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_7248989
_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         'C22 H20 Br N3 O4'
_chemical_formula_sum            'C22 H20 Br N3 O4'
_chemical_formula_weight         470.32
_chemical_name_systematic
3-((2-bromobenzyl)oxy)-6,6-dimethyl-2-(4-nitrophenyl)-3,5,6,7-tetrahydro-4H-benzo[d]imidazol-4-one
_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
_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                78.539(16)
_cell_angle_beta                 77.793(19)
_cell_angle_gamma                77.049(17)
_cell_formula_units_Z            4
_cell_length_a                   9.339(2)
_cell_length_b                   13.222(2)
_cell_length_c                   18.311(4)
_cell_measurement_reflns_used    2031
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      26.2660
_cell_measurement_theta_min      2.7240
_cell_volume                     2126.4(8)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      295(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.896
_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  30.00   1.00  120.00    --    0.00   0.00  45.00  120
  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
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.1519
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16882
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.116
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45652
_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    1.469
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_preparation       'chemical synthesis'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.2227
_refine_ls_R_factor_gt           0.0895
_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^)+(0.1333P)^2^+1.0369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2353
_refine_ls_wR_factor_ref         0.2957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3046
_reflns_number_total             7829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00181h2.cif
_cod_data_source_block           10b_pani189_etoh
_cod_original_cell_volume        2126.5(8)
_cod_database_code               7248989
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.694
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C32(H32A,H32B), C13(H13A,H13B), C35(H35A,H35B), C38(H38A,
 H38B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C6(H6), C18(H18), C5(H5), C27(H27), C25(H25), C40(H40), C19(H19),
 C20(H20), C24(H24), C21(H21), C41(H41), C3(H3), C42(H42), C2(H2), C43(H43)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C36(H36A,H36B,H36C), C15(H15A,H15B,H15C), C37(H37A,H37B,
 H37C)
;
_shelx_res_checksum              51803
_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
;