Ligand-free palladium-catalyzed synthesis of 3-(2,2-dialkyl-2<i>H</i>-chromen-4-yl)-2-phenylimidazo[1,2-<i>a</i>]pyridine derivatives: molecular docking investigation of their potential as DNA gyrase inhibitors and evaluation of their antibacterial activities.
Mishra, Rudra Narayan; Ahemad, Mohammed Ansar; Panda, Jasmine; Nayak, Sabita; Mohapatra, Seetaram; Sahoo, Chita Ranjan; RSC advances 15 (2025) 2930–2946; doi:10.1039/d4ra09092f

data_7249881
_publ_section_title
;
 Ligand-free palladium-catalyzed synthesis of
 3-(2,2-dialkyl-2<i>H</i>-chromen-4-yl)-2-phenylimidazo[1,2-<i>a</i>]pyridine
 derivatives: molecular docking investigation of their potential as DNA
 gyrase inhibitors and evaluation of their antibacterial activities.
;
_journal_issue                   4
_journal_name_full               'RSC advances'
_journal_page_first              2930
_journal_page_last               2946
_journal_paper_doi               10.1039/d4ra09092f
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         '0.133(C25 H21 Cl N2 O)'
_chemical_formula_sum            'C3.33 H2.8 Cl0.13 N0.27 O0.13'
_chemical_formula_weight         53.45
_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             2024-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-12 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                83.912(5)
_cell_angle_beta                 69.508(5)
_cell_angle_gamma                81.211(6)
_cell_formula_units_Z            15
_cell_length_a                   9.4927(7)
_cell_length_b                   10.3632(7)
_cell_length_c                   11.6644(6)
_cell_measurement_reflns_used    12042
_cell_measurement_temperature    206(30)
_cell_measurement_theta_max      77.2270
_cell_measurement_theta_min      4.0550
_cell_volume                     1060.54(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      206(30)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_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   -106.00 -35.00   0.50    0.38    --  -38.50 -34.00  87.00  142
  2  \w    -42.00  29.00   0.50    0.38    --  -38.50  34.00-115.00  142
  3  \w     46.00 116.00   0.50    0.38    --   49.06  34.00-115.00  140
  4  \w    -18.00  52.00   0.50    0.38    --   49.06 -34.00  87.00  140
  5  \w    104.00 174.00   0.50    1.50    --  106.83  34.00-115.00  140
  6  \w     40.00 110.00   0.50    1.50    --  106.83 -34.00  87.00  140
  7  \w    -86.00  -6.00   0.50    0.38    --  -38.50 125.00-180.00  160
  8  \w    -15.00  72.00   0.50    0.38    --   49.06 -77.00   0.00  174
  9  \w     46.00 115.00   0.50    0.38    --   49.06  38.00   0.00  138
 10  \w    -17.00  52.00   0.50    0.38    --   49.06 -38.00 -30.00  138
 11  \w     46.00 115.00   0.50    0.38    --   49.06  38.00 -90.00  138
 12  \w     44.00 120.00   0.50    1.50    --  106.83 -61.00-180.00  152
 13  \w     39.00 106.00   0.50    1.50    --  106.83 -94.00 120.00  134
 14  \w    103.00 171.00   0.50    1.50    --  106.83  77.00  90.00  136
 15  \w     44.00 112.00   0.50    1.50    --  106.83-125.00  30.00  136
 16  \w     39.00 115.00   0.50    1.50    --  106.83 -15.00  90.00  152
 17  \w     39.00 106.00   0.50    1.50    --  106.83 -94.00 150.00  134
 18  \w     39.00 110.00   0.50    1.50    --  106.83 -30.00 -30.00  142
 19  \w     97.00 170.00   0.50    1.50    --  106.83 125.00  60.00  146
 20  \w     42.00 111.00   0.50    1.50    --  106.83 -45.00  30.00  138
 21  \w    103.00 171.00   0.50    1.50    --  106.83  77.00-180.00  136
 22  \w     94.00 170.00   0.50    1.50    --  106.83  61.00 120.00  152
 23  \w     39.00 106.00   0.50    1.50    --  106.83 -94.00-150.00  134
 24  \w    104.00 175.00   0.50    1.50    --  106.83  30.00  60.00  142
 25  \w     44.00 120.00   0.50    1.50    --  106.83 -61.00  30.00  152
 26  \w     39.00 106.00   0.50    1.50    --  106.83 -94.00 -90.00  134
 27  \w     40.00 107.00   0.50    1.50    --  106.83 -97.00 -34.47  134
 28  \w    103.00 171.00   0.50    1.50    --  106.83  77.00-150.00  136
 29  \w     39.00 106.00   0.50    1.50    --  106.83 -94.00  60.00  134
 30  \w     97.00 170.00   0.50    1.50    --  106.83 125.00 120.00  146
 31  \w   -101.00 -23.00   0.50    0.38    --  -38.50 -64.00  38.52  156
 32  \w     38.00 112.00   0.50    0.38    --   49.06  57.00 -60.00  148
 33  \w     38.00 112.00   0.50    0.38    --   49.06  57.00-180.00  148
 34  \w     38.00 112.00   0.50    0.38    --   49.06  57.00 150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0363139000
_diffrn_orient_matrix_UB_12      0.1361337000
_diffrn_orient_matrix_UB_13      -0.0576198000
_diffrn_orient_matrix_UB_21      0.1431841000
_diffrn_orient_matrix_UB_22      0.0430119000
_diffrn_orient_matrix_UB_23      0.0104300000
_diffrn_orient_matrix_UB_31      0.0930942000
_diffrn_orient_matrix_UB_32      -0.0481437000
_diffrn_orient_matrix_UB_33      -0.1285121000
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16645
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.681
_diffrn_reflns_theta_min         4.052
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0744P)^2^+0.1169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3973
_reflns_number_total             4380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra09092f2.cif
_cod_data_source_block           pcrsd-rnm08_auto
_cod_original_cell_volume        1060.54(13)
_cod_original_formula_sum        'C3.33 H2.80 Cl0.13 N0.27 O0.13'
_cod_database_code               7249881
_shelx_shelxl_version_number     SHELXL'2018/3'
_chemical_oxdiff_formula         'C H N O Cl'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00E), C00R(H00J,H00L,H00O), C00T(H00R,H00T,H00U)
;
_shelx_res_checksum              99522
_shelx_hkl_checksum              19595
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.671