Synthesis of stable class 5 mesoionic benzo[<i>c</i>]tetrazolo[2,3-<i>a</i>]cinnolinium thiolate, dicyanomethylide, and amides.
Nakata, Mirai; Hirashita, Tsunehisa; Konishi, Yoshikazu; Araki, Shuki; Organic & biomolecular chemistry 21 (2023) 4282–4289; doi:10.1039/d3ob00362k

data_7159328
_publ_section_title
;
 Synthesis of stable class 5 mesoionic
 benzo[<i>c</i>]tetrazolo[2,3-<i>a</i>]cinnolinium thiolate,
 dicyanomethylide, and amides.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4282
_journal_page_last               4289
_journal_paper_doi               10.1039/d3ob00362k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C13 H8 N4 S'
_chemical_formula_sum            'C13 H8 N4 S'
_chemical_formula_weight         252.29
_chemical_name_common            benzo[c]tetrazolo[2,3-a]cinnoline-2-thione
_chemical_name_systematic        benzo[c]tetrazolo[2,3-a]cinnolinium-2-thiolate
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-12-29 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.3963(7)
_cell_length_b                   9.7124(9)
_cell_length_c                   12.0714(10)
_cell_measurement_reflns_used    8048
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.69
_cell_volume                     1101.64(16)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9761
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             520.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol/dichloromethane'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.210
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1152 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0197P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0653
_reflns_number_gt                1762
_reflns_number_total             2475
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3ob00362k2.cif
_cod_data_source_block           496_p_1_a
_cod_depositor_comments          'Adding full bibliography for 7159328.cif.'
_cod_database_code               7159328