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#$Date: 2023-07-06 13:45:51 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/94/1569478.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
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data_1569478
loop_
_publ_author_name
'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.'
_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       'ω and φ 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/[σ²(Fo²)+(0.0766P)²+0.2245P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.009
_shelx_estimated_absorpt_t_max   0.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3088(5) 0.82720(9) 0.68033(16) 0.0445(5) Uani 1 1 d . . . . .
H1 H 0.335(11) 0.8281(19) 0.736(4) 0.067 Uiso 1 1 d . U . . .
N1 N 0.5182(5) 0.68016(9) 0.36828(17) 0.0347(5) Uani 1 1 d . . . . .
C1 C 0.7417(6) 0.64347(11) 0.40864(19) 0.0345(6) Uani 1 1 d . . . . .
N2 N 0.7621(5) 0.68715(10) 0.56462(16) 0.0364(5) Uani 1 1 d . . . . .
C2 C 0.8610(6) 0.64687(11) 0.50520(19) 0.0351(6) Uani 1 1 d . . . . .
N3 N 0.4703(6) 0.78080(9) 0.65334(18) 0.0408(6) Uani 1 1 d . . . . .
C3 C 1.0888(6) 0.60826(13) 0.5426(2) 0.0411(7) Uani 1 1 d . . . . .
H3 H 1.171236 0.610376 0.607367 0.049 Uiso 1 1 calc R U . . .
C4 C 1.1928(6) 0.56768(12) 0.4868(3) 0.0443(7) Uani 1 1 d . . . . .
H4 H 1.346409 0.541699 0.513036 0.053 Uiso 1 1 calc R U . . .
C5 C 1.0742(7) 0.56402(12) 0.3905(2) 0.0443(7) Uani 1 1 d . . . . .
H5 H 1.147928 0.535664 0.352203 0.053 Uiso 1 1 calc R U . . .
C6 C 0.8525(6) 0.60137(12) 0.3522(2) 0.0413(6) Uani 1 1 d . . . . .
H6 H 0.773287 0.598853 0.287222 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4309(6) 0.71864(11) 0.42454(18) 0.0336(6) Uani 1 1 d . . . . .
C8 C 0.5538(6) 0.72210(12) 0.52248(19) 0.0347(6) Uani 1 1 d . . . . .
C9 C 0.2046(6) 0.76426(11) 0.4040(2) 0.0343(6) Uani 1 1 d . . . . .
C10 C 0.1869(6) 0.79477(11) 0.4873(2) 0.0358(6) Uani 1 1 d . . . . .
C11 C 0.4024(6) 0.76951(11) 0.5647(2) 0.0371(6) Uani 1 1 d . . . . .
C12 C 0.0261(6) 0.77941(12) 0.3199(2) 0.0391(6) Uani 1 1 d . . . . .
H12 H 0.039528 0.758972 0.263480 0.047 Uiso 1 1 calc R U . . .
C13 C -0.1711(7) 0.82499(12) 0.3207(2) 0.0416(7) Uani 1 1 d . . . . .
H13 H -0.295958 0.835834 0.264118 0.050 Uiso 1 1 calc R U . . .
C14 C -0.1903(7) 0.85504(12) 0.4021(2) 0.0449(7) Uani 1 1 d . . . . .
H14 H -0.329419 0.886017 0.400354 0.054 Uiso 1 1 calc R U . . .
C15 C -0.0119(7) 0.84131(11) 0.4868(2) 0.0405(6) Uani 1 1 d . . . . .
H15 H -0.024402 0.862710 0.542382 0.049 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O1 H1 107(3) . . ?
C7 N1 C1 115.5(2) . . ?
N1 C1 C6 119.0(3) . . ?
N1 C1 C2 121.6(2) . . ?
C6 C1 C2 119.4(2) . . ?
C8 N2 C2 113.8(2) . . ?
N2 C2 C3 118.5(3) . . ?
N2 C2 C1 122.4(2) . . ?
C3 C2 C1 119.1(3) . . ?
C11 N3 O1 112.3(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N1 C7 C8 122.7(3) . . ?
N1 C7 C9 129.3(2) . . ?
C8 C7 C9 108.0(2) . . ?
N2 C8 C7 124.0(3) . . ?
N2 C8 C11 127.7(2) . . ?
C7 C8 C11 108.3(2) . . ?
C12 C9 C10 121.0(3) . . ?
C12 C9 C7 130.4(3) . . ?
C10 C9 C7 108.6(2) . . ?
C15 C10 C9 120.2(3) . . ?
C15 C10 C11 130.7(3) . . ?
C9 C10 C11 109.1(2) . . ?
N3 C11 C8 120.3(3) . . ?
N3 C11 C10 133.7(3) . . ?
C8 C11 C10 106.0(2) . . ?
C13 C12 C9 118.1(3) . . ?
C13 C12 H12 120.9 . . ?
C9 C12 H12 120.9 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 117.6(3) . . ?
C14 C15 H15 121.2 . . ?
C10 C15 H15 121.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.386(3) . ?
O1 H1 0.79(5) . ?
N1 C7 1.305(4) . ?
N1 C1 1.375(4) . ?
C1 C6 1.409(4) . ?
C1 C2 1.414(4) . ?
N2 C8 1.314(4) . ?
N2 C2 1.385(4) . ?
C2 C3 1.404(4) . ?
N3 C11 1.293(4) . ?
C3 C4 1.366(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.436(4) . ?
C7 C9 1.466(4) . ?
C8 C11 1.472(4) . ?
C9 C12 1.391(4) . ?
C9 C10 1.405(4) . ?
C10 C15 1.400(4) . ?
C10 C11 1.481(4) . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
