Synthesis, crystal structure, and antiviral evaluation of new imidazopyridine-schiff base derivatives: in vitro and in silico anti-HIV studies
Azzouzi, Mohamed; Ouchaoui, Abderrahim Ait; Azougagh, Omar; El Hadad, Salah Eddine; Abou-salama, Mohamed; Oussaid, Adyl; Pannecouque, Christophe; Rohand, Taoufik; RSC Advances 14 (2024) 36902–36918; doi:10.1039/D4RA07561G

data_7249600
_publ_section_title
;
 Synthesis, crystal structure, and antiviral evaluation of new
 imidazopyridine-schiff base derivatives: in vitro and in silico anti-HIV
 studies
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              36902
_journal_page_last               36918
_journal_paper_doi               10.1039/D4RA07561G
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C20 H13 Cl N4 O2'
_chemical_formula_sum            'C20 H13 Cl N4 O2'
_chemical_formula_weight         376.79
_chemical_name_systematic
(E)-N-(6-chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)-1-(4-nitrophenyl)methanimine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2l8kt8
_audit_creation_date             2023-11-14
_audit_creation_method
;FinalCif V130 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-10-16 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.178(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7755(6)
_cell_length_b                   26.7963(15)
_cell_length_c                   12.0718(6)
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    150
_cell_measurement_theta_max      78.275
_cell_measurement_theta_min      3.562
_cell_volume                     3407.2(3)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            114388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         79.153
_diffrn_reflns_theta_min         3.561
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  0.3293
_exptl_absorpt_correction_T_min  0.2094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.6359.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_recrystallization_method 'crystallized from CHCl3'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         11104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.9569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9165
_reflns_number_total             11104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07561g2.cif
_cod_data_source_block           azzo051
_cod_database_code               7249600
_olex2_date_sample_data_collection 2023-11-13
_olex2_date_sample_submission    2023-11-10
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id MFU-MA-05
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              94774