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#$Date: 2022-11-04 01:14:44 +0200 (Fri, 04 Nov 2022) $
#$Revision: 278932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/78/1567898.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_1567898
loop_
_publ_author_name
'He, Xinwei'
'Li, Ruxue'
'Choy, Pui Ying'
'Duan, Jiahui'
'Yin, Zhenzhen'
'Xu, Keke'
'Tang, Qiang'
'Zhong, RongLin'
'Shang, Yongjia'
'Kwong, Fuk Yee'
_publ_section_title
;
 An expeditious FeCl3-catalyzed cascade 1,4-conjugate
 addition/annulation/1,5-H shift sequence for modular access of
 all-pyrano-moiety-substituted chromenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04431E
_journal_year                    2022
_chemical_formula_moiety         'C28 H20 F N O2'
_chemical_formula_sum            'C28 H20 F N O2'
_chemical_formula_weight         421.45
_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
_audit_creation_date             2021-09-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.581(6)
_cell_angle_beta                 95.065(7)
_cell_angle_gamma                111.403(6)
_cell_formula_units_Z            2
_cell_length_a                   9.5747(19)
_cell_length_b                   9.6132(18)
_cell_length_c                   12.847(3)
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      23.137
_cell_measurement_theta_min      2.958
_cell_volume                     1061.5(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1059
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16838
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.668
_diffrn_reflns_theta_min         2.596
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0910 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.7269.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1646
_refine_ls_R_factor_gt           0.0686
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2196
_reflns_number_total             4695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04431e2.cif
_cod_data_source_block           20210930a
_cod_database_code               1567898
_shelx_shelxl_version_number     2018/3
_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   0.990
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C25(H25), C27(H27), C28(H28)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.2290(2) 0.5012(2) 0.44783(14) 0.0620(6) Uani 1 1 d . . . . .
O2 O 0.6485(2) 0.8696(2) 0.49042(14) 0.0639(6) Uani 1 1 d . . . . .
F1 F 0.2554(3) 1.1422(2) 0.89213(17) 0.1052(7) Uani 1 1 d . . . . .
N1 N 0.4014(3) 0.6532(2) 0.36855(16) 0.0534(6) Uani 1 1 d . . . . .
H1 H 0.486518 0.729895 0.374885 0.064 Uiso 1 1 calc R U . . .
C1 C 0.3661(3) 0.6190(3) 0.4621(2) 0.0474(7) Uani 1 1 d . . . . .
C2 C 0.4581(3) 0.6950(3) 0.56095(19) 0.0447(6) Uani 1 1 d . . . . .
C3 C 0.3993(3) 0.6614(3) 0.6633(2) 0.0487(7) Uani 1 1 d . . . . .
H3 H 0.482108 0.656125 0.710873 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2663(3) 0.5045(3) 0.6374(2) 0.0481(7) Uani 1 1 d . . . . .
C5 C 0.2179(3) 0.4263(3) 0.7155(2) 0.0595(8) Uani 1 1 d . . . . .
H5 H 0.269590 0.468942 0.786397 0.071 Uiso 1 1 calc R U . . .
C6 C 0.0944(4) 0.2862(3) 0.6904(3) 0.0674(9) Uani 1 1 d . . . . .
H6 H 0.063110 0.235739 0.744026 0.081 Uiso 1 1 calc R U . . .
C7 C 0.0175(4) 0.2216(4) 0.5850(3) 0.0721(9) Uani 1 1 d . . . . .
H7 H -0.066019 0.127737 0.567743 0.086 Uiso 1 1 calc R U . . .
C8 C 0.0642(3) 0.2955(3) 0.5060(3) 0.0680(9) Uani 1 1 d . . . . .
H8 H 0.013400 0.252490 0.434890 0.082 Uiso 1 1 calc R U . . .
C9 C 0.1881(3) 0.4353(3) 0.5338(2) 0.0530(7) Uani 1 1 d . . . . .
C10 C 0.3204(3) 0.5827(3) 0.2613(2) 0.0494(7) Uani 1 1 d . . . . .
C11 C 0.1639(4) 0.5112(3) 0.2345(2) 0.0596(8) Uani 1 1 d . . . . .
H11 H 0.104369 0.505123 0.288220 0.072 Uiso 1 1 calc R U . . .
C12 C 0.0956(4) 0.4480(3) 0.1262(3) 0.0708(9) Uani 1 1 d . . . . .
H12 H -0.009970 0.398744 0.108081 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1809(5) 0.4572(4) 0.0462(3) 0.0809(11) Uani 1 1 d . . . . .
H13 H 0.134099 0.413015 -0.025674 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3354(5) 0.5317(4) 0.0729(2) 0.0816(10) Uani 1 1 d . . . . .
H14 H 0.393959 0.540607 0.018678 0.098 Uiso 1 1 calc R U . . .
C15 C 0.4059(4) 0.5941(4) 0.1797(2) 0.0661(9) Uani 1 1 d . . . . .
H15 H 0.511430 0.644177 0.196886 0.079 Uiso 1 1 calc R U . . .
C16 C 0.6005(3) 0.8218(3) 0.5692(2) 0.0464(7) Uani 1 1 d . . . . .
C17 C 0.6968(3) 0.9037(3) 0.6793(2) 0.0441(6) Uani 1 1 d . . . . .
C18 C 0.7759(3) 0.8353(3) 0.7312(2) 0.0577(8) Uani 1 1 d . . . . .
H18 H 0.770451 0.737738 0.697873 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8624(4) 0.9105(3) 0.8317(2) 0.0702(9) Uani 1 1 d . . . . .
H19 H 0.916403 0.864100 0.865827 0.084 Uiso 1 1 calc R U . . .
C20 C 0.8701(4) 1.0527(3) 0.8823(2) 0.0642(9) Uani 1 1 d . . . . .
H20 H 0.928636 1.102748 0.950752 0.077 Uiso 1 1 calc R U . . .
C21 C 0.7914(4) 1.1217(3) 0.8319(2) 0.0639(8) Uani 1 1 d . . . . .
H21 H 0.795623 1.218320 0.866302 0.077 Uiso 1 1 calc R U . . .
C22 C 0.7056(3) 1.0472(3) 0.7297(2) 0.0537(7) Uani 1 1 d . . . . .
H22 H 0.653612 1.094834 0.695005 0.064 Uiso 1 1 calc R U . . .
C23 C 0.3558(3) 0.7886(3) 0.7241(2) 0.0488(7) Uani 1 1 d . . . . .
C24 C 0.3753(4) 0.8244(4) 0.8359(2) 0.0661(9) Uani 1 1 d . . . . .
H24 H 0.413380 0.768832 0.873472 0.079 Uiso 1 1 calc R U . . .
C25 C 0.3389(4) 0.9417(4) 0.8928(3) 0.0760(10) Uani 1 1 d . . . . .
H25 H 0.350779 0.964303 0.967717 0.091 Uiso 1 1 calc R U . . .
C26 C 0.2851(4) 1.0231(4) 0.8359(3) 0.0716(9) Uani 1 1 d . . . . .
C27 C 0.2647(4) 0.9923(4) 0.7262(3) 0.0696(9) Uani 1 1 d . . . . .
H27 H 0.227666 1.049064 0.689286 0.084 Uiso 1 1 calc R U . . .
C28 C 0.3006(3) 0.8744(3) 0.6714(2) 0.0570(8) Uani 1 1 d . . . . .
H28 H 0.287013 0.852244 0.596420 0.068 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'
F F 0.0171 0.0103 '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 118.92(19) . . ?
C1 N1 H1 114.9 . . ?
C1 N1 C10 130.2(2) . . ?
C10 N1 H1 114.9 . . ?
O1 C1 C2 123.5(2) . . ?
N1 C1 O1 112.4(2) . . ?
N1 C1 C2 124.1(2) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 C16 119.9(2) . . ?
C16 C2 C3 119.5(2) . . ?
C2 C3 H3 107.5 . . ?
C2 C3 C4 110.5(2) . . ?
C2 C3 C23 112.4(2) . . ?
C4 C3 H3 107.5 . . ?
C23 C3 H3 107.5 . . ?
C23 C3 C4 111.2(2) . . ?
C5 C4 C3 122.6(2) . . ?
C9 C4 C3 120.4(2) . . ?
C9 C4 C5 117.0(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C4 C9 O1 122.1(2) . . ?
C4 C9 C8 123.0(2) . . ?
C8 C9 O1 114.9(2) . . ?
C11 C10 N1 124.0(3) . . ?
C11 C10 C15 119.1(2) . . ?
C15 C10 N1 116.8(3) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.3(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
O2 C16 C2 123.9(2) . . ?
O2 C16 C17 117.8(2) . . ?
C2 C16 C17 118.2(2) . . ?
C18 C17 C16 120.8(2) . . ?
C22 C17 C16 120.1(2) . . ?
C22 C17 C18 119.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 120.3(3) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C3 120.3(3) . . ?
C28 C23 C3 121.9(2) . . ?
C28 C23 C24 117.8(3) . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.1(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.8 . . ?
C26 C25 C24 118.3(3) . . ?
C26 C25 H25 120.8 . . ?
F1 C26 C25 118.2(3) . . ?
C27 C26 F1 119.3(3) . . ?
C27 C26 C25 122.5(3) . . ?
C26 C27 H27 120.9 . . ?
C26 C27 C28 118.2(3) . . ?
C28 C27 H27 120.9 . . ?
C23 C28 C27 122.1(3) . . ?
C23 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
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 1.352(3) . ?
O1 C9 1.396(3) . ?
O2 C16 1.249(3) . ?
F1 C26 1.362(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.348(3) . ?
N1 C10 1.419(3) . ?
C1 C2 1.372(3) . ?
C2 C3 1.522(3) . ?
C2 C16 1.437(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.526(3) . ?
C3 C23 1.525(4) . ?
C4 C5 1.385(3) . ?
C4 C9 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(4) . ?
C10 C11 1.378(4) . ?
C10 C15 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.505(3) . ?
C17 C18 1.378(4) . ?
C17 C22 1.370(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.371(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(4) . ?
C23 C28 1.378(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.367(5) . ?
C26 C27 1.362(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(4) . ?
C28 H28 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.86 1.92 2.612(3) 136.5 . yes
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 -7.4(4) . . . . ?
O1 C1 C2 C16 -178.3(2) . . . . ?
O2 C16 C17 C18 -107.2(3) . . . . ?
O2 C16 C17 C22 73.4(3) . . . . ?
F1 C26 C27 C28 177.8(3) . . . . ?
N1 C1 C2 C3 172.2(2) . . . . ?
N1 C1 C2 C16 1.3(4) . . . . ?
N1 C10 C11 C12 178.8(2) . . . . ?
N1 C10 C15 C14 -178.5(3) . . . . ?
C1 O1 C9 C4 13.7(4) . . . . ?
C1 O1 C9 C8 -165.9(3) . . . . ?
C1 N1 C10 C11 30.0(4) . . . . ?
C1 N1 C10 C15 -153.0(3) . . . . ?
C1 C2 C3 C4 21.0(4) . . . . ?
C1 C2 C3 C23 -103.8(3) . . . . ?
C1 C2 C16 O2 0.0(4) . . . . ?
C1 C2 C16 C17 179.1(2) . . . . ?
C2 C3 C4 C5 162.1(3) . . . . ?
C2 C3 C4 C9 -18.5(4) . . . . ?
C2 C3 C23 C24 -146.8(2) . . . . ?
C2 C3 C23 C28 31.2(3) . . . . ?
C2 C16 C17 C18 73.6(3) . . . . ?
C2 C16 C17 C22 -105.8(3) . . . . ?
C3 C2 C16 O2 -171.0(3) . . . . ?
C3 C2 C16 C17 8.1(4) . . . . ?
C3 C4 C5 C6 178.2(3) . . . . ?
C3 C4 C9 O1 2.3(4) . . . . ?
C3 C4 C9 C8 -178.2(3) . . . . ?
C3 C23 C24 C25 178.8(3) . . . . ?
C3 C23 C28 C27 -178.3(3) . . . . ?
C4 C3 C23 C24 88.7(3) . . . . ?
C4 C3 C23 C28 -93.2(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C4 C9 O1 -178.3(2) . . . . ?
C5 C4 C9 C8 1.3(4) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 O1 179.1(3) . . . . ?
C7 C8 C9 C4 -0.5(5) . . . . ?
C9 O1 C1 N1 169.2(2) . . . . ?
C9 O1 C1 C2 -11.1(4) . . . . ?
C9 C4 C5 C6 -1.2(4) . . . . ?
C10 N1 C1 O1 -2.2(4) . . . . ?
C10 N1 C1 C2 178.1(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C10 C15 C14 -1.4(4) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C15 1.6(5) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C15 C10 C11 C12 1.9(4) . . . . ?
C16 C2 C3 C4 -168.1(2) . . . . ?
C16 C2 C3 C23 67.2(3) . . . . ?
C16 C17 C18 C19 -179.6(3) . . . . ?
C16 C17 C22 C21 178.6(2) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C17 C22 C21 -0.7(4) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C22 -0.5(5) . . . . ?
C20 C21 C22 C17 1.1(4) . . . . ?
C22 C17 C18 C19 -0.2(4) . . . . ?
C23 C3 C4 C5 -72.4(3) . . . . ?
C23 C3 C4 C9 107.0(3) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
C24 C23 C28 C27 -0.2(4) . . . . ?
C24 C25 C26 F1 -177.4(3) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C28 -0.2(5) . . . . ?
C26 C27 C28 C23 -0.1(5) . . . . ?
C28 C23 C24 C25 0.7(4) . . . . ?
