Non-innocent pyridyl nitrogens: unprecedented interconversion of N-bridgehead-thiadiazolium salts and thiatriazine in the generation of thiatriazinyl
Alicea A. Leitch; Ilia Korobkov; Abdeljalil Assoud; Jaclyn L. Brusso; Chem.Commun. 50 (2014) 4934–; doi:10.1039/C4CC01433B

data_7112614
_publ_section_title
;
 Non-innocent pyridyl nitrogens: unprecedented interconversion of
 N-bridgehead-thiadiazolium salts and thiatriazine in the generation of
 thiatriazinyl
;
_journal_name_full               Chem.Commun.
_journal_page_first              4934
_journal_paper_doi               10.1039/C4CC01433B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C14 H9 F6 N5 O6 S4'
_chemical_formula_weight         585.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.7192(17)
_cell_angle_beta                 78.5886(16)
_cell_angle_gamma                83.6975(17)
_cell_formula_units_Z            2
_cell_length_a                   8.4770(3)
_cell_length_b                   10.1380(3)
_cell_length_c                   12.6490(4)
_cell_measurement_reflns_used    452
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      1.5
_cell_volume                     1059.12(6)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker Kappa APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Direct Method'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'Omega and phi scan'
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            16882
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9032
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.232
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0166P)^2^+2.2024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                3639
_reflns_number_total             4339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc01433b2.cif
_cod_data_source_block           double5_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112614
_shelxl_version_number           2013-4
_shelx_res_checksum              21958