# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_exp_2920
_database_code_depnum_ccdc_archive 'CCDC 2483307'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:chloropentafluorobenzene
_chemical_formula_moiety         'C6 Cl F5, C8 H10'
_chemical_formula_sum            'C14 H10 Cl F5'
_chemical_formula_weight         308.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 F5 Cl C8 H10'
_chemical_oxdiff_usercomment     '0.3mm capillary'
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'
Cl Cl 0.3639 0.7018 '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                   6.5505(4)
_cell_length_b                   7.3190(4)
_cell_length_c                   14.6880(8)
_cell_angle_alpha                89.116(4)
_cell_angle_beta                 102.483(5)
_cell_angle_gamma                94.488(5)
_cell_volume                     685.43(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4754
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.3420
_cell_measurement_theta_min      6.0830
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.373
_exptl_absorpt_coefficient_mu    2.916
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 4 3 0.1151
4 1 -4 0.0396
2 -1 -9 0.0394
0 1 -9 0.0426
2 1 -9 0.0311
-2 1 9 0.0353
1 -5 -1 0.2278
-3 0 -4 0.0968
3 0 4 0.1050
-3 2 -2 0.1037

_exptl_crystal_preparation       '50:50 molar mixture of components'
_exptl_crystal_recrystallization_method 
'Crystal grown in situ from the melt in a 0.3mm X-ray capillary'
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.094
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.3433 3.9398 3.1338 0.0135 -0.5765 0.8170
3.9389 1.1403 -3.8572 0.7559 -0.6444 0.1155
2.1756 -0.7161 -8.9838 0.9531 0.1099 -0.2821
0.2252 0.5160 -9.3466 0.8430 0.5379 0.0093
2.0303 0.6809 -8.9897 0.9934 0.1139 0.0094
-2.1826 1.1121 8.8360 -0.9258 -0.1069 0.3626
0.8260 -4.6991 -1.2156 0.0027 -0.0089 -1.0000
-3.4863 0.0247 -3.6102 -0.0270 0.9988 0.0418
3.4837 -0.0060 3.6157 0.0270 -0.9989 -0.0379
-3.3057 2.4986 -2.3309 -0.0237 0.8269 0.5618

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11428
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.531
_diffrn_reflns_theta_min         6.065
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  21.00   1.00    1.00    --   34.00  92.00 -78.29   25
  2  ω     -4.00  21.00   1.00    1.00    --   34.00  92.00 142.09   25
  3  ω      3.00  28.00   1.00    1.00    --   38.00  86.00  71.42   25
  4  ω    -65.00  32.00   1.00    1.00    --  -42.62  38.00-150.00   97
  5  ω   -108.00 -23.00   1.00    1.00    --  -42.62 -38.00  30.00   85
  6  ω   -115.00 -19.00   1.00    1.00    --  -42.62 -38.00 120.00   96
  7  ω   -118.00 -16.00   1.00    1.00    --  -42.62 -19.00-150.00  102
  8  ω     27.00  99.00   1.00    1.00    --   42.62-125.00   0.00   72
  9  ω      7.00  74.00   1.00    1.00    --   42.62 -99.00  60.00   67
 10  ω     13.00  38.00   1.00    1.00    --   46.00  77.00-132.25   25
 11  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 -70.10   25
 12  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-111.25   25
 13  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 151.52   25
 14  ω     16.00  41.00   1.00    1.00    --   50.00  82.00  78.82   25
 15  ω     16.00  42.00   1.00    1.00    --   50.00  81.00 -10.61   26
 16  ω     31.00  58.00   1.00    1.00    --   62.00  71.00 166.29   27
 17  ω     32.00  58.00   1.00    1.00    --   62.00  71.00  -6.83   26
 18  ω    108.00 135.00   1.00    1.00    --   66.00  67.00  83.35   27
 19  ω     36.00  63.00   1.00    1.00    --   66.00  67.00  83.35   27
 20  ω     35.00  61.00   1.00    1.00    --   66.00  69.00 -43.92   26
 21  ω     40.00  67.00   1.00    1.00    --   70.00  70.00-152.86   27
 22  ω     39.00  72.00   1.00    1.00    --   70.00  69.00  29.45   33
 23  ω     40.00  66.00   1.00    1.00    --   70.00  66.00 -87.07   26
 24  ω     96.00 123.00   1.00    1.00    --   74.00  68.00-178.21   27
 25  ω     44.00  72.00   1.00    1.00    --   74.00  68.00-178.21   28
 26  ω     47.00  73.00   1.00    3.25    --   78.00  71.00  87.34   26
 27  ω     49.00  75.00   1.00    3.25    --   78.00  59.00  -0.86   26
 28  ω     52.00  89.00   1.00    3.25    --   82.00  66.00 127.19   37
 29  ω     51.00  79.00   1.00    3.25    --   82.00  70.00 -70.37   28
 30  ω     52.00  77.00   1.00    3.25    --   82.00  70.00-110.40   25
 31  ω     59.00  85.00   1.00    3.25    --   90.00  70.00-148.22   26
 32  ω     64.00 101.00   1.00    3.25    --   94.00  68.00  91.73   37
 33  ω     64.00 154.00   1.00    3.25    --   94.00  64.00  56.30   90
 34  ω    123.00 155.00   1.00    3.25    --   94.00  63.00   8.24   32
 35  ω     66.00  94.00   1.00    3.25    --   94.00  63.00   8.24   28
 36  ω    105.00 167.00   1.00    3.25    --   94.00  68.00  91.73   62
 37  ω     77.00 105.00   1.00    3.25    --  106.06  61.00 -90.00   28
 38  ω    105.00 131.00   1.00    3.25    --  106.06 -45.00 -60.00   26
 39  ω     34.00  89.00   1.00    3.25    --  106.06 -45.00 -60.00   55
 40  ω     48.00  75.00   1.00    3.25    --  106.06 -45.00-150.00   27
 41  ω     85.00 111.00   1.00    3.25    --  106.06-125.00-180.00   26
 42  ω     77.00 160.00   1.00    3.25    --  106.06  61.00 -60.00   83
 43  ω     77.00 178.00   1.00    3.25    --  106.06  61.00 -30.00  101
 44  ω     77.00 178.00   1.00    3.25    --  106.06  61.00-180.00  101
 45  ω     54.00 107.00   1.00    3.25    --  106.06 -94.00  30.00   53
 46  ω     77.00 177.00   1.00    3.25    --  106.06  61.00-120.00  100
 47  ω     77.00 156.00   1.00    3.25    --  106.06  61.00 150.00   79
 48  ω     77.00 175.00   1.00    3.25    --  106.06  61.00  30.00   98
 49  ω     26.00 107.00   1.00    3.25    --  106.06 -99.00 -47.36   81
 50  ω     45.00 112.00   1.00    3.25    --  106.06-125.00 -90.00   67
 51  ω    114.00 152.00   1.00    3.25    --  106.06  61.00-150.00   38
 52  ω     78.00 104.00   1.00    3.25    --  106.06  61.00-150.00   26
 53  ω    104.00 130.00   1.00    3.25    --  106.06 -45.00-150.00   26
 54  ω     38.00 132.00   1.00    3.25    --  106.06 -61.00  60.00   94
 55  ω    124.00 164.00   1.00    3.25    --  106.06  61.00 120.00   40
 56  ω     77.00 118.00   1.00    3.25    --  106.06  61.00 120.00   41
 57  ω    127.00 166.00   1.00    3.25    --  106.06  61.00 -90.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0967886409
_diffrn_orient_matrix_UB_12      0.0386110535
_diffrn_orient_matrix_UB_13      -0.0857253839
_diffrn_orient_matrix_UB_21      -0.2203743666
_diffrn_orient_matrix_UB_22      -0.0202918114
_diffrn_orient_matrix_UB_23      -0.0639790519
_diffrn_orient_matrix_UB_31      -0.0207893107
_diffrn_orient_matrix_UB_32      0.2065816859
_diffrn_orient_matrix_UB_33      0.0099047740
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1969
_reflns_number_total             2667
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     280
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0761
_refine_ls_restrained_S_all      1.007
_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)+(0.1151P)²+0.3650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2352
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Shared sites
{F1, Cl1}
{F4, Cl4}
3. Restrained distances
 C13-H13A \\sim C13-H13B \\sim C13-H13C \\sim C13-H13D \\sim C13-H13E \\sim
C13-H13F \\sim C14-H14A ~
 C14-H14B \\sim C14-H14C \\sim C14-H14D \\sim C14-H14E \\sim C14-H14F \\sim
C8-H8 \\sim C9-H9 \\sim C11-H11
 \\sim C12-H12
 with sigma of 0.01
 H13A-H13F \\sim H13F-H13B \\sim H13B-H13D \\sim H13D-H13C \\sim H13C-H13E
\\sim H13E-H13A \\sim H14A-
 H14F \\sim H14F-H14B \\sim H14B-H14D \\sim H14D-H14C \\sim H14C-H14E \\sim
H14E-H14A
 with sigma of 0.01
 C7-H13A \\sim C7-H13B \\sim C7-H13C \\sim C7-H13D \\sim C7-H13E \\sim C7-H13F
\\sim C10-H14A \\sim C10-
 H14B \\sim C10-H14C \\sim C10-H14D \\sim C10-H14E \\sim C10-H14F
 with sigma of 0.01
 C7-H8 \\sim C9-H8 \\sim C8-H9 \\sim C10-H9 \\sim C10-H11 \\sim C12-H11 \\sim
C11-H12 \\sim C7-H12
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
Uanis(F4) = Uanis(Cl4)
5. Others
 Sof(Cl1)=Sof(F4)=1-FVAR(1)
 Sof(F1)=Sof(Cl4)=FVAR(1)
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5) H13E(0.5) H13F(0.5)
 H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H14E(0.5) H14F(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7278(3) 0.8919(2) 0.96553(9) 0.1039(8) Uani 0.382(8) 1 d . . P A 1
Cl1 Cl 0.7278(3) 0.8919(2) 0.96553(9) 0.1039(8) Uani 0.618(8) 1 d . . P A 1
F4 F 0.3559(4) 0.8311(3) 0.57234(12) 0.1225(11) Uani 0.618(8) 1 d . . P A 1
Cl4 Cl 0.3559(4) 0.8311(3) 0.57234(12) 0.1225(11) Uani 0.382(8) 1 d . . P A 1
F2 F 0.9343(4) 0.9954(3) 0.8210(3) 0.1138(11) Uani 1 1 d . . . A 1
F3 F 0.7658(5) 0.9682(4) 0.6382(2) 0.1218(11) Uani 1 1 d . . . A 1
F5 F 0.1306(4) 0.7151(4) 0.7043(3) 0.1269(12) Uani 1 1 d . . . A 1
F6 F 0.3058(5) 0.7379(4) 0.8908(2) 0.1199(11) Uani 1 1 d . . . A 1
C1 C 0.6244(6) 0.8693(5) 0.8564(3) 0.0795(10) Uani 1 1 d . . . A 1
C2 C 0.7336(6) 0.9249(4) 0.7913(3) 0.0787(11) Uani 1 1 d . . . A 1
C3 C 0.6481(7) 0.9107(5) 0.6995(3) 0.0827(11) Uani 1 1 d . . . A 1
C4 C 0.4444(7) 0.8405(5) 0.6700(3) 0.0846(11) Uani 1 1 d . . . A 1
C5 C 0.3287(6) 0.7835(5) 0.7337(4) 0.0856(12) Uani 1 1 d . . . A 1
C6 C 0.4186(7) 0.7961(5) 0.8273(4) 0.0840(12) Uani 1 1 d . . . A 1
C7 C 0.6634(5) 0.3860(4) 0.8061(2) 0.0668(9) Uani 1 1 d D . . B 2
C8 C 0.6952(5) 0.4136(4) 0.7173(3) 0.0655(8) Uani 1 1 d D . . B 2
H8 H 0.830(3) 0.449(6) 0.7089(7) 0.098 Uiso 1 1 d D U . C 2
C9 C 0.5364(5) 0.3779(5) 0.6401(2) 0.0662(8) Uani 1 1 d D . . B 2
H9 H 0.563(2) 0.395(6) 0.5807(13) 0.099 Uiso 1 1 d D U . D 2
C10 C 0.3373(5) 0.3147(4) 0.6490(2) 0.0637(8) Uani 1 1 d D . . B 2
C11 C 0.3043(5) 0.2871(4) 0.7378(3) 0.0700(9) Uani 1 1 d D . . B 2
H11 H 0.173(3) 0.242(6) 0.7461(7) 0.105 Uiso 1 1 d D U . E 2
C12 C 0.4646(6) 0.3218(5) 0.8151(2) 0.0726(9) Uani 1 1 d D . . B 2
H12 H 0.440(2) 0.299(6) 0.8741(13) 0.109 Uiso 1 1 d D U . F 2
C13 C 0.8393(8) 0.4213(6) 0.8902(3) 0.1067(16) Uani 1 1 d D . . B 2
H13A H 0.929(9) 0.327(7) 0.896(4) 0.160 Uiso 0.5 1 d D U P G 2
H13B H 0.784(5) 0.426(13) 0.9435(19) 0.160 Uiso 0.5 1 d D U P H 2
H13C H 0.914(10) 0.532(7) 0.883(4) 0.160 Uiso 0.5 1 d D U P I 2
H13D H 0.823(9) 0.530(7) 0.919(4) 0.160 Uiso 0.5 1 d D U P J 2
H13E H 0.967(4) 0.431(13) 0.872(2) 0.160 Uiso 0.5 1 d D U P K 2
H13F H 0.838(10) 0.325(7) 0.932(3) 0.160 Uiso 0.5 1 d D U P L 2
C14 C 0.1625(7) 0.2816(7) 0.5638(4) 0.1101(17) Uani 1 1 d D . . B 2
H14A H 0.157(11) 0.385(6) 0.526(4) 0.165 Uiso 0.5 1 d D U P M 2
H14B H 0.036(4) 0.259(13) 0.582(2) 0.165 Uiso 0.5 1 d D U P N 2
H14C H 0.189(9) 0.181(9) 0.531(4) 0.165 Uiso 0.5 1 d D U P O 2
H14D H 0.097(10) 0.165(6) 0.567(4) 0.165 Uiso 0.5 1 d D U P P 2
H14E H 0.218(5) 0.291(13) 0.5105(17) 0.165 Uiso 0.5 1 d D U P Q 2
H14F H 0.066(9) 0.369(9) 0.561(4) 0.165 Uiso 0.5 1 d D U P R 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.605(5) . ?
F4 C4 1.426(5) . ?
F2 C2 1.355(5) . ?
F3 C3 1.348(5) . ?
F5 C5 1.336(4) . ?
F6 C6 1.354(5) . ?
C1 C2 1.353(6) . ?
C1 C6 1.390(6) . ?
C2 C3 1.346(6) . ?
C3 C4 1.372(6) . ?
C4 C5 1.368(7) . ?
C5 C6 1.375(7) . ?
C7 C8 1.374(5) . ?
C7 C12 1.382(5) . ?
C7 C13 1.505(5) . ?
C8 H8 0.933(19) . ?
C8 C9 1.377(5) . ?
C9 H9 0.930(19) . ?
C9 C10 1.382(5) . ?
C10 C11 1.376(5) . ?
C10 C14 1.511(5) . ?
C11 H11 0.929(19) . ?
C11 C12 1.381(5) . ?
C12 H12 0.927(19) . ?
C13 H13A 0.93(2) . ?
C13 H13B 0.93(2) . ?
C13 H13C 0.93(2) . ?
C13 H13D 0.93(2) . ?
C13 H13E 0.93(2) . ?
C13 H13F 0.93(2) . ?
C14 H14A 0.93(2) . ?
C14 H14B 0.93(2) . ?
C14 H14C 0.93(2) . ?
C14 H14D 0.93(2) . ?
C14 H14E 0.93(2) . ?
C14 H14F 0.93(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 F1 120.8(3) . . ?
C2 C1 C6 118.8(4) . . ?
C6 C1 F1 120.3(4) . . ?
C1 C2 F2 118.0(4) . . ?
C3 C2 F2 120.3(4) . . ?
C3 C2 C1 121.7(4) . . ?
F3 C3 C4 121.4(5) . . ?
C2 C3 F3 118.7(4) . . ?
C2 C3 C4 119.9(4) . . ?
C3 C4 F4 118.8(4) . . ?
C5 C4 F4 121.1(4) . . ?
C5 C4 C3 120.1(4) . . ?
F5 C5 C4 119.6(5) . . ?
F5 C5 C6 120.9(4) . . ?
C4 C5 C6 119.5(4) . . ?
F6 C6 C1 120.2(5) . . ?
F6 C6 C5 119.8(4) . . ?
C5 C6 C1 120.0(4) . . ?
C8 C7 C12 117.4(3) . . ?
C8 C7 C13 121.2(4) . . ?
C12 C7 C13 121.4(4) . . ?
C7 C8 H8 119.4(7) . . ?
C7 C8 C9 121.6(3) . . ?
C9 C8 H8 118.9(7) . . ?
C8 C9 H9 120.0(7) . . ?
C8 C9 C10 121.0(3) . . ?
C10 C9 H9 119.0(7) . . ?
C9 C10 C14 120.6(3) . . ?
C11 C10 C9 117.7(3) . . ?
C11 C10 C14 121.8(3) . . ?
C10 C11 H11 119.7(7) . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 H11 119.2(7) . . ?
C7 C12 H12 119.1(7) . . ?
C11 C12 C7 121.3(3) . . ?
C11 C12 H12 119.6(7) . . ?
C7 C13 H13A 110(2) . . ?
C7 C13 H13B 110(2) . . ?
C7 C13 H13C 110(2) . . ?
C7 C13 H13D 110(2) . . ?
C7 C13 H13E 110(2) . . ?
C7 C13 H13F 110(2) . . ?
H13A C13 H13B 109(2) . . ?
H13A C13 H13C 109(2) . . ?
H13A C13 H13D 140(4) . . ?
H13A C13 H13E 56.1(9) . . ?
H13A C13 H13F 56.1(9) . . ?
H13B C13 H13C 109(2) . . ?
H13B C13 H13D 56.1(9) . . ?
H13B C13 H13E 141(4) . . ?
H13B C13 H13F 56.1(9) . . ?
H13C C13 H13D 56.2(9) . . ?
H13C C13 H13E 56.2(9) . . ?
H13C C13 H13F 141(4) . . ?
H13D C13 H13E 109(2) . . ?
H13D C13 H13F 109(2) . . ?
H13E C13 H13F 109(2) . . ?
C10 C14 H14A 109(2) . . ?
C10 C14 H14B 109(2) . . ?
C10 C14 H14C 109(2) . . ?
C10 C14 H14D 109(2) . . ?
C10 C14 H14E 109(2) . . ?
C10 C14 H14F 109(2) . . ?
H14A C14 H14B 110(2) . . ?
H14A C14 H14C 109(2) . . ?
H14A C14 H14D 141(4) . . ?
H14A C14 H14E 56.2(9) . . ?
H14A C14 H14F 56.3(9) . . ?
H14B C14 H14C 110(2) . . ?
H14B C14 H14D 56.4(9) . . ?
H14B C14 H14E 141(4) . . ?
H14B C14 H14F 56.4(9) . . ?
H14C C14 H14D 56.3(9) . . ?
H14C C14 H14E 56.2(9) . . ?
H14C C14 H14F 141(4) . . ?
H14D C14 H14E 109(2) . . ?
H14D C14 H14F 110(2) . . ?
H14E C14 H14F 109(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 1.7(5) . . . . ?
F1 C1 C2 C3 -178.6(3) . . . . ?
F1 C1 C6 F6 -2.1(5) . . . . ?
F1 C1 C6 C5 177.6(3) . . . . ?
F4 C4 C5 F5 1.0(5) . . . . ?
F4 C4 C5 C6 -179.4(3) . . . . ?
F2 C2 C3 F3 -0.1(5) . . . . ?
F2 C2 C3 C4 -179.5(3) . . . . ?
F3 C3 C4 F4 -0.8(5) . . . . ?
F3 C3 C4 C5 -179.9(3) . . . . ?
F5 C5 C6 F6 0.3(5) . . . . ?
F5 C5 C6 C1 -179.4(3) . . . . ?
C1 C2 C3 F3 -179.8(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C1 C6 F6 179.4(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C2 C3 C4 F4 178.5(3) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 F5 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 F6 -179.2(3) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C6 C1 C2 F2 -179.8(3) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C8 C7 C12 C11 -0.1(5) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C8 C9 C10 C14 178.1(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C7 0.2(5) . . . . ?
C12 C7 C8 C9 -0.4(5) . . . . ?
C13 C7 C8 C9 178.6(3) . . . . ?
C13 C7 C12 C11 -179.1(3) . . . . ?
C14 C10 C11 C12 -178.6(3) . . . . ?

_olex2_date_sample_data_collection 2021-09-30
_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 14.431
_oxdiff_exptl_absorpt_empirical_full_min 0.318
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2971
_database_code_depnum_ccdc_archive 'CCDC 2483310'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'1,4-dichlorotetrafluorobenzene 1,4-dimethylbenzene'
_chemical_formula_moiety         'C6 Cl2 F4, C8 H10'
_chemical_formula_sum            'C14 H10 Cl2 F4'
_chemical_formula_weight         325.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 F4 Cl2 C8 H10'
_chemical_oxdiff_usercomment     
'Repeat experiment no. 3 - same 0.3mm capillary - melt is around 280K'
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'
Cl Cl 0.3639 0.7018 '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                   6.4620(4)
_cell_length_b                   7.4574(4)
_cell_length_c                   15.1315(7)
_cell_angle_alpha                90.380(4)
_cell_angle_beta                 100.429(5)
_cell_angle_gamma                94.132(5)
_cell_volume                     715.13(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4544
_cell_measurement_temperature    240
_cell_measurement_theta_max      72.5060
_cell_measurement_theta_min      5.9130
_shelx_estimated_absorpt_T_max   0.720
_shelx_estimated_absorpt_T_min   0.341
_exptl_absorpt_coefficient_mu    4.401
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 -4 0.1354
-1 -4 4 0.0579
2 3 -5 0.0755
1 4 -4 0.0749
-4 2 2 0.1487
3 -1 5 0.1314
1 2 8 0.0804
0 -2 -8 0.0100
-1 -2 -8 0.0082
0 0 10 0.0444
1 0 -10 0.0197
-1 -2 9 0.0543

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Grown from the melt in 0.3mm X-ray capillary'
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.1178 -0.3872 -3.5807 0.6001 0.1102 0.7923
-0.7033 -4.3683 3.9746 -0.8938 -0.1672 0.4162
2.2125 3.4911 -4.7294 0.9825 0.1830 -0.0344
0.8388 4.3188 -4.0646 0.9070 0.1696 -0.3856
-3.8529 2.2194 1.9419 -0.2301 -0.0410 -0.9723
3.0175 -0.5537 5.4141 -0.0455 0.7537 0.6556
1.2058 1.7914 7.8539 -0.0617 0.9968 0.0498
-0.4948 -2.4040 -7.9416 0.0614 -0.9859 0.1554
-1.0681 -1.9196 -7.8979 0.0619 -0.9980 -0.0091
-0.0560 -0.3503 9.6688 -0.5933 0.8007 0.0829
0.5911 -0.1340 -9.8071 0.5940 -0.8011 0.0740
-0.9520 -1.8998 9.0153 -0.8663 0.4894 0.0996

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10480
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.271
_diffrn_reflns_theta_min         5.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  21.00   1.00    2.50    --   34.00  91.00 -44.79   25
  2  ω      7.00  32.00   1.00    2.50    --   42.00  84.00  84.25   25
  3  ω   -117.00 -60.00   1.00    2.50    --  -42.87 -38.00-120.00   57
  4  ω    -57.00 -23.00   1.00    2.50    --  -42.87 -38.00-120.00   34
  5  ω    -68.00  31.00   1.00    2.50    --  -42.87  77.00-180.00   99
  6  ω   -115.00 -24.00   1.00    2.50    --  -42.87 -38.00 120.00   91
  7  ω     15.00  42.00   1.00    2.50    --   42.87  57.00-120.00   27
  8  ω     28.00  93.00   1.00    2.50    --   42.87-125.00  30.00   65
  9  ω     10.00  36.00   1.00    2.50    --   42.87  77.00  32.79   26
 10  ω     17.00  42.00   1.00    2.50    --   50.00  81.00-156.83   25
 11  ω     16.00  41.00   1.00    2.50    --   50.00  82.00  -2.18   25
 12  ω     16.00  42.00   1.00    2.50    --   50.00  82.00 107.97   26
 13  ω     16.00  41.00   1.00    2.50    --   50.00  81.00 -94.85   25
 14  ω     16.00  41.00   1.00    2.50    --   50.00  82.00 -46.38   25
 15  ω     37.00  82.00   1.00    2.50    --   62.00  53.00  53.92   45
 16  ω     35.00  64.00   1.00    2.50    --   66.00  69.00-171.29   29
 17  ω     41.00  79.00   1.00    2.50    --   66.00  51.00 -61.76   38
 18  ω    110.00 137.00   1.00    2.50    --   70.00  69.00 141.78   27
 19  ω     40.00  69.00   1.00    2.50    --   70.00  69.00 141.78   29
 20  ω     43.00  90.00   1.00    2.50    --   74.00  69.00 -26.90   47
 21  ω     47.00  81.00   1.00    2.50    --   74.00  62.00 118.72   34
 22  ω     50.00 103.00   1.00   10.00    --   78.00  67.00  52.69   53
 23  ω     47.00 105.00   1.00   10.00    --   78.00  70.00-147.55   58
 24  ω     55.00  82.00   1.00   10.00    --   82.00  60.00 128.19   27
 25  ω    121.00 157.00   1.00   10.00    --   86.00  66.00  27.75   36
 26  ω     59.00  97.00   1.00   10.00    --   86.00  66.00  27.75   38
 27  ω     61.00  93.00   1.00   10.00    --   90.00  60.00 -52.01   32
 28  ω    127.00 163.00   1.00   10.00    --   90.00  68.00-155.19   36
 29  ω     68.00  94.00   1.00   10.00    --   90.00  68.00-155.19   26
 30  ω     61.00  87.00   1.00   10.00    --   90.00  60.00 -79.19   26
 31  ω     77.00 178.00   1.00   10.00    --  106.06  61.00 120.00  101
 32  ω     80.00 164.00   1.00   10.00    --  106.06  61.00-120.00   84
 33  ω     34.00  72.00   1.00   10.00    --  106.06 -61.00  30.00   38
 34  ω    121.00 174.00   1.00   10.00    --  106.06  45.00   0.00   53
 35  ω     81.00 119.00   1.00   10.00    --  106.06  45.00   0.00   38
 36  ω     91.00 129.00   1.00   10.00    --  106.06 -61.00-150.00   38
 37  ω    146.00 173.00   1.00   10.00    --  106.06  61.00  60.00   27
 38  ω     34.00 106.00   1.00   10.00    --  106.06-125.00 150.00   72
 39  ω     78.00 103.00   1.00   10.00    --  106.06  61.00  60.00   25
 40  ω     24.00 106.00   1.00   10.00    --  106.06 -94.00-150.00   82
 41  ω     69.00 100.00   1.00   10.00    --  106.06 -94.00 150.00   31
 42  ω     41.00 112.00   1.00   10.00    --  106.06-125.00  60.00   71
 43  ω     23.00  68.00   1.00   10.00    --  106.06 -94.00 150.00   45
 44  ω     35.00 107.00   1.00   10.00    --  106.06 -94.00 -90.00   72
 45  ω     84.00 139.00   1.00   10.00    --  106.06  45.00  30.00   55
 46  ω    150.00 177.00   1.00   10.00    --  106.06  45.00  30.00   27
 47  ω    109.00 134.00   1.00   10.00    --  106.06  61.00 150.00   25
 48  ω     78.00 103.00   1.00   10.00    --  106.06  61.00 150.00   25
 49  ω     77.00 162.00   1.00   10.00    --  106.06  61.00-180.00   85
 50  ω     77.00 174.00   1.00   10.00    --  106.06  61.00  76.54   97
 51  ω     77.00 171.00   1.00   10.00    --  106.06  61.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1100121000
_diffrn_orient_matrix_UB_12      0.1361241000
_diffrn_orient_matrix_UB_13      -0.0557953000
_diffrn_orient_matrix_UB_21      0.1118267000
_diffrn_orient_matrix_UB_22      0.0994939000
_diffrn_orient_matrix_UB_23      0.0870630000
_diffrn_orient_matrix_UB_31      0.1856925000
_diffrn_orient_matrix_UB_32      -0.1203613000
_diffrn_orient_matrix_UB_33      0.0052908000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1903
_reflns_number_total             2776
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.032
_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)+(0.0939P)²+0.1444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 C13-H13A \\sim C13-H13E \\sim C13-H13B \\sim C13-H13F \\sim C13-H13C \\sim
C13-H13D
 with sigma of 0.01
 C7-H13A \\sim C7-H13E \\sim C7-H13B \\sim C7-H13F \\sim C7-H13C \\sim C7-H13D
 with sigma of 0.01
 H13A-H13F \\sim H13F-H13B \\sim H13B-H13D \\sim H13D-H13C \\sim H13C-H13E
\\sim H13E-H13A
 with sigma of 0.01
 C14-H14A \\sim C14-H14F \\sim C14-H14B \\sim C14-H14D \\sim C14-H14C \\sim
C14-H14E
 with sigma of 0.01
 C10-H14A \\sim C10-H14F \\sim C10-H14B \\sim C10-H14D \\sim C10-H14C \\sim
C10-H14E
 with sigma of 0.01
 H14A-H14F \\sim H14F-H14B \\sim H14B-H14D \\sim H14D-H14C \\sim H14C-H14E
\\sim H14E-H14A
 with sigma of 0.01
3. Others
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5) H13E(0.5) H13F(0.5)
 H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H14E(0.5) H14F(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.26259(16) 0.11353(14) 0.02953(6) 0.0930(4) Uani 1 1 d . . . A 1
Cl2 Cl 0.65783(18) 0.16411(14) 0.43471(6) 0.1012(4) Uani 1 1 d . . . A 1
F1 F 0.0601(3) 0.0019(3) 0.17974(14) 0.0818(6) Uani 1 1 d . . . A 1
F2 F 0.2286(3) 0.0234(3) 0.35472(14) 0.0888(6) Uani 1 1 d . . . A 1
F3 F 0.8635(3) 0.2801(3) 0.28446(17) 0.0955(7) Uani 1 1 d . . . A 1
F4 F 0.6917(3) 0.2616(3) 0.10934(16) 0.0967(7) Uani 1 1 d . . . A 1
C1 C 0.3724(4) 0.1299(4) 0.1413(2) 0.0610(7) Uani 1 1 d . . . A 1
C2 C 0.2597(4) 0.0717(4) 0.2051(2) 0.0605(7) Uani 1 1 d . . . A 1
C3 C 0.3449(5) 0.0820(4) 0.2945(2) 0.0634(7) Uani 1 1 d . . . A 1
C4 C 0.5508(5) 0.1513(4) 0.3231(2) 0.0646(7) Uani 1 1 d . . . A 1
C5 C 0.6641(4) 0.2112(4) 0.2595(2) 0.0664(8) Uani 1 1 d . . . A 1
C6 C 0.5772(5) 0.2014(4) 0.1694(2) 0.0653(7) Uani 1 1 d . . . A 1
C7 C 0.3348(5) 0.6141(4) 0.1910(2) 0.0701(8) Uani 1 1 d D . . B 2
C8 C 0.2967(5) 0.5769(4) 0.2754(2) 0.0687(8) Uani 1 1 d . . . B 2
H8 H 0.162(6) 0.532(5) 0.286(3) 0.092(11) Uiso 1 1 d . . . C 2
C9 C 0.4505(5) 0.6035(4) 0.3504(2) 0.0688(8) Uani 1 1 d . . . B 2
H9 H 0.430(5) 0.577(5) 0.410(3) 0.086(11) Uiso 1 1 d . . . D 2
C10 C 0.6541(5) 0.6694(4) 0.3443(2) 0.0684(8) Uani 1 1 d D . . B 2
C11 C 0.6914(5) 0.7078(4) 0.2599(3) 0.0791(10) Uani 1 1 d . . . B 2
H11 H 0.833(7) 0.750(5) 0.257(3) 0.103(12) Uiso 1 1 d . . . E 2
C12 C 0.5372(7) 0.6795(5) 0.1849(3) 0.0823(10) Uani 1 1 d . . . B 2
H12 H 0.557(7) 0.699(6) 0.130(3) 0.105(14) Uiso 1 1 d . . . F 2
C13 C 0.1654(8) 0.5827(6) 0.1089(3) 0.1122(16) Uani 1 1 d D . . B 2
H13A H 0.074(10) 0.481(8) 0.115(3) 0.168 Uiso 0.5 1 d DR . P G 2
H13B H 0.224(6) 0.564(13) 0.057(2) 0.168 Uiso 0.5 1 d DR . P H 2
H13C H 0.083(10) 0.682(7) 0.098(4) 0.168 Uiso 0.5 1 d DR . P I 2
H13D H 0.180(10) 0.670(9) 0.065(3) 0.168 Uiso 0.5 1 d DR . P J 2
H13E H 0.030(5) 0.588(13) 0.123(3) 0.168 Uiso 0.5 1 d DR . P K 2
H13F H 0.171(11) 0.469(7) 0.082(4) 0.168 Uiso 0.5 1 d DR . P L 2
C14 C 0.8241(7) 0.6947(6) 0.4265(4) 0.1117(16) Uani 1 1 d D . . B 2
H14A H 0.777(6) 0.689(13) 0.483(2) 0.168 Uiso 0.5 1 d DR . P M 2
H14B H 0.908(11) 0.807(7) 0.431(4) 0.168 Uiso 0.5 1 d DR . P N 2
H14C H 0.929(10) 0.609(9) 0.433(4) 0.168 Uiso 0.5 1 d DR . P O 2
H14D H 0.965(5) 0.714(13) 0.415(2) 0.168 Uiso 0.5 1 d DR . P P 2
H14E H 0.835(11) 0.597(7) 0.467(4) 0.168 Uiso 0.5 1 d DR . P Q 2
H14F H 0.814(10) 0.794(9) 0.465(4) 0.168 Uiso 0.5 1 d DR . P R 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.711(3) . ?
Cl2 C4 1.705(3) . ?
F1 C2 1.343(3) . ?
F2 C3 1.339(3) . ?
F3 C5 1.339(3) . ?
F4 C6 1.332(3) . ?
C1 C2 1.367(4) . ?
C1 C6 1.381(4) . ?
C2 C3 1.364(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.369(5) . ?
C5 C6 1.377(5) . ?
C7 C8 1.369(5) . ?
C7 C12 1.382(5) . ?
C7 C13 1.504(5) . ?
C8 H8 0.95(4) . ?
C8 C9 1.369(5) . ?
C9 H9 0.95(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.370(5) . ?
C10 C14 1.505(5) . ?
C11 H11 0.95(4) . ?
C11 C12 1.372(6) . ?
C12 H12 0.87(4) . ?
C13 H13A 0.94(3) . ?
C13 H13B 0.95(3) . ?
C13 H13C 0.94(3) . ?
C13 H13D 0.94(3) . ?
C13 H13E 0.94(3) . ?
C13 H13F 0.94(3) . ?
C14 H14A 0.96(3) . ?
C14 H14B 0.96(3) . ?
C14 H14C 0.96(3) . ?
C14 H14D 0.96(3) . ?
C14 H14E 0.96(3) . ?
C14 H14F 0.96(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 Cl1 120.7(2) . . ?
C2 C1 C6 118.2(3) . . ?
C6 C1 Cl1 121.0(2) . . ?
F1 C2 C1 119.5(3) . . ?
F1 C2 C3 118.8(3) . . ?
C3 C2 C1 121.7(3) . . ?
F2 C3 C2 119.6(3) . . ?
F2 C3 C4 119.9(3) . . ?
C2 C3 C4 120.4(3) . . ?
C3 C4 Cl2 120.5(2) . . ?
C5 C4 Cl2 121.3(2) . . ?
C5 C4 C3 118.2(3) . . ?
F3 C5 C4 120.0(3) . . ?
F3 C5 C6 118.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
F4 C6 C1 120.1(3) . . ?
F4 C6 C5 119.6(3) . . ?
C5 C6 C1 120.2(3) . . ?
C8 C7 C12 116.7(3) . . ?
C8 C7 C13 121.6(3) . . ?
C12 C7 C13 121.6(4) . . ?
C7 C8 H8 122(2) . . ?
C9 C8 C7 122.0(3) . . ?
C9 C8 H8 116(2) . . ?
C8 C9 H9 124(2) . . ?
C8 C9 C10 121.3(3) . . ?
C10 C9 H9 115(2) . . ?
C9 C10 C14 121.2(4) . . ?
C11 C10 C9 116.6(3) . . ?
C11 C10 C14 122.2(3) . . ?
C10 C11 H11 115(3) . . ?
C10 C11 C12 121.9(3) . . ?
C12 C11 H11 123(3) . . ?
C7 C12 H12 114(3) . . ?
C11 C12 C7 121.5(4) . . ?
C11 C12 H12 124(3) . . ?
C7 C13 H13A 111(2) . . ?
C7 C13 H13B 111(2) . . ?
C7 C13 H13C 111(2) . . ?
C7 C13 H13D 111(2) . . ?
C7 C13 H13E 111(2) . . ?
C7 C13 H13F 111(2) . . ?
H13A C13 H13B 108(2) . . ?
H13A C13 H13C 108(2) . . ?
H13A C13 H13D 138(4) . . ?
H13A C13 H13E 55.7(10) . . ?
H13A C13 H13F 55.6(10) . . ?
H13B C13 H13C 108(2) . . ?
H13B C13 H13D 55.5(10) . . ?
H13B C13 H13E 138(4) . . ?
H13B C13 H13F 55.5(10) . . ?
H13C C13 H13D 55.5(10) . . ?
H13C C13 H13E 55.6(10) . . ?
H13C C13 H13F 137(4) . . ?
H13D C13 H13E 108(2) . . ?
H13D C13 H13F 108(2) . . ?
H13E C13 H13F 108(2) . . ?
C10 C14 H14A 116(2) . . ?
C10 C14 H14B 116(2) . . ?
C10 C14 H14C 116(2) . . ?
C10 C14 H14D 116(2) . . ?
C10 C14 H14E 116(2) . . ?
C10 C14 H14F 116(2) . . ?
H14A C14 H14B 103(3) . . ?
H14A C14 H14C 103(3) . . ?
H14A C14 H14D 128(4) . . ?
H14A C14 H14E 53.6(11) . . ?
H14A C14 H14F 53.5(11) . . ?
H14B C14 H14C 102(3) . . ?
H14B C14 H14D 53.5(11) . . ?
H14B C14 H14E 128(4) . . ?
H14B C14 H14F 53.6(11) . . ?
H14C C14 H14D 53.4(11) . . ?
H14C C14 H14E 53.4(11) . . ?
H14C C14 H14F 128(4) . . ?
H14D C14 H14E 102(3) . . ?
H14D C14 H14F 103(3) . . ?
H14E C14 H14F 102(3) . . ?

_olex2_date_sample_data_collection 2021-10-27
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.201
_oxdiff_exptl_absorpt_empirical_full_min 0.383
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_102
_database_code_depnum_ccdc_archive 'CCDC 2483308'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:chloropentafluorobenzene
_chemical_formula_moiety         'C6 Cl F5, C8 H10'
_chemical_formula_sum            'C14 H10 Cl F5'
_chemical_formula_weight         308.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 C6 F5 Cl'
_chemical_oxdiff_usercomment     '0.2mm capillary '
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.2099(4)
_cell_length_b                   7.4687(4)
_cell_length_c                   7.9874(4)
_cell_angle_alpha                109.801(5)
_cell_angle_beta                 99.549(5)
_cell_angle_gamma                95.567(5)
_cell_volume                     339.00(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.2830
_cell_measurement_theta_min      5.9600
_shelx_estimated_absorpt_T_max   0.586
_shelx_estimated_absorpt_T_min   0.174
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.196
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             156
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 -2 0.4541
1 -5 2 0.4541
3 1 -4 0.0988
4 1 -3 0.1026
-4 -1 3 0.1064
4 1 -2 0.1055
-4 -1 2 0.1045
4 1 -1 0.1045
-4 -1 1 0.1036
-4 -1 -1 0.1036
4 1 1 0.1064
-3 -1 -2 0.1017
3 1 2 0.1055
2 1 3 0.1045
-2 -1 -3 0.1026
-1 0 -4 0.1026
1 1 4 0.1045
0 0 4 0.1055
0 0 -5 0.1026
1 0 -5 0.1045
-1 0 5 0.1045
-2 0 5 0.1036
2 0 -5 0.1036
-2 0 4 0.1017
2 0 -4 0.1017
-2 0 4 0.1017

_exptl_crystal_preparation       '1:1 molar ratio (1/100 mole)'
_exptl_crystal_recrystallization_method 'Grown in 0.2 mm capillary'
_exptl_crystal_size_max          0.912
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.203
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0487 4.7781 -1.7331 -0.0028 -0.0194 -0.9998
1.0487 -4.7781 1.7331 0.0028 0.0194 0.9998
3.2054 0.5031 -3.7774 0.2326 0.9725 -0.0091
3.6482 0.6340 -2.9205 -0.0095 0.9999 -0.0091
-3.6390 -0.6767 2.9362 0.0095 -0.9998 0.0180
3.8811 0.7352 -1.8124 -0.2680 0.9634 -0.0091
-3.8620 -0.8220 1.8447 0.2679 -0.9631 0.0273
3.8489 0.7892 -0.5820 -0.5082 0.8612 -0.0091
-3.8394 -0.8330 0.5985 0.5081 -0.8611 0.0182
-3.5444 -0.8362 -0.6703 0.7137 -0.7002 0.0182
3.5446 0.8351 0.6708 -0.7137 0.7002 -0.0180
-3.0064 -0.7892 -1.8909 0.8706 -0.4916 0.0184
2.9973 0.8306 1.8748 -0.8704 0.4916 -0.0271
2.2438 0.7791 2.9468 -0.9677 0.2495 -0.0363
-2.2718 -0.6489 -2.9980 0.9683 -0.2496 0.0090
-1.3815 -0.4677 -3.8993 1.0000 0.0096 -0.0002
1.3542 0.5990 3.8483 -0.9996 -0.0095 -0.0272
0.3699 0.3864 4.4844 -0.9633 -0.2680 -0.0181
-0.3788 -0.3433 -4.5012 0.9634 0.2680 0.0090
0.6413 -0.1540 -4.8121 0.8612 0.5082 0.0091
-0.6413 0.1540 4.8121 -0.8612 -0.5082 -0.0091
-1.6182 -0.0427 4.7940 -0.7003 -0.7138 -0.0091
1.6182 0.0427 -4.7940 0.7003 0.7138 0.0091
-2.4578 -0.3678 4.4978 -0.4916 -0.8706 0.0190
2.4578 0.3678 -4.4978 0.4916 0.8706 -0.0190
-2.4855 -0.2336 4.4480 -0.4917 -0.8707 -0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5047
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.227
_diffrn_reflns_theta_min         7.023
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  76.00   0.50    3.00    --   49.93-131.00  83.00   76
  2  ω     61.00  88.00   0.50    3.00    --   49.93-139.00 -90.00   54
  3  ω    107.00 132.00   0.50   12.00    --  102.88 131.00 155.00   50
  4  ω    112.00 138.00   0.50   12.00    --  102.88 139.00 -30.00   52
  5  ω     65.00  90.00   0.50   12.00    --  102.88-139.00 -90.00   50
  6  ω     86.00 114.00   0.50   12.00    --  102.88-131.00  83.00   56
  7  ω    -57.00 -30.00   0.50    3.00    --   14.00 160.00-103.18   54
  8  ω    -56.00 -31.00   0.50    3.00    --   14.00 158.00 106.74   50
  9  ω    -53.00 -28.00   0.50    3.00    --   14.00 153.00  -1.08   50
 10  ω      8.00  40.00   0.50    3.00    --   30.00  82.00  24.17   64
 11  ω      1.00  26.00   0.50    3.00    --   30.00  93.00 144.12   50
 12  ω     38.00  79.00   0.50    3.00    --   49.93 -99.00-120.00   82
 13  ω      8.00  52.00   0.50    3.00    --   49.93 -77.00  30.00   88
 14  ω     31.00  56.00   0.50    3.00    --   49.93  77.00 120.00   50
 15  ω     -6.00  45.00   0.50    3.00    --   49.93 -77.00 -90.00  102
 16  ω     39.00  68.00   0.50    3.00    --   49.93  19.00-180.00   58
 17  ω     30.00  56.00   0.50    3.00    --   49.93  77.00-120.00   52
 18  ω     30.00  71.00   0.50    3.00    --   49.93  77.00 -90.00   82
 19  ω     30.00  56.00   0.50    3.00    --   49.93  77.00  90.00   52
 20  ω     36.00  79.00   0.50    3.00    --   54.00  77.00-179.95   86
 21  ω     90.00 117.00   0.50    3.00    --   54.00  77.00-179.95   54
 22  ω     37.00  64.00   0.50    3.00    --   54.00  76.00  18.96   54
 23  ω     92.00 117.00   0.50    3.00    --   54.00  76.00  18.96   50
 24  ω     37.00  72.00   0.50    3.00    --   54.00  72.00 158.42   70
 25  ω     38.00  64.00   0.50    3.00    --   54.00  73.00 -26.94   52
 26  ω     43.00  88.00   0.50    3.00    --   58.00  71.00  89.63   90
 27  ω     88.00 125.00   0.50    3.00    --   58.00  52.00-127.77   74
 28  ω     48.00  73.00   0.50    3.00    --   58.00  52.00-127.77   50
 29  ω     41.00  74.00   0.50    3.00    --   58.00  73.00  43.65   66
 30  ω     47.00  86.00   0.50    3.00    --   62.00  69.00  -8.71   78
 31  ω     47.00 116.00   0.50    3.00    --   62.00  66.00 -61.01  138
 32  ω     49.00  75.00   0.50    3.00    --   66.00  74.00-110.66   52
 33  ω     96.00 129.00   0.50    3.00    --   66.00  74.00-110.66   66
 34  ω     54.00  88.00   0.50    3.00    --   70.00  72.00 132.92   68
 35  ω     95.00 132.00   0.50    3.00    --   70.00  72.00 132.92   74
 36  ω     63.00 143.00   0.50   12.00    --   82.00  77.00 -24.55  160
 37  ω     71.00 114.00   0.50   12.00    --   86.00  66.00  73.83   86
 38  ω    122.00 152.00   0.50   12.00    --   86.00  66.00  73.83   60
 39  ω     89.00 114.00   0.50   12.00    --  102.88  77.00 120.00   50
 40  ω     99.00 170.00   0.50   12.00    --  102.88  38.00-150.00  142
 41  ω     98.00 155.00   0.50   12.00    --  102.88  57.00  30.00  114
 42  ω     82.00 112.00   0.50   12.00    --  102.88 -77.00  90.00   60
 43  ω     47.00  76.00   0.50   12.00    --  102.88 -77.00  90.00   58
 44  ω     96.00 136.00   0.50   12.00    --  102.88  38.00 150.00   80
 45  ω     85.00 136.00   0.50   12.00    --  102.88  77.00 150.00  102
 46  ω     91.00 152.00   0.50   12.00    --  102.88  57.00  90.00  122
 47  ω    137.00 169.00   0.50   12.00    --  102.88  38.00 -60.00   64
 48  ω     97.00 134.00   0.50   12.00    --  102.88  57.00-120.00   74
 49  ω     87.00 146.00   0.50   12.00    --  102.88  77.00-120.00  118
 50  ω     98.00 145.00   0.50   12.00    --  102.88  38.00 -30.00   94
 51  ω     96.00 123.00   0.50   12.00    --  102.88  38.00 -60.00   54
 52  ω     83.00 109.00   0.50   12.00    --  102.88  77.00-150.00   52
 53  ω     78.00 108.00   0.50   12.00    --  102.88-125.00 -30.00   60
 54  ω     83.00 114.00   0.50   12.00    --  102.88 -57.00 -90.00   62
 55  ω     40.00  65.00   0.50   12.00    --  102.88-125.00 -30.00   50
 56  ω     91.00 140.00   0.50   12.00    --  102.88  57.00  60.00   98
 57  ω     40.00  78.00   0.50   12.00    --  102.88 -57.00 -90.00   76
 58  ω     93.00 119.00   0.50   12.00    --  102.88  57.00 150.00   52
 59  ω     91.00 118.00   0.50   12.00    --  102.88  57.00 -60.00   54
 60  ω     44.00  92.00   0.50   12.00    --  102.88 -77.00  30.00   96
 61  ω    114.00 139.00   0.50   12.00    --  102.88  77.00   0.00   50
 62  ω     84.00 110.00   0.50   12.00    --  102.88  77.00   0.00   52
 63  ω     98.00 125.00   0.50   12.00    --  102.88  57.00-180.00   54
 64  ω     74.00 130.00   0.50   12.00    --  108.01 -20.00  19.43  112
 65  ω     38.00  70.00   0.50   12.00    --  108.01 -20.00  19.43   64
 66  ω     48.00 115.00   0.50   12.00    --  108.01 -50.00 119.76  134
 67  ω     76.00 105.00   0.50   12.00    --  108.01 -99.00-143.33   58
 68  ω     38.00 109.00   0.50   12.00    --  108.01 -49.00 -71.32  142
 69  ω     39.00  97.00   0.50   12.00    --  108.01 -58.00-139.98  116
 70  ω     44.00 114.00   0.50   12.00    --  108.01 -70.00  51.57  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1405342000
_diffrn_orient_matrix_UB_12      -0.1019558000
_diffrn_orient_matrix_UB_13      -0.1944247000
_diffrn_orient_matrix_UB_21      0.2091618000
_diffrn_orient_matrix_UB_22      0.0134854000
_diffrn_orient_matrix_UB_23      -0.0781700000
_diffrn_orient_matrix_UB_31      0.0395162000
_diffrn_orient_matrix_UB_32      -0.1970611000
_diffrn_orient_matrix_UB_33      0.0096924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1160
_reflns_number_total             1349
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1349
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.125
_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)+(0.0880P)²+0.1208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Shared sites
{F1, Cl1}
3. Restrained distances
 H7a-H7b \\sim H7b-H7c \\sim H7c-H7d \\sim H7d-H7e \\sim H7e-H7f \\sim H7f-H7a
 with sigma of 0.01
 C7-H7a \\sim C7-H7e \\sim C7-H7b \\sim C7-H7f \\sim C7-H7c \\sim C7-H7d \\sim
C4-H4 \\sim C5-H5
 with sigma of 0.01
 C6-H7a \\sim C6-H7e \\sim C6-H7b \\sim C6-H7f \\sim C6-H7c \\sim C6-H7d
 with sigma of 0.01
 C4-H5 \\sim C6-H5
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(Cl1)
5. Others
 Fixed Sof: Cl1(0.5) F1(0.5) H7a(0.5) H7b(0.5) H7c(0.5) H7d(0.5) H7e(0.5)
 H7f(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3144(2) -0.10905(19) 0.11260(15) 0.0855(5) Uani 0.5 1 d . . P A 1
F1 F 0.3144(2) -0.10905(19) 0.11260(15) 0.0855(5) Uani 0.5 1 d . . P A 1
F2 F 0.7553(3) 0.0786(3) 0.2792(3) 0.0816(6) Uani 1 1 d . . . A 1
F3 F 0.9257(3) 0.1812(3) 0.6386(3) 0.0810(6) Uani 1 1 d . . . A 1
C1 C 0.4129(5) -0.0521(4) 0.3170(4) 0.0649(7) Uani 1 1 d . . . A 1
C2 C 0.6284(4) 0.0395(4) 0.3889(4) 0.0623(7) Uani 1 1 d . . . A 1
C3 C 0.7153(4) 0.0911(4) 0.5691(5) 0.0630(7) Uani 1 1 d . . . A 1
C4 C 0.7188(5) 0.5771(4) 0.5422(5) 0.0689(8) Uani 1 1 d D . . B 2
H4 H 0.871(4) 0.627(5) 0.577(5) 0.089(11) Uiso 1 1 d D . . C 2
C5 C 0.6023(5) 0.5183(4) 0.3670(5) 0.0697(8) Uani 1 1 d D . . B 2
H5 H 0.669(3) 0.538(5) 0.276(3) 0.090(11) Uiso 1 1 d D . . D 2
C6 C 0.3785(5) 0.4399(4) 0.3194(4) 0.0675(8) Uani 1 1 d D . . B 2
C7 C 0.2496(9) 0.3781(7) 0.1259(7) 0.1096(15) Uani 1 1 d D . . B 2
H7A H 0.157(12) 0.469(8) 0.119(6) 0.164 Uiso 0.5 1 d D U P E 2
H7B H 0.098(4) 0.359(13) 0.126(5) 0.164 Uiso 0.5 1 d D U P F 2
H7C H 0.164(12) 0.256(7) 0.095(6) 0.164 Uiso 0.5 1 d D U P G 2
H7D H 0.291(12) 0.262(8) 0.056(5) 0.164 Uiso 0.5 1 d D U P H 2
H7E H 0.350(6) 0.373(13) 0.049(5) 0.164 Uiso 0.5 1 d D U P I 2
H7F H 0.284(12) 0.476(7) 0.081(6) 0.164 Uiso 0.5 1 d D U P J 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.539(3) . ?
F2 C2 1.353(3) . ?
F3 C3 1.343(3) . ?
C1 C2 1.375(4) . ?
C1 C3 1.386(4) 2_656 ?
C2 C3 1.356(5) . ?
C3 C1 1.386(4) 2_656 ?
C4 H4 0.94(2) . ?
C4 C5 1.364(5) . ?
C4 C6 1.381(5) 2_666 ?
C5 H5 0.94(2) . ?
C5 C6 1.391(5) . ?
C6 C4 1.381(5) 2_666 ?
C6 C7 1.509(6) . ?
C7 H7A 0.94(2) . ?
C7 H7B 0.94(2) . ?
C7 H7C 0.94(2) . ?
C7 H7D 0.94(2) . ?
C7 H7E 0.94(2) . ?
C7 H7F 0.94(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 Cl1 120.3(3) . . ?
C2 C1 C3 119.3(3) . 2_656 ?
C3 C1 Cl1 120.3(3) 2_656 . ?
F2 C2 C1 119.9(3) . . ?
F2 C2 C3 119.6(3) . . ?
C3 C2 C1 120.5(3) . . ?
F3 C3 C1 119.6(3) . 2_656 ?
F3 C3 C2 120.2(3) . . ?
C2 C3 C1 120.2(3) . 2_656 ?
C5 C4 H4 123(2) . . ?
C5 C4 C6 121.8(3) . 2_666 ?
C6 C4 H4 115(2) 2_666 . ?
C4 C5 H5 120.6(7) . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 117.7(7) . . ?
C4 C6 C5 116.7(3) 2_666 . ?
C4 C6 C7 122.0(3) 2_666 . ?
C5 C6 C7 121.3(4) . . ?
C6 C7 H7A 108(2) . . ?
C6 C7 H7B 108(2) . . ?
C6 C7 H7C 108(2) . . ?
C6 C7 H7D 109(2) . . ?
C6 C7 H7E 109(2) . . ?
C6 C7 H7F 108(2) . . ?
H7A C7 H7B 56.6(10) . . ?
H7A C7 H7C 110(2) . . ?
H7A C7 H7D 143(5) . . ?
H7A C7 H7E 110(2) . . ?
H7A C7 H7F 56.6(10) . . ?
H7B C7 H7C 56.6(10) . . ?
H7B C7 H7D 110(2) . . ?
H7B C7 H7E 143(5) . . ?
H7B C7 H7F 110(2) . . ?
H7C C7 H7D 56.6(10) . . ?
H7C C7 H7E 110(2) . . ?
H7C C7 H7F 143(5) . . ?
H7D C7 H7E 56.6(10) . . ?
H7D C7 H7F 110(2) . . ?
H7E C7 H7F 56.7(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
Cl1 C1 C2 F2 -0.5(4) . . . . ?
Cl1 C1 C2 C3 179.5(2) . . . . ?
F2 C2 C3 F3 0.3(4) . . . . ?
F2 C2 C3 C1 180.0(2) . . . 2_656 ?
C1 C2 C3 F3 -179.8(2) . . . . ?
C1 C2 C3 C1 -0.1(5) . . . 2_656 ?
C3 C1 C2 F2 -180.0(2) 2_656 . . . ?
C3 C1 C2 C3 0.1(4) 2_656 . . . ?
C4 C5 C6 C4 -0.6(5) . . . 2_666 ?
C4 C5 C6 C7 179.0(3) . . . . ?
C6 C4 C5 C6 0.7(5) 2_666 . . . ?

_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 2.480
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_78
_database_code_depnum_ccdc_archive 'CCDC 2483315'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2022-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        Iodofluorobenzene:p-xylene
_chemical_formula_moiety         'C6 F5 I, C4 H5'
_chemical_formula_sum            'C10 H5 F5 I'
_chemical_formula_weight         347.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 (C6 F5 I)2'
_chemical_oxdiff_usercomment     '0.3mm capillary'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.0419(2)
_cell_length_b                   8.9855(2)
_cell_length_c                   9.9890(3)
_cell_angle_alpha                74.629(2)
_cell_angle_beta                 89.584(2)
_cell_angle_gamma                89.675(2)
_cell_volume                     522.88(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7680
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.1010
_cell_measurement_theta_min      3.5450
_shelx_estimated_absorpt_T_max   0.404
_shelx_estimated_absorpt_T_min   0.162
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.181
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             326
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 11 4 0.1672
7 -6 -4 0.4560
-7 6 4 0.4570
-1 3 -12 0.2243
-4 -11 -5 0.1891
1 -3 12 0.1406
4 11 5 0.1720
4 11 -2 0.1900
-4 -11 2 0.1843
2 8 -8 0.2090
-3 -3 -13 0.2166
-4 -8 -11 0.2081
4 8 11 0.1682
-2 -8 8 0.1482
3 3 13 0.1387
-4 -11 -3 0.1796
-3 -10 4 0.1531
5 9 9 0.1550

_exptl_crystal_preparation       'Grown in situ from melt'
_exptl_crystal_recrystallization_method 'Grown in situ from melt'
_exptl_crystal_size_max          0.922
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.357
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.2413 11.0047 3.9370 0.2326 0.9726 0.0021
7.2831 -6.2652 -3.6740 -0.0012 -0.0113 -0.9999
-7.3011 6.2197 3.6578 0.0003 0.0073 1.0000
-0.5392 2.6731 -12.4618 -0.9427 0.3329 0.0208
-4.3652 -10.7474 -5.2467 -0.3330 -0.9429 0.0060
0.5053 -2.6458 12.4793 0.9428 -0.3330 -0.0162
4.2673 10.8292 5.2953 0.3330 0.9429 0.0073
3.6154 10.5566 -1.7400 -0.1831 0.9831 -0.0091
-3.6530 -10.5244 1.7587 0.1831 -0.9830 0.0143
1.8246 7.5984 -8.2252 -0.6501 0.7598 0.0001
-2.5271 -3.1606 -13.4787 -0.9831 -0.1831 0.0043
-3.9371 -8.0651 -10.8323 -0.7598 -0.6501 0.0002
3.9530 8.0518 10.8243 0.7598 0.6501 -0.0024
-1.6157 -7.7703 8.1175 0.6498 -0.7596 -0.0286
2.7140 3.0009 13.3792 0.9827 0.1830 -0.0300
-4.2343 -11.0035 -2.5020 -0.1296 -0.9915 0.0120
-2.5161 -10.0636 4.2514 0.3827 -0.9220 -0.0589
4.5626 9.1762 8.7092 0.6075 0.7930 -0.0461

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.801
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12848
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.133
_diffrn_reflns_theta_min         3.372
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.801
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  77.00   0.50    0.60    --    3.31-161.00 -24.00   66
  2  ω     10.00  51.00   0.50    0.60    --    3.31-118.00 165.29   82
  3  ω    -12.00  67.00   0.50    0.60    --    3.31  77.00-180.00  158
  4  ω     24.00  51.00   0.50    0.60    --    3.31-117.00 132.08   54
  5  ω     21.00  46.00   0.50    0.60    --    3.31-109.00-140.79   50
  6  ω     13.00  39.00   0.50    0.60    --    3.31 -99.00  90.00   52
  7  ω    -13.00  41.00   0.50    0.60    --    3.31-102.00 -96.95  108
  8  ω     29.00  54.00   0.50    0.60    --    3.31-123.00  40.87   50
  9  ω    -67.00  15.00   0.50    0.60    --    3.31 -57.00-150.00  164
 10  ω    -70.00  36.00   0.50    0.60    --    3.31 -19.00   0.00  212
 11  ω    -39.00  43.00   0.50    0.60    --   -3.63  19.00   0.00  164
 12  ω    -59.00  29.00   0.50    0.60    --   -3.63 -19.00-150.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0241124000
_diffrn_orient_matrix_UB_12      -0.0137901000
_diffrn_orient_matrix_UB_13      0.0716489000
_diffrn_orient_matrix_UB_21      0.0539317000
_diffrn_orient_matrix_UB_22      0.0724250000
_diffrn_orient_matrix_UB_23      -0.0135098000
_diffrn_orient_matrix_UB_31      -0.1014538000
_diffrn_orient_matrix_UB_32      0.0355908000
_diffrn_orient_matrix_UB_33      0.0103564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2448
_reflns_number_total             2691
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.056
_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)+(0.0227P)²+0.0474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0578
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.22536(2) 0.19427(2) 0.67166(2) 0.02943(7) Uani 1 1 d . . . . .
F2 F 0.1678(2) 0.47419(18) 0.3993(2) 0.0354(4) Uani 1 1 d . . . . .
F3 F 0.4204(3) 0.57572(18) 0.1717(2) 0.0380(4) Uani 1 1 d . . . . .
F4 F 0.8161(3) 0.43829(19) 0.14938(19) 0.0369(4) Uani 1 1 d . . . . .
F5 F 0.9466(2) 0.18850(19) 0.3515(2) 0.0350(4) Uani 1 1 d . . . . .
F6 F 0.6869(2) 0.07684(18) 0.57625(18) 0.0321(4) Uani 1 1 d . . . . .
C1 C 0.4221(4) 0.2737(3) 0.4956(3) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.3593(4) 0.4010(3) 0.3900(3) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.4888(4) 0.4550(3) 0.2742(3) 0.0270(6) Uani 1 1 d . . . . .
C4 C 0.6876(4) 0.3853(3) 0.2611(3) 0.0271(6) Uani 1 1 d . . . . .
C5 C 0.7531(4) 0.2570(3) 0.3651(3) 0.0256(5) Uani 1 1 d . . . . .
C6 C 0.6203(4) 0.2029(3) 0.4788(3) 0.0236(5) Uani 1 1 d . . . . .
C7 C 0.0392(4) -0.1561(3) 0.0222(3) 0.0264(5) Uani 1 1 d . . . . .
H7 H 0.075(4) -0.264(4) 0.035(3) 0.027(7) Uiso 1 1 d . . . . .
C8 C 0.1841(4) -0.0655(3) 0.0730(3) 0.0262(6) Uani 1 1 d . . . . .
H8 H 0.306(5) -0.104(3) 0.121(4) 0.029(8) Uiso 1 1 d . . . . .
C9 C 0.1485(4) 0.0914(3) 0.0530(3) 0.0248(5) Uani 1 1 d . . . . .
C10 C 0.3067(4) 0.1898(3) 0.1082(3) 0.0313(6) Uani 1 1 d . . . . .
H10A H 0.2581 0.2977 0.0793 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.4555 0.1808 0.0713 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.3093 0.1547 0.2098 0.047 Uiso 1 1 calc GR . . . .


_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
I1 C1 2.081(3) . ?
F2 C2 1.342(3) . ?
F3 C3 1.345(3) . ?
F4 C4 1.336(3) . ?
F5 C5 1.341(3) . ?
F6 C6 1.345(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.383(3) . ?
C2 C3 1.371(4) . ?
C3 C4 1.373(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.367(4) . ?
C7 H7 0.97(3) . ?
C7 C8 1.385(4) . ?
C7 C9 1.401(4) 2 ?
C8 H8 0.90(3) . ?
C8 C9 1.386(4) . ?
C9 C7 1.401(4) 2 ?
C9 C10 1.508(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 121.03(18) . . ?
C6 C1 I1 121.72(19) . . ?
C6 C1 C2 117.2(2) . . ?
F2 C2 C1 120.2(2) . . ?
F2 C2 C3 118.3(2) . . ?
C3 C2 C1 121.4(2) . . ?
F3 C3 C2 120.1(2) . . ?
F3 C3 C4 119.5(3) . . ?
C2 C3 C4 120.4(2) . . ?
F4 C4 C3 120.8(2) . . ?
F4 C4 C5 120.1(2) . . ?
C3 C4 C5 119.1(3) . . ?
F5 C5 C4 119.0(2) . . ?
F5 C5 C6 121.3(2) . . ?
C6 C5 C4 119.8(2) . . ?
F6 C6 C1 119.8(2) . . ?
F6 C6 C5 118.2(2) . . ?
C5 C6 C1 122.0(2) . . ?
C8 C7 H7 118.7(17) . . ?
C8 C7 C9 120.9(2) . 2 ?
C9 C7 H7 120.3(17) 2 . ?
C7 C8 H8 122(2) . . ?
C7 C8 C9 121.7(2) . . ?
C9 C8 H8 116(2) . . ?
C7 C9 C10 121.0(2) 2 . ?
C8 C9 C7 117.4(2) . 2 ?
C8 C9 C10 121.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 F2 -0.8(3) . . . . ?
I1 C1 C2 C3 179.4(2) . . . . ?
I1 C1 C6 F6 1.8(3) . . . . ?
I1 C1 C6 C5 -178.2(2) . . . . ?
F2 C2 C3 F3 -1.8(4) . . . . ?
F2 C2 C3 C4 179.0(2) . . . . ?
F3 C3 C4 F4 1.6(4) . . . . ?
F3 C3 C4 C5 -177.6(2) . . . . ?
F4 C4 C5 F5 0.3(4) . . . . ?
F4 C4 C5 C6 -179.6(2) . . . . ?
F5 C5 C6 F6 -1.1(4) . . . . ?
F5 C5 C6 C1 178.9(2) . . . . ?
C1 C2 C3 F3 178.0(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C1 C6 F6 -178.4(2) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
C2 C3 C4 F4 -179.2(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 F5 179.5(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 F6 178.8(2) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C6 C1 C2 F2 179.4(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C8 C9 C7 -0.8(5) . . . 2 ?
C7 C8 C9 C10 -179.9(3) . . . . ?
C9 C7 C8 C9 0.8(5) 2 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.958
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3040
_database_code_depnum_ccdc_archive 'CCDC 2483314'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2022-09-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-Xylene:1,4-dibromotetrafluorobenzene
_chemical_formula_moiety         'Br2 C6 F4, C8 H10'
_chemical_formula_sum            'C14 H10 Br2 F4'
_chemical_formula_weight         414.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 C6 F4 Br2 '
_chemical_oxdiff_usercomment     C6F4Br2+p-xylene
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'
Br Br -0.6763 1.2805 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.4576(3)
_cell_length_b                   8.3594(3)
_cell_length_c                   9.8748(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.357(3)
_cell_angle_gamma                90
_cell_volume                     697.56(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.2550
_cell_measurement_theta_min      4.4310
_shelx_estimated_absorpt_T_max   0.461
_shelx_estimated_absorpt_T_min   0.370
_exptl_absorpt_coefficient_mu    7.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50007
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 -3 0.0603
-3 5 0 0.0691
2 4 4 0.0820
2 -5 -2 0.0756
5 -1 -3 0.0522
-2 4 -4 0.0577
-2 -5 2 0.0564
-5 -2 1 0.0897
-5 3 -1 0.0708
-1 5 -2 0.0641
5 1 0 0.0678
4 -3 1 0.0610
-2 -4 -3 0.0771
3 -4 0 0.0608
4 -2 4 0.0623
2 0 6 0.0660
1 2 6 0.0690
-2 4 4 0.0797
0 -3 -6 0.0775
-2 -1 -6 0.0737
-1 0 6 0.0706
-4 3 3 0.0865
3 -2 -5 0.0682
1 0 -6 0.0639
-1 1 -6 0.0675
0 -3 5 0.0478
3 2 -5 0.0739
3 5 1 0.0844
-4 -4 -2 0.0679
-2 -5 -1 0.0664
1 5 1 0.0770

_exptl_crystal_preparation       '1:1 molar mixture (0.01 moles)'
_exptl_crystal_recrystallization_method 
'Grown from the melt in the bottle left in the fridge'
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.119
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.4912 0.0053 -3.4681 -0.5504 -0.4098 -0.7274
-2.9365 4.5851 0.3255 0.2991 0.2195 -0.9286
2.2865 3.6342 3.8240 0.8033 0.5955 0.0108
1.6616 -5.0195 -1.5567 -0.5180 -0.3822 0.7652
5.0152 -0.8675 -2.6433 0.4552 -0.5532 0.6977
-1.5690 4.0908 -3.7138 0.3674 -0.4425 -0.8181
-1.5942 -5.0136 1.6567 -0.8830 0.1940 0.4275
-5.2604 -1.5344 0.5035 -0.8342 0.1852 -0.5195
-4.7835 2.5121 -0.8342 -0.2172 0.0499 -0.9748
-1.4028 5.0365 -1.6665 0.5320 -0.1157 -0.8388
5.2961 1.4147 -0.4639 0.8218 -0.1825 0.5397
4.3042 -3.0639 1.4581 0.0867 0.0468 0.9951
-2.4458 -3.9999 -3.1310 -0.8694 -0.4930 0.0335
3.2897 -4.3289 0.3175 -0.2176 -0.1257 0.9679
3.8952 -2.1199 3.5722 0.1835 0.3989 0.8984
2.3344 0.4284 5.6622 0.3694 0.8101 0.4553
0.8649 1.9652 5.8422 0.4127 0.9073 0.0803
-1.9639 3.8567 3.9775 0.3332 0.7359 -0.5894
-0.1431 -2.5743 -5.6289 -0.4117 -0.9062 0.0968
-1.9865 -0.8347 -5.7929 -0.3861 -0.8474 -0.3644
-0.9141 0.0638 6.3589 -0.0616 0.9950 0.0787
-3.9753 2.9379 2.9366 -0.0397 0.6120 -0.7899
2.9334 -1.8526 -5.0965 0.0563 -0.8919 0.4487
1.0961 -0.2166 -6.3235 0.0619 -0.9975 -0.0348
-0.9326 1.4137 -6.0419 0.0528 -0.8681 -0.4936
-0.3421 -3.4426 4.9489 -0.4949 0.6944 0.5224
2.5773 2.1746 -5.1607 0.5796 -0.8113 -0.0757
2.5555 4.6065 1.4652 0.9577 0.2483 -0.1452
-3.6998 -3.6384 -1.7973 -0.9589 -0.2492 -0.1356
-1.9127 -4.9530 -1.2576 -0.9292 -0.2407 0.2804
0.9803 5.2714 0.9368 0.8619 0.2228 -0.4555

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4773
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         4.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  33.00   1.00    1.00    --   42.00  83.00 -72.84   25
  2  ω    -70.00   9.00   1.00    1.00    --  -42.37  57.00-120.00   79
  3  ω   -115.00 -88.00   1.00    1.00    --  -42.37 -57.00 150.00   27
  4  ω    -56.00 -14.00   1.00    1.00    --  -42.37 -57.00 150.00   42
  5  ω     18.00  44.00   1.00    1.00    --   42.37  38.00 -90.00   26
  6  ω      8.00  33.00   1.00    1.00    --   42.37  83.00  80.31   25
  7  ω     75.00 115.00   1.00    1.00    --   42.37  38.00 -90.00   40
  8  ω     29.00  93.00   1.00    1.00    --   42.37-125.00  60.00   64
  9  ω     16.00  41.00   1.00    1.00    --   50.00  82.00  94.15   25
 10  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 -31.70   25
 11  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-123.30   25
 12  ω     16.00  41.00   1.00    1.00    --   50.00  82.00  19.35   25
 13  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 169.56   25
 14  ω     35.00  70.00   1.00    1.00    --   54.00  65.00 -48.84   35
 15  ω     99.00 126.00   1.00    1.00    --   54.00  65.00 -48.84   27
 16  ω     76.00 106.00   1.00    1.00    --   58.00  71.00  64.05   30
 17  ω     28.00  53.00   1.00    1.00    --   58.00  71.00  64.05   25
 18  ω     30.00  68.00   1.00    1.00    --   58.00  67.00 -98.07   38
 19  ω     35.00  69.00   1.00    1.00    --   62.00  71.00-172.82   34
 20  ω     36.00  64.00   1.00    1.00    --   62.00  58.00  38.78   28
 21  ω     98.00 130.00   1.00    1.00    --   62.00  71.00-172.82   32
 22  ω     44.00  70.00   1.00    1.00    --   70.00  70.00 122.05   26
 23  ω    113.00 139.00   1.00    1.00    --   70.00  70.00 122.05   26
 24  ω     44.00  73.00   1.00    1.25    --   74.00  67.00 110.47   29
 25  ω    103.00 140.00   1.00    1.25    --   74.00  69.00  63.21   37
 26  ω     45.00  91.00   1.00    1.25    --   74.00  69.00  63.21   46
 27  ω     49.00  86.00   1.00    1.25    --   78.00  71.00 -39.15   37
 28  ω     56.00  87.00   1.00    1.25    --   82.00  58.00 172.47   31
 29  ω     56.00  81.00   1.00    1.25    --   86.00  70.00 129.57   25
 30  ω     61.00 162.00   1.00    1.25    --   90.00  66.00-108.95  101
 31  ω     69.00  96.00   1.00    1.25    --   94.00  54.00 179.20   27
 32  ω    111.00 173.00   1.00    1.25    --  103.86  77.00-150.00   62
 33  ω     32.00 101.00   1.00    1.25    --  103.86-125.00  30.00   69
 34  ω     35.00 130.00   1.00    1.25    --  103.86 -61.00  90.00   95
 35  ω     76.00 169.00   1.00    1.25    --  103.86  61.00   0.00   93
 36  ω    125.00 176.00   1.00    1.25    --  103.86  61.00 -60.00   51
 37  ω     79.00 120.00   1.00    1.25    --  103.86  61.00 -60.00   41
 38  ω     27.00 104.00   1.00    1.25    --  103.86 -95.00  60.00   77
 39  ω     31.00 112.00   1.00    1.25    --  103.86-125.00 -60.00   81
 40  ω     82.00 109.00   1.00    1.25    --  103.86  61.00  30.00   27
 41  ω     78.00 109.00   1.00    1.25    --  103.86  61.00 -30.00   31
 42  ω     77.00 173.00   1.00    1.25    --  103.86  50.00  91.28   96
 43  ω    126.00 160.00   1.00    1.25    --  103.86 125.00  60.00   34
 44  ω     76.00 175.00   1.00    1.25    --  103.86  61.00 150.00   99
 45  ω     75.00 102.00   1.00    1.25    --  103.86  61.00-180.00   27
 46  ω     76.00 103.00   1.00    1.25    --  103.86  61.00 -90.00   27
 47  ω     75.00 124.00   1.00    1.25    --  103.86  61.00-150.00   49
 48  ω    103.00 133.00   1.00    1.25    --  103.86  61.00  60.00   30
 49  ω     77.00 102.00   1.00    1.25    --  103.86  61.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1181618000
_diffrn_orient_matrix_UB_12      0.1404863000
_diffrn_orient_matrix_UB_13      0.0058897000
_diffrn_orient_matrix_UB_21      -0.0264709000
_diffrn_orient_matrix_UB_22      0.0200976000
_diffrn_orient_matrix_UB_23      0.1524645000
_diffrn_orient_matrix_UB_31      0.1362399000
_diffrn_orient_matrix_UB_32      -0.1176314000
_diffrn_orient_matrix_UB_33      0.0331412000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                713
_reflns_number_total             738
_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    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0206
_refine_ls_restrained_S_all      1.128
_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)+(0.0275P)²+0.7840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.27618(3) 0.0000 0.22166(3) 0.03288(14) Uani 1 2 d S T P . .
F1 F -0.11213(14) -0.28247(14) 0.09112(12) 0.0314(3) Uani 1 1 d . . . . .
C1 C -0.1183(3) 0.0000 0.0948(3) 0.0224(6) Uani 1 2 d S T P . .
C2 C -0.0582(2) -0.1419(2) 0.04672(19) 0.0224(4) Uani 1 1 d . . . . .
C3 C 0.0683(2) 0.3573(3) 0.54160(19) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.1142 0.2584 0.5696 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1388(3) 0.5000 0.5845(3) 0.0245(6) Uani 1 2 d S T P . .
C5 C 0.2886(4) 0.5000 0.6727(3) 0.0322(7) Uani 1 2 d S T P . .
H5A H 0.2695 0.4453 0.7582 0.048 Uiso 0.5 1 calc R U P A -1
H5B H 0.3215 0.6105 0.6913 0.048 Uiso 0.5 1 calc R U P A -1
H5C H 0.3723 0.4442 0.6257 0.048 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.868(3) . ?
F1 C2 1.340(2) . ?
C1 C2 1.382(2) . ?
C1 C2 1.382(2) 6 ?
C2 C2 1.377(4) 2 ?
C3 C3 1.389(4) 2_556 ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C3 1.392(3) 6_565 ?
C4 C5 1.508(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 120.88(13) . . ?
C2 C1 Br1 120.88(13) 6 . ?
C2 C1 C2 118.2(3) 6 . ?
F1 C2 C1 120.33(18) . . ?
F1 C2 C2 118.79(10) . 2 ?
C2 C2 C1 120.88(13) 2 . ?
C3 C3 H3 119.5 2_556 . ?
C3 C3 C4 121.02(13) 2_556 . ?
C4 C3 H3 119.5 . . ?
C3 C4 C3 118.0(3) 6_565 . ?
C3 C4 C5 121.02(13) 6_565 . ?
C3 C4 C5 121.02(13) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F1 -0.3(3) . . . . ?
Br1 C1 C2 C2 -179.96(19) . . . 2 ?
C2 C1 C2 F1 179.54(14) 6 . . . ?
C2 C1 C2 C2 -0.2(4) 6 . . 2 ?
C3 C3 C4 C3 0.1(4) 2_556 . . 6_565 ?
C3 C3 C4 C5 -178.9(3) 2_556 . . . ?

_olex2_date_sample_data_collection 2022-02-07
_olex2_exptl_crystal_mounting_method '0.3mm Hampton research nylon loop'
_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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.491
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1138
_database_code_depnum_ccdc_archive 'CCDC 2483317'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2025-08-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-Tetrafluorodiidobenzene
_chemical_formula_moiety         'C6 F4 I2, C6 H6'
_chemical_formula_sum            'C12 H6 F4 I2'
_chemical_formula_weight         479.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H6C6F4I2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.6866(2)
_cell_length_b                   7.1907(2)
_cell_length_c                   10.5364(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.058(3)
_cell_angle_gamma                90
_cell_volume                     658.13(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4321
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.0490
_cell_measurement_theta_min      3.6680
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.319
_exptl_absorpt_coefficient_mu    4.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -8 3 0.1085
-6 -9 0 0.1000
8 8 0 0.0830
-6 9 -3 0.0904
0 0 -1 0.0288
0 0 1 0.0288

_exptl_crystal_preparation       
'0.5g of C6F4I2 dissolved in 0.75g of hot benzene a'
_exptl_crystal_recrystallization_method 
'Bottle stood in hot water and allowed to cool at room temperature'
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.6874 -7.5382 3.4217 -0.1510 -0.6372 -0.7558
-6.4910 -8.5916 0.1608 -0.2141 -0.8922 0.3977
8.2100 7.5105 0.4811 0.1941 0.8075 -0.5570
-6.0172 8.5514 -3.2189 0.1787 0.7523 0.6342
0.0000 0.0000 -1.0000 -0.0620 0.0220 0.0144
-0.0000 -0.0000 1.0000 0.0620 -0.0220 -0.0144

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6531
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.454
_diffrn_reflns_theta_min         3.678
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  20.00   0.50    2.50    --   -2.48  77.00  90.00   84
  2  ω    -56.00  14.00   0.50    2.50    --    2.48 -28.00 -76.80  140
  3  ω    -48.00  16.00   0.50    2.50    --    2.48 -26.00  43.89  128
  4  ω    -53.00  20.00   0.50    2.50    --    2.48 -23.00 -21.23  146
  5  ω      9.00  35.00   0.50    2.50    --    2.48 -99.00 -90.00   52
  6  ω    -16.00  36.00   0.50    2.50    --    2.48 -16.00 129.02  104
  7  ω      6.00  35.00   0.50    2.50    --    2.48 -99.00  90.00   58
  8  ω    -43.00  25.00   0.50    2.50    --    2.48 -19.00-150.00  136
  9  ω      9.00  34.00   0.50    2.50    --    2.48 -99.00  30.00   50
 10  ω    -24.00  42.00   0.50    2.50    --    2.48 -14.00  74.30  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124382072
_diffrn_orient_matrix_UB_12      0.0354734910
_diffrn_orient_matrix_UB_13      0.0619657024
_diffrn_orient_matrix_UB_21      0.0162720960
_diffrn_orient_matrix_UB_22      0.0911362681
_diffrn_orient_matrix_UB_23      -0.0220036621
_diffrn_orient_matrix_UB_31      -0.0790244242
_diffrn_orient_matrix_UB_32      0.0131388547
_diffrn_orient_matrix_UB_33      -0.0143846379
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                901
_reflns_number_total             969
_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 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.114a 64-bit (release 13-06-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.458
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.070
_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)+(0.0490P)²+0.2854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.32314(3) 0.0000 -0.19606(2) 0.03275(14) Uani 1 2 d S T P A 1
F2 F 0.2845(3) 0.0000 0.1063(3) 0.0427(7) Uani 1 2 d S T P A 1
F3 F 0.0374(3) 0.0000 0.2556(3) 0.0382(6) Uani 1 2 d S T P A 1
C1 C 0.1309(5) 0.0000 -0.0789(4) 0.0260(7) Uani 1 2 d S T P A 1
C2 C 0.1444(5) 0.0000 0.0518(4) 0.0282(8) Uani 1 2 d S T P A 1
C3 C 0.0161(5) 0.0000 0.1296(4) 0.0280(8) Uani 1 2 d S T P A 1
C4 C 0.0000 0.3105(7) 0.5000 0.0548(15) Uani 1 2 d S T P B 2
H4 H 0.0000 0.1784 0.5000 0.066 Uiso 1 2 calc R U P B 2
C5 C 0.1026(4) 0.4051(6) 0.5750(3) 0.0507(10) Uani 1 1 d . . . B 2
H5 H 0.1735 0.3388 0.6267 0.061 Uiso 1 1 calc R U . B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.077(4) . ?
F2 C2 1.345(5) . ?
F3 C3 1.341(5) . ?
C1 C2 1.382(6) . ?
C1 C3 1.384(6) 5 ?
C2 C3 1.384(6) . ?
C3 C1 1.384(6) 5 ?
C4 H4 0.9500 . ?
C4 C5 1.371(5) . ?
C4 C5 1.371(5) 2_556 ?
C5 C5 1.364(9) 6_565 ?
C5 H5 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
C2 C1 I1 121.6(3) . . ?
C2 C1 C3 117.5(4) . 5 ?
C3 C1 I1 120.9(3) 5 . ?
F2 C2 C1 120.1(4) . . ?
F2 C2 C3 118.4(4) . . ?
C1 C2 C3 121.5(4) . . ?
F3 C3 C1 120.5(4) . 5 ?
F3 C3 C2 118.4(4) . . ?
C1 C3 C2 121.0(4) 5 . ?
C5 C4 H4 119.7 . . ?
C5 C4 H4 119.7 2_556 . ?
C5 C4 C5 120.5(5) 2_556 . ?
C4 C5 H5 120.1 . . ?
C5 C5 C4 119.7(2) 6_565 . ?
C5 C5 H5 120.1 6_565 . ?

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
I1 C1 C2 F2 0.000(0) . . . . ?
I1 C1 C2 C3 180.000(0) . . . . ?
F2 C2 C3 F3 0.000(0) . . . . ?
F2 C2 C3 C1 180.000(0) . . . 5 ?
C1 C2 C3 F3 180.000(0) . . . . ?
C1 C2 C3 C1 0.000(0) . . . 5 ?
C3 C1 C2 F2 180.000(0) 5 . . . ?
C3 C1 C2 C3 0.000(0) 5 . . . ?
C5 C4 C5 C5 0.001(1) 2_556 . . 6_565 ?

_olex2_exptl_crystal_mounting_method '0.3mm loop from Hampton Research'
_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 1.914
_oxdiff_exptl_absorpt_empirical_full_min 0.637
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2922
_database_code_depnum_ccdc_archive 'CCDC 2483309'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:chloropentafluorobenzene
_chemical_formula_moiety         'C6 Cl F5, C8 H10'
_chemical_formula_sum            'C14 H10 Cl F5'
_chemical_formula_weight         308.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 F5 Cl C8 H10'
_chemical_oxdiff_usercomment     '0.3mm capillary'
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'
Cl Cl 0.3639 0.7018 '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                   6.1383(5)
_cell_length_b                   7.4411(7)
_cell_length_c                   7.9224(6)
_cell_angle_alpha                111.378(8)
_cell_angle_beta                 99.662(7)
_cell_angle_gamma                95.159(7)
_cell_volume                     327.65(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2170
_cell_measurement_temperature    120
_cell_measurement_theta_max      72.6160
_cell_measurement_theta_min      6.1170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             156
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 1 -3 0.0328
-3 -1 3 0.0706
1 -5 1 0.1936
2 3 1 0.1075
1 3 -5 0.0308
1 1 -5 0.0262
-1 3 2 0.0884
-1 -1 5 0.0820
4 1 -2 0.0443
-3 2 2 0.0818
-1 1 -4 0.0527
-1 0 -4 0.0525

_exptl_crystal_recrystallization_method 
'Crystallized in situ in 0.3mm X-ray capillary'
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.105
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.3866 0.8148 -3.3940 0.9103 -0.4138 0.0095
-3.3405 -1.0351 3.4490 -0.9089 0.4133 -0.0559
1.0552 -4.7215 1.1173 0.0485 -0.0185 -0.9987
1.5740 3.0489 1.2880 -0.1313 -0.7762 0.6167
0.7105 2.5424 -5.0529 0.8607 0.2904 0.4181
1.2032 0.5645 -4.9496 0.9480 0.3182 -0.0085
-1.4569 3.2624 2.1875 -0.6102 -0.2023 0.7660
-1.2032 -0.5645 4.9496 -0.9480 -0.3182 0.0085
3.8609 0.7226 -1.6180 0.6633 -0.7483 0.0093
-3.3698 1.8898 2.1182 -0.7649 0.3620 0.5328
-1.4162 0.6694 -4.2443 0.5484 0.8299 0.1026
-1.3136 0.0763 -4.1016 0.5509 0.8343 -0.0220

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.561
_diffrn_reflns_theta_min         6.144
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  28.00   1.00    1.00    --   38.00  85.00 -88.50   25
  2  ω   -103.00 -76.00   1.00    1.00    --  -40.87 -38.00-120.00   27
  3  ω    -43.00 -18.00   1.00    1.00    --  -40.87 -38.00-120.00   25
  4  ω    -87.00 -14.00   1.00    1.00    --  -40.87 125.00  30.00   73
  5  ω    -81.00 -48.00   1.00    1.00    --  -40.87 -38.00  30.00   33
  6  ω    -84.00 -10.00   1.00    1.00    --  -40.87 125.00-150.00   74
  7  ω    -41.00 -16.00   1.00    1.00    --  -40.87 -38.00  30.00   25
  8  ω     14.00  39.00   1.00    1.00    --   46.00  76.00 117.96   25
  9  ω     15.00  40.00   1.00    1.00    --   46.00  79.00 -59.03   25
 10  ω     13.00  40.00   1.00    1.00    --   46.00  78.00  71.30   27
 11  ω     16.00  41.00   1.00    1.00    --   50.00  81.00 156.44   25
 12  ω     16.00  41.00   1.00    1.00    --   50.00  82.00   2.50   25
 13  ω     28.00  60.00   1.00    1.00    --   54.00  54.00 120.47   32
 14  ω     99.00 127.00   1.00    1.00    --   54.00  69.00-176.46   28
 15  ω     79.00 115.00   1.00    1.00    --   54.00  68.00 -85.66   36
 16  ω     76.00 101.00   1.00    1.00    --   54.00  54.00 120.47   25
 17  ω     31.00  59.00   1.00    1.00    --   54.00  69.00-176.46   28
 18  ω     26.00  76.00   1.00    1.00    --   54.00  68.00 -85.66   50
 19  ω     31.00  78.00   1.00    1.00    --   62.00  70.00-143.17   47
 20  ω     42.00  69.00   1.00    1.00    --   62.00  60.00 117.98   27
 21  ω     91.00 118.00   1.00    1.00    --   62.00  60.00 117.98   27
 22  ω     38.00  97.00   1.00    1.00    --   66.00  55.00  41.86   59
 23  ω     95.00 141.00   1.00    1.00    --   70.00  67.00 133.64   46
 24  ω     40.00  89.00   1.00    1.00    --   70.00  67.00 133.64   49
 25  ω     98.00 143.00   1.00    1.00    --   70.00  68.00 -44.39   45
 26  ω     40.00  68.00   1.00    1.00    --   70.00  68.00 -44.39   28
 27  ω     54.00  90.00   1.00    1.00    --   74.00  62.00 -21.12   36
 28  ω     52.00  79.00   1.00    1.00    --   82.00  69.00-151.83   27
 29  ω     77.00 132.00   1.00    1.00    --  106.06 -77.00 -30.00   55
 30  ω     33.00  60.00   1.00    1.00    --  106.06 -77.00 -30.00   27
 31  ω     77.00 107.00   1.00    1.00    --  106.06  61.00  30.00   30
 32  ω     79.00 122.00   1.00    1.00    --  106.06  61.00 -60.00   43
 33  ω     80.00 177.00   1.00    1.00    --  106.06  61.00 150.00   97
 34  ω     80.00 107.00   1.00    1.00    --  106.06  45.00 -60.00   27
 35  ω     77.00 176.00   1.00    1.00    --  106.06  61.00-120.00   99
 36  ω    137.00 178.00   1.00    1.00    --  106.06  61.00  90.00   41
 37  ω    122.00 168.00   1.00    1.00    --  106.06  77.00-180.00   46
 38  ω     99.00 163.00   1.00    1.00    --  106.06 125.00 -60.00   64
 39  ω     31.00 136.00   1.00    1.00    --  106.06 -77.00-120.00  105
 40  ω     84.00 117.00   1.00    1.00    --  106.06  61.00 -30.00   33
 41  ω    116.00 141.00   1.00    1.00    --  106.06  61.00-150.00   25
 42  ω     40.00 130.00   1.00    1.00    --  106.06-149.00-165.00   90
 43  ω     82.00 113.00   1.00    1.00    --  106.06  61.00-150.00   31
 44  ω    112.00 177.00   1.00    1.00    --  106.06  61.00  60.00   65
 45  ω    111.00 177.00   1.00    1.00    --  106.06  55.00   0.57   66
 46  ω     78.00 114.00   1.00    1.00    --  106.06  61.00  90.00   36
 47  ω     80.00 111.00   1.00    1.00    --  106.06  61.00  60.00   31
 48  ω     78.00 110.00   1.00    1.00    --  106.06  55.00   0.57   32
 49  ω     81.00 117.00   1.00    1.00    --  106.06  61.00 120.00   36
 50  ω     61.00 111.00   1.00    1.00    --  106.06-125.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1060434000
_diffrn_orient_matrix_UB_12      -0.0265104000
_diffrn_orient_matrix_UB_13      -0.1687705000
_diffrn_orient_matrix_UB_21      -0.2335239000
_diffrn_orient_matrix_UB_22      -0.0790590000
_diffrn_orient_matrix_UB_23      -0.1300813000
_diffrn_orient_matrix_UB_31      -0.0290067000
_diffrn_orient_matrix_UB_32      0.2094163000
_diffrn_orient_matrix_UB_33      0.0185401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1085
_reflns_number_total             1281
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.054
_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)+(0.0910P)²+0.1738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1588
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Cl1, F1}
3. Restrained distances
 C1-C2 \\sim C2-C3
 with sigma of 0.01
 C2-F2 \\sim C3-F3
 with sigma of 0.01
4. Restrained planarity
 Cl1, F2, F3, C1, C2, C3
 with sigma of 0.05
5. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(F1)
6. Others
 Fixed Sof: Cl1(0.5) F1(0.5)
7.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20087(15) 0.10012(14) 0.39441(12) 0.0445(3) Uani 0.5 1 d . . P A 1
F1 F 0.20087(15) 0.10012(14) 0.39441(12) 0.0445(3) Uani 0.5 1 d . . P A 1
F2 F 0.4341(2) 0.1778(2) 0.1417(2) 0.0451(5) Uani 1 1 d D . . A 1
F3 F 0.2533(2) 0.0838(2) -0.2204(2) 0.0445(5) Uani 1 1 d D . . A 1
C1 C 0.0941(4) 0.0474(3) 0.1860(3) 0.0350(6) Uani 1 1 d D . . A 1
C2 C 0.2197(4) 0.0891(3) 0.0720(3) 0.0356(6) Uani 1 1 d D . . A 1
C3 C 0.1278(4) 0.0420(3) -0.1122(3) 0.0352(6) Uani 1 1 d D . . A 1
C5 C 0.1131(4) 0.5224(4) -0.1288(4) 0.0376(6) Uani 1 1 d . . . B 2
H5 H 0.193(6) 0.531(5) -0.222(5) 0.060(10) Uiso 1 1 d . . . C 2
C6 C 0.2240(4) 0.5768(4) 0.0532(4) 0.0365(6) Uani 1 1 d . . . B 2
H6 H 0.383(6) 0.641(5) 0.099(5) 0.056(9) Uiso 1 1 d . . . D 2
C7 C 0.1144(4) 0.5555(4) 0.1860(3) 0.0364(6) Uani 1 1 d . . . B 2
C8 C 0.2362(7) 0.6136(6) 0.3848(4) 0.0642(10) Uani 1 1 d . . . B 2
H8A H 0.2991 0.5023 0.3993 0.096 Uiso 1 1 calc R U . B 2
H8B H 0.1312 0.6529 0.4670 0.096 Uiso 1 1 calc R U . B 2
H8C H 0.3575 0.7234 0.4174 0.096 Uiso 1 1 calc R U . B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.558(3) . ?
F2 C2 1.344(3) . ?
F3 C3 1.340(3) . ?
C1 C2 1.379(3) . ?
C1 C3 1.388(3) 2 ?
C2 C3 1.373(4) . ?
C3 C1 1.388(3) 2 ?
C5 H5 0.97(4) . ?
C5 C6 1.379(4) . ?
C5 C7 1.394(4) 2_565 ?
C6 H6 0.99(4) . ?
C6 C7 1.387(4) . ?
C7 C5 1.394(4) 2_565 ?
C7 C8 1.509(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl1 120.2(2) . . ?
C2 C1 C3 119.0(2) . 2 ?
C3 C1 Cl1 120.8(2) 2 . ?
F2 C2 C1 119.8(2) . . ?
F2 C2 C3 119.5(2) . . ?
C3 C2 C1 120.7(2) . . ?
F3 C3 C1 120.1(2) . 2 ?
F3 C3 C2 119.6(2) . . ?
C2 C3 C1 120.3(2) . 2 ?
C6 C5 H5 121(2) . . ?
C6 C5 C7 121.0(2) . 2_565 ?
C7 C5 H5 118(2) 2_565 . ?
C5 C6 H6 122(2) . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 116(2) . . ?
C5 C7 C8 121.0(3) 2_565 . ?
C6 C7 C5 117.5(2) . 2_565 ?
C6 C7 C8 121.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 F2 -0.8(3) . . . . ?
Cl1 C1 C2 C3 179.50(19) . . . . ?
F2 C2 C3 F3 0.4(3) . . . . ?
F2 C2 C3 C1 -179.2(2) . . . 2 ?
C1 C2 C3 F3 -179.9(2) . . . . ?
C1 C2 C3 C1 0.5(4) . . . 2 ?
C3 C1 C2 F2 179.2(2) 2 . . . ?
C3 C1 C2 C3 -0.5(4) 2 . . . ?
C5 C6 C7 C5 -0.3(4) . . . 2_565 ?
C5 C6 C7 C8 179.5(3) . . . . ?
C7 C5 C6 C7 0.3(5) 2_565 . . . ?

_olex2_date_sample_data_collection 2021-09-30
_olex2_exptl_crystal_mounting_method 'Sealed capillary glued in a brass pip'
_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 12.023
_oxdiff_exptl_absorpt_empirical_full_min 0.280
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3187
_database_code_depnum_ccdc_archive 'CCDC 2483313'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:bromopentafluorobenzene
_chemical_formula_moiety         'Br C6 F5, C8 H10'
_chemical_formula_sum            'C14 H10 Br F5'
_chemical_formula_weight         353.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 C6 F5 Br'
_chemical_oxdiff_usercomment     
'0.3mm capillary 1:1 molar ratio grown at about 260K'
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'
Br Br -0.6763 1.2805 '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                   9.0813(3)
_cell_length_b                   15.2034(4)
_cell_length_c                   9.8653(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.229(3)
_cell_angle_gamma                90
_cell_volume                     1344.42(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13139
_cell_measurement_temperature    120
_cell_measurement_theta_max      72.1460
_cell_measurement_theta_min      4.9230
_shelx_estimated_absorpt_T_max   0.323
_shelx_estimated_absorpt_T_min   0.096
_exptl_absorpt_coefficient_mu    4.628
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -5 -3 0.4442
-5 5 3 0.4901
-3 0 -5 0.1721
3 0 5 0.1426
1 7 -5 0.2411
-1 -7 4 0.0803
3 8 -1 0.2478
-3 -8 1 0.0656
4 6 2 0.2247
-4 -6 -2 0.0951

_exptl_crystal_preparation       '1:1 molar ratio'
_exptl_crystal_recrystallization_method 
'Crystal grown in 0.3mm capillary in situ'
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.315
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.6375 -4.5994 -3.3693 -0.0052 -0.0023 1.0000
-4.6180 4.6010 3.4051 0.0122 0.0026 -0.9999
-2.7828 -0.2255 -5.0860 -0.9990 -0.0445 -0.0090
2.8358 0.1727 5.0468 0.9988 0.0445 0.0205
0.6453 7.0150 -4.5053 -0.5064 -0.8617 0.0317
-0.5506 -7.1120 4.4393 0.5067 0.8620 -0.0114
3.1302 8.3426 -0.8706 0.2680 -0.9624 0.0438
-3.1168 -8.3574 0.8608 -0.2680 0.9626 -0.0408
3.7370 6.3268 2.0771 0.7258 -0.6874 0.0272
-3.6488 -6.4180 -2.1419 -0.7260 0.6877 -0.0080

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22028
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.038
_diffrn_reflns_theta_min         5.395
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  20.00   1.00    1.00    --   34.00  94.00 127.45   25
  2  ω     -4.00  21.00   1.00    1.00    --   34.00  91.00-144.46   25
  3  ω   -116.00 -78.00   1.00    1.00    --  -42.37 -38.00  90.00   38
  4  ω    -53.00 -16.00   1.00    1.00    --  -42.37 -57.00   0.00   37
  5  ω   -108.00 -59.00   1.00    1.00    --  -42.37 -57.00   0.00   49
  6  ω    -62.00 -21.00   1.00    1.00    --  -42.37 -38.00  90.00   41
  7  ω    -71.00  31.00   1.00    1.00    --  -42.37  57.00 150.00  102
  8  ω     50.00 121.00   1.00    1.00    --   42.37  19.00-150.00   71
  9  ω     27.00  95.00   1.00    1.00    --   42.37-125.00 -30.00   68
 10  ω      3.00  47.00   1.00    1.00    --   42.37  19.00-150.00   44
 11  ω     12.00  39.00   1.00    1.00    --   46.00  81.00 134.49   27
 12  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-169.99   25
 13  ω     16.00  42.00   1.00    1.00    --   50.00  82.00-124.17   26
 14  ω     16.00  42.00   1.00    1.00    --   50.00  81.00 -27.24   26
 15  ω     16.00  41.00   1.00    1.00    --   50.00  82.00  49.70   25
 16  ω     31.00  72.00   1.00    1.00    --   62.00  71.00 -55.71   41
 17  ω    105.00 140.00   1.00    1.00    --   66.00  71.00   3.87   35
 18  ω     86.00 113.00   1.00    1.00    --   66.00  69.00 152.09   27
 19  ω     35.00  61.00   1.00    1.00    --   66.00  71.00   3.87   26
 20  ω     36.00  61.00   1.00    1.00    --   66.00  70.00-119.35   25
 21  ω     36.00  63.00   1.00    1.00    --   66.00  69.00 152.09   27
 22  ω    111.00 138.00   1.00    1.00    --   70.00  69.00 175.79   27
 23  ω     43.00  75.00   1.00    1.00    --   70.00  70.00-172.19   32
 24  ω    105.00 139.00   1.00    1.00    --   70.00  69.00  60.28   34
 25  ω     39.00  72.00   1.00    1.00    --   70.00  69.00  60.28   33
 26  ω     41.00  73.00   1.00    1.00    --   70.00  66.00 129.14   32
 27  ω     39.00  66.00   1.00    1.00    --   70.00  69.00 175.79   27
 28  ω     44.00  71.00   1.00    1.24    --   74.00  70.00 -97.60   27
 29  ω     44.00  72.00   1.00    1.24    --   74.00  70.00 -68.52   28
 30  ω     45.00  71.00   1.00    1.24    --   74.00  61.00 103.73   26
 31  ω     49.00  74.00   1.00    1.24    --   78.00  68.00  16.27   25
 32  ω     53.00  91.00   1.00    1.24    --   82.00  64.00  40.60   38
 33  ω     51.00  77.00   1.00    1.24    --   82.00  71.00-123.08   26
 34  ω    117.00 158.00   1.00    1.24    --   90.00  60.00-178.81   41
 35  ω     62.00  96.00   1.00    1.24    --   90.00  60.00-178.81   34
 36  ω    117.00 173.00   1.00    1.24    --  102.00  69.00 -60.24   56
 37  ω     72.00  97.00   1.00    1.24    --  102.00  69.00 -60.24   25
 38  ω     24.00 106.00   1.00    1.24    --  103.86 -95.00 -90.00   82
 39  ω     36.00 113.00   1.00    1.24    --  103.86-125.00 150.00   77
 40  ω     40.00  72.00   1.00    1.24    --  103.86 -61.00 120.00   32
 41  ω     75.00 141.00   1.00    1.24    --  103.86  61.00 150.00   66
 42  ω     75.00 174.00   1.00    1.24    --  103.86  61.00  90.00   99
 43  ω    115.00 177.00   1.00    1.24    --  103.86  65.00   1.92   62
 44  ω     75.00 100.00   1.00    1.24    --  103.86  65.00   1.92   25
 45  ω     80.00 117.00   1.00    1.24    --  103.86  45.00 150.00   37
 46  ω     82.00 173.00   1.00    1.24    --  103.86  68.00 171.29   91
 47  ω     75.00 175.00   1.00    1.24    --  103.86  61.00-150.00  100
 48  ω     76.00 176.00   1.00    1.24    --  103.86  61.00 -90.00  100
 49  ω     33.00 129.00   1.00    1.24    --  103.86 -45.00-120.00   96
 50  ω     77.00 143.00   1.00    1.24    --  103.86  61.00 -30.00   66
 51  ω     76.00 101.00   1.00    1.24    --  103.86  61.00 -65.90   25
 52  ω     75.00 105.00   1.00    1.24    --  103.86  61.00  30.00   30
 53  ω     76.00 103.00   1.00    1.24    --  103.86  63.00 109.57   27
 54  ω     75.00 152.00   1.00    1.24    --  103.86  61.00  60.00   77
 55  ω     39.00  88.00   1.00    1.24    --  103.86 -77.00  30.00   49
 56  ω    124.00 150.00   1.00    1.24    --  103.86  61.00-120.00   26
 57  ω     76.00 101.00   1.00    1.24    --  103.86  61.00-120.00   25
 58  ω     91.00 118.00   1.00    1.24    --  103.86 -61.00 120.00   27
 59  ω     32.00 112.00   1.00    1.24    --  103.86-125.00-120.00   80
 60  ω     57.00 103.00   1.00    1.24    --  103.86 -95.00   0.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1059621000
_diffrn_orient_matrix_UB_12      0.0067763000
_diffrn_orient_matrix_UB_13      0.1381370000
_diffrn_orient_matrix_UB_21      -0.0571378000
_diffrn_orient_matrix_UB_22      -0.0893365000
_diffrn_orient_matrix_UB_23      0.0439766000
_diffrn_orient_matrix_UB_31      0.1226755000
_diffrn_orient_matrix_UB_32      -0.0473852000
_diffrn_orient_matrix_UB_33      -0.0632558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2381
_reflns_number_total             2624
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.056
_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)+(0.0622P)²+0.5565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.43667(3) 0.49716(2) 0.80182(3) 0.03732(15) Uani 1 1 d . . . . .
F2 F 0.68447(15) 0.62781(10) 0.91475(14) 0.0375(3) Uani 1 1 d . . . . .
F3 F 0.67301(16) 0.80529(10) 0.91691(15) 0.0399(4) Uani 1 1 d . . . . .
F4 F 0.41922(17) 0.89005(10) 0.80706(14) 0.0401(4) Uani 1 1 d . . . . .
F5 F 0.17497(15) 0.79692(9) 0.69371(15) 0.0354(3) Uani 1 1 d . . . . .
F6 F 0.18351(14) 0.61968(9) 0.69419(14) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.4337(2) 0.62007(15) 0.80573(19) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.5573(2) 0.66864(16) 0.8613(2) 0.0286(5) Uani 1 1 d . . . . .
C3 C 0.5531(3) 0.75822(17) 0.8624(2) 0.0308(5) Uani 1 1 d . . . . .
C4 C 0.4240(2) 0.80265(15) 0.8063(2) 0.0291(5) Uani 1 1 d . . . . .
C5 C 0.2999(3) 0.75493(15) 0.7489(2) 0.0283(5) Uani 1 1 d . . . . .
C6 C 0.3059(2) 0.66463(16) 0.7494(2) 0.0268(4) Uani 1 1 d . . . . .
C7 C 0.7330(3) 0.63020(16) 0.5781(2) 0.0311(5) Uani 1 1 d . . . . .
C8 C 0.8274(3) 0.69851(18) 0.6294(3) 0.0339(5) Uani 1 1 d . . . . .
H8 H 0.925(3) 0.685(2) 0.677(3) 0.043(8) Uiso 1 1 d . . . . .
C9 C 0.7846(3) 0.78536(17) 0.6121(3) 0.0341(5) Uani 1 1 d . . . . .
H9 H 0.850(4) 0.829(2) 0.655(3) 0.048(8) Uiso 1 1 d . . . . .
C10 C 0.6452(3) 0.80804(16) 0.5418(2) 0.0324(5) Uani 1 1 d . . . . .
C11 C 0.5490(3) 0.74019(17) 0.4909(2) 0.0333(5) Uani 1 1 d . . . . .
H11 H 0.447(3) 0.7513(19) 0.439(3) 0.037(7) Uiso 1 1 d . . . . .
C12 C 0.5926(3) 0.65329(17) 0.5089(2) 0.0326(5) Uani 1 1 d . . . . .
H12 H 0.533(3) 0.605(2) 0.479(3) 0.038(7) Uiso 1 1 d . . . . .
C13 C 0.7817(3) 0.53577(19) 0.5961(3) 0.0464(6) Uani 1 1 d . . . . .
H13A H 0.7047 0.5018 0.6320 0.070 Uiso 1 1 calc R U . . .
H13B H 0.8754 0.5325 0.6608 0.070 Uiso 1 1 calc R U . . .
H13C H 0.7966 0.5115 0.5073 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5983(4) 0.90280(19) 0.5218(3) 0.0484(7) Uani 1 1 d . . . . .
H14A H 0.5391 0.9102 0.4303 0.073 Uiso 1 1 calc R U . . .
H14B H 0.6871 0.9403 0.5302 0.073 Uiso 1 1 calc R U . . .
H14C H 0.5381 0.9195 0.5917 0.073 Uiso 1 1 calc R U . . .


_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
Br1 C1 1.869(2) . ?
F2 C2 1.342(2) . ?
F3 C3 1.341(3) . ?
F4 C4 1.330(3) . ?
F5 C5 1.339(3) . ?
F6 C6 1.344(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.362(4) . ?
C3 C4 1.389(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.374(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.391(3) . ?
C7 C13 1.504(3) . ?
C8 H8 0.96(3) . ?
C8 C9 1.379(4) . ?
C9 H9 0.95(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.393(3) . ?
C10 C14 1.506(4) . ?
C11 H11 1.00(3) . ?
C11 C12 1.383(4) . ?
C12 H12 0.93(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 121.93(16) . . ?
C6 C1 Br1 119.74(16) . . ?
C6 C1 C2 118.3(2) . . ?
F2 C2 C1 120.1(2) . . ?
F2 C2 C3 118.9(2) . . ?
C3 C2 C1 121.0(2) . . ?
F3 C3 C2 121.0(2) . . ?
F3 C3 C4 118.6(2) . . ?
C2 C3 C4 120.4(2) . . ?
F4 C4 C3 120.7(2) . . ?
F4 C4 C5 120.1(2) . . ?
C5 C4 C3 119.2(2) . . ?
F5 C5 C4 119.9(2) . . ?
F5 C5 C6 120.5(2) . . ?
C6 C5 C4 119.6(2) . . ?
F6 C6 C1 120.0(2) . . ?
F6 C6 C5 118.50(19) . . ?
C5 C6 C1 121.5(2) . . ?
C8 C7 C12 117.0(2) . . ?
C8 C7 C13 121.2(2) . . ?
C12 C7 C13 121.8(2) . . ?
C7 C8 H8 119.4(18) . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 H8 118.9(18) . . ?
C8 C9 H9 118.5(19) . . ?
C8 C9 C10 121.1(2) . . ?
C10 C9 H9 120.3(19) . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 C14 121.3(2) . . ?
C11 C10 C14 120.9(2) . . ?
C10 C11 H11 122.4(16) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 116.8(17) . . ?
C7 C12 H12 113.7(18) . . ?
C11 C12 C7 121.7(2) . . ?
C11 C12 H12 124.6(18) . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F2 -0.1(3) . . . . ?
Br1 C1 C2 C3 179.63(17) . . . . ?
Br1 C1 C6 F6 1.1(3) . . . . ?
Br1 C1 C6 C5 -179.24(17) . . . . ?
F2 C2 C3 F3 -0.6(3) . . . . ?
F2 C2 C3 C4 179.1(2) . . . . ?
F3 C3 C4 F4 -0.2(3) . . . . ?
F3 C3 C4 C5 179.5(2) . . . . ?
F4 C4 C5 F5 0.2(3) . . . . ?
F4 C4 C5 C6 -179.64(19) . . . . ?
F5 C5 C6 F6 -0.4(3) . . . . ?
F5 C5 C6 C1 179.94(19) . . . . ?
C1 C2 C3 F3 179.7(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C6 F6 179.9(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C3 C4 F4 -179.9(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 F5 -179.6(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 F6 179.39(19) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C2 F2 -178.8(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C8 C9 C10 C14 -179.5(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C12 C7 C8 C9 -0.3(4) . . . . ?
C13 C7 C8 C9 179.3(2) . . . . ?
C13 C7 C12 C11 -179.2(2) . . . . ?
C14 C10 C11 C12 179.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 61.167
_oxdiff_exptl_absorpt_empirical_full_min 0.351
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_696
_database_code_depnum_ccdc_archive 'CCDC 2483312'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2024-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:p-dichlorotetrafluorobenzene
_chemical_formula_moiety         'C6 Cl2 F4, C8 H10'
_chemical_formula_sum            'C14 H10 Cl2 F4'
_chemical_formula_weight         325.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H10 F4 Cl2'
_chemical_oxdiff_usercomment     'Same capillary as for phase II'
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'
Cl Cl 0.3639 0.7018 '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                   6.3455(3)
_cell_length_b                   7.5012(3)
_cell_length_c                   7.7599(3)
_cell_angle_alpha                109.370(4)
_cell_angle_beta                 98.590(4)
_cell_angle_gamma                90.299(3)
_cell_volume                     343.95(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4654
_cell_measurement_temperature    130
_cell_measurement_theta_max      74.5670
_cell_measurement_theta_min      6.1070
_shelx_estimated_absorpt_T_max   0.445
_shelx_estimated_absorpt_T_min   0.108
_exptl_absorpt_coefficient_mu    4.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.143
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             164
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -5 0.1141
4 -1 -1 0.4276
-4 1 1 0.4228
-1 -4 3 0.0874
1 4 -3 0.1312
1 5 -1 0.1342
-1 -5 1 0.0876
-1 -4 -1 0.0905
1 4 1 0.1277
1 2 4 0.1191
-1 -2 -4 0.0982
0 -1 5 0.1047
0 1 -5 0.1113
0 -3 5 0.0950
0 3 -5 0.1207

_exptl_crystal_preparation       
'Components mixed in 50:50 molar ratio at 1/100 mole scale'
_exptl_crystal_recrystallization_method 
'Crystals grown in situ and coooled slowly through phase transitions'
_exptl_crystal_size_max          0.875
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.211
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.3386 2.9384 -4.7919 0.2324 0.9723 0.0242
3.9133 -1.2965 -1.0773 0.0054 0.0310 0.9995
-3.9091 1.3699 0.9610 0.0003 -0.0072 -1.0000
-0.6915 -4.4259 3.4296 0.2846 -0.9577 0.0417
0.7058 4.4215 -3.4334 -0.2846 0.9579 -0.0380
0.9777 4.6809 -1.1782 -0.7244 0.6863 -0.0656
-0.9441 -4.6900 1.1697 0.7239 -0.6859 0.0741
-0.9609 -3.6976 -1.3925 0.9692 -0.2319 0.0824
0.9571 3.6986 1.3933 -0.9692 0.2319 -0.0834
0.6425 1.7445 3.5975 -0.9548 -0.2836 -0.0887
-0.6133 -1.7537 -3.6018 0.9542 0.2834 0.0960
0.1835 -0.6866 4.8414 -0.6864 -0.7245 -0.0635
-0.1629 0.6790 -4.8446 0.6862 0.7242 0.0687
-0.3187 -2.9455 4.7878 -0.2325 -0.9724 -0.0191
0.4329 2.9014 -4.8104 0.2324 0.9714 0.0484

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.556
_diffrn_reflns_theta_min         6.124
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 107.00   0.50    3.00    --   50.30  41.00 -37.00   54
  2  ω     96.00 131.00   0.50    3.00    --  102.76  41.00 -37.00   70
  3  ω    135.00 162.00   0.50    3.00    --  102.76  41.00 -37.00   54
  4  ω     65.00 108.00   0.50    3.00    --  102.76 -41.00 169.00   86
  5  ω    -39.00  -8.00   0.50    3.00    --    6.00 123.00-142.86   62
  6  ω    -54.00 -26.00   0.50    3.00    --   14.00 157.00-140.83   56
  7  ω     -4.00  24.00   0.50    3.00    --   22.00  96.00 142.86   56
  8  ω      0.00  25.00   0.50    3.00    --   30.00  99.00 -41.71   50
  9  ω     14.00  39.00   0.50    3.00    --   38.00  85.00  20.63   50
 10  ω     24.00  49.00   0.50    3.00    --   46.00  81.00-110.06   50
 11  ω     18.00  43.00   0.50    3.00    --   46.00  91.00  70.78   50
 12  ω     18.00  55.00   0.50    3.00    --   50.30 -41.00 169.00   74
 13  ω    -10.00  16.00   0.50    3.00    --   50.30 -41.00 169.00   52
 14  ω     27.00  54.00   0.50    3.00    --   50.30 -57.00  60.00   54
 15  ω     -2.00  68.00   0.50    3.00    --   50.30 -77.00  30.00  140
 16  ω    -14.00  15.00   0.50    3.00    --   50.30 -57.00  60.00   58
 17  ω     60.00  98.00   0.50    3.00    --   50.30-125.00  90.00   76
 18  ω     88.00 114.00   0.50    3.00    --   54.00  79.00 173.53   52
 19  ω     32.00  61.00   0.50    3.00    --   54.00  82.00 108.90   58
 20  ω     30.00  56.00   0.50    3.00    --   54.00  20.00 108.84   52
 21  ω     31.00  57.00   0.50    3.00    --   54.00  83.00 -58.48   52
 22  ω     71.00 101.00   0.50    3.00    --   54.00  20.00 108.84   60
 23  ω     33.00  76.00   0.50    3.00    --   54.00  82.00  18.92   86
 24  ω     33.00  62.00   0.50    3.00    --   54.00  79.00 173.53   58
 25  ω     33.00  74.00   0.50    3.00    --   54.00  83.00-105.65   82
 26  ω     39.00  65.00   0.50    3.00    --   62.00  83.00 -39.31   52
 27  ω     40.00  66.00   0.50    3.00    --   62.00  82.00  33.13   52
 28  ω     40.00  65.00   0.50    3.00    --   62.00  82.00 -98.09   50
 29  ω     39.00 121.00   0.50    3.00    --   62.00  83.00-152.00  164
 30  ω     45.00  71.00   0.50    3.00    --   66.00  82.00 157.11   52
 31  ω     48.00  75.00   0.50    3.00    --   66.00  82.00  93.19   54
 32  ω     47.00  82.00   0.50    3.00    --   70.00  83.00 -96.80   70
 33  ω     50.00  76.00   0.50    3.00    --   70.00  82.00-172.15   52
 34  ω     49.00  84.00   0.50    3.00    --   70.00  83.00 118.08   70
 35  ω     48.00  90.00   0.50    3.00    --   70.00  83.00  71.76   84
 36  ω     97.00 130.00   0.50    3.00    --   70.00  82.00 -52.60   66
 37  ω     50.00  91.00   0.50    3.00    --   70.00  82.00 -52.60   82
 38  ω     86.00 112.00   0.50    3.00    --   70.00  83.00 118.08   52
 39  ω     59.00  97.00   0.50    3.00    --   74.00  75.00  -4.84   76
 40  ω     93.00 119.00   0.50    3.00    --   74.00  77.00 170.58   52
 41  ω     55.00  81.00   0.50    3.00    --   74.00  77.00 170.58   52
 42  ω    108.00 137.00   0.50    3.00    --   74.00  76.00  29.56   58
 43  ω     55.00  81.00   0.50    3.00    --   74.00  76.00  29.56   52
 44  ω    107.00 137.00   0.50    3.00    --   74.00  75.00  -4.84   60
 45  ω    102.00 143.00   0.50    3.00    --   74.00  61.00  77.65   82
 46  ω     61.00  95.00   0.50    3.00    --   74.00  61.00  77.65   68
 47  ω    110.00 136.00   0.50    3.00    --   78.00  63.00-107.11   52
 48  ω     64.00  89.00   0.50    3.00    --   78.00  63.00-107.11   50
 49  ω     76.00 152.00   0.50    3.00    --   82.00  43.00 162.84  152
 50  ω     75.00 157.00   0.50    3.00    --   94.00  76.00-102.72  164
 51  ω     44.00 110.00   0.50    3.00    --  102.76 -99.00-180.00  132
 52  ω     38.00  66.00   0.50    3.00    --  102.76-125.00-180.00   56
 53  ω     84.00 141.00   0.50    3.00    --  102.76  77.00 150.00  114
 54  ω     83.00 152.00   0.50    3.00    --  102.76  77.00 -90.00  138
 55  ω     92.00 158.00   0.50    3.00    --  102.76  57.00-150.00  132
 56  ω     83.00 109.00   0.50    3.00    --  102.76  77.00 -60.00   52
 57  ω     90.00 143.00   0.50    3.00    --  102.76  57.00  90.00  106
 58  ω     99.00 145.00   0.50    3.00    --  102.76 125.00-150.00   92
 59  ω    117.00 155.00   0.50    3.00    --  102.76  77.00 -30.00   76
 60  ω     83.00 112.00   0.50    3.00    --  102.76  77.00 -30.00   58
 61  ω     84.00 146.00   0.50    3.00    --  102.76  77.00  90.00  124
 62  ω     84.00 110.00   0.50    3.00    --  102.76  77.00  30.00   52
 63  ω     78.00 109.00   0.50    3.00    --  102.76-125.00  60.00   62
 64  ω     72.00 113.00   0.50    3.00    --  102.76-125.00-180.00   82
 65  ω    109.00 166.00   0.50    3.00    --  102.76 125.00  90.00  114
 66  ω    127.00 163.00   0.50    3.00    --  102.76  77.00   0.00   72
 67  ω     38.00  73.00   0.50    3.00    --  102.76-125.00  60.00   70
 68  ω     92.00 129.00   0.50    3.00    --  102.76  57.00 150.00   74
 69  ω     94.00 153.00   0.50    3.00    --  102.76  57.00  60.00  118
 70  ω     84.00 121.00   0.50    3.00    --  102.76  77.00   0.00   74
 71  ω     95.00 145.00   0.50    3.00    --  102.76  57.00-180.00  100
 72  ω     42.00 112.00   0.50    3.00    --  107.92 -44.00-114.68  140
 73  ω     53.00 105.00   0.50    3.00    --  107.92-100.00  99.23  104
 74  ω     66.00 109.00   0.50    3.00    --  107.92-116.00 -61.20   86
 75  ω     37.00  81.00   0.50    3.00    --  107.92 -52.00-158.19   88
 76  ω     47.00  74.00   0.50    3.00    --  107.92-109.00  31.92   54
 77  ω     38.00 115.00   0.50    3.00    --  107.92 -52.00  93.59  154
 78  ω     44.00 110.00   0.50    3.00    --  107.92 -45.00 -35.80  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1012336000
_diffrn_orient_matrix_UB_12      -0.1745514000
_diffrn_orient_matrix_UB_13      -0.1626928000
_diffrn_orient_matrix_UB_21      0.0078229000
_diffrn_orient_matrix_UB_22      0.1112112000
_diffrn_orient_matrix_UB_23      -0.1341612000
_diffrn_orient_matrix_UB_31      0.2240224000
_diffrn_orient_matrix_UB_32      -0.0687053000
_diffrn_orient_matrix_UB_33      -0.0313450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1293
_reflns_number_total             1413
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.94a 64-bit (release 21-06-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.060
_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)+(0.0707P)²+0.2053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1272
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24311(11) 0.04287(9) 0.39171(8) 0.0552(3) Uani 1 1 d . . . A 1
C1 C 0.1095(4) 0.0203(3) 0.1762(3) 0.0401(5) Uani 1 1 d . . . A 1
F2 F 0.3888(2) -0.1423(2) 0.0364(2) 0.0518(4) Uani 1 1 d . . . A 1
C2 C 0.1974(3) -0.0710(3) 0.0203(3) 0.0403(5) Uani 1 1 d . . . A 1
F3 F 0.1802(3) -0.1817(2) -0.3025(2) 0.0579(4) Uani 1 1 d . . . A 1
C3 C 0.0894(4) -0.0910(3) -0.1542(3) 0.0414(5) Uani 1 1 d . . . A 1
C4 C 0.1926(4) 0.4270(3) -0.0395(3) 0.0401(5) Uani 1 1 d . . . B 2
H4 H 0.320(5) 0.374(4) -0.071(4) 0.049(7) Uiso 1 1 d . . . . .
C5 C 0.0317(4) 0.4288(3) -0.1815(3) 0.0407(5) Uani 1 1 d . . . B 2
H5 H 0.044(5) 0.381(4) -0.306(4) 0.055(8) Uiso 1 1 d . . . . .
C6 C 0.1638(3) 0.4988(3) 0.1443(3) 0.0389(5) Uani 1 1 d . . . B 2
C7 C 0.3397(4) 0.5013(4) 0.2990(4) 0.0484(6) Uani 1 1 d . . . B 2
H7A H 0.294(6) 0.485(6) 0.401(5) 0.086(12) Uiso 1 1 d . . . . .
H7B H 0.426(7) 0.612(6) 0.332(5) 0.083(11) Uiso 1 1 d . . . . .
H7C H 0.439(6) 0.395(6) 0.259(5) 0.076(10) Uiso 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
Cl1 C1 1.712(2) . ?
C1 C2 1.379(3) . ?
C1 C3 1.380(3) 2 ?
F2 C2 1.335(3) . ?
C2 C3 1.383(3) . ?
F3 C3 1.343(3) . ?
C3 C1 1.380(3) 2 ?
C4 H4 0.93(3) . ?
C4 C5 1.390(3) . ?
C4 C6 1.388(3) . ?
C5 H5 0.93(3) . ?
C5 C6 1.388(3) 2_565 ?
C6 C5 1.388(3) 2_565 ?
C6 C7 1.507(3) . ?
C7 H7A 0.93(4) . ?
C7 H7B 0.93(4) . ?
C7 H7C 1.02(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 Cl1 120.60(18) . . ?
C2 C1 C3 118.5(2) . 2 ?
C3 C1 Cl1 120.94(19) 2 . ?
C1 C2 C3 120.8(2) . . ?
F2 C2 C1 120.1(2) . . ?
F2 C2 C3 119.1(2) . . ?
C1 C3 C2 120.7(2) 2 . ?
F3 C3 C1 120.3(2) . 2 ?
F3 C3 C2 119.0(2) . . ?
C5 C4 H4 118.0(18) . . ?
C6 C4 H4 120.9(18) . . ?
C6 C4 C5 121.1(2) . . ?
C4 C5 H5 124(2) . . ?
C6 C5 C4 121.1(2) 2_565 . ?
C6 C5 H5 115(2) 2_565 . ?
C4 C6 C5 117.8(2) . 2_565 ?
C4 C6 C7 121.3(2) . . ?
C5 C6 C7 120.9(2) 2_565 . ?
C6 C7 H7A 115(2) . . ?
C6 C7 H7B 109(2) . . ?
C6 C7 H7C 112(2) . . ?
H7A C7 H7B 111(3) . . ?
H7A C7 H7C 104(3) . . ?
H7B C7 H7C 105(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 F2 -0.3(3) . . . . ?
Cl1 C1 C2 C3 179.46(17) . . . . ?
C1 C2 C3 C1 -0.2(4) . . . 2 ?
C1 C2 C3 F3 -179.71(19) . . . . ?
F2 C2 C3 C1 179.5(2) . . . 2 ?
F2 C2 C3 F3 0.0(3) . . . . ?
C3 C1 C2 F2 -179.51(19) 2 . . . ?
C3 C1 C2 C3 0.2(4) 2 . . . ?
C5 C4 C6 C5 0.5(4) . . . 2_565 ?
C5 C4 C6 C7 -178.6(2) . . . . ?
C6 C4 C5 C6 -0.5(4) . . . 2_565 ?

_olex2_exptl_crystal_mounting_method '0.2mm X-ray capillary'
_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 3.675
_oxdiff_exptl_absorpt_empirical_full_min 0.520
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_118
_database_code_depnum_ccdc_archive 'CCDC 2483316'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2025-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:p-diiodotetrafluorobenzene
_chemical_formula_moiety         'C6 F4 I2, C8 H10'
_chemical_formula_sum            'C14 H10 F4 I2'
_chemical_formula_weight         508.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 C6 F4 I2'
_chemical_oxdiff_usercomment     
'Crystal grown from solution in excess p-Xylene (1:2)'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.5140(7)
_cell_length_b                   8.5541(8)
_cell_length_c                   10.2442(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.450(7)
_cell_angle_gamma                90
_cell_volume                     744.73(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.4740
_cell_measurement_theta_min      3.3890
_shelx_estimated_absorpt_T_max   0.549
_shelx_estimated_absorpt_T_min   0.404
_exptl_absorpt_coefficient_mu    4.252
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.355
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 4 13 0.0920
-3 -10 -7 0.1140
8 4 -10 0.0606
6 1 -13 0.0764
-8 -9 5 0.1471
-10 6 -4 0.1142
5 9 7 0.1173
7 7 7 0.1156
-7 -7 -7 0.1046
5 -3 12 0.0740
9 -7 3 0.0891
2 -3 14 0.0761
-1 4 -13 0.0895
3 3 -13 0.0679
-1 4 14 0.0780
-3 -3 14 0.0949
-2 0 14 0.0778
-7 7 9 0.1108
-8 -1 -11 0.0993

_exptl_crystal_preparation       'Prepared as a 2:1 molar ratio'
_exptl_crystal_recrystallization_method 'Grown in the excess p-xylene'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.165
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0653 3.5692 13.1740 -0.1902 -0.7988 -0.5708
-2.9350 -10.1957 -6.6338 0.0046 0.0255 0.9997
7.5388 4.4579 -10.4288 0.2296 0.9590 -0.1659
6.4531 0.9257 -12.5802 0.2287 0.9572 0.1775
-7.5344 -8.5153 5.2909 -0.1844 -0.7671 0.6145
-9.9634 5.6849 -3.5422 0.9231 -0.3813 -0.0494
5.3533 8.8298 7.0320 -0.2085 0.0879 -0.9741
7.2448 6.9818 7.3727 -0.4024 0.1678 -0.9000
-7.4899 -6.6846 -7.3919 0.4289 -0.1788 0.8855
5.0520 -3.2210 12.1353 -0.9209 -0.2731 -0.2782
8.9943 -7.3226 3.1294 -0.9235 0.3265 0.2013
1.8102 -2.9835 13.6754 -0.8032 -0.5332 -0.2657
-1.4748 4.3176 -13.2470 0.8239 0.5466 0.1499
3.4196 3.4151 -13.4620 0.5336 0.8395 0.1027
-0.6666 3.6236 13.7795 -0.3948 -0.6228 -0.6755
-3.3550 -3.2184 13.5513 -0.5325 -0.8378 -0.1210
-2.1070 0.2245 14.3506 -0.4866 -0.7665 -0.4191
-7.1041 6.7069 8.9189 0.2856 -0.7595 -0.5844
-7.5398 -0.6249 -10.6419 0.8268 0.0214 0.5620

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6318
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.379
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  16.00   0.50    2.50    --    0.12  85.00 -74.00   82
  2  ω    -41.00  27.00   0.50    2.50    --    0.12 -85.00 166.00  136
  3  ω      3.00  42.00   0.50    2.50    --    0.12-108.00 -52.61   78
  4  ω     33.00  64.00   0.50    2.50    --    0.12  77.00 150.00   62
  5  ω    -65.00   8.00   0.50    2.50    --    0.12 -38.00-150.00  146
  6  ω    -17.00  63.00   0.50    2.50    --    0.12  77.00 -30.00  160
  7  ω    -67.00  16.00   0.50    2.50    --    0.12 -57.00  30.00  166
  8  ω    -16.00  24.00   0.50    2.50    --    0.12  77.00 150.00   80
  9  ω     46.00  72.00   0.50    2.50    --   18.00-130.00-118.96   52
 10  ω     26.00  68.00   0.50    2.50    --   22.00-115.00  71.57   84
 11  ω     50.00  78.00   0.50    2.50    --   22.00-133.00 -24.04   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0533307000
_diffrn_orient_matrix_UB_12      0.0424897000
_diffrn_orient_matrix_UB_13      -0.0424055000
_diffrn_orient_matrix_UB_21      0.0596183000
_diffrn_orient_matrix_UB_22      0.0094897000
_diffrn_orient_matrix_UB_23      -0.0448074000
_diffrn_orient_matrix_UB_31      -0.0240484000
_diffrn_orient_matrix_UB_32      -0.0705424000
_diffrn_orient_matrix_UB_33      -0.0316337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                874
_reflns_number_total             984
_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 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.600
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.080
_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)+(0.0705P)²+0.8958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.28556(5) 0.0000 0.22746(4) 0.0376(2) Uani 1 2 d S T P . .
F1 F -0.1097(3) 0.2753(3) 0.0870(3) 0.0367(6) Uani 1 1 d . . . . .
C1 C -0.1159(7) 0.0000 0.0924(6) 0.0262(12) Uani 1 2 d S T P . .
C2 C -0.0570(5) 0.1391(5) 0.0449(4) 0.0272(9) Uani 1 1 d . . . . .
C3 C 0.0670(6) 0.3616(6) 0.5422(5) 0.0358(10) Uani 1 1 d . . . . .
H3 H 0.1121 0.2650 0.5707 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1357(8) 0.5000 0.5851(6) 0.0338(14) Uani 1 2 d S T P . .
C5 C 0.2817(9) 0.5000 0.6769(8) 0.0432(16) Uani 1 2 d S T P . .
H5A H 0.2609 0.5582 0.7564 0.065 Uiso 0.5 1 calc R U P A -1
H5B H 0.3685 0.5497 0.6338 0.065 Uiso 0.5 1 calc R U P A -1
H5C H 0.3104 0.3921 0.7000 0.065 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.060(6) . ?
F1 C2 1.330(5) . ?
C1 C2 1.390(5) . ?
C1 C2 1.390(5) 6 ?
C2 C2 1.377(9) 2 ?
C3 C3 1.389(10) 2_556 ?
C3 H3 0.9500 . ?
C3 C4 1.380(6) . ?
C4 C3 1.380(6) 6_565 ?
C4 C5 1.514(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 121.1(3) . . ?
C2 C1 I1 121.1(3) 6 . ?
C2 C1 C2 117.7(5) . 6 ?
F1 C2 C1 120.1(4) . . ?
F1 C2 C2 118.8(2) . 2 ?
C2 C2 C1 121.1(3) 2 . ?
C3 C3 H3 119.5 2_556 . ?
C4 C3 C3 121.0(3) . 2_556 ?
C4 C3 H3 119.5 . . ?
C3 C4 C3 118.1(6) 6_565 . ?
C3 C4 C5 121.0(3) 6_565 . ?
C3 C4 C5 121.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 F1 0.2(6) . . . . ?
I1 C1 C2 C2 179.7(4) . . . 2 ?
C2 C1 C2 F1 179.8(3) 6 . . . ?
C2 C1 C2 C2 -0.7(9) 6 . . 2 ?
C3 C3 C4 C3 0.2(12) 2_556 . . 6_565 ?
C3 C3 C4 C5 180.0(7) 2_556 . . . ?

_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 1.930
_oxdiff_exptl_absorpt_empirical_full_min 0.608
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_692
_database_code_depnum_ccdc_archive 'CCDC 2483311'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2025-08-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        p-xylene:dichlorotetrafluorobenzene
_chemical_formula_moiety         'C6 Cl2 F4, C8 H10'
_chemical_formula_sum            'C14 H10 Cl2 F4'
_chemical_formula_weight         325.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H10 F4 Cl2'
_chemical_oxdiff_usercomment     '0.2mm capillary new sample made 4/4/24'
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'
Cl Cl 0.3639 0.7018 '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 1 21/n'
_space_group_name_Hall           '-P 2n'
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                   14.83539(17)
_cell_length_b                   7.90142(9)
_cell_length_c                   5.98834(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                96.4553(11)
_cell_volume                     697.507(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11619
_cell_measurement_temperature    220
_cell_measurement_theta_max      76.8600
_cell_measurement_theta_min      5.6510
_shelx_estimated_absorpt_T_max   0.440
_shelx_estimated_absorpt_T_min   0.102
_exptl_absorpt_coefficient_mu    4.512
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.122
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 -1 0 0.4541
9 1 0 0.4541
-2 4 2 0.1112
0 0 4 0.1217
0 0 -4 0.0970
2 -4 2 0.1094
-2 4 -2 0.1058
2 -4 -2 0.0969
-2 4 2 0.1217
0 0 -4 0.0942
0 0 4 0.1237
-2 4 -2 0.1038
-2 5 0 0.1113
2 -5 0 0.1066
-1 3 3 0.1226
1 -3 -3 0.0950
1 -3 3 0.1172
-1 3 -3 0.1009

_exptl_crystal_preparation       '50:50 molar mixture'
_exptl_crystal_recrystallization_method 'Grown in situ'
_exptl_crystal_size_max          0.931
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.218
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.2247 -0.8724 0.2588 -0.0024 -0.0131 -0.9999
9.2247 0.8724 -0.2588 0.0024 0.0131 0.9999
-1.8392 4.4319 1.9224 0.2329 0.9725 0.0079
0.1540 0.0361 3.8858 -0.7246 0.6869 -0.0558
-0.2249 -0.0423 -3.8852 0.7249 -0.6872 0.0481
2.0147 -4.3856 1.9652 -0.9569 -0.2840 -0.0610
-1.7436 4.3995 -1.9693 0.9548 0.2834 0.0897
1.5558 -4.4538 -1.9121 -0.2327 -0.9718 -0.0384
-1.5387 4.4550 1.9115 0.2327 0.9717 0.0403
-0.2894 -0.0476 -3.8844 0.7252 -0.6873 0.0412
0.2585 0.0448 3.8848 -0.7251 0.6872 -0.0445
-1.8983 4.0923 -2.3040 0.9811 0.1825 0.0639
-2.1256 5.0979 -0.0295 0.6870 0.7249 0.0505
2.1840 -5.0943 0.0278 -0.6872 -0.7251 -0.0443
-0.8722 2.5882 3.3533 -0.2845 0.9585 -0.0168
0.8930 -2.5862 -3.3538 0.2845 -0.9585 0.0190
1.1155 -2.5192 3.3765 -0.9692 0.2322 -0.0819
-1.1820 2.5148 -3.3764 0.9698 -0.2323 0.0748

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.399
_diffrn_reflns_theta_min         6.004
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00  70.00   0.50    2.00    --   50.30-132.00 -35.00   50
  2  ω     59.00 100.00   0.50    2.00    --   50.30-138.00 148.00   82
  3  ω    101.00 127.00   0.50    2.00    --  102.76-138.00 148.00   52
  4  ω     95.00 121.00   0.50    2.00    --  102.76-132.00 -35.00   52
  5  ω    125.00 152.00   0.50    2.00    --  102.76 138.00-149.00   54
  6  ω     88.00 155.00   0.50    2.00    --  102.76 132.00  34.00  134
  7  ω    -43.00 -14.00   0.50    2.00    --    6.00 126.00  -3.26   58
  8  ω    -35.00  -3.00   0.50    2.00    --    6.00 115.00  66.98   64
  9  ω    -49.00 -23.00   0.50    2.00    --   14.00 149.00  14.50   52
 10  ω     -9.00  16.00   0.50    2.00    --   22.00  98.00-178.68   50
 11  ω      3.00  31.00   0.50    2.00    --   34.00  97.00  22.31   56
 12  ω      5.00  37.00   0.50    2.00    --   34.00  93.00 166.90   64
 13  ω     17.00  43.00   0.50    2.00    --   42.00  91.00-160.23   52
 14  ω     16.00  41.00   0.50    2.00    --   42.00  88.00  -8.63   50
 15  ω     15.00  46.00   0.50    2.00    --   42.00  90.00 100.01   62
 16  ω     15.00  61.00   0.50    2.00    --   50.30 -57.00   0.00   92
 17  ω     -5.00  63.00   0.50    2.00    --   50.30 -57.00-120.00  136
 18  ω     73.00  98.00   0.50    2.00    --   50.30  19.00 -30.00   50
 19  ω     25.00  62.00   0.50    2.00    --   50.30  19.00 -30.00   74
 20  ω      5.00  59.00   0.50    2.00    --   50.30 -57.00 120.00  108
 21  ω     31.00  57.00   0.50    2.00    --   54.00  83.00  70.94   52
 22  ω     67.00 108.00   0.50    2.00    --   54.00  83.00  70.94   82
 23  ω     32.00  62.00   0.50    2.00    --   54.00  82.00  30.62   60
 24  ω     84.00 110.00   0.50    2.00    --   54.00  83.00 -26.02   52
 25  ω     31.00  57.00   0.50    2.00    --   54.00  83.00 -26.02   52
 26  ω     32.00  58.00   0.50    2.00    --   54.00  82.00 -89.34   52
 27  ω     35.00  69.00   0.50    2.00    --   58.00  83.00 166.00   68
 28  ω     86.00 112.00   0.50    2.00    --   58.00  83.00 129.64   52
 29  ω     35.00  61.00   0.50    2.00    --   58.00  83.00 129.64   52
 30  ω     36.00  83.00   0.50    2.00    --   58.00  81.00-159.73   94
 31  ω     83.00 118.00   0.50    2.00    --   58.00  83.00-120.64   70
 32  ω     35.00  73.00   0.50    2.00    --   58.00  83.00-120.64   76
 33  ω     41.00  74.00   0.50    2.00    --   62.00  82.00 -23.39   66
 34  ω     43.00  69.00   0.50    2.00    --   66.00  83.00  92.65   52
 35  ω     92.00 125.00   0.50    2.00    --   66.00  82.00  40.79   66
 36  ω     94.00 125.00   0.50    2.00    --   66.00  83.00  92.65   62
 37  ω     44.00  77.00   0.50    2.00    --   66.00  82.00  40.79   66
 38  ω     44.00  69.00   0.50    2.00    --   66.00  81.00 -66.51   50
 39  ω     44.00  74.00   0.50    2.00    --   66.00  82.00-106.88   60
 40  ω     43.00  79.00   0.50    2.00    --   66.00  83.00 175.88   72
 41  ω     48.00  78.00   0.50    2.00    --   70.00  82.00-150.94   60
 42  ω     47.00  76.00   0.50    2.00    --   70.00  83.00 111.86   58
 43  ω    112.00 139.00   0.50    2.00    --   74.00  71.00-105.57   54
 44  ω     58.00  86.00   0.50    2.00    --   74.00  71.00-105.57   56
 45  ω    111.00 136.00   0.50    2.00    --   74.00  79.00  57.78   50
 46  ω     53.00  86.00   0.50    2.00    --   74.00  79.00  57.78   66
 47  ω     63.00  89.00   0.50    2.00    --   78.00  66.00 -40.58   52
 48  ω     56.00 100.00   0.50    2.00    --   78.00  82.00 -10.48   88
 49  ω    102.00 146.00   0.50    2.00    --   82.00  68.00 144.19   88
 50  ω     66.00 146.00   0.50    2.00    --   82.00  71.00 -32.72  160
 51  ω     67.00  92.00   0.50    2.00    --   82.00  68.00 144.19   50
 52  ω     71.00 109.00   0.50    2.00    --   86.00  68.00  85.33   76
 53  ω     65.00 148.00   0.50    2.00    --   86.00  79.00 155.13  166
 54  ω     64.00 145.00   0.50    2.00    --   86.00  82.00-175.28  162
 55  ω     66.00 148.00   0.50    2.00    --   86.00  78.00  -2.74  164
 56  ω    122.00 152.00   0.50    2.00    --   86.00  68.00  85.33   60
 57  ω    116.00 158.00   0.50    2.00    --   90.00  64.00 -87.44   84
 58  ω     76.00 103.00   0.50    2.00    --   90.00  64.00 -87.44   54
 59  ω    140.00 172.00   0.50    2.00    --  102.76  57.00-120.00   64
 60  ω     99.00 135.00   0.50    2.00    --  102.76  57.00-120.00   72
 61  ω     41.00 109.00   0.50    2.00    --  102.76 -99.00  30.00  136
 62  ω     40.00 109.00   0.50    2.00    --  102.76-125.00  30.00  138
 63  ω    137.00 162.00   0.50    2.00    --  102.76  77.00 -60.00   50
 64  ω     83.00 142.00   0.50    2.00    --  102.76  77.00  30.00  118
 65  ω    132.00 165.00   0.50    2.00    --  102.76  77.00 -90.00   66
 66  ω     83.00 110.00   0.50    2.00    --  102.76  77.00 -90.00   54
 67  ω     84.00 113.00   0.50    2.00    --  102.76  77.00 -60.00   58
 68  ω    135.00 160.00   0.50    2.00    --  102.76  77.00-150.00   50
 69  ω     83.00 108.00   0.50    2.00    --  102.76  77.00-150.00   50
 70  ω     41.00 100.00   0.50    2.00    --  102.76-125.00 -90.00  118
 71  ω    136.00 162.00   0.50    2.00    --  102.76  77.00  90.00   52
 72  ω    119.00 163.00   0.50    2.00    --  102.76  77.00-180.00   88
 73  ω     98.00 172.00   0.50    2.00    --  102.76  57.00 -30.00  148
 74  ω     83.00 152.00   0.50    2.00    --  102.76  77.00 120.00  138
 75  ω     83.00 109.00   0.50    2.00    --  102.76  77.00  90.00   52
 76  ω     86.00 111.00   0.50    2.00    --  102.76  77.00-180.00   50
 77  ω     90.00 116.00   0.50    2.00    --  102.76  57.00  30.00   52
 78  ω     58.00 103.00   0.50    2.00    --  102.76 -99.00 120.00   90
 79  ω     41.00  93.00   0.50    2.00    --  107.92 -41.00 174.69  104
 80  ω     37.00 118.00   0.50    2.00    --  107.92 -52.00 -85.09  162
 81  ω     40.00 111.00   0.50    2.00    --  107.92 -44.00  92.05  142
 82  ω     50.00 107.00   0.50    2.00    --  107.92 -93.00 150.94  114
 83  ω     45.00 110.00   0.50    2.00    --  107.92-113.00 -39.62  130
 84  ω     44.00  89.00   0.50    2.00    --  107.92 -43.00   5.15   90
 85  ω     48.00 107.00   0.50    2.00    --  107.92 -95.00  49.67  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0169608008
_diffrn_orient_matrix_UB_12      0.1266081806
_diffrn_orient_matrix_UB_13      -0.1869836433
_diffrn_orient_matrix_UB_21      -0.0069168792
_diffrn_orient_matrix_UB_22      0.1403264041
_diffrn_orient_matrix_UB_23      0.1757369454
_diffrn_orient_matrix_UB_31      0.1028810212
_diffrn_orient_matrix_UB_32      0.0526937368
_diffrn_orient_matrix_UB_33      -0.0189181850
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1371
_reflns_number_total             1460
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.070
_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)+(0.0576P)²+0.0693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C7-H7A \\sim C7-H7B \\sim C7-H7C
 with sigma of 0.02
 H7A-H7B \\sim H7B-H7C \\sim H7C-H7A
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uiso(H7A) = Uiso(H7B) = Uiso(H7C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30081(2) 0.38184(5) 0.63479(6) 0.06611(17) Uani 1 1 d . . . . .
F2 F 0.43549(6) 0.60236(11) 0.89521(12) 0.0612(2) Uani 1 1 d . . . . .
F3 F 0.39192(5) 0.30111(10) 0.21719(14) 0.0638(2) Uani 1 1 d . . . . .
C1 C 0.41005(8) 0.44855(15) 0.5593(2) 0.0479(3) Uani 1 1 d . . . . .
C2 C 0.46692(9) 0.55081(15) 0.69999(19) 0.0477(3) Uani 1 1 d . . . . .
C3 C 0.44463(9) 0.39944(15) 0.35765(19) 0.0482(3) Uani 1 1 d . . . . .
C4 C 0.52970(14) -0.0466(2) 0.2955(3) 0.0721(4) Uani 1 1 d . . . . .
H4 H 0.5473(16) -0.079(3) 0.150(4) 0.097(7) Uiso 1 1 d . . . . .
C5 C 0.44105(14) -0.0940(2) 0.3581(3) 0.0723(5) Uani 1 1 d . . . . .
H5 H 0.3988(13) -0.162(2) 0.272(4) 0.083(6) Uiso 1 1 d . . . . .
C6 C 0.40891(13) -0.04877(19) 0.5659(3) 0.0685(4) Uani 1 1 d . . . . .
C7 C 0.31292(18) -0.1019(3) 0.6354(4) 0.0901(6) Uani 1 1 d D . . . .
H7A H 0.2675(19) -0.054(4) 0.560(5) 0.175(8) Uiso 1 1 d D . . . .
H7B H 0.297(2) -0.219(3) 0.628(5) 0.175(8) Uiso 1 1 d D . . . .
H7C H 0.303(2) -0.078(4) 0.786(4) 0.175(8) Uiso 1 1 d 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
Cl1 C1 1.7078(12) . ?
F2 C2 1.3389(14) . ?
F3 C3 1.3364(13) . ?
C1 C2 1.3860(18) . ?
C1 C3 1.3843(18) . ?
C2 C3 1.3710(18) 3_666 ?
C3 C2 1.3710(18) 3_666 ?
C4 H4 0.95(2) . ?
C4 C5 1.378(3) . ?
C4 C6 1.390(3) 3_656 ?
C5 H5 0.93(2) . ?
C5 C6 1.394(2) . ?
C6 C4 1.390(3) 3_656 ?
C6 C7 1.498(3) . ?
C7 H7A 0.93(2) . ?
C7 H7B 0.93(2) . ?
C7 H7C 0.94(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 Cl1 120.88(10) . . ?
C3 C1 Cl1 120.87(10) . . ?
C3 C1 C2 118.24(11) . . ?
F2 C2 C1 119.88(12) . . ?
F2 C2 C3 119.17(11) . 3_666 ?
C3 C2 C1 120.95(11) 3_666 . ?
F3 C3 C1 120.06(11) . . ?
F3 C3 C2 119.13(11) . 3_666 ?
C2 C3 C1 120.80(11) 3_666 . ?
C5 C4 H4 117.3(14) . . ?
C5 C4 C6 122.14(16) . 3_656 ?
C6 C4 H4 120.6(14) 3_656 . ?
C4 C5 H5 124.3(13) . . ?
C4 C5 C6 121.11(17) . . ?
C6 C5 H5 114.6(13) . . ?
C4 C6 C5 116.75(18) 3_656 . ?
C4 C6 C7 122.04(17) 3_656 . ?
C5 C6 C7 121.21(18) . . ?
C6 C7 H7A 118(2) . . ?
C6 C7 H7B 113(2) . . ?
C6 C7 H7C 112(2) . . ?
H7A C7 H7B 105.1(18) . . ?
H7A C7 H7C 104.5(18) . . ?
H7B C7 H7C 102.7(18) . . ?

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
Cl1 C1 C2 F2 -1.88(15) . . . . ?
Cl1 C1 C2 C3 178.17(9) . . . 3_666 ?
Cl1 C1 C3 F3 1.24(16) . . . . ?
Cl1 C1 C3 C2 -178.17(9) . . . 3_666 ?
C2 C1 C3 F3 -179.88(11) . . . . ?
C2 C1 C3 C2 0.71(19) . . . 3_666 ?
C3 C1 C2 F2 179.24(10) . . . . ?
C3 C1 C2 C3 -0.71(19) . . . 3_666 ?
C4 C5 C6 C4 0.4(2) . . . 3_656 ?
C4 C5 C6 C7 -179.27(14) . . . . ?
C6 C4 C5 C6 -0.4(3) 3_656 . . . ?

_olex2_exptl_crystal_mounting_method '0.2mm diameter X-ray capillary'
_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 3.316
_oxdiff_exptl_absorpt_empirical_full_min 0.740
