Access to N-thioalkenyl and N-(o-thio)aryl-Benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C-O Bond Cleavage of an Alkoxide.
Andreoli, Federico; Kaid-Slimane, Radia; Coppola, Fabien; Farran, Daniel; Roussel, Christian; Vanthuyne, Nicolas; The Journal of organic chemistry  (2015) 150311084704007–; doi:10.1021/acs.joc.5b00221

data_4030800
_publ_section_title
;
 Access to N-thioalkenyl and N-(o-thio)aryl-Benzimidazol-2-ones by Ring
 Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts
 and C-O Bond Cleavage of an Alkoxide.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              150311084704007
_journal_paper_doi               10.1021/acs.joc.5b00221
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H16 N2 O S'
_chemical_formula_sum            'C17 H16 N2 O S'
_chemical_formula_weight         296.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-07-10T10:46:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 116.651(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6227(3)
_cell_length_b                   11.7212(2)
_cell_length_c                   16.6110(2)
_cell_measurement_reflns_used    28030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.03
_cell_measurement_theta_min      2.17
_cell_measurement_wavelength     0.71073
_cell_volume                     3066.61(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28030
_diffrn_reflns_theta_full        29.03
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+1.0354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                5493
_reflns_number_total             7930
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo5b00221_si_002.cif
_cod_data_source_block           df09
_cod_original_cell_volume        3066.61(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4030800