Ru(II)-catalyzed site-selective <i>N</i>-directed C(sp<sup>2</sup>)-H alkylation of quinoxalinones with maleimide.
Monika, ?; Kumar, Prashant; Singh, Brajendra K.; Organic & biomolecular chemistry 23 (2025) 10743–10752; doi:10.1039/d5ob01524c

data_7160844
_publ_section_title
;
 Ru(II)-catalyzed site-selective <i>N</i>-directed C(sp<sup>2</sup>)-H
 alkylation of quinoxalinones with maleimide.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10743
_journal_page_last               10752
_journal_paper_doi               10.1039/d5ob01524c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H16 F N3 O3'
_chemical_formula_sum            'C20 H16 F N3 O3'
_chemical_formula_weight         365.36
_chemical_name_systematic
3-(5-fluoro-2-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)phenyl)-1-methylpyrrolidine-2,5-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-04-08 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9270(8)
_cell_length_b                   11.3024(5)
_cell_length_c                   20.4930(9)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    224(100)
_cell_measurement_theta_max      31.0240
_cell_measurement_theta_min      1.9740
_cell_volume                     3457.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      224(100)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.793
_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     15.00  40.00   0.50    7.00    --    6.31  82.00   8.00   50
  2  \w     11.00  79.00   0.50    7.00    --    6.31  77.00-101.00  136
  3  \w    -23.00  27.00   0.50    7.00    --   -5.22 -99.00  90.00  100
  4  \w     -7.00  34.00   0.50    7.00    --    6.31 -99.00  90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0133124000
_diffrn_orient_matrix_UB_12      -0.0180812000
_diffrn_orient_matrix_UB_13      0.0505623000
_diffrn_orient_matrix_UB_21      0.0328148000
_diffrn_orient_matrix_UB_22      0.0239173000
_diffrn_orient_matrix_UB_23      0.0131158000
_diffrn_orient_matrix_UB_31      -0.0317419000
_diffrn_orient_matrix_UB_32      0.0172317000
_diffrn_orient_matrix_UB_33      0.0347984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20086
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.705
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.197
_diffrn_reflns_theta_min         1.988
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       cube
_exptl_crystal_F_000             1520
_exptl_crystal_preparation       'SLOW EVAPORATION IN ETHANOL AND CHLOROFORM'
_exptl_crystal_recrystallization_method
'SLOW EVAPORATION IN ETHANOL AND CHLOROFORM'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7915
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0980P)^2^+0.1602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1935
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.613
_reflns_number_gt                5351
_reflns_number_total             7915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01524c2.cif
_cod_data_source_block           3d_auto
_cod_depositor_comments
'Adding full bibliography for 7160843--7160844.cif.'
_cod_database_code               7160844
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     11-01-2025
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.990
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00W(H00W)
2.b Secondary CH2 refined with riding coordinates:
 C00Z(H00A,H00B), C019(H01K,H01L)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00V(H00V), C00Y(H00Y), C012(H012), C014(H014), C015(H015),
 C016(H016), C017(H017), C018(H018), C01A(H01D), C01C(H01M), C01F(H01F),
 C01G(H01G), C01H(H01H)
2.d Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C), C01D(H01N,H01O,H01P), C01E(H01Q,H01R,H01S), C01I(H01E,
 H01I,H01J)
;
_shelx_res_checksum              3109
_olex2_submission_original_sample_id RMS-28
_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 3.676
_oxdiff_exptl_absorpt_empirical_full_min 0.677