# Electronic Supplementary Material (ESI) for ChemComm.
# 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_3bn
_database_code_depnum_ccdc_archive 'CCDC 2131398'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H3 F7'
_chemical_formula_sum            'C12 H3 F7'
_chemical_formula_weight         280.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H3 F7'
_chemical_oxdiff_usercomment     'colourless plate'
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                   7.3590(9)
_cell_length_b                   7.5748(9)
_cell_length_c                   9.8836(10)
_cell_angle_alpha                75.019(9)
_cell_angle_beta                 79.707(9)
_cell_angle_gamma                78.279(10)
_cell_volume                     516.46(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    943
_cell_measurement_temperature    294
_cell_measurement_theta_max      23.5220
_cell_measurement_theta_min      3.6280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 2 0.2455
-1 -5 -2 0.2455
5 0 1 0.3215
-5 0 -1 0.2155
5 -5 -1 0.2829
0 0 1 0.0279
0 0 -1 0.0539
-5 4 0 0.2601

_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.082
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
1.0000 5.0000 2.0000 0.0802 0.2122 -0.4103
-1.0000 -5.0000 -2.0000 -0.0802 -0.2122 0.4103
5.0000 -0.0000 1.0000 -0.1467 -0.4041 -0.2397
-5.0000 0.0000 -1.0000 0.1467 0.4041 0.2397
5.0000 -5.0000 -1.0000 -0.2704 -0.6921 0.1233
-0.0000 0.0000 1.0000 0.0705 -0.0252 -0.0035
0.0000 -0.0000 -1.0000 -0.0705 0.0252 0.0035
-5.0000 4.0000 0.0000 0.2033 0.6496 -0.0486

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.448
_diffrn_reflns_theta_min         3.337
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  14.00   1.00    2.13    --  -10.48 -99.00-150.00   26
  2  ω    -84.00  10.00   1.00    2.13    --  -10.48 -57.00 -60.00   94
  3  ω     -4.00  84.00   1.00    2.13    --   12.36  57.00-150.00   88
  4  ω    -64.00  35.00   1.00    2.13    --   12.36 -77.00  90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0434517000
_diffrn_orient_matrix_UB_12      -0.0034847000
_diffrn_orient_matrix_UB_13      0.0705277000
_diffrn_orient_matrix_UB_21      -0.0757967000
_diffrn_orient_matrix_UB_22      0.0676517000
_diffrn_orient_matrix_UB_23      -0.0251548000
_diffrn_orient_matrix_UB_31      -0.0472468000
_diffrn_orient_matrix_UB_32      -0.0712086000
_diffrn_orient_matrix_UB_33      -0.0034862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1181
_reflns_number_total             2392
_reflns_odcompleteness_completeness 99.81
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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         0.162
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.066
_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)+(0.0531P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1472
_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:
 C12(H12), C10(H10), C11(H11)
;
_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
F5 F 0.4190(2) -0.0361(2) 0.24391(16) 0.0708(5) Uani 1 1 d . . . . .
F6 F 0.0725(2) 0.2294(2) 0.23446(15) 0.0764(6) Uani 1 1 d . . . . .
F1 F 0.4761(2) 0.5618(2) 0.26889(17) 0.0745(5) Uani 1 1 d . . . . .
F7 F -0.2109(2) 0.2194(3) 0.44447(17) 0.0887(6) Uani 1 1 d . . . . .
F4 F 0.7089(3) -0.0313(2) 0.03668(19) 0.0885(6) Uani 1 1 d . . . . .
F2 F 0.7659(3) 0.5642(2) 0.06268(18) 0.0888(6) Uani 1 1 d . . . . .
F3 F 0.8832(3) 0.2693(3) -0.05623(17) 0.0930(6) Uani 1 1 d . . . . .
C6 C 0.4365(3) 0.2628(3) 0.2629(2) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.2798(4) 0.2592(3) 0.3807(2) 0.0456(6) Uani 1 1 d . . . . .
C5 C 0.5021(4) 0.1157(3) 0.1996(2) 0.0519(7) Uani 1 1 d . . . . .
C1 C 0.5311(4) 0.4127(3) 0.2132(2) 0.0499(6) Uani 1 1 d . . . . .
C8 C 0.1046(4) 0.2413(3) 0.3617(2) 0.0517(7) Uani 1 1 d . . . . .
C9 C -0.0413(4) 0.2366(4) 0.4699(3) 0.0592(7) Uani 1 1 d . . . . .
C4 C 0.6499(4) 0.1158(4) 0.0938(3) 0.0573(7) Uani 1 1 d . . . . .
C2 C 0.6801(4) 0.4157(4) 0.1070(3) 0.0576(7) Uani 1 1 d . . . . .
C12 C 0.3035(4) 0.2723(4) 0.5137(3) 0.0565(7) Uani 1 1 d . . . . .
H12 H 0.4205 0.2841 0.5302 0.068 Uiso 1 1 calc R . . . .
C3 C 0.7381(4) 0.2672(4) 0.0477(2) 0.0603(8) Uani 1 1 d . . . . .
C10 C -0.0175(4) 0.2484(4) 0.6004(3) 0.0628(8) Uani 1 1 d . . . . .
H10 H -0.1166 0.2433 0.6736 0.075 Uiso 1 1 calc R . . . .
C11 C 0.1561(4) 0.2681(4) 0.6219(3) 0.0638(8) Uani 1 1 d . . . . .
H11 H 0.1743 0.2787 0.7100 0.077 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
F5 C5 1.349(3) . ?
F6 C8 1.349(3) . ?
F1 C1 1.341(3) . ?
F7 C9 1.354(3) . ?
F4 C4 1.338(3) . ?
F2 C2 1.339(3) . ?
F3 C3 1.342(3) . ?
C6 C7 1.484(3) . ?
C6 C5 1.378(3) . ?
C6 C1 1.388(3) . ?
C7 C8 1.374(3) . ?
C7 C12 1.387(3) . ?
C5 C4 1.368(4) . ?
C1 C2 1.375(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.359(4) . ?
C4 C3 1.367(4) . ?
C2 C3 1.359(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 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
C5 C6 C7 122.5(2) . . ?
C5 C6 C1 115.7(2) . . ?
C1 C6 C7 121.8(2) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 C12 117.3(2) . . ?
C12 C7 C6 121.9(2) . . ?
F5 C5 C6 119.1(2) . . ?
F5 C5 C4 118.1(2) . . ?
C4 C5 C6 122.8(2) . . ?
F1 C1 C6 119.5(2) . . ?
F1 C1 C2 118.0(2) . . ?
C2 C1 C6 122.4(3) . . ?
F6 C8 C7 120.1(2) . . ?
F6 C8 C9 118.6(2) . . ?
C9 C8 C7 121.4(2) . . ?
F7 C9 C8 118.6(2) . . ?
F7 C9 C10 120.2(2) . . ?
C10 C9 C8 121.2(3) . . ?
F4 C4 C5 120.4(2) . . ?
F4 C4 C3 120.2(2) . . ?
C3 C4 C5 119.4(3) . . ?
F2 C2 C1 120.0(3) . . ?
F2 C2 C3 120.7(2) . . ?
C3 C2 C1 119.4(2) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
F3 C3 C4 120.0(3) . . ?
F3 C3 C2 119.7(3) . . ?
C2 C3 C4 120.3(2) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?

_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.737
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-pentane'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2131401'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2022-02-05 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_7                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         18 Note
RESPONSE: This refers to the number of reflections placed under the shadow of the detector and are neglected by the program. Adding these reflections means to introduce in the mathematical processing reflections with intensities altered, so it is better to accept the processing made by the program. No action is required.
;
# Added during the CSD deposition process: Saturday 05 February 2022 06:59 PM
# end Validation Reply Form

_audit_creation_date             2021-10-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C45 H49 F10 P Pd'
_chemical_formula_sum            'C45 H48.96 F10 P Pd'
_chemical_formula_weight         917.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C45 H49 F10 P Pd'
_chemical_oxdiff_usercomment     colorless
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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                   20.2800(5)
_cell_length_b                   11.8689(3)
_cell_length_c                   17.7116(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.392(2)
_cell_angle_gamma                90
_cell_volume                     4129.42(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5534
_cell_measurement_temperature    294
_cell_measurement_theta_max      28.4460
_cell_measurement_theta_min      3.8340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -1 2 0.1245
5 1 -2 0.1515
-1 0 5 0.0600
1 0 -5 0.0850
2 -5 0 0.0821
-2 5 0 0.0951
-5 -1 0 0.1191
5 1 0 0.1491
-1 0 -1 0.1134
5 -1 -3 0.1328
5 4 -4 0.1178
-5 -3 -3 0.1166

_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.145
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
-5.0000 -1.0000 2.0000 -0.0383 -0.0386 -0.1807
5.0000 1.0000 -2.0000 0.0383 0.0386 0.1807
-1.0000 -0.0000 5.0000 0.1045 0.1196 -0.1230
1.0000 0.0000 -5.0000 -0.1045 -0.1196 0.1230
2.0000 -5.0000 -0.0000 -0.2386 0.1919 -0.0252
-2.0000 5.0000 0.0000 0.2386 -0.1919 0.0252
-5.0000 -1.0000 -0.0000 -0.0827 -0.0964 -0.1416
5.0000 1.0000 0.0000 0.0827 0.0964 0.1416
-1.0000 0.0000 -1.0000 -0.0287 -0.0539 -0.0057
5.0000 -1.0000 -3.0000 -0.0846 0.0664 0.1699
5.0000 4.0000 -4.0000 0.1448 -0.1045 0.2652
-5.0000 -3.0000 -3.0000 -0.2499 -0.1263 -0.1132

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17887
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.630
_diffrn_reflns_theta_min         3.413
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  17.00   1.00   17.54    --  -10.48 -77.00-120.00   99
  2  ω     35.00 100.00   1.00   17.54    --   12.36-178.00 120.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064676000
_diffrn_orient_matrix_UB_12      0.0503142000
_diffrn_orient_matrix_UB_13      0.0221956000
_diffrn_orient_matrix_UB_21      0.0249587000
_diffrn_orient_matrix_UB_22      -0.0283987000
_diffrn_orient_matrix_UB_23      0.0289157000
_diffrn_orient_matrix_UB_31      0.0252828000
_diffrn_orient_matrix_UB_32      0.0151490000
_diffrn_orient_matrix_UB_33      -0.0195481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6266
_reflns_number_total             9636
_reflns_odcompleteness_completeness 99.05
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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         0.438
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         9636
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+1.8411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0987
_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. Others
 1*[Sof(C44)+Sof(H44A)+Sof(H44B)+Sof(H44C)+Sof(C46)+Sof(H46A)+Sof(H46B)+
 Sof(H46C)]=1 with esd of 1
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=1-FVAR(1)
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
 Sof(H43A)=Sof(C45A)=Sof(H45D)=Sof(H45E)=Sof(H45F)=1-FVAR(2)
 Sof(H43)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C19(H19), C13(H13), C40(H40), C37(H37), C43(H43), C43(H43A)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C18(H18A,H18B), C24(H24A,H24B), C14(H14A,H14B), C16(H16A,
 H16B), C23(H23A,H23B), C22(H22A,H22B), C17(H17A,H17B), C21(H21A,H21B),
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C33(H33), C35(H35), C28(H28), C29(H29)
3.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C45A(H45D,H45E,H45F),
 C46(H46A,H46B,H46C)
;
_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
Pd1 Pd 0.73517(2) 0.49373(2) 0.31721(2) 0.03290(8) Uani 1 1 d . . . . .
P1 P 0.84118(3) 0.48407(6) 0.28899(4) 0.03066(17) Uani 1 1 d . . . . .
F6 F 0.77665(10) 0.70213(17) 0.43256(12) 0.0628(6) Uani 1 1 d . . . . .
F10 F 0.78515(11) 0.30488(17) 0.44831(12) 0.0643(6) Uani 1 1 d . . . . .
F1 F 0.64520(11) 0.29113(18) 0.35695(14) 0.0742(7) Uani 1 1 d . . . . .
F5 F 0.63816(11) 0.68744(18) 0.36434(15) 0.0804(7) Uani 1 1 d . . . . .
F9 F 0.83965(12) 0.3198(2) 0.60086(13) 0.0895(8) Uani 1 1 d . . . . .
F7 F 0.83148(12) 0.7150(2) 0.58456(14) 0.0916(8) Uani 1 1 d . . . . .
F2 F 0.52873(12) 0.2830(2) 0.40077(16) 0.0983(9) Uani 1 1 d . . . . .
F3 F 0.46465(10) 0.4748(2) 0.42433(15) 0.0996(9) Uani 1 1 d . . . . .
C19 C 0.90459(14) 0.5971(2) 0.32046(17) 0.0364(7) Uani 1 1 d . . . . .
H19 H 0.937709 0.589731 0.288797 0.044 Uiso 1 1 calc R U . . .
C13 C 0.88836(14) 0.3538(2) 0.32609(17) 0.0345(7) Uani 1 1 d . . . . .
H13 H 0.899344 0.359207 0.383072 0.041 Uiso 1 1 calc R U . . .
F4 F 0.52328(12) 0.6770(2) 0.41043(17) 0.1032(9) Uani 1 1 d . . . . .
F8 F 0.86339(14) 0.5252(3) 0.67101(13) 0.1119(10) Uani 1 1 d . . . . .
C7 C 0.77814(14) 0.5025(3) 0.43245(16) 0.0368(7) Uani 1 1 d . . . . .
C20 C 0.94474(15) 0.5881(3) 0.40597(18) 0.0453(8) Uani 1 1 d . . . . .
H20A H 0.913310 0.587694 0.439267 0.054 Uiso 1 1 calc R U . . .
H20B H 0.969861 0.517729 0.413842 0.054 Uiso 1 1 calc R U . . .
C25 C 0.82592(14) 0.4827(2) 0.18360(16) 0.0323(6) Uani 1 1 d . . . . .
C30 C 0.75821(14) 0.4804(3) 0.14009(17) 0.0377(7) Uani 1 1 d . . . . .
C31 C 0.69596(14) 0.4804(3) 0.17335(17) 0.0407(8) Uani 1 1 d . . . . .
C26 C 0.87799(15) 0.4873(3) 0.14473(18) 0.0402(7) Uani 1 1 d . . . . .
H26 H 0.923053 0.489339 0.173586 0.048 Uiso 1 1 calc R U . . .
C18 C 0.95620(14) 0.3351(3) 0.30469(19) 0.0442(8) Uani 1 1 d . . . . .
H18A H 0.947929 0.323534 0.248902 0.053 Uiso 1 1 calc R U . . .
H18B H 0.984568 0.401464 0.318343 0.053 Uiso 1 1 calc R U . . .
C12 C 0.79553(16) 0.4086(3) 0.4790(2) 0.0453(8) Uani 1 1 d . . . . .
C24 C 0.87107(16) 0.7120(3) 0.30174(19) 0.0450(8) Uani 1 1 d . . . . .
H24A H 0.852837 0.718024 0.245811 0.054 Uiso 1 1 calc R U . . .
H24B H 0.833257 0.717635 0.325996 0.054 Uiso 1 1 calc R U . . .
C8 C 0.79072(16) 0.6044(3) 0.4712(2) 0.0455(8) Uani 1 1 d . . . . .
C27 C 0.86390(16) 0.4888(3) 0.06458(18) 0.0487(8) Uani 1 1 d . . . . .
H27 H 0.899050 0.492345 0.039492 0.058 Uiso 1 1 calc R U . . .
C36 C 0.66283(15) 0.5860(3) 0.17641(18) 0.0464(8) Uani 1 1 d . . . . .
C1 C 0.64596(14) 0.4897(3) 0.35506(17) 0.0388(7) Uani 1 1 d . . . . .
C32 C 0.65872(15) 0.3786(3) 0.17064(19) 0.0478(8) Uani 1 1 d . . . . .
C6 C 0.61342(17) 0.5834(3) 0.3724(2) 0.0522(9) Uani 1 1 d . . . . .
C2 C 0.61630(16) 0.3897(3) 0.3685(2) 0.0488(9) Uani 1 1 d . . . . .
C14 C 0.84486(16) 0.2488(3) 0.3050(2) 0.0466(8) Uani 1 1 d . . . . .
H14A H 0.835821 0.235652 0.249330 0.056 Uiso 1 1 calc R U . . .
H14B H 0.801591 0.260033 0.318000 0.056 Uiso 1 1 calc R U . . .
C34 C 0.55714(15) 0.4879(4) 0.17316(19) 0.0577(11) Uani 1 1 d . . . . .
C40 C 0.69529(17) 0.6968(3) 0.1644(2) 0.0543(9) Uani 1 1 d . . . . .
H40 H 0.743631 0.682289 0.168578 0.065 Uiso 1 1 calc R U . . .
C5 C 0.55379(18) 0.5802(4) 0.3970(2) 0.0636(11) Uani 1 1 d . . . . .
C9 C 0.81946(18) 0.6127(4) 0.5507(2) 0.0611(11) Uani 1 1 d . . . . .
C16 C 0.94983(18) 0.1281(3) 0.3319(2) 0.0646(11) Uani 1 1 d . . . . .
H16A H 0.973148 0.067038 0.364152 0.078 Uiso 1 1 calc R U . . .
H16B H 0.943579 0.106331 0.277787 0.078 Uiso 1 1 calc R U . . .
C23 C 0.91960(19) 0.8100(3) 0.3294(2) 0.0592(10) Uani 1 1 d . . . . .
H23A H 0.952304 0.813806 0.297730 0.071 Uiso 1 1 calc R U . . .
H23B H 0.894020 0.879911 0.322426 0.071 Uiso 1 1 calc R U . . .
C22 C 0.9573(2) 0.7978(3) 0.4143(2) 0.0663(11) Uani 1 1 d . . . . .
H22A H 0.989833 0.858732 0.428829 0.080 Uiso 1 1 calc R U . . .
H22B H 0.925174 0.802856 0.446665 0.080 Uiso 1 1 calc R U . . .
C17 C 0.99319(16) 0.2327(3) 0.3477(2) 0.0523(9) Uani 1 1 d . . . . .
H17A H 1.034864 0.220165 0.331395 0.063 Uiso 1 1 calc R U . . .
H17B H 1.005430 0.247699 0.403265 0.063 Uiso 1 1 calc R U . . .
C33 C 0.59018(16) 0.3864(4) 0.17169(19) 0.0563(10) Uani 1 1 d . . . . .
H33 H 0.565651 0.320161 0.171394 0.068 Uiso 1 1 calc R U . . .
C11 C 0.82432(18) 0.4153(4) 0.5587(2) 0.0615(11) Uani 1 1 d . . . . .
C3 C 0.55683(18) 0.3829(4) 0.3920(2) 0.0612(10) Uani 1 1 d . . . . .
C35 C 0.59421(16) 0.5849(4) 0.1776(2) 0.0577(10) Uani 1 1 d . . . . .
H35 H 0.572828 0.653218 0.181571 0.069 Uiso 1 1 calc R U . . .
C21 C 0.99416(17) 0.6863(3) 0.4285(2) 0.0572(10) Uani 1 1 d . . . . .
H21A H 1.017664 0.680106 0.483217 0.069 Uiso 1 1 calc R U . . .
H21B H 1.027937 0.682896 0.398271 0.069 Uiso 1 1 calc R U . . .
C15 C 0.88049(18) 0.1462(3) 0.3486(2) 0.0624(10) Uani 1 1 d . . . . .
H15A H 0.886188 0.156773 0.404176 0.075 Uiso 1 1 calc R U . . .
H15B H 0.852491 0.079895 0.332903 0.075 Uiso 1 1 calc R U . . .
C4 C 0.52500(17) 0.4791(4) 0.4051(2) 0.0643(11) Uani 1 1 d . . . . .
C28 C 0.79732(18) 0.4850(3) 0.0221(2) 0.0605(10) Uani 1 1 d . . . . .
H28 H 0.787306 0.485194 -0.032033 0.073 Uiso 1 1 calc R U . . .
C37 C 0.68727(18) 0.2661(3) 0.1541(2) 0.0577(10) Uani 1 1 d . . . . .
H37 H 0.736534 0.274960 0.161708 0.069 Uiso 1 1 calc R U . . .
C29 C 0.74571(16) 0.4811(3) 0.05910(19) 0.0582(10) Uani 1 1 d . . . . .
H29 H 0.700944 0.478766 0.029340 0.070 Uiso 1 1 calc R U . . .
C10 C 0.8356(2) 0.5178(4) 0.5940(2) 0.0696(12) Uani 1 1 d . . . . .
C42 C 0.6639(2) 0.7415(4) 0.0814(2) 0.0775(13) Uani 1 1 d . . . . .
H42A H 0.671881 0.688211 0.043860 0.116 Uiso 1 1 calc R U . . .
H42B H 0.684506 0.812255 0.074445 0.116 Uiso 1 1 calc R U . . .
H42C H 0.615783 0.751681 0.074309 0.116 Uiso 1 1 calc R U . . .
C41 C 0.6911(2) 0.7872(3) 0.2247(2) 0.0747(12) Uani 1 1 d . . . . .
H41A H 0.644243 0.806186 0.220281 0.112 Uiso 1 1 calc R U . . .
H41B H 0.715350 0.853144 0.215524 0.112 Uiso 1 1 calc R U . . .
H41C H 0.710950 0.758932 0.276115 0.112 Uiso 1 1 calc R U . . .
C38 C 0.6755(2) 0.1718(3) 0.2082(3) 0.0785(13) Uani 1 1 d . . . . .
H38A H 0.692486 0.194840 0.261492 0.118 Uiso 1 1 calc R U . . .
H38B H 0.699045 0.105078 0.198836 0.118 Uiso 1 1 calc R U . . .
H38C H 0.627679 0.156284 0.198322 0.118 Uiso 1 1 calc R U . . .
C39 C 0.6573(2) 0.2302(4) 0.0691(2) 0.0825(13) Uani 1 1 d . . . . .
H39A H 0.608620 0.226433 0.058968 0.124 Uiso 1 1 calc R U . . .
H39B H 0.674865 0.157489 0.060451 0.124 Uiso 1 1 calc R U . . .
H39C H 0.669780 0.284236 0.034747 0.124 Uiso 1 1 calc R U . . .
C43 C 0.48048(17) 0.4928(6) 0.1638(2) 0.0955(18) Uani 1 1 d . . . . .
H43 H 0.466181 0.570357 0.170126 0.115 Uiso 0.588(9) 1 calc R U P A 1
H43A H 0.468454 0.414260 0.171135 0.115 Uiso 0.412(9) 1 calc R U P A 2
C44 C 0.4455(12) 0.448(4) 0.0783(15) 0.081(7) Uani 0.38(4) 1 d . . P A 1
H44A H 0.464482 0.376174 0.070441 0.122 Uiso 0.38(4) 1 calc R U P A 1
H44B H 0.453547 0.500707 0.040442 0.122 Uiso 0.38(4) 1 calc R U P A 1
H44C H 0.397365 0.440261 0.072526 0.122 Uiso 0.38(4) 1 calc R U P A 1
C45 C 0.4501(3) 0.4212(8) 0.2035(4) 0.075(3) Uani 0.588(9) 1 d . . P A 1
H45A H 0.401878 0.434614 0.189805 0.113 Uiso 0.588(9) 1 calc R U P A 1
H45B H 0.467778 0.433021 0.258472 0.113 Uiso 0.588(9) 1 calc R U P A 1
H45C H 0.458886 0.345079 0.190642 0.113 Uiso 0.588(9) 1 calc R U P A 1
C45A C 0.4505(5) 0.5467(13) 0.2067(6) 0.083(5) Uani 0.412(9) 1 d . . P A 2
H45D H 0.479006 0.549991 0.258757 0.125 Uiso 0.412(9) 1 calc R U P A 2
H45E H 0.408563 0.509448 0.207210 0.125 Uiso 0.412(9) 1 calc R U P A 2
H45F H 0.440947 0.621766 0.186777 0.125 Uiso 0.412(9) 1 calc R U P A 2
C46 C 0.4446(6) 0.516(3) 0.0772(8) 0.082(6) Uani 0.62(4) 1 d . . P A 2
H46A H 0.468342 0.575113 0.057646 0.123 Uiso 0.62(4) 1 calc R U P A 2
H46B H 0.398479 0.539039 0.073064 0.123 Uiso 0.62(4) 1 calc R U P A 2
H46C H 0.444949 0.448965 0.047117 0.123 Uiso 0.62(4) 1 calc R U 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
Pd1 P1 2.3278(7) . ?
Pd1 C7 2.013(3) . ?
Pd1 C31 2.478(3) . ?
Pd1 C1 2.080(3) . ?
P1 C19 1.846(3) . ?
P1 C13 1.851(3) . ?
P1 C25 1.815(3) . ?
F6 C8 1.341(4) . ?
F10 C12 1.341(4) . ?
F1 C2 1.347(4) . ?
F5 C6 1.354(4) . ?
F9 C11 1.350(4) . ?
F7 C9 1.349(4) . ?
F2 C3 1.341(4) . ?
F3 C4 1.351(4) . ?
C19 H19 0.9800 . ?
C19 C20 1.535(4) . ?
C19 C24 1.523(4) . ?
C13 H13 0.9800 . ?
C13 C18 1.531(4) . ?
C13 C14 1.519(4) . ?
F4 C5 1.354(4) . ?
F8 C10 1.342(4) . ?
C7 C12 1.380(4) . ?
C7 C8 1.382(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.524(4) . ?
C25 C30 1.398(4) . ?
C25 C26 1.398(4) . ?
C30 C31 1.520(4) . ?
C30 C29 1.393(4) . ?
C31 C36 1.430(4) . ?
C31 C32 1.419(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.528(4) . ?
C12 C11 1.389(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C23 1.523(4) . ?
C8 C9 1.387(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.373(4) . ?
C36 C40 1.509(5) . ?
C36 C35 1.397(4) . ?
C1 C6 1.366(4) . ?
C1 C2 1.377(4) . ?
C32 C33 1.398(4) . ?
C32 C37 1.513(5) . ?
C6 C5 1.384(4) . ?
C2 C3 1.372(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(4) . ?
C34 C33 1.382(5) . ?
C34 C35 1.367(5) . ?
C34 C43 1.523(4) . ?
C40 H40 0.9800 . ?
C40 C42 1.544(5) . ?
C40 C41 1.531(5) . ?
C5 C4 1.357(5) . ?
C9 C10 1.357(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.507(5) . ?
C16 C15 1.523(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.516(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.510(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C33 H33 0.9300 . ?
C11 C10 1.361(6) . ?
C3 C4 1.360(5) . ?
C35 H35 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C28 H28 0.9300 . ?
C28 C29 1.366(4) . ?
C37 H37 0.9800 . ?
C37 C38 1.530(5) . ?
C37 C39 1.538(5) . ?
C29 H29 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C43 H43 0.9800 . ?
C43 H43A 0.9800 . ?
C43 C44 1.60(2) . ?
C43 C45 1.346(8) . ?
C43 C45A 1.259(10) . ?
C43 C46 1.552(13) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C45A H45D 0.9600 . ?
C45A H45E 0.9600 . ?
C45A H45F 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Pd1 C31 81.58(7) . . ?
C7 Pd1 P1 91.73(8) . . ?
C7 Pd1 C31 173.29(10) . . ?
C7 Pd1 C1 82.33(11) . . ?
C1 Pd1 P1 172.57(8) . . ?
C1 Pd1 C31 104.32(10) . . ?
C19 P1 Pd1 120.71(10) . . ?
C19 P1 C13 103.89(13) . . ?
C13 P1 Pd1 112.86(9) . . ?
C25 P1 Pd1 106.91(9) . . ?
C25 P1 C19 104.18(13) . . ?
C25 P1 C13 107.38(13) . . ?
P1 C19 H19 106.7 . . ?
C20 C19 P1 114.0(2) . . ?
C20 C19 H19 106.7 . . ?
C24 C19 P1 110.2(2) . . ?
C24 C19 H19 106.7 . . ?
C24 C19 C20 112.1(3) . . ?
P1 C13 H13 106.0 . . ?
C18 C13 P1 116.8(2) . . ?
C18 C13 H13 106.0 . . ?
C14 C13 P1 112.4(2) . . ?
C14 C13 H13 106.0 . . ?
C14 C13 C18 108.8(2) . . ?
C12 C7 Pd1 123.1(2) . . ?
C12 C7 C8 115.0(3) . . ?
C8 C7 Pd1 121.9(2) . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C19 111.0(3) . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C30 C25 P1 117.4(2) . . ?
C26 C25 P1 123.4(2) . . ?
C26 C25 C30 119.2(3) . . ?
C25 C30 C31 125.7(3) . . ?
C29 C30 C25 118.0(3) . . ?
C29 C30 C31 116.3(3) . . ?
C30 C31 Pd1 108.26(18) . . ?
C36 C31 Pd1 86.48(19) . . ?
C36 C31 C30 117.3(3) . . ?
C32 C31 Pd1 97.0(2) . . ?
C32 C31 C30 118.2(3) . . ?
C32 C31 C36 119.8(3) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.3 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C17 C18 C13 110.6(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
F10 C12 C7 120.5(3) . . ?
F10 C12 C11 116.7(3) . . ?
C7 C12 C11 122.8(4) . . ?
C19 C24 H24A 108.9 . . ?
C19 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C23 C24 C19 113.3(3) . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
F6 C8 C7 120.9(3) . . ?
F6 C8 C9 116.0(3) . . ?
C7 C8 C9 123.0(4) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 C26 119.2(3) . . ?
C28 C27 H27 120.4 . . ?
C31 C36 C40 122.2(3) . . ?
C35 C36 C31 118.2(3) . . ?
C35 C36 C40 118.7(3) . . ?
C6 C1 Pd1 124.1(2) . . ?
C6 C1 C2 114.0(3) . . ?
C2 C1 Pd1 121.9(2) . . ?
C31 C32 C37 122.1(3) . . ?
C33 C32 C31 117.7(3) . . ?
C33 C32 C37 119.4(3) . . ?
F5 C6 C1 120.4(3) . . ?
F5 C6 C5 115.7(3) . . ?
C1 C6 C5 123.9(3) . . ?
F1 C2 C1 119.8(3) . . ?
F1 C2 C3 116.3(3) . . ?
C3 C2 C1 123.9(3) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 C15 111.0(3) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C33 C34 C43 121.2(4) . . ?
C35 C34 C33 118.2(3) . . ?
C35 C34 C43 120.4(4) . . ?
C36 C40 H40 107.4 . . ?
C36 C40 C42 110.0(3) . . ?
C36 C40 C41 114.3(3) . . ?
C42 C40 H40 107.4 . . ?
C41 C40 H40 107.4 . . ?
C41 C40 C42 110.0(3) . . ?
F4 C5 C6 120.4(4) . . ?
F4 C5 C4 120.3(3) . . ?
C4 C5 C6 119.3(4) . . ?
F7 C9 C8 120.0(4) . . ?
F7 C9 C10 120.3(4) . . ?
C10 C9 C8 119.8(4) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C17 C16 C15 111.8(3) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C22 C23 C24 111.8(3) . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C21 C22 C23 110.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 C18 111.8(3) . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C32 C33 H33 118.4 . . ?
C34 C33 C32 123.2(3) . . ?
C34 C33 H33 118.4 . . ?
F9 C11 C12 119.6(4) . . ?
F9 C11 C10 120.5(4) . . ?
C10 C11 C12 119.9(4) . . ?
F2 C3 C2 121.2(4) . . ?
F2 C3 C4 119.3(3) . . ?
C4 C3 C2 119.5(4) . . ?
C36 C35 H35 118.6 . . ?
C34 C35 C36 122.8(4) . . ?
C34 C35 H35 118.6 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 C20 111.1(3) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 C14 111.0(3) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
F3 C4 C5 120.1(4) . . ?
F3 C4 C3 120.6(4) . . ?
C5 C4 C3 119.3(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.3(3) . . ?
C29 C28 H28 119.8 . . ?
C32 C37 H37 107.8 . . ?
C32 C37 C38 113.5(3) . . ?
C32 C37 C39 110.9(3) . . ?
C38 C37 H37 107.8 . . ?
C38 C37 C39 109.0(3) . . ?
C39 C37 H37 107.8 . . ?
C30 C29 H29 119.0 . . ?
C28 C29 C30 121.9(3) . . ?
C28 C29 H29 119.0 . . ?
F8 C10 C9 120.1(4) . . ?
F8 C10 C11 120.3(4) . . ?
C9 C10 C11 119.5(3) . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C34 C43 H43 110.3 . . ?
C34 C43 H43A 103.3 . . ?
C34 C43 C44 106.9(9) . . ?
C34 C43 C46 109.2(6) . . ?
C44 C43 H43 110.3 . . ?
C45 C43 C34 120.5(5) . . ?
C45 C43 H43 110.3 . . ?
C45 C43 C44 97.6(18) . . ?
C45A C43 C34 126.0(6) . . ?
C45A C43 H43A 103.3 . . ?
C45A C43 C46 109.1(12) . . ?
C46 C43 H43A 103.3 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C45A H45D 109.5 . . ?
C43 C45A H45E 109.5 . . ?
C43 C45A H45F 109.5 . . ?
H45D C45A H45E 109.5 . . ?
H45D C45A H45F 109.5 . . ?
H45E C45A H45F 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 P1 C19 C20 80.9(2) . . . . ?
Pd1 P1 C19 C24 -46.1(2) . . . . ?
Pd1 P1 C13 C18 175.17(19) . . . . ?
Pd1 P1 C13 C14 48.4(2) . . . . ?
Pd1 P1 C25 C30 -3.8(3) . . . . ?
Pd1 P1 C25 C26 174.2(2) . . . . ?
Pd1 C7 C12 F10 1.1(4) . . . . ?
Pd1 C7 C12 C11 -179.1(2) . . . . ?
Pd1 C7 C8 F6 -2.2(4) . . . . ?
Pd1 C7 C8 C9 179.1(2) . . . . ?
Pd1 C31 C36 C40 95.5(3) . . . . ?
Pd1 C31 C36 C35 -95.2(3) . . . . ?
Pd1 C31 C32 C33 89.4(3) . . . . ?
Pd1 C31 C32 C37 -100.3(3) . . . . ?
Pd1 C1 C6 F5 0.9(5) . . . . ?
Pd1 C1 C6 C5 179.5(3) . . . . ?
Pd1 C1 C2 F1 -0.1(4) . . . . ?
Pd1 C1 C2 C3 -178.6(3) . . . . ?
P1 C19 C20 C21 -177.9(2) . . . . ?
P1 C19 C24 C23 177.4(2) . . . . ?
P1 C13 C18 C17 172.8(2) . . . . ?
P1 C13 C14 C15 -169.5(2) . . . . ?
P1 C25 C30 C31 0.8(4) . . . . ?
P1 C25 C30 C29 179.0(2) . . . . ?
P1 C25 C26 C27 -178.4(2) . . . . ?
F6 C8 C9 F7 0.1(5) . . . . ?
F6 C8 C9 C10 -179.6(3) . . . . ?
F10 C12 C11 F9 -0.6(5) . . . . ?
F10 C12 C11 C10 -179.3(3) . . . . ?
F1 C2 C3 F2 -1.6(5) . . . . ?
F1 C2 C3 C4 179.7(3) . . . . ?
F5 C6 C5 F4 0.9(5) . . . . ?
F5 C6 C5 C4 178.8(3) . . . . ?
F9 C11 C10 F8 1.2(6) . . . . ?
F9 C11 C10 C9 -179.6(3) . . . . ?
F7 C9 C10 F8 0.4(6) . . . . ?
F7 C9 C10 C11 -178.8(3) . . . . ?
F2 C3 C4 F3 -2.1(6) . . . . ?
F2 C3 C4 C5 179.3(3) . . . . ?
C19 P1 C13 C18 -52.4(3) . . . . ?
C19 P1 C13 C14 -179.1(2) . . . . ?
C19 P1 C25 C30 -132.7(2) . . . . ?
C19 P1 C25 C26 45.3(3) . . . . ?
C19 C20 C21 C22 57.0(4) . . . . ?
C19 C24 C23 C22 -51.0(4) . . . . ?
C13 P1 C19 C20 -46.8(2) . . . . ?
C13 P1 C19 C24 -173.8(2) . . . . ?
C13 P1 C25 C30 117.6(2) . . . . ?
C13 P1 C25 C26 -64.4(3) . . . . ?
C13 C18 C17 C16 56.2(4) . . . . ?
C13 C14 C15 C16 -57.2(4) . . . . ?
F4 C5 C4 F3 2.0(6) . . . . ?
F4 C5 C4 C3 -179.4(4) . . . . ?
C7 C12 C11 F9 179.6(3) . . . . ?
C7 C12 C11 C10 0.8(5) . . . . ?
C7 C8 C9 F7 178.8(3) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C20 C19 C24 C23 49.3(4) . . . . ?
C25 P1 C19 C20 -159.2(2) . . . . ?
C25 P1 C19 C24 73.8(2) . . . . ?
C25 P1 C13 C18 57.6(2) . . . . ?
C25 P1 C13 C14 -69.2(2) . . . . ?
C25 C30 C31 Pd1 2.5(4) . . . . ?
C25 C30 C31 C36 98.0(4) . . . . ?
C25 C30 C31 C32 -106.3(4) . . . . ?
C25 C30 C29 C28 -0.6(5) . . . . ?
C25 C26 C27 C28 -0.4(5) . . . . ?
C30 C25 C26 C27 -0.4(4) . . . . ?
C30 C31 C36 C40 -13.2(4) . . . . ?
C30 C31 C36 C35 156.0(3) . . . . ?
C30 C31 C32 C33 -155.5(3) . . . . ?
C30 C31 C32 C37 14.8(5) . . . . ?
C31 C30 C29 C28 177.7(3) . . . . ?
C31 C36 C40 C42 102.3(4) . . . . ?
C31 C36 C40 C41 -133.4(3) . . . . ?
C31 C36 C35 C34 -2.4(5) . . . . ?
C31 C32 C33 C34 1.8(5) . . . . ?
C31 C32 C37 C38 135.5(3) . . . . ?
C31 C32 C37 C39 -101.4(4) . . . . ?
C26 C25 C30 C31 -177.3(3) . . . . ?
C26 C25 C30 C29 0.9(4) . . . . ?
C26 C27 C28 C29 0.7(6) . . . . ?
C18 C13 C14 C15 59.6(3) . . . . ?
C12 C7 C8 F6 179.5(3) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
C12 C11 C10 F8 179.9(3) . . . . ?
C12 C11 C10 C9 -0.9(6) . . . . ?
C24 C19 C20 C21 -51.9(3) . . . . ?
C24 C23 C22 C21 55.3(4) . . . . ?
C8 C7 C12 F10 179.4(3) . . . . ?
C8 C7 C12 C11 -0.8(4) . . . . ?
C8 C9 C10 F8 -179.9(3) . . . . ?
C8 C9 C10 C11 0.9(6) . . . . ?
C27 C28 C29 C30 -0.2(6) . . . . ?
C36 C31 C32 C33 -0.5(5) . . . . ?
C36 C31 C32 C37 169.8(3) . . . . ?
C1 C6 C5 F4 -177.7(3) . . . . ?
C1 C6 C5 C4 0.2(6) . . . . ?
C1 C2 C3 F2 177.0(3) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C32 C31 C36 C40 -168.4(3) . . . . ?
C32 C31 C36 C35 0.8(5) . . . . ?
C6 C1 C2 F1 -177.2(3) . . . . ?
C6 C1 C2 C3 4.3(5) . . . . ?
C6 C5 C4 F3 -175.9(3) . . . . ?
C6 C5 C4 C3 2.7(6) . . . . ?
C2 C1 C6 F5 177.9(3) . . . . ?
C2 C1 C6 C5 -3.5(5) . . . . ?
C2 C3 C4 F3 176.6(3) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C14 C13 C18 C17 -58.7(3) . . . . ?
C40 C36 C35 C34 167.2(3) . . . . ?
C23 C22 C21 C20 -58.8(4) . . . . ?
C17 C16 C15 C14 53.4(4) . . . . ?
C33 C32 C37 C38 -54.4(4) . . . . ?
C33 C32 C37 C39 68.7(4) . . . . ?
C33 C34 C35 C36 3.6(5) . . . . ?
C33 C34 C43 C44 -64.2(19) . . . . ?
C33 C34 C43 C45 45.6(7) . . . . ?
C33 C34 C43 C45A 131.6(10) . . . . ?
C33 C34 C43 C46 -95.5(14) . . . . ?
C35 C36 C40 C42 -66.9(4) . . . . ?
C35 C36 C40 C41 57.4(4) . . . . ?
C35 C34 C33 C32 -3.3(5) . . . . ?
C35 C34 C43 C44 111.0(19) . . . . ?
C35 C34 C43 C45 -139.1(6) . . . . ?
C35 C34 C43 C45A -53.1(11) . . . . ?
C35 C34 C43 C46 79.8(14) . . . . ?
C15 C16 C17 C18 -53.2(4) . . . . ?
C37 C32 C33 C34 -168.8(3) . . . . ?
C29 C30 C31 Pd1 -175.7(2) . . . . ?
C29 C30 C31 C36 -80.2(4) . . . . ?
C29 C30 C31 C32 75.5(4) . . . . ?
C43 C34 C33 C32 172.1(3) . . . . ?
C43 C34 C35 C36 -171.8(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 1.069
_oxdiff_exptl_absorpt_empirical_full_min 0.927
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/n-hexane'
####################################################################### 
# 
# 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_3fn
_database_code_depnum_ccdc_archive 'CCDC 2131399'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 F6'
_chemical_formula_sum            'C12 H4 F6'
_chemical_formula_weight         262.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H4 F6'
_chemical_oxdiff_usercomment     'colorless '
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      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                   13.3244(14)
_cell_length_b                   5.9453(5)
_cell_length_c                   13.0908(15)
_cell_angle_alpha                90
_cell_angle_beta                 108.653(13)
_cell_angle_gamma                90
_cell_volume                     982.55(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1070
_cell_measurement_temperature    294
_cell_measurement_theta_max      27.2830
_cell_measurement_theta_min      4.6000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.772
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.2973
0 0 1 0.3473
0 -1 0 0.2827
0 1 0 0.1967
-1 0 0 0.1065
1 0 0 0.0825
-1 -5 3 0.3204

_exptl_crystal_size_max          0.744
_exptl_crystal_size_mid          0.479
_exptl_crystal_size_min          0.189
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
0.0000 -0.0000 -1.0000 0.0568 0.0063 0.0018
-0.0000 0.0000 1.0000 -0.0568 -0.0063 -0.0018
-0.0000 -1.0000 0.0000 0.0042 -0.0041 -0.1191
0.0000 1.0000 -0.0000 -0.0042 0.0041 0.1191
-1.0000 -0.0000 0.0000 0.0121 0.0548 -0.0015
1.0000 0.0000 -0.0000 -0.0121 -0.0548 0.0015
-1.0000 -5.0000 3.0000 -0.1377 0.0154 -0.6025

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4255
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.483
_diffrn_reflns_theta_min         3.788
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00   7.00   1.00    2.00    --  -10.48 -57.00 -30.00   85
  2  ω    -79.00   5.00   1.00    2.00    --  -10.48 -57.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0120708000
_diffrn_orient_matrix_UB_12      -0.0041595000
_diffrn_orient_matrix_UB_13      -0.0568395000
_diffrn_orient_matrix_UB_21      -0.0548384000
_diffrn_orient_matrix_UB_22      0.0041116000
_diffrn_orient_matrix_UB_23      -0.0062989000
_diffrn_orient_matrix_UB_31      0.0014633000
_diffrn_orient_matrix_UB_32      0.1191458000
_diffrn_orient_matrix_UB_33      -0.0017719000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1252
_reflns_number_total             2292
_reflns_odcompleteness_completeness 98.69
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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         0.355
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      0.963
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1862
_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:
 C8(H8), C12(H12), C9(H9), C11(H11)
;
_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
F5 F 0.69993(12) 0.3846(2) 0.63113(13) 0.0595(5) Uani 1 1 d . . . . .
F1 F 0.85401(12) 1.0713(2) 0.78320(13) 0.0611(5) Uani 1 1 d . . . . .
F4 F 0.82230(13) 0.3809(3) 0.50537(13) 0.0668(5) Uani 1 1 d . . . . .
F6 F 0.52349(13) 0.7397(3) 0.98374(15) 0.0729(5) Uani 1 1 d . . . . .
F3 F 0.95877(12) 0.7261(3) 0.51352(13) 0.0717(6) Uani 1 1 d . . . . .
F2 F 0.97497(13) 1.0655(3) 0.65577(14) 0.0715(5) Uani 1 1 d . . . . .
C7 C 0.70375(17) 0.7295(4) 0.78271(19) 0.0404(6) Uani 1 1 d . . . . .
C6 C 0.77167(17) 0.7285(3) 0.71199(19) 0.0392(6) Uani 1 1 d . . . . .
C5 C 0.76854(18) 0.5555(4) 0.6399(2) 0.0430(6) Uani 1 1 d . . . . .
C8 C 0.70720(19) 0.5521(4) 0.8524(2) 0.0456(6) Uani 1 1 d . . . . .
H8 H 0.7514 0.4303 0.8538 0.055 Uiso 1 1 calc R . . . .
C12 C 0.63683(19) 0.9097(4) 0.7811(2) 0.0477(6) Uani 1 1 d . . . . .
H12 H 0.6336 1.0297 0.7346 0.057 Uiso 1 1 calc R . . . .
C3 C 0.89959(19) 0.7244(4) 0.5784(2) 0.0485(6) Uani 1 1 d . . . . .
C1 C 0.84302(18) 0.8992(4) 0.7136(2) 0.0431(6) Uani 1 1 d . . . . .
C10 C 0.58165(19) 0.7356(4) 0.9156(2) 0.0482(6) Uani 1 1 d . . . . .
C4 C 0.83036(19) 0.5517(4) 0.5746(2) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.90619(19) 0.8980(4) 0.6492(2) 0.0473(6) Uani 1 1 d . . . . .
C9 C 0.64593(19) 0.5539(4) 0.9198(2) 0.0495(7) Uani 1 1 d . . . . .
H9 H 0.6483 0.4350 0.9667 0.059 Uiso 1 1 calc R . . . .
C11 C 0.57526(19) 0.9122(4) 0.8479(2) 0.0530(7) Uani 1 1 d . . . . .
H11 H 0.5302 1.0323 0.8467 0.064 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
F5 C5 1.347(3) . ?
F1 C1 1.346(3) . ?
F4 C4 1.343(3) . ?
F6 C10 1.356(3) . ?
F3 C3 1.331(3) . ?
F2 C2 1.338(3) . ?
C7 C6 1.487(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.390(3) . ?
C6 C5 1.388(3) . ?
C6 C1 1.386(3) . ?
C5 C4 1.363(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(3) . ?
C3 C4 1.370(3) . ?
C3 C2 1.372(4) . ?
C1 C2 1.368(3) . ?
C10 C9 1.369(3) . ?
C10 C11 1.359(4) . ?
C9 H9 0.9300 . ?
C11 H11 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
C8 C7 C6 120.55(19) . . ?
C8 C7 C12 118.8(2) . . ?
C12 C7 C6 120.6(2) . . ?
C5 C6 C7 122.31(19) . . ?
C1 C6 C7 122.6(2) . . ?
C1 C6 C5 115.1(2) . . ?
F5 C5 C6 119.3(2) . . ?
F5 C5 C4 117.6(2) . . ?
C4 C5 C6 123.1(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
F3 C3 C4 120.8(2) . . ?
F3 C3 C2 120.2(2) . . ?
C4 C3 C2 119.0(2) . . ?
F1 C1 C6 119.5(2) . . ?
F1 C1 C2 117.8(2) . . ?
C2 C1 C6 122.7(2) . . ?
F6 C10 C9 118.0(2) . . ?
F6 C10 C11 119.0(2) . . ?
C11 C10 C9 122.9(2) . . ?
F4 C4 C5 120.1(2) . . ?
F4 C4 C3 119.9(2) . . ?
C5 C4 C3 120.0(2) . . ?
F2 C2 C3 119.9(2) . . ?
F2 C2 C1 120.0(2) . . ?
C1 C2 C3 120.1(2) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 H9 121.0 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 H11 120.7 . . ?

_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 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.886
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-pentane'
####################################################################### 
# 
# 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_3gn
_database_code_depnum_ccdc_archive 'CCDC 2131400'
loop_
_audit_author_name
_audit_author_address
'Jaime Ponce de Leon'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_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         'C13 H4 F8'
_chemical_formula_sum            'C13 H4 F8'
_chemical_formula_weight         312.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H4 F8'
_chemical_oxdiff_usercomment     'colorless block'
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      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                   14.5626(17)
_cell_length_b                   5.8525(7)
_cell_length_c                   14.0383(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.599(10)
_cell_angle_gamma                90
_cell_volume                     1194.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    823
_cell_measurement_temperature    294
_cell_measurement_theta_max      23.0730
_cell_measurement_theta_min      4.0310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.736
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 5 0.1598
-1 0 0 0.0509
1 0 0 0.0509
1 -5 0 0.2781
-1 5 0 0.1351
-5 0 1 0.0443
2 0 -5 0.1378

_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.102
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
-1.0000 -0.0000 5.0000 -0.1924 0.1670 -0.0129
-1.0000 -0.0000 -0.0000 0.0270 0.0404 -0.0036
1.0000 0.0000 0.0000 -0.0270 -0.0404 0.0036
1.0000 -5.0000 -0.0000 -0.0319 -0.0946 -0.5996
-1.0000 5.0000 0.0000 0.0319 0.0946 0.5996
-5.0000 -0.0000 1.0000 0.0913 0.2274 -0.0201
2.0000 0.0000 -5.0000 0.1654 -0.2074 0.0166

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5001
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.700
_diffrn_reflns_theta_min         3.307
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  89.00   1.00    8.83    --   12.36  77.00-120.00   67
  2  ω    -16.00  83.00   1.00    8.83    --   12.36  77.00   0.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0270333000
_diffrn_orient_matrix_UB_12      0.0009781000
_diffrn_orient_matrix_UB_13      -0.0438869000
_diffrn_orient_matrix_UB_21      -0.0404111000
_diffrn_orient_matrix_UB_22      0.0108399000
_diffrn_orient_matrix_UB_23      0.0253116000
_diffrn_orient_matrix_UB_31      0.0036493000
_diffrn_orient_matrix_UB_32      0.1206597000
_diffrn_orient_matrix_UB_33      -0.0018510000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1184
_reflns_number_total             2778
_reflns_odcompleteness_completeness 98.70
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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         0.157
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.030
_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)+(0.0633P)²+0.1024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(C13)=Sof(F1A)=Sof(F2A)=Sof(F5A)=1-FVAR(1)
 Sof(F6)=Sof(F8)=Sof(C14)=Sof(F7)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C11(H11)
;
_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
F1 F 0.74361(12) 0.3771(3) 0.76831(11) 0.0799(6) Uani 1 1 d . . . . .
F5 F 0.87967(12) 1.0649(3) 0.66927(12) 0.0807(6) Uani 1 1 d . . . . .
F2 F 0.84540(13) 0.3990(3) 0.93358(12) 0.0894(7) Uani 1 1 d . . . . .
F3 F 0.96359(13) 0.7519(4) 0.96890(12) 0.0932(7) Uani 1 1 d . . . . .
F4 F 0.97990(13) 1.0835(4) 0.83526(13) 0.0935(7) Uani 1 1 d . . . . .
C6 C 0.80668(17) 0.7223(5) 0.71262(17) 0.0525(7) Uani 1 1 d . . . . .
C7 C 0.74914(19) 0.7119(5) 0.62118(18) 0.0551(7) Uani 1 1 d . . . . .
C5 C 0.86771(19) 0.8982(5) 0.73428(19) 0.0579(8) Uani 1 1 d . . . . .
C1 C 0.80191(19) 0.5541(5) 0.78240(19) 0.0581(8) Uani 1 1 d . . . . .
C4 C 0.9206(2) 0.9104(5) 0.8187(2) 0.0624(8) Uani 1 1 d . . . . .
C2 C 0.8536(2) 0.5641(5) 0.86781(19) 0.0620(8) Uani 1 1 d . . . . .
C3 C 0.9130(2) 0.7414(6) 0.88589(19) 0.0634(8) Uani 1 1 d . . . . .
C8 C 0.68834(19) 0.8869(6) 0.5961(2) 0.0644(8) Uani 1 1 d . . . . .
H8 H 0.685212 1.014494 0.635244 0.077 Uiso 1 1 calc R U . . .
C10 C 0.6365(2) 0.6838(6) 0.4550(2) 0.0650(8) Uani 1 1 d . . . . .
C9 C 0.6323(2) 0.8728(6) 0.5131(2) 0.0704(9) Uani 1 1 d . . . . .
H9 H 0.591689 0.990951 0.496526 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7535(2) 0.5252(6) 0.5606(2) 0.0684(9) Uani 1 1 d . . . . .
H12 H 0.795077 0.408190 0.575955 0.082 Uiso 1 1 calc R U . . .
C11 C 0.6974(2) 0.5103(6) 0.4780(2) 0.0710(9) Uani 1 1 d . . . . .
H11 H 0.700810 0.383846 0.438258 0.085 Uiso 1 1 calc R U . . .
F6 F 0.4858(6) 0.657(3) 0.3868(6) 0.121(5) Uani 0.64(2) 1 d . . P A 1
F8 F 0.5918(8) 0.494(3) 0.3101(8) 0.151(7) Uani 0.64(2) 1 d . . P A 1
C14 C 0.5753(8) 0.668(4) 0.3633(12) 0.076(5) Uani 0.64(2) 1 d . . P A 1
F7 F 0.5791(9) 0.849(3) 0.3115(9) 0.159(6) Uani 0.64(2) 1 d . . P A 1
C13 C 0.562(3) 0.653(9) 0.380(3) 0.118(16) Uani 0.36(2) 1 d . . P A 2
F1A F 0.5280(17) 0.450(4) 0.3729(13) 0.156(11) Uani 0.36(2) 1 d . . P A 2
F2A F 0.6052(9) 0.659(5) 0.2948(8) 0.124(7) Uani 0.36(2) 1 d . . P A 2
F5A F 0.510(2) 0.813(8) 0.3596(14) 0.212(17) Uani 0.36(2) 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
F1 C1 1.346(3) . ?
F5 C5 1.355(3) . ?
F2 C2 1.347(3) . ?
F3 C3 1.340(3) . ?
F4 C4 1.342(3) . ?
C6 C7 1.489(3) . ?
C6 C5 1.382(4) . ?
C6 C1 1.394(4) . ?
C7 C8 1.385(4) . ?
C7 C12 1.389(4) . ?
C5 C4 1.374(4) . ?
C1 C2 1.376(4) . ?
C4 C3 1.376(4) . ?
C2 C3 1.365(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(4) . ?
C10 C9 1.379(4) . ?
C10 C11 1.374(4) . ?
C10 C14 1.522(13) . ?
C10 C13 1.47(4) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.378(4) . ?
C11 H11 0.9300 . ?
F6 C14 1.365(18) . ?
F8 C14 1.30(2) . ?
C14 F7 1.29(2) . ?
C13 F1A 1.29(5) . ?
C13 F2A 1.38(4) . ?
C13 F5A 1.23(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 C7 122.6(2) . . ?
C5 C6 C1 115.6(2) . . ?
C1 C6 C7 121.8(2) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 C12 118.6(3) . . ?
C12 C7 C6 121.0(3) . . ?
F5 C5 C6 119.8(2) . . ?
F5 C5 C4 117.1(3) . . ?
C4 C5 C6 123.1(3) . . ?
F1 C1 C6 119.9(2) . . ?
F1 C1 C2 117.8(3) . . ?
C2 C1 C6 122.3(3) . . ?
F4 C4 C5 120.5(3) . . ?
F4 C4 C3 120.2(3) . . ?
C5 C4 C3 119.3(3) . . ?
F2 C2 C1 120.0(3) . . ?
F2 C2 C3 120.0(3) . . ?
C3 C2 C1 120.0(3) . . ?
F3 C3 C4 120.0(3) . . ?
F3 C3 C2 120.3(3) . . ?
C2 C3 C4 119.8(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C9 C10 C14 120.2(9) . . ?
C9 C10 C13 118(2) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 C14 119.4(9) . . ?
C11 C10 C13 121(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
F6 C14 C10 108.4(12) . . ?
F8 C14 C10 114.5(12) . . ?
F8 C14 F6 108.5(13) . . ?
F7 C14 C10 112.6(12) . . ?
F7 C14 F6 104.5(12) . . ?
F7 C14 F8 107.8(15) . . ?
F1A C13 C10 115(3) . . ?
F1A C13 F2A 99(3) . . ?
F2A C13 C10 105(3) . . ?
F5A C13 C10 119(4) . . ?
F5A C13 F1A 117(5) . . ?
F5A C13 F2A 95(3) . . ?

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
F1 C1 C2 F2 0.6(4) . . . . ?
F1 C1 C2 C3 -179.3(3) . . . . ?
F5 C5 C4 F4 1.1(4) . . . . ?
F5 C5 C4 C3 -178.0(3) . . . . ?
F2 C2 C3 F3 0.2(4) . . . . ?
F2 C2 C3 C4 -179.5(3) . . . . ?
F4 C4 C3 F3 1.4(4) . . . . ?
F4 C4 C3 C2 -178.9(3) . . . . ?
C6 C7 C8 C9 -177.4(2) . . . . ?
C6 C7 C12 C11 177.0(3) . . . . ?
C6 C5 C4 F4 178.9(3) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C6 C1 C2 F2 178.9(3) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C7 C6 C5 F5 -2.8(4) . . . . ?
C7 C6 C5 C4 179.4(3) . . . . ?
C7 C6 C1 F1 -0.5(4) . . . . ?
C7 C6 C1 C2 -178.8(3) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C7 C12 C11 C10 0.4(5) . . . . ?
C5 C6 C7 C8 -58.9(4) . . . . ?
C5 C6 C7 C12 122.7(3) . . . . ?
C5 C6 C1 F1 179.2(2) . . . . ?
C5 C6 C1 C2 0.9(4) . . . . ?
C5 C4 C3 F3 -179.5(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C1 C6 C7 C8 120.8(3) . . . . ?
C1 C6 C7 C12 -57.6(4) . . . . ?
C1 C6 C5 F5 177.5(2) . . . . ?
C1 C6 C5 C4 -0.3(4) . . . . ?
C1 C2 C3 F3 -179.9(2) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C8 C7 C12 C11 -1.4(4) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C9 C10 C14 F6 -65.3(17) . . . . ?
C9 C10 C14 F8 173.5(13) . . . . ?
C9 C10 C14 F7 49.8(17) . . . . ?
C9 C10 C13 F1A -134(3) . . . . ?
C9 C10 C13 F2A 118(3) . . . . ?
C9 C10 C13 F5A 14(6) . . . . ?
C12 C7 C8 C9 1.1(4) . . . . ?
C11 C10 C9 C8 -1.2(5) . . . . ?
C11 C10 C14 F6 116.3(13) . . . . ?
C11 C10 C14 F8 -5.0(19) . . . . ?
C11 C10 C14 F7 -128.6(14) . . . . ?
C11 C10 C13 F1A 34(5) . . . . ?
C11 C10 C13 F2A -74(4) . . . . ?
C11 C10 C13 F5A -178(4) . . . . ?
C14 C10 C9 C8 -179.6(8) . . . . ?
C14 C10 C11 C12 179.4(8) . . . . ?
C13 C10 C9 C8 167(2) . . . . ?
C13 C10 C11 C12 -167(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 1.778
_oxdiff_exptl_absorpt_empirical_full_min 0.737
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-pentane'
