematic
;meso-3,3'-dioxo-6,7,6',7'-tetrahydro-
5H,5H'-[2,2']bi([1,3]thiazolo[3,2-a]pyridinyl)-2,2',8,8'-tetracarboxylate 
;
_chemical_temperature_decomposition 525.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.103(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1807(19)
_cell_length_b                   11.696(2)
_cell_length_c                   13.880(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1438.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL, PLATON (Spek, 1990)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7624
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9373
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismic
_exptl_crystal_F_000             628
_exptl_crystal_preparation       'Slow evaporation from acetone'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0838P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                1405
_reflns_number_total             2528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b103560fsup1.cif
_cod_data_source_block           cwdimr_s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '252 deg C decomp.'. The value '252 deg C decomp.' was changed to
'525.15' - it was converted from degrees Celsius(C) to
Kelvins(K).

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1439.0(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7213486