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_7131177
_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 H20 N4 O2 S'
_chemical_formula_sum            'C23 H20 N4 O2 S'
_chemical_formula_weight         416.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-10-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2022-10-28 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.378(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4274(6)
_cell_length_b                   25.1111(16)
_cell_length_c                   14.2863(10)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.82
_cell_volume                     4098.3(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.1103
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            127264
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.397
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7061
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+3.9491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.2077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5598
_reflns_number_total             8390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06708k2.cif
_cod_data_source_block           mo_cjk_b023_0m_pl
_cod_depositor_comments
;
Adding full bibliography for 7131176--7131177.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H40 N8 O4 S2'
_cod_original_formula_weight         832.98
_cod_original_formula_moiety         '2(C23 H20 N4 O2 S)'
_cod_original_formula_units_Z            4
_cod_database_code               7131177
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C26(H26), C29(H29), C42(H42), C31(H31), C30(H30), C35(H35),
 C43(H43), C34(H34), C32(H32), C33(H33), C46(H46), C44(H44), C45(H45), N1(H1),
 C8(H8), C9(H9), C10(H10), C4(H4), C12(H12), C6(H6), C11(H11), C7(H7), C19(H19),
  C20(H20), C3(H3), C23(H23), C21(H21), C22(H22)
2.c X=CH2 refined with riding coordinates:
 C39(H39A,H39B), C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'