Experimental and Computational Investigation of the Oxime Bond Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime
Matveevskaya, Vladislava V.; Pavlov, Dmitry I.; Kovrizhina, Anastasia R.; Sukhikh, Taisiya S.; Sadykov, Evgeniy H.; Dorovatovskii, Pavel V.; Lazarenko, Vladimir A.; Khlebnikov, Andrei I.; Potapov, Andrei S.; Pharmaceutics 15 (2023) 1802–; doi:10.3390/pharmaceutics15071802

data_1569476
_publ_section_title
;
 Experimental and Computational Investigation of the Oxime Bond
 Stereochemistry in c-Jun N-terminal Kinase 3 Inhibitors
 11H-Indeno[1,2-b]quinoxalin-11-one Oxime and Tryptanthrin-6-oxime
;
_journal_issue                   7
_journal_name_full               Pharmaceutics
_journal_page_first              1802
_journal_paper_doi               10.3390/pharmaceutics15071802
_journal_volume                  15
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H9 N3 O2'
_chemical_formula_weight         263.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.614(3)
_cell_length_b                   4.8980(10)
_cell_length_c                   17.322(4)
_cell_measurement_reflns_used    4463
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      1.25
_cell_volume                     1155.1(4)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'ShelXle (H\"ubschle, 2011)'
_computing_publication_material  'CIFTAB (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 12.4
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rayonix SX-165 CCD'
_diffrn_measurement_method       '\f scan'
_diffrn_radiation_monochromator  'Double Crystal Monochromator'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7527
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7050
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        26.848
_diffrn_reflns_theta_max         27.318
_diffrn_reflns_theta_min         1.245
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     1075
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0908P)^2^+0.1903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3075
_reflns_number_total             4249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2249116.cif
_cod_data_source_block           vvm-trfin_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1569476
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              53093
_shelx_hkl_checksum              78028