#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:50:51 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290856 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/09/1570970.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_1570970
loop_
_publ_author_name
'Qian, Chenxiao'
'Huang, Jing'
'Huang, Tingting'
'Song, Lijuan'
'Sun, Jianwei'
'Li, Pengfei'
_publ_section_title
;
 Organocatalytic enantioselective synthesis of
 C<sub>sp₂</sub>-N atropisomers via formal
 C<sub>sp₂</sub>-O bond amination.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              3893
_journal_page_last               3900
_journal_paper_doi               10.1039/d3sc06707f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C27 H19 N O2, C1.5 H3 O0.5'
_chemical_formula_sum            'C28.5 H22 N O2.5'
_chemical_formula_weight         418.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.150(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.218(2)
_cell_length_b                   10.8756(7)
_cell_length_c                   17.0557(12)
_cell_measurement_reflns_used    8495
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.39
_cell_volume                     4331.7(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1525 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.9194.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0489
_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)+(0.0508P)²+3.6210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             4998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc06707f2.cif
_cod_data_source_block           cxy1959_0m
_cod_depositor_comments
'Adding full bibliography for 1570969--1570971.cif.'
_cod_original_formula_sum        'C28.50 H22 N O2.50'
_cod_database_code               1570970
_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   0.977
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C24(H24), C23(H23), C14(H14), C26(H26), C17(H17), C27(H27), C5(H5),
 C20(H20), C25(H25), C8(H8), C6(H6), C7(H7), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.49824(5) 1.05653(10) 0.60282(8) 0.0193(3) Uani 1 1 d . . . . .
O2 O 0.24870(5) 0.59514(10) 0.30357(8) 0.0190(3) Uani 1 1 d . . . . .
N1 N 0.45091(6) 0.89579(12) 0.49851(10) 0.0173(3) Uani 1 1 d . . . . .
H1 H 0.468349 0.899549 0.469026 0.021 Uiso 1 1 d R U . . .
C22 C 0.37960(7) 0.50580(14) 0.37143(12) 0.0148(3) Uani 1 1 d . . . . .
C12 C 0.25377(7) 0.60465(14) 0.23706(12) 0.0146(3) Uani 1 1 d . . . . .
C15 C 0.27063(7) 0.60007(14) 0.08414(11) 0.0160(4) Uani 1 1 d . . . . .
C1 C 0.46282(7) 0.97224(14) 0.57107(11) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.39039(7) 0.83756(15) 0.54152(11) 0.0162(4) Uani 1 1 d . . . . .
C9 C 0.38682(7) 0.72342(15) 0.41166(12) 0.0167(4) Uani 1 1 d . . . . .
C4 C 0.42416(7) 0.93450(14) 0.59965(11) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.20848(7) 0.56856(14) 0.14081(11) 0.0161(4) Uani 1 1 d . . . . .
H13 H 0.172261 0.544797 0.127492 0.019 Uiso 1 1 calc R U . . .
C2 C 0.40742(7) 0.81005(14) 0.47620(11) 0.0160(4) Uani 1 1 d . . . . .
C24 C 0.36702(7) 0.28987(15) 0.33246(12) 0.0180(4) Uani 1 1 d . . . . .
H24 H 0.345801 0.225769 0.288507 0.022 Uiso 1 1 calc R U . . .
C23 C 0.34955(7) 0.41082(14) 0.30719(12) 0.0150(3) Uani 1 1 d . . . . .
H23 H 0.316917 0.429106 0.245734 0.018 Uiso 1 1 calc R U . . .
C10 C 0.35993(7) 0.63611(14) 0.34881(11) 0.0146(3) Uani 1 1 d . . . . .
C16 C 0.31597(7) 0.64439(14) 0.17250(12) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.30667(7) 0.66815(14) 0.25074(11) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.21670(7) 0.56811(14) 0.07080(12) 0.0179(4) Uani 1 1 d . . . . .
H14 H 0.185516 0.545632 0.009068 0.021 Uiso 1 1 calc R U . . .
C26 C 0.44580(7) 0.35514(16) 0.48513(12) 0.0208(4) Uani 1 1 d . . . . .
H26 H 0.479050 0.336434 0.545802 0.025 Uiso 1 1 calc R U . . .
C17 C 0.36732(7) 0.67531(16) 0.18382(12) 0.0211(4) Uani 1 1 d . . . . .
H17 H 0.398183 0.706052 0.243023 0.025 Uiso 1 1 calc R U . . .
C21 C 0.29153(7) 0.80650(14) 0.24520(12) 0.0178(4) Uani 1 1 d . . . . .
H21A H 0.256422 0.824229 0.183222 0.027 Uiso 1 1 calc R U . . .
H21B H 0.322986 0.856497 0.253674 0.027 Uiso 1 1 calc R U . . .
H21C H 0.285631 0.826111 0.295222 0.027 Uiso 1 1 calc R U . . .
C27 C 0.42803(7) 0.47585(15) 0.46068(12) 0.0183(4) Uani 1 1 d . . . . .
H27 H 0.449082 0.539447 0.505266 0.022 Uiso 1 1 calc R U . . .
C5 C 0.41745(7) 0.98187(15) 0.66849(12) 0.0196(4) Uani 1 1 d . . . . .
H5 H 0.440905 1.047027 0.708853 0.023 Uiso 1 1 calc R U . . .
C20 C 0.27825(8) 0.58610(15) 0.01047(12) 0.0211(4) Uani 1 1 d . . . . .
H20 H 0.247763 0.555036 -0.048956 0.025 Uiso 1 1 calc R U . . .
C25 C 0.41498(7) 0.26148(15) 0.42091(12) 0.0203(4) Uani 1 1 d . . . . .
H25 H 0.426759 0.178363 0.437615 0.024 Uiso 1 1 calc R U . . .
C8 C 0.34816(7) 0.78592(15) 0.54923(12) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.325115 0.719878 0.509556 0.023 Uiso 1 1 calc R U . . .
C6 C 0.37532(8) 0.93053(16) 0.67604(12) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.369665 0.961297 0.722333 0.027 Uiso 1 1 calc R U . . .
C7 C 0.34091(7) 0.83436(16) 0.61699(12) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.312040 0.801628 0.623420 0.026 Uiso 1 1 calc R U . . .
C19 C 0.32949(8) 0.61683(17) 0.02293(13) 0.0251(4) Uani 1 1 d . . . . .
H19 H 0.334279 0.607269 -0.027596 0.030 Uiso 1 1 calc R U . . .
C18 C 0.37394(8) 0.66180(18) 0.10982(13) 0.0261(4) Uani 1 1 d . . . . .
H18 H 0.409235 0.683526 0.118626 0.031 Uiso 1 1 calc R U . . .
O3 O 0.500000 0.5587(2) 0.250000 0.0791(10) Uani 1 2 d S T P . .
C28 C 0.500000 0.4480(3) 0.250000 0.0334(7) Uani 1 2 d S T P . .
C29 C 0.47212(10) 0.3751(2) 0.28741(16) 0.0476(6) Uani 1 1 d . . . . .
H29A H 0.457195 0.430941 0.313769 0.071 Uiso 1 1 calc R U . . .
H29B H 0.500266 0.319490 0.337164 0.071 Uiso 1 1 calc R U . . .
H29C H 0.440551 0.327008 0.235919 0.071 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 123.8 . . ?
C1 N1 C2 112.34(14) . . ?
C2 N1 H1 123.8 . . ?
C23 C22 C10 121.80(14) . . ?
C23 C22 C27 118.32(15) . . ?
C27 C22 C10 119.82(14) . . ?
O2 C12 C13 122.39(15) . . ?
O2 C12 C11 120.34(14) . . ?
C13 C12 C11 116.99(14) . . ?
C16 C15 C14 119.62(15) . . ?
C20 C15 C16 119.64(15) . . ?
C20 C15 C14 120.74(15) . . ?
O1 C1 N1 125.14(16) . . ?
O1 C1 C4 128.74(15) . . ?
N1 C1 C4 106.10(14) . . ?
C4 C3 C2 108.01(14) . . ?
C8 C3 C4 121.27(16) . . ?
C8 C3 C2 130.70(15) . . ?
C10 C9 C2 171.46(17) . . ?
C3 C4 C1 108.14(14) . . ?
C5 C4 C1 130.58(15) . . ?
C5 C4 C3 121.25(16) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.62(15) . . ?
C14 C13 H13 119.2 . . ?
N1 C2 C3 105.40(13) . . ?
C9 C2 N1 127.52(16) . . ?
C9 C2 C3 127.08(15) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C25 C24 C23 120.72(16) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.38(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C10 C11 119.48(13) . . ?
C9 C10 C22 121.13(15) . . ?
C9 C10 C11 119.38(14) . . ?
C15 C16 C11 119.85(14) . . ?
C17 C16 C15 118.81(16) . . ?
C17 C16 C11 121.12(15) . . ?
C12 C11 C21 102.44(12) . . ?
C10 C11 C12 109.66(13) . . ?
C10 C11 C21 110.74(13) . . ?
C16 C11 C12 114.93(13) . . ?
C16 C11 C10 111.84(13) . . ?
C16 C11 C21 106.77(13) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 C15 123.49(15) . . ?
C13 C14 H14 118.3 . . ?
C27 C26 H26 120.1 . . ?
C27 C26 C25 119.89(16) . . ?
C25 C26 H26 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.74(16) . . ?
C18 C17 H17 119.6 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.11(16) . . ?
C26 C27 H27 119.4 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.45(16) . . ?
C6 C5 H5 121.3 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.82(16) . . ?
C19 C20 H20 119.6 . . ?
C24 C25 C26 119.57(15) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C3 C8 H8 121.3 . . ?
C7 C8 C3 117.48(16) . . ?
C7 C8 H8 121.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.39(17) . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.15(17) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C20 C19 H19 120.3 . . ?
C20 C19 C18 119.43(17) . . ?
C18 C19 H19 120.3 . . ?
C17 C18 C19 120.55(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
O3 C28 C29 122.16(14) . 2_655 ?
O3 C28 C29 122.15(14) . . ?
C29 C28 C29 115.7(3) 2_655 . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 1.2350(19) . ?
O2 C12 1.2248(19) . ?
N1 H1 0.8800 . ?
N1 C1 1.367(2) . ?
N1 C2 1.413(2) . ?
C22 C23 1.394(2) . ?
C22 C10 1.492(2) . ?
C22 C27 1.398(2) . ?
C12 C13 1.458(2) . ?
C12 C11 1.539(2) . ?
C15 C16 1.406(2) . ?
C15 C14 1.449(2) . ?
C15 C20 1.397(2) . ?
C1 C4 1.481(2) . ?
C3 C4 1.393(2) . ?
C3 C2 1.471(2) . ?
C3 C8 1.389(2) . ?
C9 C2 1.311(2) . ?
C9 C10 1.309(2) . ?
C4 C5 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.338(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.386(2) . ?
C24 C25 1.382(2) . ?
C23 H23 0.9500 . ?
C10 C11 1.535(2) . ?
C16 C11 1.520(2) . ?
C16 C17 1.391(2) . ?
C11 C21 1.552(2) . ?
C14 H14 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C26 C25 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C27 H27 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.379(3) . ?
C25 H25 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(2) . ?
C7 H7 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.386(3) . ?
C18 H18 0.9500 . ?
O3 C28 1.204(3) . ?
C28 C29 1.489(3) . ?
C28 C29 1.489(3) 2_655 ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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 C4 C3 177.84(16) . . . . ?
O1 C1 C4 C5 -0.3(3) . . . . ?
O2 C12 C13 C14 -173.32(15) . . . . ?
O2 C12 C11 C10 37.33(19) . . . . ?
O2 C12 C11 C16 164.32(14) . . . . ?
O2 C12 C11 C21 -80.31(17) . . . . ?
N1 C1 C4 C3 -0.68(17) . . . . ?
N1 C1 C4 C5 -178.85(16) . . . . ?
C22 C10 C11 C12 63.61(18) . . . . ?
C22 C10 C11 C16 -65.11(18) . . . . ?
C22 C10 C11 C21 175.94(14) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C15 C16 C11 C12 18.0(2) . . . . ?
C15 C16 C11 C10 143.91(14) . . . . ?
C15 C16 C11 C21 -94.81(16) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C15 C20 C19 C18 0.2(3) . . . . ?
C1 N1 C2 C3 0.58(17) . . . . ?
C1 N1 C2 C9 -178.85(16) . . . . ?
C1 C4 C5 C6 176.89(16) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C3 C8 C7 C6 -0.8(2) . . . . ?
C9 C10 C11 C12 -115.37(16) . . . . ?
C9 C10 C11 C16 115.91(17) . . . . ?
C9 C10 C11 C21 -3.0(2) . . . . ?
C4 C3 C2 N1 -1.00(17) . . . . ?
C4 C3 C2 C9 178.44(16) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C13 C12 C11 C10 -148.59(13) . . . . ?
C13 C12 C11 C16 -21.60(19) . . . . ?
C13 C12 C11 C21 93.77(16) . . . . ?
C2 N1 C1 O1 -178.56(15) . . . . ?
C2 N1 C1 C4 0.03(17) . . . . ?
C2 C3 C4 C1 1.04(17) . . . . ?
C2 C3 C4 C5 179.41(14) . . . . ?
C2 C3 C8 C7 -178.06(16) . . . . ?
C23 C22 C10 C9 176.28(16) . . . . ?
C23 C22 C10 C11 -2.7(2) . . . . ?
C23 C22 C27 C26 -0.2(2) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C10 C22 C23 C24 -176.12(15) . . . . ?
C10 C22 C27 C26 177.11(15) . . . . ?
C16 C15 C14 C13 -5.7(2) . . . . ?
C16 C15 C20 C19 -0.9(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C11 C12 C13 C14 12.7(2) . . . . ?
C11 C16 C17 C18 -175.19(15) . . . . ?
C14 C15 C16 C11 -4.9(2) . . . . ?
C14 C15 C16 C17 -179.62(15) . . . . ?
C14 C15 C20 C19 179.80(15) . . . . ?
C17 C16 C11 C12 -167.38(14) . . . . ?
C17 C16 C11 C10 -41.5(2) . . . . ?
C17 C16 C11 C21 79.77(18) . . . . ?
C27 C22 C23 C24 1.1(2) . . . . ?
C27 C22 C10 C9 -0.9(2) . . . . ?
C27 C22 C10 C11 -179.88(15) . . . . ?
C27 C26 C25 C24 0.7(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C20 C15 C16 C11 175.78(14) . . . . ?
C20 C15 C16 C17 1.1(2) . . . . ?
C20 C15 C14 C13 173.58(15) . . . . ?
C20 C19 C18 C17 0.3(3) . . . . ?
C25 C24 C23 C22 -1.2(2) . . . . ?
C25 C26 C27 C22 -0.7(3) . . . . ?
C8 C3 C4 C1 -177.37(14) . . . . ?
C8 C3 C4 C5 1.0(2) . . . . ?
C8 C3 C2 N1 177.20(16) . . . . ?
C8 C3 C2 C9 -3.4(3) . . . . ?
