# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_twin_1a
_database_code_depnum_ccdc_archive 'CCDC 2004379'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_audit_creation_date             2019-11-26
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 F8 O2'
_chemical_formula_sum            'C12 H8 F8 O2'
_chemical_formula_weight         336.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     'Cui 14diMeObenz cyclicperfluoro'
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'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   6.8488(11)
_cell_length_b                   11.665(2)
_cell_length_c                   15.489(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.319(14)
_cell_angle_gamma                90
_cell_volume                     1232.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    893
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.6170
_cell_measurement_theta_min      3.4280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   95.00    --   30.00  54.00 150.00  193
  2  ω    -74.00 119.00   1.00   95.00    --   30.00  54.00  30.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0063068000
_diffrn_orient_matrix_UB_12      -0.0484319000
_diffrn_orient_matrix_UB_13      0.0273185000
_diffrn_orient_matrix_UB_21      0.0787810000
_diffrn_orient_matrix_UB_22      -0.0260777000
_diffrn_orient_matrix_UB_23      -0.0193533000
_diffrn_orient_matrix_UB_31      0.0676364000
_diffrn_orient_matrix_UB_32      0.0260791000
_diffrn_orient_matrix_UB_33      0.0314880000
_diffrn_oxdiff_ac3_digest_frames 
;
013c857432b67a020773a68214c6886bf0003866068
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011d3f8515c2ab83db74fd6e918c835049299b
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1031
_reflns_number_total             1947
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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         0.375
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      0.840
_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)+(0.0840P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.673(2)
 0.327(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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
C1 C 0.2705(5) 0.5618(3) 0.5445(2) 0.0231(9) Uani 1 1 d . . . . .
H1 H 0.283672 0.632479 0.574922 0.028 Uiso 1 1 calc R . . . .
C2 C 0.2922(5) 0.4603(3) 0.5895(2) 0.0213(8) Uani 1 1 d . . . . .
C3 C 0.2734(5) 0.3566(3) 0.5451(2) 0.0204(8) Uani 1 1 d . . . . .
C4 C 0.3065(6) 0.2474(3) 0.5953(2) 0.0247(9) Uani 1 1 d . . . . .
C5 C 0.3261(6) 0.1421(3) 0.5383(2) 0.0271(9) Uani 1 1 d . . . . .
C6 C 0.3479(6) 0.5564(3) 0.7255(3) 0.0310(10) Uani 1 1 d . . . . .
H6A H 0.458008 0.601505 0.707750 0.047 Uiso 1 1 calc GR . . . .
H6B H 0.370583 0.538472 0.787472 0.047 Uiso 1 1 calc GR . . . .
H6C H 0.226381 0.600660 0.714847 0.047 Uiso 1 1 calc GR . . . .
F1 F 0.1611(3) 0.22772(18) 0.64662(14) 0.0348(6) Uani 1 1 d . . . . .
F2 F 0.4753(3) 0.25076(19) 0.64892(15) 0.0347(7) Uani 1 1 d . . . . .
F3 F 0.3105(4) 0.04586(17) 0.58580(14) 0.0363(7) Uani 1 1 d . . . . .
F4 F 0.5047(4) 0.14201(18) 0.50894(15) 0.0354(6) Uani 1 1 d . . . . .
O1 O 0.3312(4) 0.4525(2) 0.67690(16) 0.0284(7) 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 C1 1.382(7) 2_556 ?
C1 C2 1.374(5) . ?
C2 C3 1.391(5) . ?
C2 O1 1.359(4) . ?
C3 C3 1.405(7) 2_556 ?
C3 C4 1.499(5) . ?
C4 C5 1.525(5) . ?
C4 F1 1.350(4) . ?
C4 F2 1.360(4) . ?
C5 C5 1.506(7) 2_556 ?
C5 F3 1.352(4) . ?
C5 F4 1.344(4) . ?
C6 O1 1.426(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1 120.5(2) . 2_556 ?
C1 C2 C3 119.8(3) . . ?
O1 C2 C1 124.4(3) . . ?
O1 C2 C3 115.8(3) . . ?
C2 C3 C3 119.59(19) . 2_556 ?
C2 C3 C4 118.7(3) . . ?
C3 C3 C4 121.71(19) 2_556 . ?
C3 C4 C5 113.7(3) . . ?
F1 C4 C3 111.4(3) . . ?
F1 C4 C5 108.3(3) . . ?
F1 C4 F2 106.1(3) . . ?
F2 C4 C3 111.8(3) . . ?
F2 C4 C5 105.2(3) . . ?
C5 C5 C4 111.4(3) 2_556 . ?
F3 C5 C4 109.8(3) . . ?
F3 C5 C5 110.2(3) . 2_556 ?
F4 C5 C4 109.2(3) . . ?
F4 C5 C5 108.5(4) . 2_556 ?
F4 C5 F3 107.7(3) . . ?
C2 O1 C6 117.9(3) . . ?

_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.701
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.673(2)
2 0.327(2)

_twin_special_details            
;
Component 2 rotated by 179.9575° 
 around [0.00 -0.00 1.00] (reciprocal) or [0.20 0.00 0.98] (direct)
;
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2004381'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_audit_creation_date             2020-04-06
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 F8 O S'
_chemical_formula_sum            'C12 H8 F8 O S'
_chemical_formula_weight         352.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S F'
_chemical_oxdiff_usercomment     'Cui cyclic '
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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.003(3)
_cell_length_b                   7.6340(10)
_cell_length_c                   19.904(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.327(13)
_cell_angle_gamma                90
_cell_volume                     2556.3(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1514
_cell_measurement_temperature    123
_cell_measurement_theta_max      21.6600
_cell_measurement_theta_min      2.8840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
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    1.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_unetI/netI     0.1179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   60.00    --   30.00  54.00-180.00  193
  2  ω     40.00 111.00   1.00   60.00    --   30.00  54.00-180.00   71
  3  ω    -65.00  63.00   1.00   60.00    --   30.00  54.00 -30.00  128
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0411028000
_diffrn_orient_matrix_UB_12      -0.0049982000
_diffrn_orient_matrix_UB_13      -0.0025540000
_diffrn_orient_matrix_UB_21      0.0076225000
_diffrn_orient_matrix_UB_22      0.0692643000
_diffrn_orient_matrix_UB_23      0.0237934000
_diffrn_orient_matrix_UB_31      0.0053045000
_diffrn_orient_matrix_UB_32      -0.0617275000
_diffrn_orient_matrix_UB_33      0.0269380000
_diffrn_oxdiff_ac3_digest_frames 
;
011c4a2db3ef27982ba6849ad22f92e7ec00392c852
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0124b9956a21f9fecab4af9db56184fd386bc8
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2539
_reflns_number_total             5238
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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         0.848
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      0.951
_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)+(0.1110P)²+2.8470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.2440
_refine_special_details          ?
_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:
 C2A(H2A), C3A(H3A), C2B(H2B), C3B(H3B)
2.b Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C7B(H7BA,H7BB,H7BC), C8B(H8BA,H8BB,
 H8BC)
;
_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
C1A C 0.5886(3) 0.2117(7) 0.4957(3) 0.0301(13) Uani 1 1 d . . . . .
C2A C 0.5279(3) 0.2530(7) 0.4439(3) 0.0307(13) Uani 1 1 d . . . . .
H2A H 0.539042 0.254175 0.398470 0.037 Uiso 1 1 calc R . . . .
C3A C 0.4523(4) 0.2925(7) 0.4558(3) 0.0319(14) Uani 1 1 d . . . . .
H3A H 0.412083 0.318270 0.418764 0.038 Uiso 1 1 calc R . . . .
C4A C 0.4343(3) 0.2947(7) 0.5214(3) 0.0281(13) Uani 1 1 d . . . . .
C5A C 0.4955(3) 0.2535(7) 0.5751(3) 0.0280(13) Uani 1 1 d . . . . .
C6A C 0.5707(3) 0.2110(7) 0.5626(3) 0.0283(13) Uani 1 1 d . . . . .
C7A C 0.6852(4) 0.2430(9) 0.3965(3) 0.0448(16) Uani 1 1 d . . . . .
H7AA H 0.650555 0.171597 0.363644 0.067 Uiso 1 1 calc GR . . . .
H7AB H 0.739538 0.240098 0.385486 0.067 Uiso 1 1 calc GR . . . .
H7AC H 0.665934 0.364141 0.394563 0.067 Uiso 1 1 calc GR . . . .
C8A C 0.2967(4) 0.3527(8) 0.4828(3) 0.0430(16) Uani 1 1 d . . . . .
H8AA H 0.292167 0.246967 0.454547 0.064 Uiso 1 1 calc GR . . . .
H8AB H 0.307825 0.453715 0.455277 0.064 Uiso 1 1 calc GR . . . .
H8AC H 0.246641 0.372046 0.500706 0.064 Uiso 1 1 calc GR . . . .
C9A C 0.4743(3) 0.2575(8) 0.6460(3) 0.0308(13) Uani 1 1 d . . . . .
C10A C 0.5450(4) 0.2554(8) 0.7020(3) 0.0342(14) Uani 1 1 d . . . . .
C11A C 0.6074(4) 0.1271(8) 0.6876(3) 0.0353(15) Uani 1 1 d . . . . .
C12A C 0.6352(4) 0.1659(7) 0.6197(3) 0.0322(14) Uani 1 1 d . . . . .
F1A F 0.4272(2) 0.1187(4) 0.65602(15) 0.0393(9) Uani 1 1 d . . . . .
F2A F 0.4320(2) 0.4018(4) 0.65754(15) 0.0396(9) Uani 1 1 d . . . . .
F3A F 0.5219(2) 0.2197(5) 0.76213(15) 0.0449(10) Uani 1 1 d . . . . .
F4A F 0.5785(2) 0.4166(4) 0.70614(16) 0.0421(9) Uani 1 1 d . . . . .
F5A F 0.5748(2) -0.0365(4) 0.68428(16) 0.0407(9) Uani 1 1 d . . . . .
F6A F 0.6690(2) 0.1270(5) 0.73811(16) 0.0452(10) Uani 1 1 d . . . . .
F7A F 0.6771(2) 0.0230(4) 0.60509(16) 0.0392(9) Uani 1 1 d . . . . .
F8A F 0.6892(2) 0.2974(4) 0.63064(17) 0.0415(9) Uani 1 1 d . . . . .
O1A O 0.3603(2) 0.3312(5) 0.53822(17) 0.0312(9) Uani 1 1 d . . . . .
S1A S 0.68450(10) 0.1586(2) 0.47908(8) 0.0412(4) Uani 1 1 d . . . . .
C1B C 0.9632(4) 0.6672(9) 0.6883(3) 0.0442(17) Uani 1 1 d . . . . .
C2B C 1.0425(4) 0.6679(9) 0.7132(3) 0.0438(16) Uani 1 1 d . . . . .
H2B H 1.079984 0.668189 0.682178 0.053 Uiso 1 1 calc R . . . .
C3B C 1.0700(4) 0.6681(9) 0.7825(3) 0.0431(16) Uani 1 1 d . . . . .
H3B H 1.125522 0.666337 0.798207 0.052 Uiso 1 1 calc R . . . .
C4B C 1.0166(4) 0.6710(8) 0.8284(3) 0.0406(16) Uani 1 1 d . . . . .
C5B C 0.9352(4) 0.6796(8) 0.8044(3) 0.0384(15) Uani 1 1 d . . . . .
C6B C 0.9088(4) 0.6717(8) 0.7351(3) 0.0376(15) Uani 1 1 d . . . . .
C7B C 1.0130(6) 0.7091(11) 0.5634(4) 0.073(3) Uani 1 1 d . . . . .
H7BA H 0.998757 0.710871 0.513938 0.109 Uiso 1 1 calc GR . . . .
H7BB H 1.055482 0.623506 0.576117 0.109 Uiso 1 1 calc GR . . . .
H7BC H 1.031338 0.825621 0.579361 0.109 Uiso 1 1 calc GR . . . .
C8B C 1.1224(4) 0.6560(12) 0.9232(4) 0.068(2) Uani 1 1 d . . . . .
H8BA H 1.146910 0.556861 0.902820 0.102 Uiso 1 1 calc GR . . . .
H8BB H 1.130688 0.643471 0.972737 0.102 Uiso 1 1 calc GR . . . .
H8BC H 1.146626 0.765468 0.910727 0.102 Uiso 1 1 calc GR . . . .
C9B C 0.8782(4) 0.6957(9) 0.8549(3) 0.0475(18) Uani 1 1 d . . . . .
C10B C 0.7932(4) 0.7424(10) 0.8253(4) 0.0500(18) Uani 1 1 d . . . . .
C11B C 0.7674(4) 0.6441(9) 0.7612(4) 0.0488(18) Uani 1 1 d . . . . .
C12B C 0.8211(4) 0.6719(9) 0.7090(3) 0.0479(18) Uani 1 1 d . . . . .
F1B F 0.9019(2) 0.8221(6) 0.9021(2) 0.0708(14) Uani 1 1 d . . . . .
F2B F 0.8758(2) 0.5427(6) 0.8904(2) 0.0694(13) Uani 1 1 d . . . . .
F3B F 0.7915(2) 0.9142(6) 0.8095(2) 0.0660(12) Uani 1 1 d . . . . .
F4B F 0.7455(2) 0.7142(7) 0.8710(2) 0.0717(13) Uani 1 1 d . . . . .
F5B F 0.6921(2) 0.6844(6) 0.7361(2) 0.0687(13) Uani 1 1 d . . . . .
F6B F 0.7692(3) 0.4704(5) 0.7768(2) 0.0642(12) Uani 1 1 d . . . . .
F7B F 0.7997(2) 0.8257(5) 0.6770(2) 0.0620(12) Uani 1 1 d . . . . .
F8B F 0.8037(3) 0.5456(6) 0.6609(2) 0.0678(13) Uani 1 1 d . . . . .
O1B O 1.0377(3) 0.6591(7) 0.8986(2) 0.0581(14) Uani 1 1 d . . . . .
S1B S 0.93024(14) 0.6512(3) 0.60049(10) 0.0787(8) 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
C1A C2A 1.385(7) . ?
C1A C6A 1.407(8) . ?
C1A S1A 1.759(6) . ?
C2A C3A 1.375(8) . ?
C3A C4A 1.383(8) . ?
C4A C5A 1.414(7) . ?
C4A O1A 1.377(7) . ?
C5A C6A 1.376(8) . ?
C5A C9A 1.507(8) . ?
C6A C12A 1.501(7) . ?
C7A S1A 1.767(6) . ?
C8A O1A 1.438(6) . ?
C9A C10A 1.516(8) . ?
C9A F1A 1.360(7) . ?
C9A F2A 1.353(7) . ?
C10A C11A 1.502(9) . ?
C10A F3A 1.341(7) . ?
C10A F4A 1.353(7) . ?
C11A C12A 1.524(8) . ?
C11A F5A 1.364(7) . ?
C11A F6A 1.342(6) . ?
C12A F7A 1.358(6) . ?
C12A F8A 1.357(6) . ?
C1B C2B 1.368(9) . ?
C1B C6B 1.405(9) . ?
C1B S1B 1.761(6) . ?
C2B C3B 1.391(8) . ?
C3B C4B 1.378(9) . ?
C4B C5B 1.399(8) . ?
C4B O1B 1.394(7) . ?
C5B C6B 1.389(8) . ?
C5B C9B 1.498(9) . ?
C6B C12B 1.506(9) . ?
C7B S1B 1.737(9) . ?
C8B O1B 1.452(8) . ?
C9B C10B 1.523(9) . ?
C9B F1B 1.366(8) . ?
C9B F2B 1.368(8) . ?
C10B C11B 1.490(10) . ?
C10B F3B 1.348(8) . ?
C10B F4B 1.321(8) . ?
C11B C12B 1.495(10) . ?
C11B F5B 1.341(7) . ?
C11B F6B 1.361(8) . ?
C12B F7B 1.360(7) . ?
C12B F8B 1.361(8) . ?

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
C2A C1A C6A 117.8(5) . . ?
C2A C1A S1A 121.5(4) . . ?
C6A C1A S1A 120.7(4) . . ?
C3A C2A C1A 122.4(5) . . ?
C2A C3A C4A 120.3(5) . . ?
C3A C4A C5A 118.1(5) . . ?
O1A C4A C3A 124.5(5) . . ?
O1A C4A C5A 117.3(5) . . ?
C4A C5A C9A 117.0(5) . . ?
C6A C5A C4A 121.1(5) . . ?
C6A C5A C9A 121.9(5) . . ?
C1A C6A C12A 118.9(5) . . ?
C5A C6A C1A 120.2(5) . . ?
C5A C6A C12A 120.9(5) . . ?
C5A C9A C10A 114.6(5) . . ?
F1A C9A C5A 110.3(4) . . ?
F1A C9A C10A 107.8(4) . . ?
F2A C9A C5A 112.4(4) . . ?
F2A C9A C10A 105.6(4) . . ?
F2A C9A F1A 105.7(5) . . ?
C11A C10A C9A 112.0(5) . . ?
F3A C10A C9A 110.7(5) . . ?
F3A C10A C11A 110.1(5) . . ?
F3A C10A F4A 107.8(4) . . ?
F4A C10A C9A 108.5(4) . . ?
F4A C10A C11A 107.6(5) . . ?
C10A C11A C12A 111.1(5) . . ?
F5A C11A C10A 108.2(5) . . ?
F5A C11A C12A 108.1(4) . . ?
F6A C11A C10A 110.7(4) . . ?
F6A C11A C12A 110.9(5) . . ?
F6A C11A F5A 107.7(4) . . ?
C6A C12A C11A 115.5(5) . . ?
F7A C12A C6A 111.7(4) . . ?
F7A C12A C11A 105.9(4) . . ?
F8A C12A C6A 110.8(5) . . ?
F8A C12A C11A 106.9(4) . . ?
F8A C12A F7A 105.4(5) . . ?
C4A O1A C8A 116.6(4) . . ?
C1A S1A C7A 102.9(3) . . ?
C2B C1B C6B 117.9(6) . . ?
C2B C1B S1B 121.0(6) . . ?
C6B C1B S1B 121.0(5) . . ?
C1B C2B C3B 122.2(6) . . ?
C4B C3B C2B 119.8(6) . . ?
C3B C4B C5B 119.4(6) . . ?
C3B C4B O1B 124.3(5) . . ?
O1B C4B C5B 116.3(6) . . ?
C4B C5B C9B 118.6(5) . . ?
C6B C5B C4B 119.8(6) . . ?
C6B C5B C9B 121.5(6) . . ?
C1B C6B C12B 119.0(5) . . ?
C5B C6B C1B 120.7(6) . . ?
C5B C6B C12B 120.3(6) . . ?
C5B C9B C10B 115.4(5) . . ?
F1B C9B C5B 111.4(6) . . ?
F1B C9B C10B 105.7(6) . . ?
F1B C9B F2B 106.0(5) . . ?
F2B C9B C5B 110.3(6) . . ?
F2B C9B C10B 107.6(6) . . ?
C11B C10B C9B 111.0(6) . . ?
F3B C10B C9B 107.8(6) . . ?
F3B C10B C11B 107.3(6) . . ?
F4B C10B C9B 109.8(6) . . ?
F4B C10B C11B 111.9(6) . . ?
F4B C10B F3B 108.9(6) . . ?
C10B C11B C12B 113.0(6) . . ?
F5B C11B C10B 110.4(6) . . ?
F5B C11B C12B 110.8(6) . . ?
F5B C11B F6B 107.2(5) . . ?
F6B C11B C10B 107.5(6) . . ?
F6B C11B C12B 107.6(6) . . ?
C11B C12B C6B 115.7(5) . . ?
F7B C12B C6B 110.3(5) . . ?
F7B C12B C11B 107.4(6) . . ?
F7B C12B F8B 105.5(5) . . ?
F8B C12B C6B 110.2(6) . . ?
F8B C12B C11B 107.2(6) . . ?
C4B O1B C8B 116.1(5) . . ?
C7B S1B C1B 104.1(4) . . ?

_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 1.133
_oxdiff_exptl_absorpt_empirical_full_min 0.873
####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 2004382'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_audit_creation_date             2020-01-09
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C26 H14 F16 N2)'
_chemical_formula_sum            'C13 H7 F8 N'
_chemical_formula_weight         329.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     'Cui methylindole Cyclicperfluoroalkylation'
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'
N N 0.0061 0.0033 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.1069(9)
_cell_length_b                   6.8506(6)
_cell_length_c                   13.7875(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1237.98(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.1940
_cell_measurement_theta_min      3.2580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
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    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8233
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.955
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   65.00    --   30.00  54.00 -30.00  193
  2  ω    -74.00 119.00   1.00   65.00    --   30.00  54.00 -30.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0055181000
_diffrn_orient_matrix_UB_12      -0.0065695000
_diffrn_orient_matrix_UB_13      0.0510798000
_diffrn_orient_matrix_UB_21      -0.0536812000
_diffrn_orient_matrix_UB_22      -0.0072805000
_diffrn_orient_matrix_UB_23      0.0050021000
_diffrn_orient_matrix_UB_31      0.0034910000
_diffrn_orient_matrix_UB_32      -0.1031355000
_diffrn_orient_matrix_UB_33      -0.0036259000
_diffrn_oxdiff_ac3_digest_frames 
;
01b263afbe41efe93db275c1d0ebd0a7a600386f4cd
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01c50784b16bcf86964afc2c1b772243b53fbc
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1121
_reflns_number_total             1376
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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         0.229
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.032
_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)+(0.0520P)²+0.2960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_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. Uiso/Uaniso restraints and constraints
F8 \\sim C7 \\sim C8 \\sim C10 \\sim C13 \\sim F1 \\sim F4 \\sim F6 \\sim C12
\\sim C11 \\sim F7 \\sim F5 \\sim F2 \\sim F3 \\sim C8 \\sim C7 \\sim C13 \\sim
C8 \\sim C10 \\sim C7 \\sim F7 \\sim C13 \\sim F8 \\sim C13 \\sim C12 \\sim C13
\\sim F1 \\sim C10 \\sim F2 \\sim C10 \\sim C11 \\sim C10 \\sim F6 \\sim C12
\\sim C12 \\sim C11 \\sim F5 \\sim C12 \\sim F4 \\sim C11 \\sim F3 \\sim C11:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F8(0.5) C10(0.5) F1(0.5) H9A(0.5) H9B(0.5) H9C(0.5) F4(0.5)
 F6(0.5) C12(0.5) C11(0.5) F7(0.5) F5(0.5) F2(0.5) F3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
N1 N 0.60207(11) 0.250000 0.38539(10) 0.0225(3) Uani 1 2 d S T P A .
F8 F 0.81408(18) 0.4410(4) 0.34589(17) 0.0398(5) Uani 0.5 1 d . U . A -1
C7 C 0.67945(13) 0.250000 0.53090(12) 0.0196(4) Uani 1 2 d S TU P . .
C8 C 0.69404(13) 0.250000 0.43207(13) 0.0199(4) Uani 1 2 d S TU P A .
C1 C 0.52636(13) 0.250000 0.45527(13) 0.0215(4) Uani 1 2 d S T P . .
C6 C 0.57211(14) 0.250000 0.54772(13) 0.0209(4) Uani 1 2 d S T P . .
C2 C 0.42008(14) 0.250000 0.44328(15) 0.0275(4) Uani 1 2 d S T P . .
H2 H 0.389753 0.250000 0.380692 0.033 Uiso 1 2 calc RS T P . .
C10 C 0.76314(17) 0.238(5) 0.60211(16) 0.025(2) Uani 0.5 1 d . U . A -1
C13 C 0.79529(14) 0.250000 0.38363(13) 0.0280(4) Uani 1 2 d S TU P . .
C5 C 0.51042(16) 0.250000 0.63123(14) 0.0290(4) Uani 1 2 d S T P . .
H5 H 0.539780 0.250000 0.694221 0.035 Uiso 1 2 calc RS T P A .
F1 F 0.74533(16) 0.3621(4) 0.67857(14) 0.0429(5) Uani 0.5 1 d . U . A -1
C3 C 0.36181(15) 0.250000 0.52611(16) 0.0322(5) Uani 1 2 d S T P . .
H3 H 0.289570 0.250000 0.520513 0.039 Uiso 1 2 calc RS T P A .
C9 C 0.58302(16) 0.250000 0.28098(13) 0.0338(5) Uani 1 2 d S T P . .
H9A H 0.526095 0.337933 0.266317 0.051 Uiso 0.5 1 calc GR . . A -1
H9B H 0.565875 0.117469 0.259757 0.051 Uiso 0.5 1 calc GR . . A -1
H9C H 0.644308 0.294598 0.246823 0.051 Uiso 0.5 1 calc GR . . A -1
C4 C 0.40616(16) 0.250000 0.61884(16) 0.0338(5) Uani 1 2 d S T P A .
H4 H 0.363209 0.250000 0.674347 0.041 Uiso 1 2 calc RS T P . .
F4 F 0.86762(14) 0.4967(2) 0.54544(13) 0.0379(4) Uani 0.5 1 d . U . A -1
F6 F 0.88346(13) 0.0124(3) 0.46667(13) 0.0379(4) Uani 0.5 1 d . U . A -1
C12 C 0.88081(18) 0.2085(4) 0.45604(18) 0.0294(10) Uani 0.5 1 d . U . A -1
C11 C 0.86552(19) 0.3003(4) 0.55569(18) 0.0290(8) Uani 0.5 1 d . U . A -1
F7 F 0.80283(18) 0.1347(4) 0.30804(15) 0.0420(6) Uani 0.5 1 d . U . A -1
F5 F 0.97120(10) 0.235(8) 0.41891(11) 0.043(4) Uani 0.5 1 d . U . A -1
F2 F 0.77493(16) 0.0612(3) 0.64272(15) 0.0398(5) Uani 0.5 1 d . U . A -1
F3 F 0.94357(11) 0.264(8) 0.61452(11) 0.039(4) Uani 0.5 1 d . U . 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
N1 C8 1.367(2) . ?
N1 C1 1.383(2) . ?
N1 C9 1.461(2) . ?
F8 C13 1.430(2) . ?
C7 C8 1.376(2) . ?
C7 C6 1.426(2) . ?
C7 C10 1.474(3) . ?
C8 C13 1.486(2) . ?
C1 C6 1.409(3) . ?
C1 C2 1.403(3) . ?
C6 C5 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C10 F1 1.38(2) . ?
C10 C11 1.547(10) . ?
C10 F2 1.34(3) . ?
C13 C12 1.528(3) . ?
C13 F7 1.311(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 H4 0.9500 . ?
F4 C11 1.353(3) . ?
F6 C12 1.351(3) . ?
C12 C11 1.524(4) . ?
C12 F5 1.303(8) . ?
C11 F3 1.329(11) . ?

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 N1 C1 107.74(14) . . ?
C8 N1 C9 127.94(15) . . ?
C1 N1 C9 124.31(15) . . ?
C8 C7 C6 107.35(15) . . ?
C8 C7 C10 123.78(17) . . ?
C6 C7 C10 128.73(18) . . ?
N1 C8 C7 110.12(15) . . ?
N1 C8 C13 125.18(16) . . ?
C7 C8 C13 124.70(16) . . ?
N1 C1 C6 108.97(15) . . ?
N1 C1 C2 129.08(17) . . ?
C2 C1 C6 121.96(17) . . ?
C1 C6 C7 105.83(15) . . ?
C5 C6 C7 134.44(17) . . ?
C5 C6 C1 119.73(17) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.00(18) . . ?
C3 C2 H2 121.5 . . ?
C7 C10 C11 110.7(7) . . ?
F1 C10 C7 110.4(13) . . ?
F1 C10 C11 107.1(16) . . ?
F2 C10 C7 114.5(18) . . ?
F2 C10 F1 104.9(6) . . ?
F2 C10 C11 108.8(11) . . ?
F8 C13 C8 108.51(12) . . ?
F8 C13 C12 106.38(17) . . ?
C8 C13 C12 111.19(16) . . ?
F7 C13 F8 104.4(2) . . ?
F7 C13 C8 115.12(16) . . ?
F7 C13 C12 110.61(17) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 117.96(19) . . ?
C4 C5 H5 121.0 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.78(18) . . ?
C4 C3 H3 119.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 121.57(18) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
F6 C12 C13 105.95(19) . . ?
F6 C12 C11 108.4(2) . . ?
C11 C12 C13 114.6(2) . . ?
F5 C12 C13 112.6(7) . . ?
F5 C12 F6 99(2) . . ?
F5 C12 C11 114.6(13) . . ?
F4 C11 C10 109.6(12) . . ?
F4 C11 C12 108.3(2) . . ?
C12 C11 C10 111.9(7) . . ?
F3 C11 C10 111.3(10) . . ?
F3 C11 F4 104(2) . . ?
F3 C11 C12 111.8(13) . . ?

_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.883
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2004380'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 F8 O2'
_chemical_formula_sum            'C14 H12 F8 O2'
_chemical_formula_weight         364.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     'ono114 Cui 14diethoxybenzene cyclic'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7335(7)
_cell_length_b                   19.260(2)
_cell_length_c                   15.5646(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.317(8)
_cell_angle_gamma                90
_cell_volume                     2909.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.0740
_cell_measurement_theta_min      3.3880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
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    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20021
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.489
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   40.00    --   30.00  54.00  30.00  193
  2  ω    -71.00 111.00   1.00   40.00    --   30.00  54.00-180.00  182
  3  ω    -59.00 -32.00   1.00   40.00    --   30.00  54.00  30.00   27
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0406259000
_diffrn_orient_matrix_UB_12      0.0221616000
_diffrn_orient_matrix_UB_13      -0.0242765000
_diffrn_orient_matrix_UB_21      -0.0172254000
_diffrn_orient_matrix_UB_22      0.0285785000
_diffrn_orient_matrix_UB_23      0.0257668000
_diffrn_orient_matrix_UB_31      0.0582830000
_diffrn_orient_matrix_UB_32      -0.0069766000
_diffrn_orient_matrix_UB_33      0.0288758000
_diffrn_oxdiff_ac3_digest_frames 
;
01468f81c44acc098743bb34c2a6691d8a004024540
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01a45ac8e85e18eec2d1874918b0497129b79a
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3793
_reflns_number_total             5937
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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         0.701
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.041
_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)+(0.0830P)²+1.3320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C9A(H9AA,H9AB), C7B(H7BA,H7BB), C9B(H9BA,H9BB)
2.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C2B(H2B), C3B(H3B)
2.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C10A(H10A,H10B,H10C), C8B(H8BA,H8BB,H8BC), C10B(H10D,
 H10E,H10F)
;
_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
C1A C 0.0661(3) 0.65995(17) 0.8303(2) 0.0335(7) Uani 1 1 d . . . . .
C2A C -0.0679(3) 0.63646(18) 0.8358(2) 0.0358(8) Uani 1 1 d . . . . .
H2A H -0.142728 0.667744 0.825397 0.043 Uiso 1 1 calc R . . . .
C3A C -0.0933(3) 0.56839(18) 0.8563(2) 0.0366(8) Uani 1 1 d . . . . .
H3A H -0.185473 0.553367 0.860801 0.044 Uiso 1 1 calc R . . . .
C4A C 0.0138(3) 0.52167(17) 0.8703(2) 0.0329(7) Uani 1 1 d . . . . .
C5A C 0.1499(3) 0.54408(16) 0.86277(19) 0.0301(7) Uani 1 1 d . . . . .
C6A C 0.1751(3) 0.61383(17) 0.8456(2) 0.0325(7) Uani 1 1 d . . . . .
C7A C -0.0040(4) 0.77857(18) 0.8140(3) 0.0464(9) Uani 1 1 d . . . . .
H7AA H -0.037224 0.779825 0.872522 0.056 Uiso 1 1 calc R . . . .
H7AB H -0.083442 0.768944 0.772169 0.056 Uiso 1 1 calc R . . . .
C8A C 0.0601(5) 0.8463(2) 0.7938(3) 0.0598(11) Uani 1 1 d . . . . .
H8AA H 0.090419 0.844993 0.735143 0.090 Uiso 1 1 calc GR . . . .
H8AB H 0.139625 0.854971 0.834814 0.090 Uiso 1 1 calc GR . . . .
H8AC H -0.007538 0.883634 0.798016 0.090 Uiso 1 1 calc GR . . . .
C9A C -0.1391(3) 0.42746(18) 0.8941(2) 0.0393(8) Uani 1 1 d . . . . .
H9AA H -0.187648 0.428844 0.835922 0.047 Uiso 1 1 calc R . . . .
H9AB H -0.191819 0.455414 0.933652 0.047 Uiso 1 1 calc R . . . .
C10A C -0.1251(4) 0.35432(19) 0.9254(2) 0.0451(9) Uani 1 1 d . . . . .
H10A H -0.070170 0.327712 0.886640 0.068 Uiso 1 1 calc GR . . . .
H10B H -0.216678 0.333353 0.926393 0.068 Uiso 1 1 calc GR . . . .
H10C H -0.079215 0.353905 0.983628 0.068 Uiso 1 1 calc GR . . . .
C11A C 0.3191(3) 0.64211(17) 0.8456(2) 0.0338(7) Uani 1 1 d . . . . .
C12A C 0.4300(3) 0.59070(19) 0.8797(2) 0.0376(8) Uani 1 1 d . . . . .
C13A C 0.4020(3) 0.51834(19) 0.8464(2) 0.0369(8) Uani 1 1 d . . . . .
C14A C 0.2633(3) 0.49134(17) 0.8727(2) 0.0329(7) Uani 1 1 d . . . . .
F1A F 0.33659(19) 0.69980(10) 0.89398(13) 0.0430(5) Uani 1 1 d . . . . .
F2A F 0.34896(19) 0.66049(10) 0.76429(12) 0.0434(5) Uani 1 1 d . . . . .
F3A F 0.43177(19) 0.58952(11) 0.96649(12) 0.0444(5) Uani 1 1 d . . . . .
F4A F 0.55531(18) 0.61222(11) 0.85912(13) 0.0484(5) Uani 1 1 d . . . . .
F5A F 0.50424(18) 0.47498(11) 0.87366(13) 0.0460(5) Uani 1 1 d . . . . .
F6A F 0.39690(18) 0.52021(10) 0.75930(12) 0.0420(5) Uani 1 1 d . . . . .
F7A F 0.28241(18) 0.46781(10) 0.95504(12) 0.0401(5) Uani 1 1 d . . . . .
F8A F 0.23390(19) 0.43427(10) 0.82347(13) 0.0421(5) Uani 1 1 d . . . . .
O1A O 0.0977(2) 0.72603(12) 0.80906(16) 0.0429(6) Uani 1 1 d . . . . .
O2A O -0.0018(2) 0.45404(12) 0.89179(16) 0.0419(6) Uani 1 1 d . . . . .
C1B C 1.0422(3) 0.61114(18) 0.5855(2) 0.0353(7) Uani 1 1 d . . . . .
C2B C 1.1350(3) 0.55796(19) 0.6018(2) 0.0397(8) Uani 1 1 d . . . . .
H2B H 1.230243 0.566330 0.596719 0.048 Uiso 1 1 calc R . . . .
C3B C 1.0926(3) 0.49273(19) 0.6252(2) 0.0374(8) Uani 1 1 d . . . . .
H3B H 1.158735 0.457036 0.637032 0.045 Uiso 1 1 calc R . . . .
C4B C 0.9534(3) 0.47909(18) 0.6317(2) 0.0342(7) Uani 1 1 d . . . . .
C5B C 0.8581(3) 0.53212(17) 0.61426(19) 0.0301(7) Uani 1 1 d . . . . .
C6B C 0.9014(3) 0.59867(17) 0.59347(19) 0.0308(7) Uani 1 1 d . . . . .
C7B C 1.2182(3) 0.6935(2) 0.5573(2) 0.0456(9) Uani 1 1 d . . . . .
H7BA H 1.256623 0.668223 0.509151 0.055 Uiso 1 1 calc R . . . .
H7BB H 1.271913 0.680831 0.611558 0.055 Uiso 1 1 calc R . . . .
C8B C 1.2243(4) 0.7702(2) 0.5426(3) 0.0593(11) Uani 1 1 d . . . . .
H8BA H 1.163928 0.782488 0.491687 0.089 Uiso 1 1 calc GR . . . .
H8BB H 1.319182 0.783744 0.533583 0.089 Uiso 1 1 calc GR . . . .
H8BC H 1.193805 0.794586 0.593096 0.089 Uiso 1 1 calc GR . . . .
C9B C 0.9930(3) 0.36026(18) 0.6742(2) 0.0423(8) Uani 1 1 d . . . . .
H9BA H 1.056789 0.370920 0.725064 0.051 Uiso 1 1 calc R . . . .
H9BB H 1.048055 0.350344 0.624643 0.051 Uiso 1 1 calc R . . . .
C10B C 0.9039(4) 0.29934(19) 0.6922(2) 0.0463(9) Uani 1 1 d . . . . .
H10D H 0.846006 0.287422 0.640049 0.069 Uiso 1 1 calc GR . . . .
H10E H 0.845174 0.311198 0.738528 0.069 Uiso 1 1 calc GR . . . .
H10F H 0.962152 0.259568 0.709844 0.069 Uiso 1 1 calc GR . . . .
C11B C 0.8036(3) 0.65820(18) 0.5783(2) 0.0376(8) Uani 1 1 d . . . . .
C12B C 0.6574(4) 0.6429(2) 0.6036(3) 0.0514(10) Uani 1 1 d . . . . .
C13B C 0.6130(3) 0.57179(19) 0.5799(2) 0.0429(9) Uani 1 1 d . . . . .
C14B C 0.7077(3) 0.51531(17) 0.6186(2) 0.0330(7) Uani 1 1 d . . . . .
F1B F 0.8434(2) 0.71435(11) 0.62688(14) 0.0533(6) Uani 1 1 d . . . . .
F2B F 0.7965(2) 0.67971(11) 0.49566(13) 0.0474(5) Uani 1 1 d . . . . .
F3B F 0.6540(2) 0.64529(13) 0.69212(14) 0.0589(6) Uani 1 1 d . . . . .
F4B F 0.56810(19) 0.68981(11) 0.56741(15) 0.0528(6) Uani 1 1 d . . . . .
F5B F 0.48209(16) 0.56006(10) 0.59985(12) 0.0404(5) Uani 1 1 d . . . . .
F6B F 0.61442(19) 0.56926(12) 0.49011(12) 0.0499(6) Uani 1 1 d . . . . .
F7B F 0.67102(18) 0.45740(10) 0.57377(13) 0.0437(5) Uani 1 1 d . . . . .
F8B F 0.67740(18) 0.50308(11) 0.70076(12) 0.0456(5) Uani 1 1 d . . . . .
O1B O 1.0755(2) 0.67629(13) 0.56217(16) 0.0450(6) Uani 1 1 d . . . . .
O2B O 0.9018(2) 0.41726(13) 0.65504(16) 0.0446(6) 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
C1A C2A 1.389(4) . ?
C1A C6A 1.390(4) . ?
C1A O1A 1.356(4) . ?
C2A C3A 1.376(5) . ?
C3A C4A 1.382(4) . ?
C4A C5A 1.407(4) . ?
C4A O2A 1.356(4) . ?
C5A C6A 1.395(5) . ?
C5A C14A 1.500(4) . ?
C6A C11A 1.504(4) . ?
C7A C8A 1.491(5) . ?
C7A O1A 1.422(4) . ?
C9A C10A 1.493(5) . ?
C9A O2A 1.433(4) . ?
C11A C12A 1.529(5) . ?
C11A F1A 1.345(4) . ?
C11A F2A 1.367(4) . ?
C12A C13A 1.505(5) . ?
C12A F3A 1.350(4) . ?
C12A F4A 1.350(4) . ?
C13A C14A 1.531(4) . ?
C13A F5A 1.343(4) . ?
C13A F6A 1.353(4) . ?
C14A F7A 1.359(3) . ?
C14A F8A 1.358(4) . ?
C1B C2B 1.376(5) . ?
C1B C6B 1.407(4) . ?
C1B O1B 1.352(4) . ?
C2B C3B 1.380(5) . ?
C3B C4B 1.392(4) . ?
C4B C5B 1.392(4) . ?
C4B O2B 1.353(4) . ?
C5B C6B 1.395(5) . ?
C5B C14B 1.506(4) . ?
C6B C11B 1.498(4) . ?
C7B C8B 1.496(6) . ?
C7B O1B 1.435(4) . ?
C9B C10B 1.498(5) . ?
C9B O2B 1.429(4) . ?
C11B C12B 1.534(5) . ?
C11B F1B 1.359(4) . ?
C11B F2B 1.348(4) . ?
C12B C13B 1.474(5) . ?
C12B F3B 1.381(5) . ?
C12B F4B 1.347(4) . ?
C13B C14B 1.520(5) . ?
C13B F5B 1.353(3) . ?
C13B F6B 1.400(4) . ?
C14B F7B 1.350(4) . ?
C14B F8B 1.354(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A C6A 119.3(3) . . ?
O1A C1A C2A 123.5(3) . . ?
O1A C1A C6A 117.2(3) . . ?
C3A C2A C1A 120.7(3) . . ?
C2A C3A C4A 120.7(3) . . ?
C3A C4A C5A 119.4(3) . . ?
O2A C4A C3A 124.5(3) . . ?
O2A C4A C5A 116.0(3) . . ?
C4A C5A C14A 118.3(3) . . ?
C6A C5A C4A 119.4(3) . . ?
C6A C5A C14A 122.2(3) . . ?
C1A C6A C5A 120.4(3) . . ?
C1A C6A C11A 117.9(3) . . ?
C5A C6A C11A 121.7(3) . . ?
O1A C7A C8A 107.9(3) . . ?
O2A C9A C10A 106.4(3) . . ?
C6A C11A C12A 113.5(3) . . ?
F1A C11A C6A 112.2(3) . . ?
F1A C11A C12A 106.5(3) . . ?
F1A C11A F2A 106.1(3) . . ?
F2A C11A C6A 110.9(2) . . ?
F2A C11A C12A 107.2(2) . . ?
C13A C12A C11A 112.1(3) . . ?
F3A C12A C11A 108.3(3) . . ?
F3A C12A C13A 108.5(3) . . ?
F4A C12A C11A 110.2(3) . . ?
F4A C12A C13A 110.2(3) . . ?
F4A C12A F3A 107.4(3) . . ?
C12A C13A C14A 111.3(3) . . ?
F5A C13A C12A 110.9(3) . . ?
F5A C13A C14A 110.6(3) . . ?
F5A C13A F6A 107.7(2) . . ?
F6A C13A C12A 108.2(3) . . ?
F6A C13A C14A 108.1(3) . . ?
C5A C14A C13A 113.6(3) . . ?
F7A C14A C5A 111.7(2) . . ?
F7A C14A C13A 107.7(2) . . ?
F8A C14A C5A 111.6(2) . . ?
F8A C14A C13A 106.1(2) . . ?
F8A C14A F7A 105.7(3) . . ?
C1A O1A C7A 118.9(3) . . ?
C4A O2A C9A 118.1(3) . . ?
C2B C1B C6B 119.1(3) . . ?
O1B C1B C2B 124.9(3) . . ?
O1B C1B C6B 115.9(3) . . ?
C1B C2B C3B 121.4(3) . . ?
C2B C3B C4B 120.2(3) . . ?
C3B C4B C5B 119.1(3) . . ?
O2B C4B C3B 124.7(3) . . ?
O2B C4B C5B 116.3(3) . . ?
C4B C5B C6B 120.7(3) . . ?
C4B C5B C14B 118.0(3) . . ?
C6B C5B C14B 121.3(3) . . ?
C1B C6B C11B 117.9(3) . . ?
C5B C6B C1B 119.4(3) . . ?
C5B C6B C11B 122.7(3) . . ?
O1B C7B C8B 106.6(3) . . ?
O2B C9B C10B 106.3(3) . . ?
C6B C11B C12B 113.8(3) . . ?
F1B C11B C6B 111.7(3) . . ?
F1B C11B C12B 104.0(3) . . ?
F2B C11B C6B 111.8(3) . . ?
F2B C11B C12B 108.8(3) . . ?
F2B C11B F1B 106.1(3) . . ?
C13B C12B C11B 112.0(3) . . ?
F3B C12B C11B 110.0(3) . . ?
F3B C12B C13B 104.6(3) . . ?
F4B C12B C11B 110.2(3) . . ?
F4B C12B C13B 110.5(3) . . ?
F4B C12B F3B 109.4(3) . . ?
C12B C13B C14B 114.1(3) . . ?
F5B C13B C12B 111.1(3) . . ?
F5B C13B C14B 110.1(3) . . ?
F5B C13B F6B 107.6(3) . . ?
F6B C13B C12B 104.9(3) . . ?
F6B C13B C14B 108.6(3) . . ?
C5B C14B C13B 113.0(3) . . ?
F7B C14B C5B 112.0(2) . . ?
F7B C14B C13B 104.9(3) . . ?
F7B C14B F8B 106.1(3) . . ?
F8B C14B C5B 111.2(2) . . ?
F8B C14B C13B 109.3(3) . . ?
C1B O1B C7B 118.7(3) . . ?
C4B O2B C9B 119.6(2) . . ?

_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.802
