Electro-oxidative C‒H azolation of quinoxalin-2(1H)-ones
Niu, Kaikai; Ding, Ling; Zhou, Pan; Hao, Yanke; Liu, Yuxiu; Song, Hongjian; Wang, Qingmin; Green Chemistry 23 (2021) 3246–3249; doi:10.1039/D1GC00861G

data_7242664
_publ_section_title
;
 Electro-oxidative C--H azolation of quinoxalin-2(1H)-ones
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3246
_journal_page_last               3249
_journal_paper_doi               10.1039/D1GC00861G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C12 H10 N4 O, 0.5(H2 O)'
_chemical_formula_sum            'C12 H11 N4 O1.5'
_chemical_formula_weight         235.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-12 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.096(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0472(7)
_cell_length_b                   7.0440(3)
_cell_length_c                   16.9293(8)
_cell_measurement_reflns_used    9309
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.5340
_cell_measurement_theta_min      2.2660
_cell_volume                     2139.96(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  \w   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0011321000
_diffrn_orient_matrix_UB_12      -0.0466918000
_diffrn_orient_matrix_UB_13      -0.0347007000
_diffrn_orient_matrix_UB_21      -0.0105687000
_diffrn_orient_matrix_UB_22      0.0860081000
_diffrn_orient_matrix_UB_23      -0.0189438000
_diffrn_orient_matrix_UB_31      0.0407782000
_diffrn_orient_matrix_UB_32      0.0235498000
_diffrn_orient_matrix_UB_33      0.0003944000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9092
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         2.270
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0092(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0526P)^2^+1.9817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1828
_reflns_number_total             2181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc00861g2.cif
_cod_data_source_block           r20201010a
_cod_depositor_comments          'Adding full bibliography for 7242664.cif.'
_cod_original_formula_sum        'C12 H11 N4 O1.50'
_cod_database_code               7242664
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Others
 Fixed Sof: O2(0.5) H2A(0.5) H2B(0.5)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              19296
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.815