Direct access to acylated quinoxalin-2(1H)-one N-oxides enabled by the Cu(i)/TBHP system
Xu, Jianxiong; Gong, Xue; Wu, Zhirui; Huang, Weimin; Li, Jizhen; New Journal of Chemistry 49 (2025) 3843–3848; doi:10.1039/D4NJ04823G

data_7063647
_publ_section_title
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 Direct access to acylated quinoxalin-2(1H)-one N-oxides enabled by the
 Cu(i)/TBHP system
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3843
_journal_page_last               3848
_journal_paper_doi               10.1039/D4NJ04823G
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C16 H11 Cl N2 O3, 0.5[CHCl3]'
_chemical_formula_sum            'C16.5 H11.5 Cl2.5 N2 O3'
_chemical_formula_weight         374.40
_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             2024-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-18 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5686(2)
_cell_length_b                   9.5602(2)
_cell_length_c                   29.2255(5)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    180.00
_cell_measurement_theta_max      62.363
_cell_measurement_theta_min      3.043
_cell_volume                     3211.64(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            40667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        62.371
_diffrn_reflns_theta_max         62.371
_diffrn_reflns_theta_min         3.043
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.571
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1202 before and 0.0807 after correction.
The Ratio of minimum to maximum transmission is 0.7037.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       needle
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.00196(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0690P)^2^+3.4520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3820
_reflns_number_total             5099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04823g3.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7063647.cif.'
_cod_original_formula_sum        'C16.50 H11.50 Cl2.50 N2 O3'
_cod_database_code               7063647
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.804
_shelx_estimated_absorpt_t_min   0.658
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C22(H22), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
1.b Idealised Me refined as rotating group:
 C7(H7B,H7A,H7C), C25(H25A,H25B,H25C)
;
_smtbx_masks_special_details
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A solvent mask was calculated and 220 electrons were 
found in a volume of 484\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[CHCl3] per formula unit 
which account for 232 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              21983
_shelx_hkl_checksum              86146
_shelx_fab_checksum              48768
_olex2_submission_special_instructions 'No special instructions were received'