# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yamada1
_database_code_depnum_ccdc_archive 'CCDC 1902233'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Agou'
;Ibaraki University
Japan
;
_audit_update_record             
;
2019-03-10 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
3,3,4,4,5,5-hexafluoro-1,2-bis[2,3,5,6-tetrafluoro-4-(2-(4-methoxyphenyl)ethyn-1-yl)phenyl]cyclopentene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H14 F14 O2'
_chemical_formula_sum            'C35 H14 F14 O2'
_chemical_formula_weight         732.46

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.2739(8)
_cell_length_b                   20.464(3)
_cell_length_c                   23.723(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3045.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2848
_cell_measurement_theta_min      2.1050
_cell_measurement_theta_max      28.8040

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.06012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.511
_oxdiff_exptl_absorpt_empirical_full_max 11.947
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax Mo'
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10373
_diffrn_reflns_av_unetI/netI     0.1653
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.984
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5375
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0936P)²+1.6369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5375
_refine_ls_number_parameters     507
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2656
_refine_ls_wR_factor_gt          0.1748
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8462(11) 0.5082(4) 0.0946(3) 0.074(2) Uani 1 1 d . . . . .
F2 F 1.4804(11) 0.4736(4) 0.1968(3) 0.081(2) Uani 1 1 d . . . . .
F3 F 0.9861(13) 0.4297(4) 0.0141(3) 0.091(3) Uani 1 1 d . . . . .
O1 O 1.8060(13) 0.1924(4) -0.1973(3) 0.069(2) Uani 1 1 d . . . . .
F4 F 1.6184(11) 0.3924(4) 0.1179(3) 0.080(2) Uani 1 1 d . . . . .
F5 F 0.8314(12) 0.4169(4) 0.2518(3) 0.083(2) Uani 1 1 d . . . . .
C1 C 1.459(2) 0.3318(7) -0.0161(5) 0.067(4) Uani 1 1 d . . . . .
F6 F 1.4657(13) 0.5147(4) 0.3153(4) 0.101(3) Uani 1 1 d . . . . .
C2 C 1.4241(19) 0.4222(6) 0.1122(5) 0.058(3) Uani 1 1 d . . . . .
F7 F 0.9097(14) 0.3121(4) 0.3163(4) 0.097(3) Uani 1 1 d . . . . .
C3 C 1.447(2) 0.2435(6) -0.0857(5) 0.060(3) Uani 1 1 d . . . . .
H1 H 1.313852 0.230680 -0.072312 0.072 Uiso 1 1 calc R U . . .
C4 C 1.732(2) 0.2292(6) -0.1522(5) 0.056(3) Uani 1 1 d . . . . .
C5 C 1.232(2) 0.3570(7) 0.3499(5) 0.059(3) Uani 1 1 d . . . . .
C6 C 1.112(2) 0.4387(7) 0.0605(5) 0.062(3) Uani 1 1 d . . . . .
C7 C 1.0901(16) 0.5290(6) 0.2510(5) 0.051(3) Uani 1 1 d . . . . .
C8 C 1.009(2) 0.4159(6) 0.2840(5) 0.060(3) Uani 1 1 d . . . . .
C9 C 1.311(2) 0.4087(6) 0.0632(5) 0.059(3) Uani 1 1 d . . . . .
C10 C 1.401(2) 0.2015(6) 0.4443(5) 0.061(3) Uani 1 1 d . . . . .
C11 C 1.554(2) 0.2949(6) -0.0606(5) 0.059(3) Uani 1 1 d . . . . .
C12 C 1.537(2) 0.2116(6) -0.1304(5) 0.062(3) Uani 1 1 d . . . . .
H2 H 1.464459 0.176766 -0.146572 0.075 Uiso 1 1 calc R U . . .
C13 C 1.1462(19) 0.4700(6) 0.2828(5) 0.054(3) Uani 1 1 d . . . . .
C14 C 1.387(2) 0.3657(6) 0.0199(5) 0.067(4) Uani 1 1 d . . . . .
C15 C 1.086(2) 0.5381(6) 0.1941(5) 0.062(3) Uani 1 1 d . . . . .
C16 C 1.155(2) 0.4935(6) 0.1497(5) 0.064(4) Uani 1 1 d . . . . .
F8 F 1.5495(13) 0.4094(5) 0.3771(4) 0.116(4) Uani 1 1 d . . . . .
O2 O 1.6064(17) 0.0371(5) 0.5316(4) 0.088(3) Uani 1 1 d . . . . .
C30 C 1.349(2) 0.4623(6) 0.1527(5) 0.062(3) Uani 1 1 d . . . . .
C31 C 2.003(2) 0.2137(7) -0.2231(5) 0.077(4) Uani 1 1 d . . . . .
H3 H 1.984066 0.256280 -0.239254 0.116 Uiso 1 1 calc R U . . .
H4 H 2.043817 0.183389 -0.252042 0.116 Uiso 1 1 calc R U . . .
H5 H 2.113434 0.215550 -0.194961 0.116 Uiso 1 1 calc R U . . .
C32 C 1.664(3) 0.1244(8) 0.4707(6) 0.089(5) Uani 1 1 d . . . . .
H6 H 1.804007 0.109607 0.467353 0.107 Uiso 1 1 calc R U . . .
C33 C 1.463(3) 0.0000(8) 0.5645(6) 0.098(5) Uani 1 1 d . . . . .
H7 H 1.398436 0.027608 0.592314 0.147 Uiso 1 1 calc R U . . .
H8 H 1.539260 -0.034719 0.582867 0.147 Uiso 1 1 calc R U . . .
H9 H 1.354847 -0.018198 0.540616 0.147 Uiso 1 1 calc R U . . .
F9 F 1.1632(16) 0.6125(4) 0.3177(4) 0.107(3) Uani 1 1 d . . . . .
F10 F 0.8412(15) 0.5791(4) 0.3107(4) 0.118(4) Uani 1 1 d . . . . .
F11 F 0.845(3) 0.6844(10) 0.2391(8) 0.086(4) Uani 0.5 1 d . U P A 2
F12 F 1.190(3) 0.6715(8) 0.2277(6) 0.085(4) Uani 0.5 1 d . U P A 2
F13 F 0.747(2) 0.5931(8) 0.1726(6) 0.076(4) Uani 0.5 1 d . U P A 2
C34 C 0.980(3) 0.6380(8) 0.2343(6) 0.085(3) Uani 1 1 d . U . . .
F14 F 1.043(4) 0.6293(17) 0.1320(13) 0.076(5) Uani 0.5 1 d . U P A 2
C35 C 0.958(6) 0.5972(17) 0.1794(17) 0.077(4) Uani 0.5 1 d . U P A 2
F15 F 1.255(3) 0.6460(8) 0.1821(8) 0.095(4) Uani 0.5 1 d . U P A 1
C17 C 1.016(2) 0.5897(7) 0.2804(5) 0.067(4) Uani 1 1 d . . . . .
C18 C 1.038(2) 0.4786(7) 0.1010(5) 0.063(3) Uani 1 1 d . . . . .
C19 C 1.754(2) 0.3107(7) -0.0818(5) 0.070(4) Uani 1 1 d . . . . .
H10 H 1.830388 0.344296 -0.064852 0.083 Uiso 1 1 calc R U . . .
C20 C 1.329(2) 0.4665(7) 0.3149(5) 0.066(4) Uani 1 1 d . . . . .
C21 C 1.281(2) 0.3021(7) 0.3830(5) 0.071(4) Uani 1 1 d . . . . .
C22 C 1.322(2) 0.1143(7) 0.5084(5) 0.070(4) Uani 1 1 d . . . . .
H11 H 1.223801 0.093544 0.531610 0.084 Uiso 1 1 calc R U . . .
C23 C 1.262(2) 0.1678(7) 0.4791(5) 0.074(4) Uani 1 1 d . . . . .
H12 H 1.122043 0.182500 0.482486 0.089 Uiso 1 1 calc R U . . .
C24 C 1.334(2) 0.2569(7) 0.4114(5) 0.069(4) Uani 1 1 d . . . . .
C25 C 1.366(2) 0.4120(9) 0.3463(6) 0.082(5) Uani 1 1 d . . . . .
C26 C 1.048(2) 0.3615(7) 0.3161(5) 0.065(3) Uani 1 1 d . . . . .
C27 C 1.842(2) 0.2786(6) -0.1264(5) 0.062(3) Uani 1 1 d . . . . .
H13 H 1.976913 0.290225 -0.139225 0.074 Uiso 1 1 calc R U . . .
C28 C 1.526(2) 0.0898(7) 0.5045(5) 0.063(3) Uani 1 1 d . . . . .
C29 C 1.606(3) 0.1792(7) 0.4421(6) 0.085(5) Uani 1 1 d . . . . .
H14 H 1.706902 0.201588 0.420779 0.102 Uiso 1 1 calc R U . . .
F16 F 0.734(3) 0.6293(10) 0.2317(7) 0.099(4) Uani 0.5 1 d . U P A 1
F17 F 0.977(4) 0.6985(9) 0.2502(8) 0.094(4) Uani 0.5 1 d . U P A 1
F18 F 0.963(4) 0.6265(18) 0.1380(14) 0.079(5) Uani 0.5 1 d . U P A 1
C36 C 1.042(6) 0.6130(18) 0.1846(17) 0.080(4) Uani 0.5 1 d . U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C18 1.356(14) . ?
F2 C30 1.351(13) . ?
F3 C6 1.366(13) . ?
O1 C4 1.387(13) . ?
O1 C31 1.449(14) . ?
F4 C2 1.370(13) . ?
F5 C8 1.351(13) . ?
C1 C14 1.189(16) . ?
C1 C11 1.427(17) . ?
F6 C20 1.306(14) . ?
C2 C30 1.347(16) . ?
C2 C9 1.389(16) . ?
F7 C26 1.332(14) . ?
C3 C12 1.368(15) . ?
C3 C11 1.383(16) . ?
C4 C12 1.374(16) . ?
C4 C27 1.370(16) . ?
C5 C26 1.410(17) . ?
C5 C25 1.408(19) . ?
C5 C21 1.404(17) . ?
C6 C18 1.341(17) . ?
C6 C9 1.393(17) . ?
C7 C15 1.363(15) . ?
C7 C13 1.465(16) . ?
C7 C17 1.497(17) . ?
C8 C26 1.371(17) . ?
C8 C13 1.403(17) . ?
C9 C14 1.435(17) . ?
C10 C29 1.366(19) . ?
C10 C23 1.388(17) . ?
C10 C24 1.437(18) . ?
C11 C19 1.391(17) . ?
C13 C20 1.381(16) . ?
C15 C16 1.457(16) . ?
C15 C35 1.49(4) . ?
C15 C36 1.57(4) . ?
C16 C30 1.380(17) . ?
C16 C18 1.403(17) . ?
F8 C25 1.365(15) . ?
O2 C28 1.353(15) . ?
O2 C33 1.411(16) . ?
C32 C28 1.375(18) . ?
C32 C29 1.362(19) . ?
F9 C17 1.359(15) . ?
F10 C17 1.332(14) . ?
F11 C34 1.28(2) . ?
F12 C34 1.49(2) . ?
F13 C35 1.34(4) . ?
C34 F17 1.30(2) . ?
C34 C36 1.34(4) . ?
C34 C17 1.490(19) . ?
C34 F16 1.56(2) . ?
C34 C35 1.55(4) . ?
F14 C35 1.41(5) . ?
F15 C36 1.50(4) . ?
C19 C27 1.362(16) . ?
C20 C25 1.36(2) . ?
C21 C24 1.192(17) . ?
C22 C23 1.349(17) . ?
C22 C28 1.380(18) . ?
F18 C36 1.24(5) . ?

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
C4 O1 C31 116.7(10) . . ?
C14 C1 C11 176.1(15) . . ?
C30 C2 F4 120.6(11) . . ?
C30 C2 C9 122.7(12) . . ?
F4 C2 C9 116.7(11) . . ?
C12 C3 C11 119.7(12) . . ?
O1 C4 C12 116.5(12) . . ?
O1 C4 C27 125.2(12) . . ?
C12 C4 C27 118.2(11) . . ?
C26 C5 C25 113.7(12) . . ?
C26 C5 C21 123.4(14) . . ?
C25 C5 C21 122.9(13) . . ?
C18 C6 F3 117.4(12) . . ?
C18 C6 C9 122.9(12) . . ?
F3 C6 C9 119.7(12) . . ?
C15 C7 C13 128.7(11) . . ?
C15 C7 C17 110.0(11) . . ?
C13 C7 C17 121.2(10) . . ?
F5 C8 C26 118.3(12) . . ?
F5 C8 C13 118.8(11) . . ?
C26 C8 C13 122.9(12) . . ?
C6 C9 C2 114.2(12) . . ?
C6 C9 C14 122.3(12) . . ?
C2 C9 C14 123.5(12) . . ?
C29 C10 C23 116.7(12) . . ?
C29 C10 C24 121.2(13) . . ?
C23 C10 C24 122.1(13) . . ?
C3 C11 C19 117.3(12) . . ?
C3 C11 C1 121.3(12) . . ?
C19 C11 C1 121.3(13) . . ?
C4 C12 C3 122.4(12) . . ?
C20 C13 C8 117.2(12) . . ?
C20 C13 C7 121.8(12) . . ?
C8 C13 C7 120.9(10) . . ?
C1 C14 C9 176.7(15) . . ?
C7 C15 C16 128.7(12) . . ?
C7 C15 C35 110.5(18) . . ?
C16 C15 C35 119.9(18) . . ?
C7 C15 C36 106.1(17) . . ?
C16 C15 C36 123.9(17) . . ?
C30 C16 C18 113.8(11) . . ?
C30 C16 C15 121.0(12) . . ?
C18 C16 C15 125.2(12) . . ?
C28 O2 C33 117.1(12) . . ?
C2 C30 F2 116.5(11) . . ?
C2 C30 C16 123.6(12) . . ?
F2 C30 C16 119.9(11) . . ?
C28 C32 C29 123.1(14) . . ?
F17 C34 C36 129(2) . . ?
F11 C34 F12 104.7(16) . . ?
F11 C34 C17 121.9(15) . . ?
F17 C34 C17 115.0(15) . . ?
C36 C34 C17 110(2) . . ?
F12 C34 C17 104.3(14) . . ?
F17 C34 F16 96.1(17) . . ?
C36 C34 F16 102(2) . . ?
C17 C34 F16 96.0(14) . . ?
F11 C34 C35 114(2) . . ?
F12 C34 C35 103.8(18) . . ?
C17 C34 C35 105.8(18) . . ?
F13 C35 F14 108(3) . . ?
F13 C35 C15 121(3) . . ?
F14 C35 C15 111(3) . . ?
F13 C35 C34 103(3) . . ?
F14 C35 C34 113(3) . . ?
C15 C35 C34 101(2) . . ?
F10 C17 F9 105.2(10) . . ?
F10 C17 C7 111.8(11) . . ?
F9 C17 C7 112.2(11) . . ?
F10 C17 C34 112.2(13) . . ?
F9 C17 C34 110.8(12) . . ?
C7 C17 C34 104.8(10) . . ?
C6 C18 F1 119.9(12) . . ?
C6 C18 C16 122.9(12) . . ?
F1 C18 C16 117.2(11) . . ?
C27 C19 C11 122.4(13) . . ?
F6 C20 C25 120.3(12) . . ?
F6 C20 C13 120.6(12) . . ?
C25 C20 C13 119.1(13) . . ?
C24 C21 C5 176.4(17) . . ?
C23 C22 C28 121.4(13) . . ?
C22 C23 C10 122.2(13) . . ?
C21 C24 C10 178.3(14) . . ?
C20 C25 F8 118.0(15) . . ?
C20 C25 C5 126.0(13) . . ?
F8 C25 C5 116.0(15) . . ?
F7 C26 C8 120.0(12) . . ?
F7 C26 C5 118.9(12) . . ?
C8 C26 C5 121.1(13) . . ?
C19 C27 C4 119.9(12) . . ?
O2 C28 C32 117.0(13) . . ?
O2 C28 C22 127.1(12) . . ?
C32 C28 C22 115.9(13) . . ?
C10 C29 C32 120.6(14) . . ?
F18 C36 C34 125(4) . . ?
F18 C36 F15 103(3) . . ?
C34 C36 F15 97(2) . . ?
F18 C36 C15 115(3) . . ?
C34 C36 C15 107(3) . . ?
F15 C36 C15 107(2) . . ?

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
C31 O1 C4 C12 175.6(10) . . . . ?
C31 O1 C4 C27 -8.1(16) . . . . ?
C18 C6 C9 C2 1.7(19) . . . . ?
F3 C6 C9 C2 179.3(11) . . . . ?
C18 C6 C9 C14 179.5(13) . . . . ?
F3 C6 C9 C14 -2.8(19) . . . . ?
C30 C2 C9 C6 -1.6(19) . . . . ?
F4 C2 C9 C6 178.1(11) . . . . ?
C30 C2 C9 C14 -179.5(12) . . . . ?
F4 C2 C9 C14 0.3(18) . . . . ?
C12 C3 C11 C19 -1.6(18) . . . . ?
C12 C3 C11 C1 176.4(12) . . . . ?
O1 C4 C12 C3 179.5(11) . . . . ?
C27 C4 C12 C3 3.0(19) . . . . ?
C11 C3 C12 C4 -0.8(19) . . . . ?
F5 C8 C13 C20 -178.2(10) . . . . ?
C26 C8 C13 C20 1.3(19) . . . . ?
F5 C8 C13 C7 5.0(17) . . . . ?
C26 C8 C13 C7 -175.5(11) . . . . ?
C15 C7 C13 C20 111.2(15) . . . . ?
C17 C7 C13 C20 -71.6(16) . . . . ?
C15 C7 C13 C8 -72.2(17) . . . . ?
C17 C7 C13 C8 105.1(14) . . . . ?
C13 C7 C15 C16 -6(2) . . . . ?
C17 C7 C15 C16 176.4(13) . . . . ?
C13 C7 C15 C35 162.4(17) . . . . ?
C17 C7 C15 C35 -15.1(19) . . . . ?
C13 C7 C15 C36 -173.1(17) . . . . ?
C17 C7 C15 C36 9.4(19) . . . . ?
C7 C15 C16 C30 -48(2) . . . . ?
C35 C15 C16 C30 144.7(19) . . . . ?
C36 C15 C16 C30 117(2) . . . . ?
C7 C15 C16 C18 133.2(15) . . . . ?
C35 C15 C16 C18 -34(2) . . . . ?
C36 C15 C16 C18 -62(2) . . . . ?
F4 C2 C30 F2 3.3(18) . . . . ?
C9 C2 C30 F2 -176.9(11) . . . . ?
F4 C2 C30 C16 -179.6(12) . . . . ?
C9 C2 C30 C16 0(2) . . . . ?
C18 C16 C30 C2 1(2) . . . . ?
C15 C16 C30 C2 -177.9(13) . . . . ?
C18 C16 C30 F2 178.3(11) . . . . ?
C15 C16 C30 F2 -1(2) . . . . ?
C7 C15 C35 F13 -86(3) . . . . ?
C16 C15 C35 F13 83(3) . . . . ?
C7 C15 C35 F14 146(2) . . . . ?
C16 C15 C35 F14 -45(3) . . . . ?
C7 C15 C35 C34 26(2) . . . . ?
C16 C15 C35 C34 -164.3(15) . . . . ?
F11 C34 C35 F13 -39(3) . . . . ?
F12 C34 C35 F13 -152(2) . . . . ?
C17 C34 C35 F13 98(2) . . . . ?
F11 C34 C35 F14 77(3) . . . . ?
F12 C34 C35 F14 -36(3) . . . . ?
C17 C34 C35 F14 -146(3) . . . . ?
F11 C34 C35 C15 -164.0(18) . . . . ?
F12 C34 C35 C15 83(2) . . . . ?
C17 C34 C35 C15 -27(2) . . . . ?
C15 C7 C17 F10 118.5(12) . . . . ?
C13 C7 C17 F10 -59.3(16) . . . . ?
C15 C7 C17 F9 -123.6(11) . . . . ?
C13 C7 C17 F9 58.7(15) . . . . ?
C15 C7 C17 C34 -3.3(15) . . . . ?
C13 C7 C17 C34 178.9(12) . . . . ?
F11 C34 C17 F10 31(2) . . . . ?
F17 C34 C17 F10 78(2) . . . . ?
C36 C34 C17 F10 -127(2) . . . . ?
F12 C34 C17 F10 148.6(12) . . . . ?
F16 C34 C17 F10 -21.6(15) . . . . ?
C35 C34 C17 F10 -102.2(19) . . . . ?
F11 C34 C17 F9 -87(2) . . . . ?
F17 C34 C17 F9 -39(2) . . . . ?
C36 C34 C17 F9 116(2) . . . . ?
F12 C34 C17 F9 31.4(15) . . . . ?
F16 C34 C17 F9 -138.8(13) . . . . ?
C35 C34 C17 F9 140.5(17) . . . . ?
F11 C34 C17 C7 152.3(18) . . . . ?
F17 C34 C17 C7 -160.4(17) . . . . ?
C36 C34 C17 C7 -5(2) . . . . ?
F12 C34 C17 C7 -89.9(13) . . . . ?
F16 C34 C17 C7 99.9(13) . . . . ?
C35 C34 C17 C7 19(2) . . . . ?
F3 C6 C18 F1 -0.2(19) . . . . ?
C9 C6 C18 F1 177.5(12) . . . . ?
F3 C6 C18 C16 -177.9(12) . . . . ?
C9 C6 C18 C16 0(2) . . . . ?
C30 C16 C18 C6 -1(2) . . . . ?
C15 C16 C18 C6 177.8(13) . . . . ?
C30 C16 C18 F1 -179.0(11) . . . . ?
C15 C16 C18 F1 0.1(19) . . . . ?
C3 C11 C19 C27 1.8(19) . . . . ?
C1 C11 C19 C27 -176.2(12) . . . . ?
C8 C13 C20 F6 179.1(12) . . . . ?
C7 C13 C20 F6 -4.1(19) . . . . ?
C8 C13 C20 C25 -1.0(19) . . . . ?
C7 C13 C20 C25 175.8(12) . . . . ?
C28 C22 C23 C10 -1(2) . . . . ?
C29 C10 C23 C22 -2(2) . . . . ?
C24 C10 C23 C22 177.5(13) . . . . ?
F6 C20 C25 F8 -1(2) . . . . ?
C13 C20 C25 F8 179.2(11) . . . . ?
F6 C20 C25 C5 179.7(13) . . . . ?
C13 C20 C25 C5 0(2) . . . . ?
C26 C5 C25 C20 1(2) . . . . ?
C21 C5 C25 C20 179.5(13) . . . . ?
C26 C5 C25 F8 -178.3(11) . . . . ?
C21 C5 C25 F8 0(2) . . . . ?
F5 C8 C26 F7 -1.7(18) . . . . ?
C13 C8 C26 F7 178.7(11) . . . . ?
F5 C8 C26 C5 179.1(10) . . . . ?
C13 C8 C26 C5 0(2) . . . . ?
C25 C5 C26 F7 -179.9(12) . . . . ?
C21 C5 C26 F7 1.7(19) . . . . ?
C25 C5 C26 C8 -0.7(18) . . . . ?
C21 C5 C26 C8 -179.1(12) . . . . ?
C11 C19 C27 C4 0(2) . . . . ?
O1 C4 C27 C19 -179.0(11) . . . . ?
C12 C4 C27 C19 -2.8(19) . . . . ?
C33 O2 C28 C32 -177.5(12) . . . . ?
C33 O2 C28 C22 4.8(19) . . . . ?
C29 C32 C28 O2 -178.6(14) . . . . ?
C29 C32 C28 C22 -1(2) . . . . ?
C23 C22 C28 O2 179.7(13) . . . . ?
C23 C22 C28 C32 2(2) . . . . ?
C23 C10 C29 C32 3(2) . . . . ?
C24 C10 C29 C32 -176.1(13) . . . . ?
C28 C32 C29 C10 -2(2) . . . . ?
F17 C34 C36 F18 -60(5) . . . . ?
C17 C34 C36 F18 150(4) . . . . ?
F16 C34 C36 F18 49(4) . . . . ?
F17 C34 C36 F15 51(4) . . . . ?
C17 C34 C36 F15 -99(2) . . . . ?
F16 C34 C36 F15 159.5(18) . . . . ?
F17 C34 C36 C15 162(2) . . . . ?
C17 C34 C36 C15 11(3) . . . . ?
F16 C34 C36 C15 -90(2) . . . . ?
C7 C15 C36 F18 -157(3) . . . . ?
C16 C15 C36 F18 35(4) . . . . ?
C7 C15 C36 C34 -13(3) . . . . ?
C16 C15 C36 C34 179.3(18) . . . . ?
C7 C15 C36 F15 90(2) . . . . ?
C16 C15 C36 F15 -78(3) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/CH2Cl2 (1/1)'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yamada3
_database_code_depnum_ccdc_archive 'CCDC 1902234'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Agou'
;Ibaraki University
Japan
;
_audit_update_record             
;
2019-03-10 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
3,3,4,4,5,5-hexafluoro-1,2-bis[2,3,5,6-tetrafluoro-4-(2-(4-n-propoxyphenyl)ethyn-1-yl)phenyl]cyclopentene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H22 F14 O2'
_chemical_formula_sum            'C39 H22 F14 O2'
_chemical_formula_weight         788.56

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6458(4)
_cell_length_b                   7.7616(3)
_cell_length_c                   31.5448(10)
_cell_angle_alpha                86.116(3)
_cell_angle_beta                 83.893(3)
_cell_angle_gamma                66.440(4)
_cell_volume                     1705.55(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7480
_cell_measurement_theta_min      1.9380
_cell_measurement_theta_max      30.6080

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.635
_oxdiff_exptl_absorpt_empirical_full_max 1.419
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax Mo'
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13328
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.949
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6315
_reflns_number_gt                4625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.3682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6315
_refine_ls_number_parameters     498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.97156(16) 0.19711(15) 0.72722(3) 0.0423(3) Uani 1 1 d . . . . .
F2 F 0.70574(16) -0.10672(16) 0.77085(4) 0.0459(3) Uani 1 1 d . . . . .
F3 F 0.38677(16) 0.05707(17) 0.73210(5) 0.0570(4) Uani 1 1 d . . . . .
F4 F 0.81875(18) 0.51138(16) 0.76951(4) 0.0537(3) Uani 1 1 d . . . . .
F5 F 1.41158(18) -0.26590(18) 0.79955(4) 0.0588(4) Uani 1 1 d . . . . .
F6 F 1.15853(18) -0.53208(17) 0.72240(5) 0.0595(4) Uani 1 1 d . . . . .
F7 F 1.50529(17) -0.34990(19) 0.71897(5) 0.0589(4) Uani 1 1 d . . . . .
F8 F 1.27608(19) -0.39688(18) 0.67229(4) 0.0596(4) Uani 1 1 d . . . . .
F9 F 1.0742(2) -0.14977(18) 0.85731(4) 0.0628(4) Uani 1 1 d . . . . .
F10 F 1.49978(19) -0.61069(17) 0.74685(5) 0.0665(4) Uani 1 1 d . . . . .
F11 F 1.2520(2) -0.44417(17) 0.80877(4) 0.0638(4) Uani 1 1 d . . . . .
F12 F 1.06789(19) -0.0751(2) 0.64231(4) 0.0692(4) Uani 1 1 d . . . . .
F13 F 0.9329(2) 0.1683(2) 0.89908(4) 0.0758(5) Uani 1 1 d . . . . .
F14 F 0.7495(2) 0.0840(2) 0.60379(4) 0.0806(5) Uani 1 1 d . . . . .
O1 O -0.3967(2) 0.7524(3) 0.55057(5) 0.0685(5) Uani 1 1 d . . . . .
O2 O 0.4067(3) 1.3700(2) 0.95019(5) 0.0727(5) Uani 1 1 d . . . . .
C1 C 1.0258(3) 0.0098(3) 0.79053(6) 0.0338(4) Uani 1 1 d . . . . .
C2 C 1.1185(3) -0.1649(3) 0.76667(6) 0.0339(4) Uani 1 1 d . . . . .
C3 C 0.7194(3) -0.0652(3) 0.72908(6) 0.0361(4) Uani 1 1 d . . . . .
C4 C 0.9573(3) 0.1853(3) 0.76990(6) 0.0339(4) Uani 1 1 d . . . . .
C5 C 1.0744(3) -0.2072(3) 0.72989(6) 0.0346(4) Uani 1 1 d . . . . .
C6 C 0.8997(3) -0.1079(3) 0.70755(6) 0.0356(4) Uani 1 1 d . . . . .
C7 C 0.8806(3) 0.3491(3) 0.79158(7) 0.0389(5) Uani 1 1 d . . . . .
C8 C 1.0131(3) 0.0128(3) 0.83479(7) 0.0434(5) Uani 1 1 d . . . . .
C9 C 0.5550(3) 0.0206(3) 0.70906(7) 0.0414(5) Uani 1 1 d . . . . .
C10 C 1.2229(3) -0.3942(3) 0.71438(7) 0.0423(5) Uani 1 1 d . . . . .
C11 C 1.2961(3) -0.3233(3) 0.78092(7) 0.0423(5) Uani 1 1 d . . . . .
C12 C 0.8680(3) 0.3516(3) 0.83575(7) 0.0460(5) Uani 1 1 d . . . . .
C13 C 1.3918(3) -0.4284(3) 0.74000(8) 0.0460(5) Uani 1 1 d . . . . .
C14 C 0.9011(3) -0.0536(3) 0.66480(7) 0.0465(5) Uani 1 1 d . . . . .
C15 C 0.9378(3) 0.1772(3) 0.85652(7) 0.0497(6) Uani 1 1 d . . . . .
C16 C -0.2488(3) 0.6350(3) 0.57262(7) 0.0539(6) Uani 1 1 d . . . . .
C17 C 0.7869(3) 0.5245(3) 0.85746(8) 0.0548(6) Uani 1 1 d . . . . .
C18 C 0.7159(3) 0.6757(3) 0.87311(8) 0.0563(6) Uani 1 1 d . . . . .
C19 C 0.5573(3) 0.0732(3) 0.66636(7) 0.0464(5) Uani 1 1 d . . . . .
C20 C 0.5936(4) 1.0511(3) 0.95096(8) 0.0647(7) Uani 1 1 d . . . . .
H1 H 0.622659 1.064386 0.978786 0.078 Uiso 1 1 calc R U . . .
C21 C 0.4745(4) 1.2065(3) 0.92905(8) 0.0569(6) Uani 1 1 d . . . . .
C22 C 0.2441(4) 0.2688(3) 0.62962(8) 0.0556(6) Uani 1 1 d . . . . .
C23 C 0.6321(3) 0.8552(3) 0.89213(8) 0.0536(6) Uani 1 1 d . . . . .
C24 C 0.3859(4) 0.1733(3) 0.64587(8) 0.0552(6) Uani 1 1 d . . . . .
C25 C -0.2657(4) 0.5602(4) 0.61259(8) 0.0634(7) Uani 1 1 d . . . . .
H2 H -0.388646 0.590910 0.627449 0.076 Uiso 1 1 calc R U . . .
C26 C 0.0763(3) 0.3915(3) 0.61028(8) 0.0524(6) Uani 1 1 d . . . . .
C27 C 0.6705(4) 0.8773(3) 0.93289(8) 0.0642(7) Uani 1 1 d . . . . .
H3 H 0.750757 0.771231 0.948510 0.077 Uiso 1 1 calc R U . . .
C28 C 0.7372(3) 0.0325(3) 0.64482(7) 0.0517(6) Uani 1 1 d . . . . .
C29 C 0.5133(4) 1.0118(4) 0.87046(8) 0.0641(7) Uani 1 1 d . . . . .
H4 H 0.485488 0.999094 0.842486 0.077 Uiso 1 1 calc R U . . .
C30 C -0.1047(4) 0.4405(4) 0.63130(8) 0.0643(7) Uani 1 1 d . . . . .
H5 H -0.117919 0.390422 0.659208 0.077 Uiso 1 1 calc R U . . .
C31 C 0.4342(4) 1.1864(3) 0.88856(8) 0.0668(7) Uani 1 1 d . . . . .
H6 H 0.352234 1.292231 0.873178 0.080 Uiso 1 1 calc R U . . .
C32 C -0.0691(4) 0.5934(4) 0.55195(9) 0.0701(8) Uani 1 1 d . . . . .
H7 H -0.056028 0.649905 0.524780 0.084 Uiso 1 1 calc R U . . .
C33 C 0.0910(4) 0.4713(4) 0.57029(9) 0.0684(7) Uani 1 1 d . . . . .
H8 H 0.213607 0.441110 0.555293 0.082 Uiso 1 1 calc R U . . .
C34 C 0.2888(5) 1.5391(3) 0.92908(9) 0.0766(9) Uani 1 1 d . . . . .
H9 H 0.168427 1.530801 0.922700 0.092 Uiso 1 1 calc R U . . .
H10 H 0.356464 1.559431 0.901902 0.092 Uiso 1 1 calc R U . . .
C35 C 0.2455(5) 1.6992(4) 0.95848(9) 0.0829(9) Uani 1 1 d . . . . .
H11 H 0.367713 1.704108 0.964612 0.100 Uiso 1 1 calc R U . . .
H12 H 0.170865 1.818717 0.943658 0.100 Uiso 1 1 calc R U . . .
C36 C -0.5871(3) 0.7943(4) 0.56900(8) 0.0693(7) Uani 1 1 d . . . . .
H13 H -0.609462 0.860856 0.596015 0.083 Uiso 1 1 calc R U . . .
H14 H -0.607820 0.676821 0.575225 0.083 Uiso 1 1 calc R U . . .
C37 C 0.1357(5) 1.6838(4) 0.99995(10) 0.0904(10) Uani 1 1 d . . . . .
H15 H 0.019679 1.667738 0.994224 0.136 Uiso 1 1 calc R U . . .
H16 H 0.100015 1.798499 1.015987 0.136 Uiso 1 1 calc R U . . .
H17 H 0.215701 1.575157 1.016694 0.136 Uiso 1 1 calc R U . . .
C38 C -0.7211(4) 0.9161(5) 0.53764(10) 0.0931(11) Uani 1 1 d . . . . .
H18 H -0.694496 1.030172 0.530920 0.112 Uiso 1 1 calc R U . . .
H19 H -0.854173 0.956566 0.550866 0.112 Uiso 1 1 calc R U . . .
C39 C -0.7047(5) 0.8195(6) 0.49710(10) 0.1161(14) Uani 1 1 d . . . . .
H20 H -0.581733 0.800732 0.481072 0.174 Uiso 1 1 calc R U . . .
H21 H -0.809463 0.897094 0.479928 0.174 Uiso 1 1 calc R U . . .
H22 H -0.712181 0.697290 0.503733 0.174 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C4 1.339(2) . ?
F2 C3 1.338(2) . ?
F3 C9 1.342(2) . ?
F4 C7 1.331(2) . ?
F5 C11 1.336(2) . ?
F6 C10 1.346(2) . ?
F7 C13 1.346(2) . ?
F8 C10 1.346(2) . ?
F9 C8 1.339(2) . ?
F10 C13 1.339(2) . ?
F11 C11 1.358(2) . ?
F12 C14 1.346(2) . ?
F13 C15 1.337(2) . ?
F14 C28 1.333(2) . ?
O1 C16 1.361(3) . ?
O1 C36 1.425(3) . ?
O2 C21 1.356(3) . ?
O2 C34 1.429(3) . ?
C1 C4 1.391(3) . ?
C1 C8 1.391(3) . ?
C1 C2 1.471(3) . ?
C2 C5 1.339(3) . ?
C2 C11 1.510(3) . ?
C3 C9 1.366(3) . ?
C3 C6 1.392(3) . ?
C4 C7 1.365(3) . ?
C5 C6 1.476(3) . ?
C5 C10 1.515(3) . ?
C6 C14 1.386(3) . ?
C7 C12 1.387(3) . ?
C8 C15 1.370(3) . ?
C9 C19 1.381(3) . ?
C10 C13 1.519(3) . ?
C11 C13 1.527(3) . ?
C12 C15 1.387(3) . ?
C12 C17 1.422(3) . ?
C14 C28 1.363(3) . ?
C16 C25 1.367(3) . ?
C16 C32 1.379(3) . ?
C17 C18 1.195(3) . ?
C18 C23 1.424(3) . ?
C19 C28 1.392(3) . ?
C19 C24 1.427(3) . ?
C20 C27 1.375(3) . ?
C20 C21 1.380(3) . ?
C20 H1 0.9500 . ?
C21 C31 1.378(3) . ?
C22 C24 1.188(3) . ?
C22 C26 1.427(3) . ?
C23 C29 1.381(3) . ?
C23 C27 1.385(3) . ?
C25 C30 1.376(3) . ?
C25 H2 0.9500 . ?
C26 C33 1.381(3) . ?
C26 C30 1.385(3) . ?
C27 H3 0.9500 . ?
C29 C31 1.380(3) . ?
C29 H4 0.9500 . ?
C30 H5 0.9500 . ?
C31 H6 0.9500 . ?
C32 C33 1.371(3) . ?
C32 H7 0.9500 . ?
C33 H8 0.9500 . ?
C34 C35 1.508(3) . ?
C34 H9 0.9900 . ?
C34 H10 0.9900 . ?
C35 C37 1.502(4) . ?
C35 H11 0.9900 . ?
C35 H12 0.9900 . ?
C36 C38 1.496(4) . ?
C36 H13 0.9900 . ?
C36 H14 0.9900 . ?
C37 H15 0.9800 . ?
C37 H16 0.9800 . ?
C37 H17 0.9800 . ?
C38 C39 1.494(5) . ?
C38 H18 0.9900 . ?
C38 H19 0.9900 . ?
C39 H20 0.9800 . ?
C39 H21 0.9800 . ?
C39 H22 0.9800 . ?

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
C16 O1 C36 118.32(19) . . ?
C21 O2 C34 118.83(19) . . ?
C4 C1 C8 115.34(17) . . ?
C4 C1 C2 121.70(17) . . ?
C8 C1 C2 122.80(17) . . ?
C5 C2 C1 128.76(18) . . ?
C5 C2 C11 109.81(17) . . ?
C1 C2 C11 121.31(17) . . ?
F2 C3 C9 118.69(18) . . ?
F2 C3 C6 119.24(17) . . ?
C9 C3 C6 122.06(19) . . ?
F1 C4 C7 117.87(17) . . ?
F1 C4 C1 119.72(16) . . ?
C7 C4 C1 122.38(18) . . ?
C2 C5 C6 128.56(17) . . ?
C2 C5 C10 110.51(17) . . ?
C6 C5 C10 120.60(17) . . ?
C14 C6 C3 115.62(18) . . ?
C14 C6 C5 123.87(18) . . ?
C3 C6 C5 120.50(18) . . ?
F4 C7 C4 118.76(18) . . ?
F4 C7 C12 119.06(17) . . ?
C4 C7 C12 122.17(19) . . ?
F9 C8 C15 118.32(19) . . ?
F9 C8 C1 119.42(18) . . ?
C15 C8 C1 122.25(19) . . ?
F3 C9 C3 118.4(2) . . ?
F3 C9 C19 119.52(19) . . ?
C3 C9 C19 122.08(19) . . ?
F8 C10 F6 106.26(16) . . ?
F8 C10 C5 114.52(17) . . ?
F6 C10 C5 111.19(16) . . ?
F8 C10 C13 110.65(17) . . ?
F6 C10 C13 110.53(18) . . ?
C5 C10 C13 103.76(16) . . ?
F5 C11 F11 107.34(17) . . ?
F5 C11 C2 113.81(16) . . ?
F11 C11 C2 111.64(17) . . ?
F5 C11 C13 112.52(17) . . ?
F11 C11 C13 107.75(17) . . ?
C2 C11 C13 103.68(16) . . ?
C7 C12 C15 115.78(18) . . ?
C7 C12 C17 120.9(2) . . ?
C15 C12 C17 123.4(2) . . ?
F10 C13 F7 107.58(16) . . ?
F10 C13 C10 113.73(17) . . ?
F7 C13 C10 109.23(18) . . ?
F10 C13 C11 113.38(19) . . ?
F7 C13 C11 109.97(17) . . ?
C10 C13 C11 102.86(16) . . ?
F12 C14 C28 117.8(2) . . ?
F12 C14 C6 119.75(19) . . ?
C28 C14 C6 122.3(2) . . ?
F13 C15 C8 118.7(2) . . ?
F13 C15 C12 119.25(19) . . ?
C8 C15 C12 122.1(2) . . ?
O1 C16 C25 125.5(2) . . ?
O1 C16 C32 115.1(2) . . ?
C25 C16 C32 119.3(2) . . ?
C18 C17 C12 175.6(3) . . ?
C17 C18 C23 179.4(3) . . ?
C9 C19 C28 116.05(19) . . ?
C9 C19 C24 122.4(2) . . ?
C28 C19 C24 121.5(2) . . ?
C27 C20 C21 120.6(2) . . ?
C27 C20 H1 119.7 . . ?
C21 C20 H1 119.7 . . ?
O2 C21 C31 125.4(2) . . ?
O2 C21 C20 115.3(2) . . ?
C31 C21 C20 119.3(2) . . ?
C24 C22 C26 177.0(3) . . ?
C29 C23 C27 118.2(2) . . ?
C29 C23 C18 121.3(2) . . ?
C27 C23 C18 120.5(2) . . ?
C22 C24 C19 175.1(2) . . ?
C16 C25 C30 120.0(2) . . ?
C16 C25 H2 120.0 . . ?
C30 C25 H2 120.0 . . ?
C33 C26 C30 117.8(2) . . ?
C33 C26 C22 120.5(2) . . ?
C30 C26 C22 121.7(2) . . ?
C20 C27 C23 120.7(2) . . ?
C20 C27 H3 119.7 . . ?
C23 C27 H3 119.7 . . ?
F14 C28 C14 119.0(2) . . ?
F14 C28 C19 119.2(2) . . ?
C14 C28 C19 121.8(2) . . ?
C31 C29 C23 121.4(2) . . ?
C31 C29 H4 119.3 . . ?
C23 C29 H4 119.3 . . ?
C25 C30 C26 121.3(2) . . ?
C25 C30 H5 119.3 . . ?
C26 C30 H5 119.3 . . ?
C21 C31 C29 119.8(2) . . ?
C21 C31 H6 120.1 . . ?
C29 C31 H6 120.1 . . ?
C33 C32 C16 120.5(2) . . ?
C33 C32 H7 119.7 . . ?
C16 C32 H7 119.7 . . ?
C32 C33 C26 120.9(2) . . ?
C32 C33 H8 119.6 . . ?
C26 C33 H8 119.6 . . ?
O2 C34 C35 107.6(2) . . ?
O2 C34 H9 110.2 . . ?
C35 C34 H9 110.2 . . ?
O2 C34 H10 110.2 . . ?
C35 C34 H10 110.2 . . ?
H9 C34 H10 108.5 . . ?
C37 C35 C34 113.8(3) . . ?
C37 C35 H11 108.8 . . ?
C34 C35 H11 108.8 . . ?
C37 C35 H12 108.8 . . ?
C34 C35 H12 108.8 . . ?
H11 C35 H12 107.7 . . ?
O1 C36 C38 107.6(2) . . ?
O1 C36 H13 110.2 . . ?
C38 C36 H13 110.2 . . ?
O1 C36 H14 110.2 . . ?
C38 C36 H14 110.2 . . ?
H13 C36 H14 108.5 . . ?
C35 C37 H15 109.5 . . ?
C35 C37 H16 109.5 . . ?
H15 C37 H16 109.5 . . ?
C35 C37 H17 109.5 . . ?
H15 C37 H17 109.5 . . ?
H16 C37 H17 109.5 . . ?
C36 C38 C39 113.1(3) . . ?
C36 C38 H18 109.0 . . ?
C39 C38 H18 109.0 . . ?
C36 C38 H19 109.0 . . ?
C39 C38 H19 109.0 . . ?
H18 C38 H19 107.8 . . ?
C38 C39 H20 109.5 . . ?
C38 C39 H21 109.5 . . ?
H20 C39 H21 109.5 . . ?
C38 C39 H22 109.5 . . ?
H20 C39 H22 109.5 . . ?
H21 C39 H22 109.5 . . ?

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
C4 C1 C2 C5 -37.7(3) . . . . ?
C8 C1 C2 C5 147.1(2) . . . . ?
C4 C1 C2 C11 137.9(2) . . . . ?
C8 C1 C2 C11 -37.3(3) . . . . ?
C8 C1 C4 F1 176.95(17) . . . . ?
C2 C1 C4 F1 1.4(3) . . . . ?
C8 C1 C4 C7 -0.8(3) . . . . ?
C2 C1 C4 C7 -176.27(18) . . . . ?
C1 C2 C5 C6 -13.5(3) . . . . ?
C11 C2 C5 C6 170.47(18) . . . . ?
C1 C2 C5 C10 173.22(18) . . . . ?
C11 C2 C5 C10 -2.8(2) . . . . ?
F2 C3 C6 C14 -177.51(16) . . . . ?
C9 C3 C6 C14 1.5(3) . . . . ?
F2 C3 C6 C5 3.4(3) . . . . ?
C9 C3 C6 C5 -177.66(17) . . . . ?
C2 C5 C6 C14 129.4(2) . . . . ?
C10 C5 C6 C14 -57.9(3) . . . . ?
C2 C5 C6 C3 -51.6(3) . . . . ?
C10 C5 C6 C3 121.1(2) . . . . ?
F1 C4 C7 F4 2.0(3) . . . . ?
C1 C4 C7 F4 179.78(17) . . . . ?
F1 C4 C7 C12 -176.95(18) . . . . ?
C1 C4 C7 C12 0.8(3) . . . . ?
C4 C1 C8 F9 179.46(18) . . . . ?
C2 C1 C8 F9 -5.1(3) . . . . ?
C4 C1 C8 C15 0.1(3) . . . . ?
C2 C1 C8 C15 175.6(2) . . . . ?
F2 C3 C9 F3 -1.0(3) . . . . ?
C6 C3 C9 F3 -179.96(17) . . . . ?
F2 C3 C9 C19 177.90(17) . . . . ?
C6 C3 C9 C19 -1.1(3) . . . . ?
C2 C5 C10 F8 -137.22(18) . . . . ?
C6 C5 C10 F8 48.9(2) . . . . ?
C2 C5 C10 F6 102.3(2) . . . . ?
C6 C5 C10 F6 -71.6(2) . . . . ?
C2 C5 C10 C13 -16.5(2) . . . . ?
C6 C5 C10 C13 169.61(18) . . . . ?
C5 C2 C11 F5 143.43(18) . . . . ?
C1 C2 C11 F5 -32.9(3) . . . . ?
C5 C2 C11 F11 -94.9(2) . . . . ?
C1 C2 C11 F11 88.8(2) . . . . ?
C5 C2 C11 C13 20.9(2) . . . . ?
C1 C2 C11 C13 -155.49(17) . . . . ?
F4 C7 C12 C15 -179.12(19) . . . . ?
C4 C7 C12 C15 -0.1(3) . . . . ?
F4 C7 C12 C17 1.2(3) . . . . ?
C4 C7 C12 C17 -179.8(2) . . . . ?
F8 C10 C13 F10 -85.6(2) . . . . ?
F6 C10 C13 F10 31.8(3) . . . . ?
C5 C10 C13 F10 151.06(18) . . . . ?
F8 C10 C13 F7 34.5(2) . . . . ?
F6 C10 C13 F7 151.97(16) . . . . ?
C5 C10 C13 F7 -88.75(19) . . . . ?
F8 C10 C13 C11 151.33(16) . . . . ?
F6 C10 C13 C11 -91.24(19) . . . . ?
C5 C10 C13 C11 28.0(2) . . . . ?
F5 C11 C13 F10 83.7(2) . . . . ?
F11 C11 C13 F10 -34.5(2) . . . . ?
C2 C11 C13 F10 -152.91(17) . . . . ?
F5 C11 C13 F7 -36.8(2) . . . . ?
F11 C11 C13 F7 -154.94(16) . . . . ?
C2 C11 C13 F7 86.61(19) . . . . ?
F5 C11 C13 C10 -153.07(17) . . . . ?
F11 C11 C13 C10 88.80(19) . . . . ?
C2 C11 C13 C10 -29.7(2) . . . . ?
C3 C6 C14 F12 174.54(18) . . . . ?
C5 C6 C14 F12 -6.4(3) . . . . ?
C3 C6 C14 C28 -1.3(3) . . . . ?
C5 C6 C14 C28 177.8(2) . . . . ?
F9 C8 C15 F13 1.6(3) . . . . ?
C1 C8 C15 F13 -179.1(2) . . . . ?
F9 C8 C15 C12 -178.8(2) . . . . ?
C1 C8 C15 C12 0.5(4) . . . . ?
C7 C12 C15 F13 179.1(2) . . . . ?
C17 C12 C15 F13 -1.2(4) . . . . ?
C7 C12 C15 C8 -0.5(3) . . . . ?
C17 C12 C15 C8 179.2(2) . . . . ?
C36 O1 C16 C25 -3.9(4) . . . . ?
C36 O1 C16 C32 177.0(2) . . . . ?
F3 C9 C19 C28 179.26(18) . . . . ?
C3 C9 C19 C28 0.4(3) . . . . ?
F3 C9 C19 C24 2.8(3) . . . . ?
C3 C9 C19 C24 -176.02(19) . . . . ?
C34 O2 C21 C31 -2.4(4) . . . . ?
C34 O2 C21 C20 177.4(3) . . . . ?
C27 C20 C21 O2 179.7(2) . . . . ?
C27 C20 C21 C31 -0.5(4) . . . . ?
O1 C16 C25 C30 179.0(3) . . . . ?
C32 C16 C25 C30 -1.9(4) . . . . ?
C21 C20 C27 C23 0.9(4) . . . . ?
C29 C23 C27 C20 -0.7(4) . . . . ?
C18 C23 C27 C20 178.4(3) . . . . ?
F12 C14 C28 F14 2.8(3) . . . . ?
C6 C14 C28 F14 178.7(2) . . . . ?
F12 C14 C28 C19 -175.2(2) . . . . ?
C6 C14 C28 C19 0.7(4) . . . . ?
C9 C19 C28 F14 -178.19(19) . . . . ?
C24 C19 C28 F14 -1.7(3) . . . . ?
C9 C19 C28 C14 -0.2(3) . . . . ?
C24 C19 C28 C14 176.2(2) . . . . ?
C27 C23 C29 C31 0.0(4) . . . . ?
C18 C23 C29 C31 -179.0(3) . . . . ?
C16 C25 C30 C26 -0.7(4) . . . . ?
C33 C26 C30 C25 1.9(4) . . . . ?
C22 C26 C30 C25 179.5(2) . . . . ?
O2 C21 C31 C29 179.7(3) . . . . ?
C20 C21 C31 C29 -0.1(4) . . . . ?
C23 C29 C31 C21 0.4(4) . . . . ?
O1 C16 C32 C33 -177.7(3) . . . . ?
C25 C16 C32 C33 3.1(4) . . . . ?
C16 C32 C33 C26 -1.9(5) . . . . ?
C30 C26 C33 C32 -0.7(4) . . . . ?
C22 C26 C33 C32 -178.2(3) . . . . ?
C21 O2 C34 C35 -176.2(2) . . . . ?
O2 C34 C35 C37 -62.1(4) . . . . ?
C16 O1 C36 C38 -176.9(3) . . . . ?
O1 C36 C38 C39 63.8(4) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/CH2Cl2 (1/1)'
_exptl_crystal_preparation       Luminescent
