# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_20150104
_database_code_depnum_ccdc_archive 'CCDC 1045554'
_audit_update_record             
;
2015-01-25 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H16 F4 O2'
_chemical_formula_sum            'C19 H16 F4 O2'
_chemical_formula_weight         352.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4F6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.7578(4)
_cell_length_b                   10.8532(6)
_cell_length_c                   18.2457(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1734.27(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.8090
_cell_measurement_theta_min      4.7270
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10669
_diffrn_reflns_theta_full        72.32
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         4.74
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -66.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -77.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -77.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega  -13.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
  6 omega   78.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  160.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   77.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   23.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   30.0000 88

#__ type_ start__ end____ width___ exp.time_
 10 omega   59.00   90.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
 12 omega   45.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00  103.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
 14 omega   48.00   84.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega   51.00   88.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega   49.00   86.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00  152.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 18 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 19 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
 20 omega  105.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   88.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 22 omega   95.00  123.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 23 omega   52.00   86.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -37.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 24 omega  125.00  164.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 25 omega   67.00   92.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   44.00   72.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 27 omega   92.00  162.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
 28 omega  105.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega  152.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   51.00   77.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   85.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   40.00   65.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -37.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   51.00   77.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   74.00  118.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -11.0000   87.7833 44
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0520060000
_diffrn_orient_matrix_UB_12      0.0080788000
_diffrn_orient_matrix_UB_13      -0.0805260000
_diffrn_orient_matrix_UB_21      -0.1310549000
_diffrn_orient_matrix_UB_22      -0.0866590000
_diffrn_orient_matrix_UB_23      -0.0225475000
_diffrn_orient_matrix_UB_31      -0.1050760000
_diffrn_orient_matrix_UB_32      0.1121908000
_diffrn_orient_matrix_UB_33      -0.0116898000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3067
_reflns_number_total             3423
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(17)
_refine_ls_extinction_coef       0.0166(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.038
_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)+(0.0433P)²+0.1340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.6726(2) 0.58466(19) 0.67640(9) 0.1088(6) Uani 1 d . . .
F2 F 0.50093(16) 0.48929(19) 0.73713(10) 0.1054(6) Uani 1 d . . .
F3 F 0.6145(2) 0.64423(15) 0.78466(9) 0.0997(5) Uani 1 d . . .
F4 F 0.5888(3) 0.2872(2) 1.05198(9) 0.1385(9) Uani 1 d . . .
O1 O 0.77444(15) 0.36075(13) 0.72388(7) 0.0586(3) Uani 1 d . . .
O2 O 0.89223(16) 0.52691(13) 0.77507(8) 0.0637(4) Uani 1 d . . .
C1 C 0.9339(3) 0.1764(2) 0.52335(12) 0.0691(5) Uani 1 d . . .
H1 H 1.0262 0.2089 0.5073 0.083 Uiso 1 calc . . R
C2 C 0.8618(3) 0.0860(2) 0.48204(13) 0.0813(7) Uani 1 d . . .
H2 H 0.9058 0.0592 0.4385 0.098 Uiso 1 calc . . R
C3 C 0.7269(3) 0.0363(2) 0.50491(12) 0.0778(6) Uani 1 d . . .
H3 H 0.6799 -0.0255 0.4777 0.093 Uiso 1 calc . . R
C4 C 0.6612(3) 0.0784(2) 0.56842(12) 0.0697(6) Uani 1 d . . .
H4 H 0.5688 0.0453 0.5839 0.084 Uiso 1 calc . . R
C5 C 0.7303(2) 0.16913(19) 0.60967(10) 0.0601(5) Uani 1 d . . .
H5 H 0.6831 0.1972 0.6522 0.072 Uiso 1 calc . . R
C6 C 0.8701(2) 0.21920(16) 0.58837(10) 0.0531(4) Uani 1 d . . .
C7 C 0.9561(2) 0.30966(17) 0.63181(10) 0.0545(4) Uani 1 d . . .
H7 H 1.0542 0.3262 0.6149 0.065 Uiso 1 calc . . R
C8 C 0.91554(19) 0.37119(16) 0.69130(9) 0.0486(4) Uani 1 d . . .
C9 C 1.0097(2) 0.45691(17) 0.73765(10) 0.0516(4) Uani 1 d . . .
C10 C 0.7576(2) 0.45937(18) 0.77480(10) 0.0542(4) Uani 1 d . . .
C11 C 0.7122(2) 0.41049(18) 0.84960(10) 0.0541(4) Uani 1 d . . .
C12 C 0.7634(3) 0.4705(3) 0.91129(12) 0.0747(6) Uani 1 d . . .
H12 H 0.8266 0.5389 0.9068 0.090 Uiso 1 calc . . R
C13 C 0.7207(4) 0.4292(3) 0.98017(13) 0.0886(8) Uani 1 d . . .
H13 H 0.7534 0.4699 1.0222 0.106 Uiso 1 calc . . R
C14 C 0.6303(4) 0.3283(3) 0.98510(13) 0.0868(8) Uani 1 d . . .
C15 C 0.5780(4) 0.2677(2) 0.92526(15) 0.0910(9) Uani 1 d . . .
H15 H 0.5154 0.1990 0.9303 0.109 Uiso 1 calc . . R
C16 C 0.6192(3) 0.3099(2) 0.85630(12) 0.0729(6) Uani 1 d . . .
H16 H 0.5836 0.2698 0.8146 0.087 Uiso 1 calc . . R
C17 C 1.1064(2) 0.5482(2) 0.69560(12) 0.0662(5) Uani 1 d . . .
H17A H 1.0443 0.5894 0.6598 0.099 Uiso 1 calc . . GR
H17B H 1.1879 0.5054 0.6714 0.099 Uiso 1 calc . . GR
H17C H 1.1483 0.6077 0.7289 0.099 Uiso 1 calc . . GR
C18 C 1.1033(3) 0.3855(2) 0.79364(14) 0.0781(6) Uani 1 d . . .
H18A H 1.1457 0.4417 0.8288 0.117 Uiso 1 calc . . GR
H18B H 1.1844 0.3426 0.7691 0.117 Uiso 1 calc . . GR
H18C H 1.0388 0.3272 0.8183 0.117 Uiso 1 calc . . GR
C19 C 0.6342(3) 0.5446(3) 0.74296(13) 0.0765(6) Uani 1 d . . .


_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 C19 1.333(3) . ?
F2 C19 1.317(3) . ?
F3 C19 1.333(3) . ?
F4 C14 1.349(3) . ?
O1 C8 1.376(2) . ?
O1 C10 1.425(2) . ?
O2 C9 1.450(2) . ?
O2 C10 1.388(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.389(3) . ?
C1 C6 1.391(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C6 C7 1.470(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.323(3) . ?
C8 C9 1.503(2) . ?
C9 C17 1.513(3) . ?
C9 C18 1.522(3) . ?
C10 C11 1.517(2) . ?
C10 C19 1.537(3) . ?
C11 C12 1.375(3) . ?
C11 C16 1.368(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.354(4) . ?
C14 C15 1.354(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C8 O1 C10 108.23(14) . . ?
C10 O2 C9 108.91(13) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.39(19) . . ?
C1 C6 C7 118.49(19) . . ?
C5 C6 C7 124.07(17) . . ?
C6 C7 H7 115.0 . . ?
C8 C7 C6 129.94(18) . . ?
C8 C7 H7 115.0 . . ?
O1 C8 C9 107.48(14) . . ?
C7 C8 O1 123.65(16) . . ?
C7 C8 C9 128.80(16) . . ?
O2 C9 C8 101.55(14) . . ?
O2 C9 C17 107.04(16) . . ?
O2 C9 C18 109.45(17) . . ?
C8 C9 C17 115.28(16) . . ?
C8 C9 C18 110.96(16) . . ?
C17 C9 C18 111.86(18) . . ?
O1 C10 C11 110.55(15) . . ?
O1 C10 C19 106.18(16) . . ?
O2 C10 O1 108.12(14) . . ?
O2 C10 C11 113.81(16) . . ?
O2 C10 C19 106.30(17) . . ?
C11 C10 C19 111.49(16) . . ?
C12 C11 C10 119.03(19) . . ?
C16 C11 C10 121.02(18) . . ?
C16 C11 C12 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.7(2) . . ?
C14 C13 H13 120.7 . . ?
F4 C14 C13 119.0(3) . . ?
F4 C14 C15 118.5(3) . . ?
C13 C14 C15 122.5(2) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 120.0(2) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 C19 F3 106.8(2) . . ?
F1 C19 C10 111.29(19) . . ?
F2 C19 F1 107.4(2) . . ?
F2 C19 F3 107.5(2) . . ?
F2 C19 C10 112.3(2) . . ?
F3 C19 C10 111.3(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
F4 C14 C15 C16 179.6(3) . . . . ?
O1 C8 C9 O2 -23.39(18) . . . . ?
O1 C8 C9 C17 -138.68(17) . . . . ?
O1 C8 C9 C18 92.9(2) . . . . ?
O1 C10 C11 C12 146.84(19) . . . . ?
O1 C10 C11 C16 -34.6(3) . . . . ?
O1 C10 C19 F1 -57.8(3) . . . . ?
O1 C10 C19 F2 62.6(2) . . . . ?
O1 C10 C19 F3 -176.80(17) . . . . ?
O2 C10 C11 C12 24.9(3) . . . . ?
O2 C10 C11 C16 -156.49(19) . . . . ?
O2 C10 C19 F1 57.2(3) . . . . ?
O2 C10 C19 F2 177.56(19) . . . . ?
O2 C10 C19 F3 -61.8(2) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C1 C6 C7 C8 173.7(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 176.5(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C4 C5 C6 C7 -175.55(19) . . . . ?
C5 C6 C7 C8 -9.1(3) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C6 C7 C8 O1 -1.1(3) . . . . ?
C6 C7 C8 C9 175.41(18) . . . . ?
C7 C8 C9 O2 159.69(19) . . . . ?
C7 C8 C9 C17 44.4(3) . . . . ?
C7 C8 C9 C18 -84.1(3) . . . . ?
C8 O1 C10 O2 -2.4(2) . . . . ?
C8 O1 C10 C11 -127.61(16) . . . . ?
C8 O1 C10 C19 111.31(17) . . . . ?
C9 O2 C10 O1 -13.3(2) . . . . ?
C9 O2 C10 C11 109.96(17) . . . . ?
C9 O2 C10 C19 -126.93(16) . . . . ?
C10 O1 C8 C7 -166.40(18) . . . . ?
C10 O1 C8 C9 16.48(19) . . . . ?
C10 O2 C9 C8 22.01(19) . . . . ?
C10 O2 C9 C17 143.24(16) . . . . ?
C10 O2 C9 C18 -95.34(19) . . . . ?
C10 C11 C12 C13 178.6(2) . . . . ?
C10 C11 C16 C15 -179.3(2) . . . . ?
C11 C10 C19 F1 -178.3(2) . . . . ?
C11 C10 C19 F2 -57.9(3) . . . . ?
C11 C10 C19 F3 62.7(2) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
C12 C13 C14 F4 179.7(3) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C11 0.5(4) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C19 C10 C11 C12 -95.3(2) . . . . ?
C19 C10 C11 C16 83.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
