Synthesis, structure investigation and evaluation of anti-orthopoxvirus activities of 2-(2-arylethenyl)imidazoles
Golfarb-Abramov, Vladislav O.; Kazennova, Anastasia V.; Basanova, Elizaveta I.; Serova, Olga A.; Bormotov, Nikolai I.; Shishkina, Larisa N.; Krasnov, Vyacheslav I.; Polovyanenko, Dmitriy N.; Moskalev, Ivan A.; Fedorov, Alexey Yu.; Arkhipov, Sergey G.; Ilyina, Margarita G.; Borisevich, Sophia S.; Yarovaya, Olga I.; Nikitina, Polina A.; New Journal of Chemistry 49 (2025) 19699–19717; doi:10.1039/D5NJ03203B

data_7064117
_publ_section_title
;
 Synthesis, structure investigation and evaluation of anti-orthopoxvirus
 activities of 2-(2-arylethenyl)imidazoles
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19699
_journal_page_last               19717
_journal_paper_doi               10.1039/D5NJ03203B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C16 H18 N3 O5'
_chemical_formula_sum            'C16 H18 N3 O5'
_chemical_formula_weight         332.33
_chemical_melting_point          432.0(10)
_chemical_name_systematic        Ethyl
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-03 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.796(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7308(9)
_cell_length_b                   38.246(3)
_cell_length_c                   9.089(2)
_cell_measurement_reflns_used    456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5630
_cell_measurement_theta_min      2.4880
_cell_volume                     1633.0(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_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      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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    -65.00 115.00   0.50   94.00    --   25.00   0.00  35.00  360
  2  \w    -65.00  55.00   0.50   94.00    --   25.00   0.00 125.00  240
  3  \w    -65.00  44.50   0.50   94.00    --   25.00 -72.00 185.00  219
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161649000
_diffrn_orient_matrix_UB_12      0.0180043000
_diffrn_orient_matrix_UB_13      -0.0178028000
_diffrn_orient_matrix_UB_21      -0.0160963000
_diffrn_orient_matrix_UB_22      -0.0042005000
_diffrn_orient_matrix_UB_23      -0.0765397000
_diffrn_orient_matrix_UB_31      -0.1491557000
_diffrn_orient_matrix_UB_32      -0.0014968000
_diffrn_orient_matrix_UB_33      0.0007918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11371
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.319
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.93732
_exptl_absorpt_correction_T_min  0.93732
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.84
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0799
_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^)+(0.1558P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2336
_refine_ls_wR_factor_ref         0.2738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1581
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03203b2.cif
_cod_data_source_block           4c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '431-433' was changed to
'432.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7064114--7064119.cif.
;
_cod_original_cell_volume        1632.9(5)
_cod_database_code               7064117
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C17 H16 N3 O5'
_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. Rigid bond restraints
 O5, C13
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 N3, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C7(H7), C6(H6), C2(H2), C5(H5), C3(H3A)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              31685
_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 3.676
_oxdiff_exptl_absorpt_empirical_full_min 0.192