Synergistic or antagonistic antioxidant combinations - a case study exploring flavonoid-nitroxide hybrids.
Larin, Astrid C. R.; Pfrunder, Michael C.; Mullen, Kathleen M.; Wiedbrauk, Sandra; Boase, Nathan R.; Fairfull-Smith, Kathryn E; Organic & biomolecular chemistry 21 (2023) 1780–1792; doi:10.1039/d2ob02101c

data_7159123
_publ_section_title
;
 Synergistic or antagonistic antioxidant combinations - a case study
 exploring flavonoid-nitroxide hybrids.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1780
_journal_page_last               1792
_journal_paper_doi               10.1039/d2ob02101c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H23 N O4'
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-07-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-12 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                110.197(4)
_cell_angle_beta                 96.116(3)
_cell_angle_gamma                91.402(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8355(2)
_cell_length_b                   11.8125(5)
_cell_length_c                   14.5365(6)
_cell_measurement_reflns_used    9765
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.4950
_cell_measurement_theta_min      2.7280
_cell_volume                     933.05(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.808
_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    -10.00  86.00   0.50    1.00    --    8.04  37.00  90.00  192
  2  \w     -2.00  81.00   0.50    1.00    --    8.04  57.00 120.00  166
  3  \w    -10.00  69.00   0.50    1.00    --    8.04  57.00   0.00  158
  4  \w     41.00  82.00   0.50    1.00    --    8.04  57.00-180.00   82
  5  \w     -8.00  31.00   0.50    1.00    --    8.04  57.00-180.00   78
  6  \w    -69.00  25.00   0.50    1.00    --    8.04 -37.00-150.00  188
  7  \w     25.00  50.00   0.50    1.00    --   -9.76  57.00  30.00   50
  8  \w    -29.00   1.00   0.50    1.00    --   -9.76  57.00  30.00   60
  9  \w    -20.00   7.00   0.50    1.00    --   -9.76 -57.00 150.00   54
 10  \w    -51.00 -26.00   0.50    1.00    --   -9.76 -57.00 150.00   50
 11  \w    -80.00 -34.00   0.50    1.00    --   -9.76 -37.00 120.00   92
 12  \w    -77.00  -7.00   0.50    1.00    --   -9.76 -37.00-120.00  140
;
_diffrn_measurement_device       'Rigaku Synergy'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0459554000
_diffrn_orient_matrix_UB_12      0.0399773000
_diffrn_orient_matrix_UB_13      0.0415214000
_diffrn_orient_matrix_UB_21      -0.0811492000
_diffrn_orient_matrix_UB_22      0.0171298000
_diffrn_orient_matrix_UB_23      -0.0319142000
_diffrn_orient_matrix_UB_31      -0.0794450000
_diffrn_orient_matrix_UB_32      -0.0471128000
_diffrn_orient_matrix_UB_33      -0.0013206000
_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  0.0489
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         33.178
_diffrn_reflns_theta_min         1.841
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         5749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0634P)^2^+0.1176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4462
_reflns_number_total             5749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02101c2.cif
_cod_data_source_block           18
_cod_depositor_comments
'Adding full bibliography for 7159122--7159125.cif.'
_cod_original_cell_volume        933.04(7)
_cod_database_code               7159123
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         C12O3N1H18
_chemical_oxdiff_usercomment     ' 02ACL1/6 F14-19'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C15(H15), C2(H2), C6(H6), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              70855
_shelx_hkl_checksum              80106
_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 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.782