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_7251598
_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 syn
_chemical_formula_moiety         'C33 H32 N4 O11'
_chemical_formula_sum            'C33 H32 N4 O11'
_chemical_formula_weight         660.62
_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             2025-06-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-09 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                82.636(2)
_cell_angle_beta                 87.2760(10)
_cell_angle_gamma                80.538(2)
_cell_formula_units_Z            1
_cell_length_a                   5.79480(10)
_cell_length_b                   11.9278(2)
_cell_length_c                   12.1042(2)
_cell_measurement_reflns_used    8296
_cell_measurement_temperature    298
_cell_measurement_theta_max      67.7130
_cell_measurement_theta_min      3.6680
_cell_volume                     818.14(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.994
_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    -35.00  24.00   0.50    0.20    --   40.83 -11.00-180.00  118
  2  \w     44.00 127.00   0.50    0.20    --   96.04-145.00   0.00  166
  3  \w     41.00 100.00   0.50    0.20    --   40.83-138.00 -90.00  118
  4  \w    -28.00  68.00   0.50    0.20    --   40.83 -77.00 -30.00  192
  5  \w    -31.00  28.00   0.50    0.20    --   40.83 -21.00  30.00  118
  6  \w      3.00  76.00   0.50    0.20    --   40.83-101.00 170.00  146
  7  \w     25.00 107.00   0.50    0.20    --   96.04-101.00 170.00  164
  8  \w     23.00 106.00   0.50    0.20    --   96.04 -96.00 120.00  166
  9  \w     32.00 110.00   0.50    0.20    --   96.04-117.00  60.00  156
 10  \w     23.00 106.00   0.50    0.20    --   96.04 -96.00  60.00  166
 11  \w     32.00 110.00   0.50    0.20    --   96.04-117.00   0.00  156
 12  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00 150.00   56
 13  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00 120.00   56
 14  \w     27.00 105.00   0.50    0.20    --   96.04 -77.00  60.00  156
 15  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00  90.00   56
 16  \w     27.00 105.00   0.50    0.20    --   96.04 -77.00 -60.00  156
 17  \w     28.00  83.00   0.50    0.20    --   96.04 -68.00-120.00  110
 18  \w     27.00 105.00   0.50    0.20    --   96.04 -77.00-180.00  156
 19  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00-180.00   56
 20  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00-150.00   56
 21  \w     29.00  57.00   0.50    0.20    --   96.04 -50.00-120.00   56
 22  \w    105.00 170.00   0.50    0.20    --   96.04  96.00 150.00  130
 23  \w     99.00 160.00   0.50    0.20    --   96.04 117.00 120.00  122
 24  \w     81.00 164.00   0.50    0.20    --   96.04 145.00  90.00  166
 25  \w     99.00 160.00   0.50    0.20    --   96.04 117.00 -90.00  122
 26  \w    106.00 168.00   0.50    0.20    --   96.04 101.00 -85.00  124
 27  \w     99.00 160.00   0.50    0.20    --   96.04 117.00-150.00  122
 28  \w     69.00 165.00   0.50    0.20    --   96.04  77.00-180.00  192
 29  \w     69.00 165.00   0.50    0.20    --   96.04  77.00-120.00  192
 30  \w     74.00 163.00   0.50    0.20    --   96.04  59.00 -90.00  178
 31  \w     74.00 163.00   0.50    0.20    --   96.04  59.00-150.00  178
 32  \w     81.00 166.00   0.50    0.20    --   96.04  25.00-150.00  170
 33  \w     81.00 166.00   0.50    0.20    --   96.04  25.00-120.00  170
 34  \w    -28.00  31.00   0.50    0.20    --  -40.83  21.00 -90.00  118
 35  \w    -24.00  35.00   0.50    0.20    --  -40.83  11.00-150.00  118
 36  \w    -97.00 -19.00   0.50    0.20    --  -40.83 138.00 -90.00  156
 37  \w    -97.00 -19.00   0.50    0.20    --  -40.83 138.00  30.00  156
 38  \w    -84.00 -18.00   0.50    0.20    --  -82.50 117.00  60.00  132
 39  \w    -24.00  35.00   0.50    0.20    --  -40.83  11.00  60.00  118
 40  \w    -76.00  19.00   0.50    0.20    --  -40.83 101.00 -85.00  190
 41  \w    -81.00 -11.00   0.50    0.20    --  -82.50 101.00 -85.00  140
 42  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -30.00   64
 43  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00-180.00   64
 44  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -90.00   64
 45  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  90.00   64
 46  \w   -150.00 -69.00   0.50    0.20    --  -82.50 -33.00   0.00  162
 47  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 120.00  190
 48  \w   -154.00 -84.00   0.50    0.20    --  -82.50-101.00 170.00  140
 49  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00  60.00  190
 50  \w   -107.00 -24.00   0.50    0.20    --  -40.83 -43.00  90.00  166
 51  \w   -108.00 -17.00   0.50    0.20    --  -40.83 -65.00 -30.00  182
 52  \w   -108.00 -17.00   0.50    0.20    --  -40.83 -65.00-120.00  182
 53  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00-180.00  190
;
_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      -0.1009884000
_diffrn_orient_matrix_UB_12      0.0779756000
_diffrn_orient_matrix_UB_13      0.0885502000
_diffrn_orient_matrix_UB_21      -0.0205510000
_diffrn_orient_matrix_UB_22      -0.1064163000
_diffrn_orient_matrix_UB_23      0.0843330000
_diffrn_orient_matrix_UB_31      0.2491447000
_diffrn_orient_matrix_UB_32      0.0000141000
_diffrn_orient_matrix_UB_33      0.0390931000
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11155
_diffrn_reflns_point_group_measured_fraction_full 0.715
_diffrn_reflns_point_group_measured_fraction_max 0.713
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.963
_diffrn_reflns_theta_min         3.683
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85679
_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 grayish gray'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0500P)^2^+0.0521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.434
_reflns_Friedel_fraction_full    0.434
_reflns_Friedel_fraction_max     0.432
_reflns_number_gt                4083
_reflns_number_total             4237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09700b2.cif
_cod_data_source_block           rk7-38_auto
_cod_database_code               7251598
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.771
_diffrn_oxdiff_ac3_digest_hkl    4103b6c1d7907cb202d7268fdb14551c831e4f
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N)
1.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C011(H01A,H01B)
1.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00V(H00V), C00W(H00W), C010(H010), C012(H012), C014(H014),
 C015(H015), C017(H017), C018(H018), C019(H019), C01C(H01O)
1.d Idealised Me refined as rotating group:
 C013(H01C,H01D,H01E), C016(H01F,H01G,H01H), C01A(H01I,H01J,H01K), C01B(H01L,
 H01M,H01N)
;
_shelx_res_checksum              59337
_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.870