#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/81/7118112.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_7118112
loop_
_publ_author_name
'Can Xue'
'Xin Huang'
'Shangze Wu'
'Jing Zhou'
'Jianxin Dai'
'Chunling Fu'
'Shengming Ma'
_publ_section_title
;
 TfOH-catalyzed domino cycloisomerization/hydrolytic defluorination of
 2,3-allenyl perfluoroalkyl ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              17112
_journal_paper_doi               10.1039/C5cc06111C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C23 H17 F7 O2'
_chemical_formula_weight         458.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-13 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                108.215(10)
_cell_angle_beta                 105.015(10)
_cell_angle_gamma                110.595(7)
_cell_formula_units_Z            4
_cell_length_a                   13.635(4)
_cell_length_b                   13.766(4)
_cell_length_c                   14.405(7)
_cell_measurement_temperature    296(2)
_cell_volume                     2187.4(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22702
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_correction_T_min  0.9340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7576
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1732
_refine_ls_R_factor_gt           0.1199
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1080P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2977
_refine_ls_wR_factor_ref         0.3230
_reflns_number_gt                3825
_reflns_number_total             7576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06111c2.cif
_cod_data_source_block           z
_cod_original_cell_volume        2187.5(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118112
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.4366(4) 0.5580(4) 0.1608(4) 0.1223(18) Uani 1 1 d . . .
O4 O 1.1709(3) 0.4641(3) -0.0464(3) 0.0742(10) Uani 1 1 d . . .
F8 F 1.3545(3) 0.5284(4) -0.0942(3) 0.1162(13) Uani 1 1 d D . .
F9 F 1.5235(3) 0.6245(4) 0.0356(4) 0.1324(16) Uani 1 1 d D . .
F10 F 1.3063(5) 0.6977(5) 0.0180(7) 0.207(3) Uani 1 1 d D . .
F11 F 1.4752(8) 0.7829(5) 0.1461(5) 0.221(4) Uani 1 1 d D . .
F12 F 1.4501(5) 0.8752(5) 0.0052(6) 0.188(3) Uani 1 1 d D . .
F13 F 1.5714(8) 0.8230(9) 0.0261(13) 0.359(9) Uani 1 1 d DU . .
F14 F 1.4230(13) 0.7265(7) -0.1105(6) 0.367(9) Uani 1 1 d DU . .
C24 C 1.2453(5) 0.4688(5) 0.0411(4) 0.0741(14) Uani 1 1 d . . .
C25 C 1.1835(5) 0.3963(5) 0.0768(4) 0.0723(14) Uani 1 1 d . . .
C26 C 1.0672(4) 0.3445(4) 0.0067(4) 0.0644(13) Uani 1 1 d . . .
C27 C 1.0630(4) 0.3897(4) -0.0658(4) 0.0651(13) Uani 1 1 d . . .
C28 C 0.9708(4) 0.3774(4) -0.1559(4) 0.0646(13) Uani 1 1 d . . .
C29 C 0.9941(5) 0.4106(6) -0.2308(4) 0.0863(17) Uani 1 1 d . . .
H29 H 1.0691 0.4396 -0.2257 0.104 Uiso 1 1 calc R . .
C30 C 0.9080(7) 0.4018(7) -0.3145(5) 0.102(2) Uani 1 1 d . . .
H30 H 0.9253 0.4247 -0.3651 0.123 Uiso 1 1 calc R . .
C31 C 0.7982(6) 0.3597(6) -0.3223(5) 0.096(2) Uani 1 1 d . . .
H31 H 0.7403 0.3546 -0.3778 0.116 Uiso 1 1 calc R . .
C32 C 0.7732(5) 0.3250(6) -0.2488(5) 0.0921(18) Uani 1 1 d . . .
H32 H 0.6977 0.2945 -0.2553 0.110 Uiso 1 1 calc R . .
C33 C 0.8585(5) 0.3348(5) -0.1648(4) 0.0808(16) Uani 1 1 d . . .
H33 H 0.8409 0.3127 -0.1140 0.097 Uiso 1 1 calc R . .
C34 C 0.9691(5) 0.2537(5) 0.0060(4) 0.0700(14) Uani 1 1 d . . .
C35 C 0.9043(6) 0.1465(6) -0.0843(6) 0.107(2) Uani 1 1 d . . .
H35 H 0.9232 0.1334 -0.1430 0.128 Uiso 1 1 calc R . .
C36 C 0.8151(8) 0.0627(8) -0.0865(10) 0.150(4) Uani 1 1 d . . .
H36 H 0.7723 -0.0088 -0.1470 0.180 Uiso 1 1 calc R . .
C37 C 0.7854(9) 0.0808(11) 0.0002(13) 0.160(5) Uani 1 1 d . . .
H37 H 0.7230 0.0214 -0.0026 0.192 Uiso 1 1 calc R . .
C38 C 0.8468(8) 0.1844(11) 0.0889(8) 0.126(3) Uani 1 1 d . . .
H38 H 0.8272 0.1968 0.1472 0.151 Uiso 1 1 calc R . .
C39 C 0.9384(6) 0.2706(7) 0.0913(5) 0.0956(19) Uani 1 1 d . . .
H39 H 0.9808 0.3421 0.1518 0.115 Uiso 1 1 calc R . .
C40 C 1.2321(6) 0.3762(6) 0.1709(4) 0.0865(17) Uani 1 1 d . . .
H40A H 1.1730 0.3490 0.1959 0.104 Uiso 1 1 calc R . .
H40B H 1.2951 0.4490 0.2290 0.104 Uiso 1 1 calc R . .
C41 C 1.2758(7) 0.2870(7) 0.1423(5) 0.112(2) Uani 1 1 d . . .
H41A H 1.2130 0.2139 0.0844 0.134 Uiso 1 1 calc R . .
H41B H 1.3352 0.3140 0.1176 0.134 Uiso 1 1 calc R . .
C42 C 1.3240(7) 0.2683(7) 0.2378(6) 0.130(3) Uani 1 1 d . . .
H42A H 1.3520 0.2134 0.2183 0.194 Uiso 1 1 calc R . .
H42B H 1.2646 0.2390 0.2609 0.194 Uiso 1 1 calc R . .
H42C H 1.3861 0.3406 0.2953 0.194 Uiso 1 1 calc R . .
C43 C 1.3659(6) 0.5413(5) 0.0785(5) 0.0929(18) Uani 1 1 d . . .
C44 C 1.4123(5) 0.5994(6) 0.0108(6) 0.104(2) Uani 1 1 d D . .
C45 C 1.4098(6) 0.7141(6) 0.0412(7) 0.139(3) Uani 1 1 d D . .
C46 C 1.4638(8) 0.7852(7) -0.0106(7) 0.147(3) Uani 1 1 d DU . .
O1 O 0.9704(3) 0.7795(4) 0.4386(3) 0.0863(11) Uani 1 1 d . . .
O2 O 1.0406(5) 0.6797(6) 0.6312(5) 0.148(2) Uani 1 1 d . . .
F1 F 0.8491(5) 0.4824(4) 0.4853(5) 0.170(2) Uani 1 1 d D . .
F2 F 0.8404(4) 0.5484(4) 0.3687(3) 0.1470(19) Uani 1 1 d DU . .
F3 F 0.7962(5) 0.7118(5) 0.5087(7) 0.196(3) Uani 1 1 d DU . .
F4 F 0.8132(7) 0.6296(8) 0.6084(5) 0.240(4) Uani 1 1 d DU . .
F5 F 0.6250(7) 0.4680(15) 0.3370(8) 0.410(11) Uani 1 1 d DU . .
F6 F 0.6403(7) 0.4348(9) 0.4641(13) 0.347(8) Uani 1 1 d D . .
F7 F 0.5861(6) 0.5524(8) 0.4561(8) 0.272(5) Uani 1 1 d DU . .
C1 C 1.0409(5) 0.7783(6) 0.5260(5) 0.0886(18) Uani 1 1 d . . .
C2 C 1.1494(5) 0.8658(6) 0.5665(4) 0.0855(17) Uani 1 1 d . . .
C3 C 1.1490(4) 0.9210(5) 0.4991(4) 0.0710(14) Uani 1 1 d . . .
C4 C 1.0395(4) 0.8688(5) 0.4248(4) 0.0692(13) Uani 1 1 d . . .
C5 C 0.9797(4) 0.8864(5) 0.3373(4) 0.0673(13) Uani 1 1 d . . .
C6 C 0.8754(5) 0.8003(5) 0.2557(4) 0.0791(15) Uani 1 1 d . . .
H6 H 0.8417 0.7291 0.2566 0.095 Uiso 1 1 calc R . .
C7 C 0.8203(6) 0.8173(7) 0.1731(5) 0.0955(19) Uani 1 1 d . . .
H7 H 0.7505 0.7575 0.1178 0.115 Uiso 1 1 calc R . .
C8 C 0.8681(6) 0.9229(7) 0.1716(5) 0.097(2) Uani 1 1 d . . .
H8 H 0.8303 0.9347 0.1157 0.116 Uiso 1 1 calc R . .
C9 C 0.9704(6) 1.0096(6) 0.2519(5) 0.0967(19) Uani 1 1 d . . .
H9 H 1.0024 1.0807 0.2505 0.116 Uiso 1 1 calc R . .
C10 C 1.0278(5) 0.9939(5) 0.3357(4) 0.0811(16) Uani 1 1 d . . .
H10 H 1.0977 1.0541 0.3905 0.097 Uiso 1 1 calc R . .
C11 C 1.2499(5) 1.0131(5) 0.5057(4) 0.0761(15) Uani 1 1 d . . .
C12 C 1.2883(7) 0.9895(7) 0.4259(7) 0.119(2) Uani 1 1 d . . .
H12 H 1.2482 0.9150 0.3696 0.142 Uiso 1 1 calc R . .
C13 C 1.3825(9) 1.0698(11) 0.4247(11) 0.165(4) Uani 1 1 d . . .
H13 H 1.4052 1.0509 0.3689 0.198 Uiso 1 1 calc R . .
C14 C 1.4403(9) 1.1770(12) 0.5075(12) 0.164(4) Uani 1 1 d . . .
H14 H 1.5050 1.2324 0.5092 0.197 Uiso 1 1 calc R . .
C15 C 1.4059(8) 1.2074(8) 0.5912(9) 0.142(4) Uani 1 1 d . . .
H15 H 1.4464 1.2824 0.6468 0.171 Uiso 1 1 calc R . .
C16 C 1.3098(6) 1.1236(6) 0.5902(5) 0.106(2) Uani 1 1 d . . .
H16 H 1.2865 1.1421 0.6457 0.127 Uiso 1 1 calc R . .
C17 C 1.2527(6) 0.8959(7) 0.6626(5) 0.105(2) Uani 1 1 d . . .
H17A H 1.3007 0.9795 0.6998 0.126 Uiso 1 1 calc R . .
H17B H 1.2263 0.8715 0.7118 0.126 Uiso 1 1 calc R . .
C18 C 1.3237(6) 0.8404(7) 0.6326(6) 0.112(2) Uani 1 1 d . . .
H18A H 1.3490 0.8631 0.5822 0.134 Uiso 1 1 calc R . .
H18B H 1.2772 0.7567 0.5979 0.134 Uiso 1 1 calc R . .
C19 C 1.4287(7) 0.8770(9) 0.7325(7) 0.148(3) Uani 1 1 d . . .
H19A H 1.4727 0.8399 0.7119 0.223 Uiso 1 1 calc R . .
H19B H 1.4035 0.8543 0.7823 0.223 Uiso 1 1 calc R . .
H19C H 1.4757 0.9596 0.7658 0.223 Uiso 1 1 calc R . .
C20 C 0.9894(7) 0.6878(8) 0.5555(7) 0.125(3) Uani 1 1 d U . .
C21 C 0.8621(8) 0.5747(7) 0.4698(6) 0.134(3) Uani 1 1 d DU . .
C22 C 0.7837(9) 0.6145(8) 0.5054(7) 0.166(4) Uani 1 1 d DU . .
C23 C 0.6582(10) 0.5177(10) 0.4379(9) 0.205(5) Uani 1 1 d DU . .
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'
O O 0.0106 0.0060 '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'
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
C27 O4 C24 107.3(4) . .
O4 C24 C25 109.4(5) . .
O4 C24 C43 118.8(5) . .
C25 C24 C43 131.9(5) . .
C24 C25 C26 106.4(4) . .
C24 C25 C40 126.6(5) . .
C26 C25 C40 127.0(5) . .
C27 C26 C25 106.8(5) . .
C27 C26 C34 126.3(5) . .
C25 C26 C34 126.9(5) . .
O4 C27 C26 110.2(4) . .
O4 C27 C28 114.6(4) . .
C26 C27 C28 135.3(5) . .
C29 C28 C33 118.5(5) . .
C29 C28 C27 120.9(5) . .
C33 C28 C27 120.6(5) . .
C28 C29 C30 121.1(6) . .
C28 C29 H29 119.4 . .
C30 C29 H29 119.4 . .
C31 C30 C29 119.7(6) . .
C31 C30 H30 120.1 . .
C29 C30 H30 120.1 . .
C30 C31 C32 119.9(6) . .
C30 C31 H31 120.1 . .
C32 C31 H31 120.1 . .
C31 C32 C33 120.7(6) . .
C31 C32 H32 119.7 . .
C33 C32 H32 119.7 . .
C32 C33 C28 120.1(6) . .
C32 C33 H33 120.0 . .
C28 C33 H33 120.0 . .
C39 C34 C35 118.6(6) . .
C39 C34 C26 122.5(5) . .
C35 C34 C26 118.9(5) . .
C36 C35 C34 120.0(9) . .
C36 C35 H35 120.0 . .
C34 C35 H35 120.0 . .
C35 C36 C37 120.9(10) . .
C35 C36 H36 119.6 . .
C37 C36 H36 119.6 . .
C38 C37 C36 120.3(9) . .
C38 C37 H37 119.9 . .
C36 C37 H37 119.9 . .
C37 C38 C39 118.9(9) . .
C37 C38 H38 120.6 . .
C39 C38 H38 120.6 . .
C38 C39 C34 121.4(8) . .
C38 C39 H39 119.3 . .
C34 C39 H39 119.3 . .
C25 C40 C41 112.1(5) . .
C25 C40 H40A 109.2 . .
C41 C40 H40A 109.2 . .
C25 C40 H40B 109.2 . .
C41 C40 H40B 109.2 . .
H40A C40 H40B 107.9 . .
C42 C41 C40 111.1(6) . .
C42 C41 H41A 109.4 . .
C40 C41 H41A 109.4 . .
C42 C41 H41B 109.4 . .
C40 C41 H41B 109.4 . .
H41A C41 H41B 108.0 . .
C41 C42 H42A 109.5 . .
C41 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C41 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
O3 C43 C24 122.8(6) . .
O3 C43 C44 117.0(6) . .
C24 C43 C44 120.2(5) . .
F8 C44 F9 106.7(6) . .
F8 C44 C45 113.2(6) . .
F9 C44 C45 106.5(5) . .
F8 C44 C43 111.5(5) . .
F9 C44 C43 110.1(5) . .
C45 C44 C43 108.8(6) . .
F10 C45 F11 110.6(9) . .
F10 C45 C46 108.8(7) . .
F11 C45 C46 103.0(6) . .
F10 C45 C44 110.5(6) . .
F11 C45 C44 109.5(6) . .
C46 C45 C44 114.2(7) . .
F14 C46 F13 107.9(10) . .
F14 C46 F12 106.6(8) . .
F13 C46 F12 105.0(7) . .
F14 C46 C45 111.4(8) . .
F13 C46 C45 111.4(8) . .
F12 C46 C45 114.1(7) . .
C4 O1 C1 105.9(4) . .
C2 C1 O1 109.9(5) . .
C2 C1 C20 132.9(6) . .
O1 C1 C20 117.2(6) . .
C1 C2 C3 106.7(5) . .
C1 C2 C17 127.1(6) . .
C3 C2 C17 126.2(6) . .
C4 C3 C2 107.1(5) . .
C4 C3 C11 126.9(5) . .
C2 C3 C11 125.9(5) . .
C3 C4 O1 110.3(5) . .
C3 C4 C5 135.4(5) . .
O1 C4 C5 114.3(4) . .
C6 C5 C10 118.5(5) . .
C6 C5 C4 121.6(5) . .
C10 C5 C4 119.9(5) . .
C7 C6 C5 121.1(6) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C8 120.1(6) . .
C6 C7 H7 119.9 . .
C8 C7 H7 119.9 . .
C9 C8 C7 119.8(6) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C8 C9 C10 121.0(6) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
C9 C10 C5 119.5(5) . .
C9 C10 H10 120.3 . .
C5 C10 H10 120.3 . .
C12 C11 C16 118.3(7) . .
C12 C11 C3 119.3(6) . .
C16 C11 C3 122.4(6) . .
C11 C12 C13 123.9(9) . .
C11 C12 H12 118.1 . .
C13 C12 H12 118.1 . .
C14 C13 C12 117.3(10) . .
C14 C13 H13 121.4 . .
C12 C13 H13 121.4 . .
C13 C14 C15 122.0(10) . .
C13 C14 H14 119.0 . .
C15 C14 H14 119.0 . .
C16 C15 C14 119.3(9) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
C11 C16 C15 119.2(8) . .
C11 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C18 C17 C2 113.0(5) . .
C18 C17 H17A 109.0 . .
C2 C17 H17A 109.0 . .
C18 C17 H17B 109.0 . .
C2 C17 H17B 109.0 . .
H17A C17 H17B 107.8 . .
C17 C18 C19 110.6(6) . .
C17 C18 H18A 109.5 . .
C19 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C19 C18 H18B 109.5 . .
H18A C18 H18B 108.1 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O2 C20 C1 123.4(8) . .
O2 C20 C21 116.1(7) . .
C1 C20 C21 119.5(6) . .
F2 C21 F1 109.3(7) . .
F2 C21 C22 113.1(7) . .
F1 C21 C22 107.3(7) . .
F2 C21 C20 114.3(6) . .
F1 C21 C20 111.5(7) . .
C22 C21 C20 101.0(7) . .
F3 C22 F4 106.1(10) . .
F3 C22 C21 115.3(7) . .
F4 C22 C21 104.8(8) . .
F3 C22 C23 112.4(9) . .
F4 C22 C23 108.3(8) . .
C21 C22 C23 109.5(9) . .
F5 C23 F6 103.8(10) . .
F5 C23 F7 107.5(10) . .
F6 C23 F7 104.5(9) . .
F5 C23 C22 117.6(10) . .
F6 C23 C22 110.5(9) . .
F7 C23 C22 112.0(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C43 1.211(7) .
O4 C27 1.357(6) .
O4 C24 1.364(6) .
F8 C44 1.334(6) .
F9 C44 1.349(6) .
F10 C45 1.280(7) .
F11 C45 1.338(7) .
F12 C46 1.276(7) .
F13 C46 1.262(7) .
F14 C46 1.256(7) .
C24 C25 1.388(8) .
C24 C43 1.428(8) .
C25 C26 1.403(7) .
C25 C40 1.499(7) .
C26 C27 1.371(7) .
C26 C34 1.471(7) .
C27 C28 1.470(7) .
C28 C29 1.363(7) .
C28 C33 1.388(7) .
C29 C30 1.387(8) .
C29 H29 0.9300 .
C30 C31 1.362(9) .
C30 H30 0.9300 .
C31 C32 1.363(9) .
C31 H31 0.9300 .
C32 C33 1.377(8) .
C32 H32 0.9300 .
C33 H33 0.9300 .
C34 C39 1.375(8) .
C34 C35 1.392(8) .
C35 C36 1.334(11) .
C35 H35 0.9300 .
C36 C37 1.388(15) .
C36 H36 0.9300 .
C37 C38 1.354(14) .
C37 H37 0.9300 .
C38 C39 1.371(11) .
C38 H38 0.9300 .
C39 H39 0.9300 .
C40 C41 1.537(9) .
C40 H40A 0.9700 .
C40 H40B 0.9700 .
C41 C42 1.504(9) .
C41 H41A 0.9700 .
C41 H41B 0.9700 .
C42 H42A 0.9600 .
C42 H42B 0.9600 .
C42 H42C 0.9600 .
C43 C44 1.564(10) .
C44 C45 1.517(8) .
C45 C46 1.514(8) .
O1 C4 1.369(6) .
O1 C1 1.381(6) .
O2 C20 1.193(8) .
F1 C21 1.317(7) .
F2 C21 1.308(7) .
F3 C22 1.274(8) .
F4 C22 1.358(8) .
F5 C23 1.267(8) .
F6 C23 1.274(8) .
F7 C23 1.285(8) .
C1 C2 1.357(8) .
C1 C20 1.447(10) .
C2 C3 1.406(8) .
C2 C17 1.514(8) .
C3 C4 1.352(7) .
C3 C11 1.463(8) .
C4 C5 1.452(7) .
C5 C6 1.374(7) .
C5 C10 1.402(8) .
C6 C7 1.367(8) .
C6 H6 0.9300 .
C7 C8 1.379(9) .
C7 H7 0.9300 .
C8 C9 1.355(9) .
C8 H8 0.9300 .
C9 C10 1.382(8) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C12 1.377(9) .
C11 C16 1.385(8) .
C12 C13 1.378(11) .
C12 H12 0.9300 .
C13 C14 1.348(15) .
C13 H13 0.9300 .
C14 C15 1.401(14) .
C14 H14 0.9300 .
C15 C16 1.402(12) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18 1.496(9) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.531(9) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 C21 1.658(12) .
C21 C22 1.492(8) .
C22 C23 1.540(9) .
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
C27 O4 C24 C25 0.2(6) . . . .
C27 O4 C24 C43 179.6(5) . . . .
O4 C24 C25 C26 0.9(6) . . . .
C43 C24 C25 C26 -178.4(6) . . . .
O4 C24 C25 C40 -179.9(5) . . . .
C43 C24 C25 C40 0.8(10) . . . .
C24 C25 C26 C27 -1.7(6) . . . .
C40 C25 C26 C27 179.1(5) . . . .
C24 C25 C26 C34 174.6(5) . . . .
C40 C25 C26 C34 -4.5(9) . . . .
C24 O4 C27 C26 -1.3(6) . . . .
C24 O4 C27 C28 177.9(4) . . . .
C25 C26 C27 O4 1.9(6) . . . .
C34 C26 C27 O4 -174.5(5) . . . .
C25 C26 C27 C28 -177.1(5) . . . .
C34 C26 C27 C28 6.6(9) . . . .
O4 C27 C28 C29 18.1(7) . . . .
C26 C27 C28 C29 -162.9(6) . . . .
O4 C27 C28 C33 -160.0(5) . . . .
C26 C27 C28 C33 18.9(9) . . . .
C33 C28 C29 C30 -0.2(9) . . . .
C27 C28 C29 C30 -178.4(6) . . . .
C28 C29 C30 C31 0.2(11) . . . .
C29 C30 C31 C32 -0.8(11) . . . .
C30 C31 C32 C33 1.6(10) . . . .
C31 C32 C33 C28 -1.7(9) . . . .
C29 C28 C33 C32 1.0(9) . . . .
C27 C28 C33 C32 179.1(5) . . . .
C27 C26 C34 C39 -121.7(6) . . . .
C25 C26 C34 C39 62.6(8) . . . .
C27 C26 C34 C35 58.0(8) . . . .
C25 C26 C34 C35 -117.7(6) . . . .
C39 C34 C35 C36 -0.4(10) . . . .
C26 C34 C35 C36 179.8(7) . . . .
C34 C35 C36 C37 0.2(14) . . . .
C35 C36 C37 C38 0.0(16) . . . .
C36 C37 C38 C39 0.0(15) . . . .
C37 C38 C39 C34 -0.3(12) . . . .
C35 C34 C39 C38 0.5(9) . . . .
C26 C34 C39 C38 -179.8(6) . . . .
C24 C25 C40 C41 -82.0(8) . . . .
C26 C25 C40 C41 97.0(7) . . . .
C25 C40 C41 C42 -180.0(6) . . . .
O4 C24 C43 O3 173.4(6) . . . .
C25 C24 C43 O3 -7.3(11) . . . .
O4 C24 C43 C44 -8.8(9) . . . .
C25 C24 C43 C44 170.5(6) . . . .
O3 C43 C44 F8 139.7(6) . . . .
C24 C43 C44 F8 -38.2(8) . . . .
O3 C43 C44 F9 21.6(9) . . . .
C24 C43 C44 F9 -156.3(6) . . . .
O3 C43 C44 C45 -94.8(7) . . . .
C24 C43 C44 C45 87.3(7) . . . .
F8 C44 C45 F10 61.8(9) . . . .
F9 C44 C45 F10 178.6(7) . . . .
C43 C44 C45 F10 -62.7(8) . . . .
F8 C44 C45 F11 -176.2(7) . . . .
F9 C44 C45 F11 -59.3(9) . . . .
C43 C44 C45 F11 59.3(8) . . . .
F8 C44 C45 C46 -61.3(8) . . . .
F9 C44 C45 C46 55.6(8) . . . .
C43 C44 C45 C46 174.2(6) . . . .
F10 C45 C46 F14 -72.3(11) . . . .
F11 C45 C46 F14 170.4(10) . . . .
C44 C45 C46 F14 51.7(11) . . . .
F10 C45 C46 F13 167.2(9) . . . .
F11 C45 C46 F13 49.8(11) . . . .
C44 C45 C46 F13 -68.9(10) . . . .
F10 C45 C46 F12 48.5(10) . . . .
F11 C45 C46 F12 -68.8(9) . . . .
C44 C45 C46 F12 172.5(7) . . . .
C4 O1 C1 C2 1.4(7) . . . .
C4 O1 C1 C20 -177.5(6) . . . .
O1 C1 C2 C3 -2.9(7) . . . .
C20 C1 C2 C3 175.8(8) . . . .
O1 C1 C2 C17 179.4(6) . . . .
C20 C1 C2 C17 -1.9(13) . . . .
C1 C2 C3 C4 3.3(7) . . . .
C17 C2 C3 C4 -179.0(6) . . . .
C1 C2 C3 C11 -173.7(6) . . . .
C17 C2 C3 C11 4.0(10) . . . .
C2 C3 C4 O1 -2.5(6) . . . .
C11 C3 C4 O1 174.4(5) . . . .
C2 C3 C4 C5 176.3(6) . . . .
C11 C3 C4 C5 -6.8(10) . . . .
C1 O1 C4 C3 0.7(6) . . . .
C1 O1 C4 C5 -178.4(5) . . . .
C3 C4 C5 C6 160.8(6) . . . .
O1 C4 C5 C6 -20.4(7) . . . .
C3 C4 C5 C10 -19.9(9) . . . .
O1 C4 C5 C10 158.9(5) . . . .
C10 C5 C6 C7 1.4(8) . . . .
C4 C5 C6 C7 -179.3(5) . . . .
C5 C6 C7 C8 -1.2(10) . . . .
C6 C7 C8 C9 0.6(11) . . . .
C7 C8 C9 C10 -0.1(11) . . . .
C8 C9 C10 C5 0.3(10) . . . .
C6 C5 C10 C9 -1.0(9) . . . .
C4 C5 C10 C9 179.8(5) . . . .
C4 C3 C11 C12 -66.1(9) . . . .
C2 C3 C11 C12 110.2(7) . . . .
C4 C3 C11 C16 114.6(7) . . . .
C2 C3 C11 C16 -69.0(8) . . . .
C16 C11 C12 C13 -0.5(12) . . . .
C3 C11 C12 C13 -179.8(8) . . . .
C11 C12 C13 C14 0.8(16) . . . .
C12 C13 C14 C15 -1.1(18) . . . .
C13 C14 C15 C16 1.3(17) . . . .
C12 C11 C16 C15 0.6(10) . . . .
C3 C11 C16 C15 179.9(6) . . . .
C14 C15 C16 C11 -1.0(13) . . . .
C1 C2 C17 C18 93.5(9) . . . .
C3 C2 C17 C18 -83.8(9) . . . .
C2 C17 C18 C19 178.2(7) . . . .
C2 C1 C20 O2 3.6(15) . . . .
O1 C1 C20 O2 -177.7(8) . . . .
C2 C1 C20 C21 -164.3(8) . . . .
O1 C1 C20 C21 14.4(11) . . . .
O2 C20 C21 F2 -139.7(9) . . . .
C1 C20 C21 F2 29.0(12) . . . .
O2 C20 C21 F1 -15.2(12) . . . .
C1 C20 C21 F1 153.6(8) . . . .
O2 C20 C21 C22 98.5(9) . . . .
C1 C20 C21 C22 -92.7(8) . . . .
F2 C21 C22 F3 -67.9(11) . . . .
F1 C21 C22 F3 171.4(8) . . . .
C20 C21 C22 F3 54.6(9) . . . .
F2 C21 C22 F4 175.9(7) . . . .
F1 C21 C22 F4 55.2(10) . . . .
C20 C21 C22 F4 -61.6(8) . . . .
F2 C21 C22 C23 60.0(9) . . . .
F1 C21 C22 C23 -60.7(9) . . . .
C20 C21 C22 C23 -177.5(6) . . . .
F3 C22 C23 F5 82.8(14) . . . .
F4 C22 C23 F5 -160.4(12) . . . .
C21 C22 C23 F5 -46.8(13) . . . .
F3 C22 C23 F6 -158.4(10) . . . .
F4 C22 C23 F6 -41.6(13) . . . .
C21 C22 C23 F6 72.0(11) . . . .
F3 C22 C23 F7 -42.4(12) . . . .
F4 C22 C23 F7 74.4(12) . . . .
C21 C22 C23 F7 -172.0(9) . . . .
