Hydrazineyl-linked imidazole[1,2-a]pyrimidine-thiazole hybrids: design, synthesis, and in vitro biological evaluation studies
P, Dinesha; Naik, Shivakumar; D, Udayakumar; B. C, Revanasiddappa; Ranjan, Venkatesh; Veeranagaiah, Naveena S.; RSC Advances 15 (2025) 32477–32496; doi:10.1039/D5RA04692K

data_7250836
_publ_section_title
;
 Hydrazineyl-linked imidazole[1,2-a]pyrimidine-thiazole hybrids: design,
 synthesis, and in vitro biological evaluation studies
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              32477
_journal_page_last               32496
_journal_paper_doi               10.1039/D5RA04692K
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C21 H20 N6 O3 S'
_chemical_formula_sum            'C21 H20 N6 O3 S'
_chemical_formula_weight         436.49
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2025-06-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-06-05 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.48035(17)
_cell_length_b                   22.48035(17)
_cell_length_c                   17.48441(18)
_cell_measurement_reflns_used    12943
_cell_measurement_temperature    299
_cell_measurement_theta_max      73.7590
_cell_measurement_theta_min      2.8350
_cell_volume                     8836.03(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (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  'SHELXL 2013/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_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     29.00 105.00   0.50    0.71    --  110.01 -95.00 -60.00  152
  2  \w     29.00 105.00   0.50    0.71    --  110.01 -95.00 -60.00  152
  3  \w     35.00  71.00   0.50    0.71    --  110.01 -61.00 -60.00   72
  4  \w     35.00  71.00   0.50    0.71    --  110.01 -61.00  60.00   72
  5  \w     35.00  71.00   0.50    0.71    --  110.01 -61.00  90.00   72
  6  \w   -114.00 -52.00   0.50    0.18    --  -39.42 -77.00-180.00  124
  7  \w    -51.00 -21.00   0.50    0.71    -- -100.00  45.00-180.00   60
  8  \w    -51.00 -21.00   0.50    0.71    -- -100.00  45.00-150.00   60
  9  \w    -71.00 -24.00   0.50    0.71    -- -100.00  61.00-120.00   94
 10  \w    -51.00 -21.00   0.50    0.71    -- -100.00  45.00 -30.00   60
 11  \w    -51.00 -21.00   0.50    0.71    -- -100.00  45.00  90.00   60
 12  \w    -91.00 -24.00   0.50    0.71    -- -100.00 131.00 104.00  134
 13  \w    -96.00 -25.00   0.50    0.71    -- -100.00 139.00 -80.00  142
 14  \w    -90.00 -16.00   0.50    0.18    --  -39.42 131.00 104.00  148
 15  \w    104.00 178.00   0.50    0.71    --  110.01 108.00  27.00  148
 16  \w     63.00 121.00   0.50    0.18    --   39.42 178.00  90.00  116
 17  \w     63.00 121.00   0.50    0.18    --   39.42 178.00 -30.00  116
 18  \w     63.00 121.00   0.50    0.18    --   39.42 178.00 -60.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21613
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.293
_diffrn_reflns_theta_min         3.202
_exptl_absorpt_coefficient_mu    1.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0864P)^2^+3.0403P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3675
_reflns_number_total             4337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04692k2.cif
_cod_data_source_block           ov_dp_1a
_cod_original_cell_volume        8836.03(16)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7250836
_shelxl_version_number           2012-9
_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 Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              63325
_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
;