# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_xstr0591a
_database_code_depnum_ccdc_archive 'CCDC 1518503'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F6, C9 H12'
_chemical_formula_sum            'C15 H12 F6'
_chemical_formula_weight         306.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 F6 C9 H12'
_chemical_oxdiff_usercomment     'C6F6 : C6H3Me3 (1,3,5) 50:50'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P b n m'
_space_group_name_Hall           '-P 2c 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.08543(18)
_cell_length_b                   15.3044(4)
_cell_length_c                   13.2959(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1441.79(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5792
_cell_measurement_temperature    189.99(10)
_cell_measurement_theta_max      72.2210
_cell_measurement_theta_min      6.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       teardrop
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -4 0 0.3452
2 8 3 0.3030
1 -9 -3 0.2855
2 5 -6 0.3818
-2 -3 -7 0.2164
0 -7 -6 0.2230
0 -10 -2 0.3093
2 -8 3 0.2841
2 -6 5 0.2816
-3 -6 3 0.4445
-3 2 -6 0.2623
-1 0 -8 0.1942
0 -8 -5 0.2431
-1 -3 8 0.2990
4 2 2 0.3803
-2 -1 -8 0.1817
-1 -6 -7 0.2170
0 -2 8 0.2702
3 4 6 0.2987
3 -5 4 0.3107
0 2 -9 0.2329
1 -8 -4 0.2673
-2 -8 -3 0.3641
-3 -7 3 0.4381
-3 6 -5 0.3051
-2 -9 2 0.3916
-1 -5 -7 0.2000
1 -1 -8 0.2391
-5 -1 1 0.4648
2 2 8 0.2634
0 3 8 0.2484
1 6 6 0.2375
3 -2 6 0.2985
-2 7 5 0.3425
4 -3 2 0.3499
3 5 3 0.3605
4 -1 5 0.3347
-1 9 4 0.2992
-2 3 -7 0.2338
2 -6 -5 0.2726
1 0 8 0.2492
-1 1 8 0.2706
-1 6 7 0.2727
1 -5 7 0.2652
-1 -10 0 0.3380
1 9 3 0.2536
1 5 7 0.2315
1 -7 6 0.2826
4 3 -4 0.3939
1 10 0 0.2844
-4 -1 -3 0.3834
1 -6 -7 0.2228
3 -7 2 0.2929
3 8 -1 0.3879
4 4 -1 0.4079
2 -4 7 0.2678
5 0 0 0.3883
3 3 7 0.2846
1 9 4 0.2343
-2 7 -5 0.2861
-4 -5 3 0.4598
-4 5 -4 0.3491
-4 3 -2 0.4018
-1 -9 -3 0.2956
0 -4 -8 0.1874
4 -6 2 0.3116
-2 2 8 0.3599
0 -5 7 0.2947
0 5 -7 0.2854
0 -3 -8 0.1955
-2 -2 8 0.3432
1 -8 4 0.3108
-4 -3 3 0.4765
-1 -6 7 0.3608
2 7 5 0.2542
3 -2 -6 0.3176
3 6 -2 0.4040
0 10 2 0.2430
3 2 -6 0.3708
0 8 5 0.2263
0 7 6 0.2248

_exptl_crystal_size_max          0.887
_exptl_crystal_size_mid          0.596
_exptl_crystal_size_min          0.429
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
4.1202 -4.4112 0.1545 -0.3654 -0.8844 -0.2903
2.3199 7.5794 3.4908 0.8052 -0.2999 -0.5116
0.7461 -9.3144 -2.6439 -0.9053 -0.3395 0.2555
2.4361 5.1343 -5.8091 -0.1064 0.1057 -0.9887
-2.3895 -2.6152 -7.0145 -0.7137 0.7004 0.0138
0.3407 -7.0408 -6.0500 -0.9992 0.0081 -0.0383
0.1319 -9.7762 -1.5005 -0.8421 -0.3160 0.4371
2.2463 -7.8507 3.1885 -0.3584 -0.8659 0.3490
2.3816 -6.1795 5.0664 -0.0892 -0.9295 0.3577
-3.2412 -5.9790 3.2543 -0.1464 0.1423 0.9789
-3.0310 2.2376 -6.1926 -0.2824 0.9516 -0.1215
-0.8093 0.2788 -8.4906 -0.6352 0.6240 -0.4552
-0.2399 -8.0867 -4.9876 -0.9860 0.0078 0.1666
-0.8152 -2.8931 8.1134 0.4326 -0.4256 0.7948
4.3659 1.5170 2.3838 0.2447 -0.8223 -0.5137
-1.5012 -0.9368 -8.1152 -0.6870 0.6746 -0.2702
-1.2067 -5.8600 -6.5880 -0.9348 0.3488 0.0667
-0.2236 -1.9782 8.4464 0.5189 -0.5102 0.6858
2.8798 3.6296 5.9449 0.6987 -0.6854 -0.2053
3.3688 -4.9554 3.9969 -0.0949 -0.9916 0.0882
-0.0005 1.6205 -8.5137 -0.5479 0.5386 -0.6401
1.4376 -8.3139 -3.8700 -0.9361 -0.3507 0.0279
-2.3954 -7.6537 -3.1753 -0.7850 0.2923 0.5462
-2.9870 -6.7975 2.8755 -0.2398 0.0884 0.9668
-2.6854 5.8751 -4.7978 0.0916 0.9548 -0.2828
-1.6384 -8.9752 2.0658 -0.4811 -0.1813 0.8577
-0.9494 -5.3577 -7.0429 -0.9366 0.3495 -0.0253
0.7900 -1.2826 -8.4270 -0.7656 0.2863 -0.5762
-4.5735 -0.6567 0.7563 0.0678 0.7156 0.6953
2.0502 1.9549 7.5351 0.7099 -0.6968 0.1023
-0.1625 2.8824 8.2509 0.8622 -0.3222 0.3910
1.3022 6.0385 6.3998 0.9321 -0.3477 -0.1016
3.0396 -2.2233 6.1816 0.2825 -0.9519 0.1188
-1.9900 7.0517 4.7907 0.9219 0.3451 0.1763
4.1560 -3.1709 2.4672 -0.0928 -0.9720 -0.2160
3.4931 5.1229 3.4284 0.6040 -0.5921 -0.5334
3.8234 -0.6158 4.7686 0.2808 -0.9451 -0.1674
-1.3221 8.5208 3.6703 0.9343 0.3501 -0.0678
-2.2729 3.3298 -6.9214 -0.2683 0.9047 -0.3311
2.3417 -5.9407 -5.3377 -0.8870 -0.3319 -0.3211
0.8618 -0.1888 8.4742 0.6399 -0.6286 0.4421
-0.8134 1.2200 8.4262 0.7612 -0.2847 0.5828
-0.8945 5.7313 6.8423 0.9715 -0.0081 0.2370
0.9230 -4.6868 7.4088 0.2230 -0.7531 0.6189
-0.6915 -9.8200 0.1054 -0.7091 -0.2665 0.6528
1.0442 8.9808 3.1223 0.8958 -0.0067 -0.4444
0.8341 5.1232 7.2236 0.9349 -0.3489 0.0655
1.2174 -6.9285 5.7461 -0.0768 -0.7971 0.5989
3.8676 3.4289 -3.6082 -0.0777 -0.3282 -0.9414
0.5630 9.8571 0.1510 0.7336 0.2756 -0.6212
-4.3046 -1.1026 -2.8924 -0.2547 0.8563 0.4494
0.7309 -6.1518 -6.6318 -0.9840 0.0081 -0.1779
2.8754 -7.2129 2.4646 -0.3758 -0.9085 0.1825
2.9653 7.5251 -0.9209 0.4471 -0.1659 -0.8790
4.2075 3.8563 -1.0042 0.1539 -0.5155 -0.8429
1.9066 -3.7611 7.1406 0.2582 -0.8708 0.4183
4.6003 -0.0805 -0.1403 -0.0743 -0.7830 -0.6175
2.5623 2.9631 6.6881 0.7116 -0.6983 -0.0775
0.6825 8.6630 4.0207 0.9473 -0.0073 -0.3204
-1.7450 7.4352 -4.6919 0.2035 0.8481 -0.4893
-3.8013 -4.7238 2.6168 -0.0966 0.3223 0.9417
-3.5655 4.6092 -3.6981 0.0952 0.9952 -0.0232
-4.2931 2.6775 -2.0479 0.0909 0.9530 0.2891
-0.9369 -8.9019 -3.3997 -0.9131 0.0069 0.4078
-0.4066 -4.2075 -7.7777 -0.9160 0.3420 -0.2099
3.5111 -6.1748 1.5087 -0.3820 -0.9239 -0.0224
-2.0659 1.6352 7.5777 0.7409 -0.0067 0.6715
0.1599 -5.2068 7.3436 0.1890 -0.6389 0.7457
-0.1531 5.2107 -7.3420 -0.1887 0.6378 -0.7468
0.0372 -3.1845 -8.1719 -0.8768 0.3275 -0.3521
-1.7756 -1.5762 7.8432 0.5207 -0.1952 0.8311
0.9604 -8.4001 4.2382 -0.3006 -0.7256 0.6190
-4.1168 -2.6194 3.1157 0.1020 0.4297 0.8972
-1.1820 -5.7323 6.6925 0.1158 -0.3930 0.9122
1.7412 6.7968 5.3780 0.9025 -0.3365 -0.2687
3.0676 -1.8157 -6.2342 -0.6614 -0.2469 -0.7082
3.4744 6.1170 -1.9545 0.2556 -0.2496 -0.9340
-0.2978 9.6880 1.8140 0.8622 0.3235 -0.3898
3.1675 2.4565 -5.8868 -0.3196 -0.1185 -0.9401
0.3394 8.2332 4.7823 0.9795 -0.0077 -0.2013
-0.1345 7.4495 5.6990 0.9994 -0.0080 -0.0349

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11235
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.616
_diffrn_reflns_theta_min         6.886
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      189.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_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  32.00   1.00    1.00    --  -42.62  38.00 -60.00   77
  2  ω     -1.00  30.00   1.00    1.00    --  -42.62  38.00-150.00   31
  3  ω    -47.00 -22.00   1.00    1.00    --  -42.62  38.00-180.00   25
  4  ω    -71.00  19.00   1.00    1.00    --  -42.62  57.00  60.00   90
  5  ω     57.00  84.00   1.00    1.00    --  106.36 -45.00-150.00   27
  6  ω     37.00  78.00   1.00    1.00    --  106.36 -45.00-120.00   41
  7  ω     24.00 108.00   1.00    1.00    --  106.36 -94.00-150.00   84
  8  ω     26.00 123.00   1.00    1.00    --  106.36 -15.00   0.00   97
  9  ω     90.00 164.00   1.00    1.00    --  106.36  45.00 -30.00   74
 10  ω     42.00  83.00   1.00    1.00    --  106.36 -45.00  90.00   41
 11  ω     94.00 119.00   1.00    1.00    --  106.36-125.00 150.00   25
 12  ω     49.00  75.00   1.00    1.00    --  106.36-125.00 150.00   26
 13  ω   -124.00 -99.00   1.00    1.00    --  -42.87 -99.00-180.00   25
 14  ω    -27.00  -2.00   1.00    1.00    --  -42.87 125.00-180.00   25
 15  ω    -24.00  30.00   1.00    1.00    --  -42.87  38.00-180.00   54
 16  ω     10.00  43.00   1.00    1.00    --   42.87  77.00 120.00   33
 17  ω     58.00 101.00   1.00    1.00    --   42.87-135.00 -33.00   43
 18  ω     32.00  88.00   1.00    1.00    --  106.36 -30.00-180.00   56
 19  ω     35.00  87.00   1.00    1.00    --  106.36 -94.00  90.00   52
 20  ω    144.00 170.00   1.00    1.00    --  106.36 125.00 150.00   26
 21  ω     30.00  76.00   1.00    1.00    --  106.36 -30.00 -30.00   46
 22  ω     50.00 103.00   1.00    1.00    --  106.36 -94.00   0.00   53
 23  ω    103.00 129.00   1.00    1.00    --  106.36 125.00 -90.00   26
 24  ω    151.00 177.00   1.00    1.00    --  106.36 125.00 -90.00   26
 25  ω     49.00  91.00   1.00    1.00    --  106.36 -30.00 -90.00   42
 26  ω     40.00  66.00   1.00    1.00    --  106.36 -45.00 150.00   26
 27  ω     55.00  81.00   1.00    1.00    --  106.36 -30.00-150.00   26
 28  ω     60.00 105.00   1.00    1.00    --  106.36 -94.00 -60.00   45
 29  ω     70.00  96.00   1.00    1.00    --  106.36 -45.00 150.00   26
 30  ω     35.00  64.00   1.00    1.00    --  106.36 -30.00 150.00   29
 31  ω     99.00 124.00   1.00    1.00    --  106.36 125.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124683447
_diffrn_orient_matrix_UB_12      0.0739296758
_diffrn_orient_matrix_UB_13      0.0784243534
_diffrn_orient_matrix_UB_21      -0.1712417589
_diffrn_orient_matrix_UB_22      0.0385957760
_diffrn_orient_matrix_UB_23      -0.0559013992
_diffrn_orient_matrix_UB_31      -0.1332618928
_diffrn_orient_matrix_UB_32      -0.0564016138
_diffrn_orient_matrix_UB_33      0.0644619921
_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                1285
_reflns_number_total             1505
_reflns_odcompleteness_completeness 99.41
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.033(7)
_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   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1505
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.086
_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)+(0.1313P)²+0.1739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2221
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C8-H8A = C8-H8B = C8-H8C
 0.95 with sigma of 0.001
 H8A-H8B = H8C-H8A = H8B-H8C
 1.551 with sigma of 0.001
 C9-H9A = C9-H9B = C9-H9C
 0.95 with sigma of 0.001
 C9-H9D = C9-H9E = C9-H9F
 0.95 with sigma of 0.001
 H9A-H9B = H9C-H9A = H9B-H9C
 1.551 with sigma of 0.001
 H9D-H9E = H9F-H9D = H9E-H9F
 1.551 with sigma of 0.001
 H8A-H8A_$1 \\sim H8A_$1-H8B
 with sigma of 0.001
 C7-H8A \\sim C7-H8B \\sim C7-H8C \\sim C7-H8A_$1 \\sim C7-H8B_$1 \\sim
C7-H8C_$1
 with sigma of 0.001
 C5-H9A \\sim C5-H9B \\sim C5-H9C \\sim C5-H9D \\sim C5-H9E \\sim C5-H9F
 with sigma of 0.001
3. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H9D(0.5)
 H9E(0.5) H9F(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8494(3) 0.50976(18) 0.6987(3) 0.1237(12) Uani 1 1 d . . . A 1
C2 C 0.8810(3) 0.4331(2) 0.6471(2) 0.1026(9) Uani 1 1 d . . . A 1
C3 C 0.9122(3) 0.35833(14) 0.69927(16) 0.0823(7) Uani 1 1 d . . . A 1
F1 F 0.8173(4) 0.58353(14) 0.6490(3) 0.2101(14) Uani 1 1 d . . . A 1
F2 F 0.8789(3) 0.43130(17) 0.54753(16) 0.1749(12) Uani 1 1 d . . . A 1
F3 F 0.9413(3) 0.28375(11) 0.65006(11) 0.1183(7) Uani 1 1 d . . . A 1
C4 C 0.5768(3) 0.67735(15) 0.2500 0.0717(7) Uani 1 2 d S T P B 2
H4 H 0.5539 0.7385 0.2500 0.086 Uiso 1 2 calc RS T P B 2
C5 C 0.5930(2) 0.63434(13) 0.34078(15) 0.0747(6) Uani 1 1 d D . . B 2
C6 C 0.6275(3) 0.54528(13) 0.33943(16) 0.0777(6) Uani 1 1 d . . . B 2
H6 H 0.6396 0.5148 0.4013 0.093 Uiso 1 1 calc R . . B 2
C7 C 0.6447(3) 0.49952(16) 0.2500 0.0771(8) Uani 1 2 d DS T P B 2
C8 C 0.6789(6) 0.40250(19) 0.2500 0.1256(16) Uani 1 2 d DS T P B 2
H8A H 0.5781(7) 0.3739(2) 0.28368(4) 0.188 Uiso 0.5 1 d DR . . C 2
H8B H 0.6861(7) 0.3820(2) 0.18266(9) 0.188 Uiso 0.5 1 d DR . . D 2
H8C H 0.7941(6) 0.3902(3) 0.28370(18) 0.188 Uiso 0.5 1 d DR . . E 2
C9 C 0.5744(4) 0.6837(2) 0.4389(2) 0.1200(10) Uani 1 1 d D . . B 2
H9A H 0.6849(12) 0.7175(10) 0.4500(8) 0.180 Uiso 0.5 1 d DR . . F 2
H9B H 0.4677(16) 0.7212(9) 0.4358(6) 0.180 Uiso 0.5 1 d DR . . G 2
H9C H 0.559(3) 0.6433(3) 0.4926(3) 0.180 Uiso 0.5 1 d DR . . H 2
H9D H 0.6731(17) 0.6667(11) 0.4831(6) 0.180 Uiso 0.5 1 d DR . . I 2
H9E H 0.582(3) 0.74465(19) 0.4264(4) 0.180 Uiso 0.5 1 d DR . . J 2
H9F H 0.4560(13) 0.6706(11) 0.4689(8) 0.180 Uiso 0.5 1 d DR . . K 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
C1 C1 1.365(7) 6_557 ?
C1 C2 1.378(4) . ?
C1 F1 1.328(3) . ?
C2 C3 1.356(4) . ?
C2 F2 1.324(4) . ?
C3 C3 1.349(4) 6_557 ?
C3 F3 1.332(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(2) 6_556 ?
C4 C5 1.380(2) . ?
C5 C6 1.385(3) . ?
C5 C9 1.513(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(3) . ?
C7 C6 1.385(3) 6_556 ?
C7 C8 1.504(4) . ?
C8 H8A 0.9501(10) . ?
C8 H8B 0.9500(10) . ?
C8 H8C 0.9501(10) . ?
C9 H9A 0.9500(10) . ?
C9 H9B 0.9500(10) . ?
C9 H9C 0.9501(10) . ?
C9 H9D 0.9500(10) . ?
C9 H9E 0.9500(10) . ?
C9 H9F 0.9500(10) . ?

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
C1 C1 C2 119.84(17) 6_557 . ?
F1 C1 C1 119.8(2) . 6_557 ?
F1 C1 C2 120.3(3) . . ?
C3 C2 C1 119.4(3) . . ?
F2 C2 C1 120.9(3) . . ?
F2 C2 C3 119.7(3) . . ?
C3 C3 C2 120.76(17) 6_557 . ?
F3 C3 C2 119.8(2) . . ?
F3 C3 C3 119.43(12) . 6_557 ?
C5 C4 H4 119.0 . . ?
C5 C4 H4 119.0 6_556 . ?
C5 C4 C5 122.1(2) . 6_556 ?
C4 C5 C6 118.22(18) . . ?
C4 C5 C9 120.6(2) . . ?
C6 C5 C9 121.2(2) . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.61(18) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C6 118.3(2) . 6_556 ?
C6 C7 C8 120.87(12) . . ?
C6 C7 C8 120.87(12) 6_556 . ?
C7 C8 H8A 109.52(14) . . ?
C7 C8 H8B 109.53(14) . . ?
C7 C8 H8C 109.52(14) . . ?
H8A C8 H8B 109.43(17) . . ?
H8A C8 H8C 109.41(17) . . ?
H8B C8 H8C 109.43(17) . . ?
C5 C9 H9A 109.51(12) . . ?
C5 C9 H9B 109.51(12) . . ?
C5 C9 H9C 109.50(11) . . ?
C5 C9 H9D 109.51(12) . . ?
C5 C9 H9E 109.51(11) . . ?
C5 C9 H9F 109.51(12) . . ?
H9A C9 H9B 109.44(14) . . ?
H9A C9 H9C 109.43(15) . . ?
H9A C9 H9D 56.3(16) . . ?
H9A C9 H9E 56.1(16) . . ?
H9A C9 H9F 141.0(2) . . ?
H9B C9 H9C 109.43(15) . . ?
H9B C9 H9D 141.0(2) . . ?
H9B C9 H9E 56.3(16) . . ?
H9B C9 H9F 56.1(16) . . ?
H9C C9 H9D 56.1(16) . . ?
H9C C9 H9E 141.0(2) . . ?
H9C C9 H9F 56.3(16) . . ?
H9D C9 H9E 109.44(15) . . ?
H9D C9 H9F 109.43(15) . . ?
H9E C9 H9F 109.43(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 -0.1(3) 6_557 . . . ?
C1 C1 C2 F2 178.99(17) 6_557 . . . ?
C1 C2 C3 C3 0.1(3) . . . 6_557 ?
C1 C2 C3 F3 179.4(2) . . . . ?
F1 C1 C2 C3 -179.5(2) . . . . ?
F1 C1 C2 F2 -0.4(4) . . . . ?
F2 C2 C3 C3 -179.00(17) . . . 6_557 ?
F2 C2 C3 F3 0.3(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C4 C5 C6 0.3(3) 6_556 . . . ?
C5 C4 C5 C9 -179.97(17) 6_556 . . . ?
C5 C6 C7 C6 0.3(3) . . . 6_556 ?
C5 C6 C7 C8 -179.0(2) . . . . ?
C9 C5 C6 C7 180.0(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-26
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.558
####################################################################### 
# 
# 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_xstr0634_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1518504'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        Hexaflourinebenzene:mesitylene
_chemical_formula_moiety         'C6 F6, C9 H12'
_chemical_formula_sum            'C15 H12 F6'
_chemical_formula_weight         306.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6F6:C6H3C3H9
_chemical_oxdiff_usercomment     
'Single at 190K and at 100K but 150K? Bizarre...'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0737(3)
_cell_length_b                   15.2833(5)
_cell_length_c                   13.2104(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.629(3)
_cell_angle_gamma                90
_cell_volume                     1418.61(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14260
_cell_measurement_temperature    150.04(16)
_cell_measurement_theta_max      73.4320
_cell_measurement_theta_min      4.4280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ovoid
_exptl_crystal_F_000             624
_exptl_crystal_preparation       'Made from 50:50% molar mixture of components'
_exptl_crystal_recrystallization_method 
'Block reduced in size via sublimation at around 240K'
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.277
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0033
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5797
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.636
_diffrn_reflns_theta_min         4.441
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.04(16)
_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 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -10.00   1.00    4.00    --  -42.62 -77.00 -30.00   43
  2  ω    -51.00 -24.00   1.00    4.00    --  -42.62 -77.00 -60.00   27
  3  ω    -73.00 -22.00   1.00    4.00    --  -42.62 -38.00-150.00   51
  4  ω    -70.00  29.00   1.00    4.00    --  -42.62  57.00 -30.00   99
  5  ω    -70.00 -18.00   1.00    4.00    --  -42.62 -38.00  60.00   52
  6  ω    -43.00 -10.00   1.00    4.00    --  -42.62 -77.00 120.00   33
  7  ω      1.00  84.00   1.00    4.00    --   42.62 -99.00  90.00   83
  8  ω     24.00 109.00   1.00   10.00    --  106.36 -94.00  30.00   85
  9  ω     91.00 117.00   1.00   10.00    --  106.36-125.00 -30.00   26
 10  ω     47.00 139.00   1.00   10.00    --  106.36 -77.00-150.00   92
 11  ω     76.00 101.00   1.00   10.00    --  106.36 -94.00-180.00   25
 12  ω     25.00  51.00   1.00   10.00    --  106.36 -94.00-180.00   26
 13  ω     77.00 178.00   1.00   10.00    --  106.36  60.00  32.47  101
 14  ω    140.00 173.00   1.00   10.00    --  106.36  77.00  60.00   33
 15  ω    115.00 143.00   1.00   10.00    --  106.36  55.00 174.48   28
 16  ω     80.00 111.00   1.00   10.00    --  106.36  55.00 174.48   31
 17  ω     77.00 116.00   1.00   10.00    --  106.36  61.00 120.00   39
 18  ω     75.00 135.00   1.00   10.00    --  106.36  77.00  60.00   60
 19  ω     77.00 168.00   1.00   10.00    --  106.36  63.00  99.48   91
 20  ω     78.00 169.00   1.00   10.00    --  106.36  61.00   0.00   91
 21  ω    123.00 177.00   1.00   10.00    --  106.36  77.00-150.00   54
 22  ω    110.00 175.00   1.00   10.00    --  106.36  77.00-180.00   65
 23  ω     77.00 106.00   1.00   10.00    --  106.36  61.00-150.00   29
 24  ω     74.00 100.00   1.00   10.00    --  106.36  77.00-150.00   26
 25  ω     78.00 118.00   1.00   10.00    --  106.36  61.00-120.00   40
 26  ω     77.00 109.00   1.00   10.00    --  106.36  61.00-171.09   32
 27  ω     76.00 123.00   1.00   10.00    --  106.36  68.00-108.39   47
 28  ω     78.00 103.00   1.00   10.00    --  106.36  61.00 -30.00   25
 29  ω     75.00 100.00   1.00   10.00    --  106.36  75.00 -77.52   25
 30  ω     74.00 100.00   1.00   10.00    --  106.36  77.00 -90.00   26
 31  ω     76.00 178.00   1.00   10.00    --  106.36  69.00 -96.14  102
 32  ω     80.00 106.00   1.00   10.00    --  106.36  61.00  60.00   26
 33  ω     75.00 166.00   1.00   10.00    --  106.36  77.00 120.00   91
 34  ω     78.00 105.00   1.00   10.00    --  106.36  58.00 158.25   27
 35  ω     79.00 104.00   1.00   10.00    --  106.36  61.00  90.00   25
 36  ω     74.00 100.00   1.00   10.00    --  106.36  77.00  30.00   26
 37  ω     74.00 100.00   1.00   10.00    --  106.36  77.00   0.00   26
 38  ω     79.00 145.00   1.00   10.00    --  106.36  53.00 -32.09   66
 39  ω     76.00 161.00   1.00   10.00    --  106.36  77.00 -30.00   85
 40  ω     74.00 100.00   1.00   10.00    --  106.36  77.00-180.00   26
 41  ω     43.00 139.00   1.00   10.00    --  106.36 -77.00  90.00   96
 42  ω   -102.00 -74.00   1.00    4.00    --  -42.62 -38.00-150.00   28
 43  ω   -115.00 -10.00   1.00    4.00    --  -42.62 -77.00-150.00  105
 44  ω   -111.00 -12.00   1.00    4.00    --  -42.62 -77.00  60.00   99
 45  ω   -113.00 -62.00   1.00    4.00    --  -42.62-148.00  71.00   51
 46  ω   -118.00 -59.00   1.00    4.00    --  -42.62 -77.00 -30.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0876711000
_diffrn_orient_matrix_UB_12      0.0088950000
_diffrn_orient_matrix_UB_13      0.1009446000
_diffrn_orient_matrix_UB_21      -0.0256819000
_diffrn_orient_matrix_UB_22      -0.1000469000
_diffrn_orient_matrix_UB_23      0.0036640000
_diffrn_orient_matrix_UB_31      0.1992363000
_diffrn_orient_matrix_UB_32      -0.0089407000
_diffrn_orient_matrix_UB_33      0.0597261000
_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                5239
_reflns_number_total             5797
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         5797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.082
_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)+(0.1104P)²+0.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2053
_refine_special_details          'Refined as a 2-component twin., Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.506(2) 0.494(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
3. Others
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5) H13E(0.5) H13F(0.5)
 H15A(0.5) H15B(0.5) H15C(0.5) H15D(0.5) H15F(0.5) H15E(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C12(H12)
4.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13(H13D,H13E,H13F), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C15(H15D,H15F,H15E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0848(3) 0.64092(14) 0.29495(16) 0.0526(5) Uani 1 1 d . . . A 1
C2 C 0.0959(3) 0.64081(16) 0.19296(17) 0.0571(6) Uani 1 1 d . . . A 1
C3 C 0.1307(3) 0.5649(2) 0.1449(2) 0.0727(8) Uani 1 1 d . . . A 1
C4 C 0.1526(3) 0.4877(2) 0.2005(3) 0.0876(11) Uani 1 1 d . . . A 1
C5 C 0.1408(4) 0.48952(19) 0.3037(3) 0.0816(9) Uani 1 1 d . . . A 1
C6 C 0.1075(3) 0.56600(18) 0.3506(2) 0.0654(6) Uani 1 1 d . . . A 1
F1 F 0.0530(2) 0.71595(10) 0.34251(12) 0.0787(5) Uani 1 1 d . . . A 1
F2 F 0.0750(3) 0.71568(12) 0.14153(13) 0.0932(6) Uani 1 1 d . . . A 1
F3 F 0.1449(3) 0.56530(18) 0.04523(14) 0.1225(9) Uani 1 1 d . . . A 1
F4 F 0.1868(3) 0.41322(15) 0.1533(3) 0.1548(13) Uani 1 1 d . . . A 1
F5 F 0.1647(4) 0.41519(13) 0.3571(3) 0.1477(12) Uani 1 1 d . . . A 1
F6 F 0.0982(3) 0.56854(15) 0.45058(14) 0.1069(7) Uani 1 1 d . . . A 1
C7 C 0.4118(3) 0.36297(14) 0.66629(17) 0.0509(5) Uani 1 1 d . . . B 2
C8 C 0.3793(3) 0.45249(14) 0.66208(17) 0.0533(5) Uani 1 1 d . . . B 2
H8 H 0.3719 0.4816 0.5982 0.064 Uiso 1 1 calc R . . B 2
C9 C 0.3575(3) 0.50045(13) 0.74955(18) 0.0529(5) Uani 1 1 d . . . B 2
C10 C 0.3686(3) 0.45683(14) 0.84185(17) 0.0513(5) Uani 1 1 d . . . B 2
H10 H 0.3536 0.4889 0.9020 0.062 Uiso 1 1 calc R . . B 2
C11 C 0.4011(3) 0.36743(14) 0.84851(16) 0.0502(5) Uani 1 1 d . . . B 2
C12 C 0.4227(3) 0.32206(12) 0.75989(16) 0.0496(5) Uani 1 1 d . . . B 2
H12 H 0.4457 0.2608 0.7636 0.059 Uiso 1 1 calc R . . B 2
C13 C 0.4341(4) 0.3115(2) 0.5706(2) 0.0811(8) Uani 1 1 d . . . B 2
H13A H 0.4613 0.3518 0.5163 0.122 Uiso 0.5 1 calc GR . P B 2
H13B H 0.3161 0.2796 0.5491 0.122 Uiso 0.5 1 calc GR . P B 2
H13C H 0.5393 0.2699 0.5843 0.122 Uiso 0.5 1 calc GR . P B 2
H13D H 0.4267 0.2488 0.5850 0.122 Uiso 0.5 1 calc GR . P B 2
H13E H 0.5578 0.3249 0.5476 0.122 Uiso 0.5 1 calc GR . P B 2
H13F H 0.3322 0.3276 0.5171 0.122 Uiso 0.5 1 calc GR . P B 2
C14 C 0.3246(5) 0.59765(16) 0.7439(3) 0.0890(10) Uani 1 1 d . . . B 2
H14A H 0.2612 0.6165 0.8023 0.133 Uiso 1 1 calc GR . . B 2
H14B H 0.2443 0.6119 0.6806 0.133 Uiso 1 1 calc GR . . B 2
H14C H 0.4471 0.6279 0.7450 0.133 Uiso 1 1 calc GR . . B 2
C15 C 0.4131(5) 0.3203(2) 0.9495(2) 0.0832(9) Uani 1 1 d . . . B 2
H15A H 0.3141 0.3425 0.9889 0.125 Uiso 0.5 1 calc GR . P B 2
H15B H 0.5385 0.3304 0.9876 0.125 Uiso 0.5 1 calc GR . P B 2
H15C H 0.3945 0.2574 0.9377 0.125 Uiso 0.5 1 calc GR . P B 2
H15D H 0.5069 0.2730 0.9506 0.125 Uiso 0.5 1 calc GR . P B 2
H15F H 0.2883 0.2957 0.9588 0.125 Uiso 0.5 1 calc GR . P B 2
H15E H 0.4520 0.3616 1.0048 0.125 Uiso 0.5 1 calc GR . P 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
C1 C2 1.359(3) . ?
C1 C6 1.360(3) . ?
C1 F1 1.339(3) . ?
C2 C3 1.359(4) . ?
C2 F2 1.330(3) . ?
C3 C4 1.390(5) . ?
C3 F3 1.332(3) . ?
C4 C5 1.376(5) . ?
C4 F4 1.333(3) . ?
C5 C6 1.356(4) . ?
C5 F5 1.337(3) . ?
C6 F6 1.331(3) . ?
C7 C8 1.387(3) . ?
C7 C12 1.380(3) . ?
C7 C13 1.512(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(3) . ?
C9 C10 1.384(3) . ?
C9 C14 1.504(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 C12 1.384(3) . ?
C11 C15 1.510(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15D 0.9800 . ?
C15 H15F 0.9800 . ?
C15 H15E 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 C6 121.2(2) . . ?
F1 C1 C2 119.9(2) . . ?
F1 C1 C6 118.9(2) . . ?
C1 C2 C3 119.9(2) . . ?
F2 C2 C1 119.3(2) . . ?
F2 C2 C3 120.7(2) . . ?
C2 C3 C4 119.5(3) . . ?
F3 C3 C2 119.8(3) . . ?
F3 C3 C4 120.7(3) . . ?
C5 C4 C3 119.4(2) . . ?
F4 C4 C3 119.5(4) . . ?
F4 C4 C5 121.1(4) . . ?
C6 C5 C4 120.2(3) . . ?
F5 C5 C4 119.1(3) . . ?
F5 C5 C6 120.6(3) . . ?
C5 C6 C1 119.7(3) . . ?
F6 C6 C1 119.7(3) . . ?
F6 C6 C5 120.6(3) . . ?
C8 C7 C13 120.8(2) . . ?
C12 C7 C8 118.34(19) . . ?
C12 C7 C13 120.9(2) . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.3(2) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C14 120.7(2) . . ?
C10 C9 C8 118.51(19) . . ?
C10 C9 C14 120.8(2) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.51(19) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C15 121.2(2) . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 C15 120.5(2) . . ?
C7 C12 C11 122.06(19) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
C7 C13 H13D 109.5 . . ?
C7 C13 H13E 109.5 . . ?
C7 C13 H13F 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13A C13 H13D 140.8 . . ?
H13A C13 H13E 52.1 . . ?
H13A C13 H13F 60.4 . . ?
H13B C13 H13C 109.5 . . ?
H13B C13 H13D 60.4 . . ?
H13B C13 H13E 140.8 . . ?
H13B C13 H13F 52.1 . . ?
H13C C13 H13D 52.1 . . ?
H13C C13 H13E 60.4 . . ?
H13C C13 H13F 140.8 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
C11 C15 H15D 109.5 . . ?
C11 C15 H15F 109.5 . . ?
C11 C15 H15E 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15A C15 H15D 140.5 . . ?
H15A C15 H15F 50.0 . . ?
H15A C15 H15E 62.5 . . ?
H15B C15 H15C 109.5 . . ?
H15B C15 H15D 62.5 . . ?
H15B C15 H15F 140.5 . . ?
H15B C15 H15E 50.0 . . ?
H15C C15 H15D 50.0 . . ?
H15C C15 H15F 62.5 . . ?
H15C C15 H15E 140.5 . . ?
H15D C15 H15F 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15F C15 H15E 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
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C2 C3 F3 -178.8(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 F6 179.1(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 F4 180.0(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 F5 -179.1(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 F6 -179.1(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C1 C2 F2 -179.3(2) . . . . ?
F1 C1 C2 C3 179.1(2) . . . . ?
F1 C1 C2 F2 0.1(3) . . . . ?
F1 C1 C6 C5 -179.6(2) . . . . ?
F1 C1 C6 F6 -0.2(3) . . . . ?
F2 C2 C3 C4 179.8(2) . . . . ?
F2 C2 C3 F3 0.2(4) . . . . ?
F3 C3 C4 C5 178.8(2) . . . . ?
F3 C3 C4 F4 -0.5(4) . . . . ?
F4 C4 C5 C6 179.5(2) . . . . ?
F4 C4 C5 F5 0.2(4) . . . . ?
F5 C5 C6 C1 179.6(2) . . . . ?
F5 C5 C6 F6 0.1(4) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C14 179.3(2) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C10 C11 C15 180.0(2) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
C13 C7 C8 C9 179.6(2) . . . . ?
C13 C7 C12 C11 -179.4(2) . . . . ?
C14 C9 C10 C11 -179.2(2) . . . . ?
C15 C11 C12 C7 179.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 
'20um nylon Hampton Research 0.9mm diameter 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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.773
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.506(2) 16130 5103 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.494(2) 16101 5103 nmt 0.9996 0.0000 0.1237 0.0001 -1.0000 0.0000 -0.0003
-0.0001 -1.0000

_twin_special_details            
;
Component 2 rotated by -179.9964° 
 around [1.00 0.00 -0.00] (reciprocal) or [1.00 0.00 0.06] (direct)
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0591b_new
_database_code_depnum_ccdc_archive 'CCDC 1518505'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F6, C9 H12'
_chemical_formula_sum            'C15 H12 F6'
_chemical_formula_weight         306.25
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 F6 C9 H12'
_chemical_oxdiff_usercomment     'C6F6:C6H3Me3 (1,3,5) 50:50 at 100K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           -1
_space_group_name_H-M_alt        'P b 21 a'
_space_group_name_Hall           'P -2ac -2abu'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'-x+3/4, y+1/2, z'

_cell_length_a                   13.93854(8)
_cell_length_b                   15.18032(8)
_cell_length_c                   13.14822(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2782.05(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    35030
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.2920
_cell_measurement_theta_min      3.1660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 -7 0.2161
5 -8 1 0.3747
-5 5 5 0.3115
0 8 -5 0.2924
0 8 5 0.1816
5 1 -7 0.3966
-5 -4 6 0.3625
-5 3 -7 0.1851
8 5 -3 0.4515
-7 2 -6 0.2065
7 -6 0 0.4010
5 -3 7 0.3325
6 4 5 0.3480
4 2 8 0.2815
-2 0 -8 0.1765
9 -2 0 0.4596
9 1 -2 0.4689
4 -7 -4 0.3452
6 5 -5 0.4262
0 10 1 0.1986
6 -2 6 0.3674
1 9 4 0.1964
9 2 1 0.4694
-1 0 8 0.2422
-3 4 -7 0.2084
-1 -6 7 0.3314
1 -5 7 0.2900
5 -7 4 0.3554
-2 6 6 0.2135
-2 -7 5 0.3754
-6 -7 3 0.3971
8 -4 2 0.4404
-8 -4 2 0.3958
3 -4 7 0.2963
-1 4 8 0.2167
4 -3 -7 0.3386
6 -6 3 0.3910
-3 -1 -8 0.1680
3 4 7 0.2316
-5 7 -4 0.2405
2 1 -8 0.2967
1 6 7 0.2032
8 -3 -2 0.4510
-7 -6 3 0.3970
0 1 8 0.2280
-9 -2 -2 0.3363
1 -8 5 0.3607
2 0 8 0.2499
8 2 -4 0.4483
-4 -8 3 0.3879
-4 -8 -3 0.3517
6 -4 -6 0.3793
-1 1 -8 0.2123
-1 -2 8 0.2668
-3 -4 -7 0.1918
5 3 7 0.3104
2 9 3 0.2250
2 3 8 0.2267
5 -6 -5 0.3593
0 -1 -8 0.2297
1 -3 -8 0.2516
-3 7 -5 0.2302
-2 -6 -6 0.2317
-3 8 4 0.2459
3 9 1 0.3060
7 -1 5 0.3973
8 0 3 0.4403
3 -5 -7 0.2953
-3 4 7 0.2684
-7 5 -3 0.2707
-4 -9 0 0.3793
-1 -9 -4 0.3022
0 -8 -5 0.2738
-9 -1 2 0.3901
-1 -10 0 0.3654
-1 9 2 0.2121
-4 -2 -7 0.1739
3 -9 -3 0.3343
4 5 6 0.2555
1 -10 -2 0.3392
-8 0 -4 0.2804
0 -1 8 0.2510
-1 -3 -8 0.1805
-3 1 8 0.2529
8 1 -4 0.4548
1 -7 -6 0.2714
0 5 -7 0.2608
0 -2 -8 0.2021
3 -7 5 0.3445
3 7 5 0.2335

_exptl_crystal_size_max          0.873
_exptl_crystal_size_mid          0.615
_exptl_crystal_size_min          0.408
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
-0.2873 -4.9037 -7.3922 -0.9532 0.2460 -0.1756
5.3067 -7.9205 0.8463 -0.5470 -0.8274 0.1273
-5.4572 4.8000 5.3936 0.8165 0.3551 0.4552
0.4564 7.6871 -5.3255 0.1399 0.5814 -0.8015
0.2336 8.1732 4.7537 0.9842 0.0438 -0.1717
5.3391 1.0815 -6.8334 -0.4960 -0.0210 -0.8681
-5.1317 -3.5921 6.3116 0.2673 -0.0700 0.9611
-4.5922 3.4729 -6.7064 -0.2552 0.9189 -0.3009
7.5265 4.5593 -2.6340 0.0858 -0.3054 -0.9484
-6.6141 1.9282 -5.5736 -0.2679 0.9635 -0.0011
6.8173 -6.4652 -0.3842 -0.5460 -0.8263 -0.1380
4.7174 -3.3944 6.6590 0.2565 -0.9237 0.2847
6.2518 4.0426 5.0708 0.6714 -0.6584 -0.3401
3.9720 1.7588 7.5086 0.7099 -0.6969 0.1021
-2.0653 -0.0834 -8.3049 -0.6600 0.6483 -0.3797
8.7506 -2.4907 0.3035 -0.2073 -0.8677 -0.4519
8.7973 0.7410 -1.9121 -0.1458 -0.6122 -0.7772
3.9347 -7.3817 -4.2627 -0.9088 -0.3957 -0.1323
5.6821 5.4831 -4.6546 0.0023 0.0058 -1.0000
-0.3216 9.7436 1.2200 0.8204 0.3580 -0.4458
6.3311 -2.1879 5.7899 0.2675 -0.9623 0.0492
0.9920 8.6434 3.9800 0.9529 0.0426 -0.3002
8.7368 2.4088 0.7753 0.1931 -0.6922 -0.6954
-1.4259 -0.1289 8.4273 0.6730 -0.3656 0.6430
-2.9151 4.3704 -7.1359 -0.2322 0.8370 -0.4955
-1.0719 -5.5985 6.9534 0.1483 -0.5362 0.8310
1.4260 -4.9648 7.2481 0.2053 -0.7405 0.6399
5.1990 -6.7692 3.7945 -0.2252 -0.9396 0.2579
-1.5913 6.4664 6.2579 0.9882 0.0436 0.1470
-2.2977 -7.2753 5.3383 -0.0985 -0.4079 0.9077
-5.8628 -6.7741 2.8124 -0.2444 0.0620 0.9677
7.8962 -4.3780 1.7296 -0.2281 -0.9538 -0.1957
-8.0780 -4.0163 1.6612 -0.1205 0.4305 0.8945
3.0269 -4.3186 7.1180 0.2340 -0.8434 0.4837
-0.6711 3.7936 7.8477 0.9127 -0.2358 0.3337
4.0498 -2.5821 -7.2990 -0.7974 -0.0347 -0.6025
6.4528 -5.9509 3.0350 -0.2322 -0.9697 0.0762
-2.6440 -0.5771 -8.1418 -0.6803 0.6681 -0.3013
2.5161 4.0006 7.4225 0.8768 -0.4754 0.0726
-5.1755 6.7815 -3.8066 0.2250 0.9388 -0.2610
2.1144 0.9078 -8.2626 -0.6058 0.3293 -0.7242
1.2146 5.8599 6.7578 0.9682 -0.2497 0.0170
8.2535 -2.9563 -2.3970 -0.4553 -0.6898 -0.5629
-6.5008 -5.7995 3.1782 -0.1395 0.1356 0.9809
-0.0270 1.3999 8.4453 0.7800 -0.4234 0.4609
-8.7189 -1.6448 -1.7826 -0.2173 0.7797 0.5872
1.0710 -7.7777 5.1433 -0.1695 -0.7053 0.6883
1.9967 0.0257 8.3202 0.6573 -0.6456 0.3887
7.7335 1.9393 -4.1138 -0.2277 -0.3460 -0.9102
-3.8039 -8.4093 2.6387 -0.3904 -0.1713 0.9046
-4.4061 -8.0155 -2.7034 -0.7858 0.2020 0.5846
5.7825 -3.9496 -5.6067 -0.7724 -0.3358 -0.5391
-0.6979 1.0394 -8.4596 -0.5967 0.5863 -0.5479
-1.1859 -2.4937 8.1821 0.4770 -0.4692 0.7432
-3.0341 -4.4984 -7.0254 -0.8790 0.4765 0.0167
5.1942 2.9260 6.5042 0.7093 -0.6959 -0.1125
1.8109 8.9874 3.0426 0.8989 0.0403 -0.4363
1.5731 3.0645 7.9689 0.8563 -0.4645 0.2256
5.0067 -5.7473 -5.0765 -0.8588 -0.3736 -0.3505
0.3139 -1.0920 -8.4747 -0.7611 0.4132 -0.5000
1.2009 -3.1266 -8.0115 -0.8793 0.2273 -0.4185
-3.3330 7.4807 -4.5789 0.2049 0.8542 -0.4779
-1.6629 -6.2789 -6.3797 -0.9665 0.2492 0.0619
-3.3330 8.0506 3.7822 0.9166 0.3992 0.0222
3.4292 9.0678 0.8175 0.7179 0.0326 -0.6954
7.3145 -1.1898 4.9110 0.2657 -0.9551 -0.1313
8.3386 0.3789 3.2921 0.2466 -0.8856 -0.3937
2.9648 -4.5829 -7.0177 -0.9171 -0.0402 -0.3967
-3.4315 3.7918 7.1819 0.8742 0.0382 0.4841
-7.0957 5.3677 -2.5338 0.2327 0.9720 0.0332
-3.6446 -9.0012 -0.4732 -0.6843 -0.0311 0.7286
-1.1244 -8.7109 -3.8358 -0.9457 -0.0423 0.3224
-0.0885 -8.0673 -4.8919 -0.9882 -0.0440 0.1469
-8.8241 -0.6190 1.8331 0.1487 0.6240 0.7672
-1.1499 -9.7718 0.1083 -0.7082 -0.3093 0.6346
-1.4952 9.3631 2.2451 0.8807 0.3840 -0.2774
-4.3079 -2.0705 -7.2805 -0.7129 0.6997 -0.0467
2.6841 -8.6266 -3.2502 -0.9131 -0.3979 0.0892
3.7379 5.1524 6.3545 0.8699 -0.4714 -0.1452
1.0749 -9.5367 -1.8815 -0.8622 -0.3760 0.3396
-8.0150 0.2269 -3.9500 -0.2562 0.9204 0.2953
0.4537 -1.2339 8.4551 0.5833 -0.5732 0.5755
-1.4500 -2.9397 -8.0249 -0.8523 0.4623 -0.2448
-2.6205 1.1332 8.1106 0.7474 -0.1935 0.6355
8.0917 0.7148 -3.7830 -0.2937 -0.4459 -0.8455
1.2899 -6.8060 -6.0454 -0.9947 -0.0440 -0.0934
-0.4399 5.2677 -7.2018 -0.1845 0.6660 -0.7228
-0.4806 -1.9378 -8.3520 -0.8096 0.4393 -0.3894
3.4562 -7.4483 4.5370 -0.2065 -0.8610 0.4648
2.7810 7.1853 5.2083 0.9337 -0.2405 -0.2652

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43732
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.753
_diffrn_reflns_theta_min         4.623
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -18.00   1.00    1.00    --  -42.62 -38.00 -30.00   74
  2  ω     24.00  51.00   1.00    1.00    --   42.62-125.00-150.00   27
  3  ω     31.00  56.00   1.00    1.00    --  106.36 -30.00-180.00   25
  4  ω     52.00  85.00   1.00    1.00    --  106.36 -30.00-120.00   33
  5  ω     41.00  67.00   1.00    1.00    --  106.36 -30.00  30.00   26
  6  ω     55.00 141.00   1.00    1.00    --  106.36  15.00  60.00   86
  7  ω     83.00 164.00   1.00    1.00    --  106.36  45.00  90.00   81
  8  ω     51.00  79.00   1.00    1.00    --  106.36 -30.00 120.00   28
  9  ω    -68.00  -4.00   1.00    1.00    --  -42.62 125.00  60.00   64
 10  ω   -117.00 -10.00   1.00    1.00    --  -42.87 -77.00 120.00  107
 11  ω    -40.00  28.00   1.00    1.00    --  -42.87  38.00 -90.00   68
 12  ω   -119.00 -93.00   1.00    1.00    --  -42.87 -77.00  30.00   26
 13  ω   -116.00 -85.00   1.00    1.00    --  -42.87 -77.00-150.00   31
 14  ω   -115.00 -50.00   1.00    1.00    --  -42.87 -19.00-150.00   65
 15  ω    -58.00 -10.00   1.00    1.00    --  -42.87 -77.00-150.00   48
 16  ω    -61.00 -22.00   1.00    1.00    --  -42.87 -38.00 150.00   39
 17  ω   -117.00 -92.00   1.00    1.00    --  -42.87 -38.00 150.00   25
 18  ω    -30.00  -3.00   1.00    1.00    --  -42.87 -19.00-150.00   27
 19  ω   -123.00 -84.00   1.00    1.00    --  -42.87 -99.00   0.00   39
 20  ω    -52.00 -10.00   1.00    1.00    --  -42.87 -77.00  30.00   42
 21  ω   -103.00 -10.00   1.00    1.00    --  -42.87 -77.00 -60.00   93
 22  ω      4.00  75.00   1.00    1.00    --   42.87 -99.00   0.00   71
 23  ω     53.00  93.00   1.00    1.00    --   42.87-125.00 -60.00   40
 24  ω    126.00 162.00   1.00    1.00    --  106.36  77.00  30.00   36
 25  ω     74.00 100.00   1.00    1.00    --  106.36  77.00  30.00   26
 26  ω     74.00 155.00   1.00    1.00    --  106.36  76.00-101.90   81
 27  ω    118.00 144.00   1.00    1.00    --  106.36  61.00-150.00   26
 28  ω     77.00 106.00   1.00    1.00    --  106.36  61.00-150.00   29
 29  ω     76.00 102.00   1.00    1.00    --  106.36  67.00 122.18   26
 30  ω    150.00 176.00   1.00    1.00    --  106.36  68.00 -24.91   26
 31  ω     77.00 102.00   1.00    1.00    --  106.36  61.00  90.00   25
 32  ω     74.00  99.00   1.00    1.00    --  106.36  77.00 -90.00   25
 33  ω     77.00 103.00   1.00    1.00    --  106.36  61.00   0.00   26
 34  ω     77.00 103.00   1.00    1.00    --  106.36  61.00 -30.00   26
 35  ω     74.00 100.00   1.00    1.00    --  106.36  77.00-150.00   26
 36  ω     33.00 121.00   1.00    1.00    --  106.36-125.00 120.00   88
 37  ω     74.00  99.00   1.00    1.00    --  106.36  77.00-120.00   25
 38  ω    112.00 177.00   1.00    1.00    --  106.36  77.00-180.00   65
 39  ω     77.00 102.00   1.00    1.00    --  106.36  61.00-180.00   25
 40  ω     77.00 103.00   1.00    1.00    --  106.36  60.00 170.60   26
 41  ω     74.00 100.00   1.00    1.00    --  106.36  77.00-180.00   26
 42  ω     74.00  99.00   1.00    1.00    --  106.36  76.00  92.00   25
 43  ω     77.00 170.00   1.00    1.00    --  106.36  61.00 150.00   93
 44  ω     74.00 100.00   1.00    1.00    --  106.36  77.00 -60.00   26
 45  ω     77.00 103.00   1.00    1.00    --  106.36  61.00  30.00   26
 46  ω     30.00 139.00   1.00    1.00    --  106.36 -77.00 -90.00  109
 47  ω     77.00 103.00   1.00    1.00    --  106.36  61.00  60.00   26
 48  ω     77.00 154.00   1.00    1.00    --  106.36  61.00-120.00   77
 49  ω     74.00 100.00   1.00    1.00    --  106.36  77.00  60.00   26
 50  ω     77.00 103.00   1.00    1.00    --  106.36  61.00 120.00   26
 51  ω     74.00  99.00   1.00    1.00    --  106.36  77.00   0.00   25
 52  ω     74.00 129.00   1.00    1.00    --  106.36  77.00 120.00   55
 53  ω    135.00 172.00   1.00    1.00    --  106.36  77.00 120.00   37
 54  ω     30.00 139.00   1.00    1.00    --  106.36 -77.00 120.00  109
 55  ω     84.00 109.00   1.00    1.00    --  106.36 -94.00-150.00   25
 56  ω     76.00 173.00   1.00    1.00    --  106.36  67.00 -59.16   97
 57  ω     76.00 101.00   1.00    1.00    --  106.36  68.00 -24.91   25
 58  ω     78.00 103.00   1.00    1.00    --  106.36  58.00-103.80   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054030340
_diffrn_orient_matrix_UB_12      0.0739974710
_diffrn_orient_matrix_UB_13      0.0800715634
_diffrn_orient_matrix_UB_21      -0.0854789139
_diffrn_orient_matrix_UB_22      0.0410792472
_diffrn_orient_matrix_UB_23      -0.0572119310
_diffrn_orient_matrix_UB_31      -0.0697916039
_diffrn_orient_matrix_UB_32      -0.0560285338
_diffrn_orient_matrix_UB_33      0.0636381643
_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         0.913
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                5511
_reflns_number_total             5558
_reflns_odcompleteness_completeness 99.65
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.442(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.081
_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)+(0.0583P)²+0.5965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C10A(H10A), C12A(H12A), C8B(H8B), C10B(H10B), C12B(H12B)
2.b Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C15A(H15A,H15B,H15C), C13B(H13D,
 H13E,H13F), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.54071(16) 0.61404(16) 0.30814(19) 0.0296(5) Uani 1 1 d . . . A 1
C2A C 0.55185(17) 0.54001(18) 0.36694(18) 0.0336(5) Uani 1 1 d . . . A 1
C3A C 0.5713(2) 0.46028(18) 0.3228(2) 0.0404(6) Uani 1 1 d . . . A 1
C4A C 0.57984(18) 0.4545(2) 0.2190(3) 0.0435(7) Uani 1 1 d . . . A 1
C5A C 0.56924(17) 0.5282(2) 0.15929(19) 0.0387(6) Uani 1 1 d . . . A 1
C6A C 0.54937(18) 0.60855(18) 0.20434(18) 0.0328(5) Uani 1 1 d . . . A 1
F1A F 0.52326(12) 0.69175(10) 0.35203(12) 0.0427(4) Uani 1 1 d . . . A 1
F2A F 0.54425(13) 0.54689(13) 0.46846(11) 0.0507(4) Uani 1 1 d . . . A 1
F3A F 0.58129(15) 0.38831(12) 0.38116(18) 0.0678(6) Uani 1 1 d . . . A 1
F4A F 0.59866(13) 0.37648(13) 0.17627(19) 0.0673(6) Uani 1 1 d . . . A 1
F5A F 0.57942(13) 0.52329(16) 0.05857(12) 0.0621(6) Uani 1 1 d . . . A 1
F6A F 0.53963(14) 0.68081(13) 0.14742(13) 0.0537(5) Uani 1 1 d . . . A 1
C1B C 0.45948(16) 0.32603(17) 0.84174(18) 0.0294(5) Uani 1 1 d . . . B 2
C2B C 0.45800(18) 0.3356(2) 0.73703(19) 0.0336(5) Uani 1 1 d . . . B 2
C3B C 0.43837(18) 0.4170(2) 0.6960(2) 0.0438(7) Uani 1 1 d . . . B 2
C4B C 0.42122(19) 0.4886(2) 0.7585(3) 0.0467(8) Uani 1 1 d . . . B 2
C5B C 0.42258(18) 0.47802(19) 0.8620(3) 0.0424(6) Uani 1 1 d . . . B 2
C6B C 0.44149(17) 0.39714(18) 0.90349(19) 0.0335(5) Uani 1 1 d . . . B 2
F1B F 0.47691(12) 0.24718(10) 0.88237(12) 0.0431(4) Uani 1 1 d . . . B 2
F2B F 0.47326(13) 0.26615(13) 0.67801(13) 0.0512(4) Uani 1 1 d . . . B 2
F3B F 0.43581(13) 0.42643(18) 0.59554(14) 0.0685(7) Uani 1 1 d . . . B 2
F4B F 0.40183(14) 0.56708(14) 0.7186(2) 0.0734(7) Uani 1 1 d . . . B 2
F5B F 0.40361(14) 0.54659(12) 0.92387(18) 0.0652(6) Uani 1 1 d . . . B 2
F6B F 0.44080(12) 0.38602(13) 1.00522(11) 0.0484(4) Uani 1 1 d . . . B 2
C7A C 0.29931(16) 0.60105(17) 0.38048(18) 0.0294(5) Uani 1 1 d . . . C 3
C8A C 0.31760(15) 0.51126(16) 0.37130(19) 0.0294(5) Uani 1 1 d . . . C 3
H8A H 0.3265 0.4778 0.4298 0.035 Uiso 1 1 calc R . . C 3
C9A C 0.32281(16) 0.47046(16) 0.2769(2) 0.0291(5) Uani 1 1 d . . . C 3
C10A C 0.31044(15) 0.52141(15) 0.18996(18) 0.0276(5) Uani 1 1 d . . . C 3
H10A H 0.3147 0.4949 0.1264 0.033 Uiso 1 1 calc R . . C 3
C11A C 0.29178(15) 0.61142(16) 0.19624(19) 0.0282(5) Uani 1 1 d . . . C 3
C12A C 0.28659(16) 0.65001(16) 0.29177(19) 0.0286(5) Uani 1 1 d . . . C 3
H12A H 0.2743 0.7101 0.2967 0.034 Uiso 1 1 calc R . . C 3
C13A C 0.2939(2) 0.6441(2) 0.4835(2) 0.0454(6) Uani 1 1 d . . . C 3
H13A H 0.2397 0.6212 0.5201 0.068 Uiso 1 1 calc GR . . C 3
H13B H 0.2869 0.7066 0.4754 0.068 Uiso 1 1 calc GR . . C 3
H13C H 0.3516 0.6318 0.5208 0.068 Uiso 1 1 calc GR . . C 3
C14A C 0.3406(2) 0.37267(17) 0.2676(2) 0.0423(6) Uani 1 1 d . . . C 3
H14A H 0.3631 0.3501 0.3315 0.063 Uiso 1 1 calc GR . . C 3
H14B H 0.3881 0.3622 0.2161 0.063 Uiso 1 1 calc GR . . C 3
H14C H 0.2820 0.3435 0.2493 0.063 Uiso 1 1 calc GR . . C 3
C15A C 0.2793(2) 0.66597(19) 0.1015(2) 0.0397(6) Uani 1 1 d . . . C 3
H15A H 0.2403 0.7164 0.1165 0.059 Uiso 1 1 calc GR . . C 3
H15B H 0.2487 0.6312 0.0499 0.059 Uiso 1 1 calc GR . . C 3
H15C H 0.3409 0.6851 0.0776 0.059 Uiso 1 1 calc GR . . C 3
C7B C 0.20553(16) 0.33172(17) 0.84051(18) 0.0295(5) Uani 1 1 d . . . D 4
C8B C 0.21552(16) 0.29422(16) 0.74448(18) 0.0282(5) Uani 1 1 d . . . D 4
H8B H 0.2297 0.2345 0.7392 0.034 Uiso 1 1 calc R . . D 4
C9B C 0.20485(16) 0.34385(16) 0.65615(18) 0.0294(5) Uani 1 1 d . . . D 4
C10B C 0.18480(16) 0.43345(16) 0.66540(18) 0.0302(5) Uani 1 1 d . . . D 4
H10B H 0.1779 0.4675 0.6070 0.036 Uiso 1 1 calc R . . D 4
C11B C 0.17491(16) 0.47297(16) 0.7604(2) 0.0305(5) Uani 1 1 d . . . D 4
C12B C 0.18529(16) 0.42145(17) 0.84695(19) 0.0309(5) Uani 1 1 d . . . D 4
H12B H 0.1786 0.4474 0.9106 0.037 Uiso 1 1 calc R . . D 4
C13B C 0.2157(2) 0.2766(2) 0.9351(2) 0.0447(6) Uani 1 1 d . . . D 4
H13D H 0.2316 0.3140 0.9916 0.067 Uiso 1 1 calc GR . . D 4
H13E H 0.2657 0.2340 0.9253 0.067 Uiso 1 1 calc GR . . D 4
H13F H 0.1563 0.2469 0.9486 0.067 Uiso 1 1 calc GR . . D 4
C14B C 0.2153(2) 0.3013(2) 0.5532(2) 0.0452(6) Uani 1 1 d . . . D 4
H14D H 0.1783 0.3336 0.5042 0.068 Uiso 1 1 calc GR . . D 4
H14E H 0.1926 0.2417 0.5564 0.068 Uiso 1 1 calc GR . . D 4
H14F H 0.2816 0.3016 0.5335 0.068 Uiso 1 1 calc GR . . D 4
C15B C 0.1544(2) 0.57048(18) 0.7688(3) 0.0481(7) Uani 1 1 d . . . D 4
H15D H 0.2136 0.6020 0.7768 0.072 Uiso 1 1 calc GR . . D 4
H15E H 0.1141 0.5811 0.8268 0.072 Uiso 1 1 calc GR . . D 4
H15F H 0.1224 0.5903 0.7083 0.072 Uiso 1 1 calc GR . . D 4


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.373(3) . ?
C1A C6A 1.373(4) . ?
C1A F1A 1.336(3) . ?
C2A C3A 1.370(4) . ?
C2A F2A 1.343(3) . ?
C3A C4A 1.372(5) . ?
C3A F3A 1.342(3) . ?
C4A C5A 1.375(5) . ?
C4A F4A 1.337(3) . ?
C5A C6A 1.384(4) . ?
C5A F5A 1.334(3) . ?
C6A F6A 1.335(3) . ?
C1B C2B 1.385(4) . ?
C1B C6B 1.374(4) . ?
C1B F1B 1.333(3) . ?
C2B C3B 1.375(4) . ?
C2B F2B 1.326(3) . ?
C3B C4B 1.383(5) . ?
C3B F3B 1.329(3) . ?
C4B C5B 1.371(5) . ?
C4B F4B 1.330(3) . ?
C5B C6B 1.369(4) . ?
C5B F5B 1.347(3) . ?
C6B F6B 1.348(3) . ?
C7A C8A 1.392(3) . ?
C7A C12A 1.394(3) . ?
C7A C13A 1.506(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.389(4) . ?
C9A C10A 1.391(4) . ?
C9A C14A 1.510(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.393(3) . ?
C11A C12A 1.388(4) . ?
C11A C15A 1.506(3) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C7B C8B 1.392(3) . ?
C7B C12B 1.394(4) . ?
C7B C13B 1.505(3) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.392(3) . ?
C9B C10B 1.394(3) . ?
C9B C14B 1.506(3) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.392(4) . ?
C11B C12B 1.389(4) . ?
C11B C15B 1.512(4) . ?
C12B H12B 0.9300 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6A C1A C2A 120.0(2) . . ?
F1A C1A C2A 120.0(2) . . ?
F1A C1A C6A 119.9(2) . . ?
C3A C2A C1A 120.5(2) . . ?
F2A C2A C1A 119.1(2) . . ?
F2A C2A C3A 120.4(2) . . ?
C2A C3A C4A 119.7(2) . . ?
F3A C3A C2A 119.8(3) . . ?
F3A C3A C4A 120.5(3) . . ?
C3A C4A C5A 120.4(2) . . ?
F4A C4A C3A 119.5(3) . . ?
F4A C4A C5A 120.1(3) . . ?
C4A C5A C6A 119.6(2) . . ?
F5A C5A C4A 120.7(3) . . ?
F5A C5A C6A 119.7(3) . . ?
C1A C6A C5A 119.8(2) . . ?
F6A C6A C1A 119.9(2) . . ?
F6A C6A C5A 120.3(2) . . ?
C6B C1B C2B 120.2(2) . . ?
F1B C1B C2B 119.7(2) . . ?
F1B C1B C6B 120.1(2) . . ?
C3B C2B C1B 119.2(3) . . ?
F2B C2B C1B 119.7(3) . . ?
F2B C2B C3B 121.1(2) . . ?
C2B C3B C4B 120.4(3) . . ?
F3B C3B C2B 119.5(3) . . ?
F3B C3B C4B 120.0(3) . . ?
C5B C4B C3B 119.7(3) . . ?
F4B C4B C3B 120.3(3) . . ?
F4B C4B C5B 119.9(3) . . ?
C6B C5B C4B 120.2(3) . . ?
F5B C5B C4B 120.4(3) . . ?
F5B C5B C6B 119.4(3) . . ?
C5B C6B C1B 120.3(2) . . ?
F6B C6B C1B 119.3(2) . . ?
F6B C6B C5B 120.4(2) . . ?
C8A C7A C12A 118.2(2) . . ?
C8A C7A C13A 120.8(2) . . ?
C12A C7A C13A 121.0(2) . . ?
C7A C8A H8A 119.2 . . ?
C9A C8A C7A 121.6(2) . . ?
C9A C8A H8A 119.2 . . ?
C8A C9A C10A 118.7(2) . . ?
C8A C9A C14A 121.3(2) . . ?
C10A C9A C14A 120.0(2) . . ?
C9A C10A H10A 119.3 . . ?
C9A C10A C11A 121.3(2) . . ?
C11A C10A H10A 119.3 . . ?
C10A C11A C15A 120.8(2) . . ?
C12A C11A C10A 118.5(2) . . ?
C12A C11A C15A 120.7(2) . . ?
C7A C12A H12A 119.2 . . ?
C11A C12A C7A 121.7(2) . . ?
C11A C12A H12A 119.2 . . ?
C7A C13A H13A 109.5 . . ?
C7A C13A H13B 109.5 . . ?
C7A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C9A C14A H14A 109.5 . . ?
C9A C14A H14B 109.5 . . ?
C9A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C11A C15A H15A 109.5 . . ?
C11A C15A H15B 109.5 . . ?
C11A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C8B C7B C12B 118.4(2) . . ?
C8B C7B C13B 120.8(2) . . ?
C12B C7B C13B 120.8(2) . . ?
C7B C8B H8B 119.2 . . ?
C7B C8B C9B 121.6(2) . . ?
C9B C8B H8B 119.2 . . ?
C8B C9B C10B 118.5(2) . . ?
C8B C9B C14B 120.5(2) . . ?
C10B C9B C14B 121.0(2) . . ?
C9B C10B H10B 119.4 . . ?
C11B C10B C9B 121.2(2) . . ?
C11B C10B H10B 119.4 . . ?
C10B C11B C15B 120.5(3) . . ?
C12B C11B C10B 118.8(2) . . ?
C12B C11B C15B 120.7(3) . . ?
C7B C12B H12B 119.3 . . ?
C11B C12B C7B 121.4(2) . . ?
C11B C12B H12B 119.3 . . ?
C7B C13B H13D 109.5 . . ?
C7B C13B H13E 109.5 . . ?
C7B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C9B C14B H14D 109.5 . . ?
C9B C14B H14E 109.5 . . ?
C9B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C11B C15B H15D 109.5 . . ?
C11B C15B H15E 109.5 . . ?
C11B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 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
C1A C2A C3A C4A 0.1(4) . . . . ?
C1A C2A C3A F3A -179.5(2) . . . . ?
C2A C1A C6A C5A 0.1(4) . . . . ?
C2A C1A C6A F6A -179.2(2) . . . . ?
C2A C3A C4A C5A 0.2(4) . . . . ?
C2A C3A C4A F4A -179.9(2) . . . . ?
C3A C4A C5A C6A -0.3(4) . . . . ?
C3A C4A C5A F5A 178.6(2) . . . . ?
C4A C5A C6A C1A 0.2(4) . . . . ?
C4A C5A C6A F6A 179.5(2) . . . . ?
C6A C1A C2A C3A -0.2(4) . . . . ?
C6A C1A C2A F2A 179.2(2) . . . . ?
F1A C1A C2A C3A -178.9(2) . . . . ?
F1A C1A C2A F2A 0.5(3) . . . . ?
F1A C1A C6A C5A 178.8(2) . . . . ?
F1A C1A C6A F6A -0.5(3) . . . . ?
F2A C2A C3A C4A -179.3(2) . . . . ?
F2A C2A C3A F3A 1.1(4) . . . . ?
F3A C3A C4A C5A 179.7(2) . . . . ?
F3A C3A C4A F4A -0.3(4) . . . . ?
F4A C4A C5A C6A 179.7(2) . . . . ?
F4A C4A C5A F5A -1.3(4) . . . . ?
F5A C5A C6A C1A -178.7(2) . . . . ?
F5A C5A C6A F6A 0.5(4) . . . . ?
C1B C2B C3B C4B 0.6(4) . . . . ?
C1B C2B C3B F3B -179.3(2) . . . . ?
C2B C1B C6B C5B -0.4(4) . . . . ?
C2B C1B C6B F6B 178.3(2) . . . . ?
C2B C3B C4B C5B -0.9(4) . . . . ?
C2B C3B C4B F4B -179.7(2) . . . . ?
C3B C4B C5B C6B 0.5(4) . . . . ?
C3B C4B C5B F5B -178.3(2) . . . . ?
C4B C5B C6B C1B 0.2(4) . . . . ?
C4B C5B C6B F6B -178.5(2) . . . . ?
C6B C1B C2B C3B 0.0(4) . . . . ?
C6B C1B C2B F2B -178.4(2) . . . . ?
F1B C1B C2B C3B 178.9(2) . . . . ?
F1B C1B C2B F2B 0.5(3) . . . . ?
F1B C1B C6B C5B -179.3(2) . . . . ?
F1B C1B C6B F6B -0.6(3) . . . . ?
F2B C2B C3B C4B 179.0(2) . . . . ?
F2B C2B C3B F3B -0.9(4) . . . . ?
F3B C3B C4B C5B 179.0(2) . . . . ?
F3B C3B C4B F4B 0.2(4) . . . . ?
F4B C4B C5B C6B 179.3(2) . . . . ?
F4B C4B C5B F5B 0.5(4) . . . . ?
F5B C5B C6B C1B 178.9(2) . . . . ?
F5B C5B C6B F6B 0.3(4) . . . . ?
C7A C8A C9A C10A 0.8(3) . . . . ?
C7A C8A C9A C14A -178.7(2) . . . . ?
C8A C7A C12A C11A 0.0(3) . . . . ?
C8A C9A C10A C11A -0.9(3) . . . . ?
C9A C10A C11A C12A 0.6(3) . . . . ?
C9A C10A C11A C15A 179.5(2) . . . . ?
C10A C11A C12A C7A -0.1(3) . . . . ?
C12A C7A C8A C9A -0.3(3) . . . . ?
C13A C7A C8A C9A 180.0(2) . . . . ?
C13A C7A C12A C11A 179.7(2) . . . . ?
C14A C9A C10A C11A 178.5(2) . . . . ?
C15A C11A C12A C7A -179.1(2) . . . . ?
C7B C8B C9B C10B 0.8(3) . . . . ?
C7B C8B C9B C14B -179.5(2) . . . . ?
C8B C7B C12B C11B 0.2(3) . . . . ?
C8B C9B C10B C11B -0.4(3) . . . . ?
C9B C10B C11B C12B -0.1(3) . . . . ?
C9B C10B C11B C15B 179.2(2) . . . . ?
C10B C11B C12B C7B 0.2(3) . . . . ?
C12B C7B C8B C9B -0.6(3) . . . . ?
C13B C7B C8B C9B 179.0(2) . . . . ?
C13B C7B C12B C11B -179.5(2) . . . . ?
C14B C9B C10B C11B 179.9(2) . . . . ?
C15B C11B C12B C7B -179.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.536
_oxdiff_exptl_absorpt_empirical_full_min 0.609
