Water/Alkali-Catalyzed Reactions of Azides with 2-Cyanothioacetamides. Eco-Friendly Synthesis of Monocyclic and Bicyclic 1,2,3-Thiadiazole-4-carbimidamides and 5-Amino-1,2,3-triazole-4-carbothioamides.
Filimonov, Valeriy O.; Dianova, Lidia N.; Beryozkina, Tetyana V.; Mazur, Dmitrii; Beliaev, Nikolai A.; Volkova, Natalia N.; Ilkin, Vladimir G.; Dehaen, Wim; Lebedev, Albert T.; Bakulev, Vasiliy A.; The Journal of organic chemistry 84 (2019) 13430–13446; doi:10.1021/acs.joc.9b01599

data_4034551
_publ_section_title
;
 Water/Alkali-Catalyzed Reactions of Azides with 2-Cyanothioacetamides.
 Eco-Friendly Synthesis of Monocyclic and Bicyclic
 1,2,3-Thiadiazole-4-carbimidamides and
 5-Amino-1,2,3-triazole-4-carbothioamides.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13430
_journal_page_last               13446
_journal_paper_doi               10.1021/acs.joc.9b01599
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C13 H16 F N5 O2 S2'
_chemical_formula_sum            'C13 H16 F N5 O2 S2'
_chemical_formula_weight         357.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-17
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.185(6)
_cell_angle_beta                 108.341(5)
_cell_angle_gamma                112.269(6)
_cell_formula_units_Z            2
_cell_length_a                   8.9035(5)
_cell_length_b                   10.0161(7)
_cell_length_c                   10.3084(7)
_cell_measurement_reflns_used    2728
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.9880
_cell_measurement_theta_min      2.6860
_cell_volume                     799.62(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.8680
_diffrn_measurement_details
;
  1 omega  -14.00   12.00   1.0000    4.6000
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000  -30.0000 26

  2 omega  -21.00   21.00   1.0000    4.6000
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000  120.0000 42

  3 omega   19.00   97.00   1.0000    4.6000
omega____ theta____ kappa____ phi______ frames
    -       23.2924 -156.0000    0.0000 78

  4 omega  -35.00   30.00   1.0000    4.6000
omega____ theta____ kappa____ phi______ frames
    -       23.2924  -57.0000 -150.0000 65

  5 omega   -2.00   96.00   1.0000    4.6000
omega____ theta____ kappa____ phi______ frames
    -       23.2924   38.0000  150.0000 98

  6 omega  -39.00   49.00   1.0000    4.6000
omega____ theta____ kappa____ phi______ frames
    -       23.2924  -38.0000  -30.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0175675000
_diffrn_orient_matrix_UB_12      0.0271205000
_diffrn_orient_matrix_UB_13      0.0691754000
_diffrn_orient_matrix_UB_21      0.0124124000
_diffrn_orient_matrix_UB_22      -0.0631791000
_diffrn_orient_matrix_UB_23      0.0222139000
_diffrn_orient_matrix_UB_31      0.0890256000
_diffrn_orient_matrix_UB_32      0.0352819000
_diffrn_orient_matrix_UB_33      0.0089600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7330
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.75
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0431
_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^)+(0.1050P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                3486
_reflns_number_total             4337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01599_si_004.cif
_cod_data_source_block           exp_884
_cod_original_cell_volume        799.62(9)
_cod_database_code               4034551
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22