# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_DFA_100K
_database_code_depnum_ccdc_archive 'CCDC 2293625'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details

loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2y (K.Radacki, 2005-22)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        decafluoroanthracene
_chemical_name_common            beta-decafluoroanthracene
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10'
_chemical_formula_sum            'C14 F10'
_chemical_formula_weight         358.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.8459(5)
_cell_length_b                   4.54869(9)
_cell_length_c                   11.3393(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.937(2)
_cell_angle_gamma                90
_cell_volume                     1093.61(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6027
_cell_measurement_theta_min      4.1600
_cell_measurement_theta_max      74.4020


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    2.282
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0238
-1 0 0 0.0269
-2 0 1 0.0620
1 0 -2 0.0899
0 -1 0 0.1275
0 1 0 0.1431
-1 2 2 0.1277
-1 -1 2 0.1322
-5 -2 -4 0.1231
-6 -3 0 0.1119
-5 3 3 0.1203
-5 2 5 0.1183

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     67.00  93.00   0.50    0.33    --   56.00  72.00 114.55   52
   2  ω     92.00 126.00   0.50    0.33    --   79.25  35.00  94.94   68
   3  ω     49.00 120.00   0.50    0.33    --   79.25  14.00 112.95  142
   4  ω     68.00 118.00   0.50    0.33    --   79.25  24.00-103.86  100
   5  ω     46.00  79.00   0.50    0.33    --   79.25   2.00-100.80   66
   6  ω     63.00  89.00   0.50    0.33    --   79.25  20.00-165.93   52
   7  ω     96.00 123.00   0.50    0.33    --   79.25  20.00-165.93   54
   8  ω     86.00 112.00   0.50    0.33    --   79.25  90.00-164.73   52
   9  ω     46.00  71.00   0.50    0.33    --   76.48-130.00-125.00   50
  10  ω     45.00  70.00   0.50    0.33    --   75.42-130.00-125.00   50
  11  ω     36.00  62.00   0.50    0.33    --   79.25-121.00 -37.25   52
  12  ω     78.00 106.00   0.50    0.33    --   79.25-121.00 -37.25   56
  13  ω     51.00  76.00   0.50    0.33    --   76.48-142.00  62.00   50
  14  ω     42.00  74.00   0.50    0.33    --   64.76-142.00  62.00   64
  15  ω     28.00  72.00   0.50    0.33    --   64.76 -95.00 -60.00   88
  16  ω     69.00  94.00   0.50    0.33    --   76.48 142.00 118.00   50
  17  ω    -65.00 -37.00   0.50    0.33    --  -77.75  62.00 -52.06   56
  18  ω    -98.00 -69.00   0.50    0.33    --  -75.51 130.00 -53.00   58
  19  ω    -92.00 -67.00   0.50    0.33    --  -74.18 130.00 -53.00   50
  20  ω    -91.00 -57.00   0.50    0.33    --  -77.75 122.00 -95.63   68
  21  ω   -104.00 -44.00   0.50    0.33    --  -77.75 120.00 -77.51  120
  22  ω   -102.00 -75.00   0.50    0.33    --  -77.75 116.00-161.01   54
  23  ω    -86.00 -60.00   0.50    0.33    --  -77.75 118.00  48.58   52
  24  ω   -104.00 -78.00   0.50    0.33    --  -77.75 123.00 134.96   52
  25  ω   -108.00 -74.00   0.50    0.33    --  -74.18 142.00 118.00   68
  26  ω    -91.00 -25.00   0.50    0.33    --  -64.72 142.00 118.00  132
  27  ω    -93.00 -68.00   0.50    0.33    --  -77.75 104.00 -13.88   50
  28  ω    -93.00 -38.00   0.50    0.33    --  -77.75 106.00 -40.17  110
  29  ω    -94.00 -68.00   0.50    0.33    --  -77.75 111.00-169.35   52
  30  ω    -71.00 -44.00   0.50    0.33    --  -77.75  87.00-138.10   54
  31  ω    -90.00 -65.00   0.50    0.33    --  -77.75 100.00-119.14   50
  32  ω    -77.00 -51.00   0.50    0.33    --  -77.75  86.00-108.91   52
  33  ω    -82.00 -45.00   0.50    0.33    --  -77.75 100.00  81.25   74
  34  ω    -76.00 -50.00   0.50    0.33    --  -77.75  88.00 146.06   52
  35  ω   -125.00 -88.00   0.50    0.33    --  -77.75 -36.00  -3.01   74
  36  ω   -114.00 -82.00   0.50    0.33    --  -72.00 -56.00  31.68   64
  37  ω   -114.00 -84.00   0.50    0.33    --  -77.75 -74.00  -9.94   60
  38  ω   -101.00 -73.00   0.50    0.33    --  -64.00 -67.00 -67.63   56
  39  ω    -83.00 -54.00   0.50    0.33    --  -44.00 -65.00-135.95   58
  40  ω   -124.00 -92.00   0.50    0.33    --  -77.75 -40.00-147.07   64
  41  ω   -119.00 -93.00   0.50    0.33    --  -77.75 -59.00-101.61   52
  42  ω   -124.00 -99.00   0.50    0.33    --  -77.75 -42.00  97.20   50
  43  ω   -104.00 -78.00   0.50    0.33    --  -68.00 -54.00 126.10   52
  44  ω   -112.00 -87.00   0.50    0.33    --  -74.18-142.00  62.00   50
  45  ω   -113.00 -88.00   0.50    0.33    --  -75.51-142.00  62.00   50
  46  ω   -119.00 -94.00   0.50    0.33    --  -75.51-130.00-125.00   50
  47  ω   -114.00 -74.00   0.50    0.33    --  -74.18-130.00-125.00   80

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            11895
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.170
_diffrn_reflns_theta_max         74.451
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2209
_reflns_number_gt                1871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+0.4976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2209
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.09501(6) 0.0844(2) 0.26551(10) 0.0346(3) Uani 1 1 d . . . . .
F2 F 0.20974(6) 0.3160(3) 0.28859(10) 0.0368(3) Uani 1 1 d . . . . .
F3 F 0.22941(6) 0.7550(3) 0.14051(11) 0.0366(3) Uani 1 1 d . . . . .
F4 F 0.13641(6) 0.9456(3) -0.04289(10) 0.0356(3) Uani 1 1 d . . . . .
F5 F 0.02090(6) 0.9240(2) -0.15547(10) 0.0334(3) Uani 1 1 d . . . . .
F6 F 0.35931(6) -0.4080(3) 0.32319(10) 0.0379(3) Uani 1 1 d . . . . .
F7 F 0.26670(6) -0.1775(3) 0.41194(11) 0.0397(3) Uani 1 1 d . . . . .
F8 F 0.29050(6) 0.2541(3) 0.58159(12) 0.0400(3) Uani 1 1 d . . . . .
F9 F 0.40792(6) 0.4446(3) 0.67297(11) 0.0380(3) Uani 1 1 d . . . . .
F10 F 0.52413(6) 0.4233(2) 0.67510(10) 0.0356(3) Uani 1 1 d . . . . .
C1 C 0.10286(11) 0.2979(4) 0.18819(17) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.16096(11) 0.4128(4) 0.20150(18) 0.0321(5) Uani 1 1 d . . . . .
C3 C 0.17157(10) 0.6371(4) 0.12172(18) 0.0328(5) Uani 1 1 d . . . . .
C4 C 0.12381(11) 0.7326(4) 0.03047(18) 0.0320(5) Uani 1 1 d . . . . .
C5 C 0.06170(10) 0.6188(4) 0.01243(17) 0.0288(4) Uani 1 1 d . . . . .
C6 C 0.01034(10) 0.7136(4) -0.07886(17) 0.0300(4) Uani 1 1 d . . . . .
C7 C -0.05019(10) 0.6050(4) -0.09534(17) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.37349(11) -0.1972(4) 0.40838(17) 0.0336(5) Uani 1 1 d . . . . .
C9 C 0.32629(11) -0.0837(4) 0.45230(18) 0.0354(5) Uani 1 1 d . . . . .
C10 C 0.33884(11) 0.1385(5) 0.54301(18) 0.0352(5) Uani 1 1 d . . . . .
C11 C 0.39856(11) 0.2342(4) 0.58782(17) 0.0333(5) Uani 1 1 d . . . . .
C12 C 0.45017(11) 0.1209(4) 0.54582(17) 0.0321(5) Uani 1 1 d . . . . .
C13 C 0.51228(11) 0.2130(4) 0.58890(16) 0.0319(5) Uani 1 1 d . . . . .
C14 C 0.56278(11) 0.1035(4) 0.54742(17) 0.0310(5) 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
F1 C1 1.347(2) . ?
F2 C2 1.341(2) . ?
F3 C3 1.342(2) . ?
F4 C4 1.348(2) . ?
F5 C6 1.349(2) . ?
F6 C8 1.343(2) . ?
F7 C9 1.341(3) . ?
F8 C10 1.344(3) . ?
F9 C11 1.340(2) . ?
F10 C13 1.347(2) . ?
C1 C2 1.347(3) . ?
C1 C7 1.430(3) 3_565 ?
C2 C3 1.419(3) . ?
C3 C4 1.352(3) . ?
C4 C5 1.420(3) . ?
C5 C6 1.399(3) . ?
C5 C7 1.448(3) 3_565 ?
C6 C7 1.381(3) . ?
C8 C9 1.351(3) . ?
C8 C14 1.427(3) 3_656 ?
C9 C10 1.421(3) . ?
C10 C11 1.353(3) . ?
C11 C12 1.422(3) . ?
C12 C13 1.392(3) . ?
C12 C14 1.448(3) 3_656 ?
C13 C14 1.392(3) . ?

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
F1 C1 C2 118.11(19) . . ?
F1 C1 C7 119.75(19) . 3_565 ?
C2 C1 C7 122.15(18) . 3_565 ?
F2 C2 C1 121.01(18) . . ?
F2 C2 C3 118.87(19) . . ?
C1 C2 C3 120.1(2) . . ?
F3 C3 C4 121.11(18) . . ?
F3 C3 C2 118.57(19) . . ?
C4 C3 C2 120.3(2) . . ?
F4 C4 C3 117.96(19) . . ?
F4 C4 C5 120.21(18) . . ?
C3 C4 C5 121.82(18) . . ?
C6 C5 C4 124.21(18) . . ?
C6 C5 C7 117.6(2) . 3_565 ?
C4 C5 C7 118.17(19) . 3_565 ?
F5 C6 C7 118.24(18) . . ?
F5 C6 C5 117.65(19) . . ?
C7 C6 C5 124.11(18) . . ?
C6 C7 C1 124.30(18) . 3_565 ?
C6 C7 C5 118.28(19) . 3_565 ?
C1 C7 C5 117.42(19) 3_565 3_565 ?
F6 C8 C9 118.3(2) . . ?
F6 C8 C14 120.16(19) . 3_656 ?
C9 C8 C14 121.54(19) . 3_656 ?
F7 C9 C8 121.12(18) . . ?
F7 C9 C10 118.4(2) . . ?
C8 C9 C10 120.5(2) . . ?
F8 C10 C11 120.95(19) . . ?
F8 C10 C9 119.0(2) . . ?
C11 C10 C9 120.1(2) . . ?
F9 C11 C10 117.8(2) . . ?
F9 C11 C12 120.3(2) . . ?
C10 C11 C12 121.89(19) . . ?
C13 C12 C11 123.93(19) . . ?
C13 C12 C14 118.1(2) . 3_656 ?
C11 C12 C14 118.0(2) . 3_656 ?
F10 C13 C12 117.98(19) . . ?
F10 C13 C14 118.03(19) . . ?
C12 C13 C14 123.98(18) . . ?
C13 C14 C8 124.07(19) . 3_656 ?
C13 C14 C12 117.9(2) . 3_656 ?
C8 C14 C12 118.0(2) 3_656 3_656 ?

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 0.5(3) . . . . ?
C7 C1 C2 F2 -179.34(16) 3_565 . . . ?
F1 C1 C2 C3 179.63(16) . . . . ?
C7 C1 C2 C3 -0.2(3) 3_565 . . . ?
F2 C2 C3 F3 -3.5(3) . . . . ?
C1 C2 C3 F3 177.36(17) . . . . ?
F2 C2 C3 C4 177.81(17) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
F3 C3 C4 F4 1.5(3) . . . . ?
C2 C3 C4 F4 -179.87(17) . . . . ?
F3 C3 C4 C5 -177.33(17) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
F4 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 178.69(18) . . . . ?
F4 C4 C5 C7 -178.59(16) . . . 3_565 ?
C3 C4 C5 C7 0.2(3) . . . 3_565 ?
C4 C5 C6 F5 0.9(3) . . . . ?
C7 C5 C6 F5 179.41(15) 3_565 . . . ?
C4 C5 C6 C7 -179.20(18) . . . . ?
C7 C5 C6 C7 -0.7(3) 3_565 . . . ?
F5 C6 C7 C1 -0.4(3) . . . 3_565 ?
C5 C6 C7 C1 179.73(17) . . . 3_565 ?
F5 C6 C7 C5 -179.41(15) . . . 3_565 ?
C5 C6 C7 C5 0.7(3) . . . 3_565 ?
F6 C8 C9 F7 -0.2(3) . . . . ?
C14 C8 C9 F7 -178.62(17) 3_656 . . . ?
F6 C8 C9 C10 179.64(17) . . . . ?
C14 C8 C9 C10 1.2(3) 3_656 . . . ?
F7 C9 C10 F8 -2.5(3) . . . . ?
C8 C9 C10 F8 177.65(18) . . . . ?
F7 C9 C10 C11 178.57(18) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
F8 C10 C11 F9 0.9(3) . . . . ?
C9 C10 C11 F9 179.82(17) . . . . ?
F8 C10 C11 C12 -178.19(16) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
F9 C11 C12 C13 0.7(3) . . . . ?
C10 C11 C12 C13 179.80(18) . . . . ?
F9 C11 C12 C14 -179.21(16) . . . 3_656 ?
C10 C11 C12 C14 -0.1(3) . . . 3_656 ?
C11 C12 C13 F10 -0.4(3) . . . . ?
C14 C12 C13 F10 179.56(16) 3_656 . . . ?
C11 C12 C13 C14 -179.65(17) . . . . ?
C14 C12 C13 C14 0.3(3) 3_656 . . . ?
F10 C13 C14 C8 0.9(3) . . . 3_656 ?
C12 C13 C14 C8 -179.87(18) . . . 3_656 ?
F10 C13 C14 C12 -179.56(16) . . . 3_656 ?
C12 C13 C14 C12 -0.3(3) . . . 3_656 ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_chemical_properties_physical    Oxygen-sensitive
####################################################################### 
# 
# 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_TetDFA_Cocrystal_100K
_database_code_depnum_ccdc_archive 'CCDC 2293631'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details


loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2y (K.Radacki, 2005-22)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'tetracene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C18 H12'
_chemical_formula_sum            'C32 H12 F10'
_chemical_formula_weight         586.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.9115(2)
_cell_length_b                   7.1394(3)
_cell_length_c                   12.1965(5)
_cell_angle_alpha                80.570(3)
_cell_angle_beta                 73.691(3)
_cell_angle_gamma                84.021(3)
_cell_volume                     568.73(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5292
_cell_measurement_theta_min      3.7930
_cell_measurement_theta_max      74.1580


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    1.383
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 1 0.0490
2 0 -1 0.0416
0 1 0 0.0139
0 -1 0 0.0390
0 0 1 0.0087
0 0 -1 0.0107
0 -1 -1 0.0316
2 2 1 0.0440
1 1 1 0.0427

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     42.00  74.00   0.50    0.06    --   32.00  58.00-140.49   64
   2  ω     57.00  84.00   0.50    0.06    --   79.25  14.00 -58.91   54
   3  ω     47.00  79.00   0.50    0.06    --   36.00  55.00  75.52   64
   4  ω     40.00  72.00   0.50    0.06    --   32.00  66.00 126.11   64
   5  ω     45.00  90.00   0.50    0.06    --   79.25   6.00 162.79   90
   6  ω     50.00 113.00   0.50    0.06    --   79.25  -1.00  70.58  126
   7  ω     33.00 106.00   0.50    0.06    --   76.67-126.00  60.00  146
   8  ω     33.00 106.00   0.50    0.06    --   76.67-126.00 120.00  146
   9  ω     33.00 106.00   0.50    0.06    --   76.67-126.00 150.00  146
  10  ω     33.00 106.00   0.50    0.06    --   76.67-126.00   0.00  146
  11  ω     33.00 106.00   0.50    0.06    --   76.67-126.00 -30.00  146
  12  ω     33.00 106.00   0.50    0.06    --   76.67-126.00 -60.00  146
  13  ω     39.00  85.00   0.50    0.06    --   76.67 -95.00-120.00   92
  14  ω     33.00 106.00   0.50    0.06    --   76.67-126.00-180.00  146
  15  ω     33.00 106.00   0.50    0.06    --   76.67-126.00-150.00  146
  16  ω   -123.00 -40.00   0.50    0.06    --  -77.75 153.00-131.79  166
  17  ω   -103.00 -30.00   0.50    0.06    --  -74.18 126.00 -60.00  146
  18  ω    -75.00 -34.00   0.50    0.06    --  -77.75 126.00 -17.39   82
  19  ω   -101.00 -34.00   0.50    0.06    --  -77.75 115.00 -31.25  134
  20  ω   -105.00 -34.00   0.50    0.06    --  -77.75 123.00  33.57  142
  21  ω   -103.00 -30.00   0.50    0.06    --  -74.18 126.00  60.00  146
  22  ω   -102.00 -60.00   0.50    0.06    --  -77.75 137.00  65.23   84
  23  ω   -103.00 -30.00   0.50    0.06    --  -74.18 126.00 150.00  146
  24  ω   -101.00 -34.00   0.50    0.06    --  -77.75 115.00 158.10  134
  25  ω   -100.00 -74.00   0.50    0.06    --  -77.75 113.00 167.89   52
  26  ω    -73.00 -40.00   0.50    0.06    --  -77.75  96.00  47.79   66
  27  ω    -70.00 -39.00   0.50    0.06    --  -77.75  69.00  -2.37   62
  28  ω    -99.00 -35.00   0.50    0.06    --  -77.75 112.00-157.71  128
  29  ω   -111.00 -37.00   0.50    0.06    --  -74.18   0.00-120.00  148
  30  ω   -108.00 -77.00   0.50    0.06    --  -72.00 -74.00 -97.90   62
  31  ω   -114.00 -89.00   0.50    0.06    --  -77.75 -67.00-171.50   50
  32  ω    -85.00 -53.00   0.50    0.06    --  -44.00 -63.00 -96.97   64
  33  ω   -115.00 -88.00   0.50    0.06    --  -77.75 -60.00-113.53   54
  34  ω   -108.00 -76.00   0.50    0.06    --  -68.00 -66.00  11.18   64
  35  ω   -119.00 -87.00   0.50    0.06    --  -77.75 -60.00  -7.23   64
  36  ω   -121.00 -88.00   0.50    0.06    --  -77.75 -53.00 -51.43   66
  37  ω   -122.00 -96.00   0.50    0.06    --  -77.75 -46.00 -49.67   52
  38  ω   -119.00 -87.00   0.50    0.06    --  -77.75 -62.00  34.58   64
  39  ω   -124.00 -91.00   0.50    0.06    --  -77.75 -38.00  76.80   66
  40  ω   -121.00 -44.00   0.50    0.06    --  -75.71 -15.00 -30.00  154
  41  ω   -120.00 -66.00   0.50    0.06    --  -77.75 -23.00 102.38  108
  42  ω    -92.00 -60.00   0.50    0.06    --  -52.00 -66.00 149.43   64
  43  ω   -113.00 -79.00   0.50    0.06    --  -77.75 -81.00 178.95   68
  44  ω   -118.00 -73.00   0.50    0.06    --  -74.18-126.00 -60.00   90

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            11621
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.814
_diffrn_reflns_theta_max         74.390
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2295
_reflns_number_gt                1844
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.0228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24588(12) 0.66566(12) 0.78352(7) 0.0256(2) Uani 1 1 d . . . . .
F2 F 0.26472(12) 0.34642(12) 0.93096(7) 0.0275(2) Uani 1 1 d . . . . .
F3 F 0.43511(11) 0.01775(12) 0.85555(7) 0.0268(2) Uani 1 1 d . . . . .
F4 F 0.60706(11) 0.00356(11) 0.63063(7) 0.0232(2) Uani 1 1 d . . . . .
F5 F 0.68885(11) 0.17258(11) 0.42437(7) 0.0216(2) Uani 1 1 d . . . . .
C1 C 0.33226(19) 0.5055(2) 0.74124(12) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.34043(19) 0.3453(2) 0.81692(11) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.43229(19) 0.17443(19) 0.77736(12) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.51646(18) 0.16844(19) 0.66352(12) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.51140(18) 0.33235(19) 0.57996(11) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.59400(18) 0.33420(19) 0.46177(12) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.58631(18) 0.49352(19) 0.37967(11) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.80199(19) 0.4350(2) 0.84092(12) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.748467 0.551735 0.868524 0.027 Uiso 1 1 calc R U . . .
C9 C 0.8026(2) 0.2727(2) 0.91752(12) 0.0257(3) Uani 1 1 d . . . . .
H9 H 0.749699 0.277359 0.997892 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8821(2) 0.0959(2) 0.87761(12) 0.0245(3) Uani 1 1 d . . . . .
H10 H 0.879975 -0.016305 0.931825 0.029 Uiso 1 1 calc R U . . .
C11 C 0.96055(19) 0.0858(2) 0.76357(12) 0.0215(3) Uani 1 1 d . . . . .
H11 H 1.014382 -0.032935 0.738920 0.026 Uiso 1 1 calc R U . . .
C12 C 0.96331(18) 0.25294(19) 0.67929(11) 0.0179(3) Uani 1 1 d . . . . .
C13 C 1.04088(18) 0.24604(19) 0.56198(11) 0.0181(3) Uani 1 1 d . . . . .
H13 H 1.094834 0.128076 0.536219 0.022 Uiso 1 1 calc R U . . .
C14 C 1.04135(18) 0.41083(18) 0.47991(11) 0.0168(3) Uani 1 1 d . . . . .
C15 C 1.11897(18) 0.40524(19) 0.36082(11) 0.0182(3) Uani 1 1 d . . . . .
H15 H 1.172658 0.287658 0.334441 0.022 Uiso 1 1 calc R U . . .
C16 C 1.11883(18) 0.56861(19) 0.28059(11) 0.0186(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3443(16) . ?
F2 C2 1.3426(15) . ?
F3 C3 1.3482(15) . ?
F4 C4 1.3412(15) . ?
F5 C6 1.3477(15) . ?
C1 C2 1.3544(19) . ?
C1 C7 1.4223(19) 2_666 ?
C2 C3 1.408(2) . ?
C3 C4 1.3523(19) . ?
C4 C5 1.4248(18) . ?
C5 C6 1.3919(19) . ?
C5 C7 1.4432(19) 2_666 ?
C6 C7 1.3940(19) . ?
C8 C9 1.3644(19) . ?
C8 C16 1.4321(18) 2_766 ?
C8 H8 0.9500 . ?
C9 C10 1.428(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.355(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.4396(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3870(19) . ?
C12 C16 1.4431(19) 2_766 ?
C13 C14 1.4139(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4057(19) . ?
C14 C14 1.443(2) 2_766 ?
C15 C16 1.3944(19) . ?
C15 H15 0.9500 . ?

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
F1 C1 C2 118.12(12) . . ?
F1 C1 C7 120.46(12) . 2_666 ?
C2 C1 C7 121.42(13) . 2_666 ?
F2 C2 C1 120.92(13) . . ?
F2 C2 C3 118.64(12) . . ?
C1 C2 C3 120.43(12) . . ?
F3 C3 C4 120.92(13) . . ?
F3 C3 C2 118.48(12) . . ?
C4 C3 C2 120.60(13) . . ?
F4 C4 C3 118.25(12) . . ?
F4 C4 C5 120.36(12) . . ?
C3 C4 C5 121.39(13) . . ?
C6 C5 C4 123.91(13) . . ?
C6 C5 C7 118.10(13) . 2_666 ?
C4 C5 C7 118.00(13) . 2_666 ?
F5 C6 C5 118.04(12) . . ?
F5 C6 C7 117.92(12) . . ?
C5 C6 C7 124.03(13) . . ?
C6 C7 C1 124.00(13) . 2_666 ?
C6 C7 C5 117.87(13) . 2_666 ?
C1 C7 C5 118.13(12) 2_666 2_666 ?
C9 C8 C16 120.76(14) . 2_766 ?
C9 C8 H8 119.6 . . ?
C16 C8 H8 119.6 2_766 . ?
C8 C9 C10 120.40(13) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.96(13) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.77(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 121.89(13) . . ?
C13 C12 C16 119.78(12) . 2_766 ?
C11 C12 C16 118.33(12) . 2_766 ?
C12 C13 C14 121.40(13) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 121.85(12) . . ?
C15 C14 C14 119.36(15) . 2_766 ?
C13 C14 C14 118.79(15) . 2_766 ?
C16 C15 C14 121.40(13) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C8 121.96(13) . 2_766 ?
C15 C16 C12 119.27(13) . 2_766 ?
C8 C16 C12 118.77(12) 2_766 2_766 ?

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 -0.12(19) . . . . ?
C7 C1 C2 F2 179.39(10) 2_666 . . . ?
F1 C1 C2 C3 -178.93(11) . . . . ?
C7 C1 C2 C3 0.6(2) 2_666 . . . ?
F2 C2 C3 F3 1.89(18) . . . . ?
C1 C2 C3 F3 -179.27(11) . . . . ?
F2 C2 C3 C4 -177.79(11) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
F3 C3 C4 F4 -1.53(19) . . . . ?
C2 C3 C4 F4 178.14(11) . . . . ?
F3 C3 C4 C5 178.94(10) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
F4 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C6 -179.48(11) . . . . ?
F4 C4 C5 C7 -179.38(10) . . . 2_666 ?
C3 C4 C5 C7 0.1(2) . . . 2_666 ?
C4 C5 C6 F5 -1.7(2) . . . . ?
C7 C5 C6 F5 178.66(10) 2_666 . . . ?
C4 C5 C6 C7 178.89(11) . . . . ?
C7 C5 C6 C7 -0.7(2) 2_666 . . . ?
F5 C6 C7 C1 1.7(2) . . . 2_666 ?
C5 C6 C7 C1 -178.89(11) . . . 2_666 ?
F5 C6 C7 C5 -178.66(10) . . . 2_666 ?
C5 C6 C7 C5 0.7(2) . . . 2_666 ?
C16 C8 C9 C10 -0.1(2) 2_766 . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C10 C11 C12 C13 -179.33(11) . . . . ?
C10 C11 C12 C16 0.24(19) . . . 2_766 ?
C11 C12 C13 C14 179.49(11) . . . . ?
C16 C12 C13 C14 -0.1(2) 2_766 . . . ?
C12 C13 C14 C15 -179.78(10) . . . . ?
C12 C13 C14 C14 -0.1(2) . . . 2_766 ?
C13 C14 C15 C16 -179.96(11) . . . . ?
C14 C14 C15 C16 0.4(2) 2_766 . . . ?
C14 C15 C16 C8 179.80(11) . . . 2_766 ?
C14 C15 C16 C12 -0.2(2) . . . 2_766 ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_PyrDFA_300K
_database_code_depnum_ccdc_archive 'CCDC 2293636'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'pyrene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C16 H10'
_chemical_formula_sum            'C30 H10 F10'
_chemical_formula_weight         560.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.35337(14)
_cell_length_b                   8.5989(2)
_cell_length_c                   17.4368(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.9800(19)
_cell_angle_gamma                90
_cell_volume                     1101.89(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6371
_cell_measurement_theta_min      5.7280
_cell_measurement_theta_max      74.7760


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.573
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.161
_exptl_absorpt_coefficient_mu    1.395
_shelx_estimated_absorpt_T_min   0.504
_shelx_estimated_absorpt_T_max   0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) Empirical 
absorption correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 2 0.0833
0 1 0 0.1374
0 2 -5 0.0433
0 -2 5 0.1175
-1 0 -2 0.0810
0 -1 0 0.1561
0 -2 -1 0.1540
0 0 -1 0.0120

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      299.74(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_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  77.00   0.50    0.05    --   58.71-109.00-159.00  130
   2  ω    -78.00 -13.00   0.50    0.05    --  -60.26 109.00 -63.00  130
   3  ω    -87.00 -23.00   0.50    0.05    --  -69.77 109.00 -63.00  128
   4  ω    -94.00 -29.00   0.50    0.05    --  -76.33 109.00 -63.00  130
   5  ω     35.00 100.00   0.50    0.05    --   82.37-109.00-159.00  130
   6  ω      8.00  42.00   0.50    0.05    --   -2.00  65.00-174.00   68
   7  ω     60.00  88.00   0.50    0.05    --   46.00  51.00 -79.70   56
   8  ω    -94.00 -68.00   0.50    0.05    --  -54.00 -43.00-168.55   52
   9  ω   -101.00 -76.00   0.50    0.05    --  -54.00 -52.00 -78.66   50
  10  ω     24.00  82.00   0.50    0.05    --   71.32-109.00-159.00  116
  11  ω   -127.00 -97.00   0.50    0.05    --  -79.50 -49.00  86.07   60
  12  ω   -123.00 -93.00   0.50    0.05    --  -79.50 -57.00  -7.71   60
  13  ω   -130.00 -95.00   0.50    0.05    --  -79.50 -43.00   8.38   70
  14  ω   -125.00-100.00   0.50    0.05    --  -79.50 -62.00-128.03   50
  15  ω     80.00 133.00   0.50    0.05    --   82.37  15.00-180.00  106
  16  ω     74.00 100.00   0.50    0.05    --   82.37-112.00  90.00   52
  17  ω     58.00  83.00   0.50    0.05    --   82.37 -95.00 -90.00   50
  18  ω     81.00 133.00   0.50    0.05    --   82.37  15.00 120.00  104
  19  ω     92.00 127.00   0.50    0.05    --   82.37  15.00   0.00   70
  20  ω     60.00 100.00   0.50    0.05    --   82.37-112.00 -60.00   80
  21  ω    104.00 131.00   0.50    0.05    --   85.25  14.00 -43.89   54
  22  ω     68.00  97.00   0.50    0.05    --   85.25  14.00 -43.89   58
  23  ω     43.00  83.00   0.50    0.05    --   85.25 -94.00  35.75   80
  24  ω     62.00  88.00   0.50    0.05    --   85.25 -91.00  62.65   52
  25  ω     52.00  78.00   0.50    0.05    --   85.25 -79.00 162.39   52
  26  ω     43.00  92.00   0.50    0.05    --   85.25 -94.00-127.45   98
  27  ω    100.00 125.00   0.50    0.05    --   85.25  64.00-120.29   50
  28  ω    106.00 133.00   0.50    0.05    --   85.25 114.00 144.11   54
  29  ω    101.00 135.00   0.50    0.05    --   85.25  46.00-159.25   68
  30  ω     43.00  77.00   0.50    0.05    --   85.25-123.00 153.34   68
  31  ω     39.00  69.00   0.50    0.05    --   85.25-106.00   7.14   60
  32  ω     64.00  90.00   0.50    0.05    --   85.25-106.00 -40.29   52
  33  ω     39.00 106.00   0.50    0.05    --   85.25-138.00-103.88  134
  34  ω     51.00  77.00   0.50    0.05    --   85.25 -85.00 -28.49   52
  35  ω     51.00  92.00   0.50    0.05    --   85.25-105.00  21.95   82

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            11875
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.076
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2232
_reflns_number_gt                1704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.08975(19) -0.14211(18) 0.30310(7) 0.0764(5) Uani 1 1 d . . . . .
F2 F 0.2051(2) 0.1163(2) 0.23531(8) 0.0899(5) Uani 1 1 d . . . . .
F3 F 0.2262(2) 0.38776(19) 0.31198(9) 0.0900(5) Uani 1 1 d . . . . .
F4 F 0.1378(2) 0.40622(15) 0.45885(9) 0.0795(5) Uani 1 1 d . . . . .
F5 F 0.02710(18) 0.27286(15) 0.57793(7) 0.0701(4) Uani 1 1 d . . . . .
C1 C 0.6208(4) 0.1088(5) 0.34041(17) 0.0946(11) Uani 1 1 d . . . . .
H1 H 0.638433 0.078538 0.290001 0.114 Uiso 1 1 calc R U . . .
C2 C 0.6537(4) 0.2569(5) 0.3636(2) 0.1028(12) Uani 1 1 d . . . . .
H2 H 0.694408 0.326956 0.327421 0.123 Uiso 1 1 calc R U . . .
C3 C 0.6315(4) 0.3103(4) 0.4363(2) 0.1015(11) Uani 1 1 d . . . . .
H3 H 0.657390 0.413474 0.448412 0.122 Uiso 1 1 calc R U . . .
C4 C 0.5698(3) 0.2097(3) 0.49201(16) 0.0722(7) Uani 1 1 d . . . . .
C5 C 0.5406(4) 0.2551(3) 0.57053(19) 0.0851(9) Uani 1 1 d . . . . .
H5 H 0.564443 0.357027 0.585668 0.102 Uiso 1 1 calc R U . . .
C6 C 0.4801(4) 0.1539(4) 0.62154(18) 0.0920(10) Uani 1 1 d . . . . .
H6 H 0.462485 0.187981 0.671357 0.110 Uiso 1 1 calc R U . . .
C7 C 0.5575(3) -0.0003(4) 0.39638(13) 0.0720(7) Uani 1 1 d . . . . .
C8 C 0.5313(2) 0.0511(3) 0.47147(11) 0.0510(5) Uani 1 1 d . . . . .
C9 C 0.0960(3) -0.0092(3) 0.34340(11) 0.0560(5) Uani 1 1 d . . . . .
C10 C 0.1539(3) 0.1203(3) 0.30905(12) 0.0647(6) Uani 1 1 d . . . . .
C11 C 0.1673(3) 0.2609(3) 0.34878(13) 0.0629(6) Uani 1 1 d . . . . .
C12 C 0.1226(3) 0.2691(2) 0.42307(13) 0.0572(5) Uani 1 1 d . . . . .
C13 C 0.0608(2) 0.1364(2) 0.46306(11) 0.0469(5) Uani 1 1 d . . . . .
C14 C 0.0143(2) 0.1386(2) 0.53940(11) 0.0489(5) Uani 1 1 d . . . . .
C15 C -0.0464(2) 0.0080(2) 0.57811(10) 0.0472(5) 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
F1 C9 1.341(3) . ?
F2 C10 1.353(3) . ?
F3 C11 1.345(2) . ?
F4 C12 1.337(2) . ?
F5 C14 1.338(2) . ?
C1 C2 1.355(5) . ?
C1 C7 1.443(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C8 1.436(3) . ?
C4 C5 1.447(4) . ?
C5 C6 1.332(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) 3_656 ?
C6 H6 0.9300 . ?
C7 C8 1.402(3) . ?
C8 C8 1.416(4) 3_656 ?
C9 C10 1.341(3) . ?
C9 C15 1.428(3) 3_556 ?
C10 C11 1.395(3) . ?
C11 C12 1.349(3) . ?
C12 C13 1.420(3) . ?
C13 C14 1.386(3) . ?
C13 C15 1.436(3) 3_556 ?
C14 C15 1.391(3) . ?

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 C7 117.9(3) . . ?
C2 C1 H1 121.1 . . ?
C7 C1 H1 121.1 . . ?
C1 C2 C3 124.7(3) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C8 118.9(3) . . ?
C3 C4 C5 123.8(3) . . ?
C8 C4 C5 117.3(2) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 122.8(3) . 3_656 ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 3_656 . ?
C6 C7 C8 118.7(3) 3_656 . ?
C6 C7 C1 122.3(3) 3_656 . ?
C8 C7 C1 119.0(3) . . ?
C7 C8 C8 121.2(3) . 3_656 ?
C7 C8 C4 120.0(2) . . ?
C8 C8 C4 118.7(2) 3_656 . ?
C10 C9 F1 118.6(2) . . ?
C10 C9 C15 121.2(2) . 3_556 ?
F1 C9 C15 120.2(2) . 3_556 ?
C9 C10 F2 120.4(2) . . ?
C9 C10 C11 121.1(2) . . ?
F2 C10 C11 118.5(2) . . ?
F3 C11 C12 120.6(2) . . ?
F3 C11 C10 119.0(2) . . ?
C12 C11 C10 120.5(2) . . ?
F4 C12 C11 118.4(2) . . ?
F4 C12 C13 120.19(19) . . ?
C11 C12 C13 121.4(2) . . ?
C14 C13 C12 123.65(19) . . ?
C14 C13 C15 118.39(18) . 3_556 ?
C12 C13 C15 117.96(18) . 3_556 ?
F5 C14 C13 118.61(18) . . ?
F5 C14 C15 118.10(18) . . ?
C13 C14 C15 123.29(18) . . ?
C14 C15 C9 123.77(19) . 3_556 ?
C14 C15 C13 118.31(17) . 3_556 ?
C9 C15 C13 117.92(19) 3_556 3_556 ?

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
C7 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C8 0.1(3) . . . . ?
C2 C3 C4 C5 -179.6(2) . . . . ?
C3 C4 C5 C6 179.6(2) . . . . ?
C8 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . 3_656 ?
C2 C1 C7 C6 179.9(2) . . . 3_656 ?
C2 C1 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C8 0.4(3) 3_656 . . 3_656 ?
C1 C7 C8 C8 179.8(2) . . . 3_656 ?
C6 C7 C8 C4 179.74(19) 3_656 . . . ?
C1 C7 C8 C4 -0.9(3) . . . . ?
C3 C4 C8 C7 0.6(3) . . . . ?
C5 C4 C8 C7 -179.74(18) . . . . ?
C3 C4 C8 C8 179.9(2) . . . 3_656 ?
C5 C4 C8 C8 -0.4(3) . . . 3_656 ?
F1 C9 C10 F2 -0.1(3) . . . . ?
C15 C9 C10 F2 178.16(17) 3_556 . . . ?
F1 C9 C10 C11 -178.44(17) . . . . ?
C15 C9 C10 C11 -0.2(3) 3_556 . . . ?
C9 C10 C11 F3 179.94(18) . . . . ?
F2 C10 C11 F3 1.6(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
F2 C10 C11 C12 -178.10(18) . . . . ?
F3 C11 C12 F4 0.2(3) . . . . ?
C10 C11 C12 F4 179.89(18) . . . . ?
F3 C11 C12 C13 -179.74(16) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
F4 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 179.62(17) . . . . ?
F4 C12 C13 C15 179.84(16) . . . 3_556 ?
C11 C12 C13 C15 -0.2(3) . . . 3_556 ?
C12 C13 C14 F5 0.3(3) . . . . ?
C15 C13 C14 F5 -179.85(14) 3_556 . . . ?
C12 C13 C14 C15 179.87(16) . . . . ?
C15 C13 C14 C15 -0.3(3) 3_556 . . . ?
F5 C14 C15 C9 0.0(3) . . . 3_556 ?
C13 C14 C15 C9 -179.53(16) . . . 3_556 ?
F5 C14 C15 C13 179.86(14) . . . 3_556 ?
C13 C14 C15 C13 0.3(3) . . . 3_556 ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.041



#=======================================================END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_ADFA_100K
_database_code_depnum_ccdc_archive 'CCDC 2293628'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

_audit_creation_date             2021-07-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de
_chemical_name_common            ?
_chemical_name_systematic        'anthracene decafluoroanthracene'
_chemical_formula_moiety         'C14 F10, C14 H10'
_chemical_formula_sum            'C28 H10 F10'
_chemical_formula_weight         536.36
_chemical_oxdiff_usercomment     FR320
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0884(3)
_cell_length_b                   7.3423(2)
_cell_length_c                   10.3604(3)
_cell_angle_alpha                85.427(3)
_cell_angle_beta                 74.157(3)
_cell_angle_gamma                78.753(3)
_cell_volume                     508.56(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6406
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1490
_cell_measurement_theta_min      4.4470
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.665
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.109a (Rigaku Oxford Diffraction, 2021) Empirical
absorption correction using spherical harmonics, implemented in 
SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_min         4.438
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -71.00  25.00   0.50    0.14    --  -47.71  78.00 -10.00  192
  2  ω    -26.00  28.00   0.50    0.14    --  -47.71  19.00 -60.00  108
  3  ω     25.00 120.00   0.50    0.14    --   47.71  78.00 -10.00  190
  4  ω    -26.00  28.00   0.50    0.14    --  -47.71  19.00   0.00  108
  5  ω     25.00 120.00   0.50    0.14    --   47.71  77.00-180.00  190
  6  ω     25.00 120.00   0.50    0.14    --   47.71  77.00 -90.00  190
  7  ω     90.00 178.00   0.50    0.57    --  113.25  78.00 -10.00  176
  8  ω     97.00 178.00   0.50    0.57    --  113.25  61.00 -60.00  162
  9  ω    101.00 178.00   0.50    0.57    --  113.25  45.00 -30.00  154
 10  ω    101.00 178.00   0.50    0.57    --  113.25  30.00 -60.00  154
 11  ω    101.00 178.00   0.50    0.57    --  113.25  45.00 -60.00  154
 12  ω    101.00 178.00   0.50    0.57    --  113.25  30.00  60.00  154
 13  ω     97.00 178.00   0.50    0.57    --  113.25  61.00-180.00  162
 14  ω     91.00 178.00   0.50    0.57    --  113.25  77.00-120.00  174
 15  ω     92.00 178.00   0.50    0.57    --  113.25 125.00-180.00  172
 16  ω     42.00 106.00   0.50    0.57    --  113.25 -77.00  60.00  128
 17  ω     42.00 106.00   0.50    0.57    --  113.25 -77.00 -90.00  128
 18  ω     42.00 111.00   0.50    0.57    --  113.25 -78.00-135.00  138
 19  ω     42.00  71.00   0.50    0.57    --  113.25 -61.00-150.00   58
 20  ω    -24.00  71.00   0.50    0.14    --   47.71 -78.00-135.00  190
 21  ω     42.00  71.00   0.50    0.57    --  113.25 -61.00 -60.00   58
 22  ω     42.00  71.00   0.50    0.57    --  113.25 -61.00  60.00   58
 23  ω     42.00 117.00   0.50    0.57    --  113.25-125.00  60.00  150
 24  ω     42.00 117.00   0.50    0.57    --  113.25-125.00 120.00  150
 25  ω     42.00 117.00   0.50    0.57    --  113.25-125.00  30.00  150
 26  ω     42.00 117.00   0.50    0.57    --  113.25-125.00  90.00  150
 27  ω     42.00 117.00   0.50    0.57    --  113.25-125.00 -60.00  150
 28  ω     42.00 117.00   0.50    0.57    --  113.25-125.00-150.00  150
 29  ω     42.00 117.00   0.50    0.57    --  113.25-125.00-180.00  150
 30  ω     42.00 109.00   0.50    0.57    --  113.25 -94.00-180.00  134
 31  ω     42.00 109.00   0.50    0.57    --  113.25 -94.00-150.00  134
 32  ω     42.00 109.00   0.50    0.57    --  113.25 -94.00 -60.00  134
 33  ω     42.00 109.00   0.50    0.57    --  113.25 -94.00  90.00  134
 34  ω   -120.00 -33.00   0.50    0.14    --  -47.71 -57.00  30.00  174
 35  ω   -120.00 -25.00   0.50    0.14    --  -47.71 -77.00 120.00  190
 36  ω    -91.00 -19.00   0.50    0.57    --  -91.75 125.00  60.00  144
 37  ω   -163.00 -68.00   0.50    0.57    --  -91.75 -78.00-135.00  190
 38  ω   -120.00 -24.00   0.50    0.14    --  -47.71 -78.00-135.00  192
 39  ω   -120.00 -25.00   0.50    0.14    --  -47.71 -77.00 -30.00  190
 40  ω   -120.00 -70.00   0.50    0.14    --  -47.71-125.00 -60.00  100
 41  ω   -120.00 -70.00   0.50    0.14    --  -47.71-125.00-180.00  100
 42  ω    -51.00 -20.00   0.50    0.57    --  -91.75  45.00-180.00   62
 43  ω    -51.00 -20.00   0.50    0.57    --  -91.75  45.00 -90.00   62
 44  ω    -51.00 -20.00   0.50    0.57    --  -91.75  45.00 -60.00   62
 45  ω   -111.00 -19.00   0.50    0.57    --  -91.75  78.00 -10.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1799535000
_diffrn_orient_matrix_UB_12      0.0489812000
_diffrn_orient_matrix_UB_13      0.0371288000
_diffrn_orient_matrix_UB_21      0.1412683000
_diffrn_orient_matrix_UB_22      -0.0985955000
_diffrn_orient_matrix_UB_23      -0.1254785000
_diffrn_orient_matrix_UB_31      -0.0205336000
_diffrn_orient_matrix_UB_32      0.1835239000
_diffrn_orient_matrix_UB_33      -0.0823825000
_diffrn_oxdiff_digest_frames     
;
01a806861f25ec1372c9108cf44db014c7000470483
;
_diffrn_oxdiff_digest_hkl        
;
01be2ca670914f0875884243836e25e347f70c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1854
_reflns_number_total             2073
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.071
_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)+(0.0641P)²+0.0657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and goodness
of fit S are based on F², conventional R-factors R are based on F, with F set to
zero for negative F². The threshold expression of F² > 2sigma(F²) is used 
only for calculating R-factors(gt) etc. and is not relevant to the choice of 
reflections for refinement. R-factors based on F² are statistically about twice 
as large as those based on F, and R-factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
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 0.34282(10) 0.76177(10) 0.21122(7) 0.0279(2) Uani 1 1 d . . . . .
F2 F 0.69451(11) 0.76352(10) 0.03019(7) 0.0291(2) Uani 1 1 d . . . . .
F3 F 1.04124(10) 0.60709(10) 0.08960(7) 0.0278(2) Uani 1 1 d . . . . .
F4 F 1.04140(10) 0.41961(9) 0.32126(7) 0.02590(19) Uani 1 1 d . . . . .
F5 F 0.84672(10) 0.31816(9) 0.55106(7) 0.02420(19) Uani 1 1 d . . . . .
C1 C 0.50286(18) 0.16097(16) 0.24008(12) 0.0238(3) Uani 1 1 d . . . . .
H1 H 0.381391 0.211107 0.217692 0.029 Uiso 1 1 calc R . . . .
C2 C 0.67959(19) 0.16539(16) 0.14676(12) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.680248 0.218177 0.059923 0.031 Uiso 1 1 calc R . . . .
C3 C 0.86344(19) 0.09150(16) 0.17834(12) 0.0255(3) Uani 1 1 d . . . . .
H3 H 0.985702 0.096475 0.112587 0.031 Uiso 1 1 calc R . . . .
C4 C 0.86571(18) 0.01361(15) 0.30213(12) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.989597 -0.035644 0.321436 0.028 Uiso 1 1 calc R . . . .
C5 C 0.68381(17) 0.00528(14) 0.40309(11) 0.0205(3) Uani 1 1 d . . . . .
C6 C 0.68144(17) -0.07455(15) 0.53045(11) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.804150 -0.125125 0.551021 0.025 Uiso 1 1 calc R . . . .
C7 C 0.50208(17) -0.08162(14) 0.62843(12) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.51045(18) 0.67979(15) 0.24418(12) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.68718(19) 0.68200(15) 0.15224(12) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.86769(18) 0.59638(15) 0.18165(12) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.86637(18) 0.50462(15) 0.30065(12) 0.0219(3) Uani 1 1 d . . . . .
C12 C 0.68508(17) 0.49832(14) 0.40140(11) 0.0201(3) Uani 1 1 d . . . . .
C13 C 0.67568(17) 0.40935(15) 0.52660(12) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.49894(17) 0.40795(14) 0.62672(12) 0.0204(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.3419(14) . ?
F2 C9 1.3474(13) . ?
F3 C10 1.3469(13) . ?
F4 C11 1.3401(14) . ?
F5 C13 1.3441(13) . ?
C1 H1 0.9500 . ?
C1 C2 1.3618(17) . ?
C1 C7 1.4324(16) 2_656 ?
C2 H2 0.9500 . ?
C2 C3 1.4242(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3649(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.4299(17) . ?
C5 C6 1.3977(16) . ?
C5 C7 1.4404(17) 2_656 ?
C6 H6 0.9500 . ?
C6 C7 1.4008(17) . ?
C8 C9 1.3531(18) . ?
C8 C14 1.4279(16) 2_666 ?
C9 C10 1.4120(17) . ?
C10 C11 1.3556(17) . ?
C11 C12 1.4234(17) . ?
C12 C13 1.3958(17) . ?
C12 C14 1.4440(17) 2_666 ?
C13 C14 1.3927(18) . ?

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 H1 119.6 . . ?
C2 C1 C7 120.80(11) . 2_656 ?
C7 C1 H1 119.6 2_656 . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.52(11) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.65(11) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.77(11) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C7 118.57(11) . 2_656 ?
C6 C5 C4 122.06(11) . . ?
C6 C5 C7 119.37(11) . 2_656 ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.44(11) . . ?
C7 C6 H6 119.3 . . ?
C1 C7 C5 118.68(11) 2_656 2_656 ?
C6 C7 C1 122.13(11) . 2_656 ?
C6 C7 C5 119.19(11) . 2_656 ?
F1 C8 C9 118.42(10) . . ?
F1 C8 C14 120.41(11) . 2_666 ?
C9 C8 C14 121.17(11) . 2_666 ?
F2 C9 C8 120.77(11) . . ?
F2 C9 C10 118.63(11) . . ?
C8 C9 C10 120.60(11) . . ?
F3 C10 C9 118.99(10) . . ?
F3 C10 C11 120.49(11) . . ?
C11 C10 C9 120.52(11) . . ?
F4 C11 C10 118.06(11) . . ?
F4 C11 C12 120.61(10) . . ?
C10 C11 C12 121.33(11) . . ?
C11 C12 C14 118.11(11) . 2_666 ?
C13 C12 C11 123.65(11) . . ?
C13 C12 C14 118.23(12) . 2_666 ?
F5 C13 C12 118.03(11) . . ?
F5 C13 C14 118.28(10) . . ?
C14 C13 C12 123.68(11) . . ?
C8 C14 C12 118.18(11) 2_666 2_666 ?
C13 C14 C8 123.73(11) . 2_666 ?
C13 C14 C12 118.08(11) . 2_666 ?

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 C8 C9 F2 -0.43(17) . . . . ?
F1 C8 C9 C10 -179.48(9) . . . . ?
F2 C9 C10 F3 3.31(16) . . . . ?
F2 C9 C10 C11 -176.62(10) . . . . ?
F3 C10 C11 F4 -2.54(17) . . . . ?
F3 C10 C11 C12 177.36(9) . . . . ?
F4 C11 C12 C13 1.33(19) . . . . ?
F4 C11 C12 C14 -179.81(9) . . . 2_666 ?
F5 C13 C14 C8 2.15(18) . . . 2_666 ?
F5 C13 C14 C12 -178.28(9) . . . 2_666 ?
C1 C2 C3 C4 0.57(18) . . . . ?
C2 C3 C4 C5 -0.33(18) . . . . ?
C3 C4 C5 C6 179.63(10) . . . . ?
C3 C4 C5 C7 -0.27(18) . . . 2_656 ?
C4 C5 C6 C7 179.95(9) . . . . ?
C5 C6 C7 C1 -179.25(9) . . . 2_656 ?
C5 C6 C7 C5 0.15(19) . . . 2_656 ?
C7 C1 C2 C3 -0.19(18) 2_656 . . . ?
C7 C5 C6 C7 -0.15(19) 2_656 . . . ?
C8 C9 C10 F3 -177.61(10) . . . . ?
C8 C9 C10 C11 2.46(18) . . . . ?
C9 C10 C11 F4 177.39(9) . . . . ?
C9 C10 C11 C12 -2.71(18) . . . . ?
C10 C11 C12 C13 -178.56(10) . . . . ?
C10 C11 C12 C14 0.30(18) . . . 2_666 ?
C11 C12 C13 F5 -2.86(18) . . . . ?
C11 C12 C13 C14 177.97(9) . . . . ?
C12 C13 C14 C8 -178.68(9) . . . 2_666 ?
C12 C13 C14 C12 0.9(2) . . . 2_666 ?
C14 C8 C9 F2 179.33(9) 2_666 . . . ?
C14 C8 C9 C10 0.28(19) 2_666 . . . ?
C14 C12 C13 F5 178.29(9) 2_666 . . . ?
C14 C12 C13 C14 -0.9(2) 2_666 . . . ?

_olex2_date_sample_data_collection 2021-06-17
_olex2_date_sample_submission    2021-06-09
_olex2_exptl_crystal_mounting_method 
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id FR320
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.615
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_TriDFA_300K
_database_code_depnum_ccdc_archive 'CCDC 2293639'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details


loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'triphenylene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C18 H12'
_chemical_formula_sum            'C32 H12 F10'
_chemical_formula_weight         586.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.85393(13)
_cell_length_b                   37.9170(8)
_cell_length_c                   9.3367(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.002(2)
_cell_angle_gamma                90
_cell_volume                     2373.37(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    12623
_cell_measurement_theta_min      2.3340
_cell_measurement_theta_max      75.0030


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    1.325
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0747
0 1 0 0.0729
2 -2 -1 0.0883
-2 2 1 0.1014
0 -1 1 0.0773
0 1 -1 0.0073
0 -2 1 0.0695
0 2 -1 0.0150
1 -2 0 0.0951
0 2 1 0.0846
1 0 0 0.0882
1 2 1 0.1001
1 -2 2 0.0843

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      299.68(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     16.00  41.00   0.50    0.05    --    6.00  65.00  29.40   50
   2  ω     99.00 125.00   0.50    0.05    --   85.25  63.00  -8.61   52
   3  ω    101.00 129.00   0.50    0.05    --   85.25  36.00 -41.94   56
   4  ω    102.00 133.00   0.50    0.05    --   85.25  38.00 -16.98   62
   5  ω    101.00 127.00   0.50    0.05    --   85.25  61.00 168.67   52
   6  ω    100.00 125.00   0.50    0.05    --   85.25  64.00 154.01   50
   7  ω    100.00 134.00   0.50    0.05    --   85.25  47.00  51.67   68
   8  ω     78.00 119.00   0.50    0.05    --   82.37  15.00 -60.00   82
   9  ω     75.00 124.00   0.50    0.05    --   82.37  15.00 -90.00   98
  10  ω     44.00  69.00   0.50    0.05    --   85.25 -72.00  73.05   50
  11  ω     48.00  74.00   0.50    0.05    --   85.25-133.00 135.82   52
  12  ω     44.00  85.00   0.50    0.05    --   85.25-124.00 172.09   82
  13  ω     79.00 105.00   0.50    0.05    --   85.25-133.00 135.82   52
  14  ω     39.00  69.00   0.50    0.05    --   85.25-130.00  18.75   60
  15  ω     75.00 100.00   0.50    0.05    --   82.37-112.00  30.00   50
  16  ω     49.00  75.00   0.50    0.05    --   82.37-112.00  90.00   52
  17  ω     36.00 100.00   0.50    0.05    --   85.25-119.00 -62.40  128
  18  ω     43.00  68.00   0.50    0.05    --   82.37-111.00 -52.00   50
  19  ω     33.00  58.00   0.50    0.05    --   71.32-111.00 -52.00   50
  20  ω     37.00  64.00   0.50    0.05    --   58.71-111.00 -52.00   54
  21  ω     58.00  99.00   0.50    0.05    --   85.25-106.00 -13.19   82
  22  ω     60.00  92.00   0.50    0.05    --   85.25 -96.00 -12.02   64
  23  ω     40.00  65.00   0.50    0.05    --   82.37 -95.00 120.00   50
  24  ω     57.00  82.00   0.50    0.05    --   85.25 -86.00 177.20   50
  25  ω     48.00  81.00   0.50    0.05    --   85.25 -85.00  48.14   66
  26  ω     49.00  79.00   0.50    0.05    --   85.25 -82.00   4.14   60
  27  ω     44.00  71.00   0.50    0.05    --   82.37 -95.00 -30.00   54
  28  ω     55.00  81.00   0.50    0.05    --   85.25 -82.00  17.08   52
  29  ω     37.00  86.00   0.50    0.05    --   85.25-119.00-174.10   98
  30  ω    106.00 132.00   0.50    0.05    --   85.25 119.00-127.68   52
  31  ω    -90.00 -47.00   0.50    0.05    --  -76.33 112.00 -30.00   86
  32  ω    -49.00 -19.00   0.50    0.05    --  -60.26 111.00  40.00   60
  33  ω    -80.00 -55.00   0.50    0.05    --  -69.77 111.00  40.00   50
  34  ω    -94.00 -61.00   0.50    0.05    --  -76.33 111.00  40.00   66
  35  ω   -114.00 -83.00   0.50    0.05    --  -66.00 -51.00   4.00   62
  36  ω   -118.00 -92.00   0.50    0.05    --  -79.50 -60.00  -9.50   52
  37  ω   -117.00 -90.00   0.50    0.05    --  -74.00 -57.00 -49.00   54
  38  ω   -124.00 -99.00   0.50    0.05    --  -79.50 -63.00-151.92   50
  39  ω    -94.00 -69.00   0.50    0.05    --  -54.00 -52.00 -50.21   50
  40  ω   -123.00 -96.00   0.50    0.05    --  -79.50-118.00  25.43   54
  41  ω   -125.00-100.00   0.50    0.05    --  -79.50-118.00  -1.15   50
  42  ω   -128.00-102.00   0.50    0.05    --  -79.50-120.00 -91.06   52
  43  ω   -119.00 -93.00   0.50    0.05    --  -79.50-122.00 148.88   52

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            25928
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4834
_reflns_number_gt                3459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.1696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00110(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4834
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.54209(14) 0.38022(3) 0.32748(9) 0.0744(3) Uani 1 1 d . . . . .
F2 F 0.57373(15) 0.45031(3) 0.34850(11) 0.0844(3) Uani 1 1 d . . . . .
F3 F 0.66776(15) 0.48237(2) 0.60933(12) 0.0837(3) Uani 1 1 d . . . . .
F4 F 0.72166(14) 0.44551(2) 0.85800(10) 0.0682(3) Uani 1 1 d . . . . .
F5 F 0.72603(13) 0.38626(2) 0.98368(8) 0.0628(2) Uani 1 1 d . . . . .
F6 F 0.72593(16) 0.32708(3) 1.11105(10) 0.0821(3) Uani 1 1 d . . . . .
F7 F 0.69174(19) 0.25704(3) 1.09022(14) 0.1080(4) Uani 1 1 d . . . . .
F8 F 0.6406(2) 0.22438(3) 0.82929(17) 0.1183(5) Uani 1 1 d . . . . .
F9 F 0.60614(19) 0.26144(3) 0.58106(14) 0.0985(4) Uani 1 1 d . . . . .
F10 F 0.57189(16) 0.32093(3) 0.45525(10) 0.0808(3) Uani 1 1 d . . . . .
C1 C 0.11667(17) 0.38270(4) 0.58819(14) 0.0455(3) Uani 1 1 d . . . . .
C2 C 0.0655(2) 0.36747(5) 0.44810(16) 0.0610(4) Uani 1 1 d . . . . .
H2 H 0.054925 0.343074 0.439696 0.073 Uiso 1 1 calc R U . . .
C3 C 0.0308(2) 0.38759(6) 0.32398(17) 0.0735(5) Uani 1 1 d . . . . .
H3 H -0.003547 0.376824 0.232700 0.088 Uiso 1 1 calc R U . . .
C4 C 0.0466(2) 0.42382(6) 0.33367(17) 0.0725(5) Uani 1 1 d . . . . .
H4 H 0.023096 0.437481 0.249097 0.087 Uiso 1 1 calc R U . . .
C5 C 0.0968(2) 0.43955(5) 0.46784(16) 0.0616(4) Uani 1 1 d . . . . .
H5 H 0.107924 0.463978 0.473306 0.074 Uiso 1 1 calc R U . . .
C6 C 0.13217(17) 0.41973(4) 0.59789(14) 0.0466(3) Uani 1 1 d . . . . .
C7 C 0.18187(18) 0.43683(4) 0.74147(15) 0.0457(3) Uani 1 1 d . . . . .
C8 C 0.1959(2) 0.47373(4) 0.75619(19) 0.0636(4) Uani 1 1 d . . . . .
H8 H 0.174824 0.487633 0.672324 0.076 Uiso 1 1 calc R U . . .
C9 C 0.2397(3) 0.48974(4) 0.8904(2) 0.0737(5) Uani 1 1 d . . . . .
H9 H 0.246103 0.514200 0.896966 0.088 Uiso 1 1 calc R U . . .
C10 C 0.2743(3) 0.46953(4) 1.0159(2) 0.0725(5) Uani 1 1 d . . . . .
H10 H 0.304648 0.480304 1.107353 0.087 Uiso 1 1 calc R U . . .
C11 C 0.2639(2) 0.43364(4) 1.00536(16) 0.0593(4) Uani 1 1 d . . . . .
H11 H 0.289473 0.420257 1.090693 0.071 Uiso 1 1 calc R U . . .
C12 C 0.21575(18) 0.41630(3) 0.86966(14) 0.0442(3) Uani 1 1 d . . . . .
C13 C 0.19980(17) 0.37789(3) 0.85965(14) 0.0429(3) Uani 1 1 d . . . . .
C14 C 0.2315(2) 0.35660(4) 0.98595(16) 0.0542(3) Uani 1 1 d . . . . .
H14 H 0.265460 0.367185 1.077612 0.065 Uiso 1 1 calc R U . . .
C15 C 0.2133(2) 0.32059(4) 0.97683(18) 0.0623(4) Uani 1 1 d . . . . .
H15 H 0.233250 0.307095 1.061825 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1658(2) 0.30440(4) 0.8422(2) 0.0635(4) Uani 1 1 d . . . . .
H16 H 0.153972 0.279987 0.836141 0.076 Uiso 1 1 calc R U . . .
C17 C 0.1358(2) 0.32435(4) 0.71698(18) 0.0557(4) Uani 1 1 d . . . . .
H17 H 0.104663 0.313128 0.626524 0.067 Uiso 1 1 calc R U . . .
C18 C 0.15111(16) 0.36138(3) 0.72193(14) 0.0438(3) Uani 1 1 d . . . . .
C19 C 0.58680(19) 0.39498(4) 0.46069(15) 0.0533(3) Uani 1 1 d . . . . .
C20 C 0.6026(2) 0.43028(4) 0.46971(17) 0.0581(4) Uani 1 1 d . . . . .
C21 C 0.6496(2) 0.44701(4) 0.60597(18) 0.0576(4) Uani 1 1 d . . . . .
C22 C 0.67734(18) 0.42829(4) 0.73086(16) 0.0488(3) Uani 1 1 d . . . . .
C23 C 0.66229(16) 0.39088(3) 0.72830(14) 0.0416(3) Uani 1 1 d . . . . .
C24 C 0.68817(17) 0.37003(4) 0.85359(14) 0.0446(3) Uani 1 1 d . . . . .
C25 C 0.67578(17) 0.33360(4) 0.85109(15) 0.0472(3) Uani 1 1 d . . . . .
C26 C 0.6960(2) 0.31225(4) 0.97847(18) 0.0600(4) Uani 1 1 d . . . . .
C27 C 0.6809(3) 0.27688(5) 0.9690(2) 0.0750(5) Uani 1 1 d . . . . .
C28 C 0.6509(3) 0.26001(4) 0.8329(3) 0.0801(5) Uani 1 1 d . . . . .
C29 C 0.6313(2) 0.27885(4) 0.7088(2) 0.0679(4) Uani 1 1 d . . . . .
C30 C 0.63815(19) 0.31628(4) 0.71121(16) 0.0507(3) Uani 1 1 d . . . . .
C31 C 0.60946(19) 0.33707(4) 0.58608(15) 0.0517(3) Uani 1 1 d . . . . .
C32 C 0.61810(16) 0.37362(4) 0.58866(14) 0.0440(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C19 1.3399(16) . ?
F2 C20 1.3430(16) . ?
F3 C21 1.3462(17) . ?
F4 C22 1.3332(15) . ?
F5 C24 1.3379(14) . ?
F6 C26 1.3360(19) . ?
F7 C27 1.3483(19) . ?
F8 C28 1.3527(19) . ?
F9 C29 1.3423(19) . ?
F10 C31 1.3425(15) . ?
C1 C2 1.4058(18) . ?
C1 C6 1.4098(19) . ?
C1 C18 1.4649(18) . ?
C2 C3 1.366(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.4055(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4641(18) . ?
C7 C12 1.4061(18) . ?
C7 C8 1.407(2) . ?
C8 C9 1.368(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.4046(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.4617(18) . ?
C13 C18 1.4066(17) . ?
C13 C14 1.4082(18) . ?
C14 C15 1.372(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.4080(19) . ?
C17 H17 0.9300 . ?
C19 C20 1.344(2) . ?
C19 C32 1.4225(18) . ?
C20 C21 1.398(2) . ?
C21 C22 1.344(2) . ?
C22 C23 1.4223(18) . ?
C23 C24 1.3923(18) . ?
C23 C32 1.4337(17) . ?
C24 C25 1.3838(19) . ?
C25 C26 1.4214(19) . ?
C25 C30 1.4364(19) . ?
C26 C27 1.347(2) . ?
C27 C28 1.399(3) . ?
C28 C29 1.344(3) . ?
C29 C30 1.420(2) . ?
C30 C31 1.389(2) . ?
C31 C32 1.3870(19) . ?

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 C6 118.01(13) . . ?
C2 C1 C18 122.09(13) . . ?
C6 C1 C18 119.89(12) . . ?
C3 C2 C1 121.72(16) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.19(15) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.77(15) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.63(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.67(13) . . ?
C5 C6 C7 121.32(13) . . ?
C1 C6 C7 120.00(12) . . ?
C12 C7 C8 118.14(13) . . ?
C12 C7 C6 119.99(12) . . ?
C8 C7 C6 121.87(13) . . ?
C9 C8 C7 121.87(15) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.88(15) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.69(15) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 122.06(15) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C7 118.34(13) . . ?
C11 C12 C13 121.64(13) . . ?
C7 C12 C13 120.02(12) . . ?
C18 C13 C14 118.43(12) . . ?
C18 C13 C12 120.16(12) . . ?
C14 C13 C12 121.41(12) . . ?
C15 C14 C13 121.50(14) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.12(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.87(14) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.66(14) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C17 118.42(13) . . ?
C13 C18 C1 119.94(12) . . ?
C17 C18 C1 121.64(13) . . ?
F1 C19 C20 118.29(13) . . ?
F1 C19 C32 120.48(13) . . ?
C20 C19 C32 121.23(13) . . ?
F2 C20 C19 120.97(15) . . ?
F2 C20 C21 118.42(14) . . ?
C19 C20 C21 120.61(13) . . ?
C22 C21 F3 120.65(15) . . ?
C22 C21 C20 120.93(13) . . ?
F3 C21 C20 118.41(14) . . ?
F4 C22 C21 118.60(13) . . ?
F4 C22 C23 120.38(12) . . ?
C21 C22 C23 121.02(13) . . ?
C24 C23 C22 123.78(12) . . ?
C24 C23 C32 118.08(12) . . ?
C22 C23 C32 118.13(12) . . ?
F5 C24 C25 118.29(12) . . ?
F5 C24 C23 117.93(12) . . ?
C25 C24 C23 123.77(12) . . ?
C24 C25 C26 124.01(13) . . ?
C24 C25 C30 118.06(12) . . ?
C26 C25 C30 117.92(13) . . ?
F6 C26 C27 118.35(15) . . ?
F6 C26 C25 120.34(14) . . ?
C27 C26 C25 121.29(16) . . ?
C26 C27 F7 120.69(19) . . ?
C26 C27 C28 120.65(16) . . ?
F7 C27 C28 118.66(16) . . ?
C29 C28 F8 121.0(2) . . ?
C29 C28 C27 120.63(15) . . ?
F8 C28 C27 118.41(18) . . ?
F9 C29 C28 118.41(15) . . ?
F9 C29 C30 120.22(16) . . ?
C28 C29 C30 121.36(16) . . ?
C31 C30 C29 123.73(14) . . ?
C31 C30 C25 118.20(12) . . ?
C29 C30 C25 118.07(14) . . ?
F10 C31 C32 118.09(13) . . ?
F10 C31 C30 118.25(13) . . ?
C32 C31 C30 123.66(13) . . ?
C31 C32 C19 123.78(13) . . ?
C31 C32 C23 118.17(12) . . ?
C19 C32 C23 118.05(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.16(19) . . . . ?
C18 C1 C2 C3 179.04(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C5 C6 C7 -178.70(13) . . . . ?
C2 C1 C6 C5 -0.29(17) . . . . ?
C18 C1 C6 C5 -179.51(10) . . . . ?
C2 C1 C6 C7 178.99(11) . . . . ?
C18 C1 C6 C7 -0.24(17) . . . . ?
C5 C6 C7 C12 179.78(12) . . . . ?
C1 C6 C7 C12 0.52(17) . . . . ?
C5 C6 C7 C8 0.22(19) . . . . ?
C1 C6 C7 C8 -179.03(12) . . . . ?
C12 C7 C8 C9 -0.5(2) . . . . ?
C6 C7 C8 C9 179.10(13) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C7 1.4(2) . . . . ?
C10 C11 C12 C13 -178.36(14) . . . . ?
C8 C7 C12 C11 -0.69(18) . . . . ?
C6 C7 C12 C11 179.74(11) . . . . ?
C8 C7 C12 C13 179.08(11) . . . . ?
C6 C7 C12 C13 -0.49(17) . . . . ?
C11 C12 C13 C18 179.94(11) . . . . ?
C7 C12 C13 C18 0.17(17) . . . . ?
C11 C12 C13 C14 0.21(19) . . . . ?
C7 C12 C13 C14 -179.56(11) . . . . ?
C18 C13 C14 C15 -0.83(19) . . . . ?
C12 C13 C14 C15 178.91(12) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C14 C13 C18 C17 0.18(16) . . . . ?
C12 C13 C18 C17 -179.57(11) . . . . ?
C14 C13 C18 C1 179.86(11) . . . . ?
C12 C13 C18 C1 0.12(16) . . . . ?
C16 C17 C18 C13 0.45(18) . . . . ?
C16 C17 C18 C1 -179.22(11) . . . . ?
C2 C1 C18 C13 -179.27(11) . . . . ?
C6 C1 C18 C13 -0.08(16) . . . . ?
C2 C1 C18 C17 0.40(17) . . . . ?
C6 C1 C18 C17 179.59(11) . . . . ?
F1 C19 C20 F2 0.23(19) . . . . ?
C32 C19 C20 F2 179.71(11) . . . . ?
F1 C19 C20 C21 -179.77(12) . . . . ?
C32 C19 C20 C21 -0.3(2) . . . . ?
F2 C20 C21 C22 179.06(12) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
F2 C20 C21 F3 -1.32(19) . . . . ?
C19 C20 C21 F3 178.68(12) . . . . ?
F3 C21 C22 F4 0.48(19) . . . . ?
C20 C21 C22 F4 -179.90(12) . . . . ?
F3 C21 C22 C23 -178.77(11) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
F4 C22 C23 C24 1.14(18) . . . . ?
C21 C22 C23 C24 -179.62(12) . . . . ?
F4 C22 C23 C32 -178.80(10) . . . . ?
C21 C22 C23 C32 0.43(18) . . . . ?
C22 C23 C24 F5 1.17(17) . . . . ?
C32 C23 C24 F5 -178.88(10) . . . . ?
C22 C23 C24 C25 -179.23(11) . . . . ?
C32 C23 C24 C25 0.71(17) . . . . ?
F5 C24 C25 C26 1.59(18) . . . . ?
C23 C24 C25 C26 -178.00(12) . . . . ?
F5 C24 C25 C30 -179.06(10) . . . . ?
C23 C24 C25 C30 1.35(18) . . . . ?
C24 C25 C26 F6 1.1(2) . . . . ?
C30 C25 C26 F6 -178.25(12) . . . . ?
C24 C25 C26 C27 179.47(13) . . . . ?
C30 C25 C26 C27 0.1(2) . . . . ?
F6 C26 C27 F7 1.3(2) . . . . ?
C25 C26 C27 F7 -177.08(13) . . . . ?
F6 C26 C27 C28 -179.59(14) . . . . ?
C25 C26 C27 C28 2.0(2) . . . . ?
C26 C27 C28 C29 -1.7(3) . . . . ?
F7 C27 C28 C29 177.36(15) . . . . ?
C26 C27 C28 F8 178.71(15) . . . . ?
F7 C27 C28 F8 -2.2(3) . . . . ?
F8 C28 C29 F9 -1.6(3) . . . . ?
C27 C28 C29 F9 178.87(15) . . . . ?
F8 C28 C29 C30 178.81(15) . . . . ?
C27 C28 C29 C30 -0.7(3) . . . . ?
F9 C29 C30 C31 3.6(2) . . . . ?
C28 C29 C30 C31 -176.86(14) . . . . ?
F9 C29 C30 C25 -176.80(12) . . . . ?
C28 C29 C30 C25 2.8(2) . . . . ?
C24 C25 C30 C31 -2.18(18) . . . . ?
C26 C25 C30 C31 177.21(12) . . . . ?
C24 C25 C30 C29 178.16(12) . . . . ?
C26 C25 C30 C29 -2.45(18) . . . . ?
C29 C30 C31 F10 0.4(2) . . . . ?
C25 C30 C31 F10 -179.21(11) . . . . ?
C29 C30 C31 C32 -179.35(13) . . . . ?
C25 C30 C31 C32 1.01(19) . . . . ?
F10 C31 C32 C19 0.88(19) . . . . ?
C30 C31 C32 C19 -179.34(12) . . . . ?
F10 C31 C32 C23 -178.73(10) . . . . ?
C30 C31 C32 C23 1.05(19) . . . . ?
F1 C19 C32 C31 1.40(19) . . . . ?
C20 C19 C32 C31 -178.08(12) . . . . ?
F1 C19 C32 C23 -178.99(10) . . . . ?
C20 C19 C32 C23 1.53(18) . . . . ?
C24 C23 C32 C31 -1.90(16) . . . . ?
C22 C23 C32 C31 178.05(11) . . . . ?
C24 C23 C32 C19 178.47(11) . . . . ?
C22 C23 C32 C19 -1.58(16) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034



#=======================================================END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_NDFA_100K
_database_code_depnum_ccdc_archive 'CCDC 2293626'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

_audit_creation_date             2022-09-12
_cell_oxdiff_angle_alpha         89.943(3)
_cell_oxdiff_angle_beta          96.351(3)
_cell_oxdiff_angle_gamma         90.079(3)
_cell_oxdiff_length_a            7.4086(3)
_cell_oxdiff_length_b            6.5843(2)
_cell_oxdiff_length_c            18.7821(9)
_cell_oxdiff_measurement_reflns_used 5150
_cell_oxdiff_volume              910.57(6)
_chemical_oxdiff_formula         'C48 H16 F20'
_diffrn_orient_matrix_UB_11      -0.0655869000
_diffrn_orient_matrix_UB_12      0.0774192000
_diffrn_orient_matrix_UB_13      0.0701088000
_diffrn_orient_matrix_UB_21      -0.1914613000
_diffrn_orient_matrix_UB_22      0.0336482000
_diffrn_orient_matrix_UB_23      -0.0392347000
_diffrn_orient_matrix_UB_31      -0.0530772000
_diffrn_orient_matrix_UB_32      -0.2182151000
_diffrn_orient_matrix_UB_33      0.0188991000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'

loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
johannes.krebs@uni-wuerzburg.de
florian.rauch@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_audit_creation_method           
;
FinalCif V86 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'naphthalene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C10 H8'
_chemical_formula_sum            'C24 H8 F10'
_chemical_formula_weight         486.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_oxdiff_exptl_absorpt_empirical_details 
;

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.886
_oxdiff_exptl_absorpt_empirical_full_min 0.537
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.4096(2)
_cell_length_b                   6.5845(2)
_cell_length_c                   18.7792(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.356(3)
_cell_angle_gamma                90
_cell_volume                     910.58(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5232
_cell_measurement_theta_min      4.6890
_cell_measurement_theta_max      74.1170
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.569
_shelx_estimated_absorpt_T_min   0.618
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;

CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_measurement_details      
;

List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     65.00 111.00   0.50    0.06    --   58.41  27.00 103.00   92
  2  ω     83.00 129.00   0.50    0.06    --   76.53  27.00 103.00   92
  3  ω     77.00 124.00   0.50    0.06    --   71.12  27.00 103.00   94
  4  ω     57.00 135.00   0.50    0.06    --   84.31  15.00  60.00  156
  5  ω     40.00 120.00   0.50    0.06    --   76.53  15.00  60.00  160
  6  ω     57.00 135.00   0.50    0.06    --   84.31  15.00 -30.00  156
  7  ω     58.00 109.00   0.50    0.06    --   58.41  15.00 -60.00  102
  8  ω     40.00 120.00   0.50    0.06    --   76.53  15.00-120.00  160
  9  ω     57.00 135.00   0.50    0.06    --   84.31  15.00-180.00  156
 10  ω     58.00 109.00   0.50    0.06    --   58.41  15.00-180.00  102
 11  ω     16.00  66.00   0.50    0.06    --   58.41 -95.00 -90.00  100
 12  ω     34.00  84.00   0.50    0.06    --   76.53 -95.00-150.00  100
 13  ω     42.00  92.00   0.50    0.06    --   84.31 -95.00-120.00  100
 14  ω     42.00  92.00   0.50    0.06    --   84.31 -95.00 -60.00  100
 15  ω     16.00  60.00   0.50    0.06    --   58.41 -95.00   0.00   88
 16  ω     42.00  92.00   0.50    0.06    --   84.31 -95.00  30.00  100
 17  ω     34.00  84.00   0.50    0.06    --   76.53 -95.00  90.00  100
 18  ω     28.00  79.00   0.50    0.06    --   71.12 -95.00 150.00  102
 19  ω     16.00  66.00   0.50    0.06    --   58.41 -95.00  90.00  100
 20  ω   -113.00 -67.00   0.50    0.06    --  -60.26 -27.00 -58.00   92
 21  ω   -129.00 -83.00   0.50    0.06    --  -76.33 -27.00 -58.00   92
 22  ω   -122.00 -76.00   0.50    0.06    --  -69.77 -27.00 -58.00   92
 23  ω    -96.00 -28.00   0.50    0.06    --  -76.33 112.00-120.00  136
;
_diffrn_reflns_number            12566
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.739
_diffrn_reflns_theta_max         74.724
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.7613
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2878
_reflns_number_gt                2464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (G. Sheldrick)'
_computing_molecular_graphics    'SHELXT (G. Sheldrick)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1004P)²+0.5596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2878
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1690
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_twin_special_details            
;

Component 2 rotated by -179.9803° 
around [0.96 0.00 -0.27] (reciprocal) or [1.00 0.00 -0.00] (direct)
;

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7840 3716 5090 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.2160 3760 5090 nmt 0.9998 0.0010 -0.0006 0.0005 -1.0002 0.0001 -0.5648
-0.0006 -0.9989

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 0.4824(4) -0.0716(5) 0.59543(16) 0.0284(7) Uani 1 1 d . . . . .
H1 H 0.445150 -0.183633 0.622148 0.034 Uiso 1 1 calc R U . . .
F1 F -0.1098(3) -0.2734(3) 0.66399(9) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.5463(4) 0.1017(5) 0.63043(16) 0.0299(7) Uani 1 1 d . . . . .
H2 H 0.553316 0.109003 0.681185 0.036 Uiso 1 1 calc R U . . .
F2 F -0.0159(3) 0.0025(3) 0.76667(9) 0.0369(5) Uani 1 1 d . . . . .
C3 C 0.6019(4) 0.2698(5) 0.59087(17) 0.0309(7) Uani 1 1 d . . . . .
H3 H 0.644930 0.389680 0.615301 0.037 Uiso 1 1 calc R U . . .
F3 F 0.1325(3) 0.3609(3) 0.73589(9) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.5941(4) 0.2606(5) 0.51818(17) 0.0281(7) Uani 1 1 d . . . . .
H4 H 0.633208 0.373644 0.492449 0.034 Uiso 1 1 calc R U . . .
F4 F 0.1818(2) 0.4597(3) 0.60075(9) 0.0303(5) Uani 1 1 d . . . . .
C5 C 0.5283(4) 0.0843(5) 0.48033(16) 0.0259(6) Uani 1 1 d . . . . .
F5 F 0.1425(2) 0.3659(3) 0.46818(9) 0.0287(4) Uani 1 1 d . . . . .
C6 C -0.0395(4) -0.0957(5) 0.64518(16) 0.0274(7) Uani 1 1 d . . . . .
C7 C 0.0088(4) 0.0415(5) 0.69770(15) 0.0299(7) Uani 1 1 d . . . . .
C8 C 0.0832(4) 0.2303(5) 0.68112(15) 0.0283(7) Uani 1 1 d . . . . .
C9 C 0.1066(4) 0.2791(5) 0.61293(16) 0.0263(7) Uani 1 1 d . . . . .
C10 C 0.0547(4) 0.1425(5) 0.55545(15) 0.0241(6) Uani 1 1 d . . . . .
C11 C 0.0715(4) 0.1854(5) 0.48398(16) 0.0247(6) Uani 1 1 d . . . . .
C12 C 0.0197(4) 0.0515(5) 0.42757(15) 0.0248(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
C1 C2 1.375(4) . ?
C1 C5 1.419(4) 3_656 ?
C1 H1 0.9500 . ?
F1 C6 1.344(4) . ?
C2 C3 1.419(5) . ?
C2 H2 0.9500 . ?
F2 C7 1.353(3) . ?
C3 C4 1.361(5) . ?
C3 H3 0.9500 . ?
F3 C8 1.359(3) . ?
C4 C5 1.419(4) . ?
C4 H4 0.9500 . ?
F4 C9 1.344(4) . ?
C5 C5 1.422(6) 3_656 ?
F5 C11 1.346(3) . ?
C6 C7 1.356(4) . ?
C6 C12 1.420(4) 3_556 ?
C7 C8 1.409(5) . ?
C8 C9 1.350(4) . ?
C9 C10 1.425(4) . ?
C10 C11 1.390(4) . ?
C10 C12 1.441(4) 3_556 ?
C11 C12 1.399(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 C5 120.4(3) . 3_656 ?
C2 C1 H1 119.8 . . ?
C5 C1 H1 119.8 3_656 . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C1 C5 C4 121.9(3) 3_656 . ?
C1 C5 C5 119.2(3) 3_656 3_656 ?
C4 C5 C5 118.9(3) . 3_656 ?
F1 C6 C7 117.9(3) . . ?
F1 C6 C12 121.0(3) . 3_556 ?
C7 C6 C12 121.1(3) . 3_556 ?
F2 C7 C6 121.2(3) . . ?
F2 C7 C8 118.5(3) . . ?
C6 C7 C8 120.4(3) . . ?
C9 C8 F3 121.0(3) . . ?
C9 C8 C7 120.9(3) . . ?
F3 C8 C7 118.1(3) . . ?
F4 C9 C8 118.1(3) . . ?
F4 C9 C10 120.8(3) . . ?
C8 C9 C10 121.1(3) . . ?
C11 C10 C9 123.9(3) . . ?
C11 C10 C12 118.1(3) . 3_556 ?
C9 C10 C12 118.0(3) . 3_556 ?
F5 C11 C10 118.1(3) . . ?
F5 C11 C12 118.1(3) . . ?
C10 C11 C12 123.8(3) . . ?
C11 C12 C6 123.4(3) . 3_556 ?
C11 C12 C10 118.1(3) . 3_556 ?
C6 C12 C10 118.5(3) 3_556 3_556 ?

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
C5 C1 C2 C3 0.1(4) 3_656 . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C1 179.5(3) . . . 3_656 ?
C3 C4 C5 C5 -0.5(5) . . . 3_656 ?
F1 C6 C7 F2 -1.2(4) . . . . ?
C12 C6 C7 F2 177.6(3) 3_556 . . . ?
F1 C6 C7 C8 -180.0(3) . . . . ?
C12 C6 C7 C8 -1.2(5) 3_556 . . . ?
F2 C7 C8 C9 -178.4(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
F2 C7 C8 F3 2.4(4) . . . . ?
C6 C7 C8 F3 -178.8(3) . . . . ?
F3 C8 C9 F4 0.6(4) . . . . ?
C7 C8 C9 F4 -178.6(3) . . . . ?
F3 C8 C9 C10 -179.9(2) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
F4 C9 C10 C11 -2.0(4) . . . . ?
C8 C9 C10 C11 178.5(3) . . . . ?
F4 C9 C10 C12 178.0(2) . . . 3_556 ?
C8 C9 C10 C12 -1.5(4) . . . 3_556 ?
C9 C10 C11 F5 0.6(4) . . . . ?
C12 C10 C11 F5 -179.4(2) 3_556 . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C12 C10 C11 C12 0.3(5) 3_556 . . . ?
F5 C11 C12 C6 0.5(4) . . . 3_556 ?
C10 C11 C12 C6 -179.2(3) . . . 3_556 ?
F5 C11 C12 C10 179.4(2) . . . 3_556 ?
C10 C11 C12 C10 -0.3(5) . . . 3_556 ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.070


####################################################################### 
# 
# 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_NDFA_299K
_database_code_depnum_ccdc_archive 'CCDC 2293627'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details


loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.3n (K.Radacki, 2005-22)'
_audit_creation_date             2022-11-28
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'naphthalene decafluoroanthracene'
_chemical_formula_moiety         'C14 F10, C10 H8'
_chemical_formula_sum            'C24 H8 F10'
_chemical_formula_weight         486.30
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_cell_length_a                   7.5869(2)
_cell_length_b                   6.63558(18)
_cell_length_c                   19.0089(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.108(3)
_cell_angle_gamma                90
_cell_volume                     949.62(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    3666
_cell_measurement_theta_min      4.6960
_cell_measurement_theta_max      70.9590

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.504
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) 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_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the 
 crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 
 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 1 0.0642
0 1 -1 0.0666
1 2 2 0.0747
0 -1 -1 0.0785
0 -1 -2 0.0800
-2 1 1 0.1690
0 1 2 0.0572
-1 0 0 0.1673
2 0 -1 0.1593
0 0 1 0.0457
0 0 -1 0.1258
0 1 -2 0.0665
0 -1 2 0.0505
-1 0 2 0.1380
1 1 -1 0.1201
1 -1 -5 0.1010

_shelx_estimated_absorpt_T_min   0.637
_shelx_estimated_absorpt_T_max   0.840
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     57.00 133.00   0.50    0.25    --   82.37  15.00   0.00  152
  2  ω     97.00 137.00   0.50    0.25    --   85.25  36.00  11.29   80
  3  ω     57.00 133.00   0.50    0.25    --   82.37  15.00 -60.00  152
  4  ω    100.00 125.00   0.50    0.25    --   85.25  63.00  54.55   50
  5  ω    105.00 131.00   0.50    0.25    --   85.25 111.00 166.00   52
  6  ω    102.00 128.00   0.50    0.25    --   85.25 128.00-150.50   52
  7  ω     93.00 132.00   0.50    0.25    --   85.25 136.00 -66.66   78
  8  ω     47.00  73.00   0.50    0.25    --   85.25 -74.00  92.48   52
  9  ω     36.00 101.00   0.50    0.25    --   85.25-119.00  35.41  130
 10  ω     20.00  87.00   0.50    0.25    --   58.71-126.00 -30.00  134
 11  ω     34.00 100.00   0.50    0.25    --   82.37-112.00-180.00  132
 12  ω     34.00 100.00   0.50    0.25    --   82.37-112.00 -60.00  132
 13  ω     40.00  90.00   0.50    0.25    --   82.37 -95.00-120.00  100
 14  ω     40.00  90.00   0.50    0.25    --   82.37 -95.00-180.00  100
 15  ω     46.00  84.00   0.50    0.25    --   85.25 -84.00 -95.28   76
 16  ω     34.00 100.00   0.50    0.25    --   82.37-112.00 -30.00  132
 17  ω     40.00  90.00   0.50    0.25    --   82.37 -95.00   0.00  100
 18  ω     40.00  90.00   0.50    0.25    --   82.37 -95.00  60.00  100
 19  ω     49.00  98.00   0.50    0.25    --   85.25-102.00  97.78   98
 20  ω     45.00  71.00   0.50    0.25    --   85.25 -75.00 176.18   52
 21  ω   -130.00 -90.00   0.50    0.25    --  -79.50 -38.00-175.91   80
 22  ω   -111.00 -76.00   0.50    0.25    --  -62.00 -47.00-133.19   70
 23  ω   -127.00 -92.00   0.50    0.25    --  -79.50 -53.00-125.89   70
 24  ω   -104.00 -67.00   0.50    0.25    --  -54.00 -44.00 -25.75   74
 25  ω   -103.00 -32.00   0.50    0.25    --  -79.50 130.00 -36.10  142
 26  ω   -124.00 -92.00   0.50    0.25    --  -79.50 -63.00 -21.56   64
 27  ω   -128.00 -93.00   0.50    0.25    --  -79.50 -50.00  20.98   70
 28  ω   -128.00 -94.00   0.50    0.25    --  -79.50-118.00 -89.06   68
 29  ω   -128.00 -94.00   0.50    0.25    --  -79.50-118.00 113.07   68
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.1468560000
_diffrn_orient_matrix_UB_12      0.0692065000
_diffrn_orient_matrix_UB_13      0.0583527000
_diffrn_orient_matrix_UB_21      0.0640211000
_diffrn_orient_matrix_UB_22      0.1557135000
_diffrn_orient_matrix_UB_23      -0.0513493000
_diffrn_orient_matrix_UB_31      -0.1273781000
_diffrn_orient_matrix_UB_32      0.1574917000
_diffrn_orient_matrix_UB_33      0.0251765000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            10241
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.689
_diffrn_reflns_theta_max         74.460
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1936
_reflns_number_gt                1517
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0518P)²+0.1565P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_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_
_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 0.4813(2) -0.0720(3) 0.59338(12) 0.0775(6) Uani 1 1 d . . . . .
H1 H 0.444899 -0.181080 0.618701 0.093 Uiso 1 1 calc R U . . .
F1 F -0.11187(17) -0.26986(18) 0.65998(6) 0.0912(4) Uani 1 1 d . . . . .
C2 C 0.5428(3) 0.0962(4) 0.62860(12) 0.0843(6) Uani 1 1 d . . . . .
H2 H 0.547490 0.102440 0.677669 0.101 Uiso 1 1 calc R U . . .
F2 F -0.0171(2) 0.0015(2) 0.76233(6) 0.1092(5) Uani 1 1 d . . . . .
C3 C 0.5994(3) 0.2611(3) 0.59098(13) 0.0847(6) Uani 1 1 d . . . . .
H3 H 0.641989 0.376133 0.615351 0.102 Uiso 1 1 calc R U . . .
F3 F 0.13109(18) 0.3544(2) 0.73327(7) 0.1049(5) Uani 1 1 d . . . . .
C4 C 0.5927(2) 0.2541(3) 0.51958(12) 0.0760(6) Uani 1 1 d . . . . .
H4 H 0.631578 0.364307 0.495460 0.091 Uiso 1 1 calc R U . . .
F4 F 0.18040(15) 0.45185(17) 0.60079(6) 0.0841(4) Uani 1 1 d . . . . .
C5 C 0.5285(2) 0.0845(2) 0.48172(10) 0.0628(4) Uani 1 1 d . . . . .
F5 F 0.14273(14) 0.36030(15) 0.47022(6) 0.0746(3) Uani 1 1 d . . . . .
C6 C -0.0410(2) -0.0944(3) 0.64278(10) 0.0680(5) Uani 1 1 d . . . . .
C7 C 0.0075(3) 0.0406(3) 0.69422(10) 0.0777(6) Uani 1 1 d . . . . .
C8 C 0.0821(3) 0.2258(3) 0.67912(10) 0.0762(5) Uani 1 1 d . . . . .
C9 C 0.1055(2) 0.2738(3) 0.61250(10) 0.0653(4) Uani 1 1 d . . . . .
C10 C 0.05392(19) 0.1398(2) 0.55528(9) 0.0552(4) Uani 1 1 d . . . . .
C11 C 0.0715(2) 0.1821(2) 0.48485(9) 0.0568(4) Uani 1 1 d . . . . .
C12 C 0.0210(2) 0.0519(2) 0.42921(9) 0.0565(4) Uani 1 1 d . . . . .


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 C2 1.354(3) . ?
C1 C5 1.423(3) 3_656 ?
C1 H1 0.9300 . ?
F1 C6 1.340(2) . ?
C2 C3 1.403(3) . ?
C2 H2 0.9300 . ?
F2 C7 1.356(2) . ?
C3 C4 1.353(3) . ?
C3 H3 0.9300 . ?
F3 C8 1.353(2) . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
F4 C9 1.342(2) . ?
C5 C5 1.414(3) 3_656 ?
F5 C11 1.3433(18) . ?
C6 C7 1.344(3) . ?
C6 C12 1.424(2) 3_556 ?
C7 C8 1.398(3) . ?
C8 C9 1.339(3) . ?
C9 C10 1.422(2) . ?
C10 C11 1.390(2) . ?
C10 C12 1.439(2) 3_556 ?
C11 C12 1.383(2) . ?

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 C5 121.06(19) . 3_656 ?
C2 C1 H1 119.5 . . ?
C5 C1 H1 119.5 3_656 . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.91(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C5 119.7(2) . 3_656 ?
C4 C5 C1 122.51(18) . 3_656 ?
C5 C5 C1 117.8(2) 3_656 3_656 ?
F1 C6 C7 118.94(17) . . ?
F1 C6 C12 120.03(18) . 3_556 ?
C7 C6 C12 121.03(17) . 3_556 ?
C6 C7 F2 120.63(19) . . ?
C6 C7 C8 121.22(17) . . ?
F2 C7 C8 118.14(19) . . ?
C9 C8 F3 120.9(2) . . ?
C9 C8 C7 120.52(18) . . ?
F3 C8 C7 118.59(18) . . ?
C8 C9 F4 118.35(17) . . ?
C8 C9 C10 121.26(17) . . ?
F4 C9 C10 120.40(16) . . ?
C11 C10 C9 124.07(16) . . ?
C11 C10 C12 117.60(15) . 3_556 ?
C9 C10 C12 118.33(15) . 3_556 ?
F5 C11 C12 118.17(15) . . ?
F5 C11 C10 117.78(15) . . ?
C12 C11 C10 124.04(15) . . ?
C11 C12 C6 124.00(16) . 3_556 ?
C11 C12 C10 118.36(15) . 3_556 ?
C6 C12 C10 117.63(16) 3_556 3_556 ?

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
C5 C1 C2 C3 -0.5(3) 3_656 . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C5 -0.8(3) . . . 3_656 ?
C3 C4 C5 C1 179.72(17) . . . 3_656 ?
F1 C6 C7 F2 -1.0(3) . . . . ?
C12 C6 C7 F2 177.93(16) 3_556 . . . ?
F1 C6 C7 C8 179.98(17) . . . . ?
C12 C6 C7 C8 -1.1(3) 3_556 . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
F2 C7 C8 C9 -178.47(18) . . . . ?
C6 C7 C8 F3 -178.94(18) . . . . ?
F2 C7 C8 F3 2.0(3) . . . . ?
F3 C8 C9 F4 0.6(3) . . . . ?
C7 C8 C9 F4 -178.88(17) . . . . ?
F3 C8 C9 C10 -179.80(16) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 178.74(16) . . . . ?
F4 C9 C10 C11 -1.7(2) . . . . ?
C8 C9 C10 C12 -1.4(2) . . . 3_556 ?
F4 C9 C10 C12 178.18(14) . . . 3_556 ?
C9 C10 C11 F5 0.4(2) . . . . ?
C12 C10 C11 F5 -179.46(12) 3_556 . . . ?
C9 C10 C11 C12 -179.87(15) . . . . ?
C12 C10 C11 C12 0.2(2) 3_556 . . . ?
F5 C11 C12 C6 0.5(2) . . . 3_556 ?
C10 C11 C12 C6 -179.21(15) . . . 3_556 ?
F5 C11 C12 C10 179.46(12) . . . 3_556 ?
C10 C11 C12 C10 -0.2(2) . . . 3_556 ?




#=======================================================END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_PerDFA_100K
_database_code_depnum_ccdc_archive 'CCDC 2293637'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details

loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'perylene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C20 H12'
_chemical_formula_sum            'C34 H12 F10'
_chemical_formula_weight         610.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.9692(5)
_cell_length_b                   8.9198(6)
_cell_length_c                   10.9187(8)
_cell_angle_alpha                66.146(7)
_cell_angle_beta                 87.489(6)
_cell_angle_gamma                71.797(6)
_cell_volume                     587.03(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5782
_cell_measurement_theta_min      5.5560
_cell_measurement_theta_max      73.5820


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             306
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    1.370
_shelx_estimated_absorpt_T_min   0.542
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) Empirical 
absorption correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0286
0 0 -1 0.0058
0 0 1 0.0092
1 1 -1 0.0882
0 -1 -1 0.0415
1 0 0 0.1286
-1 0 0 0.3406

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     52.00 105.00   0.50    0.35    --   82.31  15.00-120.00  106
   2  ω     77.00 132.00   0.50    0.35    --   82.31  15.00   0.00  110
   3  ω     83.00 132.00   0.50    0.35    --   82.31  15.00 -60.00   98
   4  ω     75.00 130.00   0.50    0.35    --   82.31  15.00 -90.00  110
   5  ω     46.00 133.00   0.50    0.35    --   82.31  15.00  30.00  174
   6  ω     46.00 133.00   0.50    0.35    --   82.31  15.00  90.00  174
   7  ω    100.00 133.00   0.50    0.35    --   85.25  44.00 142.31   66
   8  ω     81.00 107.00   0.50    0.35    --   82.31  15.00  60.00   52
   9  ω     44.00  69.00   0.50    0.35    --   85.25 -72.00  68.09   50
  10  ω     34.00  97.00   0.50    0.35    --   82.31-112.00  90.00  126
  11  ω     36.00 107.00   0.50    0.35    --   82.31-138.00 118.00  142
  12  ω     28.00  93.00   0.50    0.35    --   58.61-138.00 118.00  130
  13  ω     25.00 103.00   0.50    0.35    --   71.30-133.00 -64.00  156
  14  ω     71.00  97.00   0.50    0.35    --   82.31-112.00-150.00   52
  15  ω     34.00  97.00   0.50    0.35    --   82.31-112.00 -90.00  126
  16  ω     35.00  65.00   0.50    0.35    --   82.31-112.00-150.00   60
  17  ω     35.00 103.00   0.50    0.35    --   82.31-133.00 -64.00  136
  18  ω     69.00  97.00   0.50    0.35    --   82.31-112.00   0.00   56
  19  ω     65.00  97.00   0.50    0.35    --   82.31-112.00  30.00   64
  20  ω     41.00  67.00   0.50    0.35    --   82.31-112.00  60.00   52
  21  ω     70.00  95.00   0.50    0.35    --   82.31-112.00 120.00   50
  22  ω     52.00  92.00   0.50    0.35    --   85.25-108.00 169.67   80
  23  ω     40.00  65.00   0.50    0.35    --   82.31 -95.00   0.00   50
  24  ω     41.00  66.00   0.50    0.35    --   82.31 -95.00  60.00   50
  25  ω     41.00  90.00   0.50    0.35    --   82.31 -95.00  30.00   98
  26  ω     43.00  68.00   0.50    0.35    --   82.31 -95.00 -30.00   50
  27  ω     40.00  90.00   0.50    0.35    --   82.31 -95.00 -60.00  100
  28  ω     40.00  90.00   0.50    0.35    --   82.31 -95.00-120.00  100
  29  ω     40.00  65.00   0.50    0.35    --   82.31 -95.00-180.00   50
  30  ω     40.00  74.00   0.50    0.35    --   82.31 -95.00-150.00   68
  31  ω     44.00  71.00   0.50    0.35    --   82.31 -95.00 -90.00   54
  32  ω     48.00  74.00   0.50    0.35    --   82.31 -95.00 120.00   52
  33  ω   -116.00 -79.00   0.50    0.35    --  -66.00 -44.00  -5.56   74
  34  ω   -127.00 -92.00   0.50    0.35    --  -79.50 -54.00  76.57   70
  35  ω   -125.00 -91.00   0.50    0.35    --  -79.50 -61.00 161.05   68
  36  ω   -128.00 -93.00   0.50    0.35    --  -79.50 -49.00  88.98   70
  37  ω   -128.00 -93.00   0.50    0.35    --  -79.50 -51.00  21.62   70
  38  ω   -107.00 -72.00   0.50    0.35    --  -58.00 -49.00 118.72   70
  39  ω   -126.00 -91.00   0.50    0.35    --  -79.50 -58.00 -64.92   70
  40  ω   -102.00 -67.00   0.50    0.35    --  -54.00 -51.00 -89.83   70
  41  ω   -127.00 -91.00   0.50    0.35    --  -79.50 -56.00-159.76   72
  42  ω   -115.00 -80.00   0.50    0.35    --  -66.00 -48.00 -43.98   70
  43  ω   -116.00 -79.00   0.50    0.35    --  -66.00 -45.00  84.41   74
  44  ω   -128.00 -93.00   0.50    0.35    --  -79.50-120.00 -11.33   70
  45  ω   -102.00 -23.00   0.50    0.35    --  -69.72 133.00   3.00  158
  46  ω    -92.00 -19.00   0.50    0.35    --  -60.19 133.00   3.00  146
  47  ω   -103.00 -29.00   0.50    0.35    --  -76.37 133.00   3.00  148
  48  ω    -97.00 -28.00   0.50    0.35    --  -76.37 112.00 150.00  138
  49  ω    -95.00 -22.00   0.50    0.35    --  -60.19 138.00 179.00  146
  50  ω   -104.00 -23.00   0.50    0.35    --  -69.72 138.00 179.00  162
  51  ω   -107.00 -30.00   0.50    0.35    --  -76.37 138.00 179.00  154
  52  ω    -97.00 -28.00   0.50    0.35    --  -76.37 112.00 -60.00  138

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            11572
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.448
_diffrn_reflns_theta_max         73.702
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2334
_reflns_number_gt                1789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1605P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2334
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2085
_refine_ls_wR_factor_gt          0.1901
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7394(2) 0.23948(17) 0.01361(15) 0.0387(4) Uani 1 1 d . . . . .
F2 F 0.7601(2) 0.38705(16) 0.18277(15) 0.0366(4) Uani 1 1 d . . . . .
F3 F 0.86035(19) 0.35043(15) 0.41738(14) 0.0357(4) Uani 1 1 d . . . . .
F4 F 0.95715(19) 0.31648(16) 0.65136(15) 0.0367(4) Uani 1 1 d . . . . .
F5 F 1.11766(19) 0.10694(17) 0.90477(15) 0.0369(4) Uani 1 1 d . . . . .
C1 C 0.8182(3) 0.1419(3) 0.1417(3) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.8302(3) 0.2134(3) 0.2285(3) 0.0307(5) Uani 1 1 d . . . . .
C3 C 0.9143(3) 0.1098(3) 0.3647(2) 0.0298(5) Uani 1 1 d . . . . .
C4 C 0.9291(3) 0.1774(3) 0.4578(2) 0.0289(5) Uani 1 1 d . . . . .
C5 C 1.0108(3) 0.0758(3) 0.5913(2) 0.0292(5) Uani 1 1 d . . . . .
C6 C 1.0252(3) 0.1445(3) 0.6867(3) 0.0312(5) Uani 1 1 d . . . . .
C7 C 1.1060(3) 0.0405(3) 0.8150(3) 0.0327(6) Uani 1 1 d . . . . .
C8 C 0.4609(3) 0.1494(3) 0.5314(2) 0.0301(5) Uani 1 1 d . . . . .
C9 C 0.4250(3) 0.2900(3) 0.5663(3) 0.0334(5) Uani 1 1 d . . . . .
H9 H 0.363413 0.403815 0.499587 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4766(3) 0.2685(3) 0.6955(3) 0.0346(6) Uani 1 1 d . . . . .
H10 H 0.450424 0.367196 0.715100 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5654(3) 0.1052(3) 0.7953(3) 0.0351(6) Uani 1 1 d . . . . .
H11 H 0.599299 0.091544 0.883343 0.042 Uiso 1 1 calc R U . . .
C12 C 0.6059(3) -0.0422(3) 0.7659(3) 0.0315(5) Uani 1 1 d . . . . .
C13 C 0.6971(3) -0.2108(3) 0.8681(3) 0.0348(6) Uani 1 1 d . . . . .
H13 H 0.731886 -0.225774 0.956469 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7344(3) -0.3525(3) 0.8375(3) 0.0370(6) Uani 1 1 d . . . . .
H14 H 0.796039 -0.465319 0.905528 0.044 Uiso 1 1 calc R U . . .
C15 C 0.6838(3) -0.3334(3) 0.7092(3) 0.0338(5) Uani 1 1 d . . . . .
H15 H 0.711375 -0.433901 0.691902 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5934(3) -0.1708(3) 0.6048(2) 0.0313(5) Uani 1 1 d . . . . .
C17 C 0.5543(3) -0.0211(3) 0.6340(2) 0.0292(5) 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
F1 C1 1.341(3) . ?
F2 C2 1.345(2) . ?
F3 C4 1.346(2) . ?
F4 C6 1.345(2) . ?
F5 C7 1.351(3) . ?
C1 C2 1.357(3) . ?
C1 C7 1.419(3) 2_756 ?
C2 C3 1.427(3) . ?
C3 C4 1.396(3) . ?
C3 C5 1.443(3) 2_756 ?
C4 C5 1.398(3) . ?
C5 C6 1.426(3) . ?
C6 C7 1.353(4) . ?
C8 C9 1.401(3) . ?
C8 C17 1.435(3) . ?
C8 C16 1.472(3) 2_656 ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.419(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.421(3) . ?
C12 C17 1.422(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.438(3) . ?

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
F1 C1 C2 121.8(2) . . ?
F1 C1 C7 118.3(2) . 2_756 ?
C2 C1 C7 119.9(2) . 2_756 ?
F2 C2 C1 118.1(2) . . ?
F2 C2 C3 120.1(2) . . ?
C1 C2 C3 121.8(2) . . ?
C4 C3 C2 123.9(2) . . ?
C4 C3 C5 118.1(2) . 2_756 ?
C2 C3 C5 118.0(2) . 2_756 ?
F3 C4 C3 118.5(2) . . ?
F3 C4 C5 117.69(19) . . ?
C3 C4 C5 123.8(2) . . ?
C4 C5 C6 123.9(2) . . ?
C4 C5 C3 118.1(2) . 2_756 ?
C6 C5 C3 118.0(2) . 2_756 ?
F4 C6 C7 117.7(2) . . ?
F4 C6 C5 120.6(2) . . ?
C7 C6 C5 121.7(2) . . ?
F5 C7 C6 121.2(2) . . ?
F5 C7 C1 118.3(2) . 2_756 ?
C6 C7 C1 120.5(2) . 2_756 ?
C9 C8 C17 117.8(2) . . ?
C9 C8 C16 122.6(2) . 2_656 ?
C17 C8 C16 119.60(19) . 2_656 ?
C10 C9 C8 122.2(2) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 C17 119.9(2) . . ?
C13 C12 C17 120.0(2) . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 117.7(2) . . ?
C15 C16 C8 122.4(2) . 2_656 ?
C17 C16 C8 119.9(2) . 2_656 ?
C12 C17 C8 119.7(2) . . ?
C12 C17 C16 119.8(2) . . ?
C8 C17 C16 120.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 0.1(3) . . . . ?
C7 C1 C2 F2 178.75(18) 2_756 . . . ?
F1 C1 C2 C3 -179.87(18) . . . . ?
C7 C1 C2 C3 -1.2(3) 2_756 . . . ?
F2 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.75(18) . . . . ?
F2 C2 C3 C5 -179.44(17) . . . 2_756 ?
C1 C2 C3 C5 0.5(3) . . . 2_756 ?
C2 C3 C4 F3 -0.1(3) . . . . ?
C5 C3 C4 F3 179.72(16) 2_756 . . . ?
C2 C3 C4 C5 179.77(18) . . . . ?
C5 C3 C4 C5 -0.5(4) 2_756 . . . ?
F3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C6 -179.69(18) . . . . ?
F3 C4 C5 C3 -179.72(16) . . . 2_756 ?
C3 C4 C5 C3 0.5(4) . . . 2_756 ?
C4 C5 C6 F4 0.4(3) . . . . ?
C3 C5 C6 F4 -179.76(17) 2_756 . . . ?
C4 C5 C6 C7 -179.93(19) . . . . ?
C3 C5 C6 C7 -0.1(3) 2_756 . . . ?
F4 C6 C7 F5 0.1(3) . . . . ?
C5 C6 C7 F5 -179.57(17) . . . . ?
F4 C6 C7 C1 -179.54(18) . . . 2_756 ?
C5 C6 C7 C1 0.8(3) . . . 2_756 ?
C17 C8 C9 C10 0.0(3) . . . . ?
C16 C8 C9 C10 179.90(18) 2_656 . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -179.9(2) . . . . ?
C10 C11 C12 C17 -0.2(3) . . . . ?
C11 C12 C13 C14 179.75(19) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C14 C15 C16 C8 -179.96(19) . . . 2_656 ?
C11 C12 C17 C8 -0.1(3) . . . . ?
C13 C12 C17 C8 179.57(18) . . . . ?
C11 C12 C17 C16 -179.31(18) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C9 C8 C17 C12 0.3(3) . . . . ?
C16 C8 C17 C12 -179.67(17) 2_656 . . . ?
C9 C8 C17 C16 179.43(18) . . . . ?
C16 C8 C17 C16 -0.5(3) 2_656 . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C8 C16 C17 C12 179.67(17) 2_656 . . . ?
C15 C16 C17 C8 -179.69(18) . . . . ?
C8 C16 C17 C8 0.5(3) 2_656 . . . ?

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.133



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_ADFA_299K
_database_code_depnum_ccdc_archive 'CCDC 2293630'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details


loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'anthracene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C14 H10'
_chemical_formula_sum            'C28 H10 F10'
_chemical_formula_weight         536.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2524(3)
_cell_length_b                   7.4269(4)
_cell_length_c                   10.5461(6)
_cell_angle_alpha                83.280(4)
_cell_angle_beta                 73.176(5)
_cell_angle_gamma                77.567(4)
_cell_volume                     530.07(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    4225
_cell_measurement_theta_min      4.3730
_cell_measurement_theta_max      73.2070


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    1.416
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0463
0 0 1 0.0042
0 1 0 0.1142
0 -1 0 0.1024
1 0 0 0.1334
-1 0 0 0.1208
1 2 0 0.0982

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      299.41(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     57.00 133.00   0.50    0.20    --   82.37  15.00 -60.00  152
   2  ω    102.00 127.00   0.50    0.20    --   85.25  53.00 -13.79   50
   3  ω     55.00  90.00   0.50    0.20    --   42.00  52.00 130.51   70
   4  ω     57.00 133.00   0.50    0.20    --   82.37  15.00 120.00  152
   5  ω     57.00 133.00   0.50    0.20    --   82.37  15.00  60.00  152
   6  ω     57.00 133.00   0.50    0.20    --   82.37  15.00  30.00  152
   7  ω     63.00 102.00   0.50    0.20    --   82.37  15.00 -30.00   78
   8  ω     57.00 133.00   0.50    0.20    --   82.37  15.00-180.00  152
   9  ω     57.00 133.00   0.50    0.20    --   82.37  15.00-120.00  152
  10  ω    -96.00 -28.00   0.50    0.20    --  -76.33 112.00 -60.00  136
  11  ω    -96.00 -28.00   0.50    0.20    --  -76.33 112.00 -90.00  136
  12  ω    -78.00 -26.00   0.50    0.20    --  -69.47  96.00  14.00  104
  13  ω    -85.00 -33.00   0.50    0.20    --  -76.33  96.00  14.00  104
  14  ω    -68.00 -17.00   0.50    0.20    --  -60.06  96.00  14.00  102
  15  ω    -96.00 -28.00   0.50    0.20    --  -76.33 112.00 120.00  136
  16  ω   -128.00 -94.00   0.50    0.20    --  -79.50-118.00 170.90   68
  17  ω   -124.00 -92.00   0.50    0.20    --  -79.50 -63.00 169.86   64
  18  ω   -121.00 -86.00   0.50    0.20    --  -74.00 -55.00 111.81   70
  19  ω   -127.00 -91.00   0.50    0.20    --  -79.50 -56.00  82.04   72
  20  ω   -124.00 -92.00   0.50    0.20    --  -79.50 -63.00  12.00   64
  21  ω   -103.00 -68.00   0.50    0.20    --  -54.00 -48.00  31.14   70
  22  ω   -128.00 -93.00   0.50    0.20    --  -79.50 -52.00 -75.24   70
  23  ω   -128.00 -93.00   0.50    0.20    --  -79.50 -52.00 -39.33   70
  24  ω   -129.00 -92.00   0.50    0.20    --  -79.50 -44.00 174.84   74
  25  ω   -128.00 -94.00   0.50    0.20    --  -79.50-118.00 -92.99   68
  26  ω   -127.00 -92.00   0.50    0.20    --  -79.50 -54.00-141.77   70
  27  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00-150.00  100
  28  ω     34.00 100.00   0.50    0.20    --   82.37-112.00 -90.00  132
  29  ω     34.00 100.00   0.50    0.20    --   82.37-112.00 -60.00  132
  30  ω     60.00  97.00   0.50    0.20    --   85.25-100.00-138.52   74
  31  ω     34.00 100.00   0.50    0.20    --   82.37-112.00   0.00  132
  32  ω     39.00  91.00   0.50    0.20    --   82.37 -96.00 -94.00  104
  33  ω     40.00  99.00   0.50    0.20    --   85.25-104.00  61.77  118
  34  ω     34.00 100.00   0.50    0.20    --   82.37-112.00  90.00  132
  35  ω     34.00 100.00   0.50    0.20    --   82.37-112.00 150.00  132
  36  ω     44.00  94.00   0.50    0.20    --   85.25 -97.00 168.60  100
  37  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00  90.00  100
  38  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00 120.00  100
  39  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00   0.00  100
  40  ω     28.00  80.00   0.50    0.20    --   71.12 -96.00 -94.00  104
  41  ω     16.00  66.00   0.50    0.20    --   58.41 -95.00-150.00  100
  42  ω     40.00  65.00   0.50    0.20    --   82.37 -95.00-180.00   50
  43  ω     15.00  67.00   0.50    0.20    --   58.41 -96.00 -94.00  104
  44  ω     47.00  73.00   0.50    0.20    --   82.37 -95.00 -90.00   52
  45  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00 -60.00  100
  46  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00  30.00  100
  47  ω     16.00  66.00   0.50    0.20    --   58.41 -95.00  90.00  100
  48  ω     40.00  90.00   0.50    0.20    --   82.37 -95.00 150.00  100

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            10772
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.387
_diffrn_reflns_theta_max         74.058
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2123
_reflns_number_gt                1462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1451P)²+0.0984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2123
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2569
_refine_ls_wR_factor_gt          0.2352
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3468(3) 0.7636(3) 0.21301(18) 0.1010(7) Uani 1 1 d . . . . .
F2 F 0.6927(3) 0.7671(3) 0.03405(18) 0.1096(7) Uani 1 1 d . . . . .
F3 F 1.0309(3) 0.6097(3) 0.0922(2) 0.1076(7) Uani 1 1 d . . . . .
F4 F 1.0324(2) 0.4254(2) 0.32307(19) 0.0950(6) Uani 1 1 d . . . . .
F5 F 0.8410(2) 0.3211(2) 0.55226(17) 0.0881(6) Uani 1 1 d . . . . .
C1 C 0.5069(4) 0.1661(4) 0.2427(3) 0.0828(8) Uani 1 1 d . . . . .
H1 H 0.390589 0.216758 0.220538 0.099 Uiso 1 1 calc R U . . .
C2 C 0.6799(5) 0.1716(5) 0.1511(3) 0.0930(9) Uani 1 1 d . . . . .
H2 H 0.681611 0.225990 0.066845 0.112 Uiso 1 1 calc R U . . .
C3 C 0.8590(4) 0.0951(4) 0.1825(3) 0.0905(9) Uani 1 1 d . . . . .
H3 H 0.977442 0.099052 0.118524 0.109 Uiso 1 1 calc R U . . .
C4 C 0.8590(4) 0.0170(4) 0.3039(3) 0.0797(8) Uani 1 1 d . . . . .
H4 H 0.978139 -0.031398 0.322918 0.096 Uiso 1 1 calc R U . . .
C5 C 0.6812(4) 0.0065(3) 0.4042(3) 0.0709(7) Uani 1 1 d . . . . .
C6 C 0.6754(4) -0.0761(4) 0.5305(3) 0.0740(7) Uani 1 1 d . . . . .
H6 H 0.793181 -0.127752 0.550367 0.089 Uiso 1 1 calc R U . . .
C7 C 0.5007(4) -0.0843(3) 0.6279(3) 0.0699(7) Uani 1 1 d . . . . .
C8 C 0.5107(4) 0.6808(4) 0.2467(3) 0.0773(7) Uani 1 1 d . . . . .
C9 C 0.6848(5) 0.6867(4) 0.1544(3) 0.0873(8) Uani 1 1 d . . . . .
C10 C 0.8609(4) 0.5989(4) 0.1845(3) 0.0832(8) Uani 1 1 d . . . . .
C11 C 0.8595(4) 0.5102(4) 0.3019(3) 0.0757(7) Uani 1 1 d . . . . .
C12 C 0.6826(4) 0.5008(3) 0.4024(3) 0.0697(7) Uani 1 1 d . . . . .
C13 C 0.6718(4) 0.4107(3) 0.5266(3) 0.0723(7) Uani 1 1 d . . . . .
C14 C 0.4993(4) 0.4071(3) 0.6266(3) 0.0697(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
F1 C8 1.340(3) . ?
F2 C9 1.329(4) . ?
F3 C10 1.342(3) . ?
F4 C11 1.344(3) . ?
F5 C13 1.349(3) . ?
C1 C2 1.349(4) . ?
C1 C7 1.418(4) 2_656 ?
C1 H1 0.9300 . ?
C2 C3 1.416(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.343(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.422(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 C7 1.440(4) 2_656 ?
C6 C7 1.389(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.358(4) . ?
C8 C14 1.407(4) 2_666 ?
C9 C10 1.409(4) . ?
C10 C11 1.332(4) . ?
C11 C12 1.417(4) . ?
C12 C13 1.389(4) . ?
C12 C14 1.449(4) 2_666 ?
C13 C14 1.386(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 C7 121.2(3) . 2_656 ?
C2 C1 H1 119.4 . . ?
C7 C1 H1 119.4 2_656 . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 123.1(3) . . ?
C6 C5 C7 119.0(3) . 2_656 ?
C4 C5 C7 117.9(3) . 2_656 ?
C7 C6 C5 122.6(3) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C1 123.1(3) . 2_656 ?
C6 C7 C5 118.4(3) . 2_656 ?
C1 C7 C5 118.5(3) 2_656 2_656 ?
F1 C8 C9 117.5(3) . . ?
F1 C8 C14 120.6(3) . 2_666 ?
C9 C8 C14 121.9(3) . 2_666 ?
F2 C9 C8 121.4(3) . . ?
F2 C9 C10 119.0(3) . . ?
C8 C9 C10 119.5(3) . . ?
C11 C10 F3 120.7(3) . . ?
C11 C10 C9 121.1(3) . . ?
F3 C10 C9 118.2(3) . . ?
C10 C11 F4 118.1(3) . . ?
C10 C11 C12 122.0(3) . . ?
F4 C11 C12 120.0(3) . . ?
C13 C12 C11 124.6(3) . . ?
C13 C12 C14 117.9(3) . 2_666 ?
C11 C12 C14 117.5(3) . 2_666 ?
F5 C13 C14 117.6(3) . . ?
F5 C13 C12 117.8(2) . . ?
C14 C13 C12 124.6(2) . . ?
C13 C14 C8 124.5(3) . 2_666 ?
C13 C14 C12 117.5(3) . 2_666 ?
C8 C14 C12 118.1(3) 2_666 2_666 ?

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
C7 C1 C2 C3 0.1(5) 2_656 . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C3 C4 C5 C7 -0.6(4) . . . 2_656 ?
C4 C5 C6 C7 179.5(2) . . . . ?
C7 C5 C6 C7 -0.9(5) 2_656 . . . ?
C5 C6 C7 C1 -179.2(2) . . . 2_656 ?
C5 C6 C7 C5 0.9(5) . . . 2_656 ?
F1 C8 C9 F2 -1.7(5) . . . . ?
C14 C8 C9 F2 178.7(2) 2_666 . . . ?
F1 C8 C9 C10 -178.9(3) . . . . ?
C14 C8 C9 C10 1.5(5) 2_666 . . . ?
F2 C9 C10 C11 -177.3(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
F2 C9 C10 F3 3.8(4) . . . . ?
C8 C9 C10 F3 -178.9(3) . . . . ?
F3 C10 C11 F4 -2.8(4) . . . . ?
C9 C10 C11 F4 178.4(2) . . . . ?
F3 C10 C11 C12 178.3(2) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C11 C12 C13 -179.9(3) . . . . ?
F4 C11 C12 C13 1.1(4) . . . . ?
C10 C11 C12 C14 -0.4(4) . . . 2_666 ?
F4 C11 C12 C14 -179.3(2) . . . 2_666 ?
C11 C12 C13 F5 -2.0(4) . . . . ?
C14 C12 C13 F5 178.4(2) 2_666 . . . ?
C11 C12 C13 C14 177.6(2) . . . . ?
C14 C12 C13 C14 -2.0(5) 2_666 . . . ?
F5 C13 C14 C8 1.1(4) . . . 2_666 ?
C12 C13 C14 C8 -178.5(2) . . . 2_666 ?
F5 C13 C14 C12 -178.4(2) . . . 2_666 ?
C12 C13 C14 C12 2.0(5) . . . 2_666 ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.053




#=======================================================END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_TetDFA_Cocrystal_298K
_database_code_depnum_ccdc_archive 'CCDC 2293632'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details


loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de


_audit_creation_method           'CIF-fill 1.2y (K.Radacki, 2005-22)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'tetracene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C18 H12'
_chemical_formula_sum            'C32 H12 F10'
_chemical_formula_weight         586.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.0122(4)
_cell_length_b                   7.2711(4)
_cell_length_c                   12.2638(6)
_cell_angle_alpha                79.844(4)
_cell_angle_beta                 73.405(4)
_cell_angle_gamma                82.693(4)
_cell_volume                     587.89(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4091
_cell_measurement_theta_min      3.7850
_cell_measurement_theta_max      72.7980


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    1.338
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0262
0 -1 -1 0.0204
1 0 1 0.0703
-1 0 -1 0.0512
0 0 -1 0.0111
0 0 1 0.0131

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      298.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     46.00 133.00   0.50    0.37    --   82.31  15.00-180.00  174
   2  ω     46.00 133.00   0.50    0.37    --   82.31  15.00-120.00  174
   3  ω     46.00 133.00   0.50    0.37    --   82.31  15.00 -30.00  174
   4  ω     46.00 133.00   0.50    0.37    --   82.31  15.00  90.00  174
   5  ω     34.00  60.00   0.50    0.37    --   22.00  57.00 151.15   52
   6  ω   -103.00 -32.00   0.50    0.37    --  -79.50 133.00 144.64  142
   7  ω    -97.00 -28.00   0.50    0.37    --  -76.37 112.00 120.00  138
   8  ω    -97.00 -28.00   0.50    0.37    --  -76.37 112.00  60.00  138
   9  ω    -36.00 -10.00   0.50    0.37    --  -10.00 121.00 -33.76   52
  10  ω    -97.00 -28.00   0.50    0.37    --  -76.37 112.00 -60.00  138
  11  ω    -97.00 -28.00   0.50    0.37    --  -76.37 112.00-120.00  138
  12  ω     38.00 103.00   0.50    0.37    --   85.25-132.00 -83.24  130
  13  ω     34.00  97.00   0.50    0.37    --   82.31-112.00 -90.00  126
  14  ω     34.00  97.00   0.50    0.37    --   82.31-112.00-180.00  126
  15  ω     34.00  97.00   0.50    0.37    --   82.31-112.00-150.00  126
  16  ω     34.00  97.00   0.50    0.37    --   82.31-112.00 -30.00  126
  17  ω     34.00  97.00   0.50    0.37    --   82.31-112.00   0.00  126
  18  ω     34.00  97.00   0.50    0.37    --   82.31-112.00  30.00  126
  19  ω     34.00  97.00   0.50    0.37    --   82.31-112.00  60.00  126
  20  ω     40.00  90.00   0.50    0.37    --   82.31 -95.00 120.00  100
  21  ω     34.00  97.00   0.50    0.37    --   82.31-112.00 120.00  126
  22  ω     39.00  94.00   0.50    0.37    --   85.25-105.00  75.57  110
  23  ω     40.00  90.00   0.50    0.37    --   82.31 -95.00 150.00  100
  24  ω     46.00  83.00   0.50    0.37    --   85.25 -80.00 120.04   74
  25  ω     46.00  83.00   0.50    0.37    --   85.25 -80.00  78.10   74
  26  ω     40.00  90.00   0.50    0.37    --   82.31 -95.00  30.00  100
  27  ω     42.00  93.00   0.50    0.37    --   85.25 -98.00 -49.34  102
  28  ω     40.00  90.00   0.50    0.37    --   82.31 -95.00 -90.00  100
  29  ω   -130.00 -91.00   0.50    0.37    --  -79.50 -40.00 151.23   78
  30  ω   -126.00 -92.00   0.50    0.37    --  -79.50 -57.00  84.14   68
  31  ω   -128.00 -93.00   0.50    0.37    --  -79.50 -52.00  60.80   70
  32  ω   -103.00 -68.00   0.50    0.37    --  -54.00 -50.00  -6.45   70
  33  ω   -128.00 -93.00   0.50    0.37    --  -79.50 -51.00 -65.13   70
  34  ω   -127.00 -92.00   0.50    0.37    --  -79.50 -54.00-122.77   70
  35  ω   -120.00 -86.00   0.50    0.37    --  -74.00 -60.00-158.52   68
  36  ω   -103.00 -68.00   0.50    0.37    --  -54.00 -50.00-117.90   70
  37  ω   -128.00 -93.00   0.50    0.37    --  -79.50 -49.00-101.08   70
  38  ω   -115.00 -80.00   0.50    0.37    --  -66.00 -49.00 -40.23   70
  39  ω   -111.00 -76.00   0.50    0.37    --  -62.00 -48.00 -22.79   70
  40  ω   -128.00 -93.00   0.50    0.37    --  -79.50 -49.00  40.03   70
  41  ω   -128.00 -93.00   0.50    0.37    --  -79.50 -49.00 114.89   70
  42  ω   -107.00 -72.00   0.50    0.37    --  -58.00 -47.00  89.26   70
  43  ω   -104.00 -67.00   0.50    0.37    --  -54.00 -44.00 177.58   74
  44  ω    -79.00 -44.00   0.50    0.37    --  -30.00 -49.00  24.93   70
  45  ω    -92.00 -55.00   0.50    0.37    --  -42.00 -45.00 -98.53   74
  46  ω   -126.00 -86.00   0.50    0.37    --  -79.50-135.00-122.25   80
  47  ω   -126.00 -85.00   0.50    0.37    --  -79.50-136.00  30.30   82

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            11965
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_max         74.270
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2345
_reflns_number_gt                1680
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+0.0450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2345
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24806(15) 0.65793(14) 0.78271(8) 0.0746(3) Uani 1 1 d . . . . .
F2 F 0.26792(16) 0.34096(15) 0.92850(8) 0.0822(3) Uani 1 1 d . . . . .
F3 F 0.43771(16) 0.01878(14) 0.85241(8) 0.0805(3) Uani 1 1 d . . . . .
F4 F 0.60536(14) 0.00778(12) 0.62881(8) 0.0683(3) Uani 1 1 d . . . . .
F5 F 0.68622(13) 0.17792(11) 0.42373(7) 0.0614(3) Uani 1 1 d . . . . .
C1 C 0.3339(2) 0.5011(2) 0.74039(13) 0.0538(4) Uani 1 1 d . . . . .
C2 C 0.3430(2) 0.3423(2) 0.81494(13) 0.0593(4) Uani 1 1 d . . . . .
C3 C 0.4340(2) 0.1749(2) 0.77521(13) 0.0578(4) Uani 1 1 d . . . . .
C4 C 0.5164(2) 0.1704(2) 0.66206(13) 0.0509(4) Uani 1 1 d . . . . .
C5 C 0.51105(19) 0.33346(18) 0.57900(12) 0.0437(3) Uani 1 1 d . . . . .
C6 C 0.5930(2) 0.33670(18) 0.46137(12) 0.0454(3) Uani 1 1 d . . . . .
C7 C 0.58520(19) 0.49546(19) 0.38021(12) 0.0443(3) Uani 1 1 d . . . . .
C8 C 0.8018(2) 0.4326(2) 0.83932(13) 0.0618(4) Uani 1 1 d . . . . .
H8 H 0.748827 0.545028 0.866439 0.074 Uiso 1 1 calc R U . . .
C9 C 0.8027(3) 0.2727(3) 0.91487(14) 0.0723(5) Uani 1 1 d . . . . .
H9 H 0.750414 0.276594 0.993255 0.087 Uiso 1 1 calc R U . . .
C10 C 0.8821(3) 0.1006(3) 0.87613(14) 0.0697(5) Uani 1 1 d . . . . .
H10 H 0.880767 -0.007775 0.929389 0.084 Uiso 1 1 calc R U . . .
C11 C 0.9603(2) 0.0903(2) 0.76272(13) 0.0583(4) Uani 1 1 d . . . . .
H11 H 1.012586 -0.024704 0.738985 0.070 Uiso 1 1 calc R U . . .
C12 C 0.9631(2) 0.25526(19) 0.67889(12) 0.0461(3) Uani 1 1 d . . . . .
C13 C 1.0404(2) 0.24958(19) 0.56222(12) 0.0457(3) Uani 1 1 d . . . . .
H13 H 1.093265 0.135587 0.537221 0.055 Uiso 1 1 calc R U . . .
C14 C 1.04107(19) 0.41220(17) 0.48028(11) 0.0415(3) Uani 1 1 d . . . . .
C15 C 1.1190(2) 0.40820(19) 0.36158(11) 0.0465(3) Uani 1 1 d . . . . .
H15 H 1.172098 0.294710 0.335942 0.056 Uiso 1 1 calc R U . . .
C16 C 1.1189(2) 0.5692(2) 0.28157(12) 0.0467(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3371(18) . ?
F2 C2 1.3395(17) . ?
F3 C3 1.3463(16) . ?
F4 C4 1.3382(17) . ?
F5 C6 1.3404(15) . ?
C1 C2 1.347(2) . ?
C1 C7 1.422(2) 2_666 ?
C2 C3 1.400(2) . ?
C3 C4 1.347(2) . ?
C4 C5 1.4245(19) . ?
C5 C6 1.3892(19) . ?
C5 C7 1.4375(19) 2_666 ?
C6 C7 1.3914(19) . ?
C8 C9 1.353(2) . ?
C8 C16 1.429(2) 2_766 ?
C8 H8 0.9300 . ?
C9 C10 1.408(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.353(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.4338(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.3839(19) . ?
C12 C16 1.438(2) 2_766 ?
C13 C14 1.4098(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.4054(19) . ?
C14 C14 1.438(2) 2_766 ?
C15 C16 1.3884(19) . ?
C15 H15 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
F1 C1 C2 118.25(14) . . ?
F1 C1 C7 120.22(14) . 2_666 ?
C2 C1 C7 121.53(14) . 2_666 ?
F2 C2 C1 121.04(15) . . ?
F2 C2 C3 118.43(14) . . ?
C1 C2 C3 120.52(14) . . ?
F3 C3 C4 120.76(15) . . ?
F3 C3 C2 118.65(14) . . ?
C4 C3 C2 120.59(14) . . ?
F4 C4 C3 118.22(13) . . ?
F4 C4 C5 120.25(13) . . ?
C3 C4 C5 121.53(14) . . ?
C6 C5 C4 123.94(14) . . ?
C6 C5 C7 118.26(12) . 2_666 ?
C4 C5 C7 117.80(13) . 2_666 ?
F5 C6 C5 118.15(12) . . ?
F5 C6 C7 117.98(13) . . ?
C5 C6 C7 123.87(13) . . ?
C6 C7 C1 124.12(14) . 2_666 ?
C6 C7 C5 117.87(13) . 2_666 ?
C1 C7 C5 118.02(13) 2_666 2_666 ?
C9 C8 C16 120.84(16) . 2_766 ?
C9 C8 H8 119.6 . . ?
C16 C8 H8 119.6 2_766 . ?
C8 C9 C10 120.74(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.14(15) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.48(16) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 122.03(14) . . ?
C13 C12 C16 119.60(12) . 2_766 ?
C11 C12 C16 118.37(13) . 2_766 ?
C12 C13 C14 121.68(13) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 122.20(13) . . ?
C15 C14 C14 119.02(15) . 2_766 ?
C13 C14 C14 118.78(15) . 2_766 ?
C16 C15 C14 121.76(13) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C8 122.40(14) . 2_766 ?
C15 C16 C12 119.17(13) . 2_766 ?
C8 C16 C12 118.42(13) 2_766 2_766 ?

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 0.1(2) . . . . ?
C7 C1 C2 F2 179.36(12) 2_666 . . . ?
F1 C1 C2 C3 -179.01(13) . . . . ?
C7 C1 C2 C3 0.3(2) 2_666 . . . ?
F2 C2 C3 F3 1.7(2) . . . . ?
C1 C2 C3 F3 -179.17(13) . . . . ?
F2 C2 C3 C4 -178.19(13) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
F3 C3 C4 F4 -1.3(2) . . . . ?
C2 C3 C4 F4 178.57(12) . . . . ?
F3 C3 C4 C5 178.97(12) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
F4 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C5 C6 -179.81(13) . . . . ?
F4 C4 C5 C7 -179.54(11) . . . 2_666 ?
C3 C4 C5 C7 0.2(2) . . . 2_666 ?
C4 C5 C6 F5 -1.3(2) . . . . ?
C7 C5 C6 F5 178.68(10) 2_666 . . . ?
C4 C5 C6 C7 179.06(12) . . . . ?
C7 C5 C6 C7 -0.9(2) 2_666 . . . ?
F5 C6 C7 C1 1.4(2) . . . 2_666 ?
C5 C6 C7 C1 -178.99(12) . . . 2_666 ?
F5 C6 C7 C5 -178.69(10) . . . 2_666 ?
C5 C6 C7 C5 0.9(2) . . . 2_666 ?
C16 C8 C9 C10 0.0(3) 2_766 . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 -179.48(14) . . . . ?
C10 C11 C12 C16 0.0(2) . . . 2_766 ?
C11 C12 C13 C14 179.45(12) . . . . ?
C16 C12 C13 C14 0.0(2) 2_766 . . . ?
C12 C13 C14 C15 -179.96(12) . . . . ?
C12 C13 C14 C14 0.0(2) . . . 2_766 ?
C13 C14 C15 C16 179.98(12) . . . . ?
C14 C14 C15 C16 0.1(2) 2_766 . . . ?
C14 C15 C16 C8 179.79(12) . . . 2_766 ?
C14 C15 C16 C12 0.0(2) . . . 2_766 ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036



#=======================================================END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_PyrDFA_100K
_database_code_depnum_ccdc_archive 'CCDC 2293635'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2021-08-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de
_chemical_name_common            ?
_chemical_name_systematic        'pyrene decafluoroanthracene'
_chemical_formula_moiety         'C14 F10, C16 H10'
_chemical_formula_sum            'C30 H10 F10'
_chemical_formula_weight         560.38
_chemical_oxdiff_usercomment     'FR330, pyrene perfluoroanthracene'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1553(2)
_cell_length_b                   8.5840(2)
_cell_length_c                   17.2031(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.246(2)
_cell_angle_gamma                90
_cell_volume                     1056.38(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7261
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7810
_cell_measurement_theta_min      5.1400
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical
absorption correction using spherical harmonics, implemented in 
SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11099
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.467
_diffrn_reflns_theta_min         5.143
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     57.00 133.00   0.50    0.05    --   82.37  15.00 150.00  152
  2  ω     97.00 137.00   0.50    0.05    --   85.25  36.00 168.30   80
  3  ω     57.00 133.00   0.50    0.05    --   82.37  15.00  30.00  152
  4  ω     98.00 135.00   0.50    0.05    --   85.25  41.00  87.81   74
  5  ω    104.00 129.00   0.50    0.05    --   85.25  51.00 -38.38   50
  6  ω    101.00 127.00   0.50    0.05    --   85.25  52.00-117.01   52
  7  ω    103.00 129.00   0.50    0.05    --   85.25 138.00 -77.24   52
  8  ω    101.00 132.00   0.50    0.05    --   85.25 130.00  36.56   62
  9  ω    105.00 130.00   0.50    0.05    --   85.25 110.00  86.86   50
 10  ω     41.00  97.00   0.50    0.05    --   85.25-101.00 110.46  112
 11  ω     38.00 100.00   0.50    0.05    --   85.25-111.00 101.98  124
 12  ω     40.00  90.00   0.50    0.05    --   82.37 -95.00 150.00  100
 13  ω     40.00  90.00   0.50    0.05    --   82.37 -95.00  60.00  100
 14  ω     16.00  66.00   0.50    0.05    --   58.41 -95.00 120.00  100
 15  ω     38.00 105.00   0.50    0.05    --   85.25-133.00  -4.27  134
 16  ω     28.00  79.00   0.50    0.05    --   71.12 -95.00 -60.00  102
 17  ω     34.00 100.00   0.50    0.05    --   82.37-112.00 -60.00  132
 18  ω     40.00  90.00   0.50    0.05    --   82.37 -95.00   0.00  100
 19  ω     40.00  90.00   0.50    0.05    --   82.37 -95.00  30.00  100
 20  ω     52.00  81.00   0.50    0.05    --   85.25 -95.00 161.74   58
 21  ω   -120.00 -83.00   0.50    0.05    --  -70.00 -45.00 120.96   74
 22  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00 123.74   68
 23  ω   -126.00 -92.00   0.50    0.05    --  -79.50 -57.00  90.51   68
 24  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -58.00   6.85   70
 25  ω    -95.00 -60.00   0.50    0.05    --  -46.00 -48.00 -37.72   70
 26  ω   -101.00 -31.00   0.50    0.05    --  -79.50 118.00  26.67  140
 27  ω   -124.00 -92.00   0.50    0.05    --  -79.50 -63.00 -83.95   64
 28  ω   -127.00 -90.00   0.50    0.05    --  -79.50-127.00-164.47   74
 29  ω   -126.00 -86.00   0.50    0.05    --  -79.50-134.00  39.88   80
 30  ω   -126.00 -86.00   0.50    0.05    --  -79.50-135.00  87.96   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1164725000
_diffrn_orient_matrix_UB_12      -0.1491919000
_diffrn_orient_matrix_UB_13      -0.0106836000
_diffrn_orient_matrix_UB_21      -0.0128645000
_diffrn_orient_matrix_UB_22      0.0210948000
_diffrn_orient_matrix_UB_23      -0.0888800000
_diffrn_orient_matrix_UB_31      0.1806483000
_diffrn_orient_matrix_UB_32      0.0975653000
_diffrn_orient_matrix_UB_33      0.0029110000
_diffrn_oxdiff_digest_frames     
;
019d3a30add8718daa586efc7b5bc07e36000977a11
;
_diffrn_oxdiff_digest_hkl        
;
01c0b9231b29f440cc6a693aff61a252823885
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1902
_reflns_number_total             2140
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.059
_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)+(0.0766P)²+0.2379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
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 0.09075(12) -0.14294(10) 0.29940(5) 0.0285(2) Uani 1 1 d . . . . .
F2 F 0.20427(12) 0.11706(10) 0.22887(5) 0.0303(2) Uani 1 1 d . . . . .
F3 F 0.22441(12) 0.39112(10) 0.30644(5) 0.0305(2) Uani 1 1 d . . . . .
F4 F 0.13411(12) 0.40966(9) 0.45601(5) 0.0293(2) Uani 1 1 d . . . . .
F5 F 0.02296(12) 0.27544(9) 0.57812(5) 0.0279(2) Uani 1 1 d . . . . .
C1 C 0.6212(2) 0.12933(19) 0.34214(9) 0.0302(3) Uani 1 1 d . . . . .
H1 H 0.640786 0.102571 0.289357 0.036 Uiso 1 1 calc R . . . .
C2 C 0.6531(2) 0.28113(18) 0.36712(10) 0.0312(4) Uani 1 1 d . . . . .
H2 H 0.693968 0.357317 0.331221 0.037 Uiso 1 1 calc R . . . .
C3 C 0.62577(19) 0.32251(17) 0.44409(9) 0.0298(3) Uani 1 1 d . . . . .
H3 H 0.648743 0.426700 0.460281 0.036 Uiso 1 1 calc R . . . .
C4 C 0.56495(18) 0.21295(16) 0.49806(9) 0.0261(3) Uani 1 1 d . . . . .
C5 C 0.5354(2) 0.25065(18) 0.57828(9) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.558505 0.353887 0.595903 0.035 Uiso 1 1 calc R . . . .
C6 C 0.4756(2) 0.14311(18) 0.62905(9) 0.0292(3) Uani 1 1 d . . . . .
H6 H 0.456735 0.172631 0.681514 0.035 Uiso 1 1 calc R . . . .
C7 C 0.56035(18) 0.01537(17) 0.39414(9) 0.0260(3) Uani 1 1 d . . . . .
C8 C 0.53120(18) 0.05668(16) 0.47310(8) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.09530(18) -0.00988(16) 0.34018(9) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.15298(19) 0.12119(17) 0.30384(8) 0.0251(3) Uani 1 1 d . . . . .
C11 C 0.16512(19) 0.26377(16) 0.34448(9) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.11996(19) 0.27142(16) 0.42025(9) 0.0237(3) Uani 1 1 d . . . . .
C13 C 0.05906(18) 0.13759(15) 0.46148(8) 0.0222(3) Uani 1 1 d . . . . .
C14 C 0.01213(18) 0.13963(15) 0.53978(9) 0.0229(3) Uani 1 1 d . . . . .
C15 C -0.04606(17) 0.00804(16) 0.57997(8) 0.0228(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.3404(16) . ?
F2 C10 1.3490(16) . ?
F3 C11 1.3473(16) . ?
F4 C12 1.3395(15) . ?
F5 C14 1.3408(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(2) . ?
C1 C7 1.401(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C4 C5 1.438(2) . ?
C4 C8 1.427(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.347(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.439(2) 3_656 ?
C7 C8 1.424(2) . ?
C8 C8 1.422(3) 3_656 ?
C9 C10 1.356(2) . ?
C9 C15 1.426(2) 3_556 ?
C10 C11 1.411(2) . ?
C11 C12 1.351(2) . ?
C12 C13 1.4233(19) . ?
C13 C14 1.396(2) . ?
C13 C15 1.4411(19) 3_556 ?
C14 C15 1.393(2) . ?

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 H1 119.7 . . ?
C2 C1 C7 120.57(14) . . ?
C7 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.60(14) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.90(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 122.73(13) . . ?
C3 C4 C8 119.05(13) . . ?
C8 C4 C5 118.22(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.58(14) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.71(14) . 3_656 ?
C7 C6 H6 119.1 3_656 . ?
C1 C7 C6 122.63(14) . 3_656 ?
C1 C7 C8 119.29(14) . . ?
C8 C7 C6 118.08(13) . 3_656 ?
C7 C8 C4 119.59(13) . . ?
C8 C8 C4 120.05(16) 3_656 . ?
C8 C8 C7 120.36(16) 3_656 . ?
F1 C9 C10 118.03(13) . . ?
F1 C9 C15 120.67(12) . 3_556 ?
C10 C9 C15 121.28(13) . 3_556 ?
F2 C10 C9 120.73(13) . . ?
F2 C10 C11 118.77(12) . . ?
C9 C10 C11 120.48(13) . . ?
F3 C11 C10 118.66(13) . . ?
F3 C11 C12 120.90(13) . . ?
C12 C11 C10 120.43(13) . . ?
F4 C12 C11 117.95(12) . . ?
F4 C12 C13 120.47(13) . . ?
C11 C12 C13 121.57(13) . . ?
C12 C13 C15 118.08(13) . 3_556 ?
C14 C13 C12 123.61(13) . . ?
C14 C13 C15 118.31(13) . 3_556 ?
F5 C14 C13 118.24(12) . . ?
F5 C14 C15 118.41(13) . . ?
C15 C14 C13 123.35(13) . . ?
C9 C15 C13 118.15(13) 3_556 3_556 ?
C14 C15 C9 123.51(13) . 3_556 ?
C14 C15 C13 118.34(13) . 3_556 ?

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 C9 C10 F2 -0.1(2) . . . . ?
F1 C9 C10 C11 -178.37(11) . . . . ?
F2 C10 C11 F3 1.16(19) . . . . ?
F2 C10 C11 C12 -178.14(12) . . . . ?
F3 C11 C12 F4 0.68(19) . . . . ?
F3 C11 C12 C13 -179.31(12) . . . . ?
F4 C12 C13 C14 -0.4(2) . . . . ?
F4 C12 C13 C15 179.87(11) . . . 3_556 ?
F5 C14 C15 C9 0.2(2) . . . 3_556 ?
F5 C14 C15 C13 179.51(11) . . . 3_556 ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C7 C8 C4 -0.2(2) . . . . ?
C1 C7 C8 C8 179.75(14) . . . 3_656 ?
C2 C1 C7 C6 179.63(13) . . . 3_656 ?
C2 C1 C7 C8 0.1(2) . . . . ?
C2 C3 C4 C5 179.84(12) . . . . ?
C2 C3 C4 C8 0.1(2) . . . . ?
C3 C4 C5 C6 179.60(13) . . . . ?
C3 C4 C8 C7 0.1(2) . . . . ?
C3 C4 C8 C8 -179.83(14) . . . 3_656 ?
C4 C5 C6 C7 0.5(2) . . . 3_656 ?
C5 C4 C8 C7 -179.60(12) . . . . ?
C5 C4 C8 C8 0.4(2) . . . 3_656 ?
C6 C7 C8 C4 -179.81(11) 3_656 . . . ?
C6 C7 C8 C8 0.2(2) 3_656 . . 3_656 ?
C7 C1 C2 C3 0.2(2) . . . . ?
C8 C4 C5 C6 -0.7(2) . . . . ?
C9 C10 C11 F3 179.50(12) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 F4 179.96(12) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 179.57(13) . . . . ?
C11 C12 C13 C15 -0.1(2) . . . 3_556 ?
C12 C13 C14 F5 0.8(2) . . . . ?
C12 C13 C14 C15 -179.51(12) . . . . ?
C13 C14 C15 C9 -179.57(12) . . . 3_556 ?
C13 C14 C15 C13 -0.2(2) . . . 3_556 ?
C15 C9 C10 F2 178.10(12) 3_556 . . . ?
C15 C9 C10 C11 -0.2(2) 3_556 . . . ?
C15 C13 C14 F5 -179.51(11) 3_556 . . . ?
C15 C13 C14 C15 0.2(2) 3_556 . . . ?

_olex2_date_sample_data_collection 2021-07-27
_olex2_date_sample_submission    2021-07-22
_olex2_exptl_crystal_mounting_method 
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id FR330
_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.736
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_ADFA_200K
_database_code_depnum_ccdc_archive 'CCDC 2293629'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details

loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'anthracene decafluoroanthracene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 F10, C14 H10'
_chemical_formula_sum            'C28 H10 F10'
_chemical_formula_weight         536.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.14326(18)
_cell_length_b                   7.39508(19)
_cell_length_c                   10.4097(3)
_cell_angle_alpha                84.893(2)
_cell_angle_beta                 73.918(2)
_cell_angle_gamma                78.314(2)
_cell_volume                     517.10(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4231
_cell_measurement_theta_min      6.0990
_cell_measurement_theta_max      74.3340


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    1.451
_shelx_estimated_absorpt_T_min   0.623
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -1 0.0319
-2 0 1 0.0302
-1 -2 -1 0.1585
1 2 1 0.1627
-1 0 -2 0.0338
1 0 2 0.0220
0 1 -1 0.1463
-1 0 -1 0.0277
1 0 1 0.0235
0 0 1 0.0148

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     74.00 133.00   0.50    0.05    --   82.37  15.00 150.00  118
   2  ω     99.00 124.00   0.50    0.05    --   85.25  51.00 123.31   50
   3  ω     98.00 132.00   0.50    0.05    --   82.37  15.00  90.00   68
   4  ω    100.00 129.00   0.50    0.05    --   82.37  15.00  60.00   58
   5  ω     62.00  96.00   0.50    0.05    --   82.37  15.00  30.00   68
   6  ω    105.00 132.00   0.50    0.05    --   82.37  15.00  30.00   54
   7  ω     62.00 119.00   0.50    0.05    --   82.37  15.00 -60.00  114
   8  ω     52.00  78.00   0.50    0.05    --   38.00  50.00-127.23   52
   9  ω     40.00  65.00   0.50    0.05    --   82.37 -95.00-120.00   50
  10  ω     48.00  74.00   0.50    0.05    --   85.25-129.00   8.83   52
  11  ω     67.00  99.00   0.50    0.05    --   85.25-135.00  30.67   64
  12  ω     50.00 100.00   0.50    0.05    --   82.37-112.00 120.00  100
  13  ω     44.00  69.00   0.50    0.05    --   82.37-128.00 166.00   50
  14  ω     50.00  76.00   0.50    0.05    --   58.71-128.00 166.00   52
  15  ω     54.00  95.00   0.50    0.05    --   71.32-128.00 166.00   82
  16  ω     24.00  50.00   0.50    0.05    --   71.32-128.00 166.00   52
  17  ω     42.00  86.00   0.50    0.05    --   82.37-112.00  30.00   88
  18  ω     70.00 100.00   0.50    0.05    --   82.37-112.00  60.00   60
  19  ω     75.00 100.00   0.50    0.05    --   82.37-112.00   0.00   50
  20  ω     46.00  96.00   0.50    0.05    --   82.37-112.00 -60.00  100
  21  ω     75.00 100.00   0.50    0.05    --   82.37-112.00-120.00   50
  22  ω     59.00 100.00   0.50    0.05    --   82.37-112.00-150.00   82
  23  ω     34.00  96.00   0.50    0.05    --   82.37-112.00-180.00  124
  24  ω     36.00  61.00   0.50    0.05    --   82.37-112.00-120.00   50
  25  ω     49.00 100.00   0.50    0.05    --   82.37-112.00 -90.00  102
  26  ω     48.00  91.00   0.50    0.05    --   85.25 -97.00-141.68   86
  27  ω     64.00  97.00   0.50    0.05    --   82.37-112.00  90.00   66
  28  ω     35.00  61.00   0.50    0.05    --   82.37-112.00  90.00   52
  29  ω     38.00  64.00   0.50    0.05    --   82.37-112.00  60.00   52
  30  ω     35.00  78.00   0.50    0.05    --   71.32 -95.00  30.00   86
  31  ω     29.00  64.00   0.50    0.05    --   71.32 -95.00-180.00   70
  32  ω     43.00  90.00   0.50    0.05    --   82.37 -95.00 -60.00   94
  33  ω   -117.00 -92.00   0.50    0.05    --  -70.00 -36.00 -13.49   50
  34  ω   -128.00-101.00   0.50    0.05    --  -79.50 -52.00-118.73   54
  35  ω   -119.00 -92.00   0.50    0.05    --  -79.50 -43.00-173.13   54
  36  ω   -102.00 -77.00   0.50    0.05    --  -62.00 -46.00-121.96   50
  37  ω   -123.00 -87.00   0.50    0.05    --  -74.00 -41.00  22.25   72
  38  ω    -93.00 -67.00   0.50    0.05    --  -46.00 -42.00 132.34   52
  39  ω   -127.00-101.00   0.50    0.05    --  -79.50 -50.00 167.56   52
  40  ω   -129.00 -97.00   0.50    0.05    --  -79.50 -40.00 128.54   64
  41  ω   -121.00 -92.00   0.50    0.05    --  -79.50 -57.00  87.09   58
  42  ω   -120.00 -92.00   0.50    0.05    --  -79.50 -39.00  42.08   56
  43  ω   -128.00-103.00   0.50    0.05    --  -79.50 -39.00 -95.91   50
  44  ω    -76.00 -51.00   0.50    0.05    --  -60.26 128.00-119.00   50
  45  ω    -59.00 -33.00   0.50    0.05    --  -76.33 128.00-119.00   52
  46  ω    -98.00 -60.00   0.50    0.05    --  -69.77 128.00-119.00   76
  47  ω   -127.00 -95.00   0.50    0.05    --  -79.50-132.00-143.52   64

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            6934
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.423
_diffrn_reflns_theta_max         74.408
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2078
_reflns_number_gt                1771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.0224P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.34437(10) 0.76208(10) 0.21229(7) 0.0477(2) Uani 1 1 d . . . . .
F2 F 0.69321(11) 0.76473(10) 0.03199(7) 0.0512(2) Uani 1 1 d . . . . .
F3 F 1.03748(10) 0.60776(10) 0.09081(7) 0.0482(2) Uani 1 1 d . . . . .
F4 F 1.03798(9) 0.42138(9) 0.32219(7) 0.0443(2) Uani 1 1 d . . . . .
F5 F 0.84459(9) 0.31966(8) 0.55123(6) 0.0407(2) Uani 1 1 d . . . . .
C1 C 0.50421(17) 0.16258(15) 0.24123(11) 0.0382(3) Uani 1 1 d . . . . .
H1 H 0.383633 0.213134 0.218696 0.046 Uiso 1 1 calc R U . . .
C2 C 0.68024(18) 0.16707(16) 0.14869(11) 0.0429(3) Uani 1 1 d . . . . .
H2 H 0.681551 0.220843 0.062166 0.051 Uiso 1 1 calc R U . . .
C3 C 0.86146(18) 0.09229(16) 0.18029(11) 0.0418(3) Uani 1 1 d . . . . .
H3 H 0.983182 0.096770 0.114639 0.050 Uiso 1 1 calc R U . . .
C4 C 0.86388(16) 0.01412(14) 0.30322(11) 0.0364(3) Uani 1 1 d . . . . .
H4 H 0.986993 -0.035283 0.322597 0.044 Uiso 1 1 calc R U . . .
C5 C 0.68208(15) 0.00569(13) 0.40382(10) 0.0308(2) Uani 1 1 d . . . . .
C6 C 0.67980(15) -0.07486(13) 0.53065(11) 0.0323(2) Uani 1 1 d . . . . .
H6 H 0.801780 -0.125418 0.551278 0.039 Uiso 1 1 calc R U . . .
C7 C 0.50109(15) -0.08256(13) 0.62805(10) 0.0311(2) Uani 1 1 d . . . . .
C8 C 0.51010(17) 0.67997(14) 0.24548(11) 0.0358(3) Uani 1 1 d . . . . .
C9 C 0.68623(18) 0.68268(15) 0.15343(11) 0.0382(3) Uani 1 1 d . . . . .
C10 C 0.86451(16) 0.59723(15) 0.18315(11) 0.0375(3) Uani 1 1 d . . . . .
C11 C 0.86419(16) 0.50581(14) 0.30122(11) 0.0342(3) Uani 1 1 d . . . . .
C12 C 0.68356(15) 0.49924(13) 0.40197(11) 0.0309(2) Uani 1 1 d . . . . .
C13 C 0.67475(15) 0.41019(14) 0.52647(11) 0.0317(2) Uani 1 1 d . . . . .
C14 C 0.49844(15) 0.40790(13) 0.62643(11) 0.0309(2) 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
F1 C8 1.3370(13) . ?
F2 C9 1.3452(13) . ?
F3 C10 1.3506(12) . ?
F4 C11 1.3380(13) . ?
F5 C13 1.3417(12) . ?
C1 C2 1.3602(16) . ?
C1 C7 1.4285(15) 2_656 ?
C1 H1 0.9500 . ?
C2 C3 1.4154(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3597(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4334(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3965(15) . ?
C5 C7 1.4321(15) 2_656 ?
C6 C7 1.4011(15) . ?
C6 H6 0.9500 . ?
C8 C9 1.3566(16) . ?
C8 C14 1.4215(15) 2_666 ?
C9 C10 1.4051(16) . ?
C10 C11 1.3487(16) . ?
C11 C12 1.4260(15) . ?
C12 C13 1.3918(16) . ?
C12 C14 1.4368(15) 2_666 ?
C13 C14 1.3959(15) . ?

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 C7 120.64(11) . 2_656 ?
C2 C1 H1 119.7 . . ?
C7 C1 H1 119.7 2_656 . ?
C1 C2 C3 120.53(11) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.96(10) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.50(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C7 119.74(10) . 2_656 ?
C6 C5 C4 121.81(11) . . ?
C7 C5 C4 118.45(10) 2_656 . ?
C5 C6 C7 121.27(10) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C1 122.08(10) . 2_656 ?
C6 C7 C5 118.99(10) . 2_656 ?
C1 C7 C5 118.92(10) 2_656 2_656 ?
F1 C8 C9 118.12(10) . . ?
F1 C8 C14 120.83(10) . 2_666 ?
C9 C8 C14 121.05(11) . 2_666 ?
F2 C9 C8 120.76(11) . . ?
F2 C9 C10 118.94(10) . . ?
C8 C9 C10 120.29(10) . . ?
C11 C10 F3 120.28(11) . . ?
C11 C10 C9 121.00(10) . . ?
F3 C10 C9 118.72(10) . . ?
F4 C11 C10 118.42(10) . . ?
F4 C11 C12 120.49(10) . . ?
C10 C11 C12 121.09(11) . . ?
C13 C12 C11 123.54(10) . . ?
C13 C12 C14 118.49(10) . 2_666 ?
C11 C12 C14 117.97(10) . 2_666 ?
F5 C13 C12 118.26(10) . . ?
F5 C13 C14 118.18(10) . . ?
C12 C13 C14 123.56(10) . . ?
C13 C14 C8 123.54(10) . 2_666 ?
C13 C14 C12 117.94(10) . 2_666 ?
C8 C14 C12 118.52(10) 2_666 2_666 ?

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
C7 C1 C2 C3 0.07(18) 2_656 . . . ?
C1 C2 C3 C4 0.16(18) . . . . ?
C2 C3 C4 C5 0.04(17) . . . . ?
C3 C4 C5 C6 179.54(9) . . . . ?
C3 C4 C5 C7 -0.46(16) . . . 2_656 ?
C7 C5 C6 C7 0.12(18) 2_656 . . . ?
C4 C5 C6 C7 -179.88(8) . . . . ?
C5 C6 C7 C1 -179.30(8) . . . 2_656 ?
C5 C6 C7 C5 -0.12(18) . . . 2_656 ?
F1 C8 C9 F2 -0.44(16) . . . . ?
C14 C8 C9 F2 179.45(8) 2_666 . . . ?
F1 C8 C9 C10 -179.57(9) . . . . ?
C14 C8 C9 C10 0.31(17) 2_666 . . . ?
F2 C9 C10 C11 -176.85(9) . . . . ?
C8 C9 C10 C11 2.30(17) . . . . ?
F2 C9 C10 F3 2.98(15) . . . . ?
C8 C9 C10 F3 -177.87(9) . . . . ?
F3 C10 C11 F4 -2.22(15) . . . . ?
C9 C10 C11 F4 177.60(9) . . . . ?
F3 C10 C11 C12 177.56(8) . . . . ?
C9 C10 C11 C12 -2.62(17) . . . . ?
F4 C11 C12 C13 1.10(17) . . . . ?
C10 C11 C12 C13 -178.68(9) . . . . ?
F4 C11 C12 C14 -179.84(8) . . . 2_666 ?
C10 C11 C12 C14 0.38(16) . . . 2_666 ?
C11 C12 C13 F5 -2.64(16) . . . . ?
C14 C12 C13 F5 178.31(8) 2_666 . . . ?
C11 C12 C13 C14 178.23(8) . . . . ?
C14 C12 C13 C14 -0.83(18) 2_666 . . . ?
F5 C13 C14 C8 2.16(16) . . . 2_666 ?
C12 C13 C14 C8 -178.71(8) . . . 2_666 ?
F5 C13 C14 C12 -178.32(8) . . . 2_666 ?
C12 C13 C14 C12 0.82(18) . . . 2_666 ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_TriDFA_100K
_database_code_depnum_ccdc_archive 'CCDC 2293638'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de
_chemical_name_common            ?
_chemical_name_systematic        'triphenylene decafluoroanthracene'
_chemical_formula_moiety         'C14 F10, C18 H12'
_chemical_formula_sum            'C32 H12 F10'
_chemical_formula_weight         586.42
_chemical_oxdiff_usercomment     'FR332, triphenylene perfluoroanthracene'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.71719(9)
_cell_length_b                   37.6558(5)
_cell_length_c                   9.27231(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.9071(15)
_cell_angle_gamma                90
_cell_volume                     2294.88(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0690
_cell_measurement_theta_min      4.6750
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.612
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical
absorption correction using spherical harmonics, implemented in 
SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24608
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         2.347
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_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     98.00 123.08   0.38    0.04    --   85.25  57.00  89.28   66
  2  ω    107.00 133.22   0.38    0.04    --   85.25  50.00 111.02   69
  3  ω    103.00 129.22   0.38    0.04    --   85.25  49.00 159.42   69
  4  ω     76.00 132.24   0.38    0.04    --   85.25  21.00  65.21  148
  5  ω     98.00 123.08   0.38    0.04    --   85.25  45.00  54.54   66
  6  ω    109.00 135.22   0.38    0.04    --   85.25  15.00  25.15   69
  7  ω     79.00 105.22   0.38    0.04    --   85.25  15.00  25.15   69
  8  ω     98.00 123.08   0.38    0.04    --   85.25  57.00 -80.15   66
  9  ω    103.00 133.02   0.38    0.04    --   85.25 119.00  19.78   79
 10  ω    107.00 132.08   0.38    0.04    --   85.25 116.00-172.12   66
 11  ω     49.00  75.22   0.38    0.04    --   85.25 -78.00-124.26   69
 12  ω     46.00  71.08   0.38    0.04    --   85.25 -78.00 125.00   66
 13  ω     51.00  77.22   0.38    0.04    --   85.25 -85.00  10.75   69
 14  ω     34.00  99.36   0.38    0.04    --   82.37-112.00  90.00  172
 15  ω     39.00  81.94   0.38    0.04    --   85.25-106.00 100.09  113
 16  ω     68.00  93.08   0.38    0.04    --   85.25-103.00 130.27   66
 17  ω     61.00  87.22   0.38    0.04    --   85.25-104.00  62.72   69
 18  ω     42.00  68.22   0.38    0.04    --   85.25 -99.00 156.77   69
 19  ω     55.00  86.92   0.38    0.04    --   85.25-114.00 -35.98   84
 20  ω     54.00  80.22   0.38    0.04    --   85.25-129.00 -60.27   69
 21  ω     49.00  74.08   0.38    0.04    --   85.25 -97.00 -71.12   66
 22  ω     16.00  65.02   0.38    0.04    --   58.71 -95.00-180.00  129
 23  ω     40.00  65.08   0.38    0.04    --   82.37 -95.00-180.00   66
 24  ω     55.00  81.22   0.38    0.04    --   85.25 -86.00-167.86   69
 25  ω     40.00 105.36   0.38    0.04    --   85.25-134.00-130.26  172
 26  ω     45.00  87.94   0.38    0.04    --   85.25 -90.00  32.81  113
 27  ω     40.00  65.08   0.38    0.04    --   82.37 -95.00  30.00   66
 28  ω   -107.00 -73.18   0.38    0.04    --  -58.00 -48.00 -18.46   89
 29  ω   -124.00 -95.12   0.38    0.04    --  -79.50 -64.00  65.48   76
 30  ω   -124.00 -95.88   0.38    0.04    --  -79.50 -65.00  77.90   74
 31  ω   -126.00 -92.94   0.38    0.04    --  -79.50 -57.00  -7.39   87
 32  ω   -126.00 -92.94   0.38    0.04    --  -79.50 -57.00-136.37   87
 33  ω   -126.00 -92.18   0.38    0.04    --  -79.50 -59.00-153.97   89
 34  ω   -128.00 -94.18   0.38    0.04    --  -79.50 -49.00-110.18   89
 35  ω   -102.00 -68.18   0.38    0.04    --  -54.00 -52.00   1.17   89
 36  ω    -89.00 -36.94   0.38    0.04    --  -79.50  98.00  36.84  137
 37  ω   -100.00 -31.98   0.38    0.04    --  -79.50 119.00 104.01  179
 38  ω   -128.00 -97.22   0.38    0.04    --  -79.50-115.00  23.04   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0649800000
_diffrn_orient_matrix_UB_12      -0.0201922000
_diffrn_orient_matrix_UB_13      0.1466254000
_diffrn_orient_matrix_UB_21      0.0918975000
_diffrn_orient_matrix_UB_22      -0.0296657000
_diffrn_orient_matrix_UB_23      -0.0803136000
_diffrn_orient_matrix_UB_31      0.2056495000
_diffrn_orient_matrix_UB_32      0.0196503000
_diffrn_orient_matrix_UB_33      0.0295111000
_diffrn_oxdiff_digest_frames     
;
01e308bedc13d6fe50978f680a5ef8a1f803371e8bb
;
_diffrn_oxdiff_digest_hkl        
;
01fe9e57ca5f168c0838226d4c2af84a6a53f5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4211
_reflns_number_total             4698
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.052
_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)+(0.0581P)²+0.5438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
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 0.54182(10) 0.38005(2) 0.32229(7) 0.02481(17) Uani 1 1 d . . . . .
F2 F 0.57252(10) 0.45090(2) 0.34203(8) 0.02700(17) Uani 1 1 d . . . . .
F3 F 0.66764(11) 0.48356(2) 0.60549(8) 0.02702(17) Uani 1 1 d . . . . .
F4 F 0.72140(10) 0.44662(2) 0.85746(7) 0.02371(16) Uani 1 1 d . . . . .
F5 F 0.72764(10) 0.38693(2) 0.98515(7) 0.02284(16) Uani 1 1 d . . . . .
F6 F 0.73234(11) 0.32725(2) 1.11471(7) 0.02796(17) Uani 1 1 d . . . . .
F7 F 0.70107(12) 0.25659(2) 1.09512(9) 0.03459(19) Uani 1 1 d . . . . .
F8 F 0.65008(13) 0.22324(2) 0.83232(9) 0.0374(2) Uani 1 1 d . . . . .
F9 F 0.61231(12) 0.26044(2) 0.58065(8) 0.03207(19) Uani 1 1 d . . . . .
F10 F 0.57407(11) 0.32030(2) 0.45244(7) 0.02800(17) Uani 1 1 d . . . . .
C1 C 0.11793(15) 0.38290(3) 0.58710(12) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.06581(16) 0.36753(3) 0.44529(12) 0.0218(2) Uani 1 1 d . . . . .
H2 H 0.055853 0.342429 0.436598 0.026 Uiso 1 1 calc R . . . .
C3 C 0.02913(17) 0.38789(3) 0.31962(12) 0.0243(2) Uani 1 1 d . . . . .
H3 H -0.006922 0.376878 0.225670 0.029 Uiso 1 1 calc R . . . .
C4 C 0.04497(17) 0.42480(3) 0.33033(13) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.020302 0.439005 0.243785 0.029 Uiso 1 1 calc R . . . .
C5 C 0.09646(16) 0.44049(3) 0.46684(13) 0.0216(2) Uani 1 1 d . . . . .
H5 H 0.107759 0.465614 0.473052 0.026 Uiso 1 1 calc R . . . .
C6 C 0.13301(15) 0.42035(3) 0.59795(12) 0.0179(2) Uani 1 1 d . . . . .
C7 C 0.18271(15) 0.43738(3) 0.74318(12) 0.0175(2) Uani 1 1 d . . . . .
C8 C 0.19611(17) 0.47470(3) 0.75761(13) 0.0223(2) Uani 1 1 d . . . . .
H8 H 0.174234 0.488994 0.671343 0.027 Uiso 1 1 calc R . . . .
C9 C 0.24011(18) 0.49085(3) 0.89367(13) 0.0247(2) Uani 1 1 d . . . . .
H9 H 0.246904 0.516009 0.900716 0.030 Uiso 1 1 calc R . . . .
C10 C 0.27471(18) 0.47014(3) 1.02128(13) 0.0247(2) Uani 1 1 d . . . . .
H10 H 0.304583 0.481150 1.115456 0.030 Uiso 1 1 calc R . . . .
C11 C 0.26539(17) 0.43371(3) 1.01016(12) 0.0216(2) Uani 1 1 d . . . . .
H11 H 0.291781 0.419821 1.097561 0.026 Uiso 1 1 calc R . . . .
C12 C 0.21769(15) 0.41650(3) 0.87246(12) 0.0174(2) Uani 1 1 d . . . . .
C13 C 0.20239(15) 0.37771(3) 0.86115(12) 0.0168(2) Uani 1 1 d . . . . .
C14 C 0.23497(16) 0.35617(3) 0.98831(12) 0.0199(2) Uani 1 1 d . . . . .
H14 H 0.269411 0.367046 1.082629 0.024 Uiso 1 1 calc R . . . .
C15 C 0.21804(16) 0.31969(3) 0.97904(13) 0.0220(2) Uani 1 1 d . . . . .
H15 H 0.238869 0.305756 1.066267 0.026 Uiso 1 1 calc R . . . .
C16 C 0.17021(17) 0.30330(3) 0.84108(13) 0.0219(2) Uani 1 1 d . . . . .
H16 H 0.158792 0.278184 0.834098 0.026 Uiso 1 1 calc R . . . .
C17 C 0.13967(16) 0.32373(3) 0.71521(13) 0.0200(2) Uani 1 1 d . . . . .
H17 H 0.108394 0.312352 0.621827 0.024 Uiso 1 1 calc R . . . .
C18 C 0.15362(15) 0.36116(3) 0.72127(12) 0.0175(2) Uani 1 1 d . . . . .
C19 C 0.58694(16) 0.39500(3) 0.45615(12) 0.0194(2) Uani 1 1 d . . . . .
C20 C 0.60172(16) 0.43088(3) 0.46457(12) 0.0205(2) Uani 1 1 d . . . . .
C21 C 0.64907(16) 0.44801(3) 0.60274(13) 0.0205(2) Uani 1 1 d . . . . .
C22 C 0.67745(16) 0.42906(3) 0.72942(12) 0.0181(2) Uani 1 1 d . . . . .
C23 C 0.66274(15) 0.39128(3) 0.72683(12) 0.0168(2) Uani 1 1 d . . . . .
C24 C 0.69023(15) 0.37049(3) 0.85409(12) 0.0173(2) Uani 1 1 d . . . . .
C25 C 0.67967(16) 0.33350(3) 0.85168(12) 0.0186(2) Uani 1 1 d . . . . .
C26 C 0.70219(17) 0.31228(3) 0.98120(13) 0.0220(2) Uani 1 1 d . . . . .
C27 C 0.68890(18) 0.27642(3) 0.97259(14) 0.0253(3) Uani 1 1 d . . . . .
C28 C 0.65833(18) 0.25911(3) 0.83501(15) 0.0270(3) Uani 1 1 d . . . . .
C29 C 0.63679(17) 0.27814(3) 0.70881(14) 0.0239(2) Uani 1 1 d . . . . .
C30 C 0.64221(16) 0.31597(3) 0.71090(12) 0.0189(2) Uani 1 1 d . . . . .
C31 C 0.61161(16) 0.33675(3) 0.58378(12) 0.0196(2) Uani 1 1 d . . . . .
C32 C 0.61912(15) 0.37377(3) 0.58587(12) 0.0174(2) 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
F1 C19 1.3393(12) . ?
F2 C20 1.3439(12) . ?
F3 C21 1.3440(13) . ?
F4 C22 1.3377(12) . ?
F5 C24 1.3406(12) . ?
F6 C26 1.3372(13) . ?
F7 C27 1.3480(13) . ?
F8 C28 1.3519(14) . ?
F9 C29 1.3428(14) . ?
F10 C31 1.3430(12) . ?
C1 C2 1.4129(15) . ?
C1 C6 1.4161(15) . ?
C1 C18 1.4671(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3740(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3960(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3747(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.4106(15) . ?
C6 C7 1.4665(15) . ?
C7 C8 1.4128(15) . ?
C7 C12 1.4121(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3766(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3961(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3759(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.4086(15) . ?
C12 C13 1.4665(15) . ?
C13 C14 1.4106(15) . ?
C13 C18 1.4152(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3795(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3968(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3775(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.4128(15) . ?
C19 C20 1.3560(16) . ?
C19 C32 1.4229(15) . ?
C20 C21 1.4109(16) . ?
C21 C22 1.3538(16) . ?
C22 C23 1.4260(15) . ?
C23 C24 1.3963(15) . ?
C23 C32 1.4391(15) . ?
C24 C25 1.3947(16) . ?
C25 C26 1.4242(15) . ?
C25 C30 1.4377(15) . ?
C26 C27 1.3545(17) . ?
C27 C28 1.4095(18) . ?
C28 C29 1.3542(18) . ?
C29 C30 1.4250(16) . ?
C30 C31 1.3941(16) . ?
C31 C32 1.3950(16) . ?

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 C6 118.32(10) . . ?
C2 C1 C18 121.76(10) . . ?
C6 C1 C18 119.92(10) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.83(11) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.83(11) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.62(11) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.91(11) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 120.00(10) . . ?
C5 C6 C1 118.48(10) . . ?
C5 C6 C7 121.51(10) . . ?
C8 C7 C6 121.32(10) . . ?
C12 C7 C6 120.18(10) . . ?
C12 C7 C8 118.51(10) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.58(11) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.78(11) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.77(11) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.66(11) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C13 119.79(10) . . ?
C11 C12 C7 118.70(10) . . ?
C11 C12 C13 121.50(10) . . ?
C14 C13 C12 121.10(10) . . ?
C14 C13 C18 118.65(10) . . ?
C18 C13 C12 120.25(10) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.59(10) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.84(10) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.67(10) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.77(10) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C1 119.86(10) . . ?
C17 C18 C1 121.67(10) . . ?
C17 C18 C13 118.47(10) . . ?
F1 C19 C20 118.15(10) . . ?
F1 C19 C32 120.88(10) . . ?
C20 C19 C32 120.97(10) . . ?
F2 C20 C19 120.95(10) . . ?
F2 C20 C21 118.52(10) . . ?
C19 C20 C21 120.53(10) . . ?
F3 C21 C20 118.37(10) . . ?
F3 C21 C22 120.83(10) . . ?
C22 C21 C20 120.79(10) . . ?
F4 C22 C21 118.38(10) . . ?
F4 C22 C23 120.66(10) . . ?
C21 C22 C23 120.96(10) . . ?
C22 C23 C32 118.22(10) . . ?
C24 C23 C22 123.28(10) . . ?
C24 C23 C32 118.50(10) . . ?
F5 C24 C23 118.32(10) . . ?
F5 C24 C25 118.37(9) . . ?
C25 C24 C23 123.31(10) . . ?
C24 C25 C26 123.40(10) . . ?
C24 C25 C30 118.14(10) . . ?
C26 C25 C30 118.45(10) . . ?
F6 C26 C25 120.90(10) . . ?
F6 C26 C27 118.06(10) . . ?
C27 C26 C25 121.02(11) . . ?
F7 C27 C26 120.73(11) . . ?
F7 C27 C28 118.60(11) . . ?
C26 C27 C28 120.66(11) . . ?
F8 C28 C27 118.46(11) . . ?
F8 C28 C29 121.08(12) . . ?
C29 C28 C27 120.46(11) . . ?
F9 C29 C28 118.28(11) . . ?
F9 C29 C30 120.42(11) . . ?
C28 C29 C30 121.30(11) . . ?
C29 C30 C25 118.05(10) . . ?
C31 C30 C25 118.54(10) . . ?
C31 C30 C29 123.41(10) . . ?
F10 C31 C30 118.37(10) . . ?
F10 C31 C32 118.23(10) . . ?
C30 C31 C32 123.40(10) . . ?
C19 C32 C23 118.51(10) . . ?
C31 C32 C19 123.42(10) . . ?
C31 C32 C23 118.07(10) . . ?

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 C19 C20 F2 -0.20(15) . . . . ?
F1 C19 C20 C21 -179.94(9) . . . . ?
F1 C19 C32 C23 -178.64(9) . . . . ?
F1 C19 C32 C31 1.68(16) . . . . ?
F2 C20 C21 F3 -1.58(15) . . . . ?
F2 C20 C21 C22 179.20(9) . . . . ?
F3 C21 C22 F4 1.01(15) . . . . ?
F3 C21 C22 C23 -178.45(9) . . . . ?
F4 C22 C23 C24 0.68(16) . . . . ?
F4 C22 C23 C32 -178.76(9) . . . . ?
F5 C24 C25 C26 1.41(16) . . . . ?
F5 C24 C25 C30 -179.18(8) . . . . ?
F6 C26 C27 F7 1.52(17) . . . . ?
F6 C26 C27 C28 -179.65(10) . . . . ?
F7 C27 C28 F8 -2.43(17) . . . . ?
F7 C27 C28 C29 177.24(10) . . . . ?
F8 C28 C29 F9 -1.73(17) . . . . ?
F8 C28 C29 C30 179.02(10) . . . . ?
F9 C29 C30 C25 -176.73(9) . . . . ?
F9 C29 C30 C31 3.77(17) . . . . ?
F10 C31 C32 C19 0.70(16) . . . . ?
F10 C31 C32 C23 -178.99(9) . . . . ?
C1 C2 C3 C4 0.60(17) . . . . ?
C1 C6 C7 C8 -179.13(9) . . . . ?
C1 C6 C7 C12 0.65(15) . . . . ?
C2 C1 C6 C5 -0.35(15) . . . . ?
C2 C1 C6 C7 178.77(9) . . . . ?
C2 C1 C18 C13 -179.01(9) . . . . ?
C2 C1 C18 C17 0.66(15) . . . . ?
C2 C3 C4 C5 -0.25(17) . . . . ?
C3 C4 C5 C6 -0.41(16) . . . . ?
C4 C5 C6 C1 0.71(16) . . . . ?
C4 C5 C6 C7 -178.40(10) . . . . ?
C5 C6 C7 C8 -0.04(16) . . . . ?
C5 C6 C7 C12 179.74(9) . . . . ?
C6 C1 C2 C3 -0.29(16) . . . . ?
C6 C1 C18 C13 0.20(15) . . . . ?
C6 C1 C18 C17 179.88(9) . . . . ?
C6 C7 C8 C9 179.14(10) . . . . ?
C6 C7 C12 C11 179.91(9) . . . . ?
C6 C7 C12 C13 -0.54(15) . . . . ?
C7 C8 C9 C10 0.68(18) . . . . ?
C7 C12 C13 C14 -179.52(9) . . . . ?
C7 C12 C13 C18 0.28(15) . . . . ?
C8 C7 C12 C11 -0.31(15) . . . . ?
C8 C7 C12 C13 179.24(9) . . . . ?
C8 C9 C10 C11 0.26(18) . . . . ?
C9 C10 C11 C12 -1.23(17) . . . . ?
C10 C11 C12 C7 1.25(16) . . . . ?
C10 C11 C12 C13 -178.29(10) . . . . ?
C11 C12 C13 C14 0.02(16) . . . . ?
C11 C12 C13 C18 179.81(9) . . . . ?
C12 C7 C8 C9 -0.64(16) . . . . ?
C12 C13 C14 C15 179.03(9) . . . . ?
C12 C13 C18 C1 -0.10(14) . . . . ?
C12 C13 C18 C17 -179.78(9) . . . . ?
C13 C14 C15 C16 0.86(16) . . . . ?
C14 C13 C18 C1 179.70(9) . . . . ?
C14 C13 C18 C17 0.02(14) . . . . ?
C14 C15 C16 C17 -0.20(16) . . . . ?
C15 C16 C17 C18 -0.56(16) . . . . ?
C16 C17 C18 C1 -179.04(9) . . . . ?
C16 C17 C18 C13 0.64(15) . . . . ?
C18 C1 C2 C3 178.93(10) . . . . ?
C18 C1 C6 C5 -179.59(9) . . . . ?
C18 C1 C6 C7 -0.47(15) . . . . ?
C18 C13 C14 C15 -0.76(16) . . . . ?
C19 C20 C21 F3 178.18(9) . . . . ?
C19 C20 C21 C22 -1.05(16) . . . . ?
C20 C19 C32 C23 1.57(16) . . . . ?
C20 C19 C32 C31 -178.11(10) . . . . ?
C20 C21 C22 F4 -179.79(9) . . . . ?
C20 C21 C22 C23 0.76(16) . . . . ?
C21 C22 C23 C24 -179.88(10) . . . . ?
C21 C22 C23 C32 0.69(15) . . . . ?
C22 C23 C24 F5 1.60(15) . . . . ?
C22 C23 C24 C25 -178.74(9) . . . . ?
C22 C23 C32 C19 -1.82(15) . . . . ?
C22 C23 C32 C31 177.88(9) . . . . ?
C23 C24 C25 C26 -178.24(10) . . . . ?
C23 C24 C25 C30 1.17(16) . . . . ?
C24 C23 C32 C19 178.72(9) . . . . ?
C24 C23 C32 C31 -1.58(15) . . . . ?
C24 C25 C26 F6 1.02(16) . . . . ?
C24 C25 C26 C27 179.45(10) . . . . ?
C24 C25 C30 C29 178.38(9) . . . . ?
C24 C25 C30 C31 -2.09(15) . . . . ?
C25 C26 C27 F7 -176.95(10) . . . . ?
C25 C26 C27 C28 1.88(18) . . . . ?
C25 C30 C31 F10 -179.16(9) . . . . ?
C25 C30 C31 C32 1.23(16) . . . . ?
C26 C25 C30 C29 -2.18(15) . . . . ?
C26 C25 C30 C31 177.34(9) . . . . ?
C26 C27 C28 F8 178.72(10) . . . . ?
C26 C27 C28 C29 -1.61(18) . . . . ?
C27 C28 C29 F9 178.61(10) . . . . ?
C27 C28 C29 C30 -0.64(18) . . . . ?
C28 C29 C30 C25 2.51(16) . . . . ?
C28 C29 C30 C31 -176.99(10) . . . . ?
C29 C30 C31 F10 0.34(16) . . . . ?
C29 C30 C31 C32 -179.28(10) . . . . ?
C30 C25 C26 F6 -178.38(9) . . . . ?
C30 C25 C26 C27 0.04(16) . . . . ?
C30 C31 C32 C19 -179.69(9) . . . . ?
C30 C31 C32 C23 0.63(16) . . . . ?
C32 C19 C20 F2 179.60(9) . . . . ?
C32 C19 C20 C21 -0.15(16) . . . . ?
C32 C23 C24 F5 -178.96(8) . . . . ?
C32 C23 C24 C25 0.69(16) . . . . ?

_olex2_date_sample_data_collection 2021-07-27
_olex2_date_sample_submission    2021-07-22
_olex2_exptl_crystal_mounting_method 
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id FR332
_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.541
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_TetDFA_Dimer_100K
_database_code_depnum_ccdc_archive 'CCDC 2293633'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details


loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de

_audit_creation_method           'CIF-fill 1.2x (K.Radacki, 2005-21)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H12 F10'
_chemical_formula_sum            'C32 H12 F10'
_chemical_formula_weight         586.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.9708(3)
_cell_length_b                   10.0237(4)
_cell_length_c                   12.7358(5)
_cell_angle_alpha                70.185(4)
_cell_angle_beta                 77.145(3)
_cell_angle_gamma                85.923(3)
_cell_volume                     1167.48(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14122
_cell_measurement_theta_min      3.7630
_cell_measurement_theta_max      74.2650


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_diffrn_ambient_environment      N~2~
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    1.347
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021) Empirical 
absorption correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     55.00  90.00   0.50    0.05    --   42.00  52.00 -32.11   70
   2  ω   -104.00 -67.00   0.50    0.05    --  -54.00 -45.00 123.29   74
   3  ω   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00 176.46   70
   4  ω   -108.00 -70.00   0.50    0.05    --  -58.00 -41.00  80.37   76
   5  ω   -106.00 -71.00   0.50    0.05    --  -58.00 -52.00  38.01   70
   6  ω   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00-105.69   70
   7  ω   -120.00 -34.00   0.50    0.05    --  -69.72 -15.00-120.00  172
   8  ω     29.00  79.00   0.50    0.05    --   71.50 -95.00 150.00  100
   9  ω    -97.00 -28.00   0.50    0.05    --  -76.37 112.00  60.00  138
  10  ω    -97.00 -28.00   0.50    0.05    --  -76.37 112.00 -30.00  138
  11  ω   -125.00 -90.00   0.50    0.05    --  -79.50 -62.00  -1.50   70
  12  ω   -125.00 -90.00   0.50    0.05    --  -79.50 -62.00-109.80   70
  13  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00  22.17   68
  14  ω   -102.00 -32.00   0.50    0.05    --  -79.50 128.00 177.19  140
  15  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00  60.00  100
  16  ω     46.00 133.00   0.50    0.05    --   82.31  15.00 -60.00  174
  17  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00   0.00  100
  18  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00 150.00  100
  19  ω     46.00 133.00   0.50    0.05    --   82.31  15.00  90.00  174
  20  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00-120.00  100
  21  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00-150.00  100
  22  ω     34.00  97.00   0.50    0.05    --   82.31-112.00-120.00  126
  23  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00 120.00  100
  24  ω     34.00  97.00   0.50    0.05    --   82.31-112.00 -90.00  126
  25  ω     46.00 133.00   0.50    0.05    --   82.31  15.00 120.00  174
  26  ω     34.00  97.00   0.50    0.05    --   82.31-112.00 -30.00  126
  27  ω     34.00  97.00   0.50    0.05    --   82.31-112.00 120.00  126
  28  ω     34.00  97.00   0.50    0.05    --   82.31-112.00  60.00  126
  29  ω     34.00  97.00   0.50    0.05    --   82.31-112.00 -60.00  126
  30  ω     34.00  97.00   0.50    0.05    --   82.31-112.00  90.00  126
  31  ω     34.00  97.00   0.50    0.05    --   82.31-112.00-180.00  126
  32  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00-180.00  100
  33  ω     46.00 133.00   0.50    0.05    --   82.31  15.00 -30.00  174
  34  ω     57.00  89.00   0.50    0.05    --   82.31 -95.00  90.00   64
  35  ω     72.00  97.00   0.50    0.05    --   82.31-112.00-150.00   50
  36  ω     45.00  97.00   0.50    0.05    --   82.31-112.00   0.00  104
  37  ω     71.00  96.00   0.50    0.05    --   82.31-112.00 150.00   50
  38  ω     98.00 131.00   0.50    0.05    --   85.25  45.00-153.25   66
  39  ω     89.00 136.00   0.50    0.05    --   85.25  23.00 157.20   94
  40  ω     96.00 121.00   0.50    0.05    --   85.25 127.00 112.19   50
  41  ω     75.00 133.00   0.50    0.05    --   85.25  22.00-148.93  116
  42  ω     51.00  77.00   0.50    0.05    --   85.25-116.00 -61.51   52
  43  ω     40.00  86.00   0.50    0.05    --   85.25-138.00 -27.22   92
  44  ω     64.00 127.00   0.50    0.05    --   85.25  12.00  28.43  126
  45  ω     38.00  94.00   0.50    0.05    --   85.25-130.00  67.96  112

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            23759
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.774
_diffrn_reflns_theta_max         74.319
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4668
_reflns_number_gt                4233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4668
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.44362(7) 0.69861(8) 0.35951(6) 0.02237(17) Uani 1 1 d . . . . .
F2 F 0.47132(8) 0.45411(8) 0.34200(7) 0.02726(19) Uani 1 1 d . . . . .
F3 F 0.56920(8) 0.29830(8) 0.21143(7) 0.02884(19) Uani 1 1 d . . . . .
F4 F 0.78508(8) 0.39109(8) 0.02917(7) 0.02859(19) Uani 1 1 d . . . . .
F5 F 0.89605(8) 0.64570(8) -0.02238(7) 0.02713(19) Uani 1 1 d . . . . .
F6 F 0.86354(7) 0.89201(8) -0.00802(6) 0.02237(17) Uani 1 1 d . . . . .
F7 F 0.75755(8) 1.13450(8) -0.05692(6) 0.02648(19) Uani 1 1 d . . . . .
F8 F 0.53796(8) 1.29403(8) -0.02776(7) 0.02779(19) Uani 1 1 d . . . . .
F9 F 0.32386(8) 1.19586(8) 0.15387(7) 0.02738(19) Uani 1 1 d . . . . .
F10 F 0.33683(8) 0.94241(8) 0.31053(7) 0.02732(19) Uani 1 1 d . . . . .
C1 C 0.57151(13) 0.74587(13) 0.29011(11) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.62272(13) 0.64696(13) 0.22186(11) 0.0195(3) Uani 1 1 d . . . . .
C3 C 0.57202(13) 0.51132(14) 0.25041(11) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.62459(14) 0.42700(13) 0.18458(11) 0.0231(3) Uani 1 1 d . . . . .
C5 C 0.73247(14) 0.47440(14) 0.09282(11) 0.0235(3) Uani 1 1 d . . . . .
C6 C 0.78758(13) 0.60823(14) 0.06539(11) 0.0217(3) Uani 1 1 d . . . . .
C7 C 0.73211(13) 0.69641(13) 0.12749(11) 0.0196(3) Uani 1 1 d . . . . .
C8 C 0.78570(13) 0.84459(13) 0.10295(10) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.66260(13) 0.94235(13) 0.11070(10) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.65565(13) 1.07713(14) 0.03332(11) 0.0206(3) Uani 1 1 d . . . . .
C11 C 0.54150(14) 1.16167(13) 0.04706(11) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.43432(13) 1.11236(14) 0.13925(11) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.44152(13) 0.97950(14) 0.21941(11) 0.0210(3) Uani 1 1 d . . . . .
C14 C 0.55419(13) 0.89254(13) 0.20568(11) 0.0191(3) Uani 1 1 d . . . . .
C15 C 0.67081(12) 0.74595(13) 0.37284(10) 0.0187(3) Uani 1 1 d . . . . .
H15 H 0.616594 0.711366 0.453215 0.022 Uiso 1 1 calc R U . . .
C16 C 0.79294(13) 0.64813(13) 0.36331(10) 0.0186(3) Uani 1 1 d . . . . .
C17 C 0.80073(13) 0.51646(13) 0.44158(10) 0.0197(3) Uani 1 1 d . . . . .
H17 H 0.728404 0.483814 0.506990 0.024 Uiso 1 1 calc R U . . .
C18 C 0.91619(13) 0.42786(13) 0.42600(10) 0.0193(3) Uani 1 1 d . . . . .
C19 C 0.92620(14) 0.29001(14) 0.50507(11) 0.0218(3) Uani 1 1 d . . . . .
H19 H 0.856346 0.256600 0.572213 0.026 Uiso 1 1 calc R U . . .
C20 C 1.03574(14) 0.20472(14) 0.48537(11) 0.0240(3) Uani 1 1 d . . . . .
H20 H 1.040718 0.112194 0.538407 0.029 Uiso 1 1 calc R U . . .
C21 C 1.14109(14) 0.25346(15) 0.38687(12) 0.0261(3) Uani 1 1 d . . . . .
H21 H 1.216166 0.193208 0.373568 0.031 Uiso 1 1 calc R U . . .
C22 C 1.13596(13) 0.38721(14) 0.31015(11) 0.0236(3) Uani 1 1 d . . . . .
H22 H 1.208344 0.419444 0.244740 0.028 Uiso 1 1 calc R U . . .
C23 C 1.02348(13) 0.47802(14) 0.32752(11) 0.0203(3) Uani 1 1 d . . . . .
C24 C 1.01426(13) 0.61691(13) 0.24903(10) 0.0200(3) Uani 1 1 d . . . . .
H24 H 1.086509 0.652173 0.183965 0.024 Uiso 1 1 calc R U . . .
C25 C 0.90236(13) 0.70020(13) 0.26632(10) 0.0188(3) Uani 1 1 d . . . . .
C26 C 0.88434(12) 0.84781(13) 0.18514(10) 0.0188(3) Uani 1 1 d . . . . .
H26 H 0.976640 0.883385 0.136652 0.023 Uiso 1 1 calc R U . . .
C27 C 0.83224(13) 0.94476(13) 0.25502(10) 0.0188(3) Uani 1 1 d . . . . .
C28 C 0.88944(13) 1.07671(13) 0.23174(11) 0.0208(3) Uani 1 1 d . . . . .
H28 H 0.962476 1.112454 0.167415 0.025 Uiso 1 1 calc R U . . .
C29 C 0.83970(13) 1.15664(14) 0.30272(11) 0.0230(3) Uani 1 1 d . . . . .
H29 H 0.879273 1.246629 0.286994 0.028 Uiso 1 1 calc R U . . .
C30 C 0.73231(13) 1.10504(14) 0.39650(11) 0.0226(3) Uani 1 1 d . . . . .
H30 H 0.698267 1.159978 0.444560 0.027 Uiso 1 1 calc R U . . .
C31 C 0.67462(13) 0.97294(14) 0.42004(11) 0.0203(3) Uani 1 1 d . . . . .
H31 H 0.601238 0.937676 0.484170 0.024 Uiso 1 1 calc R U . . .
C32 C 0.72434(12) 0.89270(13) 0.34978(10) 0.0186(2) 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
F1 C1 1.3900(14) . ?
F2 C3 1.3434(15) . ?
F3 C4 1.3433(14) . ?
F4 C5 1.3554(15) . ?
F5 C6 1.3399(15) . ?
F6 C8 1.3909(13) . ?
F7 C10 1.3414(14) . ?
F8 C11 1.3493(14) . ?
F9 C12 1.3534(15) . ?
F10 C13 1.3409(14) . ?
C1 C2 1.5212(17) . ?
C1 C14 1.5239(17) . ?
C1 C15 1.5985(17) . ?
C2 C3 1.3845(17) . ?
C2 C7 1.4034(17) . ?
C3 C4 1.3835(19) . ?
C4 C5 1.3730(19) . ?
C5 C6 1.3875(18) . ?
C6 C7 1.3866(18) . ?
C7 C8 1.5209(17) . ?
C8 C9 1.5222(17) . ?
C8 C26 1.5966(17) . ?
C9 C10 1.3841(18) . ?
C9 C14 1.4023(17) . ?
C10 C11 1.3852(18) . ?
C11 C12 1.3741(19) . ?
C12 C13 1.3850(18) . ?
C13 C14 1.3889(18) . ?
C15 C32 1.5113(17) . ?
C15 C16 1.5180(17) . ?
C15 H15 1.0000 . ?
C16 C17 1.3673(17) . ?
C16 C25 1.4258(17) . ?
C17 C18 1.4234(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.4195(17) . ?
C18 C23 1.4221(18) . ?
C19 C20 1.3702(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.4095(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.3708(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.4200(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.4230(18) . ?
C24 C25 1.3687(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.5159(17) . ?
C26 C27 1.5216(17) . ?
C26 H26 1.0000 . ?
C27 C28 1.3888(17) . ?
C27 C32 1.4005(17) . ?
C28 C29 1.3929(18) . ?
C28 H28 0.9500 . ?
C29 C30 1.3897(18) . ?
C29 H29 0.9500 . ?
C30 C31 1.3916(18) . ?
C30 H30 0.9500 . ?
C31 C32 1.3882(17) . ?
C31 H31 0.9500 . ?

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
F1 C1 C2 108.97(10) . . ?
F1 C1 C14 108.43(10) . . ?
C2 C1 C14 107.73(10) . . ?
F1 C1 C15 106.69(9) . . ?
C2 C1 C15 111.90(10) . . ?
C14 C1 C15 113.00(10) . . ?
C3 C2 C7 119.17(12) . . ?
C3 C2 C1 123.99(11) . . ?
C7 C2 C1 116.77(11) . . ?
F2 C3 C4 116.48(11) . . ?
F2 C3 C2 122.83(12) . . ?
C4 C3 C2 120.70(12) . . ?
F3 C4 C5 120.37(12) . . ?
F3 C4 C3 119.35(12) . . ?
C5 C4 C3 120.29(12) . . ?
F4 C5 C4 120.28(12) . . ?
F4 C5 C6 120.02(12) . . ?
C4 C5 C6 119.70(12) . . ?
F5 C6 C7 122.69(12) . . ?
F5 C6 C5 116.62(12) . . ?
C7 C6 C5 120.69(12) . . ?
C6 C7 C2 119.36(12) . . ?
C6 C7 C8 124.10(11) . . ?
C2 C7 C8 116.50(11) . . ?
F6 C8 C7 108.70(10) . . ?
F6 C8 C9 108.28(10) . . ?
C7 C8 C9 108.10(10) . . ?
F6 C8 C26 106.78(9) . . ?
C7 C8 C26 112.54(10) . . ?
C9 C8 C26 112.29(10) . . ?
C10 C9 C14 119.44(12) . . ?
C10 C9 C8 123.88(11) . . ?
C14 C9 C8 116.61(11) . . ?
F7 C10 C9 122.97(12) . . ?
F7 C10 C11 116.22(11) . . ?
C9 C10 C11 120.80(12) . . ?
F8 C11 C12 120.15(12) . . ?
F8 C11 C10 119.95(11) . . ?
C12 C11 C10 119.86(12) . . ?
F9 C12 C11 119.90(11) . . ?
F9 C12 C13 119.98(11) . . ?
C11 C12 C13 120.08(12) . . ?
F10 C13 C12 116.57(11) . . ?
F10 C13 C14 122.72(11) . . ?
C12 C13 C14 120.69(12) . . ?
C13 C14 C9 119.09(12) . . ?
C13 C14 C1 124.24(11) . . ?
C9 C14 C1 116.64(11) . . ?
C32 C15 C16 108.38(10) . . ?
C32 C15 C1 112.12(10) . . ?
C16 C15 C1 112.19(10) . . ?
C32 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C1 C15 H15 108.0 . . ?
C17 C16 C25 120.36(12) . . ?
C17 C16 C15 123.28(11) . . ?
C25 C16 C15 116.36(11) . . ?
C16 C17 C18 120.62(11) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C23 119.10(12) . . ?
C19 C18 C17 121.85(12) . . ?
C23 C18 C17 119.05(11) . . ?
C20 C19 C18 120.57(12) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.38(12) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.45(13) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.63(12) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 118.84(12) . . ?
C22 C23 C24 122.08(11) . . ?
C18 C23 C24 119.08(12) . . ?
C25 C24 C23 120.67(11) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C16 120.17(11) . . ?
C24 C25 C26 123.52(11) . . ?
C16 C25 C26 116.29(11) . . ?
C25 C26 C27 108.55(10) . . ?
C25 C26 C8 110.88(10) . . ?
C27 C26 C8 112.94(10) . . ?
C25 C26 H26 108.1 . . ?
C27 C26 H26 108.1 . . ?
C8 C26 H26 108.1 . . ?
C28 C27 C32 119.79(12) . . ?
C28 C27 C26 123.44(11) . . ?
C32 C27 C26 116.73(11) . . ?
C27 C28 C29 119.99(11) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.16(12) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.03(12) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C32 C31 C30 119.98(12) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.06(12) . . ?
C31 C32 C15 122.89(11) . . ?
C27 C32 C15 117.01(11) . . ?

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 C3 -18.40(17) . . . . ?
C14 C1 C2 C3 -135.85(12) . . . . ?
C15 C1 C2 C3 99.35(14) . . . . ?
F1 C1 C2 C7 164.48(11) . . . . ?
C14 C1 C2 C7 47.03(14) . . . . ?
C15 C1 C2 C7 -77.77(14) . . . . ?
C7 C2 C3 F2 177.29(11) . . . . ?
C1 C2 C3 F2 0.2(2) . . . . ?
C7 C2 C3 C4 -2.42(19) . . . . ?
C1 C2 C3 C4 -179.48(12) . . . . ?
F2 C3 C4 F3 3.23(18) . . . . ?
C2 C3 C4 F3 -177.04(11) . . . . ?
F2 C3 C4 C5 -176.67(12) . . . . ?
C2 C3 C4 C5 3.1(2) . . . . ?
F3 C4 C5 F4 -0.72(19) . . . . ?
C3 C4 C5 F4 179.18(12) . . . . ?
F3 C4 C5 C6 179.28(12) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
F4 C5 C6 F5 -2.52(18) . . . . ?
C4 C5 C6 F5 177.48(12) . . . . ?
F4 C5 C6 C7 177.97(11) . . . . ?
C4 C5 C6 C7 -2.0(2) . . . . ?
F5 C6 C7 C2 -176.85(11) . . . . ?
C5 C6 C7 C2 2.6(2) . . . . ?
F5 C6 C7 C8 0.8(2) . . . . ?
C5 C6 C7 C8 -179.74(12) . . . . ?
C3 C2 C7 C6 -0.40(19) . . . . ?
C1 C2 C7 C6 176.86(11) . . . . ?
C3 C2 C7 C8 -178.22(11) . . . . ?
C1 C2 C7 C8 -0.95(17) . . . . ?
C6 C7 C8 F6 19.11(17) . . . . ?
C2 C7 C8 F6 -163.19(11) . . . . ?
C6 C7 C8 C9 136.44(13) . . . . ?
C2 C7 C8 C9 -45.86(14) . . . . ?
C6 C7 C8 C26 -98.96(14) . . . . ?
C2 C7 C8 C26 78.74(14) . . . . ?
F6 C8 C9 C10 -18.91(16) . . . . ?
C7 C8 C9 C10 -136.51(12) . . . . ?
C26 C8 C9 C10 98.74(14) . . . . ?
F6 C8 C9 C14 164.16(10) . . . . ?
C7 C8 C9 C14 46.56(14) . . . . ?
C26 C8 C9 C14 -78.19(13) . . . . ?
C14 C9 C10 F7 177.15(11) . . . . ?
C8 C9 C10 F7 0.3(2) . . . . ?
C14 C9 C10 C11 -1.68(19) . . . . ?
C8 C9 C10 C11 -178.52(11) . . . . ?
F7 C10 C11 F8 -0.46(18) . . . . ?
C9 C10 C11 F8 178.44(11) . . . . ?
F7 C10 C11 C12 -178.09(11) . . . . ?
C9 C10 C11 C12 0.81(19) . . . . ?
F8 C11 C12 F9 1.18(18) . . . . ?
C10 C11 C12 F9 178.80(11) . . . . ?
F8 C11 C12 C13 -176.39(11) . . . . ?
C10 C11 C12 C13 1.23(19) . . . . ?
F9 C12 C13 F10 -1.58(18) . . . . ?
C11 C12 C13 F10 175.99(11) . . . . ?
F9 C12 C13 C14 -179.98(11) . . . . ?
C11 C12 C13 C14 -2.4(2) . . . . ?
F10 C13 C14 C9 -176.78(11) . . . . ?
C12 C13 C14 C9 1.52(19) . . . . ?
F10 C13 C14 C1 0.9(2) . . . . ?
C12 C13 C14 C1 179.23(12) . . . . ?
C10 C9 C14 C13 0.51(18) . . . . ?
C8 C9 C14 C13 177.58(11) . . . . ?
C10 C9 C14 C1 -177.37(11) . . . . ?
C8 C9 C14 C1 -0.30(16) . . . . ?
F1 C1 C14 C13 18.13(17) . . . . ?
C2 C1 C14 C13 135.93(12) . . . . ?
C15 C1 C14 C13 -99.93(14) . . . . ?
F1 C1 C14 C9 -164.11(10) . . . . ?
C2 C1 C14 C9 -46.31(14) . . . . ?
C15 C1 C14 C9 77.83(14) . . . . ?
F1 C1 C15 C32 -118.35(11) . . . . ?
C2 C1 C15 C32 122.55(11) . . . . ?
C14 C1 C15 C32 0.73(14) . . . . ?
F1 C1 C15 C16 119.42(10) . . . . ?
C2 C1 C15 C16 0.32(14) . . . . ?
C14 C1 C15 C16 -121.51(11) . . . . ?
C32 C15 C16 C17 133.83(12) . . . . ?
C1 C15 C16 C17 -101.84(14) . . . . ?
C32 C15 C16 C25 -46.43(14) . . . . ?
C1 C15 C16 C25 77.90(13) . . . . ?
C25 C16 C17 C18 -1.72(19) . . . . ?
C15 C16 C17 C18 178.01(11) . . . . ?
C16 C17 C18 C19 -179.16(12) . . . . ?
C16 C17 C18 C23 -0.17(18) . . . . ?
C23 C18 C19 C20 -1.80(19) . . . . ?
C17 C18 C19 C20 177.18(12) . . . . ?
C18 C19 C20 C21 0.8(2) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C23 -1.1(2) . . . . ?
C21 C22 C23 C18 0.05(19) . . . . ?
C21 C22 C23 C24 -179.37(12) . . . . ?
C19 C18 C23 C22 1.36(18) . . . . ?
C17 C18 C23 C22 -177.66(11) . . . . ?
C19 C18 C23 C24 -179.20(11) . . . . ?
C17 C18 C23 C24 1.78(18) . . . . ?
C22 C23 C24 C25 177.90(12) . . . . ?
C18 C23 C24 C25 -1.52(19) . . . . ?
C23 C24 C25 C16 -0.36(19) . . . . ?
C23 C24 C25 C26 -178.72(11) . . . . ?
C17 C16 C25 C24 2.01(19) . . . . ?
C15 C16 C25 C24 -177.74(11) . . . . ?
C17 C16 C25 C26 -179.51(11) . . . . ?
C15 C16 C25 C26 0.74(16) . . . . ?
C24 C25 C26 C27 -136.36(12) . . . . ?
C16 C25 C26 C27 45.21(14) . . . . ?
C24 C25 C26 C8 99.02(14) . . . . ?
C16 C25 C26 C8 -79.40(13) . . . . ?
F6 C8 C26 C25 -118.02(10) . . . . ?
C7 C8 C26 C25 1.18(14) . . . . ?
C9 C8 C26 C25 123.44(11) . . . . ?
F6 C8 C26 C27 119.89(10) . . . . ?
C7 C8 C26 C27 -120.91(11) . . . . ?
C9 C8 C26 C27 1.35(14) . . . . ?
C25 C26 C27 C28 131.49(12) . . . . ?
C8 C26 C27 C28 -105.13(13) . . . . ?
C25 C26 C27 C32 -45.98(14) . . . . ?
C8 C26 C27 C32 77.41(13) . . . . ?
C32 C27 C28 C29 0.17(19) . . . . ?
C26 C27 C28 C29 -177.22(12) . . . . ?
C27 C28 C29 C30 -0.39(19) . . . . ?
C28 C29 C30 C31 0.32(19) . . . . ?
C29 C30 C31 C32 -0.03(19) . . . . ?
C30 C31 C32 C27 -0.19(19) . . . . ?
C30 C31 C32 C15 177.37(11) . . . . ?
C28 C27 C32 C31 0.12(18) . . . . ?
C26 C27 C32 C31 177.69(11) . . . . ?
C28 C27 C32 C15 -177.58(11) . . . . ?
C26 C27 C32 C15 -0.02(16) . . . . ?
C16 C15 C32 C31 -131.40(12) . . . . ?
C1 C15 C32 C31 104.22(13) . . . . ?
C16 C15 C32 C27 46.23(14) . . . . ?
C1 C15 C32 C27 -78.15(13) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_TetDFA_Dimer_298K
_database_code_depnum_ccdc_archive 'CCDC 2293634'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

# 1. Submission Details

loop_
_audit_author_email
florian.rauch@uni-wuerzburg.de
pablo.durand@etu.unistra.fr
alexandra.friedrich1@uni-wuerzburg.de
leclercn@unistra.fr
todd.marder@uni-wuerzburg.de
_audit_creation_method           'CIF-fill 1.2y (K.Radacki, 2005-22)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H12 F10'
_chemical_formula_sum            'C32 H12 F10'
_chemical_formula_weight         586.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0716(3)
_cell_length_b                   10.1045(2)
_cell_length_c                   12.8392(4)
_cell_angle_alpha                70.147(2)
_cell_angle_beta                 76.929(3)
_cell_angle_gamma                85.958(2)
_cell_volume                     1197.10(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    15869
_cell_measurement_theta_min      3.7430
_cell_measurement_theta_max      74.2830


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    1.314
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021) 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   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 -2 0.1285
-1 -1 2 0.1570
-1 0 -1 0.0540
1 0 1 0.0624
-1 2 1 0.0835
-1 0 2 0.1398
1 0 -2 0.1308
1 5 -3 0.1349
1 2 -1 0.1290
2 2 -1 0.1266
-2 -2 1 0.1506
-2 0 1 0.1153
2 2 1 0.1015
1 0 0 0.1275
0 1 1 0.0647
0 -1 -1 0.0639
2 -5 -3 0.0753

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      297.98(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     14.00  71.00   0.50    0.05    --   58.61-102.00 -14.00  114
   2  ω    -73.00 -15.00   0.50    0.05    --  -60.19 102.00  88.00  116
   3  ω    -82.00 -25.00   0.50    0.05    --  -69.72 102.00  88.00  114
   4  ω     26.00  84.00   0.50    0.05    --   71.30-102.00 -14.00  116
   5  ω    -89.00 -31.00   0.50    0.05    --  -76.37 102.00  88.00  116
   6  ω     37.00  94.00   0.50    0.05    --   82.31-102.00 -14.00  114
   7  ω    -31.00  -5.00   0.50    0.05    --  -10.00 113.00-144.90   52
   8  ω     55.00  90.00   0.50    0.05    --   42.00  52.00-115.55   70
   9  ω   -102.00 -67.00   0.50    0.05    --  -54.00 -51.00 122.97   70
  10  ω   -102.00 -67.00   0.50    0.05    --  -54.00 -51.00  27.25   70
  11  ω   -102.00 -67.00   0.50    0.05    --  -54.00 -51.00 139.47   70
  12  ω   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00 166.58   70
  13  ω   -116.00 -79.00   0.50    0.05    --  -66.00 -46.00   4.87   74
  14  ω   -122.00 -81.00   0.50    0.05    --  -70.00 -35.00  75.88   82
  15  ω     29.00  79.00   0.50    0.05    --   71.30 -95.00  30.00  100
  16  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -60.00-112.39   68
  17  ω    -97.00 -28.00   0.50    0.05    --  -76.37 112.00  60.00  138
  18  ω    -97.00 -28.00   0.50    0.05    --  -76.37 112.00-120.00  138
  19  ω   -130.00 -92.00   0.50    0.05    --  -79.50 -43.00 -24.30   76
  20  ω   -107.00 -33.00   0.50    0.05    --  -79.50 138.00 158.31  148
  21  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00 -19.96   68
  22  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00-163.68   68
  23  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00  43.42   68
  24  ω   -130.00 -91.00   0.50    0.05    --  -79.50 -39.00 154.76   78
  25  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00 -57.72   70
  26  ω     34.00  97.00   0.50    0.05    --   82.31-112.00-180.00  126
  27  ω     46.00 133.00   0.50    0.05    --   82.31  15.00  90.00  174
  28  ω     46.00 133.00   0.50    0.05    --   82.31  15.00 -60.00  174
  29  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00 120.00  100
  30  ω     34.00  97.00   0.50    0.05    --   82.31-112.00  60.00  126
  31  ω     40.00  65.00   0.50    0.05    --   82.31 -95.00-180.00   50
  32  ω     40.00  65.00   0.50    0.05    --   82.31 -95.00   0.00   50
  33  ω     77.00 128.00   0.50    0.05    --   82.31  15.00-180.00  102
  34  ω     46.00  86.00   0.50    0.05    --   82.31  15.00  60.00   80
  35  ω     41.00  73.00   0.50    0.05    --   82.31 -95.00 -30.00   64
  36  ω     46.00  72.00   0.50    0.05    --   82.31  15.00-180.00   52
  37  ω     52.00  90.00   0.50    0.05    --   82.31 -95.00 -60.00   76
  38  ω     37.00  65.00   0.50    0.05    --   82.31-112.00 -30.00   56
  39  ω     42.00  97.00   0.50    0.05    --   82.31-112.00-150.00  110
  40  ω     41.00  78.00   0.50    0.05    --   82.31 -95.00  60.00   74
  41  ω     69.00  97.00   0.50    0.05    --   82.31-112.00 -60.00   56
  42  ω     41.00  70.00   0.50    0.05    --   82.31 -95.00 150.00   58
  43  ω    108.00 133.00   0.50    0.05    --   82.31  15.00-150.00   50
  44  ω     41.00  67.00   0.50    0.05    --   82.31-112.00 -60.00   52
  45  ω     71.00  97.00   0.50    0.05    --   82.31-112.00 150.00   52
  46  ω     92.00 127.00   0.50    0.05    --   82.31  15.00  60.00   70
  47  ω     71.00  97.00   0.50    0.05    --   82.31-112.00  30.00   52
  48  ω     40.00  65.00   0.50    0.05    --   82.31 -95.00  90.00   50
  49  ω     40.00  65.00   0.50    0.05    --   82.31 -95.00  30.00   50
  50  ω     45.00  70.00   0.50    0.05    --   85.25 -76.00-118.99   50
  51  ω     50.00  76.00   0.50    0.05    --   85.25-114.00  25.17   52
  52  ω     71.00  97.00   0.50    0.05    --   85.25-112.00 -83.92   52
  53  ω    100.00 132.00   0.50    0.05    --   85.25  55.00 -92.12   64
  54  ω     41.00  95.00   0.50    0.05    --   85.25-109.00-117.82  108
  55  ω    101.00 130.00   0.50    0.05    --   85.25  63.00-128.82   58
  56  ω     42.00  93.00   0.50    0.05    --   85.25-101.00 104.05  102
  57  ω    102.00 132.00   0.50    0.05    --   85.25  52.00 171.56   60
  58  ω    106.00 133.00   0.50    0.05    --   85.25 113.00-114.00   54
  59  ω    106.00 135.00   0.50    0.05    --   85.25  47.00  64.89   58

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            24611
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.748
_diffrn_reflns_theta_max         74.407
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4784
_reflns_number_gt                4219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.1948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4784
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.44647(7) 0.69823(8) 0.35828(6) 0.0529(2) Uani 1 1 d . . . . .
F2 F 0.47369(10) 0.45642(9) 0.34007(8) 0.0677(3) Uani 1 1 d . . . . .
F3 F 0.57078(11) 0.30230(9) 0.21046(9) 0.0745(3) Uani 1 1 d . . . . .
F4 F 0.78453(11) 0.39574(10) 0.02945(9) 0.0762(3) Uani 1 1 d . . . . .
F5 F 0.89450(9) 0.64756(9) -0.02142(7) 0.0663(2) Uani 1 1 d . . . . .
F6 F 0.86417(8) 0.89088(8) -0.00580(6) 0.0520(2) Uani 1 1 d . . . . .
F7 F 0.75807(9) 1.13043(9) -0.05458(7) 0.0653(2) Uani 1 1 d . . . . .
F8 F 0.53990(10) 1.28708(9) -0.02646(8) 0.0694(3) Uani 1 1 d . . . . .
F9 F 0.32863(10) 1.19011(10) 0.15438(8) 0.0725(3) Uani 1 1 d . . . . .
F10 F 0.34150(9) 0.93982(10) 0.30981(8) 0.0688(3) Uani 1 1 d . . . . .
C1 C 0.57322(12) 0.74487(13) 0.28938(10) 0.0418(3) Uani 1 1 d . . . . .
C2 C 0.62409(12) 0.64732(12) 0.22142(10) 0.0426(3) Uani 1 1 d . . . . .
C3 C 0.57368(14) 0.51338(13) 0.24910(11) 0.0488(3) Uani 1 1 d . . . . .
C4 C 0.62577(15) 0.43020(13) 0.18376(13) 0.0538(3) Uani 1 1 d . . . . .
C5 C 0.73241(15) 0.47788(15) 0.09285(13) 0.0549(3) Uani 1 1 d . . . . .
C6 C 0.78726(14) 0.60984(14) 0.06600(11) 0.0488(3) Uani 1 1 d . . . . .
C7 C 0.73282(13) 0.69671(13) 0.12771(10) 0.0426(3) Uani 1 1 d . . . . .
C8 C 0.78618(12) 0.84358(12) 0.10402(10) 0.0411(3) Uani 1 1 d . . . . .
C9 C 0.66448(12) 0.94026(12) 0.11182(10) 0.0414(3) Uani 1 1 d . . . . .
C10 C 0.65714(13) 1.07375(13) 0.03497(11) 0.0465(3) Uani 1 1 d . . . . .
C11 C 0.54403(15) 1.15680(13) 0.04867(12) 0.0502(3) Uani 1 1 d . . . . .
C12 C 0.43826(14) 1.10790(14) 0.14009(12) 0.0512(3) Uani 1 1 d . . . . .
C13 C 0.44550(13) 0.97667(14) 0.21949(11) 0.0481(3) Uani 1 1 d . . . . .
C14 C 0.55669(12) 0.89078(13) 0.20593(10) 0.0416(3) Uani 1 1 d . . . . .
C15 C 0.67087(12) 0.74423(12) 0.37141(10) 0.0405(3) Uani 1 1 d . . . . .
H15 H 0.617808 0.710147 0.449597 0.049 Uiso 1 1 calc R U . . .
C16 C 0.79194(12) 0.64734(12) 0.36183(10) 0.0398(3) Uani 1 1 d . . . . .
C17 C 0.79947(13) 0.51691(13) 0.43942(10) 0.0427(3) Uani 1 1 d . . . . .
H17 H 0.728817 0.484736 0.502767 0.051 Uiso 1 1 calc R U . . .
C18 C 0.91439(13) 0.42973(13) 0.42429(10) 0.0430(3) Uani 1 1 d . . . . .
C19 C 0.92451(15) 0.29350(14) 0.50288(12) 0.0507(3) Uani 1 1 d . . . . .
H19 H 0.856103 0.260306 0.567804 0.061 Uiso 1 1 calc R U . . .
C20 C 1.03401(16) 0.21062(15) 0.48396(13) 0.0590(4) Uani 1 1 d . . . . .
H20 H 1.039273 0.121051 0.535791 0.071 Uiso 1 1 calc R U . . .
C21 C 1.13837(17) 0.25932(17) 0.38723(14) 0.0643(4) Uani 1 1 d . . . . .
H21 H 1.211928 0.201399 0.374975 0.077 Uiso 1 1 calc R U . . .
C22 C 1.13337(15) 0.39100(16) 0.31062(13) 0.0574(4) Uani 1 1 d . . . . .
H22 H 1.204068 0.422485 0.247203 0.069 Uiso 1 1 calc R U . . .
C23 C 1.02120(13) 0.47998(14) 0.32710(11) 0.0452(3) Uani 1 1 d . . . . .
C24 C 1.01181(13) 0.61729(13) 0.24918(10) 0.0445(3) Uani 1 1 d . . . . .
H24 H 1.082122 0.651827 0.185941 0.053 Uiso 1 1 calc R U . . .
C25 C 0.90079(12) 0.69918(12) 0.26600(10) 0.0400(3) Uani 1 1 d . . . . .
C26 C 0.88306(12) 0.84559(12) 0.18552(10) 0.0402(3) Uani 1 1 d . . . . .
H26 H 0.972849 0.880289 0.138315 0.048 Uiso 1 1 calc R U . . .
C27 C 0.83180(12) 0.94121(12) 0.25522(10) 0.0408(3) Uani 1 1 d . . . . .
C28 C 0.88830(14) 1.07188(13) 0.23239(11) 0.0476(3) Uani 1 1 d . . . . .
H28 H 0.959418 1.106840 0.169889 0.057 Uiso 1 1 calc R U . . .
C29 C 0.83871(15) 1.15066(14) 0.30287(12) 0.0547(3) Uani 1 1 d . . . . .
H29 H 0.877237 1.237990 0.287764 0.066 Uiso 1 1 calc R U . . .
C30 C 0.73238(15) 1.09971(15) 0.39531(12) 0.0540(3) Uani 1 1 d . . . . .
H30 H 0.699246 1.152995 0.442045 0.065 Uiso 1 1 calc R U . . .
C31 C 0.67496(13) 0.96934(14) 0.41855(11) 0.0466(3) Uani 1 1 d . . . . .
H31 H 0.603191 0.935355 0.480688 0.056 Uiso 1 1 calc R U . . .
C32 C 0.72446(12) 0.88979(12) 0.34928(10) 0.0403(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3875(13) . ?
F2 C3 1.3427(15) . ?
F3 C4 1.3448(15) . ?
F4 C5 1.3533(15) . ?
F5 C6 1.3383(15) . ?
F6 C8 1.3884(12) . ?
F7 C10 1.3377(14) . ?
F8 C11 1.3465(15) . ?
F9 C12 1.3511(16) . ?
F10 C13 1.3390(15) . ?
C1 C2 1.5186(17) . ?
C1 C14 1.5240(16) . ?
C1 C15 1.5935(17) . ?
C2 C3 1.3800(17) . ?
C2 C7 1.4033(16) . ?
C3 C4 1.380(2) . ?
C4 C5 1.368(2) . ?
C5 C6 1.3811(19) . ?
C6 C7 1.3809(18) . ?
C7 C8 1.5217(16) . ?
C8 C9 1.5195(17) . ?
C8 C26 1.5895(17) . ?
C9 C10 1.3832(17) . ?
C9 C14 1.4005(16) . ?
C10 C11 1.3812(19) . ?
C11 C12 1.368(2) . ?
C12 C13 1.3801(19) . ?
C13 C14 1.3839(18) . ?
C15 C32 1.5147(16) . ?
C15 C16 1.5187(16) . ?
C15 H15 0.9800 . ?
C16 C17 1.3651(16) . ?
C16 C25 1.4224(15) . ?
C17 C18 1.4227(18) . ?
C17 H17 0.9300 . ?
C18 C19 1.4166(17) . ?
C18 C23 1.4183(17) . ?
C19 C20 1.365(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.399(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.4169(19) . ?
C22 H22 0.9300 . ?
C23 C24 1.4200(18) . ?
C24 C25 1.3650(17) . ?
C24 H24 0.9300 . ?
C25 C26 1.5153(16) . ?
C26 C27 1.5195(16) . ?
C26 H26 0.9800 . ?
C27 C28 1.3859(17) . ?
C27 C32 1.3999(16) . ?
C28 C29 1.3896(19) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.3860(19) . ?
C30 H30 0.9300 . ?
C31 C32 1.3835(17) . ?
C31 H31 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
F1 C1 C2 109.16(9) . . ?
F1 C1 C14 108.38(10) . . ?
C2 C1 C14 107.82(10) . . ?
F1 C1 C15 106.58(9) . . ?
C2 C1 C15 111.83(10) . . ?
C14 C1 C15 112.97(10) . . ?
C3 C2 C7 119.10(12) . . ?
C3 C2 C1 124.06(11) . . ?
C7 C2 C1 116.78(10) . . ?
F2 C3 C4 116.48(11) . . ?
F2 C3 C2 122.69(12) . . ?
C4 C3 C2 120.83(12) . . ?
F3 C4 C5 120.60(13) . . ?
F3 C4 C3 119.35(13) . . ?
C5 C4 C3 120.06(12) . . ?
F4 C5 C4 120.09(13) . . ?
F4 C5 C6 119.96(13) . . ?
C4 C5 C6 119.95(12) . . ?
F5 C6 C7 122.55(12) . . ?
F5 C6 C5 116.71(12) . . ?
C7 C6 C5 120.74(13) . . ?
C6 C7 C2 119.23(12) . . ?
C6 C7 C8 124.34(11) . . ?
C2 C7 C8 116.39(10) . . ?
F6 C8 C9 108.43(10) . . ?
F6 C8 C7 108.64(9) . . ?
C9 C8 C7 108.02(10) . . ?
F6 C8 C26 106.60(9) . . ?
C9 C8 C26 112.55(10) . . ?
C7 C8 C26 112.47(10) . . ?
C10 C9 C14 119.16(12) . . ?
C10 C9 C8 124.10(11) . . ?
C14 C9 C8 116.69(10) . . ?
F7 C10 C11 116.42(11) . . ?
F7 C10 C9 122.69(12) . . ?
C11 C10 C9 120.88(12) . . ?
F8 C11 C12 120.24(12) . . ?
F8 C11 C10 119.82(13) . . ?
C12 C11 C10 119.91(12) . . ?
F9 C12 C11 119.86(12) . . ?
F9 C12 C13 120.06(13) . . ?
C11 C12 C13 120.04(12) . . ?
F10 C13 C12 116.42(12) . . ?
F10 C13 C14 122.73(12) . . ?
C12 C13 C14 120.84(12) . . ?
C13 C14 C9 119.12(11) . . ?
C13 C14 C1 124.32(11) . . ?
C9 C14 C1 116.54(11) . . ?
C32 C15 C16 108.19(9) . . ?
C32 C15 C1 112.30(10) . . ?
C16 C15 C1 112.37(10) . . ?
C32 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C1 C15 H15 107.9 . . ?
C17 C16 C25 120.25(11) . . ?
C17 C16 C15 123.30(10) . . ?
C25 C16 C15 116.45(10) . . ?
C16 C17 C18 120.63(11) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C23 119.03(12) . . ?
C19 C18 C17 121.89(12) . . ?
C23 C18 C17 119.08(11) . . ?
C20 C19 C18 120.44(13) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.53(13) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.70(14) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.44(14) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 118.84(12) . . ?
C22 C23 C24 122.18(12) . . ?
C18 C23 C24 118.98(11) . . ?
C25 C24 C23 120.78(11) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C16 120.24(11) . . ?
C24 C25 C26 123.59(10) . . ?
C16 C25 C26 116.15(10) . . ?
C25 C26 C27 108.38(9) . . ?
C25 C26 C8 111.31(9) . . ?
C27 C26 C8 112.98(10) . . ?
C25 C26 H26 108.0 . . ?
C27 C26 H26 108.0 . . ?
C8 C26 H26 108.0 . . ?
C28 C27 C32 119.53(11) . . ?
C28 C27 C26 123.58(11) . . ?
C32 C27 C26 116.85(10) . . ?
C27 C28 C29 120.01(12) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.23(12) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.15(12) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 119.97(12) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.11(11) . . ?
C31 C32 C15 123.18(11) . . ?
C27 C32 C15 116.69(10) . . ?

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 C3 -18.21(17) . . . . ?
C14 C1 C2 C3 -135.75(13) . . . . ?
C15 C1 C2 C3 99.48(14) . . . . ?
F1 C1 C2 C7 164.46(10) . . . . ?
C14 C1 C2 C7 46.92(14) . . . . ?
C15 C1 C2 C7 -77.85(13) . . . . ?
C7 C2 C3 F2 177.22(12) . . . . ?
C1 C2 C3 F2 -0.1(2) . . . . ?
C7 C2 C3 C4 -2.2(2) . . . . ?
C1 C2 C3 C4 -179.46(12) . . . . ?
F2 C3 C4 F3 3.2(2) . . . . ?
C2 C3 C4 F3 -177.39(12) . . . . ?
F2 C3 C4 C5 -176.77(13) . . . . ?
C2 C3 C4 C5 2.7(2) . . . . ?
F3 C4 C5 F4 -0.7(2) . . . . ?
C3 C4 C5 F4 179.28(13) . . . . ?
F3 C4 C5 C6 179.57(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
F4 C5 C6 F5 -2.1(2) . . . . ?
C4 C5 C6 F5 177.63(13) . . . . ?
F4 C5 C6 C7 178.09(12) . . . . ?
C4 C5 C6 C7 -2.1(2) . . . . ?
F5 C6 C7 C2 -177.18(12) . . . . ?
C5 C6 C7 C2 2.6(2) . . . . ?
F5 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C8 -179.78(13) . . . . ?
C3 C2 C7 C6 -0.42(19) . . . . ?
C1 C2 C7 C6 177.05(11) . . . . ?
C3 C2 C7 C8 -178.24(11) . . . . ?
C1 C2 C7 C8 -0.77(16) . . . . ?
C6 C7 C8 F6 18.80(17) . . . . ?
C2 C7 C8 F6 -163.50(11) . . . . ?
C6 C7 C8 C9 136.23(13) . . . . ?
C2 C7 C8 C9 -46.08(14) . . . . ?
C6 C7 C8 C26 -98.95(14) . . . . ?
C2 C7 C8 C26 78.74(13) . . . . ?
F6 C8 C9 C10 -18.27(16) . . . . ?
C7 C8 C9 C10 -135.83(12) . . . . ?
C26 C8 C9 C10 99.40(13) . . . . ?
F6 C8 C9 C14 164.36(10) . . . . ?
C7 C8 C9 C14 46.80(14) . . . . ?
C26 C8 C9 C14 -77.98(13) . . . . ?
C14 C9 C10 F7 177.41(11) . . . . ?
C8 C9 C10 F7 0.1(2) . . . . ?
C14 C9 C10 C11 -1.48(19) . . . . ?
C8 C9 C10 C11 -178.80(12) . . . . ?
F7 C10 C11 F8 0.21(18) . . . . ?
C9 C10 C11 F8 179.17(11) . . . . ?
F7 C10 C11 C12 -178.03(12) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
F8 C11 C12 F9 0.7(2) . . . . ?
C10 C11 C12 F9 178.94(12) . . . . ?
F8 C11 C12 C13 -177.21(12) . . . . ?
C10 C11 C12 C13 1.0(2) . . . . ?
F9 C12 C13 F10 -1.7(2) . . . . ?
C11 C12 C13 F10 176.23(12) . . . . ?
F9 C12 C13 C14 179.67(12) . . . . ?
C11 C12 C13 C14 -2.4(2) . . . . ?
F10 C13 C14 C9 -176.73(12) . . . . ?
C12 C13 C14 C9 1.8(2) . . . . ?
F10 C13 C14 C1 1.2(2) . . . . ?
C12 C13 C14 C1 179.81(12) . . . . ?
C10 C9 C14 C13 0.10(18) . . . . ?
C8 C9 C14 C13 177.61(11) . . . . ?
C10 C9 C14 C1 -178.02(11) . . . . ?
C8 C9 C14 C1 -0.51(16) . . . . ?
F1 C1 C14 C13 17.71(17) . . . . ?
C2 C1 C14 C13 135.75(12) . . . . ?
C15 C1 C14 C13 -100.15(14) . . . . ?
F1 C1 C14 C9 -164.27(10) . . . . ?
C2 C1 C14 C9 -46.23(14) . . . . ?
C15 C1 C14 C9 77.86(13) . . . . ?
F1 C1 C15 C32 -118.14(10) . . . . ?
C2 C1 C15 C32 122.63(10) . . . . ?
C14 C1 C15 C32 0.77(13) . . . . ?
F1 C1 C15 C16 119.61(10) . . . . ?
C2 C1 C15 C16 0.38(13) . . . . ?
C14 C1 C15 C16 -121.48(11) . . . . ?
C32 C15 C16 C17 133.35(12) . . . . ?
C1 C15 C16 C17 -102.10(13) . . . . ?
C32 C15 C16 C25 -46.60(14) . . . . ?
C1 C15 C16 C25 77.95(13) . . . . ?
C25 C16 C17 C18 -1.53(18) . . . . ?
C15 C16 C17 C18 178.52(11) . . . . ?
C16 C17 C18 C19 -179.48(12) . . . . ?
C16 C17 C18 C23 -0.19(18) . . . . ?
C23 C18 C19 C20 -1.5(2) . . . . ?
C17 C18 C19 C20 177.79(13) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C22 0.7(2) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C21 C22 C23 C18 -0.1(2) . . . . ?
C21 C22 C23 C24 -179.67(14) . . . . ?
C19 C18 C23 C22 1.28(19) . . . . ?
C17 C18 C23 C22 -178.03(12) . . . . ?
C19 C18 C23 C24 -179.15(11) . . . . ?
C17 C18 C23 C24 1.54(18) . . . . ?
C22 C23 C24 C25 178.37(13) . . . . ?
C18 C23 C24 C25 -1.19(19) . . . . ?
C23 C24 C25 C16 -0.52(19) . . . . ?
C23 C24 C25 C26 -179.05(11) . . . . ?
C17 C16 C25 C24 1.90(18) . . . . ?
C15 C16 C25 C24 -178.14(11) . . . . ?
C17 C16 C25 C26 -179.46(11) . . . . ?
C15 C16 C25 C26 0.49(15) . . . . ?
C24 C25 C26 C27 -135.66(12) . . . . ?
C16 C25 C26 C27 45.75(14) . . . . ?
C24 C25 C26 C8 99.50(13) . . . . ?
C16 C25 C26 C8 -79.08(12) . . . . ?
F6 C8 C26 C25 -117.89(10) . . . . ?
C9 C8 C26 C25 123.37(10) . . . . ?
C7 C8 C26 C25 1.07(13) . . . . ?
F6 C8 C26 C27 119.90(10) . . . . ?
C9 C8 C26 C27 1.16(13) . . . . ?
C7 C8 C26 C27 -121.14(11) . . . . ?
C25 C26 C27 C28 131.47(12) . . . . ?
C8 C26 C27 C28 -104.69(13) . . . . ?
C25 C26 C27 C32 -46.39(14) . . . . ?
C8 C26 C27 C32 77.45(13) . . . . ?
C32 C27 C28 C29 0.23(19) . . . . ?
C26 C27 C28 C29 -177.57(12) . . . . ?
C27 C28 C29 C30 -0.5(2) . . . . ?
C28 C29 C30 C31 0.3(2) . . . . ?
C29 C30 C31 C32 0.2(2) . . . . ?
C30 C31 C32 C27 -0.48(19) . . . . ?
C30 C31 C32 C15 177.65(12) . . . . ?
C28 C27 C32 C31 0.26(18) . . . . ?
C26 C27 C32 C31 178.21(11) . . . . ?
C28 C27 C32 C15 -177.98(11) . . . . ?
C26 C27 C32 C15 -0.04(16) . . . . ?
C16 C15 C32 C31 -131.73(12) . . . . ?
C1 C15 C32 C31 103.68(13) . . . . ?
C16 C15 C32 C27 46.46(14) . . . . ?
C1 C15 C32 C27 -78.13(13) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.031



#=======================================================END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
