# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_345
_database_code_depnum_ccdc_archive 'CCDC 2144835'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 F4'
_chemical_formula_sum            'C18 H12 F4'
_chemical_formula_weight         304.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H12F4
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.9027(7)
_cell_length_b                   9.8059(3)
_cell_length_c                   9.1193(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1422.07(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4905
_cell_measurement_temperature    299
_cell_measurement_theta_max      30.0760
_cell_measurement_theta_min      2.4080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 13 -3 0.3346
-22 -1 -2 0.1215
9 -12 3 0.2930
22 1 2 0.1095
-5 9 -9 0.2912
-1 13 -3 0.3331
2 14 1 0.3449
8 5 11 0.2491
8 -1 12 0.2567
-7 -10 -8 0.0942
6 -9 10 0.3184
-11 11 -5 0.3033
-22 0 1 0.1335
-16 -9 3 0.2443
16 -6 -6 0.1262
11 9 -8 0.2611
-17 1 8 0.2160
-8 13 1 0.3193
-13 -7 8 0.2604
-6 3 12 0.2310
-5 -3 12 0.2509
7 -9 -9 0.1163

_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.242
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1982 13.4448 -3.0351 -0.0268 -0.0063 0.9996
-22.1435 -1.3248 -1.6226 0.9776 0.2089 -0.0240
8.7977 -12.1439 3.4887 -0.3549 -0.0753 -0.9319
22.1786 0.8098 1.7412 -0.9778 -0.2089 -0.0144
-5.3408 9.2215 -9.0744 0.3794 -0.4202 0.8243
-1.0339 13.3329 -3.3811 0.0179 -0.0196 0.9996
1.9602 13.7455 0.9208 -0.2216 0.2458 0.9436
8.1000 4.7654 11.1249 -0.6655 0.7376 0.1139
8.1341 -0.7286 11.9473 -0.6418 0.7112 -0.2867
-6.6812 -9.6411 -8.3728 0.5764 -0.6390 -0.5094
6.0000 -9.0000 10.0000 -0.4327 0.4792 -0.8271
-11.0000 11.0000 -5.0000 0.4955 -0.0154 0.8835
-22.0000 0.0000 1.0000 0.8928 0.4133 0.0201
-16.0000 -9.0000 3.0000 0.6666 0.3240 -0.6588
16.0000 -6.0000 -6.0000 -0.4626 -0.7673 -0.3378
11.0000 9.0000 -8.0000 -0.3288 -0.6015 0.7602
-17.0000 1.0000 8.0000 0.4949 0.8483 -0.0482
-8.0000 13.0000 1.0000 0.1985 0.3950 0.9074
-13.0000 -7.0000 8.0000 0.3954 0.6633 -0.6164
-6.0000 3.0000 12.0000 -0.0845 0.9921 -0.0014
-5.0000 -3.0000 12.0000 -0.0756 0.8845 -0.4240
7.0000 -9.0000 -9.0000 0.0159 -0.8865 -0.4768

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9621
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         2.440
_diffrn_ambient_temperature      299
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  46.00   0.25    1.21    --  -11.80  18.00  23.00  260
  2  ω    -30.00  -5.00   0.25    1.21    --    5.00  57.00 120.00  100
  3  ω     -2.00  24.00   0.25    1.21    --    5.00  57.00 120.00  104
  4  ω     20.00  54.00   0.25    1.21    --    5.00  57.00 150.00  136
  5  ω    -47.00  66.00   0.25    1.21    --  -11.80  57.00  90.00  452
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0417548000
_diffrn_orient_matrix_UB_12      -0.0084381000
_diffrn_orient_matrix_UB_13      -0.0258065000
_diffrn_orient_matrix_UB_21      -0.0155578000
_diffrn_orient_matrix_UB_22      0.0153440000
_diffrn_orient_matrix_UB_23      0.0710598000
_diffrn_orient_matrix_UB_31      -0.0017546000
_diffrn_orient_matrix_UB_32      0.0701419000
_diffrn_orient_matrix_UB_33      -0.0185264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1340
_reflns_number_total             1626
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F001 F 0.56179(7) 0.92121(8) 0.35556(11) 0.0716(3) Uani 1 1 d . . . . .
F002 F 0.43967(6) 0.83624(10) 0.40778(11) 0.0713(3) Uani 1 1 d . . . . .
C003 C 0.55096(8) 0.68170(13) 0.38425(14) 0.0448(3) Uani 1 1 d . . . . .
C004 C 0.60820(8) 0.68426(13) 0.51167(15) 0.0458(3) Uani 1 1 d . . . . .
C005 C 0.51161(9) 0.81158(12) 0.33125(15) 0.0484(3) Uani 1 1 d . . . . .
C006 C 0.52816(10) 0.56870(13) 0.31287(16) 0.0520(4) Uani 1 1 d . . . . .
H006 H 0.5494 0.4856 0.3452 0.062 Uiso 1 1 calc R . . . .
C007 C 0.59765(10) 0.77534(15) 0.62731(16) 0.0550(4) Uani 1 1 d . . . . .
H007 H 0.5533 0.8371 0.6257 0.066 Uiso 1 1 calc R . . . .
C008 C 0.67515(10) 0.59379(15) 0.51794(17) 0.0587(4) Uani 1 1 d . . . . .
H008 H 0.6831 0.5316 0.4422 0.070 Uiso 1 1 calc R . . . .
C009 C 0.65271(11) 0.77452(16) 0.74440(17) 0.0641(4) Uani 1 1 d . . . . .
H009 H 0.6448 0.8353 0.8215 0.077 Uiso 1 1 calc R . . . .
C00A C 0.71888(11) 0.68490(16) 0.74802(19) 0.0674(5) Uani 1 1 d . . . . .
H00A H 0.7559 0.6853 0.8269 0.081 Uiso 1 1 calc R . . . .
C00B C 0.73017(11) 0.59487(18) 0.6350(2) 0.0705(5) Uani 1 1 d . . . . .
H00B H 0.7751 0.5342 0.6372 0.085 Uiso 1 1 calc R . . . .


_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
F001 C005 1.3571(15) . ?
F002 C005 1.3618(17) . ?
C003 C004 1.4763(19) . ?
C003 C005 1.4990(18) . ?
C003 C006 1.3353(19) . ?
C004 C007 1.392(2) . ?
C004 C008 1.387(2) . ?
C005 C005 1.527(3) 3_655 ?
C006 C006 1.455(3) 3_655 ?
C006 H006 0.9300 . ?
C007 H007 0.9300 . ?
C007 C009 1.381(2) . ?
C008 H008 0.9300 . ?
C008 C00B 1.381(2) . ?
C009 H009 0.9300 . ?
C009 C00A 1.371(2) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.369(3) . ?
C00B H00B 0.9300 . ?

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
C004 C003 C005 119.78(11) . . ?
C006 C003 C004 124.42(12) . . ?
C006 C003 C005 115.75(12) . . ?
C007 C004 C003 122.20(12) . . ?
C008 C004 C003 119.66(12) . . ?
C008 C004 C007 118.14(14) . . ?
F001 C005 F002 105.64(10) . . ?
F001 C005 C003 112.02(11) . . ?
F001 C005 C005 107.50(10) . 3_655 ?
F002 C005 C003 109.66(11) . . ?
F002 C005 C005 107.11(14) . 3_655 ?
C003 C005 C005 114.44(9) . 3_655 ?
C003 C006 C006 123.46(8) . 3_655 ?
C003 C006 H006 118.3 . . ?
C006 C006 H006 118.3 3_655 . ?
C004 C007 H007 119.8 . . ?
C009 C007 C004 120.37(15) . . ?
C009 C007 H007 119.8 . . ?
C004 C008 H008 119.6 . . ?
C00B C008 C004 120.90(15) . . ?
C00B C008 H008 119.6 . . ?
C007 C009 H009 119.7 . . ?
C00A C009 C007 120.59(15) . . ?
C00A C009 H009 119.7 . . ?
C009 C00A H00A 120.1 . . ?
C00B C00A C009 119.73(15) . . ?
C00B C00A H00A 120.1 . . ?
C008 C00B H00B 119.9 . . ?
C00A C00B C008 120.27(16) . . ?
C00A C00B H00B 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.780
####################################################################### 
# 
# 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_Yamada-20210121-2_2
_database_code_depnum_ccdc_archive 'CCDC 2144838'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 F4 O2'
_chemical_formula_sum            'C20 H16 F4 O2'
_chemical_formula_weight         364.33

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.8807(11)
_cell_length_b                   9.3734(5)
_cell_length_c                   8.9806(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.599(5)
_cell_angle_gamma                90
_cell_volume                     1668.14(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2599
_cell_measurement_theta_min      2.385
_cell_measurement_theta_max      30.553

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.940
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7343
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1558
_reflns_number_gt                1277
_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 ver. 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Yadokari-XG
_computing_publication_material  Yadokari-XG
_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)+(0.0370P)²+0.8841P] 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         1558
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.58218(7) 0.78050(15) 0.38774(16) 0.0352(4) Uani 1 1 d . . . . .
H1 H 0.5449 0.8441 0.3828 0.042 Uiso 1 1 calc R U . . .
C2 C 0.58959(7) 0.68022(15) 0.50333(16) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.64410(8) 0.58717(17) 0.50407(18) 0.0426(4) Uani 1 1 d . . . . .
H2 H 0.6494 0.5159 0.5794 0.051 Uiso 1 1 calc R U . . .
C4 C 0.69114(8) 0.59535(18) 0.39775(18) 0.0447(4) Uani 1 1 d . . . . .
H3 H 0.7281 0.5308 0.4010 0.054 Uiso 1 1 calc R U . . .
C5 C 0.68367(7) 0.69828(16) 0.28726(17) 0.0373(4) Uani 1 1 d . . . . .
C6 C 0.62805(8) 0.78851(16) 0.28099(17) 0.0374(4) Uani 1 1 d . . . . .
H4 H 0.6216 0.8563 0.2025 0.045 Uiso 1 1 calc R U . . .
C7 C 0.78867(9) 0.6397(2) 0.1885(2) 0.0604(5) Uani 1 1 d . . . . .
H5 H 0.8134 0.6574 0.2856 0.091 Uiso 1 1 calc R U . . .
H6 H 0.8164 0.6695 0.1086 0.091 Uiso 1 1 calc R U . . .
H7 H 0.7785 0.5377 0.1783 0.091 Uiso 1 1 calc R U . . .
C8 C 0.52345(8) 0.55452(15) 0.69127(16) 0.0369(4) Uani 1 1 d . . . . .
H8 H 0.5415 0.4658 0.6624 0.044 Uiso 1 1 calc R U . . .
C9 C 0.54240(7) 0.67317(15) 0.62195(15) 0.0315(3) Uani 1 1 d . . . . .
C10 C 0.50897(7) 0.80851(14) 0.66884(16) 0.0322(3) Uani 1 1 d . . . . .
F1 F 0.45039(4) 0.83088(10) 0.58077(10) 0.0468(3) Uani 1 1 d . . . . .
F2 F 0.54780(5) 0.92614(9) 0.65022(10) 0.0465(3) Uani 1 1 d . . . . .
O1 O 0.72711(6) 0.71916(13) 0.17850(13) 0.0498(3) Uani 1 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
C1 C6 1.377(2) . ?
C1 C2 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(2) . ?
C2 C9 1.476(2) . ?
C3 C4 1.391(2) . ?
C3 H2 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H3 0.9500 . ?
C5 O1 1.3686(18) . ?
C5 C6 1.390(2) . ?
C6 H4 0.9500 . ?
C7 O1 1.429(2) . ?
C7 H5 0.9800 . ?
C7 H6 0.9800 . ?
C7 H7 0.9800 . ?
C8 C9 1.343(2) . ?
C8 C8 1.463(3) 2_656 ?
C8 H8 0.9500 . ?
C9 C10 1.5077(19) . ?
C10 F2 1.3639(15) . ?
C10 F1 1.3706(17) . ?
C10 C10 1.528(3) 2_656 ?

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
C6 C1 C2 121.13(13) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 117.41(13) . . ?
C3 C2 C9 120.56(13) . . ?
C1 C2 C9 122.02(13) . . ?
C2 C3 C4 121.92(14) . . ?
C2 C3 H2 119.0 . . ?
C4 C3 H2 119.0 . . ?
C5 C4 C3 119.42(14) . . ?
C5 C4 H3 120.3 . . ?
C3 C4 H3 120.3 . . ?
O1 C5 C4 125.03(14) . . ?
O1 C5 C6 115.44(14) . . ?
C4 C5 C6 119.52(14) . . ?
C1 C6 C5 120.51(14) . . ?
C1 C6 H4 119.7 . . ?
C5 C6 H4 119.7 . . ?
O1 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
O1 C7 H7 109.5 . . ?
H5 C7 H7 109.5 . . ?
H6 C7 H7 109.5 . . ?
C9 C8 C8 123.57(9) . 2_656 ?
C9 C8 H8 118.2 . . ?
C8 C8 H8 118.2 2_656 . ?
C8 C9 C2 126.13(13) . . ?
C8 C9 C10 114.90(13) . . ?
C2 C9 C10 118.92(12) . . ?
F2 C10 F1 105.59(11) . . ?
F2 C10 C9 112.30(11) . . ?
F1 C10 C9 109.92(12) . . ?
F2 C10 C10 107.13(10) . 2_656 ?
F1 C10 C10 107.33(14) . 2_656 ?
C9 C10 C10 114.09(9) . 2_656 ?
C5 O1 C7 117.81(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.4(2) . . . . ?
C6 C1 C2 C9 177.77(14) . . . . ?
C1 C2 C3 C4 2.2(2) . . . . ?
C9 C2 C3 C4 -177.05(15) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 O1 178.58(15) . . . . ?
C3 C4 C5 C6 -2.3(2) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
O1 C5 C6 C1 -177.76(14) . . . . ?
C4 C5 C6 C1 3.0(2) . . . . ?
C8 C8 C9 C2 179.76(17) 2_656 . . . ?
C8 C8 C9 C10 -2.8(3) 2_656 . . . ?
C3 C2 C9 C8 -34.4(2) . . . . ?
C1 C2 C9 C8 146.44(16) . . . . ?
C3 C2 C9 C10 148.30(14) . . . . ?
C1 C2 C9 C10 -30.9(2) . . . . ?
C8 C9 C10 F2 153.19(13) . . . . ?
C2 C9 C10 F2 -29.20(18) . . . . ?
C8 C9 C10 F1 -89.58(15) . . . . ?
C2 C9 C10 F1 88.03(15) . . . . ?
C8 C9 C10 C10 31.0(2) . . . 2_656 ?
C2 C9 C10 C10 -151.36(14) . . . 2_656 ?
C4 C5 O1 C7 -7.2(2) . . . . ?
C6 C5 O1 C7 173.62(15) . . . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_exp_445
_database_code_depnum_ccdc_archive 'CCDC 2144836'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2021-05-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 F7'
_chemical_formula_sum            'C19 H11 F7'
_chemical_formula_weight         372.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H11F7
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5391(2)
_cell_length_b                   8.9883(3)
_cell_length_c                   14.4828(5)
_cell_angle_alpha                94.851(3)
_cell_angle_beta                 94.118(3)
_cell_angle_gamma                109.620(3)
_cell_volume                     794.37(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5408
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.5870
_cell_measurement_theta_min      2.3780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 2 -1 0.1940
-1 12 -1 0.2328
8 1 0 0.1775
0 -12 1 0.2460
-8 -2 6 0.2344
0 0 -20 0.0851
8 2 -5 0.2056
1 0 20 0.0874
7 -5 -14 0.2295
-9 2 9 0.1861
9 -3 1 0.2106

_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_min          0.183
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8.9784 1.8816 -0.6532 0.3318 -0.0003 0.9434
-0.5759 12.1546 -0.9680 0.8895 0.0012 -0.4569
8.1994 1.4364 0.3537 -0.0754 0.0006 -0.9972
0.1319 -11.9673 0.9285 -0.8663 -0.0012 0.4995
-7.8195 -2.3784 5.8673 0.0003 -0.3008 0.9537
-0.2105 -0.0229 -20.1656 -0.0010 0.9873 0.1587
7.8595 2.3892 -5.2345 -0.0003 0.2699 -0.9629
0.5921 0.1387 19.9998 0.0010 -0.9785 -0.2060
7.0000 -5.0000 -14.0000 -0.5165 0.7239 -0.4856
-9.0000 2.0000 9.0000 0.3427 -0.4737 0.8766
9.0000 -3.0000 1.0000 -0.4129 -0.0125 -0.8995

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11601
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.422
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  27.00   0.25    0.78    --    5.00  76.00-180.00  136
  2  ω    -52.00  -4.00   0.25    0.78    --  -11.60  76.00  90.00  192
  3  ω    -47.00  21.00   0.25    0.78    --  -11.60  76.00 -30.00  272
  4  ω     42.00  75.00   0.25    0.78    --  -11.60  76.00 -30.00  132
  5  ω    -40.00  62.00   0.25    0.78    --  -11.60  57.00 -60.00  408
  6  ω    -47.00  39.00   0.25    0.78    --  -11.60  57.00-150.00  344
  7  ω   -100.00  56.00   0.25    0.78    --  -11.60  19.00 120.00  624
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218424000
_diffrn_orient_matrix_UB_12      0.0721654000
_diffrn_orient_matrix_UB_13      0.0001966000
_diffrn_orient_matrix_UB_21      0.0028295000
_diffrn_orient_matrix_UB_22      -0.0036659000
_diffrn_orient_matrix_UB_23      -0.0489864000
_diffrn_orient_matrix_UB_31      -0.1137051000
_diffrn_orient_matrix_UB_32      -0.0435047000
_diffrn_orient_matrix_UB_33      -0.0066323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2803
_reflns_number_total             3629
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1210
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(F5A)=Sof(F7A)=Sof(F6A)=1-FVAR(1)
 Sof(F5)=Sof(F6)=Sof(F7)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F001 F -0.00824(13) 0.44024(11) 0.64486(6) 0.0618(3) Uani 1 1 d . . . . .
F002 F 0.29022(16) 0.64012(11) 0.64525(6) 0.0640(3) Uani 1 1 d . . . . .
F003 F 0.12951(16) 0.67681(12) 0.79507(7) 0.0721(3) Uani 1 1 d . . . . .
F004 F 0.03629(14) 0.42974(12) 0.81892(6) 0.0703(3) Uani 1 1 d . . . . .
C005 C 0.3272(2) 0.39385(16) 0.66356(9) 0.0452(3) Uani 1 1 d . . . . .
C006 C 0.2835(2) 0.29836(17) 0.57138(9) 0.0459(3) Uani 1 1 d . . . . .
C007 C 0.4083(2) 0.57992(17) 0.84789(9) 0.0467(3) Uani 1 1 d . . . . .
C008 C 0.4611(2) 0.68571(17) 0.93626(9) 0.0496(3) Uani 1 1 d . . . . .
C009 C 0.2024(2) 0.50305(17) 0.68415(9) 0.0473(3) Uani 1 1 d . . . . .
C00A C 0.5333(2) 0.49961(18) 0.81730(10) 0.0520(3) Uani 1 1 d . . . . .
H00A H 0.659620 0.508851 0.854753 0.062 Uiso 1 1 calc R U . . .
C00B C 0.2211(2) 0.12164(18) 0.39815(10) 0.0504(3) Uani 1 1 d . . . . .
C00C C 0.1979(2) 0.55026(17) 0.78840(10) 0.0497(3) Uani 1 1 d . . . . .
C00D C 0.4842(2) 0.39866(18) 0.72907(10) 0.0512(3) Uani 1 1 d . . . . .
H00D H 0.566586 0.333825 0.717627 0.061 Uiso 1 1 calc R U . . .
C00E C 0.2755(2) 0.06235(18) 0.47714(10) 0.0550(4) Uani 1 1 d . . . . .
H00E H 0.290959 -0.037063 0.472659 0.066 Uiso 1 1 calc R U . . .
C00F C 0.2229(3) 0.35485(19) 0.49099(10) 0.0559(4) Uani 1 1 d . . . . .
H00F H 0.202417 0.452608 0.495184 0.067 Uiso 1 1 calc R U . . .
C00G C 0.3070(2) 0.15043(18) 0.56308(10) 0.0523(3) Uani 1 1 d . . . . .
H00G H 0.344612 0.109874 0.616172 0.063 Uiso 1 1 calc R U . . .
C00H C 0.1929(3) 0.26678(19) 0.40509(10) 0.0575(4) Uani 1 1 d . . . . .
H00H H 0.153563 0.305859 0.351737 0.069 Uiso 1 1 calc R U . . .
C00I C 0.6776(3) 0.7692(2) 0.96937(11) 0.0605(4) Uani 1 1 d . . . . .
H00I H 0.787718 0.757915 0.935233 0.073 Uiso 1 1 calc R U . . .
C00J C 0.3003(3) 0.7059(2) 0.98895(11) 0.0589(4) Uani 1 1 d . . . . .
H00J H 0.153860 0.650674 0.968760 0.071 Uiso 1 1 calc R U . . .
C00K C 0.3572(3) 0.8076(2) 1.07115(11) 0.0688(4) Uani 1 1 d . . . . .
H00K H 0.248438 0.820814 1.105460 0.083 Uiso 1 1 calc R U . . .
C00L C 0.1935(3) 0.0297(2) 0.30442(11) 0.0643(4) Uani 1 1 d . . . . .
C00M C 0.7323(3) 0.8685(2) 1.05179(12) 0.0718(5) Uani 1 1 d . . . . .
H00M H 0.878446 0.922111 1.073313 0.086 Uiso 1 1 calc R U . . .
C00N C 0.5716(3) 0.8887(2) 1.10248(11) 0.0711(5) Uani 1 1 d . . . . .
H00N H 0.608495 0.957137 1.157681 0.085 Uiso 1 1 calc R U . . .
F5 F 0.2615(14) 0.1147(4) 0.2394(2) 0.110(2) Uani 0.536(9) 1 d . . P A 1
F6 F 0.2816(17) -0.0812(11) 0.3016(3) 0.147(4) Uani 0.536(9) 1 d . . P A 1
F7 F -0.0120(6) -0.0507(9) 0.2737(3) 0.115(2) Uani 0.536(9) 1 d . . P A 1
F5A F 0.3814(9) 0.0662(10) 0.2696(6) 0.132(3) Uani 0.464(9) 1 d . . P A 2
F7A F 0.061(2) 0.0585(14) 0.2455(5) 0.175(5) Uani 0.464(9) 1 d . . P A 2
F6A F 0.1382(15) -0.1162(4) 0.3064(3) 0.117(3) Uani 0.464(9) 1 d . . P A 2


_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
F001 C009 1.3605(15) . ?
F002 C009 1.3615(17) . ?
F003 C00C 1.3536(16) . ?
F004 C00C 1.3656(17) . ?
C005 C006 1.4790(17) . ?
C005 C009 1.4973(18) . ?
C005 C00D 1.3337(19) . ?
C006 C00F 1.393(2) . ?
C006 C00G 1.385(2) . ?
C007 C008 1.4737(18) . ?
C007 C00A 1.3344(18) . ?
C007 C00C 1.5002(19) . ?
C008 C00I 1.388(2) . ?
C008 C00J 1.393(2) . ?
C009 C00C 1.5385(19) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.4521(19) . ?
C00B C00E 1.375(2) . ?
C00B C00H 1.374(2) . ?
C00B C00L 1.494(2) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00G 1.3803(19) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.381(2) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00M 1.376(2) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.384(2) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.367(3) . ?
C00L F5 1.273(3) . ?
C00L F6 1.307(4) . ?
C00L F7 1.317(3) . ?
C00L F5A 1.311(4) . ?
C00L F7A 1.275(4) . ?
C00L F6A 1.242(5) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.376(3) . ?
C00N H00N 0.9300 . ?

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
C006 C005 C009 119.42(11) . . ?
C00D C005 C006 124.09(12) . . ?
C00D C005 C009 116.30(12) . . ?
C00F C006 C005 121.54(12) . . ?
C00G C006 C005 120.11(12) . . ?
C00G C006 C00F 118.34(12) . . ?
C008 C007 C00C 120.30(11) . . ?
C00A C007 C008 123.96(12) . . ?
C00A C007 C00C 115.67(12) . . ?
C00I C008 C007 119.78(12) . . ?
C00I C008 C00J 117.92(13) . . ?
C00J C008 C007 122.30(13) . . ?
F001 C009 F002 105.24(10) . . ?
F001 C009 C005 111.83(11) . . ?
F001 C009 C00C 107.42(10) . . ?
F002 C009 C005 109.83(11) . . ?
F002 C009 C00C 107.07(11) . . ?
C005 C009 C00C 114.91(11) . . ?
C007 C00A H00A 118.0 . . ?
C007 C00A C00D 123.95(12) . . ?
C00D C00A H00A 118.0 . . ?
C00E C00B C00L 120.48(14) . . ?
C00H C00B C00E 119.96(13) . . ?
C00H C00B C00L 119.56(14) . . ?
F003 C00C F004 105.31(11) . . ?
F003 C00C C007 112.62(12) . . ?
F003 C00C C009 107.23(11) . . ?
F004 C00C C007 109.27(12) . . ?
F004 C00C C009 107.07(11) . . ?
C007 C00C C009 114.78(10) . . ?
C005 C00D C00A 123.57(12) . . ?
C005 C00D H00D 118.2 . . ?
C00A C00D H00D 118.2 . . ?
C00B C00E H00E 120.0 . . ?
C00B C00E C00G 119.98(14) . . ?
C00G C00E H00E 120.0 . . ?
C006 C00F H00F 119.8 . . ?
C00H C00F C006 120.49(13) . . ?
C00H C00F H00F 119.8 . . ?
C006 C00G H00G 119.5 . . ?
C00E C00G C006 120.94(13) . . ?
C00E C00G H00G 119.5 . . ?
C00B C00H C00F 120.25(14) . . ?
C00B C00H H00H 119.9 . . ?
C00F C00H H00H 119.9 . . ?
C008 C00I H00I 119.4 . . ?
C00M C00I C008 121.19(15) . . ?
C00M C00I H00I 119.4 . . ?
C008 C00J H00J 119.8 . . ?
C00K C00J C008 120.38(15) . . ?
C00K C00J H00J 119.8 . . ?
C00J C00K H00K 119.6 . . ?
C00N C00K C00J 120.74(15) . . ?
C00N C00K H00K 119.6 . . ?
F5 C00L C00B 114.5(2) . . ?
F5 C00L F6 107.5(3) . . ?
F5 C00L F7 103.2(3) . . ?
F6 C00L C00B 114.6(2) . . ?
F6 C00L F7 102.4(4) . . ?
F7 C00L C00B 113.2(2) . . ?
F5A C00L C00B 110.0(2) . . ?
F7A C00L C00B 113.2(2) . . ?
F7A C00L F5A 106.7(5) . . ?
F6A C00L C00B 113.8(2) . . ?
F6A C00L F5A 103.5(4) . . ?
F6A C00L F7A 109.0(5) . . ?
C00I C00M H00M 119.9 . . ?
C00I C00M C00N 120.22(17) . . ?
C00N C00M H00M 119.9 . . ?
C00K C00N C00M 119.54(15) . . ?
C00K C00N H00N 120.2 . . ?
C00M C00N H00N 120.2 . . ?

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
F001 C009 C00C F003 -70.00(14) . . . . ?
F001 C009 C00C F004 42.62(14) . . . . ?
F001 C009 C00C C007 164.08(11) . . . . ?
F002 C009 C00C F003 42.62(13) . . . . ?
F002 C009 C00C F004 155.23(10) . . . . ?
F002 C009 C00C C007 -83.30(14) . . . . ?
C005 C006 C00F C00H 176.93(13) . . . . ?
C005 C006 C00G C00E -177.39(13) . . . . ?
C005 C009 C00C F003 164.88(11) . . . . ?
C005 C009 C00C F004 -82.50(13) . . . . ?
C005 C009 C00C C007 38.96(17) . . . . ?
C006 C005 C009 F001 36.63(17) . . . . ?
C006 C005 C009 F002 -79.82(15) . . . . ?
C006 C005 C009 C00C 159.42(12) . . . . ?
C006 C005 C00D C00A 176.46(14) . . . . ?
C006 C00F C00H C00B 0.5(2) . . . . ?
C007 C008 C00I C00M -179.77(15) . . . . ?
C007 C008 C00J C00K -179.42(15) . . . . ?
C007 C00A C00D C005 10.2(2) . . . . ?
C008 C007 C00A C00D -178.31(14) . . . . ?
C008 C007 C00C F003 31.44(18) . . . . ?
C008 C007 C00C F004 -85.22(15) . . . . ?
C008 C007 C00C C009 154.52(13) . . . . ?
C008 C00I C00M C00N -1.1(3) . . . . ?
C008 C00J C00K C00N -0.6(3) . . . . ?
C009 C005 C006 C00F 32.57(19) . . . . ?
C009 C005 C006 C00G -148.82(13) . . . . ?
C009 C005 C00D C00A 1.4(2) . . . . ?
C00A C007 C008 C00I 32.2(2) . . . . ?
C00A C007 C008 C00J -147.85(16) . . . . ?
C00A C007 C00C F003 -151.51(13) . . . . ?
C00A C007 C00C F004 91.83(15) . . . . ?
C00A C007 C00C C009 -28.43(19) . . . . ?
C00B C00E C00G C006 0.4(2) . . . . ?
C00C C007 C008 C00I -151.06(14) . . . . ?
C00C C007 C008 C00J 28.9(2) . . . . ?
C00C C007 C00A C00D 4.8(2) . . . . ?
C00D C005 C006 C00F -142.35(16) . . . . ?
C00D C005 C006 C00G 36.3(2) . . . . ?
C00D C005 C009 F001 -148.05(13) . . . . ?
C00D C005 C009 F002 95.49(15) . . . . ?
C00D C005 C009 C00C -25.27(18) . . . . ?
C00E C00B C00H C00F 1.2(2) . . . . ?
C00E C00B C00L F5 -143.1(5) . . . . ?
C00E C00B C00L F6 -18.1(6) . . . . ?
C00E C00B C00L F7 98.9(5) . . . . ?
C00E C00B C00L F5A -88.6(6) . . . . ?
C00E C00B C00L F7A 152.1(8) . . . . ?
C00E C00B C00L F6A 26.9(5) . . . . ?
C00F C006 C00G C00E 1.3(2) . . . . ?
C00G C006 C00F C00H -1.7(2) . . . . ?
C00H C00B C00E C00G -1.6(2) . . . . ?
C00H C00B C00L F5 36.5(5) . . . . ?
C00H C00B C00L F6 161.5(6) . . . . ?
C00H C00B C00L F7 -81.5(5) . . . . ?
C00H C00B C00L F5A 91.0(6) . . . . ?
C00H C00B C00L F7A -28.3(9) . . . . ?
C00H C00B C00L F6A -153.4(5) . . . . ?
C00I C008 C00J C00K 0.6(2) . . . . ?
C00I C00M C00N C00K 1.0(3) . . . . ?
C00J C008 C00I C00M 0.2(2) . . . . ?
C00J C00K C00N C00M -0.2(3) . . . . ?
C00L C00B C00E C00G 178.03(14) . . . . ?
C00L C00B C00H C00F -178.47(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.473
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 2144837'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 F4 O'
_chemical_formula_weight         334.30

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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.0280(5)
_cell_length_b                   35.5954(16)
_cell_length_c                   9.5477(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3068.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5234
_cell_measurement_theta_min      2.273
_cell_measurement_theta_max      29.17

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.935
_oxdiff_exptl_absorpt_empirical_full_max 1.1
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17244
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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             2857
_reflns_number_gt                2178
_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 ver. 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Yadokari-XG
_computing_publication_material  Yadokari-XG
_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)+(0.1000P)²] 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         2857
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
C1 C 1.2909(2) 0.26264(6) 0.56501(19) 0.0524(6) Uani 1 1 d . . . . .
H1 H 1.3693 0.2449 0.5625 0.063 Uiso 1 1 calc R U . . .
C2 C 1.1763(2) 0.25828(6) 0.6579(2) 0.0552(5) Uani 1 1 d . . . . .
H2 H 1.1757 0.2375 0.7201 0.066 Uiso 1 1 calc R U . . .
C3 C 1.0617(2) 0.28396(5) 0.66147(19) 0.0460(5) Uani 1 1 d . . . . .
H3 H 0.9835 0.2808 0.7270 0.055 Uiso 1 1 calc R U . . .
C4 C 1.05954(19) 0.31446(5) 0.57027(17) 0.0355(4) Uani 1 1 d . . . . .
C5 C 1.1769(2) 0.31850(5) 0.47682(19) 0.0417(5) Uani 1 1 d . . . . .
H4 H 1.1781 0.3391 0.4133 0.050 Uiso 1 1 calc R U . . .
C6 C 1.2914(2) 0.29285(6) 0.4759(2) 0.0495(5) Uani 1 1 d . . . . .
H5 H 1.3717 0.2961 0.4127 0.059 Uiso 1 1 calc R U . . .
C7 C 0.93370(19) 0.34076(5) 0.57329(17) 0.0338(4) Uani 1 1 d . . . . .
C8 C 0.86176(19) 0.35169(5) 0.68884(17) 0.0392(4) Uani 1 1 d . . . . .
H10 H 0.8945 0.3422 0.7765 0.047 Uiso 1 1 calc R U . . .
C9 C 0.73657(19) 0.37728(5) 0.68786(17) 0.0402(4) Uani 1 1 d . . . . .
H11 H 0.7050 0.3877 0.7744 0.048 Uiso 1 1 calc R U . . .
C10 C 0.66308(18) 0.38694(5) 0.57104(17) 0.0339(4) Uani 1 1 d . . . . .
C11 C 0.7162(2) 0.36796(5) 0.43962(16) 0.0362(4) Uani 1 1 d . . . . .
C12 C 0.8798(2) 0.35797(5) 0.43962(16) 0.0372(4) Uani 1 1 d . . . . .
C13 C 0.53581(19) 0.41262(5) 0.56474(16) 0.0343(4) Uani 1 1 d . . . . .
C14 C 0.5250(2) 0.44277(5) 0.6557(2) 0.0469(5) Uani 1 1 d . . . . .
H6 H 0.6000 0.4462 0.7244 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4086(2) 0.46813(5) 0.6502(2) 0.0494(5) Uani 1 1 d . . . . .
H7 H 0.4043 0.4886 0.7140 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2990(2) 0.46332(5) 0.55111(19) 0.0414(5) Uani 1 1 d . . . . .
C17 C 0.3046(2) 0.43266(5) 0.46165(19) 0.0428(5) Uani 1 1 d . . . . .
H8 H 0.2274 0.4287 0.3957 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4216(2) 0.40790(5) 0.46806(18) 0.0389(4) Uani 1 1 d . . . . .
H9 H 0.4246 0.3872 0.4053 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1786(3) 0.52076(6) 0.6103(3) 0.0657(7) Uani 1 1 d . . . . .
H12 H 0.1745 0.5151 0.7107 0.099 Uiso 1 1 calc R U . . .
H13 H 0.0914 0.5355 0.5836 0.099 Uiso 1 1 calc R U . . .
H14 H 0.2685 0.5352 0.5899 0.099 Uiso 1 1 calc R U . . .
O1 O 0.18062(15) 0.48663(4) 0.53296(16) 0.0558(4) Uani 1 1 d . . . . .
F1 F 0.95666(12) 0.39025(3) 0.41279(12) 0.0534(3) Uani 1 1 d . . . . .
F2 F 0.90454(12) 0.33532(3) 0.32731(10) 0.0531(4) Uani 1 1 d . . . . .
F3 F 0.63850(13) 0.33551(3) 0.41949(11) 0.0521(3) Uani 1 1 d . . . . .
F4 F 0.68973(12) 0.38919(3) 0.32390(10) 0.0521(3) Uani 1 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
C1 C6 1.371(3) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 C7 1.472(2) . ?
C5 C6 1.380(3) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 C8 1.338(2) . ?
C7 C12 1.497(2) . ?
C8 C9 1.452(3) . ?
C8 H10 0.9500 . ?
C9 C10 1.343(2) . ?
C9 H11 0.9500 . ?
C10 C13 1.469(2) . ?
C10 C11 1.504(2) . ?
C11 F4 1.3597(19) . ?
C11 F3 1.365(2) . ?
C11 C12 1.519(3) . ?
C12 F2 1.3600(19) . ?
C12 F1 1.367(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.386(3) . ?
C14 H6 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H7 0.9500 . ?
C16 O1 1.364(2) . ?
C16 C17 1.387(3) . ?
C17 C18 1.377(3) . ?
C17 H8 0.9500 . ?
C18 H9 0.9500 . ?
C19 O1 1.422(3) . ?
C19 H12 0.9800 . ?
C19 H13 0.9800 . ?
C19 H14 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
C6 C1 C2 119.51(18) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.43(19) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.77(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.07(17) . . ?
C3 C4 C7 119.65(16) . . ?
C5 C4 C7 122.28(16) . . ?
C6 C5 C4 120.41(18) . . ?
C6 C5 H4 119.8 . . ?
C4 C5 H4 119.8 . . ?
C1 C6 C5 120.81(18) . . ?
C1 C6 H5 119.6 . . ?
C5 C6 H5 119.6 . . ?
C8 C7 C4 125.14(15) . . ?
C8 C7 C12 115.22(16) . . ?
C4 C7 C12 119.63(14) . . ?
C7 C8 C9 123.72(15) . . ?
C7 C8 H10 118.1 . . ?
C9 C8 H10 118.1 . . ?
C10 C9 C8 123.43(15) . . ?
C10 C9 H11 118.3 . . ?
C8 C9 H11 118.3 . . ?
C9 C10 C13 125.44(15) . . ?
C9 C10 C11 114.87(16) . . ?
C13 C10 C11 119.64(14) . . ?
F4 C11 F3 105.41(13) . . ?
F4 C11 C10 111.87(15) . . ?
F3 C11 C10 109.52(14) . . ?
F4 C11 C12 107.50(13) . . ?
F3 C11 C12 107.54(15) . . ?
C10 C11 C12 114.52(14) . . ?
F2 C12 F1 105.49(13) . . ?
F2 C12 C7 112.10(15) . . ?
F1 C12 C7 109.80(15) . . ?
F2 C12 C11 107.36(14) . . ?
F1 C12 C11 107.28(15) . . ?
C7 C12 C11 114.33(14) . . ?
C14 C13 C18 117.20(16) . . ?
C14 C13 C10 120.77(15) . . ?
C18 C13 C10 122.03(15) . . ?
C13 C14 C15 122.30(17) . . ?
C13 C14 H6 118.9 . . ?
C15 C14 H6 118.9 . . ?
C16 C15 C14 119.28(17) . . ?
C16 C15 H7 120.4 . . ?
C14 C15 H7 120.4 . . ?
O1 C16 C15 125.01(17) . . ?
O1 C16 C17 115.42(16) . . ?
C15 C16 C17 119.58(17) . . ?
C18 C17 C16 120.30(16) . . ?
C18 C17 H8 119.9 . . ?
C16 C17 H8 119.9 . . ?
C17 C18 C13 121.30(16) . . ?
C17 C18 H9 119.3 . . ?
C13 C18 H9 119.3 . . ?
O1 C19 H12 109.5 . . ?
O1 C19 H13 109.5 . . ?
H12 C19 H13 109.5 . . ?
O1 C19 H14 109.5 . . ?
H12 C19 H14 109.5 . . ?
H13 C19 H14 109.5 . . ?
C16 O1 C19 117.64(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C7 178.05(17) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C7 C4 C5 C6 -178.87(16) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C3 C4 C7 C8 37.1(3) . . . . ?
C5 C4 C7 C8 -144.12(19) . . . . ?
C3 C4 C7 C12 -144.18(17) . . . . ?
C5 C4 C7 C12 34.6(2) . . . . ?
C4 C7 C8 C9 -179.08(16) . . . . ?
C12 C7 C8 C9 2.2(3) . . . . ?
C7 C8 C9 C10 13.0(3) . . . . ?
C8 C9 C10 C13 179.88(16) . . . . ?
C8 C9 C10 C11 2.4(3) . . . . ?
C9 C10 C11 F4 -152.60(15) . . . . ?
C13 C10 C11 F4 29.7(2) . . . . ?
C9 C10 C11 F3 90.90(18) . . . . ?
C13 C10 C11 F3 -86.76(18) . . . . ?
C9 C10 C11 C12 -30.0(2) . . . . ?
C13 C10 C11 C12 152.37(15) . . . . ?
C8 C7 C12 F2 -152.27(15) . . . . ?
C4 C7 C12 F2 28.9(2) . . . . ?
C8 C7 C12 F1 90.82(19) . . . . ?
C4 C7 C12 F1 -88.00(18) . . . . ?
C8 C7 C12 C11 -29.8(2) . . . . ?
C4 C7 C12 C11 151.39(15) . . . . ?
F4 C11 C12 F2 -65.87(18) . . . . ?
F3 C11 C12 F2 47.21(17) . . . . ?
C10 C11 C12 F2 169.17(14) . . . . ?
F4 C11 C12 F1 47.11(17) . . . . ?
F3 C11 C12 F1 160.19(13) . . . . ?
C10 C11 C12 F1 -77.85(17) . . . . ?
F4 C11 C12 C7 169.11(14) . . . . ?
F3 C11 C12 C7 -77.81(17) . . . . ?
C10 C11 C12 C7 44.1(2) . . . . ?
C9 C10 C13 C14 33.4(3) . . . . ?
C11 C10 C13 C14 -149.23(17) . . . . ?
C9 C10 C13 C18 -146.69(19) . . . . ?
C11 C10 C13 C18 30.7(2) . . . . ?
C18 C13 C14 C15 -1.7(3) . . . . ?
C10 C13 C14 C15 178.20(17) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 O1 -178.60(18) . . . . ?
C14 C15 C16 C17 1.9(3) . . . . ?
O1 C16 C17 C18 178.10(17) . . . . ?
C15 C16 C17 C18 -2.4(3) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C14 C13 C18 C17 1.3(3) . . . . ?
C10 C13 C18 C17 -178.66(16) . . . . ?
C15 C16 O1 C19 7.8(3) . . . . ?
C17 C16 O1 C19 -172.71(18) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037



