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_7159124
_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         'C36 H39.75 N2 O6.25'
_chemical_formula_sum            'C36 H39.75 N2 O6.25'
_chemical_formula_weight         600.45
_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
_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                90
_cell_angle_beta                 94.83(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.664(2)
_cell_length_b                   34.087(7)
_cell_length_c                   8.8880(18)
_cell_measurement_reflns_used    1242
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.281
_cell_measurement_theta_min      25.000
_cell_volume                     3219.3(11)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            50607
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.917
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_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    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1279
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         7954
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0922P)^2^+1.9456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7441
_reflns_number_total             7954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02101c2.cif
_cod_data_source_block           20
_cod_depositor_comments
'Adding full bibliography for 7159122--7159125.cif.'
_cod_original_cell_volume        3219.4(11)
_cod_database_code               7159124
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{C8A, C8}
3. Restrained distances
 N1-O4A \\sim N1-O4B
 with sigma of 0.02
 O4A-C35A \\sim O4A-C35B
 with sigma of 0.02
 O4A-C35A \\sim O4B-C35A
 with sigma of 0.02
 C35A-O4B \\sim C35B-O4B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C8)
5. Others
 Sof(O4B)=1-FVAR(1)
 Sof(O4A)=FVAR(1)
 Sof(C35B)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(2)
 Sof(C35A)=Sof(H35C)=Sof(H35A)=Sof(H35B)=FVAR(2)
 Fixed Sof: C8(0.25) H7A(0.75) H7B(0.25) O4(0.25) C8A(0.75) H8A(0.75)
6.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C28(H28), C29(H29), C15(H15), C17(H17), C14(H14), C7(H7A), C7(H7B),
 C6(H6), C8A(H8A)
6.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C33(H33A,H33B,
 H33C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B,H36C), C20(H20B,
 H20C,H20A), C21(H21A,H21B,H21C), C35A(H35C,H35A,H35B), C35B(H35D,H35E,H35F)
6.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              57742
_shelx_hkl_checksum              37712
_olex2_submission_original_sample_id 5b
_olex2_submission_special_instructions 'No special instructions were received'