Electro-oxidative C–H alkylation of quinoxalin-2(1H)-ones with organoboron compounds
Niu, Kaikai; Hao, Yanke; Song, Lingyun; Liu, Yuxiu; Wang, Qingmin; Green Chemistry 23 (2021) 302–306; doi:10.1039/D0GC03892J

data_7241887
_publ_section_title
;
 Electro-oxidative C--H alkylation of quinoxalin-2(1H)-ones with
 organoboron compounds
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              302
_journal_page_last               306
_journal_paper_doi               10.1039/D0GC03892J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C15 H16 F2 N2 O'
_chemical_formula_sum            'C15 H16 F2 N2 O'
_chemical_formula_weight         278.30
_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             2020-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-12 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.9820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.85240(10)
_cell_length_b                   12.04300(10)
_cell_length_c                   12.43970(10)
_cell_measurement_reflns_used    8896
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.7950
_cell_measurement_theta_min      4.8650
_cell_volume                     1358.85(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      294.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.977
_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    -84.00  38.00   0.50    0.50    --    5.00 -72.00  40.00  244
  2  \w   -139.00 -16.00   0.50    0.50    --  -49.60 -72.00  40.00  246
  3  \w   -199.00 -77.00   0.50    2.00    -- -110.00 -72.00  40.00  244
  4  \w   -139.00 -16.00   0.50    0.50    --  -49.60 -72.00   0.00  246
  5  \w    -79.00  40.00   0.50    0.50    --  -49.60  57.00 -90.00  238
  6  \w   -199.00 -81.00   0.50    2.00    -- -110.00 -57.00  90.00  236
  7  \w   -199.00 -79.00   0.50    2.00    -- -110.00 -38.00  60.00  240
  8  \w   -139.00 -21.00   0.50    2.00    -- -110.00  57.00-180.00  236
  9  \w   -199.00 -59.00   0.50    2.00    -- -110.00 -19.00  90.00  280
 10  \w   -141.00 -21.00   0.50    2.00    -- -110.00  38.00 -30.00  240
 11  \w   -199.00 -79.00   0.50    2.00    -- -110.00 -38.00 150.00  240
 12  \w   -199.00 -81.00   0.50    2.00    -- -110.00 -57.00-150.00  236
 13  \w   -199.00-104.00   0.50    2.00    -- -110.00 -57.00 120.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1386440000
_diffrn_orient_matrix_UB_12      0.0275875000
_diffrn_orient_matrix_UB_13      0.1092856000
_diffrn_orient_matrix_UB_21      0.0815575000
_diffrn_orient_matrix_UB_22      -0.0983162000
_diffrn_orient_matrix_UB_23      -0.0271060000
_diffrn_orient_matrix_UB_31      0.0545387000
_diffrn_orient_matrix_UB_32      0.0770352000
_diffrn_orient_matrix_UB_33      -0.0736360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14345
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.373
_diffrn_reflns_theta_min         4.876
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0027(4)
_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   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0595P)^2^+0.1686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2623
_reflns_number_total             2879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03892j2.cif
_cod_data_source_block           p20200606a
_cod_depositor_comments          'Adding full bibliography for 7241887.cif.'
_cod_database_code               7241887
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 98.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              23083
_shelx_hkl_checksum              8605
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 4.131
_oxdiff_exptl_absorpt_empirical_full_min 0.620