Elucidating the mechanism, origin of regioselectivity and substrate scope of structurally diverse 1,2,4-triazoles synthesis via rare type of diazo compounds reactivity
Kuznetsov, Roman; Kantin, Grigory; Sapegin, Alexander; Novikov, Mikhail Sergeevich; Dar'in, Dmitry; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01650A

data_7160877
_publ_section_title
;
 Elucidating the mechanism, origin of regioselectivity and substrate scope
 of structurally diverse 1,2,4-triazoles synthesis via rare type of diazo
 compounds reactivity
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01650A
_journal_year                    2025
_chemical_formula_moiety         'C23 H15 Cl F3 N3 O'
_chemical_formula_sum            'C23 H15 Cl F3 N3 O'
_chemical_formula_weight         441.83
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-09-14 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.207(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1094(9)
_cell_length_b                   4.6693(4)
_cell_length_c                   20.8977(11)
_cell_measurement_reflns_used    8106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.4180
_cell_measurement_theta_min      3.6890
_cell_volume                     1967.6(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  044-265_auto
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15490
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.230
_diffrn_reflns_theta_min         2.191
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.85681
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0770
_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^)+(0.0867P)^2^+1.3702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2953
_reflns_number_total             3983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01650a2.cif
_cod_data_source_block           044-265_auto
_cod_database_code               7160877
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
1.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C20(H20), C2(H2), C11(H11), C17(H17), C16(H16), C3(H3), C14(H14),
 C6(H6), C13(H13), C19(H19), C4(H4), C5(H5)
;
_shelx_res_checksum              20459
_olex2_submission_special_instructions 'No special instructions were received'