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_7159125
_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         'C34 H34 N2 O6'
_chemical_formula_sum            'C34 H34 N2 O6'
_chemical_formula_weight         566.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-12 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6810(17)
_cell_length_b                   20.795(4)
_cell_length_c                   17.362(4)
_cell_measurement_reflns_used    949
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.126
_cell_measurement_theta_min      1.173
_cell_volume                     3133.4(11)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34216
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.126
_diffrn_reflns_theta_min         1.173
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  'Value not reported by XDS'
_exptl_absorpt_correction_T_min  'Value not reported by XDS'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 3841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     768
_refine_ls_number_reflns         10534
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0801
_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^)+(0.1788P)^2^+0.1390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2142
_refine_ls_wR_factor_ref         0.2280
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                9046
_reflns_number_total             10534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02101c2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7159122--7159125.cif.'
_cod_database_code               7159125
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.996
_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. Restrained distances
 C59-C66A \\sim C59-C66B
 with sigma of 0.02
 C67A-C66B \\sim C67B-C66B
 with sigma of 0.02
 C59-C67A \\sim C59-C67B
 with sigma of 0.02
 C45A-C52A \\sim C45B-C52B
 with sigma of 0.04
 C50B-C51A \\sim C50B-C51B
 with sigma of 0.02
 C50B-C49A \\sim C50B-C49B
 with sigma of 0.02
 N3A-C45A \\sim N3B-C45B
 with sigma of 0.04
 C51A-C46A \\sim C51B-C46B
 with sigma of 0.02
 C46A-C47A \\sim C46B-C47B
 with sigma of 0.02
 C47A-C44A \\sim C47B-C44B
 with sigma of 0.04
 C46A-C45A \\sim C46B-C45B
 with sigma of 0.02
 C48A-C44A \\sim C48B-C44B
 with sigma of 0.04
 C46A-C48A \\sim C46B-C48B
 with sigma of 0.04
 N3A-O10A \\sim N3B-O10B
 with sigma of 0.02
 N3A-C54A \\sim N3B-C54B
 with sigma of 0.04
 N3A-C47A \\sim N3B-C47B
 with sigma of 0.02
 N3A-C53A \\sim N3B-C53B
 with sigma of 0.04
 N3A-C44A \\sim N3B-C44B
 with sigma of 0.02
 C49A-C45A \\sim C49B-C45B
 with sigma of 0.04
 O10A-C47A \\sim O10B-C47B
 with sigma of 0.04
 C49A-C48A \\sim C49B-C48B
 with sigma of 0.02
 C54A-C47A \\sim C54B-C47B
 with sigma of 0.02
 C55A-C47A \\sim C55B-C47B
 with sigma of 0.02
 C46A-C44A \\sim C46B-C44B
 with sigma of 0.04
 N3A-C55A \\sim N3B-C55B
 with sigma of 0.04
 N3A-C52A \\sim N3B-C52B
 with sigma of 0.04
 C45A-C48A \\sim C45B-C48B
 with sigma of 0.02
 C45A-C44A \\sim C45B-C44B
 with sigma of 0.02
 C52A-C44A \\sim C52B-C44B
 with sigma of 0.02
 C54A-C55A \\sim C54B-C55B
 with sigma of 0.04
 C44A-C53A \\sim C44B-C53B
 with sigma of 0.02
 O10A-C44A \\sim O10B-C44B
 with sigma of 0.04
 C47A-C45A \\sim C47B-C45B
 with sigma of 0.04
 C50B-C46A \\sim C50B-C46B
 with sigma of 0.04
 C50B-C48A \\sim C50B-C48B
 with sigma of 0.04
 C45A-C53A \\sim C45B-C53B
 with sigma of 0.04
 C51A-C47A \\sim C51B-C47B
 with sigma of 0.04
 C51A-C45A \\sim C51B-C45B
 with sigma of 0.04
 C52A-C53A \\sim C52B-C53B
 with sigma of 0.04
 C46A-N3A \\sim C46B-N3B
 with sigma of 0.04
 C46A-C54A \\sim C46B-C54B
 with sigma of 0.04
 C46A-C55A \\sim C46B-C55B
 with sigma of 0.04
 C13-C21A \\sim C13-C21B
 with sigma of 0.02
 C13-C20A \\sim C13-C20B
 with sigma of 0.02
3. Others
 Sof(C48B)=Sof(H48B)=Sof(C46B)=Sof(C51B)=Sof(H51B)=Sof(C49B)=Sof(H49B)=
 Sof(C45B)=Sof(C53B)=Sof(H53D)=Sof(H53E)=Sof(H53F)=Sof(C52B)=Sof(H52D)=
 Sof(H52E)=Sof(H52F)=Sof(N3B)=Sof(O10B)=Sof(C44B)=Sof(C47B)=Sof(C54B)=Sof(H54D)=
 Sof(H54E)=Sof(H54F)=Sof(C55B)=Sof(H55D)=Sof(H55E)=Sof(H55F)=1-FVAR(1)
 Sof(C51A)=Sof(H51A)=Sof(C46A)=Sof(N3A)=Sof(C49A)=Sof(H49A)=Sof(C54A)=
 Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(O10A)=Sof(C55A)=Sof(H55A)=Sof(H55B)=
 Sof(H55C)=Sof(C47A)=Sof(C45A)=Sof(C48A)=Sof(H48A)=Sof(C52A)=Sof(H52A)=
 Sof(H52B)=Sof(H52C)=Sof(C44A)=Sof(C53A)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(1)
 Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=1-FVAR(2)
 Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C20A)=Sof(H20A)=Sof(H20B)=
 Sof(H20C)=FVAR(2)
 Fixed Sof: C66A(0.5) H66A(0.5) H66B(0.5) H66C(0.5) C67A(0.5) H67A(0.5)
 H67B(0.5) H67C(0.5) C66B(0.5) H66D(0.5) H66E(0.5) H66F(0.5) C67B(0.5)
 H67D(0.5) H67E(0.5) H67F(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C60(H60), C26(H26), C27(H27), C16(H16), C51A(H51A), C62(H62),
 C6(H6), C14(H14), C7(H7), C8(H8), C17(H17), C49A(H49A), C41(H41), C42(H42),
 C40(H40), C63(H63), C48A(H48A), C48B(H48B), C51B(H51B), C49B(H49B)
4.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C19(H19A,H19B,H19C), C33(H33A,H33B,H33C), C64(H64A,H64B,
 H64C), C54A(H54A,H54B,H54C), C30(H30A,H30B,H30C), C21A(H21A,H21B,H21C),
 C18(H18A,H18B,H18C), C65(H65A,H65B,H65C), C55A(H55A,H55B,H55C), C31(H31A,H31B,
 H31C), C52A(H52A,H52B,H52C), C20A(H20A,H20B,H20C), C66A(H66A,H66B,H66C),
 C67A(H67A,H67B,H67C), C53A(H53A,H53B,H53C), C66B(H66D,H66E,H66F), C67B(H67D,
 H67E,H67F), C53B(H53D,H53E,H53F), C52B(H52D,H52E,H52F), C54B(H54D,H54E,H54F),
 C55B(H55D,H55E,H55F), C20B(H20D,H20E,H20F), C21B(H21D,H21E,H21F)
4.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O9(H9)
;
_shelx_res_checksum              88104
_shelx_hkl_checksum              78268
_olex2_submission_original_sample_id 1b
_olex2_submission_special_instructions 'No special instructions were received'