Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides.
Goulart, Tales A. C.; Kazmirski, João A G; Back, Davi F.; Zeni, Gilson; The Journal of organic chemistry 84 (2019) 14113–14126; doi:10.1021/acs.joc.9b02276

data_4033618
_publ_section_title
;
 Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III)
 Chloride and Diorganyl Diselenides.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14113
_journal_page_last               14126
_journal_paper_doi               10.1021/acs.joc.9b02276
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H15 Cl N2 S Se'
_chemical_formula_sum            'C22 H15 Cl N2 S Se'
_chemical_formula_weight         453.83
_chemical_melting_point          415
_chemical_name_common
'chlorophenyl phenylselanyl benzo imidazo thiazine'
_chemical_name_systematic
;
4-(4-chlorophenyl)-3-(phenylselanyl)-2H-benzo[4,5]imidazo[2,1-b][1,3]thiazine
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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             2019-08-01T15:00:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.023(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.999(3)
_cell_length_b                   7.392(3)
_cell_length_c                   21.647(12)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.089
_cell_measurement_theta_min      2.835
_cell_volume                     954.6(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17266
_diffrn_reflns_theta_full        29.2
_diffrn_reflns_theta_max         29.2
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    2.225
_exptl_absorpt_correction_T_max  0.8148
_exptl_absorpt_correction_T_min  0.3866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0180(10)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4879
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0187P)^2^+0.0788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                4525
_reflns_number_total             4879
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo9b02276_si_003.cif
_cod_data_source_block           p21_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '415K' was changed to '415' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033616--4033618.cif.
;
_cod_database_code               4033618