#------------------------------------------------------------------------------
#$Date: 2021-06-28 03:48:15 +0300 (Mon, 28 Jun 2021) $
#$Revision: 266727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/37/1563717.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_1563717
loop_
_publ_author_name
'Zhang, Yan'
'Ma, Chanchan'
'Struwe, Julia'
'Feng, Jian'
'Zhu, Gangguo'
'Ackermann, Lutz'
_publ_section_title
;
 Electrooxidative Dearomatization of Biaryls: Synthesis of Tri- and
 Difluoromethylated Spiro[5.5]trienones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02682H
_journal_year                    2021
_chemical_formula_moiety         'C22 H13 F3 O2'
_chemical_formula_sum            'C22 H13 F3 O2'
_chemical_formula_weight         366.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.508(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4761(8)
_cell_length_b                   10.1707(8)
_cell_length_c                   33.232(2)
_cell_measurement_reflns_used    9753
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.660
_cell_measurement_theta_min      2.354
_cell_volume                     3510.5(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture AgMo Dual Source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            54286
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.706
_diffrn_reflns_theta_min         2.096
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.8496
_exptl_absorpt_correction_T_min  0.7935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0766 before and 0.0411 after correction.
The Ratio of minimum to maximum transmission is 0.9340.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         9039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0583
_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)+(0.0526P)²+1.9986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7615
_reflns_number_total             9039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02682h2.cif
_cod_data_source_block           mo_1095_cg_0m
_cod_original_cell_volume        3510.4(4)
_cod_database_code               1563717
_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   0.976
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.21589(11) 0.40203(10) 0.35573(3) 0.0433(2) Uani 1 1 d . . . . .
F2 F 0.02182(10) 0.44958(10) 0.32909(3) 0.0410(2) Uani 1 1 d . . . . .
F3 F 0.15464(11) 0.60237(9) 0.35012(3) 0.0420(2) Uani 1 1 d . . . . .
O1 O 0.13335(14) 0.26306(11) 0.28552(4) 0.0432(3) Uani 1 1 d . . . . .
O2 O 0.47411(16) 0.90263(14) 0.18575(4) 0.0564(4) Uani 1 1 d . . . . .
C1 C 0.14578(15) 0.48678(15) 0.33108(4) 0.0301(3) Uani 1 1 d . . . . .
C2 C 0.18708(13) 0.48862(14) 0.28891(4) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.23330(13) 0.59510(13) 0.27177(4) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.27044(13) 0.59102(14) 0.22839(4) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.23171(14) 0.46393(15) 0.20544(4) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.19180(14) 0.35364(14) 0.22509(4) 0.0288(3) Uani 1 1 d . . . . .
C7 C 0.16957(15) 0.35926(14) 0.26802(4) 0.0287(3) Uani 1 1 d . . . . .
C8 C 0.16427(17) 0.23561(16) 0.20377(5) 0.0385(4) Uani 1 1 d . . . . .
H8 H 0.139730 0.159816 0.217606 0.046 Uiso 1 1 calc R U . . .
C9 C 0.17289(19) 0.22978(19) 0.16273(6) 0.0469(5) Uani 1 1 d . . . . .
H9 H 0.153439 0.150342 0.148168 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2100(2) 0.34021(19) 0.14288(5) 0.0467(4) Uani 1 1 d . . . . .
H10 H 0.214478 0.336480 0.114536 0.056 Uiso 1 1 calc R U . . .
C11 C 0.24078(17) 0.45655(18) 0.16388(5) 0.0387(4) Uani 1 1 d . . . . .
H11 H 0.267992 0.531056 0.150004 0.046 Uiso 1 1 calc R U . . .
C12 C 0.20709(15) 0.70520(15) 0.20445(4) 0.0307(3) Uani 1 1 d . . . . .
H12 H 0.115727 0.708063 0.199668 0.037 Uiso 1 1 calc R U . . .
C13 C 0.27304(18) 0.80207(16) 0.18971(5) 0.0374(4) Uani 1 1 d . . . . .
H13 H 0.227258 0.869438 0.174132 0.045 Uiso 1 1 calc R U . . .
C14 C 0.41439(18) 0.80794(16) 0.19679(5) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.48042(16) 0.69668(17) 0.21798(5) 0.0354(3) Uani 1 1 d . . . . .
H15 H 0.571841 0.694084 0.221242 0.042 Uiso 1 1 calc R U . . .
C16 C 0.41653(14) 0.59851(15) 0.23291(4) 0.0301(3) Uani 1 1 d . . . . .
H16 H 0.464720 0.529813 0.247073 0.036 Uiso 1 1 calc R U . . .
C17 C 0.25794(15) 0.72509(14) 0.29248(4) 0.0276(3) Uani 1 1 d . . . . .
C18 C 0.16463(18) 0.82273(16) 0.28714(5) 0.0381(4) Uani 1 1 d . . . . .
H18 H 0.084922 0.806325 0.270769 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1877(2) 0.94466(18) 0.30575(6) 0.0520(5) Uani 1 1 d . . . . .
H19 H 0.123667 1.011326 0.302141 0.062 Uiso 1 1 calc R U . . .
C20 C 0.3036(3) 0.9684(2) 0.32942(7) 0.0593(6) Uani 1 1 d . . . . .
H20 H 0.319204 1.051663 0.342088 0.071 Uiso 1 1 calc R U . . .
C21 C 0.3965(2) 0.8727(2) 0.33479(6) 0.0585(6) Uani 1 1 d . . . . .
H21 H 0.476118 0.890084 0.351111 0.070 Uiso 1 1 calc R U . . .
C22 C 0.37483(17) 0.74935(19) 0.31638(5) 0.0406(4) Uani 1 1 d . . . . .
H22 H 0.439163 0.683054 0.320170 0.049 Uiso 1 1 calc R U . . .
F4 F 0.60971(12) 0.82296(12) 0.59286(3) 0.0569(3) Uani 1 1 d . . . . .
F5 F 0.41658(13) 0.85918(15) 0.60040(4) 0.0651(4) Uani 1 1 d . . . . .
F6 F 0.52131(13) 1.00475(11) 0.57111(4) 0.0562(3) Uani 1 1 d . . . . .
O3 O 0.66614(12) 0.87075(15) 0.51670(4) 0.0498(3) Uani 1 1 d . . . . .
O4 O -0.06044(12) 0.60254(16) 0.42532(5) 0.0560(4) Uani 1 1 d . . . . .
C23 C 0.50044(18) 0.87590(18) 0.57422(5) 0.0409(4) Uani 1 1 d . . . . .
C24 C 0.46136(15) 0.81206(14) 0.53319(4) 0.0300(3) Uani 1 1 d . . . . .
C25 C 0.34127(14) 0.77073(13) 0.51995(4) 0.0266(3) Uani 1 1 d . . . . .
C26 C 0.31046(13) 0.69725(13) 0.47939(4) 0.0235(3) Uani 1 1 d . . . . .
C27 C 0.42920(13) 0.66232(14) 0.45932(4) 0.0246(3) Uani 1 1 d . . . . .
C28 C 0.54831(14) 0.72103(14) 0.47155(4) 0.0272(3) Uani 1 1 d . . . . .
C29 C 0.56778(15) 0.80602(15) 0.50771(5) 0.0315(3) Uani 1 1 d . . . . .
C30 C 0.65168(15) 0.69677(16) 0.44970(5) 0.0336(3) Uani 1 1 d . . . . .
H30 H 0.732343 0.738253 0.457540 0.040 Uiso 1 1 calc R U . . .
C31 C 0.63642(16) 0.61280(17) 0.41685(5) 0.0359(4) Uani 1 1 d . . . . .
H31 H 0.706705 0.596684 0.402130 0.043 Uiso 1 1 calc R U . . .
C32 C 0.51852(16) 0.55145(17) 0.40513(5) 0.0363(4) Uani 1 1 d . . . . .
H32 H 0.508951 0.492471 0.382769 0.044 Uiso 1 1 calc R U . . .
C33 C 0.41513(15) 0.57658(16) 0.42615(4) 0.0320(3) Uani 1 1 d . . . . .
H33 H 0.334510 0.535417 0.417974 0.038 Uiso 1 1 calc R U . . .
C34 C 0.24228(14) 0.57097(14) 0.48727(4) 0.0266(3) Uani 1 1 d . . . . .
H34 H 0.285160 0.510726 0.506288 0.032 Uiso 1 1 calc R U . . .
C35 C 0.12514(15) 0.53898(16) 0.46906(4) 0.0312(3) Uani 1 1 d . . . . .
H35 H 0.089326 0.456328 0.474799 0.037 Uiso 1 1 calc R U . . .
C36 C 0.05026(14) 0.62873(17) 0.44031(5) 0.0346(3) Uani 1 1 d . . . . .
C37 C 0.11290(14) 0.75166(15) 0.43083(5) 0.0308(3) Uani 1 1 d . . . . .
H37 H 0.069592 0.808883 0.410955 0.037 Uiso 1 1 calc R U . . .
C38 C 0.22905(14) 0.78555(14) 0.44931(4) 0.0273(3) Uani 1 1 d . . . . .
H38 H 0.262538 0.869104 0.443359 0.033 Uiso 1 1 calc R U . . .
C39 C 0.22587(15) 0.79899(15) 0.54078(4) 0.0312(3) Uani 1 1 d . . . . .
C40 C 0.17439(17) 0.70770(17) 0.56494(5) 0.0371(4) Uani 1 1 d . . . . .
H40 H 0.214132 0.624074 0.569382 0.044 Uiso 1 1 calc R U . . .
C41 C 0.06501(18) 0.7371(2) 0.58281(5) 0.0455(4) Uani 1 1 d . . . . .
H41 H 0.031934 0.674543 0.599986 0.055 Uiso 1 1 calc R U . . .
C42 C 0.0049(2) 0.8557(3) 0.57574(7) 0.0650(7) Uani 1 1 d . . . . .
H42 H -0.071598 0.874690 0.587124 0.078 Uiso 1 1 calc R U . . .
C43 C 0.0567(3) 0.9476(3) 0.55187(9) 0.0861(10) Uani 1 1 d . . . . .
H43 H 0.015998 1.030684 0.547217 0.103 Uiso 1 1 calc R U . . .
C44 C 0.1676(3) 0.9199(2) 0.53455(7) 0.0621(6) Uani 1 1 d . . . . .
H44 H 0.202991 0.984196 0.518485 0.075 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'
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
F1 C1 F2 107.30(12) . . ?
F1 C1 C2 111.86(13) . . ?
F2 C1 C2 110.32(12) . . ?
F3 C1 F1 106.17(12) . . ?
F3 C1 F2 106.16(13) . . ?
F3 C1 C2 114.61(12) . . ?
C3 C2 C1 124.25(13) . . ?
C3 C2 C7 123.00(12) . . ?
C7 C2 C1 112.75(12) . . ?
C2 C3 C4 121.58(12) . . ?
C2 C3 C17 124.55(12) . . ?
C17 C3 C4 113.84(11) . . ?
C5 C4 C3 113.97(11) . . ?
C12 C4 C3 108.93(11) . . ?
C12 C4 C5 108.51(12) . . ?
C12 C4 C16 112.37(12) . . ?
C16 C4 C3 106.27(11) . . ?
C16 C4 C5 106.85(11) . . ?
C6 C5 C4 121.66(12) . . ?
C6 C5 C11 118.95(14) . . ?
C11 C5 C4 119.35(13) . . ?
C5 C6 C7 121.19(13) . . ?
C5 C6 C8 120.51(14) . . ?
C8 C6 C7 118.20(14) . . ?
O1 C7 C2 120.82(13) . . ?
O1 C7 C6 121.75(13) . . ?
C6 C7 C2 117.37(12) . . ?
C6 C8 H8 120.0 . . ?
C9 C8 C6 119.97(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.67(15) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.86(16) . . ?
C11 C10 H10 119.6 . . ?
C5 C11 H11 120.0 . . ?
C10 C11 C5 120.01(16) . . ?
C10 C11 H11 120.0 . . ?
C4 C12 H12 118.4 . . ?
C13 C12 C4 123.26(15) . . ?
C13 C12 H12 118.4 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.06(15) . . ?
C14 C13 H13 119.0 . . ?
O2 C14 C13 121.66(18) . . ?
O2 C14 C15 121.58(18) . . ?
C15 C14 C13 116.75(14) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.08(15) . . ?
C16 C15 H15 119.0 . . ?
C4 C16 H16 118.4 . . ?
C15 C16 C4 123.28(15) . . ?
C15 C16 H16 118.4 . . ?
C18 C17 C3 119.78(14) . . ?
C18 C17 C22 119.89(15) . . ?
C22 C17 C3 120.32(14) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.13(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.44(17) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.45(19) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.24(19) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
F4 C23 C24 110.92(14) . . ?
F5 C23 F4 104.13(15) . . ?
F5 C23 F6 107.82(15) . . ?
F5 C23 C24 114.25(15) . . ?
F6 C23 F4 106.94(15) . . ?
F6 C23 C24 112.22(15) . . ?
C25 C24 C23 123.97(14) . . ?
C25 C24 C29 122.68(13) . . ?
C29 C24 C23 113.26(14) . . ?
C24 C25 C26 121.25(12) . . ?
C24 C25 C39 124.47(13) . . ?
C39 C25 C26 114.13(12) . . ?
C27 C26 C25 113.94(11) . . ?
C34 C26 C25 108.14(11) . . ?
C34 C26 C27 107.98(11) . . ?
C34 C26 C38 112.29(12) . . ?
C38 C26 C25 108.95(11) . . ?
C38 C26 C27 105.62(11) . . ?
C28 C27 C26 121.44(12) . . ?
C28 C27 C33 119.64(13) . . ?
C33 C27 C26 118.76(13) . . ?
C27 C28 C29 120.80(13) . . ?
C27 C28 C30 119.72(14) . . ?
C30 C28 C29 119.46(14) . . ?
O3 C29 C24 120.53(15) . . ?
O3 C29 C28 122.42(15) . . ?
C28 C29 C24 117.04(13) . . ?
C28 C30 H30 120.0 . . ?
C31 C30 C28 120.10(15) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C30 C31 C32 120.38(14) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 119.91(15) . . ?
C33 C32 H32 120.0 . . ?
C27 C33 H33 119.9 . . ?
C32 C33 C27 120.21(15) . . ?
C32 C33 H33 119.9 . . ?
C26 C34 H34 118.1 . . ?
C35 C34 C26 123.81(13) . . ?
C35 C34 H34 118.1 . . ?
C34 C35 H35 119.2 . . ?
C34 C35 C36 121.56(14) . . ?
C36 C35 H35 119.2 . . ?
O4 C36 C35 121.54(16) . . ?
O4 C36 C37 121.51(16) . . ?
C37 C36 C35 116.94(13) . . ?
C36 C37 H37 119.0 . . ?
C38 C37 C36 121.90(14) . . ?
C38 C37 H37 119.0 . . ?
C26 C38 H38 118.3 . . ?
C37 C38 C26 123.33(13) . . ?
C37 C38 H38 118.3 . . ?
C40 C39 C25 122.65(14) . . ?
C44 C39 C25 118.10(15) . . ?
C44 C39 C40 119.22(16) . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.63(16) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 119.9 . . ?
C42 C41 C40 120.23(19) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 120.4 . . ?
C41 C42 C43 119.29(18) . . ?
C43 C42 H42 120.4 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(2) . . ?
C44 C43 H43 119.6 . . ?
C39 C44 C43 119.8(2) . . ?
C39 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
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 1.3404(18) . ?
F2 C1 1.3460(18) . ?
F3 C1 1.3325(17) . ?
O1 C7 1.2237(18) . ?
O2 C14 1.230(2) . ?
C1 C2 1.5198(19) . ?
C2 C3 1.3431(19) . ?
C2 C7 1.4877(19) . ?
C3 C4 1.5418(18) . ?
C3 C17 1.4973(19) . ?
C4 C5 1.5285(19) . ?
C4 C12 1.511(2) . ?
C4 C16 1.520(2) . ?
C5 C6 1.389(2) . ?
C5 C11 1.399(2) . ?
C6 C7 1.476(2) . ?
C6 C8 1.404(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.333(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.470(3) . ?
C14 C15 1.459(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.333(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 C22 1.392(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.401(3) . ?
C22 H22 0.9500 . ?
F4 C23 1.341(2) . ?
F5 C23 1.326(2) . ?
F6 C23 1.335(2) . ?
O3 C29 1.226(2) . ?
O4 C36 1.230(2) . ?
C23 C24 1.517(2) . ?
C24 C25 1.345(2) . ?
C24 C29 1.487(2) . ?
C25 C26 1.5381(19) . ?
C25 C39 1.497(2) . ?
C26 C27 1.5280(18) . ?
C26 C34 1.5091(19) . ?
C26 C38 1.5200(19) . ?
C27 C28 1.395(2) . ?
C27 C33 1.398(2) . ?
C28 C29 1.473(2) . ?
C28 C30 1.402(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.393(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.387(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.336(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.472(2) . ?
C36 C37 1.465(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.335(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.382(2) . ?
C39 C44 1.376(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.390(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.366(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.382(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.391(3) . ?
C44 H44 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
F1 C1 C2 C3 -118.77(15) . . . . ?
F1 C1 C2 C7 61.90(16) . . . . ?
F2 C1 C2 C3 121.88(15) . . . . ?
F2 C1 C2 C7 -57.45(16) . . . . ?
F3 C1 C2 C3 2.1(2) . . . . ?
F3 C1 C2 C7 -177.19(13) . . . . ?
O2 C14 C15 C16 174.57(15) . . . . ?
C1 C2 C3 C4 -178.51(13) . . . . ?
C1 C2 C3 C17 3.7(2) . . . . ?
C1 C2 C7 O1 -4.4(2) . . . . ?
C1 C2 C7 C6 172.85(13) . . . . ?
C2 C3 C4 C5 8.43(19) . . . . ?
C2 C3 C4 C12 129.74(14) . . . . ?
C2 C3 C4 C16 -108.98(15) . . . . ?
C2 C3 C17 C18 -95.02(18) . . . . ?
C2 C3 C17 C22 86.26(19) . . . . ?
C3 C2 C7 O1 176.24(15) . . . . ?
C3 C2 C7 C6 -6.5(2) . . . . ?
C3 C4 C5 C6 -12.6(2) . . . . ?
C3 C4 C5 C11 169.61(14) . . . . ?
C3 C4 C12 C13 116.43(15) . . . . ?
C3 C4 C16 C15 -117.79(15) . . . . ?
C3 C17 C18 C19 -178.91(15) . . . . ?
C3 C17 C22 C21 178.75(15) . . . . ?
C4 C3 C17 C18 87.01(16) . . . . ?
C4 C3 C17 C22 -91.71(16) . . . . ?
C4 C5 C6 C7 7.7(2) . . . . ?
C4 C5 C6 C8 -176.09(14) . . . . ?
C4 C5 C11 C10 177.86(16) . . . . ?
C4 C12 C13 C14 -2.1(2) . . . . ?
C5 C4 C12 C13 -118.98(16) . . . . ?
C5 C4 C16 C15 120.16(16) . . . . ?
C5 C6 C7 O1 179.36(15) . . . . ?
C5 C6 C7 C2 2.1(2) . . . . ?
C5 C6 C8 C9 -2.0(3) . . . . ?
C6 C5 C11 C10 0.1(3) . . . . ?
C6 C8 C9 C10 0.7(3) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C7 C2 C3 C17 -177.07(13) . . . . ?
C7 C6 C8 C9 174.30(16) . . . . ?
C8 C6 C7 O1 3.0(2) . . . . ?
C8 C6 C7 C2 -174.20(14) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C5 -1.4(3) . . . . ?
C11 C5 C6 C7 -174.57(15) . . . . ?
C11 C5 C6 C8 1.7(2) . . . . ?
C12 C4 C5 C6 -134.20(14) . . . . ?
C12 C4 C5 C11 48.06(18) . . . . ?
C12 C4 C16 C15 1.3(2) . . . . ?
C12 C13 C14 O2 -174.37(16) . . . . ?
C12 C13 C14 C15 4.9(2) . . . . ?
C13 C14 C15 C16 -4.7(2) . . . . ?
C14 C15 C16 C4 1.7(2) . . . . ?
C16 C4 C5 C6 104.42(15) . . . . ?
C16 C4 C5 C11 -73.32(17) . . . . ?
C16 C4 C12 C13 -1.1(2) . . . . ?
C17 C3 C4 C5 -173.53(12) . . . . ?
C17 C3 C4 C12 -52.22(16) . . . . ?
C17 C3 C4 C16 69.06(15) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C17 C22 C21 0.0(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
F4 C23 C24 C25 133.34(16) . . . . ?
F4 C23 C24 C29 -49.89(19) . . . . ?
F5 C23 C24 C25 16.0(2) . . . . ?
F5 C23 C24 C29 -167.20(15) . . . . ?
F6 C23 C24 C25 -107.11(19) . . . . ?
F6 C23 C24 C29 69.66(19) . . . . ?
O4 C36 C37 C38 174.72(17) . . . . ?
C23 C24 C25 C26 -175.26(14) . . . . ?
C23 C24 C25 C39 9.3(2) . . . . ?
C23 C24 C29 O3 -13.8(2) . . . . ?
C23 C24 C29 C28 166.97(13) . . . . ?
C24 C25 C26 C27 7.17(19) . . . . ?
C24 C25 C26 C34 127.23(14) . . . . ?
C24 C25 C26 C38 -110.46(15) . . . . ?
C24 C25 C39 C40 -101.1(2) . . . . ?
C24 C25 C39 C44 80.6(2) . . . . ?
C25 C24 C29 O3 163.06(16) . . . . ?
C25 C24 C29 C28 -16.2(2) . . . . ?
C25 C26 C27 C28 -15.31(18) . . . . ?
C25 C26 C27 C33 169.25(12) . . . . ?
C25 C26 C34 C35 121.91(15) . . . . ?
C25 C26 C38 C37 -122.50(15) . . . . ?
C25 C39 C40 C41 -178.25(16) . . . . ?
C25 C39 C44 C43 177.0(2) . . . . ?
C26 C25 C39 C40 83.19(18) . . . . ?
C26 C25 C39 C44 -95.1(2) . . . . ?
C26 C27 C28 C29 8.0(2) . . . . ?
C26 C27 C28 C30 -173.42(12) . . . . ?
C26 C27 C33 C32 174.61(13) . . . . ?
C26 C34 C35 C36 -2.2(2) . . . . ?
C27 C26 C34 C35 -114.36(15) . . . . ?
C27 C26 C38 C37 114.72(15) . . . . ?
C27 C28 C29 O3 -171.59(15) . . . . ?
C27 C28 C29 C24 7.7(2) . . . . ?
C27 C28 C30 C31 -1.5(2) . . . . ?
C28 C27 C33 C32 -0.9(2) . . . . ?
C28 C30 C31 C32 0.0(2) . . . . ?
C29 C24 C25 C26 8.3(2) . . . . ?
C29 C24 C25 C39 -167.13(14) . . . . ?
C29 C28 C30 C31 177.13(13) . . . . ?
C30 C28 C29 O3 9.8(2) . . . . ?
C30 C28 C29 C24 -170.97(13) . . . . ?
C30 C31 C32 C33 1.1(2) . . . . ?
C31 C32 C33 C27 -0.6(2) . . . . ?
C33 C27 C28 C29 -176.64(13) . . . . ?
C33 C27 C28 C30 2.0(2) . . . . ?
C34 C26 C27 C28 -135.46(13) . . . . ?
C34 C26 C27 C33 49.10(16) . . . . ?
C34 C26 C38 C37 -2.73(19) . . . . ?
C34 C35 C36 O4 -175.79(16) . . . . ?
C34 C35 C36 C37 3.3(2) . . . . ?
C35 C36 C37 C38 -4.4(2) . . . . ?
C36 C37 C38 C26 4.3(2) . . . . ?
C38 C26 C27 C28 104.22(14) . . . . ?
C38 C26 C27 C33 -71.22(16) . . . . ?
C38 C26 C34 C35 1.67(19) . . . . ?
C39 C25 C26 C27 -176.99(12) . . . . ?
C39 C25 C26 C34 -56.93(15) . . . . ?
C39 C25 C26 C38 65.38(15) . . . . ?
C39 C40 C41 C42 1.8(3) . . . . ?
C40 C39 C44 C43 -1.3(4) . . . . ?
C40 C41 C42 C43 -2.3(4) . . . . ?
C41 C42 C43 C44 1.0(5) . . . . ?
C42 C43 C44 C39 0.8(5) . . . . ?
C44 C39 C40 C41 0.0(3) . . . . ?
