#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:23:33 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160265.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_7160265
loop_
_publ_author_name
'Hopkins, Scarlet L.'
'Clarke, Kristen T.'
'Clegg, Jack K.'
'Gee, William J.'
_publ_section_title
;
 One-pot synthesis of azepine spiro[4.6]-γ-lactams by a
 Hantzsch-type reaction.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              614
_journal_page_last               618
_journal_paper_doi               10.1039/d4ob01719f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H15 N O5'
_chemical_formula_sum            'C26 H15 N O5'
_chemical_formula_weight         421.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.173(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.885(2)
_cell_length_b                   9.4476(11)
_cell_length_c                   15.911(2)
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      24.8650
_cell_measurement_theta_min      2.9110
_cell_volume                     2008.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0217
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  35.00   1.00    5.00    --   19.52 -57.00-150.00   65
  2  ω     17.00  46.00   1.00    5.00    --   19.52 -77.00 120.00   29
  3  ω     12.00  38.00   1.00    5.00    --   19.52  77.00-180.00   26
  4  ω    -84.00  -4.00   1.00    5.00    --  -20.93 -57.00 -60.00   80
  5  ω    -32.00  31.00   1.00    5.00    --  -20.93  57.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0117680000
_diffrn_orient_matrix_UB_12      0.0366033000
_diffrn_orient_matrix_UB_13      0.0328649000
_diffrn_orient_matrix_UB_21      0.0442077000
_diffrn_orient_matrix_UB_22      0.0409811000
_diffrn_orient_matrix_UB_23      0.0139388000
_diffrn_orient_matrix_UB_31      -0.0269552000
_diffrn_orient_matrix_UB_32      0.0511567000
_diffrn_orient_matrix_UB_33      -0.0344817000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.121
_diffrn_reflns_theta_max         25.121
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0635
_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)+(0.0562P)²+0.6480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2538
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           gwg23jc01_auto
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_original_cell_volume        2008.0(6)
_cod_database_code               7160265
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H15 N O5'
_chemical_oxdiff_usercomment     'oidb - dark crystal'
_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   0.995
_shelx_estimated_absorpt_t_min   0.953
_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, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C17 \\sim C12 \\sim C11 \\sim C14 \\sim C15 \\sim C16: within 2A with sigma of
0.02 and sigma for terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C18(H18), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C4(H4), C7(H7), C23(H23), C26(H26), C24(H24),
 C25(H25), C14(H14), C15(H15), C17(H17), C16(H16)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.799
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.74056(16) 0.5231(2) 0.26963(13) 0.0410(6) Uani 1 1 d . . . . .
N1 N 0.70545(17) 0.2973(2) 0.29932(14) 0.0298(6) Uani 1 1 d . . . . .
H1 H 0.730205 0.249988 0.266653 0.036 Uiso 1 1 calc R U . . .
O3 O 0.57528(17) 0.6946(2) 0.46555(13) 0.0438(6) Uani 1 1 d . . . . .
O5 O 0.62381(18) 0.7851(2) 0.28440(14) 0.0484(6) Uani 1 1 d . . . . .
O2 O 0.85814(16) 0.4296(2) 0.50244(14) 0.0475(6) Uani 1 1 d . . . . .
O4 O 0.44406(17) 0.3531(2) 0.21067(14) 0.0492(6) Uani 1 1 d . . . . .
C1 C 0.7054(2) 0.4391(3) 0.30493(17) 0.0295(7) Uani 1 1 d . . . . .
C8 C 0.6614(2) 0.2333(3) 0.35158(17) 0.0269(6) Uani 1 1 d . . . . .
C3 C 0.6253(2) 0.3372(3) 0.39029(17) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.5750(2) 0.1584(3) 0.46486(19) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.545725 0.130889 0.504677 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6104(2) 0.0558(3) 0.4249(2) 0.0391(8) Uani 1 1 d . . . . .
H6 H 0.605646 -0.041199 0.438175 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5818(2) 0.2998(3) 0.44753(18) 0.0311(7) Uani 1 1 d . . . . .
H4 H 0.556901 0.370050 0.474512 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5688(2) 0.6875(3) 0.24422(19) 0.0333(7) Uani 1 1 d . . . . .
C7 C 0.6528(2) 0.0923(3) 0.36574(19) 0.0331(7) Uani 1 1 d . . . . .
H7 H 0.674909 0.022207 0.336305 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5489(2) 0.5564(3) 0.29006(17) 0.0280(6) Uani 1 1 d . . . . .
H18 H 0.511358 0.587701 0.325719 0.034 Uiso 1 1 calc R U . . .
C21 C 0.5091(2) 0.6759(3) 0.14204(18) 0.0318(7) Uani 1 1 d . . . . .
C2 C 0.6453(2) 0.4801(3) 0.35957(16) 0.0253(6) Uani 1 1 d . . . . .
C10 C 0.8009(2) 0.5035(3) 0.51734(18) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.7086(2) 0.5765(3) 0.44268(17) 0.0290(7) Uani 1 1 d . . . . .
H9 H 0.732427 0.657864 0.417596 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6563(2) 0.6371(3) 0.49784(18) 0.0302(7) Uani 1 1 d . . . . .
C20 C 0.4548(2) 0.5498(3) 0.12062(18) 0.0321(7) Uani 1 1 d . . . . .
C19 C 0.4774(2) 0.4678(3) 0.20658(18) 0.0313(7) Uani 1 1 d . . . . .
C11 C 0.8056(2) 0.5399(4) 0.60910(18) 0.0414(8) Uani 1 1 d . U . . .
C23 C 0.3912(2) 0.5150(4) 0.02914(19) 0.0411(8) Uani 1 1 d . . . . .
H23 H 0.353573 0.429714 0.014101 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5039(2) 0.7692(3) 0.0733(2) 0.0404(8) Uani 1 1 d . . . . .
H26 H 0.541654 0.854384 0.088059 0.049 Uiso 1 1 calc R U . . .
C24 C 0.3846(2) 0.6104(4) -0.0402(2) 0.0439(9) Uani 1 1 d . . . . .
H24 H 0.340545 0.590489 -0.103694 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7222(2) 0.6168(4) 0.59727(19) 0.0406(8) Uani 1 1 d . U . . .
C25 C 0.4403(2) 0.7323(4) -0.0187(2) 0.0467(9) Uani 1 1 d . . . . .
H25 H 0.435445 0.793208 -0.068044 0.056 Uiso 1 1 calc R U . . .
C14 C 0.8778(3) 0.5036(5) 0.6976(2) 0.0702(12) Uani 1 1 d . U . . .
H14 H 0.935354 0.450432 0.705898 0.084 Uiso 1 1 calc R U . . .
C15 C 0.8630(4) 0.5474(6) 0.7726(2) 0.1017(18) Uani 1 1 d . U . . .
H15 H 0.911186 0.523529 0.834025 0.122 Uiso 1 1 calc R U . . .
C17 C 0.7069(3) 0.6611(5) 0.6735(2) 0.0677(12) Uani 1 1 d . U . . .
H17 H 0.649024 0.713246 0.665257 0.081 Uiso 1 1 calc R U . . .
C16 C 0.7790(4) 0.6261(6) 0.7611(2) 0.1016(19) Uani 1 1 d . U . . .
H16 H 0.771655 0.655921 0.814783 0.122 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 N1 H1 123.9 . . ?
C1 N1 C8 112.1(2) . . ?
C8 N1 H1 123.9 . . ?
O1 C1 N1 127.4(3) . . ?
O1 C1 C2 124.7(3) . . ?
N1 C1 C2 107.7(2) . . ?
C3 C8 N1 109.4(2) . . ?
C7 C8 N1 128.4(3) . . ?
C7 C8 C3 122.3(3) . . ?
C8 C3 C2 108.6(2) . . ?
C4 C3 C8 120.0(2) . . ?
C4 C3 C2 131.4(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
O5 C22 C18 126.3(3) . . ?
O5 C22 C21 125.3(3) . . ?
C21 C22 C18 108.4(2) . . ?
C8 C7 C6 117.3(3) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C22 C18 H18 107.8 . . ?
C22 C18 C2 113.8(2) . . ?
C22 C18 C19 103.6(2) . . ?
C2 C18 H18 107.8 . . ?
C19 C18 H18 107.8 . . ?
C19 C18 C2 115.7(2) . . ?
C20 C21 C22 109.6(2) . . ?
C26 C21 C22 128.5(3) . . ?
C26 C21 C20 121.9(3) . . ?
C1 C2 C18 107.4(2) . . ?
C3 C2 C1 101.7(2) . . ?
C3 C2 C18 113.2(2) . . ?
C3 C2 C9 112.6(2) . . ?
C9 C2 C1 110.1(2) . . ?
C9 C2 C18 111.2(2) . . ?
O2 C10 C9 125.5(2) . . ?
O2 C10 C11 127.1(3) . . ?
C11 C10 C9 107.4(2) . . ?
C2 C9 H9 107.6 . . ?
C10 C9 C2 113.7(2) . . ?
C10 C9 H9 107.6 . . ?
C13 C9 C2 116.3(2) . . ?
C13 C9 C10 103.6(2) . . ?
C13 C9 H9 107.6 . . ?
O3 C13 C9 126.3(2) . . ?
O3 C13 C12 125.8(3) . . ?
C12 C13 C9 107.8(2) . . ?
C21 C20 C19 110.6(2) . . ?
C23 C20 C21 121.0(3) . . ?
C23 C20 C19 128.4(3) . . ?
O4 C19 C18 126.1(2) . . ?
O4 C19 C20 126.2(3) . . ?
C20 C19 C18 107.6(2) . . ?
C12 C11 C10 110.0(2) . . ?
C12 C11 C14 121.2(3) . . ?
C14 C11 C10 128.8(3) . . ?
C20 C23 H23 121.4 . . ?
C20 C23 C24 117.2(3) . . ?
C24 C23 H23 121.4 . . ?
C21 C26 H26 121.7 . . ?
C21 C26 C25 116.6(3) . . ?
C25 C26 H26 121.7 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.5(3) . . ?
C25 C24 H24 119.3 . . ?
C11 C12 C13 110.6(2) . . ?
C11 C12 C17 121.5(3) . . ?
C17 C12 C13 127.9(3) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 C26 121.9(3) . . ?
C24 C25 H25 119.1 . . ?
C11 C14 H14 121.3 . . ?
C15 C14 C11 117.3(4) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
C12 C17 H17 121.4 . . ?
C16 C17 C12 117.2(3) . . ?
C16 C17 H17 121.4 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
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 1.216(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.343(4) . ?
N1 C8 1.403(3) . ?
O3 C13 1.211(3) . ?
O5 C22 1.211(3) . ?
O2 C10 1.203(3) . ?
O4 C19 1.205(3) . ?
C1 C2 1.547(4) . ?
C8 C3 1.387(4) . ?
C8 C7 1.366(4) . ?
C3 C4 1.376(4) . ?
C3 C2 1.510(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C5 C4 1.377(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(4) . ?
C4 H4 0.9500 . ?
C22 C18 1.531(4) . ?
C22 C21 1.473(4) . ?
C7 H7 0.9500 . ?
C18 H18 1.0000 . ?
C18 C2 1.550(4) . ?
C18 C19 1.533(4) . ?
C21 C20 1.395(4) . ?
C21 C26 1.379(4) . ?
C2 C9 1.538(3) . ?
C10 C9 1.528(4) . ?
C10 C11 1.471(4) . ?
C9 H9 1.0000 . ?
C9 C13 1.519(4) . ?
C13 C12 1.460(4) . ?
C20 C19 1.476(4) . ?
C20 C23 1.381(4) . ?
C11 C12 1.378(4) . ?
C11 C14 1.386(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(4) . ?
C26 H26 0.9500 . ?
C26 C25 1.393(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.371(5) . ?
C12 C17 1.394(4) . ?
C25 H25 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.370(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.372(5) . ?
C16 H16 0.9500 . ?
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 -177.5(3) . . . . ?
O1 C1 C2 C18 63.4(3) . . . . ?
O1 C1 C2 C9 -57.9(3) . . . . ?
N1 C1 C2 C3 6.3(3) . . . . ?
N1 C1 C2 C18 -112.8(2) . . . . ?
N1 C1 C2 C9 125.9(2) . . . . ?
N1 C8 C3 C4 -177.7(2) . . . . ?
N1 C8 C3 C2 1.2(3) . . . . ?
N1 C8 C7 C6 176.6(3) . . . . ?
O3 C13 C12 C11 176.3(3) . . . . ?
O3 C13 C12 C17 -1.6(6) . . . . ?
O5 C22 C18 C2 -51.5(4) . . . . ?
O5 C22 C18 C19 -178.0(3) . . . . ?
O5 C22 C21 C20 179.9(3) . . . . ?
O5 C22 C21 C26 0.4(5) . . . . ?
O2 C10 C9 C2 45.1(4) . . . . ?
O2 C10 C9 C13 172.2(3) . . . . ?
O2 C10 C11 C12 -174.8(3) . . . . ?
O2 C10 C11 C14 3.2(6) . . . . ?
C1 N1 C8 C3 3.2(3) . . . . ?
C1 N1 C8 C7 -176.5(3) . . . . ?
C1 C2 C9 C10 -65.4(3) . . . . ?
C1 C2 C9 C13 174.4(2) . . . . ?
C8 N1 C1 O1 177.8(3) . . . . ?
C8 N1 C1 C2 -6.1(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C8 C3 C2 C1 -4.4(3) . . . . ?
C8 C3 C2 C18 110.5(2) . . . . ?
C8 C3 C2 C9 -122.3(2) . . . . ?
C3 C8 C7 C6 -3.1(4) . . . . ?
C3 C2 C9 C10 47.4(3) . . . . ?
C3 C2 C9 C13 -72.8(3) . . . . ?
C5 C6 C7 C8 2.4(4) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C4 C3 C2 C1 174.3(3) . . . . ?
C4 C3 C2 C18 -70.7(4) . . . . ?
C4 C3 C2 C9 56.5(4) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C22 C18 C2 C1 -57.7(3) . . . . ?
C22 C18 C2 C3 -169.1(2) . . . . ?
C22 C18 C2 C9 62.9(3) . . . . ?
C22 C18 C19 O4 178.2(3) . . . . ?
C22 C18 C19 C20 -3.2(3) . . . . ?
C22 C21 C20 C19 -1.8(3) . . . . ?
C22 C21 C20 C23 178.8(3) . . . . ?
C22 C21 C26 C25 -179.6(3) . . . . ?
C7 C8 C3 C4 2.1(4) . . . . ?
C7 C8 C3 C2 -179.0(2) . . . . ?
C18 C22 C21 C20 -0.4(3) . . . . ?
C18 C22 C21 C26 -179.9(3) . . . . ?
C18 C2 C9 C10 175.7(2) . . . . ?
C18 C2 C9 C13 55.5(3) . . . . ?
C21 C22 C18 C2 128.7(2) . . . . ?
C21 C22 C18 C19 2.2(3) . . . . ?
C21 C20 C19 O4 -178.2(3) . . . . ?
C21 C20 C19 C18 3.3(3) . . . . ?
C21 C20 C23 C24 0.6(4) . . . . ?
C21 C26 C25 C24 0.9(5) . . . . ?
C2 C3 C4 C5 -178.8(3) . . . . ?
C2 C18 C19 O4 52.9(4) . . . . ?
C2 C18 C19 C20 -128.5(2) . . . . ?
C2 C9 C13 O3 -48.4(4) . . . . ?
C2 C9 C13 C12 133.0(3) . . . . ?
C10 C9 C13 O3 -173.8(3) . . . . ?
C10 C9 C13 C12 7.5(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C10 C11 C12 C17 178.1(3) . . . . ?
C10 C11 C14 C15 -177.9(4) . . . . ?
C9 C10 C11 C12 4.9(4) . . . . ?
C9 C10 C11 C14 -177.1(4) . . . . ?
C9 C13 C12 C11 -5.0(4) . . . . ?
C9 C13 C12 C17 177.1(4) . . . . ?
C13 C12 C17 C16 178.4(4) . . . . ?
C20 C21 C26 C25 0.9(4) . . . . ?
C20 C23 C24 C25 1.2(5) . . . . ?
C19 C18 C2 C1 62.2(3) . . . . ?
C19 C18 C2 C3 -49.3(3) . . . . ?
C19 C18 C2 C9 -177.3(2) . . . . ?
C19 C20 C23 C24 -178.7(3) . . . . ?
C11 C10 C9 C2 -134.6(2) . . . . ?
C11 C10 C9 C13 -7.5(3) . . . . ?
C11 C12 C17 C16 0.6(6) . . . . ?
C11 C14 C15 C16 -0.3(8) . . . . ?
C23 C20 C19 O4 1.2(5) . . . . ?
C23 C20 C19 C18 -177.4(3) . . . . ?
C23 C24 C25 C26 -2.0(5) . . . . ?
C26 C21 C20 C19 177.7(3) . . . . ?
C26 C21 C20 C23 -1.7(5) . . . . ?
C12 C11 C14 C15 -0.1(6) . . . . ?
C12 C17 C16 C15 -1.1(8) . . . . ?
C14 C11 C12 C13 -178.2(3) . . . . ?
C14 C11 C12 C17 -0.1(6) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?
