#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:39:27 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159122.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159122
loop_
_publ_author_name
'Larin, Astrid C. R.'
'Pfrunder, Michael C.'
'Mullen, Kathleen M.'
'Wiedbrauk, Sandra'
'Boase, Nathan R.'
'Fairfull-Smith, Kathryn E'
_publ_section_title
;
 Synergistic or antagonistic antioxidant combinations - a case study
 exploring flavonoid-nitroxide hybrids.
;
_journal_issue                   8
_journal_name_full               'Organic & 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         'C21 H20 N O4'
_chemical_formula_sum            'C21 H20 N O4'
_chemical_formula_weight         350.38
_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                 104.29(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8730(14)
_cell_length_b                   20.799(4)
_cell_length_c                   12.761(3)
_cell_measurement_reflns_used    561
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.208
_cell_measurement_theta_min      25.244
_cell_volume                     1767.8(7)
_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 0.991
_diffrn_measured_fraction_theta_max 0.837
_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     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31161
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.244
_diffrn_reflns_theta_max         32.208
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_exptl_absorpt_coefficient_mu    0.091
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         5232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0649
_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/[σ²(Fo²)+(0.1216P)²+0.2334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4565
_reflns_number_total             5232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02101c2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7159122--7159125.cif.'
_cod_database_code               7159122
_shelx_shelxl_version_number     2019/2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.991
_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:
 C14(H14), C2(H2), C17(H17), C16(H16), C8(H8), C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_original_sample_id 5a
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24953(15) 0.47596(4) 0.41462(7) 0.0416(2) Uani 1 1 d . . . . .
O3 O 0.22592(17) 0.48356(5) 0.78735(7) 0.0494(3) Uani 1 1 d . . . . .
H3 H 0.238743 0.522936 0.776018 0.074 Uiso 1 1 calc R U . . .
O2 O 0.27300(18) 0.58617(5) 0.68181(7) 0.0508(3) Uani 1 1 d . . . . .
O4 O 0.2726(2) 0.75158(5) -0.04387(8) 0.0634(3) Uani 1 1 d . . . . .
N1 N 0.2750(2) 0.70561(5) 0.02267(8) 0.0511(3) Uani 1 1 d . . . . .
C15 C 0.2722(2) 0.56322(6) 0.30150(9) 0.0395(3) Uani 1 1 d . . . . .
C1 C 0.26656(19) 0.54105(6) 0.41025(9) 0.0391(3) Uani 1 1 d . . . . .
C14 C 0.2787(2) 0.62909(6) 0.28059(9) 0.0409(3) Uani 1 1 d . . . . .
H14 H 0.283444 0.659624 0.336529 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2641(2) 0.55230(6) 0.59972(9) 0.0419(3) Uani 1 1 d . . . . .
C2 C 0.2754(2) 0.57905(6) 0.49752(9) 0.0416(3) Uani 1 1 d . . . . .
H2 H 0.289443 0.624215 0.491068 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2366(2) 0.44680(6) 0.50924(9) 0.0411(3) Uani 1 1 d . . . . .
C17 C 0.2651(2) 0.53938(6) 0.11445(9) 0.0441(3) Uani 1 1 d . . . . .
H17 H 0.260661 0.509155 0.058089 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2795(2) 0.71726(6) 0.13809(9) 0.0451(3) Uani 1 1 d . . . . .
C16 C 0.2661(2) 0.51872(6) 0.21834(9) 0.0423(3) Uani 1 1 d . . . . .
H16 H 0.262633 0.474014 0.232996 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2782(2) 0.64908(6) 0.17683(9) 0.0414(3) Uani 1 1 d . . . . .
C13 C 0.2694(2) 0.63727(6) -0.01088(9) 0.0464(3) Uani 1 1 d . . . . .
C5 C 0.2235(2) 0.45027(6) 0.69665(10) 0.0437(3) Uani 1 1 d . . . . .
C4 C 0.2406(2) 0.48305(6) 0.60204(9) 0.0405(3) Uani 1 1 d . . . . .
C8 C 0.2192(2) 0.38058(6) 0.50721(10) 0.0452(3) Uani 1 1 d . . . . .
H8 H 0.220392 0.356730 0.443887 0.054 Uiso 1 1 calc R U . . .
C21 C 0.4562(3) 0.62121(7) -0.05098(11) 0.0530(3) Uani 1 1 d . . . . .
H21A H 0.454279 0.646107 -0.116431 0.080 Uiso 1 1 calc R U . . .
H21B H 0.456906 0.575197 -0.067422 0.080 Uiso 1 1 calc R U . . .
H21C H 0.576941 0.632047 0.005244 0.080 Uiso 1 1 calc R U . . .
C19 C 0.4673(3) 0.75476(6) 0.19277(11) 0.0527(3) Uani 1 1 d . . . . .
H19A H 0.586046 0.732610 0.181117 0.079 Uiso 1 1 calc R U . . .
H19B H 0.476790 0.757730 0.270515 0.079 Uiso 1 1 calc R U . . .
H19C H 0.459985 0.798095 0.161877 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2707(2) 0.60473(6) 0.09466(9) 0.0424(3) Uani 1 1 d . . . . .
C7 C 0.1997(2) 0.35004(7) 0.60118(11) 0.0482(3) Uani 1 1 d . . . . .
H7 H 0.185097 0.304617 0.601156 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2012(2) 0.38418(6) 0.69512(10) 0.0464(3) Uani 1 1 d . . . . .
H6 H 0.186903 0.362163 0.758010 0.056 Uiso 1 1 calc R U . . .
C18 C 0.0910(3) 0.75384(7) 0.14642(12) 0.0538(4) Uani 1 1 d . . . . .
H18A H 0.093306 0.797074 0.116220 0.081 Uiso 1 1 calc R U . . .
H18B H 0.087241 0.757087 0.222509 0.081 Uiso 1 1 calc R U . . .
H18C H -0.028336 0.730817 0.105882 0.081 Uiso 1 1 calc R U . . .
C20 C 0.0766(3) 0.62389(7) -0.09777(10) 0.0537(4) Uani 1 1 d . . . . .
H20A H -0.039516 0.637612 -0.071675 0.081 Uiso 1 1 calc R U . . .
H20B H 0.066439 0.577749 -0.113707 0.081 Uiso 1 1 calc R U . . .
H20C H 0.079299 0.647748 -0.163627 0.081 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 120.00(9) . . ?
C5 O3 H3 109.5 . . ?
O4 N1 C10 122.08(10) . . ?
O4 N1 C13 122.09(10) . . ?
C13 N1 C10 115.82(9) . . ?
C14 C15 C1 119.75(10) . . ?
C14 C15 C16 119.93(10) . . ?
C16 C15 C1 120.30(10) . . ?
O1 C1 C15 111.88(9) . . ?
C2 C1 O1 122.24(10) . . ?
C2 C1 C15 125.88(11) . . ?
C15 C14 H14 120.6 . . ?
C11 C14 C15 118.89(10) . . ?
C11 C14 H14 120.6 . . ?
O2 C3 C2 122.64(12) . . ?
O2 C3 C4 121.64(11) . . ?
C2 C3 C4 115.72(10) . . ?
C1 C2 C3 121.24(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
O1 C9 C4 120.95(11) . . ?
O1 C9 C8 116.59(11) . . ?
C8 C9 C4 122.46(11) . . ?
C16 C17 H17 120.6 . . ?
C12 C17 H17 120.6 . . ?
C12 C17 C16 118.87(11) . . ?
N1 C10 C11 99.90(9) . . ?
N1 C10 C19 110.22(12) . . ?
N1 C10 C18 109.87(12) . . ?
C11 C10 C19 113.94(11) . . ?
C11 C10 C18 111.91(11) . . ?
C19 C10 C18 110.51(11) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.65(11) . . ?
C17 C16 H16 119.7 . . ?
C14 C11 C10 126.74(10) . . ?
C14 C11 C12 120.85(11) . . ?
C12 C11 C10 112.38(10) . . ?
N1 C13 C21 109.97(12) . . ?
N1 C13 C12 100.30(9) . . ?
N1 C13 C20 109.88(12) . . ?
C12 C13 C21 112.35(12) . . ?
C12 C13 C20 112.32(12) . . ?
C20 C13 C21 111.46(11) . . ?
O3 C5 C4 119.96(12) . . ?
O3 C5 C6 120.11(11) . . ?
C6 C5 C4 119.92(11) . . ?
C9 C4 C3 119.82(10) . . ?
C9 C4 C5 118.28(12) . . ?
C5 C4 C3 121.90(11) . . ?
C9 C8 H8 121.2 . . ?
C9 C8 C7 117.70(12) . . ?
C7 C8 H8 121.2 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C12 C11 120.80(10) . . ?
C17 C12 C13 127.61(10) . . ?
C11 C12 C13 111.59(10) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.83(12) . . ?
C6 C7 H7 119.1 . . ?
C5 C6 C7 119.79(11) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3611(14) . ?
O1 C9 1.3736(13) . ?
O3 H3 0.8400 . ?
O3 C5 1.3454(15) . ?
O2 C3 1.2512(14) . ?
O4 N1 1.2761(13) . ?
N1 C10 1.4856(15) . ?
N1 C13 1.4821(16) . ?
C15 C1 1.4719(15) . ?
C15 C14 1.3986(16) . ?
C15 C16 1.4008(15) . ?
C1 C2 1.3547(15) . ?
C14 H14 0.9500 . ?
C14 C11 1.3871(14) . ?
C3 C2 1.4375(15) . ?
C3 C4 1.4505(18) . ?
C2 H2 0.9500 . ?
C9 C4 1.3984(16) . ?
C9 C8 1.3823(17) . ?
C17 H17 0.9500 . ?
C17 C16 1.3920(15) . ?
C17 C12 1.3848(17) . ?
C10 C11 1.5024(16) . ?
C10 C19 1.522(2) . ?
C10 C18 1.528(2) . ?
C16 H16 0.9500 . ?
C11 C12 1.3881(15) . ?
C13 C21 1.532(2) . ?
C13 C12 1.5053(15) . ?
C13 C20 1.529(2) . ?
C5 C4 1.4165(15) . ?
C5 C6 1.3826(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.3922(16) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.3912(18) . ?
C6 H6 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -1.0(2) . . . . ?
O1 C9 C4 C3 -1.65(19) . . . . ?
O1 C9 C4 C5 179.01(12) . . . . ?
O1 C9 C8 C7 -178.11(12) . . . . ?
O3 C5 C4 C3 1.0(2) . . . . ?
O3 C5 C4 C9 -179.72(12) . . . . ?
O3 C5 C6 C7 -179.71(13) . . . . ?
O2 C3 C2 C1 179.60(13) . . . . ?
O2 C3 C4 C9 -178.33(13) . . . . ?
O2 C3 C4 C5 1.0(2) . . . . ?
O4 N1 C10 C11 179.34(14) . . . . ?
O4 N1 C10 C19 -60.44(18) . . . . ?
O4 N1 C10 C18 61.57(19) . . . . ?
O4 N1 C13 C21 62.65(19) . . . . ?
O4 N1 C13 C12 -178.85(15) . . . . ?
O4 N1 C13 C20 -60.40(18) . . . . ?
N1 C10 C11 C14 -179.20(14) . . . . ?
N1 C10 C11 C12 -0.87(16) . . . . ?
N1 C13 C12 C17 179.31(15) . . . . ?
N1 C13 C12 C11 -0.54(16) . . . . ?
C15 C1 C2 C3 178.56(13) . . . . ?
C15 C14 C11 C10 178.38(13) . . . . ?
C15 C14 C11 C12 0.2(2) . . . . ?
C1 O1 C9 C4 0.00(18) . . . . ?
C1 O1 C9 C8 179.85(12) . . . . ?
C1 C15 C14 C11 -178.19(12) . . . . ?
C1 C15 C16 C17 178.01(12) . . . . ?
C14 C15 C1 O1 176.66(12) . . . . ?
C14 C15 C1 C2 -2.9(2) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C14 C11 C12 C17 -0.5(2) . . . . ?
C14 C11 C12 C13 179.39(13) . . . . ?
C2 C3 C4 C9 1.91(19) . . . . ?
C2 C3 C4 C5 -178.78(12) . . . . ?
C9 O1 C1 C15 -178.26(11) . . . . ?
C9 O1 C1 C2 1.35(19) . . . . ?
C9 C8 C7 C6 -1.1(2) . . . . ?
C10 N1 C13 C21 -118.55(13) . . . . ?
C10 N1 C13 C12 -0.04(16) . . . . ?
C10 N1 C13 C20 118.40(13) . . . . ?
C10 C11 C12 C17 -178.91(13) . . . . ?
C10 C11 C12 C13 0.95(17) . . . . ?
C16 C15 C1 O1 -1.80(18) . . . . ?
C16 C15 C1 C2 178.62(13) . . . . ?
C16 C15 C14 C11 0.3(2) . . . . ?
C16 C17 C12 C11 0.3(2) . . . . ?
C16 C17 C12 C13 -179.54(14) . . . . ?
C13 N1 C10 C11 0.53(17) . . . . ?
C13 N1 C10 C19 120.75(13) . . . . ?
C13 N1 C10 C18 -117.23(13) . . . . ?
C4 C3 C2 C1 -0.6(2) . . . . ?
C4 C9 C8 C7 1.7(2) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C8 C9 C4 C3 178.51(13) . . . . ?
C8 C9 C4 C5 -0.8(2) . . . . ?
C8 C7 C6 C5 -0.4(2) . . . . ?
C21 C13 C12 C17 -63.95(19) . . . . ?
C21 C13 C12 C11 116.20(14) . . . . ?
C19 C10 C11 C14 63.32(19) . . . . ?
C19 C10 C11 C12 -118.35(13) . . . . ?
C12 C17 C16 C15 0.2(2) . . . . ?
C6 C5 C4 C3 179.95(13) . . . . ?
C6 C5 C4 C9 -0.7(2) . . . . ?
C18 C10 C11 C14 -62.97(18) . . . . ?
C18 C10 C11 C12 115.36(13) . . . . ?
C20 C13 C12 C17 62.68(19) . . . . ?
C20 C13 C12 C11 -117.17(13) . . . . ?
