#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:39:27 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159123.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_7159123
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  86.00   0.50    1.00    --    8.04  37.00  90.00  192
  2  ω     -2.00  81.00   0.50    1.00    --    8.04  57.00 120.00  166
  3  ω    -10.00  69.00   0.50    1.00    --    8.04  57.00   0.00  158
  4  ω     41.00  82.00   0.50    1.00    --    8.04  57.00-180.00   82
  5  ω     -8.00  31.00   0.50    1.00    --    8.04  57.00-180.00   78
  6  ω    -69.00  25.00   0.50    1.00    --    8.04 -37.00-150.00  188
  7  ω     25.00  50.00   0.50    1.00    --   -9.76  57.00  30.00   50
  8  ω    -29.00   1.00   0.50    1.00    --   -9.76  57.00  30.00   60
  9  ω    -20.00   7.00   0.50    1.00    --   -9.76 -57.00 150.00   54
 10  ω    -51.00 -26.00   0.50    1.00    --   -9.76 -57.00 150.00   50
 11  ω    -80.00 -34.00   0.50    1.00    --   -9.76 -37.00 120.00   92
 12  ω    -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       'ω 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/[σ²(Fo²)+(0.0634P)²+0.1176P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_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.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.45948(14) 0.24791(7) 0.60604(6) 0.02355(18) Uani 1 1 d . . . . .
O4 O -0.04560(14) 0.37275(7) 0.15026(6) 0.02445(19) Uani 1 1 d . . . . .
O3 O 0.97788(17) 0.15420(9) 0.84610(7) 0.0343(2) Uani 1 1 d . . . . .
H3 H 1.042958 0.120906 0.795575 0.051 Uiso 1 1 calc R U . . .
O2 O 1.03281(17) 0.07769(9) 0.66001(7) 0.0361(2) Uani 1 1 d . . . . .
N1 N 0.14492(15) 0.33911(8) 0.20425(6) 0.01855(19) Uani 1 1 d . . . . .
C12 C 0.25227(18) 0.28006(9) 0.33624(8) 0.0184(2) Uani 1 1 d . . . . .
C13 C 0.11158(18) 0.37356(9) 0.31099(8) 0.0190(2) Uani 1 1 d . . . . .
C17 C 0.33874(19) 0.27931(10) 0.42850(8) 0.0204(2) Uani 1 1 d . . . . .
H17 H 0.307610 0.341864 0.486706 0.024 Uiso 1 1 calc R U . . .
C14 C 0.42294(19) 0.09212(10) 0.25629(8) 0.0207(2) Uani 1 1 d . . . . .
H14 H 0.448810 0.028311 0.197902 0.025 Uiso 1 1 calc R U . . .
C11 C 0.29268(18) 0.18677(9) 0.25059(8) 0.0179(2) Uani 1 1 d . . . . .
C10 C 0.17757(18) 0.20687(9) 0.16000(8) 0.0182(2) Uani 1 1 d . . . . .
C9 C 0.5335(2) 0.25606(10) 0.70135(8) 0.0230(2) Uani 1 1 d . . . . .
C15 C 0.51501(19) 0.09173(10) 0.34830(8) 0.0217(2) Uani 1 1 d . . . . .
H15 H 0.606943 0.028128 0.352764 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5776(2) 0.18341(10) 0.53129(8) 0.0218(2) Uani 1 1 d . . . . .
C16 C 0.47317(19) 0.18460(10) 0.43463(8) 0.0207(2) Uani 1 1 d . . . . .
C4 C 0.7286(2) 0.19901(10) 0.72254(8) 0.0227(2) Uani 1 1 d . . . . .
C19 C -0.04548(19) 0.12516(10) 0.11875(8) 0.0238(2) Uani 1 1 d . . . . .
H19A H -0.148045 0.140229 0.170309 0.036 Uiso 1 1 calc R U . . .
H19B H -0.007822 0.040277 0.097112 0.036 Uiso 1 1 calc R U . . .
H19C H -0.122934 0.142837 0.062487 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8576(2) 0.13015(11) 0.64357(9) 0.0257(2) Uani 1 1 d . . . . .
C5 C 0.7918(2) 0.20805(11) 0.82184(9) 0.0256(2) Uani 1 1 d . . . . .
C2 C 0.7688(2) 0.12662(11) 0.54629(9) 0.0263(2) Uani 1 1 d . . . . .
H2 H 0.846058 0.083583 0.491579 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3342(2) 0.18774(11) 0.07890(8) 0.0247(2) Uani 1 1 d . . . . .
H18A H 0.252760 0.206081 0.023710 0.037 Uiso 1 1 calc R U . . .
H18B H 0.375695 0.103476 0.055722 0.037 Uiso 1 1 calc R U . . .
H18C H 0.474715 0.241374 0.105231 0.037 Uiso 1 1 calc R U . . .
C20 C 0.2169(2) 0.50248(10) 0.36497(9) 0.0268(3) Uani 1 1 d . . . . .
H20A H 0.375326 0.508377 0.349671 0.040 Uiso 1 1 calc R U . . .
H20B H 0.218382 0.522652 0.436336 0.040 Uiso 1 1 calc R U . . .
H20C H 0.124463 0.559030 0.343488 0.040 Uiso 1 1 calc R U . . .
C6 C 0.6601(2) 0.27108(12) 0.89450(9) 0.0310(3) Uani 1 1 d . . . . .
H6 H 0.700096 0.275818 0.960869 0.037 Uiso 1 1 calc R U . . .
C21 C -0.1397(2) 0.36497(11) 0.33153(9) 0.0265(2) Uani 1 1 d . . . . .
H21A H -0.230993 0.417620 0.304804 0.040 Uiso 1 1 calc R U . . .
H21B H -0.144758 0.390540 0.402950 0.040 Uiso 1 1 calc R U . . .
H21C H -0.203834 0.281254 0.299939 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4034(2) 0.32159(13) 0.77342(9) 0.0318(3) Uani 1 1 d . . . . .
H8 H 0.273493 0.361397 0.757698 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4695(2) 0.32716(13) 0.86977(10) 0.0355(3) Uani 1 1 d . . . . .
H7 H 0.381191 0.370822 0.920249 0.043 Uiso 1 1 calc R U . . .
C22 C 0.0418(3) 0.45860(12) 0.11168(10) 0.0358(3) Uani 1 1 d . . . . .
H22A H 0.155147 0.421588 0.066953 0.054 Uiso 1 1 calc R U . . .
H22B H 0.116086 0.528976 0.166133 0.054 Uiso 1 1 calc R U . . .
H22C H -0.085578 0.484243 0.075408 0.054 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 119.65(9) . . ?
C22 O4 N1 107.83(9) . . ?
C5 O3 H3 109.5 . . ?
O4 N1 C13 110.75(8) . . ?
O4 N1 C10 110.94(8) . . ?
C10 N1 C13 110.86(8) . . ?
C17 C12 C13 128.55(10) . . ?
C17 C12 C11 120.73(10) . . ?
C11 C12 C13 110.71(9) . . ?
N1 C13 C12 99.11(8) . . ?
N1 C13 C20 107.99(8) . . ?
N1 C13 C21 115.29(9) . . ?
C12 C13 C20 112.62(9) . . ?
C12 C13 C21 111.79(9) . . ?
C20 C13 C21 109.71(9) . . ?
C12 C17 H17 120.5 . . ?
C12 C17 C16 118.93(10) . . ?
C16 C17 H17 120.5 . . ?
C11 C14 H14 120.4 . . ?
C11 C14 C15 119.27(10) . . ?
C15 C14 H14 120.4 . . ?
C12 C11 C10 110.72(9) . . ?
C14 C11 C12 120.55(10) . . ?
C14 C11 C10 128.73(10) . . ?
N1 C10 C11 99.06(8) . . ?
N1 C10 C19 115.41(9) . . ?
N1 C10 C18 108.43(9) . . ?
C11 C10 C19 110.50(9) . . ?
C11 C10 C18 113.35(9) . . ?
C18 C10 C19 109.82(9) . . ?
O1 C9 C4 120.93(10) . . ?
O1 C9 C8 116.55(11) . . ?
C8 C9 C4 122.52(10) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.43(10) . . ?
C16 C15 H15 119.8 . . ?
O1 C1 C16 112.03(10) . . ?
C2 C1 O1 122.73(10) . . ?
C2 C1 C16 125.23(11) . . ?
C17 C16 C1 120.63(10) . . ?
C15 C16 C17 120.06(10) . . ?
C15 C16 C1 119.28(10) . . ?
C9 C4 C3 120.15(10) . . ?
C9 C4 C5 118.12(11) . . ?
C5 C4 C3 121.71(11) . . ?
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 . . ?
O2 C3 C4 121.76(11) . . ?
O2 C3 C2 122.95(12) . . ?
C2 C3 C4 115.29(11) . . ?
O3 C5 C4 120.44(11) . . ?
O3 C5 C6 119.52(11) . . ?
C6 C5 C4 120.03(12) . . ?
C1 C2 C3 121.25(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
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 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.58(11) . . ?
C7 C6 H6 120.2 . . ?
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 . . ?
C9 C8 H8 121.2 . . ?
C9 C8 C7 117.60(12) . . ?
C7 C8 H8 121.2 . . ?
C6 C7 C8 122.13(13) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C9 1.3761(13) . ?
O1 C1 1.3600(14) . ?
O4 N1 1.4356(11) . ?
O4 C22 1.4254(15) . ?
O3 H3 0.8400 . ?
O3 C5 1.3473(15) . ?
O2 C3 1.2522(15) . ?
N1 C13 1.4977(14) . ?
N1 C10 1.4957(14) . ?
C12 C13 1.5128(15) . ?
C12 C17 1.3847(15) . ?
C12 C11 1.3958(15) . ?
C13 C20 1.5294(15) . ?
C13 C21 1.5352(15) . ?
C17 H17 0.9500 . ?
C17 C16 1.4043(16) . ?
C14 H14 0.9500 . ?
C14 C11 1.3881(16) . ?
C14 C15 1.3888(15) . ?
C11 C10 1.5089(14) . ?
C10 C19 1.5356(14) . ?
C10 C18 1.5272(15) . ?
C9 C4 1.3968(16) . ?
C9 C8 1.3826(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.4021(16) . ?
C1 C16 1.4756(15) . ?
C1 C2 1.3523(16) . ?
C4 C3 1.4545(17) . ?
C4 C5 1.4175(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C3 C2 1.4394(16) . ?
C5 C6 1.3852(19) . ?
C2 H2 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 . ?
C6 H6 0.9500 . ?
C6 C7 1.3855(19) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.3911(17) . ?
C7 H7 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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 C9 C4 C3 0.27(16) . . . . ?
O1 C9 C4 C5 -178.22(9) . . . . ?
O1 C9 C8 C7 177.54(11) . . . . ?
O1 C1 C16 C17 24.80(14) . . . . ?
O1 C1 C16 C15 -157.04(10) . . . . ?
O1 C1 C2 C3 0.80(18) . . . . ?
O4 N1 C13 C12 153.42(8) . . . . ?
O4 N1 C13 C20 -89.09(10) . . . . ?
O4 N1 C13 C21 33.98(12) . . . . ?
O4 N1 C10 C11 -154.19(8) . . . . ?
O4 N1 C10 C19 -36.27(12) . . . . ?
O4 N1 C10 C18 87.37(10) . . . . ?
O3 C5 C6 C7 179.58(11) . . . . ?
O2 C3 C2 C1 179.30(12) . . . . ?
C12 C17 C16 C15 -1.01(16) . . . . ?
C12 C17 C16 C1 177.13(9) . . . . ?
C12 C11 C10 N1 19.02(10) . . . . ?
C12 C11 C10 C19 -102.54(10) . . . . ?
C12 C11 C10 C18 133.70(10) . . . . ?
C13 N1 C10 C11 -30.69(10) . . . . ?
C13 N1 C10 C19 87.23(11) . . . . ?
C13 N1 C10 C18 -149.13(8) . . . . ?
C13 C12 C17 C16 -177.73(10) . . . . ?
C13 C12 C11 C14 178.66(9) . . . . ?
C13 C12 C11 C10 -1.60(12) . . . . ?
C17 C12 C13 N1 162.83(10) . . . . ?
C17 C12 C13 C20 48.90(15) . . . . ?
C17 C12 C13 C21 -75.16(13) . . . . ?
C17 C12 C11 C14 -0.80(15) . . . . ?
C17 C12 C11 C10 178.94(9) . . . . ?
C14 C11 C10 N1 -161.26(10) . . . . ?
C14 C11 C10 C19 77.18(13) . . . . ?
C14 C11 C10 C18 -46.58(14) . . . . ?
C14 C15 C16 C17 -0.44(16) . . . . ?
C14 C15 C16 C1 -178.60(10) . . . . ?
C11 C12 C13 N1 -16.58(10) . . . . ?
C11 C12 C13 C20 -130.51(10) . . . . ?
C11 C12 C13 C21 105.43(10) . . . . ?
C11 C12 C17 C16 1.62(15) . . . . ?
C11 C14 C15 C16 1.27(16) . . . . ?
C10 N1 C13 C12 29.82(10) . . . . ?
C10 N1 C13 C20 147.31(9) . . . . ?
C10 N1 C13 C21 -89.62(11) . . . . ?
C9 O1 C1 C16 179.91(8) . . . . ?
C9 O1 C1 C2 -0.58(16) . . . . ?
C9 C4 C3 O2 -179.82(11) . . . . ?
C9 C4 C3 C2 -0.07(16) . . . . ?
C9 C4 C5 O3 179.70(10) . . . . ?
C9 C4 C5 C6 0.64(16) . . . . ?
C9 C8 C7 C6 0.8(2) . . . . ?
C15 C14 C11 C12 -0.66(15) . . . . ?
C15 C14 C11 C10 179.65(10) . . . . ?
C1 O1 C9 C4 0.03(15) . . . . ?
C1 O1 C9 C8 -179.10(10) . . . . ?
C16 C1 C2 C3 -179.76(10) . . . . ?
C4 C9 C8 C7 -1.58(19) . . . . ?
C4 C3 C2 C1 -0.45(17) . . . . ?
C4 C5 C6 C7 -1.35(18) . . . . ?
C3 C4 C5 O3 1.23(16) . . . . ?
C3 C4 C5 C6 -177.83(11) . . . . ?
C5 C4 C3 O2 -1.38(18) . . . . ?
C5 C4 C3 C2 178.37(10) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C2 C1 C16 C17 -154.70(11) . . . . ?
C2 C1 C16 C15 23.46(16) . . . . ?
C8 C9 C4 C3 179.35(11) . . . . ?
C8 C9 C4 C5 0.86(17) . . . . ?
C22 O4 N1 C13 117.79(9) . . . . ?
C22 O4 N1 C10 -118.65(10) . . . . ?
