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_1569478
_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_formula_sum            'C15 H9 N3 O'
_chemical_formula_weight         247.2556
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual-space
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.8120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.49610(10)
_cell_length_b                   23.1804(4)
_cell_length_c                   14.3978(3)
_cell_measurement_reflns_used    4413
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.51
_cell_measurement_theta_min      3.65
_cell_volume                     1482.85(5)
_computing_cell_refinement       'SAINT (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4268
_diffrn_reflns_point_group_measured_fraction_full 0.781
_diffrn_reflns_point_group_measured_fraction_max 0.781
_diffrn_reflns_theta_full        66.438
_diffrn_reflns_theta_max         66.438
_diffrn_reflns_theta_min         3.645
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.170000
_exptl_crystal_size_mid          0.100000
_exptl_crystal_size_min          0.050000
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 687 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.2245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.563
_reflns_Friedel_fraction_max     0.563
_reflns_number_gt                1983
_reflns_number_total             2054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2249117.cif
_cod_data_source_block           iq1a_mi_a_sq
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               1569478
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.009
_shelx_estimated_absorpt_t_max   0.014
_shelx_res_checksum              22028
_shelx_hkl_checksum              83685
_shelx_fab_checksum              91063