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_7251597
_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_formula_moiety         'C33 H31 Cl N4 O11'
_chemical_formula_sum            'C33 H31 Cl N4 O11'
_chemical_formula_weight         695.07
_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             2025-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-18 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                81.389(3)
_cell_angle_beta                 80.238(3)
_cell_angle_gamma                86.153(3)
_cell_formula_units_Z            1
_cell_length_a                   5.8670(2)
_cell_length_b                   12.0575(4)
_cell_length_c                   12.1900(4)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.9370
_cell_measurement_theta_min      3.7070
_cell_volume                     839.50(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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   -101.00 -75.00   0.50    2.49    --  -40.83 149.00-102.00   52
  2  \w    -82.00 -57.00   0.50    2.49    --  -40.83 124.00  94.00   50
  3  \w    -47.00 -20.00   0.50    2.49    --  -40.83 124.00  94.00   54
  4  \w    -93.00 -67.00   0.50    2.49    --  -40.83-149.00-148.00   52
  5  \w    -53.00 -28.00   0.50    2.49    --  -40.83 149.00-102.00   50
  6  \w     37.00  64.00   0.50    2.49    --   40.83-124.00  14.00   54
  7  \w     71.00  97.00   0.50    2.49    --   40.83-149.00-148.00   52
  8  \w   -100.00 -74.00   0.50    9.95    --  -82.50-124.00  14.00   52
  9  \w    -86.00 -58.00   0.50    9.95    --  -82.50-149.00-148.00   56
 10  \w    -52.00 -27.00   0.50    9.95    --  -82.50 124.00  94.00   50
 11  \w     85.00 111.00   0.50    9.95    --  104.00-124.00  14.00   52
 12  \w     64.00  89.00   0.50    9.95    --  104.00-149.00-148.00   50
 13  \w    107.00 132.00   0.50    9.95    --  104.00 124.00  94.00   50
 14  \w    -48.00 -16.00   0.50    2.49    --  -40.83 -77.00-180.00   64
 15  \w    -18.00  19.00   0.50    2.49    --  -40.83  65.00  90.00   74
 16  \w   -100.00 -68.00   0.50    2.49    --  -40.83 -32.00 150.00   64
 17  \w   -109.00 -84.00   0.50    2.49    --  -40.83 -77.00-180.00   50
 18  \w    -85.00 -26.00   0.50    2.49    --  -40.83 -43.00-120.00  118
 19  \w    -65.00 -28.00   0.50    2.49    --  -40.83 -32.00 150.00   74
 20  \w    -63.00 -36.00   0.50    2.49    --  -40.83  65.00  90.00   54
 21  \w    -28.00  19.00   0.50    2.49    --   40.83 -11.00 -30.00   94
 22  \w    -27.00  24.00   0.50    2.49    --   40.83 -11.00-120.00  102
 23  \w    -21.00   6.00   0.50    2.49    --   40.83 -21.00 120.00   54
 24  \w   -125.00 -65.00   0.50    9.95    --  -82.50 -68.00  60.00  120
 25  \w   -153.00-122.00   0.50    9.95    --  -82.50 -87.00 120.00   62
 26  \w   -117.00 -78.00   0.50    9.95    --  -82.50 -87.00 120.00   78
 27  \w    -89.00 -64.00   0.50    9.95    --  -82.50 149.00-102.00   50
 28  \w    -47.00 -15.00   0.50    9.95    --  -82.50  42.00 150.00   64
 29  \w    -50.00 -25.00   0.50    9.95    --  -82.50  50.00 120.00   50
 30  \w    -46.00 -21.00   0.50    9.95    --  -82.50  42.00   0.00   50
 31  \w    -78.00 -38.00   0.50    9.95    --  -82.50 111.00-120.00   80
 32  \w    -47.00 -22.00   0.50    9.95    --  -82.50  42.00-180.00   50
 33  \w    126.00 158.00   0.50    9.95    --  104.00  42.00 120.00   64
 34  \w     87.00 117.00   0.50    9.95    --  104.00-133.00  90.00   60
 35  \w     36.00  79.00   0.50    9.95    --  104.00 -68.00 150.00   86
 36  \w     98.00 141.00   0.50    9.95    --  104.00  68.00-180.00   86
 37  \w     45.00  95.00   0.50    9.95    --  104.00-111.00-120.00  100
 38  \w     42.00 108.00   0.50    9.95    --  104.00-111.00 -90.00  132
 39  \w    142.00 168.00   0.50    9.95    --  104.00  68.00-180.00   52
 40  \w     57.00  82.00   0.50    9.95    --  104.00 -77.00-120.00   50
 41  \w     83.00 108.00   0.50    9.95    --  104.00-111.00-180.00   50
 42  \w     34.00  74.00   0.50    9.95    --  104.00 -93.00 120.00   80
 43  \w     35.00  87.00   0.50    9.95    --  104.00 -77.00 -30.00  104
 44  \w     89.00 140.00   0.50    9.95    --  104.00  25.00  30.00  102
 45  \w     38.00  63.00   0.50    9.95    --  104.00 -59.00 -60.00   50
 46  \w     86.00 121.00   0.50    9.95    --  104.00  17.00 -90.00   70
 47  \w     36.00  90.00   0.50    9.95    --  104.00 -87.00  60.00  108
 48  \w     99.00 172.00   0.50    9.95    --  104.00  59.00 -90.00  146
 49  \w     56.00  81.00   0.50    9.95    --  104.00 -68.00  30.00   50
 50  \w     77.00 118.00   0.50    9.95    --  104.00-133.00   0.00   82
 51  \w     41.00  67.00   0.50    9.95    --  104.00-133.00   0.00   52
 52  \w    128.00 161.00   0.50    9.95    --  104.00  77.00-150.00   66
 53  \w    116.00 171.00   0.50    9.95    --  104.00  77.00 150.00  110
 54  \w    147.00 172.00   0.50    9.95    --  104.00  25.00  60.00   50
 55  \w     98.00 131.00   0.50    9.95    --  104.00  25.00  60.00   66
 56  \w     90.00 115.00   0.50    9.95    --  104.00  68.00-120.00   50
 57  \w    137.00 167.00   0.50    9.95    --  104.00  68.00-120.00   60
 58  \w     42.00  78.00   0.50    9.95    --  104.00 -68.00  60.00   72
 59  \w    115.00 159.00   0.50    9.95    --  104.00  93.00 -60.00   88
 60  \w     78.00 104.00   0.50    9.95    --  104.00  77.00-150.00   52
 61  \w     50.00  75.00   0.50    9.95    --  104.00 -68.00   0.00   50
 62  \w     64.00  95.00   0.50    9.95    --  104.00 178.00  30.00   62
 63  \w     36.00  61.00   0.50    9.95    --  104.00 -59.00 -90.00   50
 64  \w     35.00 105.00   0.50    9.95    --  104.00 -77.00 120.00  140
 65  \w     38.00  63.00   0.50    9.95    --  104.00-111.00 120.00   50
 66  \w     82.00 107.00   0.50    9.95    --  104.00-111.00 120.00   50
 67  \w     69.00  94.00   0.50    9.95    --  104.00 -93.00 150.00   50
 68  \w     38.00  64.00   0.50    9.95    --  104.00 -59.00-120.00   52
 69  \w     43.00  68.00   0.50    9.95    --  104.00 -68.00 -60.00   50
 70  \w     82.00 170.00   0.50    9.95    --  104.00  68.00 -30.00  176
 71  \w     68.00  99.00   0.50    9.95    --  104.00-111.00 -30.00   62
 72  \w     40.00  65.00   0.50    9.95    --  104.00 -59.00 -30.00   50
 73  \w     98.00 123.00   0.50    9.95    --  104.00 149.00-102.00   50
;
_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      0.2167177000
_diffrn_orient_matrix_UB_12      -0.0425691000
_diffrn_orient_matrix_UB_13      -0.0749254000
_diffrn_orient_matrix_UB_21      -0.0864382000
_diffrn_orient_matrix_UB_22      0.0649254000
_diffrn_orient_matrix_UB_23      -0.1049418000
_diffrn_orient_matrix_UB_31      0.1291545000
_diffrn_orient_matrix_UB_32      0.1034514000
_diffrn_orient_matrix_UB_33      0.0122445000
_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  0.0758
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7523
_diffrn_reflns_point_group_measured_fraction_full 0.627
_diffrn_reflns_point_group_measured_fraction_max 0.628
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.711
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44081
_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 brownish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.028
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0905
_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^)+(0.1904P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2669
_refine_ls_wR_factor_ref         0.2917
_reflns_Friedel_coverage         0.265
_reflns_Friedel_fraction_full    0.262
_reflns_Friedel_fraction_max     0.263
_reflns_number_gt                2966
_reflns_number_total             3851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09700b2.cif
_cod_data_source_block           rk-5-16_autored
_cod_database_code               7251597
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.957
_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:
 C20(H20), C24(H24), C21(H21), C23(H23), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C19(H19), C14(H14), C7(H7), C6(H6), C4(H4), C15(H15),
 C11(H11), C5(H5)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C)
;
_shelx_res_checksum              1959
_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 2.647
_oxdiff_exptl_absorpt_empirical_full_min 0.181