Catalyst-free efficient synthesis of functionalized 1,2,4-triazole <i>via</i> ring opening/cyclization of arylidene thiazolone with aryl/alkyl-hydrazine.
Kumari, Akanksha; Jain, Anshul; Sharma, Himani; Sermadurai, Selvakumar; Rana, Nirmal K.; Chemical communications (Cambridge, England) 61 (2025) 11029–11032; doi:10.1039/d5cc02145f

data_7134722
_publ_section_title
;
 Catalyst-free efficient synthesis of functionalized 1,2,4-triazole
 <i>via</i> ring opening/cyclization of arylidene thiazolone with
 aryl/alkyl-hydrazine.
;
_journal_issue                   59
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11029
_journal_page_last               11032
_journal_paper_doi               10.1039/d5cc02145f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C28 H23 N5'
_chemical_formula_sum            'C28 H23 N5'
_chemical_formula_weight         429.528
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-11-01 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.41(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.901(2)
_cell_length_b                   8.4370(15)
_cell_length_c                   23.343(5)
_cell_measurement_reflns_used    4548
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4110
_cell_measurement_theta_min      3.3480
_cell_volume                     2333.4(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8764
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -54.00  31.00   1.00   46.00    --   18.33 -35.00  43.00   85
  2  \w      5.00  83.00   1.00   46.00    --   18.33  35.00-159.00   78
  3  \w     25.00  53.00   1.00   46.00    --  -19.42  35.00-159.00   28
  4  \w    -62.00 -36.00   1.00   46.00    --  -19.42 -35.00  43.00   26
  5  \w     44.00  94.00   1.00   46.00    --   18.33 178.00  60.00   50
  6  \w    -40.00  -7.00   1.00   46.00    --  -19.42 -77.00 -30.00   33
  7  \w    -43.00  20.00   1.00   46.00    --  -19.42  77.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0173463000
_diffrn_orient_matrix_UB_12      0.0195148000
_diffrn_orient_matrix_UB_13      0.0274950000
_diffrn_orient_matrix_UB_21      0.0509808000
_diffrn_orient_matrix_UB_22      -0.0326776000
_diffrn_orient_matrix_UB_23      0.0133748000
_diffrn_orient_matrix_UB_31      0.0266675000
_diffrn_orient_matrix_UB_32      0.0747959000
_diffrn_orient_matrix_UB_33      -0.0012965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.8764
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16067
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.8764
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.95
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       cube
_exptl_crystal_F_000             904.315
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3320
_refine_diff_density_min         -0.3142
_refine_diff_density_rms         0.0634
_refine_ls_d_res_high            0.7341
_refine_ls_d_res_low             6.8726
_refine_ls_extinction_coef       0.0053(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0593
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0593
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.7743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1892
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -14
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                3536
_reflns_number_total             5411
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc02145f2.cif
_cod_data_source_block           SK-RBL-27_auto
_cod_depositor_comments          'Adding full bibliography for 7134722.cif.'
_cod_database_code               7134722
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00P(H00P), C00O(H00O), C00K(H00K), C00D(H00D), C00J(H00J),
 C00T(H00T), C00R(H00R), C00N(H00N), C00I(H00I), C00U(H00U), C00V(H00V),
 C00X(H00X), C00W(H00W), C00M(H00M), C00H(H00H), C00L(H00L), C00S(H00S),
 C00Q(H00Q), C00G(H00G), N004(H004)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.505
_oxdiff_exptl_absorpt_empirical_full_min 0.488