Unexpected reactivity of diaryl α-diketones with thiazolium carbenes: discovery of a novel multicomponent reaction for the facile synthesis of 1,4-thiazin-3-ones.
Bertolasi, Valerio; Bortolini, Olga; Donvito, Adelaide; Fantin, Giancarlo; Fogagnolo, Marco; Giovannini, Pier Paolo; Massi, Alessandro; Pacifico, Salvatore; Organic & biomolecular chemistry 10 (2012) 6579–6586; doi:10.1039/c2ob25928a

data_7152536
_publ_section_title
;
 Unexpected reactivity of diaryl \a-diketones with thiazolium carbenes:
 discovery of a novel multicomponent reaction for the facile synthesis of
 1,4-thiazin-3-ones.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6579
_journal_page_last               6586
_journal_paper_doi               10.1039/c2ob25928a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C18 H16 Br N O S'
_chemical_formula_sum            'C18 H16 Br N O S'
_chemical_formula_weight         374.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.300(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0158(5)
_cell_length_b                   9.3261(4)
_cell_length_c                   14.7056(6)
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      4.37
_cell_volume                     1630.66(12)
_computing_cell_refinement       'Denzo-SMN (otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'Denzo-SMN (otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '\f scans and \w 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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9687
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         4.37
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SORTAV (R.H. Blessing, Acta Crystallogr., 1995, A51, 33)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0528P)^2^+0.2560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2242
_reflns_number_total             3147
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c2ob25928a.txt
_cod_data_source_block           16b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152536