2-Aryl-1-hydroxyimidazoles possessing antiviral activity against wide range of orthopoxviruses including Variola virus.
Basanova, Elizaveta Ivanovna; Kulikova, Ekaterina; Bormotov, Nikolai I.; Serova, Olga; Shishkina, Larisa; Ovchinnikova, Alyona; Odnoshevskiy, Dmitry; Pyankov, Oleg; Agafonov, Alexander; Yarovaya, Olga; Borisevich, Sophia; Ilyina, Margarita; Kolybalov, Dmitry; Arkhipov, Sergey; Bogdanov, Nikita; Pavlova, Marina A.; Salakhutdinov, Nariman; Perevalov, Valery P.; Nikitina, Polina A.; RSC Medicinal Chemistry  (2024) –; doi:10.1039/D4MD00181H

data_7248986
_publ_section_title
;
 2-Aryl-1-hydroxyimidazoles possessing antiviral activity against wide
 range of orthopoxviruses including Variola virus.
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00181H
_journal_year                    2024
_chemical_formula_moiety         '2(C13 H11 F3 N2 O2), H2 O'
_chemical_formula_sum            'C26 H24 F6 N4 O5'
_chemical_formula_weight         586.49
_chemical_name_systematic
'1-(1-hydroxy-4-methyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazol-5-yl)ethan-1-one 4-acetyl-5-methyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide hydrate'
_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   mixed
_audit_creation_date             2024-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                91.342(6)
_cell_angle_beta                 101.399(5)
_cell_angle_gamma                97.183(6)
_cell_formula_units_Z            2
_cell_length_a                   9.7912(6)
_cell_length_b                   11.5563(9)
_cell_length_c                   12.0456(8)
_cell_measurement_reflns_used    3981
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      26.2020
_cell_measurement_theta_min      2.4200
_cell_volume                     1323.97(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.931
_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    -90.00  90.00   1.00   60.00    --    0.00   0.00  45.00  180
  2  \w    -30.00  90.00   1.00   60.00    --    0.00  72.00  45.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Tongda TD-5000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13672
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.141
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Nitromethane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5051
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0697P)^2^+0.2179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3762
_reflns_number_total             5051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00181h2.cif
_cod_data_source_block           semihydrate_4c_pani114_ch3no2
_cod_database_code               7248986
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 F5A-F6A
 2.116 with sigma of 0.04
 F4B-F6B
 2.116 with sigma of 0.04
 F5B-F6B
 2.116 with sigma of 0.04
 F6A-F4A
 2.116 with sigma of 0.04
 F4A-F5A
 2.116 with sigma of 0.04
 F5B-F4B
 2.116 with sigma of 0.04
3. Rigid bond restraints
 F4B, F5A, F6B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F4A, F6A, F5B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(F4B)=Sof(F6B)=Sof(F5A)=1-FVAR(1)
 Sof(F4A)=Sof(F5B)=Sof(F6A)=FVAR(1)
5.a Free rotating group:
 O5(H5B,H5C)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2AB(H2AB), C3A(H3A), C2A(H2A), C5AB(H5AB), C6AB(H6AB), C3AB(H3AB),
 C5A(H5A), C6A(H6A)
5.c Idealised Me refined as rotating group:
 C8B(H8BA,H8BB,H8BC), C8(H8A,H8B,H8C), C7B(H7BA,H7BB,H7BC), C7(H7A,H7B,H7C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3B(H3B)
;
_shelx_res_checksum              47617
_olex2_submission_original_sample_id PANI-114_CH3NO2
_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
;