Pyrimido[5,4-<i>e</i>]azolo[1,5-<i>a</i>]pyrimidines and pyrimido[4,5-<i>e</i>][1,2,4]triazolo[5,1-<i>c</i>][1,2,4]triazines: <i>one-pot</i> multi-component synthesis and cytotoxic activity.
Bersneva, Eva V.; Savateev, Konstantin V.; Slepukhin, Pavel A.; Melekhin, Vsevolod V.; Tokhtueva, Maria D.; Rusinov, Vladimir L.; Organic & biomolecular chemistry 23 (2025) 1945–1960; doi:10.1039/d4ob01853b

data_7160331
_publ_section_title
;
 Pyrimido[5,4-<i>e</i>]azolo[1,5-<i>a</i>]pyrimidines and
 pyrimido[4,5-<i>e</i>][1,2,4]triazolo[5,1-<i>c</i>][1,2,4]triazines:
 <i>one-pot</i> multi-component synthesis and cytotoxic activity.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1945
_journal_page_last               1960
_journal_paper_doi               10.1039/d4ob01853b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C11 H14 N8 S'
_chemical_formula_sum            'C11 H14 N8 S'
_chemical_formula_weight         290.36
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-18
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.0522(13)
_cell_length_b                   7.5876(12)
_cell_length_c                   28.440(4)
_cell_measurement_reflns_used    1671
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.2590
_cell_measurement_theta_min      2.8560
_cell_volume                     2816.6(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9184
_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      6.00  91.00   1.00  100.00    --   21.40  38.00 -90.00   85
  2  \w     -7.00  93.00   1.00  100.00    --   21.40  19.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169019000
_diffrn_orient_matrix_UB_12      0.0157409000
_diffrn_orient_matrix_UB_13      -0.0233674000
_diffrn_orient_matrix_UB_21      -0.0173273000
_diffrn_orient_matrix_UB_22      -0.0848417000
_diffrn_orient_matrix_UB_23      -0.0066533000
_diffrn_orient_matrix_UB_31      -0.0486884000
_diffrn_orient_matrix_UB_32      0.0356473000
_diffrn_orient_matrix_UB_33      -0.0057123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11951
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.86
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0026(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1891
_refine_ls_R_factor_gt           0.0828
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2670
_reflns_number_gt                1446
_reflns_number_total             3957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob01853b2.cif
_cod_data_source_block           exp_1520
_cod_depositor_comments          'Adding full bibliography for 7160331.cif.'
_cod_original_cell_volume        2816.5(6)
_cod_database_code               7160331
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.786