Synthesis of ciprofloxacin-linked 1,2,3-triazole conjugates as potent antibacterial agents using click chemistry: exploring their function as DNA gyrase inhibitors via in silico- and in vitro-based studies
Patel, Upendra Kumar; Tiwari, Punit; Tilak, Ragini; Joshi, Gaurav; Kumar, Roshan; Agarwal, Alka; RSC Advances 14 (2024) 17051–17070; doi:10.1039/D4RA01332H

data_7248761
_publ_section_title
;
 Synthesis of ciprofloxacin-linked 1,2,3-triazole conjugates as potent
 antibacterial agents using click chemistry: exploring their function as
 DNA gyrase inhibitors via in silico- and in vitro-based studies
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              17051
_journal_page_last               17070
_journal_paper_doi               10.1039/D4RA01332H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C33 H28 Cl F N6 O4'
_chemical_formula_sum            'C33 H28 Cl F N6 O4'
_chemical_formula_weight         627.06
_chemical_melting_point          463.0(10)
_chemical_name_systematic
'(1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl 7-(4-benzoylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate'
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2023-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-10 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                97.2620(10)
_cell_angle_beta                 98.652(2)
_cell_angle_gamma                102.2660(10)
_cell_formula_units_Z            4
_cell_length_a                   11.7334(2)
_cell_length_b                   12.3293(2)
_cell_length_c                   22.1027(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3047.14(9)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58235
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.141
_diffrn_reflns_theta_min         3.719
_exptl_absorpt_coefficient_mu    1.572
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     812
_refine_ls_number_reflns         11919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0655
_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^)+(0.1237P)^2^+0.6558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8348
_reflns_number_total             11919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra01332h2.cif
_cod_data_source_block           cpr-030_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '462-464' was changed to
'463.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7248761
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C016(H016), C01H(H01U)
2.b Secondary CH2 refined with riding coordinates:
 C01D(H01A,H01B), C01E(H01S,H01T), C01J(H01C,H01D), C01L(H01E,H01G), C01M(H01H,
 H01J), C01O(H01K,H01L), C01P(H01M,H01O), C01Q(H01P,H01Q), C01R(H01X,H01Y),
 C01T(H01,H), C01U(H1,HA), C01X(H2,HB), C01Y(H3,HC), C023(H02B,H02C)
2.c Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00T(H00T), C00U(H00U), C00W(H00W), C015(H015), C01B(H01R),
 C01F(H01F), C01I(H01I), C01K(H01V), C01N(H01N), C01W(H01W), C01Z(H01Z),
 C025(H025), C026(H026), C027(H027), C028(H028), C02A(H02A), C02B(H02D),
 C02D(H02E), C02E(H02F), C02F(H02G), C02G(H02K), C02H(H02H), C02I(H02I),
 C02J(H02J), C2(H2A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              77988
_shelx_hkl_checksum              26292
_shelx_fab_checksum              47939
_olex2_submission_special_instructions 'No special instructions were received'