#------------------------------------------------------------------------------
#$Date: 2020-10-03 01:49:44 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135266.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_4135266
loop_
_publ_author_name
'Tan, Yan Bing'
'Okayasu, Yoshinori'
'Katao, Shohei'
'Nishikawa, Yoshiko'
'Asanoma, Fumio'
'Yamada, Mihoko'
'Yuasa, Junpei'
'Kawai, Tsuyoshi'
_publ_section_title
;
 Visible Circularly Polarized Luminescence of Octanuclear Circular Eu(III)
 Helicate.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c08229
_journal_year                    2020
_chemical_formula_moiety         'C24 H9 F21 O6'
_chemical_formula_sum            'C24 H9 F21 O6'
_chemical_formula_weight         792.30
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                80.974(6)
_cell_angle_beta                 89.293(6)
_cell_angle_gamma                82.793(6)
_cell_formula_units_Z            2
_cell_length_a                   5.0938(3)
_cell_length_b                   14.6539(10)
_cell_length_c                   18.6644(12)
_cell_measurement_reflns_used    11669
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      1.93
_cell_volume                     1365.03(15)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18516
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.432
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             780.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     463
_refine_ls_number_reflns         4983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0824P)²+0.5394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3800
_reflns_number_total             4983
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja0c08229_si_007.cif
_cod_data_source_block           expt226-2
_cod_original_cell_volume        1365.04(15)
_cod_database_code               4135266
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
F1 F 0.2495(4) 0.59647(12) 0.85501(9) 0.0370(5) Uani 1 1 d . . . . .
F2 F -0.1788(4) 0.61348(14) 0.86890(10) 0.0416(5) Uani 1 1 d . . . . .
F3 F 0.2556(4) 0.77210(15) 0.89459(10) 0.0497(5) Uani 1 1 d . . . . .
F4 F -0.1593(4) 0.77174(16) 0.92300(11) 0.0553(6) Uani 1 1 d . . . . .
F5 F 0.1513(5) 0.71954(18) 1.03758(11) 0.0703(8) Uani 1 1 d . . . . .
F6 F 0.3851(4) 0.61499(17) 0.98863(11) 0.0625(7) Uani 1 1 d . . . . .
F7 F -0.0201(6) 0.6023(2) 1.01189(12) 0.0773(8) Uani 1 1 d . . . . .
F8 F 1.0585(4) 0.92235(14) 0.26028(10) 0.0453(5) Uani 1 1 d . . . . .
F9 F 0.9385(4) 1.06949(13) 0.22361(10) 0.0406(5) Uani 1 1 d . . . . .
F10 F 0.5975(4) 0.88401(16) 0.20233(12) 0.0557(6) Uani 1 1 d . . . . .
F11 F 0.4998(4) 1.03134(16) 0.16030(10) 0.0530(6) Uani 1 1 d . . . . .
F12 F 0.9601(5) 1.02782(16) 0.08371(11) 0.0603(6) Uani 1 1 d . . . . .
F13 F 0.7029(5) 0.9299(2) 0.06089(12) 0.0727(8) Uani 1 1 d . . . . .
F14 F 1.0557(4) 0.88274(16) 0.12362(12) 0.0578(6) Uani 1 1 d . . . . .
F15 F 1.4243(4) 0.32043(12) 0.66325(10) 0.0395(5) Uani 1 1 d . . . . .
F16 F 1.0022(4) 0.34844(13) 0.68389(9) 0.0384(5) Uani 1 1 d . . . . .
F17 F 1.4863(4) 0.47762(13) 0.73230(9) 0.0374(5) Uani 1 1 d . . . . .
F18 F 1.0741(4) 0.47385(13) 0.76598(9) 0.0373(5) Uani 1 1 d . . . . .
F19 F 1.4125(5) 0.39128(16) 0.86880(10) 0.0558(6) Uani 1 1 d . . . . .
F20 F 1.6083(4) 0.29905(15) 0.80033(11) 0.0483(5) Uani 1 1 d . . . . .
F21 F 1.1992(4) 0.29197(15) 0.82830(11) 0.0524(6) Uani 1 1 d . . . . .
O1 O -0.0528(4) 0.83381(15) 0.64597(10) 0.0307(5) Uani 1 1 d . . . . .
O2 O -0.2364(4) 0.77089(16) 0.77320(11) 0.0334(5) Uani 1 1 d . . . . .
H2A H -0.240476 0.809935 0.734990 0.040 Uiso 1 1 calc R U . . .
O3 O 0.3312(4) 0.98363(15) 0.43020(11) 0.0332(5) Uani 1 1 d . . . . .
H3 H 0.355622 1.029229 0.398581 0.040 Uiso 1 1 calc R U . . .
O4 O 0.5186(4) 1.06508(15) 0.31111(11) 0.0333(5) Uani 1 1 d . . . . .
O5 O 1.1203(4) 0.62054(15) 0.49868(10) 0.0302(5) Uani 1 1 d . . . . .
H5 H 1.239164 0.574738 0.503847 0.036 Uiso 1 1 calc R U . . .
O6 O 1.3843(4) 0.46693(15) 0.56525(11) 0.0338(5) Uani 1 1 d . . . . .
C1 C 0.3503(6) 0.7682(2) 0.60041(15) 0.0267(7) Uani 1 1 d . . . . .
C2 C 0.3369(6) 0.8390(2) 0.54047(15) 0.0286(7) Uani 1 1 d . . . . .
H2 H 0.200402 0.890048 0.537237 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5233(6) 0.8350(2) 0.48549(15) 0.0279(7) Uani 1 1 d . . . . .
C4 C 0.7192(6) 0.7593(2) 0.48993(15) 0.0274(7) Uani 1 1 d . . . . .
H4 H 0.845042 0.756202 0.452110 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7337(6) 0.6880(2) 0.54907(15) 0.0258(7) Uani 1 1 d . . . . .
C6 C 0.5485(6) 0.6932(2) 0.60457(15) 0.0279(7) Uani 1 1 d . . . . .
H6 H 0.558046 0.645088 0.645375 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1479(6) 0.7766(2) 0.65899(15) 0.0263(7) Uani 1 1 d . . . . .
C8 C 0.1872(6) 0.7175(2) 0.72880(15) 0.0285(7) Uani 1 1 d . . . . .
H8 H 0.347447 0.676847 0.738677 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0021(6) 0.7198(2) 0.77991(16) 0.0288(7) Uani 1 1 d . . . . .
C10 C 0.0319(6) 0.6601(2) 0.85382(16) 0.0324(7) Uani 1 1 d . . . . .
C11 C 0.0668(7) 0.7178(2) 0.91522(17) 0.0375(8) Uani 1 1 d . . . . .
C12 C 0.1469(8) 0.6611(3) 0.98942(19) 0.0478(10) Uani 1 1 d . . . . .
C13 C 0.5134(6) 0.9128(2) 0.42390(16) 0.0296(7) Uani 1 1 d . . . . .
C14 C 0.6806(6) 0.9133(2) 0.36581(16) 0.0328(7) Uani 1 1 d . . . . .
H14 H 0.806687 0.860576 0.362581 0.039 Uiso 1 1 calc R U . . .
C15 C 0.6666(6) 0.9921(2) 0.31044(16) 0.0297(7) Uani 1 1 d . . . . .
C16 C 0.8476(6) 0.9874(2) 0.24326(16) 0.0314(7) Uani 1 1 d . . . . .
C17 C 0.6994(7) 0.9635(2) 0.17941(18) 0.0371(8) Uani 1 1 d . . . . .
C18 C 0.8601(7) 0.9509(3) 0.10991(18) 0.0434(9) Uani 1 1 d . . . . .
C19 C 0.9506(6) 0.6110(2) 0.55307(15) 0.0264(7) Uani 1 1 d . . . . .
C20 C 0.9800(6) 0.5357(2) 0.60758(16) 0.0295(7) Uani 1 1 d . . . . .
H20 H 0.848310 0.529262 0.643867 0.035 Uiso 1 1 calc R U . . .
C21 C 1.2043(6) 0.4674(2) 0.61040(15) 0.0289(7) Uani 1 1 d . . . . .
C22 C 1.2301(6) 0.3871(2) 0.67572(16) 0.0308(7) Uani 1 1 d . . . . .
C23 C 1.2928(6) 0.4217(2) 0.74687(16) 0.0318(7) Uani 1 1 d . . . . .
C24 C 1.3803(7) 0.3482(2) 0.81248(18) 0.0396(8) Uani 1 1 d . . . . .
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 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)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
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
C9 O2 H2A 109.5 . . ?
C13 O3 H3 109.5 . . ?
C19 O5 H5 109.5 . . ?
C6 C1 C2 119.8(3) . . ?
C6 C1 C7 122.1(3) . . ?
C2 C1 C7 118.1(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C13 121.0(3) . . ?
C2 C3 C13 119.4(3) . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 C19 119.1(3) . . ?
C6 C5 C19 121.6(3) . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C8 121.2(3) . . ?
O1 C7 C1 118.8(3) . . ?
C8 C7 C1 120.0(3) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O2 C9 C8 126.4(3) . . ?
O2 C9 C10 111.4(3) . . ?
C8 C9 C10 122.2(3) . . ?
F2 C10 F1 107.7(2) . . ?
F2 C10 C9 110.0(3) . . ?
F1 C10 C9 110.3(2) . . ?
F2 C10 C11 108.8(3) . . ?
F1 C10 C11 107.1(3) . . ?
C9 C10 C11 112.7(3) . . ?
F4 C11 F3 108.8(3) . . ?
F4 C11 C12 108.0(3) . . ?
F3 C11 C12 107.7(3) . . ?
F4 C11 C10 108.9(3) . . ?
F3 C11 C10 107.6(3) . . ?
C12 C11 C10 115.6(3) . . ?
F7 C12 F6 108.7(3) . . ?
F7 C12 F5 108.3(3) . . ?
F6 C12 F5 107.2(3) . . ?
F7 C12 C11 111.7(3) . . ?
F6 C12 C11 111.9(3) . . ?
F5 C12 C11 108.8(3) . . ?
O3 C13 C14 122.1(3) . . ?
O3 C13 C3 114.2(3) . . ?
C14 C13 C3 123.7(3) . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
O4 C15 C14 124.8(3) . . ?
O4 C15 C16 116.6(3) . . ?
C14 C15 C16 118.7(3) . . ?
F9 C16 F8 107.6(3) . . ?
F9 C16 C17 109.3(3) . . ?
F8 C16 C17 109.0(3) . . ?
F9 C16 C15 109.5(2) . . ?
F8 C16 C15 109.8(2) . . ?
C17 C16 C15 111.5(3) . . ?
F11 C17 F10 108.5(3) . . ?
F11 C17 C16 108.5(3) . . ?
F10 C17 C16 107.6(3) . . ?
F11 C17 C18 107.0(3) . . ?
F10 C17 C18 107.8(3) . . ?
C16 C17 C18 117.2(3) . . ?
F12 C18 F14 108.5(3) . . ?
F12 C18 F13 109.5(3) . . ?
F14 C18 F13 108.3(3) . . ?
F12 C18 C17 110.7(3) . . ?
F14 C18 C17 110.8(3) . . ?
F13 C18 C17 109.1(3) . . ?
O5 C19 C20 122.1(3) . . ?
O5 C19 C5 113.7(2) . . ?
C20 C19 C5 124.2(3) . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
O6 C21 C20 125.4(3) . . ?
O6 C21 C22 116.9(3) . . ?
C20 C21 C22 117.8(3) . . ?
F15 C22 F16 107.8(2) . . ?
F15 C22 C23 108.9(2) . . ?
F16 C22 C23 108.9(2) . . ?
F15 C22 C21 109.7(2) . . ?
F16 C22 C21 109.8(2) . . ?
C23 C22 C21 111.7(3) . . ?
F18 C23 F17 108.1(2) . . ?
F18 C23 C24 107.5(2) . . ?
F17 C23 C24 108.1(3) . . ?
F18 C23 C22 107.8(2) . . ?
F17 C23 C22 107.5(2) . . ?
C24 C23 C22 117.6(3) . . ?
F21 C24 F20 109.4(3) . . ?
F21 C24 F19 109.0(3) . . ?
F20 C24 F19 108.3(3) . . ?
F21 C24 C23 110.3(3) . . ?
F20 C24 C23 111.3(3) . . ?
F19 C24 C23 108.6(3) . . ?
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 C10 1.354(3) . ?
F2 C10 1.347(4) . ?
F3 C11 1.340(4) . ?
F4 C11 1.333(4) . ?
F5 C12 1.337(4) . ?
F6 C12 1.314(4) . ?
F7 C12 1.305(5) . ?
F8 C16 1.349(3) . ?
F9 C16 1.339(4) . ?
F10 C17 1.342(4) . ?
F11 C17 1.339(4) . ?
F12 C18 1.316(4) . ?
F13 C18 1.320(4) . ?
F14 C18 1.316(4) . ?
F15 C22 1.345(3) . ?
F16 C22 1.351(4) . ?
F17 C23 1.358(4) . ?
F18 C23 1.347(3) . ?
F19 C24 1.330(4) . ?
F20 C24 1.325(4) . ?
F21 C24 1.314(4) . ?
O1 C7 1.238(3) . ?
O2 C9 1.323(3) . ?
O2 H2A 0.8400 . ?
O3 C13 1.321(3) . ?
O3 H3 0.8400 . ?
O4 C15 1.230(3) . ?
O5 C19 1.327(3) . ?
O5 H5 0.8400 . ?
O6 C21 1.238(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.398(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 C13 1.484(4) . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(4) . ?
C5 C19 1.471(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.448(4) . ?
C8 C9 1.349(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.512(4) . ?
C10 C11 1.551(5) . ?
C11 C12 1.530(5) . ?
C13 C14 1.370(4) . ?
C14 C15 1.419(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.552(4) . ?
C16 C17 1.527(5) . ?
C17 C18 1.548(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.416(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.551(4) . ?
C22 C23 1.544(4) . ?
C23 C24 1.528(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O1 . . . 2.615(3) 0.840 1.913 140.3 no
O2 H2A O4 . . 2_576 2.885(3) 0.840 2.233 134.5 no
O3 H3 O1 . . 2_576 3.015(3) 0.840 2.414 129.1 no
O3 H3 O4 . . . 2.584(3) 0.840 1.854 144.5 no
O5 H5 O6 . . . 2.612(3) 0.840 1.875 145.7 no
O5 H5 O6 . . 2_866 3.005(3) 0.840 2.368 133.1 no
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
C6 C1 C2 C3 -0.7(5) . . . . ?
C7 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C1 C2 C3 C13 -177.3(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C13 C3 C4 C5 177.7(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C19 -177.6(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C7 C1 C6 C5 -179.7(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C19 C5 C6 C1 178.0(3) . . . . ?
C6 C1 C7 O1 -165.4(3) . . . . ?
C2 C1 C7 O1 15.0(4) . . . . ?
C6 C1 C7 C8 13.6(5) . . . . ?
C2 C1 C7 C8 -166.0(3) . . . . ?
O1 C7 C8 C9 3.8(5) . . . . ?
C1 C7 C8 C9 -175.1(3) . . . . ?
C7 C8 C9 O2 1.8(5) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
O2 C9 C10 F2 50.0(3) . . . . ?
C8 C9 C10 F2 -129.1(3) . . . . ?
O2 C9 C10 F1 168.8(3) . . . . ?
C8 C9 C10 F1 -10.3(4) . . . . ?
O2 C9 C10 C11 -71.6(3) . . . . ?
C8 C9 C10 C11 109.3(3) . . . . ?
F2 C10 C11 F4 -54.6(3) . . . . ?
F1 C10 C11 F4 -170.8(3) . . . . ?
C9 C10 C11 F4 67.7(4) . . . . ?
F2 C10 C11 F3 -172.4(2) . . . . ?
F1 C10 C11 F3 71.4(3) . . . . ?
C9 C10 C11 F3 -50.1(3) . . . . ?
F2 C10 C11 C12 67.2(4) . . . . ?
F1 C10 C11 C12 -49.0(4) . . . . ?
C9 C10 C11 C12 -170.5(3) . . . . ?
F4 C11 C12 F7 66.1(4) . . . . ?
F3 C11 C12 F7 -176.5(3) . . . . ?
C10 C11 C12 F7 -56.2(4) . . . . ?
F4 C11 C12 F6 -171.7(3) . . . . ?
F3 C11 C12 F6 -54.3(4) . . . . ?
C10 C11 C12 F6 66.0(4) . . . . ?
F4 C11 C12 F5 -53.4(4) . . . . ?
F3 C11 C12 F5 64.0(4) . . . . ?
C10 C11 C12 F5 -175.7(3) . . . . ?
C4 C3 C13 O3 -174.2(3) . . . . ?
C2 C3 C13 O3 4.2(4) . . . . ?
C4 C3 C13 C14 4.5(5) . . . . ?
C2 C3 C13 C14 -177.1(3) . . . . ?
O3 C13 C14 C15 1.4(5) . . . . ?
C3 C13 C14 C15 -177.2(3) . . . . ?
C13 C14 C15 O4 3.2(5) . . . . ?
C13 C14 C15 C16 -176.2(3) . . . . ?
O4 C15 C16 F9 39.6(4) . . . . ?
C14 C15 C16 F9 -140.9(3) . . . . ?
O4 C15 C16 F8 157.5(3) . . . . ?
C14 C15 C16 F8 -23.0(4) . . . . ?
O4 C15 C16 C17 -81.5(4) . . . . ?
C14 C15 C16 C17 98.0(3) . . . . ?
F9 C16 C17 F11 -59.1(3) . . . . ?
F8 C16 C17 F11 -176.4(2) . . . . ?
C15 C16 C17 F11 62.2(3) . . . . ?
F9 C16 C17 F10 -176.3(2) . . . . ?
F8 C16 C17 F10 66.4(3) . . . . ?
C15 C16 C17 F10 -55.0(3) . . . . ?
F9 C16 C17 C18 62.2(4) . . . . ?
F8 C16 C17 C18 -55.2(4) . . . . ?
C15 C16 C17 C18 -176.6(3) . . . . ?
F11 C17 C18 F12 61.9(4) . . . . ?
F10 C17 C18 F12 178.4(3) . . . . ?
C16 C17 C18 F12 -60.1(4) . . . . ?
F11 C17 C18 F14 -177.7(3) . . . . ?
F10 C17 C18 F14 -61.2(4) . . . . ?
C16 C17 C18 F14 60.3(4) . . . . ?
F11 C17 C18 F13 -58.6(4) . . . . ?
F10 C17 C18 F13 57.9(4) . . . . ?
C16 C17 C18 F13 179.4(3) . . . . ?
C4 C5 C19 O5 2.4(4) . . . . ?
C6 C5 C19 O5 -175.0(3) . . . . ?
C4 C5 C19 C20 -177.9(3) . . . . ?
C6 C5 C19 C20 4.7(5) . . . . ?
O5 C19 C20 C21 4.1(5) . . . . ?
C5 C19 C20 C21 -175.6(3) . . . . ?
C19 C20 C21 O6 -2.2(5) . . . . ?
C19 C20 C21 C22 177.0(3) . . . . ?
O6 C21 C22 F15 -12.0(4) . . . . ?
C20 C21 C22 F15 168.7(3) . . . . ?
O6 C21 C22 F16 -130.3(3) . . . . ?
C20 C21 C22 F16 50.4(4) . . . . ?
O6 C21 C22 C23 108.8(3) . . . . ?
C20 C21 C22 C23 -70.5(4) . . . . ?
F15 C22 C23 F18 -167.8(2) . . . . ?
F16 C22 C23 F18 -50.5(3) . . . . ?
C21 C22 C23 F18 70.8(3) . . . . ?
F15 C22 C23 F17 75.9(3) . . . . ?
F16 C22 C23 F17 -166.8(2) . . . . ?
C21 C22 C23 F17 -45.4(3) . . . . ?
F15 C22 C23 C24 -46.3(4) . . . . ?
F16 C22 C23 C24 71.0(3) . . . . ?
C21 C22 C23 C24 -167.6(3) . . . . ?
F18 C23 C24 F21 64.0(3) . . . . ?
F17 C23 C24 F21 -179.6(2) . . . . ?
C22 C23 C24 F21 -57.7(4) . . . . ?
F18 C23 C24 F20 -174.4(3) . . . . ?
F17 C23 C24 F20 -58.0(3) . . . . ?
C22 C23 C24 F20 63.8(4) . . . . ?
F18 C23 C24 F19 -55.4(4) . . . . ?
F17 C23 C24 F19 61.1(3) . . . . ?
C22 C23 C24 F19 -177.1(3) . . . . ?
