#------------------------------------------------------------------------------
#$Date: 2024-10-06 08:26:21 +0200 (Sun 06 de Oct de 2024) $
#$Revision: 295158 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133495.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_7133495
loop_
_publ_author_name
'Yamada, Shinji'
'Honda, Yuka'
_publ_section_title
;
 Solid-state [2+2] photodimerization of eniminium salts: stereoselective
 syntheses of 1,3-diacetylcyclobutanes.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9821
_journal_page_last               9824
_journal_paper_doi               10.1039/d4cc03691c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H22 F2 O2'
_chemical_formula_sum            'C20 H22 F2 O2'
_chemical_formula_weight         332.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0hp
_audit_update_record
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.7120
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   15.5432
_cell_length_b                   10.8346
_cell_length_c                   20.4290
_cell_measurement_reflns_used    4531
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.34
_cell_volume                     3400.639
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         4.080
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1408.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.51
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1892
_refine_ls_R_factor_gt           0.0991
_refine_ls_shift/su_max          0.112
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3753
_refine_ls_wR_factor_ref         0.4346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1626
_reflns_number_total             6221
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d4cc03691c2.cif
_cod_data_source_block           DIOL-DIMER-3
_cod_depositor_comments
'Adding full bibliography for 7133484--7133496.cif.'
_cod_original_cell_volume        3400.6556
_cod_database_code               7133495
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,-1/2+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
F1 F 0.43061(18) 0.8575(3) -0.51409(13) 0.0613(11) Uani 1 1 d . . . . .
F2 F 0.07024(18) 0.8924(3) 0.01455(13) 0.0627(11) Uani 1 1 d . . . . .
F3 F 0.9306(2) 0.6072(3) -0.01375(16) 0.0737(12) Uani 1 1 d . . . . .
F4 F 0.5699(2) 0.6423(3) 0.51410(16) 0.0752(12) Uani 1 1 d . . . . .
O1 O 0.4096(2) 1.0738(3) -0.25650(15) 0.0517(11) Uani 1 1 d . . . . .
H1 H 0.3831 1.0681 -0.2954 0.062 Uiso 1 1 calc R U . . .
O2 O 0.0903(3) 0.6763(4) -0.2439(3) 0.1118(19) Uani 1 1 d . . . . .
H2A H 0.1039 0.6907 -0.2032 0.134 Uiso 1 1 calc R U . . .
O3 O 0.9088(2) 0.8237(4) 0.24346(17) 0.0617(12) Uani 1 1 d . . . . .
H3A H 0.8867 0.8144 0.2037 0.074 Uiso 1 1 calc R U . . .
O4 O 0.5911(3) 0.4260(5) 0.2565(3) 0.146(2) Uani 1 1 d . . . . .
H4 H 0.6105 0.4366 0.2967 0.175 Uiso 1 1 calc R U . . .
C1 C 0.3856(3) 0.8725(5) -0.4628(2) 0.0427(15) Uani 1 1 d . . . . .
C2 C 0.3993(3) 0.7880(5) -0.4116(2) 0.0446(15) Uani 1 1 d . . . . .
H2 H 0.4396 0.7223 -0.4122 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3524(3) 0.8016(5) -0.3594(2) 0.0431(14) Uani 1 1 d . . . . .
H3 H 0.3603 0.7436 -0.3242 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2937(3) 0.8989(5) -0.3575(2) 0.0395(14) Uani 1 1 d . . . . .
C5 C 0.2826(3) 0.9804(5) -0.4104(2) 0.0421(15) Uani 1 1 d . . . . .
H5 H 0.2425 1.0467 -0.4104 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3281(3) 0.9681(5) -0.4631(2) 0.0470(16) Uani 1 1 d . . . . .
H6 H 0.3196 1.0250 -0.4988 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2427(3) 0.9149(5) -0.3008(2) 0.0365(14) Uani 1 1 d . . . . .
H7 H 0.1927 0.9721 -0.3146 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2907(3) 0.9540(5) -0.2305(2) 0.0326(13) Uani 1 1 d . . . . .
H8 H 0.2622 1.0287 -0.2146 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2575(3) 0.8353(5) -0.1992(2) 0.0372(14) Uani 1 1 d . . . . .
H9 H 0.3075 0.7782 -0.1855 0.045 Uiso 1 1 calc R U . . .
C10 C 0.2091(3) 0.7965(5) -0.2694(2) 0.0408(14) Uani 1 1 d . . . . .
H10 H 0.2374 0.7218 -0.2854 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3891(3) 0.9696(5) -0.2189(2) 0.0369(14) Uani 1 1 d . . . . .
H11 H 0.4171 0.8940 -0.2343 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4225(3) 0.9913(5) -0.1470(2) 0.0475(15) Uani 1 1 d . . . . .
H12A H 0.4859 1.0012 -0.1409 0.057 Uiso 1 1 calc R U . . .
H12B H 0.4075 0.9207 -0.1210 0.057 Uiso 1 1 calc R U . . .
H12C H 0.3959 1.0663 -0.1322 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2064(3) 0.8520(5) -0.1424(2) 0.0415(15) Uani 1 1 d . . . . .
C14 C 0.2185(3) 0.7685(5) -0.0894(2) 0.0419(15) Uani 1 1 d . . . . .
H14 H 0.2587 0.7025 -0.0894 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1718(3) 0.7819(5) -0.0368(2) 0.0462(15) Uani 1 1 d . . . . .
H15 H 0.1794 0.7246 -0.0012 0.055 Uiso 1 1 calc R U . . .
C16 C 0.1153(3) 0.8777(5) -0.0369(3) 0.0433(15) Uani 1 1 d . . . . .
C17 C 0.1008(3) 0.9628(5) -0.0884(3) 0.0509(16) Uani 1 1 d . . . . .
H17 H 0.0606 1.0287 -0.0880 0.061 Uiso 1 1 calc R U . . .
C18 C 0.1478(3) 0.9472(6) -0.1404(2) 0.0513(16) Uani 1 1 d . . . . .
H18 H 0.1392 1.0042 -0.1762 0.062 Uiso 1 1 calc R U . . .
C19 C 0.1114(4) 0.7811(5) -0.2810(3) 0.0534(16) Uani 1 1 d . . . . .
H19 H 0.0833 0.8566 -0.2656 0.064 Uiso 1 1 calc R U . . .
C20 C 0.0777(4) 0.7588(6) -0.3528(3) 0.088(2) Uani 1 1 d . . . . .
H20A H 0.0141 0.7520 -0.3590 0.106 Uiso 1 1 calc R U . . .
H20B H 0.1025 0.6821 -0.3672 0.106 Uiso 1 1 calc R U . . .
H20C H 0.0944 0.8278 -0.3793 0.106 Uiso 1 1 calc R U . . .
C21 C 0.8863(4) 0.6191(6) 0.0375(3) 0.0555(18) Uani 1 1 d . . . . .
C22 C 0.8970(4) 0.5378(5) 0.0879(3) 0.0515(16) Uani 1 1 d . . . . .
H22 H 0.9364 0.4710 0.0872 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8516(3) 0.5500(5) 0.1403(2) 0.0470(15) Uani 1 1 d . . . . .
H23 H 0.8600 0.4915 0.1753 0.056 Uiso 1 1 calc R U . . .
C24 C 0.7928(3) 0.6486(5) 0.1426(3) 0.0437(15) Uani 1 1 d . . . . .
C25 C 0.7828(3) 0.7301(5) 0.0906(3) 0.0475(16) Uani 1 1 d . . . . .
H25 H 0.7433 0.7970 0.0910 0.057 Uiso 1 1 calc R U . . .
C26 C 0.8284(3) 0.7188(5) 0.0372(3) 0.0509(16) Uani 1 1 d . . . . .
H26 H 0.8205 0.7764 0.0018 0.061 Uiso 1 1 calc R U . . .
C27 C 0.7435(3) 0.6647(5) 0.1990(2) 0.0422(15) Uani 1 1 d . . . . .
H27 H 0.6935 0.7217 0.1852 0.051 Uiso 1 1 calc R U . . .
C28 C 0.7096(4) 0.5475(5) 0.2302(2) 0.0493(15) Uani 1 1 d . . . . .
H28 H 0.7379 0.4725 0.2145 0.059 Uiso 1 1 calc R U . . .
C29 C 0.7573(3) 0.5858(5) 0.3007(2) 0.0426(15) Uani 1 1 d . . . . .
H29 H 0.8075 0.5289 0.3143 0.051 Uiso 1 1 calc R U . . .
C30 C 0.7901(3) 0.7040(5) 0.2694(2) 0.0389(14) Uani 1 1 d . . . . .
H30 H 0.7615 0.7788 0.2850 0.047 Uiso 1 1 calc R U . . .
C31 C 0.6115(4) 0.5313(6) 0.2195(3) 0.069(2) Uani 1 1 d . . . . .
H31 H 0.5836 0.6064 0.2354 0.083 Uiso 1 1 calc R U . . .
C32 C 0.7074(3) 0.6020(5) 0.3576(3) 0.0444(15) Uani 1 1 d . . . . .
C33 C 0.6487(4) 0.6988(5) 0.3610(3) 0.0580(17) Uani 1 1 d . . . . .
H33 H 0.6400 0.7571 0.3259 0.070 Uiso 1 1 calc R U . . .
C34 C 0.6032(4) 0.7126(5) 0.4131(3) 0.0621(18) Uani 1 1 d . . . . .
H34 H 0.5638 0.7793 0.4139 0.075 Uiso 1 1 calc R U . . .
C35 C 0.6152(4) 0.6301(6) 0.4634(3) 0.0558(18) Uani 1 1 d . . . . .
C36 C 0.6719(4) 0.5309(5) 0.4631(3) 0.0515(16) Uani 1 1 d . . . . .
H36 H 0.6789 0.4726 0.4982 0.062 Uiso 1 1 calc R U . . .
C37 C 0.7181(3) 0.5191(5) 0.4101(2) 0.0458(16) Uani 1 1 d . . . . .
H37 H 0.7579 0.4526 0.4099 0.055 Uiso 1 1 calc R U . . .
C38 C 0.8884(3) 0.7193(5) 0.2812(2) 0.0404(14) Uani 1 1 d . . . . .
H38 H 0.9162 0.6437 0.2655 0.048 Uiso 1 1 calc R U . . .
C39 C 0.9230(3) 0.7411(5) 0.3532(2) 0.0554(17) Uani 1 1 d . . . . .
H39A H 0.9863 0.7528 0.3585 0.066 Uiso 1 1 calc R U . . .
H39B H 0.9096 0.6697 0.3793 0.066 Uiso 1 1 calc R U . . .
H39C H 0.8958 0.8151 0.3686 0.066 Uiso 1 1 calc R U . . .
C40 C 0.5771(4) 0.5102(6) 0.1469(3) 0.109(3) Uani 1 1 d . . . . .
H40A H 0.5138 0.5001 0.1412 0.131 Uiso 1 1 calc R U . . .
H40B H 0.6036 0.4355 0.1316 0.131 Uiso 1 1 calc R U . . .
H40C H 0.5917 0.5812 0.1210 0.131 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(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
C11 O1 H1 109.5 . . ?
C19 O2 H2A 109.5 . . ?
C38 O3 H3A 109.5 . . ?
C31 O4 H4 109.5 . . ?
F1 C1 C6 120.1(5) . . ?
F1 C1 C2 117.9(5) . . ?
C6 C1 C2 122.1(5) . . ?
C1 C2 C3 118.2(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.6(5) . . ?
C5 C4 C7 120.5(5) . . ?
C3 C4 C7 121.9(5) . . ?
C6 C5 C4 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C1 C6 C5 118.8(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C7 C10 117.9(4) . . ?
C4 C7 C8 120.0(4) . . ?
C10 C7 C8 89.3(3) . . ?
C4 C7 H7 109.3 . . ?
C10 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C11 C8 C9 114.5(4) . . ?
C11 C8 C7 120.0(4) . . ?
C9 C8 C7 90.7(3) . . ?
C11 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
C13 C9 C8 117.5(4) . . ?
C13 C9 C10 119.8(4) . . ?
C8 C9 C10 89.3(3) . . ?
C13 C9 H9 109.6 . . ?
C8 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C19 C10 C7 114.7(4) . . ?
C19 C10 C9 120.2(4) . . ?
C7 C10 C9 90.7(4) . . ?
C19 C10 H10 109.9 . . ?
C7 C10 H10 109.9 . . ?
C9 C10 H10 109.9 . . ?
O1 C11 C12 109.3(4) . . ?
O1 C11 C8 107.8(4) . . ?
C12 C11 C8 111.1(4) . . ?
O1 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
C8 C11 H11 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.1(5) . . ?
C18 C13 C9 122.4(5) . . ?
C14 C13 C9 119.4(5) . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
F2 C16 C15 119.8(5) . . ?
F2 C16 C17 117.7(5) . . ?
C15 C16 C17 122.5(5) . . ?
C18 C17 C16 117.1(5) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C13 C18 C17 122.6(5) . . ?
C13 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
O2 C19 C20 108.4(5) . . ?
O2 C19 C10 108.1(5) . . ?
C20 C19 C10 111.4(5) . . ?
O2 C19 H19 109.6 . . ?
C20 C19 H19 109.6 . . ?
C10 C19 H19 109.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F3 C21 C22 121.0(6) . . ?
F3 C21 C26 118.2(6) . . ?
C22 C21 C26 120.7(5) . . ?
C21 C22 C23 120.9(6) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C24 120.7(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 117.3(5) . . ?
C25 C24 C27 120.9(5) . . ?
C23 C24 C27 121.8(5) . . ?
C24 C25 C26 122.6(5) . . ?
C24 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C25 C26 C21 117.8(5) . . ?
C25 C26 H26 121.1 . . ?
C21 C26 H26 121.1 . . ?
C24 C27 C28 118.1(4) . . ?
C24 C27 C30 121.5(4) . . ?
C28 C27 C30 89.1(3) . . ?
C24 C27 H27 108.9 . . ?
C28 C27 H27 108.9 . . ?
C30 C27 H27 108.8 . . ?
C31 C28 C27 115.7(5) . . ?
C31 C28 C29 119.1(5) . . ?
C27 C28 C29 91.1(4) . . ?
C31 C28 H28 109.9 . . ?
C27 C28 H28 109.9 . . ?
C29 C28 H28 109.9 . . ?
C32 C29 C30 117.6(4) . . ?
C32 C29 C28 120.9(4) . . ?
C30 C29 C28 88.7(3) . . ?
C32 C29 H29 109.3 . . ?
C30 C29 H29 109.3 . . ?
C28 C29 H29 109.3 . . ?
C38 C30 C29 114.2(4) . . ?
C38 C30 C27 119.3(4) . . ?
C29 C30 C27 91.1(4) . . ?
C38 C30 H30 110.3 . . ?
C29 C30 H30 110.3 . . ?
C27 C30 H30 110.3 . . ?
O4 C31 C40 108.9(6) . . ?
O4 C31 C28 108.3(5) . . ?
C40 C31 C28 110.9(5) . . ?
O4 C31 H31 109.6 . . ?
C40 C31 H31 109.6 . . ?
C28 C31 H31 109.6 . . ?
C37 C32 C33 116.6(5) . . ?
C37 C32 C29 120.5(5) . . ?
C33 C32 C29 122.9(5) . . ?
C34 C33 C32 122.4(5) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C35 C34 C33 119.3(6) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.3 . . ?
F4 C35 C34 119.5(6) . . ?
F4 C35 C36 119.0(6) . . ?
C34 C35 C36 121.5(6) . . ?
C35 C36 C37 118.4(5) . . ?
C35 C36 H36 120.8 . . ?
C37 C36 H36 120.8 . . ?
C32 C37 C36 121.7(5) . . ?
C32 C37 H37 119.1 . . ?
C36 C37 H37 119.2 . . ?
O3 C38 C39 109.0(4) . . ?
O3 C38 C30 107.5(4) . . ?
C39 C38 C30 112.0(4) . . ?
O3 C38 H38 109.4 . . ?
C39 C38 H38 109.4 . . ?
C30 C38 H38 109.4 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C31 C40 H40A 109.5 . . ?
C31 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C31 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
F1 C1 1.355(5) . ?
F2 C16 1.358(5) . ?
F3 C21 1.344(5) . ?
F4 C35 1.345(5) . ?
O1 C11 1.428(5) . ?
O1 H1 0.8400 . ?
O2 C19 1.431(6) . ?
O2 H2A 0.8400 . ?
O3 C38 1.432(5) . ?
O3 H3A 0.8400 . ?
O4 C31 1.430(6) . ?
O4 H4 0.8400 . ?
C1 C6 1.368(7) . ?
C1 C2 1.381(6) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 C7 1.510(6) . ?
C5 C6 1.380(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C10 1.559(6) . ?
C7 C8 1.572(6) . ?
C7 H7 1.0000 . ?
C8 C11 1.522(6) . ?
C8 C9 1.559(6) . ?
C8 H8 1.0000 . ?
C9 C13 1.513(6) . ?
C9 C10 1.573(6) . ?
C9 H9 1.0000 . ?
C10 C19 1.511(6) . ?
C10 H10 1.0000 . ?
C11 C12 1.500(6) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.381(7) . ?
C13 C14 1.401(6) . ?
C14 C15 1.392(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.360(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(6) . ?
C17 C18 1.388(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.501(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.346(7) . ?
C21 C26 1.406(7) . ?
C22 C23 1.374(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.413(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(6) . ?
C24 C27 1.487(6) . ?
C25 C26 1.392(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.549(7) . ?
C27 C30 1.567(6) . ?
C27 H27 1.0000 . ?
C28 C31 1.517(7) . ?
C28 C29 1.573(6) . ?
C28 H28 1.0000 . ?
C29 C32 1.501(6) . ?
C29 C30 1.553(6) . ?
C29 H29 1.0000 . ?
C30 C38 1.519(6) . ?
C30 H30 1.0000 . ?
C31 C40 1.514(7) . ?
C31 H31 1.0000 . ?
C32 C37 1.390(6) . ?
C32 C33 1.399(7) . ?
C33 C34 1.373(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.352(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(7) . ?
C36 C37 1.392(6) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.507(6) . ?
C38 H38 1.0000 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
F1 C1 C2 C3 -179.0(4) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C2 C3 C4 C5 1.2(7) . . . . ?
C2 C3 C4 C7 -179.7(4) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C7 C4 C5 C6 -179.8(4) . . . . ?
F1 C1 C6 C5 179.4(4) . . . . ?
C2 C1 C6 C5 0.2(8) . . . . ?
C4 C5 C6 C1 0.1(8) . . . . ?
C5 C4 C7 C10 141.7(5) . . . . ?
C3 C4 C7 C10 -37.4(6) . . . . ?
C5 C4 C7 C8 -111.4(5) . . . . ?
C3 C4 C7 C8 69.5(6) . . . . ?
C4 C7 C8 C11 -3.0(7) . . . . ?
C10 C7 C8 C11 119.3(4) . . . . ?
C4 C7 C8 C9 -122.0(4) . . . . ?
C10 C7 C8 C9 0.3(4) . . . . ?
C11 C8 C9 C13 112.4(5) . . . . ?
C7 C8 C9 C13 -123.9(4) . . . . ?
C11 C8 C9 C10 -123.9(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C4 C7 C10 C19 -112.2(5) . . . . ?
C8 C7 C10 C19 123.7(4) . . . . ?
C4 C7 C10 C9 123.8(4) . . . . ?
C8 C7 C10 C9 -0.3(4) . . . . ?
C13 C9 C10 C19 2.6(7) . . . . ?
C8 C9 C10 C19 -119.1(5) . . . . ?
C13 C9 C10 C7 121.9(4) . . . . ?
C8 C9 C10 C7 0.3(4) . . . . ?
C9 C8 C11 O1 173.6(4) . . . . ?
C7 C8 C11 O1 67.4(5) . . . . ?
C9 C8 C11 C12 -66.7(5) . . . . ?
C7 C8 C11 C12 -172.8(4) . . . . ?
C8 C9 C13 C18 37.9(7) . . . . ?
C10 C9 C13 C18 -68.5(6) . . . . ?
C8 C9 C13 C14 -142.0(5) . . . . ?
C10 C9 C13 C14 111.5(5) . . . . ?
C18 C13 C14 C15 0.4(8) . . . . ?
C9 C13 C14 C15 -179.7(4) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 F2 -179.1(4) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
F2 C16 C17 C18 179.5(4) . . . . ?
C15 C16 C17 C18 -0.7(8) . . . . ?
C14 C13 C18 C17 0.0(8) . . . . ?
C9 C13 C18 C17 -180.0(4) . . . . ?
C16 C17 C18 C13 0.2(8) . . . . ?
C7 C10 C19 O2 -174.1(4) . . . . ?
C9 C10 C19 O2 -67.7(6) . . . . ?
C7 C10 C19 C20 66.8(6) . . . . ?
C9 C10 C19 C20 173.2(5) . . . . ?
F3 C21 C22 C23 -179.9(4) . . . . ?
C26 C21 C22 C23 0.0(9) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C22 C23 C24 C25 0.3(7) . . . . ?
C22 C23 C24 C27 -179.4(4) . . . . ?
C23 C24 C25 C26 -0.3(8) . . . . ?
C27 C24 C25 C26 179.4(4) . . . . ?
C24 C25 C26 C21 0.1(8) . . . . ?
F3 C21 C26 C25 180.0(4) . . . . ?
C22 C21 C26 C25 0.0(8) . . . . ?
C25 C24 C27 C28 142.3(5) . . . . ?
C23 C24 C27 C28 -38.0(6) . . . . ?
C25 C24 C27 C30 -109.9(6) . . . . ?
C23 C24 C27 C30 69.8(6) . . . . ?
C24 C27 C28 C31 -111.7(6) . . . . ?
C30 C27 C28 C31 122.6(5) . . . . ?
C24 C27 C28 C29 125.0(4) . . . . ?
C30 C27 C28 C29 -0.7(5) . . . . ?
C31 C28 C29 C32 2.1(7) . . . . ?
C27 C28 C29 C32 122.5(4) . . . . ?
C31 C28 C29 C30 -119.7(5) . . . . ?
C27 C28 C29 C30 0.7(5) . . . . ?
C32 C29 C30 C38 111.6(5) . . . . ?
C28 C29 C30 C38 -123.7(4) . . . . ?
C32 C29 C30 C27 -125.3(4) . . . . ?
C28 C29 C30 C27 -0.7(5) . . . . ?
C24 C27 C30 C38 -3.3(7) . . . . ?
C28 C27 C30 C38 119.5(4) . . . . ?
C24 C27 C30 C29 -122.1(5) . . . . ?
C28 C27 C30 C29 0.7(5) . . . . ?
C27 C28 C31 O4 -174.6(5) . . . . ?
C29 C28 C31 O4 -67.6(7) . . . . ?
C27 C28 C31 C40 66.0(7) . . . . ?
C29 C28 C31 C40 173.0(5) . . . . ?
C30 C29 C32 C37 -142.9(5) . . . . ?
C28 C29 C32 C37 110.7(6) . . . . ?
C30 C29 C32 C33 37.3(7) . . . . ?
C28 C29 C32 C33 -69.2(7) . . . . ?
C37 C32 C33 C34 0.0(8) . . . . ?
C29 C32 C33 C34 179.8(5) . . . . ?
C32 C33 C34 C35 0.1(9) . . . . ?
C33 C34 C35 F4 -179.0(5) . . . . ?
C33 C34 C35 C36 -0.7(9) . . . . ?
F4 C35 C36 C37 179.7(4) . . . . ?
C34 C35 C36 C37 1.3(9) . . . . ?
C33 C32 C37 C36 0.7(8) . . . . ?
C29 C32 C37 C36 -179.1(4) . . . . ?
C35 C36 C37 C32 -1.3(8) . . . . ?
C29 C30 C38 O3 173.7(4) . . . . ?
C27 C30 C38 O3 67.6(6) . . . . ?
C29 C30 C38 C39 -66.6(6) . . . . ?
C27 C30 C38 C39 -172.7(4) . . . . ?
