Design, synthesis, structural characterization, anticancer evaluation, and computational studies of novel quinoline-1,2,3-triazole glycohybrids
Kumar, Ravendra; Chauhan, Deepanshi; Gupta, Rakesh Kumar; Dubey, Pawan K.; Kushwaha, Divya; RSC Advances 16 (2026) 8466–8486; doi:10.1039/D5RA09700B

data_7251599
_publ_section_title
;
 Design, synthesis, structural characterization, anticancer evaluation,
 and computational studies of novel quinoline-1,2,3-triazole glycohybrids
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              8466
_journal_page_last               8486
_journal_paper_doi               10.1039/D5RA09700B
_journal_volume                  16
_journal_year                    2026
_chemical_absolute_configuration unk
_chemical_formula_moiety         '0.333(C34 H34 N4 O11)'
_chemical_formula_sum            'C11.33 H11.33 N1.33 O3.67'
_chemical_formula_weight         224.88
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-22
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                81.207(3)
_cell_angle_beta                 80.608(3)
_cell_angle_gamma                86.419(4)
_cell_formula_units_Z            3
_cell_length_a                   5.8582(3)
_cell_length_b                   12.1432(5)
_cell_length_c                   12.2488(4)
_cell_measurement_reflns_used    5158
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.5990
_cell_measurement_theta_min      3.6660
_cell_volume                     848.93(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -62.00 -28.00   0.50    1.00    --  -40.83 155.00 -86.00   68
  2  \w    -74.00 -48.00   0.50    1.00    --  -40.83 120.00 117.00   52
  3  \w    -40.00 -14.00   0.50    1.00    --  -40.83 120.00 117.00   52
  4  \w    -77.00 -52.00   0.50    1.00    --  -40.83-155.00-123.00   50
  5  \w     78.00 103.00   0.50    1.00    --   40.83-155.00-123.00   50
  6  \w     40.00  65.00   0.50    1.00    --   40.83-120.00  33.00   50
  7  \w   -124.00 -98.00   0.50    4.00    --  -82.50-155.00-123.00   52
  8  \w    -67.00 -42.00   0.50    4.00    --  -82.50 155.00 -86.00   50
  9  \w   -122.00 -96.00   0.50    4.00    --  -82.50-120.00  33.00   52
 10  \w     94.00 119.00   0.50    4.00    --  104.00 155.00 -86.00   50
 11  \w    133.00 158.00   0.50    4.00    --  104.00 120.00 117.00   50
 12  \w     91.00 132.00   0.50    4.00    --  104.00-155.00-123.00   82
 13  \w     64.00  89.00   0.50    4.00    --  104.00-120.00  33.00   50
 14  \w    -23.00  35.00   0.50    1.00    --  -40.83  11.00-150.00  116
 15  \w    -60.00 -29.00   0.50    1.00    --  -40.83 -32.00  30.00   62
 16  \w   -109.00 -74.00   0.50    1.00    --  -40.83 -32.00  30.00   70
 17  \w    -94.00 -29.00   0.50    1.00    --  -40.83 138.00-120.00  130
 18  \w    -17.00  31.00   0.50    1.00    --  -40.83  21.00 -30.00   96
 19  \w    -29.00  22.00   0.50    1.00    --  -40.83  32.00-120.00  102
 20  \w     63.00 108.00   0.50    1.00    --   40.83  43.00  90.00   90
 21  \w     26.00  57.00   0.50    1.00    --   40.83  21.00  30.00   62
 22  \w     -3.00  22.00   0.50    1.00    --   40.83 -11.00 120.00   50
 23  \w     87.00 112.00   0.50    1.00    --   40.83  21.00  30.00   50
 24  \w     38.00  77.00   0.50    1.00    --   40.83-104.00  30.00   78
 25  \w    -28.00  21.00   0.50    1.00    --   40.83 -21.00-150.00   98
 26  \w     24.00  52.00   0.50    1.00    --   40.83  43.00  90.00   56
 27  \w    -47.00 -15.00   0.50    4.00    --  -82.50  42.00-180.00   64
 28  \w    -60.00 -14.00   0.50    4.00    --  -82.50  59.00 -30.00   92
 29  \w   -148.00-102.00   0.50    4.00    --  -82.50-111.00  90.00   92
 30  \w   -128.00 -90.00   0.50    4.00    --  -82.50 -68.00  90.00   76
 31  \w   -137.00 -80.00   0.50    4.00    --  -82.50 -87.00 150.00  114
 32  \w    -70.00 -45.00   0.50    4.00    --  -82.50 120.00 117.00   50
 33  \w    -43.00 -16.00   0.50    4.00    --  -82.50  50.00 120.00   54
 34  \w     36.00  61.00   0.50    4.00    --  104.00 -59.00  90.00   50
 35  \w     37.00  68.00   0.50    4.00    --  104.00 -59.00  60.00   62
 36  \w    104.00 164.00   0.50    4.00    --  104.00  93.00 150.00  120
 37  \w     56.00  81.00   0.50    4.00    --  104.00 -68.00  90.00   50
 38  \w     85.00 133.00   0.50    4.00    --  104.00 -87.00  30.00   96
 39  \w     67.00  93.00   0.50    4.00    --  104.00-133.00 120.00   52
 40  \w     42.00  69.00   0.50    4.00    --  104.00-108.00  -1.57   54
 41  \w     40.00  66.00   0.50    4.00    --  104.00-133.00-120.00   52
 42  \w     79.00 117.00   0.50    4.00    --  104.00-133.00-120.00   76
 43  \w     80.00 116.00   0.50    4.00    --  104.00  68.00  30.00   72
 44  \w     36.00  68.00   0.50    4.00    --  104.00 -59.00-150.00   64
 45  \w     93.00 118.00   0.50    4.00    --  104.00-133.00 -90.00   50
 46  \w     50.00  75.00   0.50    4.00    --  104.00-133.00 -90.00   50
 47  \w     38.00  66.00   0.50    4.00    --  104.00-133.00 120.00   56
 48  \w     80.00 105.00   0.50    4.00    --  104.00 -77.00-150.00   50
 49  \w     96.00 173.00   0.50    4.00    --  104.00  25.00 120.00  154
 50  \w     89.00 118.00   0.50    4.00    --  104.00  42.00-180.00   58
 51  \w     95.00 169.00   0.50    4.00    --  104.00  33.00 150.00  148
 52  \w     57.00  82.00   0.50    4.00    --  104.00-111.00  30.00   50
 53  \w    102.00 170.00   0.50    4.00    --  104.00 111.00-180.00  136
 54  \w    114.00 140.00   0.50    4.00    --  104.00 178.00   0.00   52
 55  \w     49.00  74.00   0.50    4.00    --  104.00 -77.00-150.00   50
 56  \w     43.00 114.00   0.50    4.00    --  104.00-133.00   0.00  142
 57  \w    125.00 151.00   0.50    4.00    --  104.00  42.00-180.00   52
 58  \w     37.00  66.00   0.50    4.00    --  104.00 -59.00 120.00   58
 59  \w     37.00  99.00   0.50    4.00    --  104.00 -77.00-180.00  124
 60  \w     93.00 171.00   0.50    4.00    --  104.00  50.00-120.00  156
 61  \w     70.00  96.00   0.50    4.00    --  104.00 178.00   0.00   52
 62  \w     38.00 117.00   0.50    4.00    --  104.00-133.00  30.00  158
 63  \w     39.00  65.00   0.50    4.00    --  104.00 -68.00 -90.00   52
 64  \w     36.00  61.00   0.50    4.00    --  104.00 -59.00-120.00   50
 65  \w     73.00 114.00   0.50    4.00    --  104.00-133.00  90.00   82
 66  \w    126.00 151.00   0.50    4.00    --  104.00  68.00  30.00   50
 67  \w    117.00 142.00   0.50    4.00    --  104.00 111.00  60.00   50
 68  \w     93.00 134.00   0.50    4.00    --  104.00  50.00 -90.00   82
 69  \w     84.00 109.00   0.50    4.00    --  104.00-108.00  -1.57   50
 70  \w     62.00  89.00   0.50    4.00    --  104.00-133.00 150.00   54
 71  \w     77.00 147.00   0.50    4.00    --  104.00  77.00-180.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1622998000
_diffrn_orient_matrix_UB_12      -0.0326656000
_diffrn_orient_matrix_UB_13      -0.0758767000
_diffrn_orient_matrix_UB_21      0.0287155000
_diffrn_orient_matrix_UB_22      -0.1233788000
_diffrn_orient_matrix_UB_23      0.0503661000
_diffrn_orient_matrix_UB_31      -0.2097336000
_diffrn_orient_matrix_UB_32      0.0146736000
_diffrn_orient_matrix_UB_33      0.0911365000
_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  0.0879
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8284
_diffrn_reflns_point_group_measured_fraction_full 0.607
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.099
_diffrn_reflns_theta_min         3.686
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish gray'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.4(6)
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0908
_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^)+(0.1891P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2972
_refine_ls_wR_factor_ref         0.3171
_reflns_Friedel_coverage         0.207
_reflns_Friedel_fraction_full    0.215
_reflns_Friedel_fraction_max     0.206
_reflns_number_gt                2787
_reflns_number_total             4008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09700b2.cif
_cod_data_source_block           rk-5-17_auto
_cod_database_code               7251599
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.775
_diffrn_oxdiff_ac3_digest_hkl    41c3440cca6339d4738a4d71ff69cf286225e8
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C23(H23), C27(H27), C21(H21), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C20(H20), C4(H4), C9(H9), C11(H11), C8(H8), C14(H14), C6(H6),
 C15(H15), C7(H7)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C29(H29A,H29B,H29C), C25(H25A,H25B,H25C), C32(H32A,H32B,
 H32C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              47303
_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 3.022
_oxdiff_exptl_absorpt_empirical_full_min 0.185