Utility of 6-aza-2-thiothymine in the synthesis of novel [1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one derivatives: synthesis, structure elucidation, molecular docking and in vitro anti-lung cancer activity
Kamel, Monica G.; Sroor, Farid M.; Mahmoud, Khaled; Shafey, Heba I.; Hassaneen, Hamdi M.; Vendier, Laure; RSC Advances 15 (2025) 6015–6031; doi:10.1039/D4RA08958H

data_7250042
_publ_section_title
;
 Utility of 6-aza-2-thiothymine in the synthesis of novel
 [1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one derivatives: synthesis,
 structure elucidation, molecular docking and in vitro anti-lung cancer
 activity
;
_journal_issue                   8
_journal_name_full               'RSC Advances'
_journal_page_first              6015
_journal_page_last               6031
_journal_paper_doi               10.1039/D4RA08958H
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C13 H13 N6 O3'
_chemical_formula_sum            'C13 H13 N6 O3'
_chemical_formula_weight         301.28
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2024-10-11 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.314(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0047(3)
_cell_length_b                   21.1874(6)
_cell_length_c                   8.0296(3)
_cell_measurement_reflns_used    35544
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.42
_cell_measurement_theta_min      4.16
_cell_volume                     1319.53(8)
_computing_cell_refinement
; 
 CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)
;
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction
; 
 CrysAlisPro 1.171.42.102a (Rigaku OD, 2023) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_unetI/netI     0.041
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            46395
_diffrn_reflns_theta_full        77.610
_diffrn_reflns_theta_max         80.010
_diffrn_reflns_theta_min         4.173
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bloc
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9825
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.0006291
_refine_ls_shift/su_mean         0.0000597
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 0.59P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1294
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1294
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2742
_reflns_number_total             2843
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0433
_oxford_refine_ls_scale          5.74(19)
_oxford_reflns_number_all        2840
_cod_data_source_file            d4ra08958h2.cif
_cod_data_source_block           PT1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1319.53(9)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               7250042
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0433
_oxford_refine_ls_wr_factor_all  0.1294