Unusual C<sub>3</sub>-acetylation of quinoxalin-2(1<i>H</i>)-one <i>via</i> oxidative C-C and C-O bond cleavages of PEG-400.
Kudale, Vishal Suresh; Mutra, Mohana Reddy; Chu, Ching-Piao; Wang, Jeh-Jeng; Organic & biomolecular chemistry 19 (2021) 5567–5571; doi:10.1039/d1ob00769f

data_7158102
_publ_section_title
;
 Unusual C<sub>3</sub>-acetylation of quinoxalin-2(1<i>H</i>)-one
 <i>via</i> oxidative C-C and C-O bond cleavages of PEG-400.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5567
_journal_page_last               5571
_journal_paper_doi               10.1039/d1ob00769f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H12 Cl2 N2 O2'
_chemical_formula_sum            'C17 H12 Cl2 N2 O2'
_chemical_formula_weight         347.18
_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             2020-05-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.70700(10)
_cell_length_b                   17.6134(2)
_cell_length_c                   22.5179(2)
_cell_measurement_reflns_used    34871
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0120
_cell_measurement_theta_min      2.1410
_cell_volume                     3052.29(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_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    -79.00  36.00   0.50    5.65    --   10.60 -77.00   0.00  230
  2  \w    -20.00 100.00   0.50    5.65    --   10.60  57.00-150.00  240
  3  \w    -17.00 100.00   0.50    5.65    --   10.60  82.00-150.00  234
  4  \w    -17.00 100.00   0.50    5.65    --   10.60  82.00-150.00  234
  5  \w    -79.00  41.00   0.50    5.65    --   10.60 -57.00   0.00  240
  6  \w   -100.00  17.00   0.50    5.65    --  -10.90 -82.00  30.00  234
  7  \w    -79.00  38.00   0.50    5.65    --   10.60 -82.00 150.00  234
  8  \w    -15.00 100.00   0.50    5.65    --   10.60  77.00 -30.00  230
  9  \w    -79.00 -54.00   0.50    5.65    --   10.60 -57.00 -90.00   50
 10  \w    -36.00  79.00   0.50    5.65    --  -10.90  77.00-120.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089302000
_diffrn_orient_matrix_UB_12      -0.0325750000
_diffrn_orient_matrix_UB_13      -0.0180949000
_diffrn_orient_matrix_UB_21      0.0195485000
_diffrn_orient_matrix_UB_22      0.0235939000
_diffrn_orient_matrix_UB_23      -0.0242821000
_diffrn_orient_matrix_UB_31      0.0896420000
_diffrn_orient_matrix_UB_32      -0.0018840000
_diffrn_orient_matrix_UB_33      0.0088250000
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.039
_diffrn_reflns_theta_min         2.149
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0342P)^2^+1.4144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5716
_reflns_number_total             6459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00769f2.cif
_cod_data_source_block           k10905-jjw-c
_cod_depositor_comments
;
Adding full bibliography for 7158102--7158103.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H24 Cl4 N4 O4'
_cod_original_formula_weight         694.37
_cod_original_formula_moiety         '2(C17 H12 Cl2 N2 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               7158102
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H22 N2 O2 Cl2'
_diffrn_oxdiff_digest_frames
;
01529f3da72ce609e168521cc37e37332e000254cd8
;
_diffrn_oxdiff_digest_hkl
;
01ba08c94d5461a4b41e335418e23a0a18ff17
;
_reflns_odcompleteness_completeness 99.54
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24B,H24A)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C19(H19),
 C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C29(H29)
2.c Idealised Me refined as rotating group:
 C17(H17C,H17A,H17B), C34(H34C,H34A,H34B)
;
_shelx_res_checksum              75159
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.813