A photochemical HAT approach to synthesize <i>N</i>-substituted benzoxazin-4-ones and their activity as AMPA receptor modulators.
Rudik, Daniil I.; Smirnov, Alexander Yu; Bogdanova, Yulia A.; Mikhaylov, Andrey A.; Romanenko, Alexander R.; Korlyukov, Alexander A.; Nikolaev, Maxim; Baranov, Mikhail S.; Ivanov, Dmitrii S.; Organic & biomolecular chemistry 24 (2026) 651–658; doi:10.1039/d5ob01699a

data_7161042
_publ_section_title
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 A photochemical HAT approach to synthesize <i>N</i>-substituted
 benzoxazin-4-ones and their activity as AMPA receptor modulators.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              651
_journal_page_last               658
_journal_paper_doi               10.1039/d5ob01699a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C16 H10 Cl N O4'
_chemical_formula_sum            'C16 H10 Cl N O4'
_chemical_formula_weight         315.70
_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             2025-03-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.02.27 svn.r83f5de2 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-10-10 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.695(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3234(18)
_cell_length_b                   15.735(3)
_cell_length_c                   7.5713(13)
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.23
_cell_volume                     1333.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14733
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.819
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1229 before and 0.1007 after correction.
The Ratio of minimum to maximum transmission is 0.6207.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       cube
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0740P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2050
_reflns_number_total             2944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01699a2.cif
_cod_data_source_block           rd602
_cod_database_code               7161042
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              80788
_shelx_hkl_checksum              89076
_olex2_submission_special_instructions 'No special instructions were received'