Base-mediated ketenimine formation from <i>N</i>-sulfonylthioimidates for the synthesis of 5-amino-1-vinyl/aryl-1,2,3-triazoles.
Chen, Wan-Yu; Lin, Wei-Han; Kuo, Chia-Jou; Liang, Chien-Fu; Chemical communications (Cambridge, England) 59 (2023) 1297–1300; doi:10.1039/d2cc06708k

data_7131176
_publ_section_title
;
 Base-mediated ketenimine formation from <i>N</i>-sulfonylthioimidates for
 the synthesis of 5-amino-1-vinyl/aryl-1,2,3-triazoles.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1297
_journal_page_last               1300
_journal_paper_doi               10.1039/d2cc06708k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H22 N4 O2 S'
_chemical_formula_sum            'C23 H22 N4 O2 S'
_chemical_formula_weight         418.50
_chemical_name_systematic        Triazole_6
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-27
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2022-08-16 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.496(2)
_cell_length_b                   11.4484(18)
_cell_length_c                   25.707(5)
_cell_measurement_reflns_used    2730
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.76
_cell_volume                     4266.2(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.1139
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            105076
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.766
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1760
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.0980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+12.5146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.2433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2275
_reflns_number_total             3669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06708k2.cif
_cod_data_source_block           mo_cwy_3023_pl
_cod_depositor_comments
'Adding full bibliography for 7131176--7131177.cif.'
_cod_database_code               7131176
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C024(H024)
2.b Aromatic/amide H refined with riding coordinates:
 N00L(H00L), C00X(H00X), C01N(H01N), C01O(H01O), C01P(H01P), C01Y(H01Y),
 C022(H022), C023(H023), C02C(H02C), C02K(H02K), C02O(H02O), C02W(H02W),
 C030(H030), C033(H033), C035(H035)
2.c Idealised Me refined as rotating group:
 C02N(H02A,H02B,H02D), C031(H03A,H03B,H03C)
;
_olex2_submission_special_instructions 'No special instructions were received'