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_7248988
_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         'C16 H15 N3 O2'
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31
_chemical_name_systematic
'2-(4-cyanophenyl)-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-benzo[d]imidazole 3-oxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-03-15
_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                90
_cell_angle_beta                 93.696(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7707(9)
_cell_length_b                   24.525(3)
_cell_length_c                   10.1461(17)
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    298(4)
_cell_measurement_theta_max      27.6550
_cell_measurement_theta_min      3.2140
_cell_volume                     1433.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.878
_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  120.00    --    0.00   0.00  45.00  180
  2  \w    -90.00  30.00   1.00  120.00    --    0.00 -72.00 225.00  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  0.0904
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.228
_diffrn_reflns_theta_min         2.176
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       'chemical synthesis'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0661P)^2^+0.1471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1807
_reflns_number_total             3107
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00181h2.cif
_cod_data_source_block           3b_pani164_etoh
_cod_original_cell_volume        1432.9(4)
_cod_database_code               7248988
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3-N3
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C5(H5B,H5C), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C6A(H6A), C3A(H3A), C5A(H5A)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              22912
_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
;