# 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. 
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data_20161218e
_database_code_depnum_ccdc_archive 'CCDC 1547628'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2017-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        135TIPB-FA
_chemical_formula_moiety         'C6 F3 I3, 2(C16 H10)'
_chemical_formula_sum            'C38 H20 F3 I3'
_chemical_formula_weight         914.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1i1
_chemical_oxdiff_usercomment     Eu
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   17.2928(9)
_cell_length_b                   23.1876(10)
_cell_length_c                   7.7431(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3104.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6575
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9190
_cell_measurement_theta_min      3.9390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18806
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.937
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.909
_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  87.00   1.00    2.00    --   12.76  37.00   0.00   79
  2  ω    -20.00  27.00   1.00    2.00    --   12.76 -99.00  90.00   47
  3  ω     56.00  82.00   1.00    2.00    --   12.76-178.00  60.00   26
  4  ω    -59.00 -33.00   1.00    2.00    --   12.76 -19.00-180.00   26
  5  ω     35.00 100.00   1.00    2.00    --   12.76-178.00 -60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0278942000
_diffrn_orient_matrix_UB_12      0.0223659000
_diffrn_orient_matrix_UB_13      0.0058014000
_diffrn_orient_matrix_UB_21      0.0266469000
_diffrn_orient_matrix_UB_22      -0.0195680000
_diffrn_orient_matrix_UB_23      0.0376861000
_diffrn_orient_matrix_UB_31      0.0139569000
_diffrn_orient_matrix_UB_32      -0.0073143000
_diffrn_orient_matrix_UB_33      -0.0832520000
_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                3428
_reflns_number_total             4188
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.986
_refine_diff_density_min         -2.422
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.00308(13)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²+14.4871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C14(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5)
 C18(0.5) H18(0.5) C19(0.5) C20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5)
 C23(0.5) H23(0.5) C24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5)
 H27(0.5) C28(0.5) C29(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27)
4.b Fitted hexagon refined as free rotating group:
 C14(C15,C16,C17,C18,C19), C24(C25,C26,C27,C28,C29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6842(3) 0.7500 0.0496(7) 0.0217(11) Uani 1 2 d S T P . .
C2 C 0.6472(2) 0.69923(16) 0.0898(5) 0.0212(8) Uani 1 1 d . . . . .
C3 C 0.5755(2) 0.69788(15) 0.1693(5) 0.0212(8) Uani 1 1 d . . . . .
C4 C 0.5412(3) 0.7500 0.2083(7) 0.0202(11) Uani 1 2 d S T P . .
C5 C 0.6875(3) 0.64732(19) 0.5340(6) 0.0313(10) Uani 1 1 d . . . . .
H5 H 0.6625 0.6134 0.5650 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7602(3) 0.6457(2) 0.4494(6) 0.0394(12) Uani 1 1 d . . . . .
H6 H 0.7823 0.6102 0.4243 0.047 Uiso 1 1 calc R . . . .
C7 C 0.7987(3) 0.6950(2) 0.4034(6) 0.0344(11) Uani 1 1 d . . . . .
H7 H 0.8462 0.6923 0.3476 0.041 Uiso 1 1 calc R . . . .
C8 C 0.7674(3) 0.7500 0.4395(7) 0.0268(13) Uani 1 2 d S T P . .
C9 C 0.6956(3) 0.7500 0.5218(7) 0.0191(11) Uani 1 2 d S T P . .
C10 C 0.6550(2) 0.69970(17) 0.5692(5) 0.0227(8) Uani 1 1 d . . . . .
C11 C 0.5831(2) 0.71906(18) 0.6500(5) 0.0248(9) Uani 1 1 d . . . . .
C12 C 0.5208(3) 0.6891(2) 0.7181(6) 0.0363(11) Uani 1 1 d . . . . .
H12 H 0.5196 0.6490 0.7170 0.044 Uiso 1 1 calc R . . . .
C13 C 0.4601(3) 0.7208(3) 0.7885(6) 0.0481(15) Uani 1 1 d . . . . .
H13 H 0.4183 0.7014 0.8368 0.058 Uiso 1 1 calc R . . . .
C14 C 0.4304(4) 0.5087(3) 0.4349(9) 0.028(3) Uani 0.5 1 d . . . A -1
C15 C 0.3577(4) 0.5192(3) 0.3651(8) 0.031(2) Uani 0.5 1 d G . . A -1
H15 H 0.3460 0.5065 0.2542 0.037 Uiso 0.5 1 calc R . . A -1
C16 C 0.3024(3) 0.5486(3) 0.4611(11) 0.040(3) Uani 0.5 1 d G . . A -1
H16 H 0.2537 0.5556 0.4143 0.048 Uiso 0.5 1 calc R . . A -1
C17 C 0.3198(4) 0.5676(4) 0.6268(10) 0.052(4) Uani 0.5 1 d G . . A -1
H17 H 0.2828 0.5873 0.6910 0.063 Uiso 0.5 1 calc R . . A -1
C18 C 0.3925(4) 0.5571(3) 0.6967(8) 0.043(3) Uani 0.5 1 d G . . A -1
H18 H 0.4042 0.5698 0.8076 0.052 Uiso 0.5 1 calc R . . A -1
C19 C 0.4478(3) 0.5277(3) 0.6007(9) 0.0252(18) Uani 0.5 1 d G U . A -1
C20 C 0.5256(7) 0.5132(5) 0.6505(15) 0.019(2) Uani 0.5 1 d . . . A -1
C21 C 0.5773(6) 0.5179(3) 0.7882(13) 0.038(2) Uani 0.5 1 d . . . A -1
H21 H 0.5610 0.5357 0.8895 0.045 Uiso 0.5 1 calc R . . A -1
C22 C 0.6522(5) 0.4967(3) 0.7782(11) 0.0246(17) Uani 0.5 1 d . . . A -1
H22 H 0.6853 0.5006 0.8721 0.030 Uiso 0.5 1 calc R . . A -1
C23 C 0.6782(7) 0.4694(5) 0.6260(16) 0.035(3) Uani 0.5 1 d . . . A -1
H23 H 0.7287 0.4556 0.6224 0.042 Uiso 0.5 1 calc R . . A -1
C24 C 0.6299(4) 0.4619(3) 0.4762(9) 0.035(2) Uani 0.5 1 d . . . A -1
C25 C 0.6481(4) 0.4363(4) 0.3190(12) 0.059(5) Uani 0.5 1 d G . . A -1
H25 H 0.6971 0.4209 0.3012 0.071 Uiso 0.5 1 calc R . . A -1
C26 C 0.5930(5) 0.4337(4) 0.1886(9) 0.062(4) Uani 0.5 1 d G . . A -1
H26 H 0.6051 0.4165 0.0834 0.074 Uiso 0.5 1 calc R . . A -1
C27 C 0.5197(5) 0.4567(3) 0.2153(9) 0.063(4) Uani 0.5 1 d G . . A -1
H27 H 0.4829 0.4549 0.1280 0.076 Uiso 0.5 1 calc R . . A -1
C28 C 0.5016(4) 0.4823(4) 0.3724(10) 0.031(4) Uani 0.5 1 d G . . A -1
C29 C 0.5567(4) 0.4849(3) 0.5029(8) 0.020(2) Uani 0.5 1 d G . . A -1
F1 F 0.68020(16) 0.64898(11) 0.0476(3) 0.0354(6) Uani 1 1 d . . . . .
F2 F 0.47185(19) 0.7500 0.2845(5) 0.0289(8) Uani 1 2 d S T P . .
I1 I 0.79389(2) 0.7500 -0.06138(5) 0.03707(14) Uani 1 2 d S T P . .
I2 I 0.52070(2) 0.62088(2) 0.22803(4) 0.03852(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(5) 7_575 ?
C1 C2 1.376(5) . ?
C1 I1 2.082(6) . ?
C2 C3 1.384(6) . ?
C2 F1 1.338(4) . ?
C3 C4 1.380(5) . ?
C3 I2 2.072(4) . ?
C4 C3 1.380(5) 7_575 ?
C4 F2 1.337(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.417(7) . ?
C5 C10 1.366(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.413(5) . ?
C8 C7 1.413(5) 7_575 ?
C8 C9 1.396(8) . ?
C9 C10 1.409(5) . ?
C9 C10 1.409(5) 7_575 ?
C10 C11 1.463(6) . ?
C11 C11 1.435(8) 7_575 ?
C11 C12 1.386(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(8) . ?
C13 C13 1.353(13) 7_575 ?
C13 H13 0.9300 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C14 C28 1.458(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 C20 1.439(12) . ?
C20 C21 1.395(16) . ?
C20 C29 1.423(12) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(13) . ?
C22 H22 0.9300 . ?
C22 C23 1.412(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.439(14) . ?
C24 C25 1.3900 . ?
C24 C29 1.3900 . ?
C25 H25 0.9300 . ?
C25 C26 1.3900 . ?
C26 H26 0.9300 . ?
C26 C27 1.3900 . ?
C27 H27 0.9300 . ?
C27 C28 1.3900 . ?
C28 C29 1.3900 . ?

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 C2 117.7(5) 7_575 . ?
C2 C1 I1 121.1(3) 7_575 . ?
C2 C1 I1 121.1(3) . . ?
C1 C2 C3 122.5(4) . . ?
F1 C2 C1 119.4(4) . . ?
F1 C2 C3 118.1(4) . . ?
C2 C3 I2 121.8(3) . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 I2 120.7(3) . . ?
C3 C4 C3 122.3(5) 7_575 . ?
F2 C4 C3 118.8(3) . 7_575 ?
F2 C4 C3 118.8(3) . . ?
C6 C5 H5 120.7 . . ?
C10 C5 H5 120.7 . . ?
C10 C5 C6 118.7(4) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C7 128.9(6) . 7_575 ?
C9 C8 C7 115.6(3) . 7_575 ?
C9 C8 C7 115.6(3) . . ?
C8 C9 C10 124.2(3) . 7_575 ?
C8 C9 C10 124.2(3) . . ?
C10 C9 C10 111.7(5) 7_575 . ?
C5 C10 C9 118.6(4) . . ?
C5 C10 C11 135.1(4) . . ?
C9 C10 C11 106.3(4) . . ?
C11 C11 C10 107.9(2) 7_575 . ?
C12 C11 C10 132.0(4) . . ?
C12 C11 C11 120.1(3) . 7_575 ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.0(5) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C13 C12 121.9(3) 7_575 . ?
C13 C13 H13 119.0 7_575 . ?
C15 C14 C19 120.0 . . ?
C15 C14 C28 135.1(6) . . ?
C19 C14 C28 104.9(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C20 112.1(7) . . ?
C18 C19 C14 120.0 . . ?
C18 C19 C20 127.9(7) . . ?
C21 C20 C19 141.7(12) . . ?
C21 C20 C29 114.1(11) . . ?
C29 C20 C19 104.2(8) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.9(10) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(9) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 118.6 . . ?
C22 C23 C24 122.8(10) . . ?
C24 C23 H23 118.6 . . ?
C25 C24 C23 128.8(7) . . ?
C25 C24 C29 120.0 . . ?
C29 C24 C23 111.2(7) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C14 131.4(6) . . ?
C29 C28 C14 108.6(6) . . ?
C29 C28 C27 120.0 . . ?
C24 C29 C20 129.8(7) . . ?
C28 C29 C20 110.2(7) . . ?
C28 C29 C24 120.0 . . ?

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 0.0(6) . . . . ?
C1 C2 C3 I2 179.8(3) . . . . ?
C2 C1 C2 C3 -0.6(8) 7_575 . . . ?
C2 C1 C2 F1 177.8(3) 7_575 . . . ?
C2 C3 C4 C3 0.6(8) . . . 7_575 ?
C2 C3 C4 F2 179.7(4) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C5 C10 C11 C11 179.4(4) . . . 7_575 ?
C5 C10 C11 C12 -1.2(8) . . . . ?
C6 C5 C10 C9 -0.9(6) . . . . ?
C6 C5 C10 C11 179.2(4) . . . . ?
C6 C7 C8 C7 179.5(4) . . . 7_575 ?
C6 C7 C8 C9 -0.6(7) . . . . ?
C7 C8 C9 C10 -179.8(4) 7_575 . . . ?
C7 C8 C9 C10 179.8(4) . . . 7_575 ?
C7 C8 C9 C10 0.3(8) . . . . ?
C7 C8 C9 C10 -0.3(8) 7_575 . . 7_575 ?
C8 C9 C10 C5 0.4(7) . . . . ?
C8 C9 C10 C11 -179.6(5) . . . . ?
C9 C10 C11 C11 -0.5(3) . . . 7_575 ?
C9 C10 C11 C12 178.8(4) . . . . ?
C10 C5 C6 C7 0.6(7) . . . . ?
C10 C9 C10 C5 -179.1(3) 7_575 . . . ?
C10 C9 C10 C11 0.9(6) 7_575 . . . ?
C10 C11 C12 C13 179.5(4) . . . . ?
C11 C11 C12 C13 -1.2(5) 7_575 . . . ?
C11 C12 C13 C13 1.3(5) . . . 7_575 ?
C14 C15 C16 C17 0.0 . . . . ?
C14 C19 C20 C21 -179.0(13) . . . . ?
C14 C19 C20 C29 1.3(9) . . . . ?
C14 C28 C29 C20 -1.1(8) . . . . ?
C14 C28 C29 C24 179.3(7) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C15 C14 C19 C20 -179.7(7) . . . . ?
C15 C14 C28 C27 -1.7(10) . . . . ?
C15 C14 C28 C29 179.1(4) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C17 C18 C19 C20 179.7(9) . . . . ?
C18 C19 C20 C21 1(2) . . . . ?
C18 C19 C20 C29 -178.4(4) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C19 C14 C28 C27 -178.9(7) . . . . ?
C19 C14 C28 C29 1.8(5) . . . . ?
C19 C20 C21 C22 -179.3(13) . . . . ?
C19 C20 C29 C24 179.5(8) . . . . ?
C19 C20 C29 C28 0.0(10) . . . . ?
C20 C21 C22 C23 -0.1(13) . . . . ?
C21 C20 C29 C24 -0.3(10) . . . . ?
C21 C20 C29 C28 -179.8(7) . . . . ?
C21 C22 C23 C24 -0.1(13) . . . . ?
C22 C23 C24 C25 179.6(7) . . . . ?
C22 C23 C24 C29 0.1(11) . . . . ?
C23 C24 C25 C26 -179.5(8) . . . . ?
C23 C24 C29 C20 0.1(8) . . . . ?
C23 C24 C29 C28 179.6(7) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C24 C29 C20 -179.5(8) . . . . ?
C25 C24 C29 C28 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C14 -179.1(9) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C20 179.6(6) . . . . ?
C27 C28 C29 C24 0.0 . . . . ?
C28 C14 C15 C16 -177.0(7) . . . . ?
C28 C14 C19 C18 177.8(5) . . . . ?
C28 C14 C19 C20 -1.9(6) . . . . ?
C29 C20 C21 C22 0.3(13) . . . . ?
C29 C24 C25 C26 0.0 . . . . ?
F1 C2 C3 C4 -178.5(4) . . . . ?
F1 C2 C3 I2 1.4(5) . . . . ?
I1 C1 C2 C3 177.6(3) . . . . ?
I1 C1 C2 F1 -4.0(6) . . . . ?
I2 C3 C4 C3 -179.2(3) . . . 7_575 ?
I2 C3 C4 F2 -0.1(6) . . . . ?

_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 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_20161127c
_database_code_depnum_ccdc_archive 'CCDC 1547625'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        FA
_chemical_formula_moiety         'C16 H10'
_chemical_formula_sum            'C16 H10'
_chemical_formula_weight         202.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1i1
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'

_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                   17.8455(8)
_cell_length_b                   6.2494(3)
_cell_length_c                   19.5446(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.407(5)
_cell_angle_gamma                90
_cell_volume                     2068.17(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4138
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1550
_cell_measurement_theta_min      3.7580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11278
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.827
_diffrn_reflns_theta_min         3.425
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  87.00   1.00   10.00    --   12.76  37.00 120.00   97
  2  ω     58.00  84.00   1.00   10.00    --   12.76  37.00 150.00   26
  3  ω    -45.00  46.00   1.00   10.00    --   12.76 -19.00 -60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0182986000
_diffrn_orient_matrix_UB_12      -0.0058685000
_diffrn_orient_matrix_UB_13      -0.0378465000
_diffrn_orient_matrix_UB_21      -0.0352908000
_diffrn_orient_matrix_UB_22      0.0425620000
_diffrn_orient_matrix_UB_23      0.0039013000
_diffrn_orient_matrix_UB_31      0.0132768000
_diffrn_orient_matrix_UB_32      0.1050596000
_diffrn_orient_matrix_UB_33      -0.0036937000
_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                4073
_reflns_number_total             4993
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.026
_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)+(0.0455P)²+0.8772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1185
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
  C28(H28), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.46661(8) 0.0557(2) 0.86828(8) 0.0218(3) Uani 1 1 d . . . . .
H1 H 0.4966 -0.0690 0.8769 0.026 Uiso 1 1 calc R . . . .
C2 C 0.47260(9) 0.2023(2) 0.92359(8) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.5071 0.1749 0.9695 0.030 Uiso 1 1 calc R . . . .
C3 C 0.42773(9) 0.3892(2) 0.91106(8) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.4328 0.4848 0.9487 0.028 Uiso 1 1 calc R . . . .
C4 C 0.37533(8) 0.4349(2) 0.84288(7) 0.0212(3) Uani 1 1 d . . . . .
H4 H 0.3454 0.5598 0.8347 0.025 Uiso 1 1 calc R . . . .
C5 C 0.36886(8) 0.2898(2) 0.78756(7) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.41498(8) 0.1001(2) 0.80017(7) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.39608(8) -0.0189(2) 0.73130(7) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.42307(8) -0.2026(2) 0.70865(8) 0.0213(3) Uani 1 1 d . . . . .
H8 H 0.4611 -0.2869 0.7409 0.026 Uiso 1 1 calc R . . . .
C9 C 0.39190(9) -0.2614(2) 0.63507(8) 0.0226(3) Uani 1 1 d . . . . .
H9 H 0.4106 -0.3850 0.6195 0.027 Uiso 1 1 calc R . . . .
C10 C 0.33490(8) -0.1425(2) 0.58568(8) 0.0214(3) Uani 1 1 d . . . . .
H10 H 0.3155 -0.1875 0.5380 0.026 Uiso 1 1 calc R . . . .
C11 C 0.30561(8) 0.0490(2) 0.60749(7) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.24749(8) 0.1926(2) 0.56471(7) 0.0206(3) Uani 1 1 d . . . . .
H12 H 0.2232 0.1643 0.5160 0.025 Uiso 1 1 calc R . . . .
C13 C 0.22726(8) 0.3730(2) 0.59529(8) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.1886 0.4631 0.5665 0.026 Uiso 1 1 calc R . . . .
C14 C 0.26294(8) 0.4272(2) 0.66898(8) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.2487 0.5514 0.6880 0.025 Uiso 1 1 calc R . . . .
C15 C 0.31886(8) 0.2917(2) 0.71131(7) 0.0178(3) Uani 1 1 d . . . . .
C16 C 0.33828(8) 0.1038(2) 0.67999(7) 0.0169(3) Uani 1 1 d . . . . .
C17 C 0.60968(9) 0.5441(2) 0.86013(8) 0.0248(3) Uani 1 1 d . . . . .
H17 H 0.5845 0.4205 0.8679 0.030 Uiso 1 1 calc R . . . .
C18 C 0.64122(9) 0.6900(3) 0.91587(8) 0.0283(3) Uani 1 1 d . . . . .
H18 H 0.6369 0.6631 0.9613 0.034 Uiso 1 1 calc R . . . .
C19 C 0.67894(9) 0.8747(3) 0.90464(8) 0.0266(3) Uani 1 1 d . . . . .
H19 H 0.6997 0.9691 0.9427 0.032 Uiso 1 1 calc R . . . .
C20 C 0.68619(8) 0.9208(2) 0.83732(8) 0.0223(3) Uani 1 1 d . . . . .
H20 H 0.7112 1.0452 0.8300 0.027 Uiso 1 1 calc R . . . .
C21 C 0.65529(8) 0.7772(2) 0.78153(7) 0.0183(3) Uani 1 1 d . . . . .
C22 C 0.61675(8) 0.5877(2) 0.79272(7) 0.0192(3) Uani 1 1 d . . . . .
C23 C 0.58991(8) 0.4688(2) 0.72385(7) 0.0194(3) Uani 1 1 d . . . . .
C24 C 0.54784(8) 0.2849(2) 0.70006(8) 0.0249(3) Uani 1 1 d . . . . .
H24 H 0.5307 0.2008 0.7314 0.030 Uiso 1 1 calc R . . . .
C25 C 0.53107(9) 0.2257(2) 0.62694(9) 0.0278(3) Uani 1 1 d . . . . .
H25 H 0.5017 0.1024 0.6106 0.033 Uiso 1 1 calc R . . . .
C26 C 0.55652(8) 0.3435(2) 0.57897(8) 0.0261(3) Uani 1 1 d . . . . .
H26 H 0.5450 0.2977 0.5315 0.031 Uiso 1 1 calc R . . . .
C27 C 0.60032(8) 0.5346(2) 0.60170(8) 0.0220(3) Uani 1 1 d . . . . .
C28 C 0.63108(8) 0.6778(3) 0.56058(8) 0.0245(3) Uani 1 1 d . . . . .
H28 H 0.6241 0.6484 0.5123 0.029 Uiso 1 1 calc R . . . .
C29 C 0.67097(8) 0.8591(2) 0.59170(8) 0.0245(3) Uani 1 1 d . . . . .
H29 H 0.6907 0.9494 0.5637 0.029 Uiso 1 1 calc R . . . .
C30 C 0.68323(8) 0.9141(2) 0.66476(8) 0.0214(3) Uani 1 1 d . . . . .
H30 H 0.7098 1.0390 0.6842 0.026 Uiso 1 1 calc R . . . .
C31 C 0.65497(8) 0.7786(2) 0.70606(7) 0.0181(3) Uani 1 1 d . . . . .
C32 C 0.61473(8) 0.5911(2) 0.67388(7) 0.0186(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.395(2) . ?
C1 C6 1.3867(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.3879(19) . ?
C5 C6 1.4197(19) . ?
C5 C15 1.4757(19) . ?
C6 C7 1.4803(19) . ?
C7 C8 1.3716(19) . ?
C7 C16 1.4157(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.417(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.4244(19) . ?
C11 C12 1.4254(19) . ?
C11 C16 1.3940(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.420(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.3696(19) . ?
C15 C16 1.4166(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.396(2) . ?
C17 C22 1.3896(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.3851(19) . ?
C21 C22 1.4207(19) . ?
C21 C31 1.4732(19) . ?
C22 C23 1.478(2) . ?
C23 C24 1.371(2) . ?
C23 C32 1.4169(19) . ?
C24 H24 0.9300 . ?
C24 C25 1.414(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.420(2) . ?
C27 C28 1.424(2) . ?
C27 C32 1.3969(19) . ?
C28 H28 0.9300 . ?
C28 C29 1.373(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.417(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.3711(19) . ?
C31 C32 1.4143(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.53(14) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.01(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.96(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.44(13) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 120.63(13) . . ?
C4 C5 C15 131.03(13) . . ?
C6 C5 C15 108.34(12) . . ?
C1 C6 C5 120.43(13) . . ?
C1 C6 C7 131.61(13) . . ?
C5 C6 C7 107.95(12) . . ?
C8 C7 C6 135.35(13) . . ?
C8 C7 C16 118.45(13) . . ?
C16 C7 C6 106.15(12) . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.64(13) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.53(13) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.20(13) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 128.40(13) . . ?
C16 C11 C10 115.82(12) . . ?
C16 C11 C12 115.78(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.18(13) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 118.6 . . ?
C12 C13 C14 122.74(13) . . ?
C14 C13 H13 118.6 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.24(13) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C5 135.07(13) . . ?
C14 C15 C16 118.83(13) . . ?
C16 C15 C5 106.10(11) . . ?
C7 C16 C15 111.45(12) . . ?
C11 C16 C7 124.35(13) . . ?
C11 C16 C15 124.19(12) . . ?
C18 C17 H17 120.8 . . ?
C22 C17 H17 120.8 . . ?
C22 C17 C18 118.48(14) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.08(14) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.06(14) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.51(14) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C22 120.70(13) . . ?
C20 C21 C31 131.22(13) . . ?
C22 C21 C31 108.08(12) . . ?
C17 C22 C21 120.18(13) . . ?
C17 C22 C23 131.63(13) . . ?
C21 C22 C23 108.19(12) . . ?
C24 C23 C22 135.66(13) . . ?
C24 C23 C32 118.37(13) . . ?
C32 C23 C22 105.94(12) . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.72(14) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 118.7 . . ?
C26 C25 C24 122.57(14) . . ?
C26 C25 H25 118.7 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.27(14) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 128.64(14) . . ?
C32 C27 C26 115.85(13) . . ?
C32 C27 C28 115.50(13) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.45(13) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 118.7 . . ?
C28 C29 C30 122.68(13) . . ?
C30 C29 H29 118.7 . . ?
C29 C30 H30 120.8 . . ?
C31 C30 C29 118.37(13) . . ?
C31 C30 H30 120.8 . . ?
C30 C31 C21 135.03(13) . . ?
C30 C31 C32 118.64(13) . . ?
C32 C31 C21 106.33(12) . . ?
C27 C32 C23 124.20(13) . . ?
C27 C32 C31 124.34(13) . . ?
C31 C32 C23 111.45(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C7 C8 -3.4(3) . . . . ?
C1 C6 C7 C16 179.53(14) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C1 C6 C7 179.14(14) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C15 179.12(13) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 -179.05(12) . . . . ?
C4 C5 C15 C14 -0.7(3) . . . . ?
C4 C5 C15 C16 178.99(14) . . . . ?
C5 C6 C7 C8 176.40(15) . . . . ?
C5 C6 C7 C16 -0.70(14) . . . . ?
C5 C15 C16 C7 1.00(15) . . . . ?
C5 C15 C16 C11 -177.88(12) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C6 C5 C15 C14 178.85(15) . . . . ?
C6 C5 C15 C16 -1.42(14) . . . . ?
C6 C7 C8 C9 -176.88(14) . . . . ?
C6 C7 C16 C11 178.66(12) . . . . ?
C6 C7 C16 C15 -0.21(15) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C7 C16 C11 1.0(2) . . . . ?
C8 C7 C16 C15 -177.89(12) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 179.78(14) . . . . ?
C9 C10 C11 C16 0.10(19) . . . . ?
C10 C11 C12 C13 -179.15(13) . . . . ?
C10 C11 C16 C7 -0.99(19) . . . . ?
C10 C11 C16 C15 177.74(12) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C11 C16 C7 179.29(12) . . . . ?
C12 C11 C16 C15 -1.98(19) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
C13 C14 C15 C5 179.40(14) . . . . ?
C13 C14 C15 C16 -0.31(19) . . . . ?
C14 C15 C16 C7 -179.22(12) . . . . ?
C14 C15 C16 C11 1.9(2) . . . . ?
C15 C5 C6 C1 -178.89(12) . . . . ?
C15 C5 C6 C7 1.31(14) . . . . ?
C16 C7 C8 C9 -0.05(19) . . . . ?
C16 C11 C12 C13 0.53(19) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C17 C22 C23 C24 2.7(3) . . . . ?
C17 C22 C23 C32 -179.50(14) . . . . ?
C18 C17 C22 C21 -0.1(2) . . . . ?
C18 C17 C22 C23 -179.62(14) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C19 C20 C21 C22 0.3(2) . . . . ?
C19 C20 C21 C31 -178.65(13) . . . . ?
C20 C21 C22 C17 0.0(2) . . . . ?
C20 C21 C22 C23 179.60(12) . . . . ?
C20 C21 C31 C30 -0.1(3) . . . . ?
C20 C21 C31 C32 -179.86(14) . . . . ?
C21 C22 C23 C24 -176.92(15) . . . . ?
C21 C22 C23 C32 0.91(15) . . . . ?
C21 C31 C32 C23 -0.53(15) . . . . ?
C21 C31 C32 C27 178.71(13) . . . . ?
C22 C17 C18 C19 -0.1(2) . . . . ?
C22 C21 C31 C30 -179.13(15) . . . . ?
C22 C21 C31 C32 1.10(14) . . . . ?
C22 C23 C24 C25 177.57(15) . . . . ?
C22 C23 C32 C27 -179.45(12) . . . . ?
C22 C23 C32 C31 -0.21(15) . . . . ?
C23 C24 C25 C26 1.2(2) . . . . ?
C24 C23 C32 C27 -1.2(2) . . . . ?
C24 C23 C32 C31 178.06(12) . . . . ?
C24 C25 C26 C27 -1.1(2) . . . . ?
C25 C26 C27 C28 -179.56(14) . . . . ?
C25 C26 C27 C32 -0.1(2) . . . . ?
C26 C27 C28 C29 178.59(14) . . . . ?
C26 C27 C32 C23 1.3(2) . . . . ?
C26 C27 C32 C31 -177.89(13) . . . . ?
C27 C28 C29 C30 -0.4(2) . . . . ?
C28 C27 C32 C23 -179.24(13) . . . . ?
C28 C27 C32 C31 1.6(2) . . . . ?
C28 C29 C30 C31 1.0(2) . . . . ?
C29 C30 C31 C21 -179.97(14) . . . . ?
C29 C30 C31 C32 -0.2(2) . . . . ?
C30 C31 C32 C23 179.65(12) . . . . ?
C30 C31 C32 C27 -1.1(2) . . . . ?
C31 C21 C22 C17 179.11(12) . . . . ?
C31 C21 C22 C23 -1.24(14) . . . . ?
C32 C23 C24 C25 0.0(2) . . . . ?
C32 C27 C28 C29 -0.8(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 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_20161218b
_database_code_depnum_ccdc_archive 'CCDC 1547630'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        1IPB-FA
_chemical_formula_moiety         'C6 F5 I, C16 H10'
_chemical_formula_sum            'C22 H10 F5 I'
_chemical_formula_weight         496.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1i1
_chemical_oxdiff_usercomment     Eu
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           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                   9.5860(6)
_cell_length_b                   15.0356(7)
_cell_length_c                   12.5798(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.274(5)
_cell_angle_gamma                90
_cell_volume                     1749.09(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2966
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0090
_cell_measurement_theta_min      4.0930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.950
_diffrn_reflns_theta_min         3.385
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  19.00   1.00    2.00    --   12.76 -37.00 -60.00   60
  2  ω    -74.00  48.00   1.00    2.00    --   12.76   0.00-180.00  122
  3  ω     68.00  99.00   1.00    2.00    --   12.76-178.00 -30.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0719132000
_diffrn_orient_matrix_UB_12      -0.0159231000
_diffrn_orient_matrix_UB_13      -0.0099380000
_diffrn_orient_matrix_UB_21      0.0208798000
_diffrn_orient_matrix_UB_22      -0.0405989000
_diffrn_orient_matrix_UB_23      -0.0201297000
_diffrn_orient_matrix_UB_31      0.0164847000
_diffrn_orient_matrix_UB_32      -0.0180227000
_diffrn_orient_matrix_UB_33      0.0539841000
_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                3272
_reflns_number_total             4232
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.039
_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)+(0.0278P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.7235(4) 0.3310(2) 0.5014(2) 0.0126(7) Uani 1 1 d . . . . .
C2 C 0.7546(4) 0.2427(3) 0.4888(2) 0.0171(8) Uani 1 1 d . . . . .
C3 C 0.6814(4) 0.1754(2) 0.5260(2) 0.0153(7) Uani 1 1 d . . . . .
C4 C 0.5743(4) 0.1970(3) 0.5768(2) 0.0167(8) Uani 1 1 d . . . . .
C5 C 0.5420(4) 0.2844(3) 0.5911(2) 0.0173(8) Uani 1 1 d . . . . .
C6 C 0.6157(4) 0.3508(2) 0.5522(2) 0.0149(7) Uani 1 1 d . . . . .
F1 F 0.8580(2) 0.22007(15) 0.43915(14) 0.0227(5) Uani 1 1 d . . . . .
F2 F 0.7137(2) 0.08981(14) 0.51374(15) 0.0227(5) Uani 1 1 d . . . . .
F3 F 0.5028(2) 0.13168(15) 0.61217(15) 0.0245(5) Uani 1 1 d . . . . .
F4 F 0.4385(2) 0.30546(15) 0.64030(14) 0.0235(5) Uani 1 1 d . . . . .
F5 F 0.5819(2) 0.43548(13) 0.56736(15) 0.0220(5) Uani 1 1 d . . . . .
I1 I 0.83589(2) 0.43248(2) 0.44793(2) 0.01982(9) Uani 1 1 d . . . . .
C7 C 0.5589(4) 0.3185(2) 0.2034(2) 0.0153(8) Uani 1 1 d . . . . .
C8 C 0.6590(4) 0.3441(3) 0.1468(2) 0.0165(8) Uani 1 1 d . . . . .
H8 H 0.7167 0.3020 0.1248 0.020 Uiso 1 1 calc R . . . .
C9 C 0.6713(4) 0.4336(3) 0.1238(3) 0.0178(8) Uani 1 1 d . . . . .
H9 H 0.7376 0.4515 0.0858 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5856(4) 0.4969(3) 0.1569(2) 0.0182(8) Uani 1 1 d . . . . .
H10 H 0.5952 0.5565 0.1404 0.022 Uiso 1 1 calc R . . . .
C11 C 0.4859(4) 0.4725(3) 0.2142(2) 0.0167(8) Uani 1 1 d . . . . .
H11 H 0.4297 0.5153 0.2368 0.020 Uiso 1 1 calc R . . . .
C12 C 0.4714(3) 0.3837(2) 0.2371(2) 0.0135(7) Uani 1 1 d . . . . .
C13 C 0.3735(3) 0.3360(2) 0.2922(2) 0.0123(7) Uani 1 1 d . . . . .
C14 C 0.2660(4) 0.3610(3) 0.3404(2) 0.0173(8) Uani 1 1 d . . . . .
H14 H 0.2423 0.4206 0.3450 0.021 Uiso 1 1 calc R . . . .
C15 C 0.1919(4) 0.2928(3) 0.3830(3) 0.0202(8) Uani 1 1 d . . . . .
H15 H 0.1188 0.3092 0.4153 0.024 Uiso 1 1 calc R . . . .
C16 C 0.2243(4) 0.2039(3) 0.3782(2) 0.0195(8) Uani 1 1 d . . . . .
H16 H 0.1733 0.1616 0.4066 0.023 Uiso 1 1 calc R . . . .
C17 C 0.3362(4) 0.1766(2) 0.3295(2) 0.0155(8) Uani 1 1 d . . . . .
C18 C 0.3861(4) 0.0889(3) 0.3198(3) 0.0185(8) Uani 1 1 d . . . . .
H18 H 0.3437 0.0413 0.3467 0.022 Uiso 1 1 calc R . . . .
C19 C 0.4967(4) 0.0737(2) 0.2708(3) 0.0176(8) Uani 1 1 d . . . . .
H19 H 0.5275 0.0156 0.2651 0.021 Uiso 1 1 calc R . . . .
C20 C 0.5651(4) 0.1444(3) 0.2288(2) 0.0175(8) Uani 1 1 d . . . . .
H20 H 0.6401 0.1328 0.1966 0.021 Uiso 1 1 calc R . . . .
C21 C 0.5189(3) 0.2299(2) 0.2365(2) 0.0129(7) Uani 1 1 d . . . . .
C22 C 0.4056(3) 0.2442(2) 0.2878(2) 0.0144(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(5) . ?
C1 C6 1.383(5) . ?
C1 I1 2.079(3) . ?
C2 C3 1.382(5) . ?
C2 F1 1.347(4) . ?
C3 C4 1.383(5) . ?
C3 F2 1.341(4) . ?
C4 C5 1.373(5) . ?
C4 F3 1.339(4) . ?
C5 C6 1.384(5) . ?
C5 F4 1.338(4) . ?
C6 F5 1.340(4) . ?
C7 C8 1.391(5) . ?
C7 C12 1.426(5) . ?
C7 C21 1.476(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(5) . ?
C12 C13 1.489(5) . ?
C13 C14 1.378(5) . ?
C13 C22 1.419(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.429(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.428(5) . ?
C17 C18 1.418(5) . ?
C17 C22 1.391(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.422(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.371(5) . ?
C21 C22 1.418(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 C6 118.1(3) . . ?
C2 C1 I1 121.6(3) . . ?
C6 C1 I1 120.4(3) . . ?
C1 C2 C3 121.5(3) . . ?
F1 C2 C1 120.3(3) . . ?
F1 C2 C3 118.2(3) . . ?
C2 C3 C4 119.3(3) . . ?
F2 C3 C2 120.7(3) . . ?
F2 C3 C4 120.0(3) . . ?
C5 C4 C3 120.4(3) . . ?
F3 C4 C3 119.2(3) . . ?
F3 C4 C5 120.4(3) . . ?
C4 C5 C6 119.3(3) . . ?
F4 C5 C4 120.5(3) . . ?
F4 C5 C6 120.2(3) . . ?
C1 C6 C5 121.4(3) . . ?
F5 C6 C1 120.5(3) . . ?
F5 C6 C5 118.0(3) . . ?
C8 C7 C12 120.1(3) . . ?
C8 C7 C21 131.2(3) . . ?
C12 C7 C21 108.7(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C13 107.4(3) . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 C13 132.3(3) . . ?
C14 C13 C12 135.2(3) . . ?
C14 C13 C22 118.5(3) . . ?
C22 C13 C12 106.3(3) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.2(3) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 118.7 . . ?
C16 C15 C14 122.6(3) . . ?
C16 C15 H15 118.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 127.8(3) . . ?
C22 C17 C16 116.0(3) . . ?
C22 C17 C18 116.2(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C7 135.5(3) . . ?
C20 C21 C22 118.3(3) . . ?
C22 C21 C7 106.2(3) . . ?
C17 C22 C13 124.5(3) . . ?
C17 C22 C21 124.1(3) . . ?
C21 C22 C13 111.4(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
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 F2 -179.6(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C1 C6 F5 179.4(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 F3 179.6(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C3 C4 C5 F4 -179.9(3) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 F5 -180.0(3) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C6 C1 C2 F1 179.6(3) . . . . ?
F1 C2 C3 C4 -179.7(3) . . . . ?
F1 C2 C3 F2 0.6(4) . . . . ?
F2 C3 C4 C5 179.1(3) . . . . ?
F2 C3 C4 F3 -0.7(4) . . . . ?
F3 C4 C5 C6 -178.9(3) . . . . ?
F3 C4 C5 F4 -0.2(5) . . . . ?
F4 C5 C6 C1 179.8(3) . . . . ?
F4 C5 C6 F5 1.2(4) . . . . ?
I1 C1 C2 C3 178.9(2) . . . . ?
I1 C1 C2 F1 -1.3(4) . . . . ?
I1 C1 C6 C5 -178.3(2) . . . . ?
I1 C1 C6 F5 0.2(4) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C7 C12 C13 C14 -179.4(3) . . . . ?
C7 C12 C13 C22 -0.7(3) . . . . ?
C7 C21 C22 C13 -1.6(3) . . . . ?
C7 C21 C22 C17 179.2(3) . . . . ?
C8 C7 C12 C11 -0.2(4) . . . . ?
C8 C7 C12 C13 178.4(3) . . . . ?
C8 C7 C21 C20 2.9(6) . . . . ?
C8 C7 C21 C22 -177.4(3) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C7 0.7(4) . . . . ?
C10 C11 C12 C13 -177.6(3) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C11 C12 C13 C22 177.8(3) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
C12 C7 C21 C20 -178.6(3) . . . . ?
C12 C7 C21 C22 1.1(3) . . . . ?
C12 C13 C14 C15 178.3(3) . . . . ?
C12 C13 C22 C17 -179.3(3) . . . . ?
C12 C13 C22 C21 1.4(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C13 C22 C17 -0.3(5) . . . . ?
C14 C13 C22 C21 -179.6(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C18 178.4(3) . . . . ?
C15 C16 C17 C22 -0.8(5) . . . . ?
C16 C17 C18 C19 -179.5(3) . . . . ?
C16 C17 C22 C13 0.9(5) . . . . ?
C16 C17 C22 C21 -179.9(3) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C18 C17 C22 C13 -178.4(3) . . . . ?
C18 C17 C22 C21 0.8(5) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C19 C20 C21 C7 -179.4(3) . . . . ?
C19 C20 C21 C22 0.9(4) . . . . ?
C20 C21 C22 C13 178.2(3) . . . . ?
C20 C21 C22 C17 -1.1(5) . . . . ?
C21 C7 C8 C9 178.1(3) . . . . ?
C21 C7 C12 C11 -178.9(3) . . . . ?
C21 C7 C12 C13 -0.3(3) . . . . ?
C22 C13 C14 C15 -0.3(4) . . . . ?
C22 C17 C18 C19 -0.3(5) . . . . ?

_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 2.129
_oxdiff_exptl_absorpt_empirical_full_min 0.659
####################################################################### 
# 
# 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_20161209c
_database_code_depnum_ccdc_archive 'CCDC 1547627'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        14DIPB-FA
_chemical_formula_moiety         'C6 F4 I2, C16 H10'
_chemical_formula_sum            'C22 H10 F4 I2'
_chemical_formula_weight         604.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1i1
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.3808(6)
_cell_length_b                   18.0644(10)
_cell_length_c                   12.8815(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.561(9)
_cell_angle_gamma                90.00
_cell_volume                     1878.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.8300
_cell_measurement_theta_min      3.4630
_exptl_absorpt_coefficient_mu    3.391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8584
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.38
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8487
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  37.00   1.00    1.00    --   12.76 -37.00 -30.00   80
  2  ω    -20.00  61.00   1.00    1.00    --   12.76  77.00 150.00   81
  3  ω    -29.00  14.00   1.00    1.00    --   12.76 -37.00  30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0846377000
_diffrn_orient_matrix_UB_12      0.0070002000
_diffrn_orient_matrix_UB_13      0.0256818000
_diffrn_orient_matrix_UB_21      -0.0158903000
_diffrn_orient_matrix_UB_22      0.0386277000
_diffrn_orient_matrix_UB_23      -0.0032677000
_diffrn_orient_matrix_UB_31      -0.0172434000
_diffrn_orient_matrix_UB_32      -0.0010757000
_diffrn_orient_matrix_UB_33      0.0509687000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2898
_reflns_number_total             3419
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0098P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0617
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C18(H18), C25(H25), C28(H28), C27(H27), C16(H16), C20(H20),
 C19(H19), C15(H15), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I8 I 0.15906(4) 0.720205(14) 0.26384(2) 0.01845(10) Uani 1 d . . .
I7 I 0.58163(4) 1.053514(15) 0.27178(3) 0.02360(10) Uani 1 d . . .
F9 F 0.3901(3) 0.81478(13) 0.45519(17) 0.0233(6) Uani 1 d . . .
F12 F 0.1779(3) 0.83480(13) 0.07682(18) 0.0256(6) Uani 1 d . . .
F10 F 0.5607(3) 0.93896(12) 0.45803(18) 0.0236(6) Uani 1 d . . .
F11 F 0.3419(3) 0.96142(13) 0.08110(19) 0.0275(7) Uani 1 d . . .
C4 C 0.2820(5) 0.8207(2) 0.2660(3) 0.0134(10) Uani 1 d . . .
C26 C 1.1524(6) 0.4278(2) 0.8130(3) 0.0197(10) Uani 1 d . . .
H26 H 1.2247 0.3921 0.8511 0.024 Uiso 1 calc . . R
C24 C 1.0045(5) 0.5404(2) 0.8103(3) 0.0122(9) Uani 1 d . . .
C18 C 0.6139(6) 0.7195(2) 0.6506(3) 0.0164(10) Uani 1 d . . .
H18 H 0.5468 0.7611 0.6450 0.020 Uiso 1 calc . . R
C25 C 1.0865(6) 0.4201(2) 0.7024(3) 0.0189(10) Uani 1 d . . .
H25 H 1.1172 0.3798 0.6671 0.023 Uiso 1 calc . . R
C5 C 0.2706(5) 0.8600(2) 0.1725(3) 0.0147(10) Uani 1 d . . .
C28 C 0.9750(6) 0.4720(2) 0.6434(3) 0.0169(10) Uani 1 d . . .
H28 H 0.9294 0.4661 0.5697 0.020 Uiso 1 calc . . R
C27 C 1.1112(6) 0.4884(2) 0.8673(3) 0.0182(10) Uani 1 d . . .
H27 H 1.1555 0.4935 0.9413 0.022 Uiso 1 calc . . R
C2 C 0.4652(6) 0.9145(2) 0.3630(3) 0.0172(10) Uani 1 d . . .
C17 C 0.7244(5) 0.7003(2) 0.7515(3) 0.0134(10) Uani 1 d . . .
C22 C 0.8200(6) 0.6371(2) 0.7524(3) 0.0144(10) Uani 1 d . . .
C23 C 0.9334(5) 0.5325(2) 0.6971(3) 0.0140(10) Uani 1 d . . .
C1 C 0.4535(6) 0.9545(2) 0.2698(3) 0.0164(10) Uani 1 d . . .
C3 C 0.3778(6) 0.8496(2) 0.3617(3) 0.0151(10) Uani 1 d . . .
C16 C 0.7457(6) 0.7360(2) 0.8516(3) 0.0169(10) Uani 1 d . . .
H16 H 0.6836 0.7779 0.8563 0.020 Uiso 1 calc . . R
C21 C 0.8161(5) 0.5939(2) 0.6596(3) 0.0141(10) Uani 1 d . . .
C6 C 0.3572(6) 0.9261(2) 0.1752(3) 0.0185(10) Uani 1 d . . .
C13 C 0.9334(5) 0.6090(2) 0.8448(3) 0.0140(10) Uani 1 d . . .
C20 C 0.7078(6) 0.6133(2) 0.5639(3) 0.0181(10) Uani 1 d . . .
H20 H 0.7009 0.5857 0.5019 0.022 Uiso 1 calc . . R
C19 C 0.6061(6) 0.6764(2) 0.5610(3) 0.0193(11) Uani 1 d . . .
H19 H 0.5313 0.6893 0.4961 0.023 Uiso 1 calc . . R
C15 C 0.8570(6) 0.7095(2) 0.9421(3) 0.0188(11) Uani 1 d . . .
H15 H 0.8701 0.7347 1.0068 0.023 Uiso 1 calc . . R
C14 C 0.9533(6) 0.6449(2) 0.9406(3) 0.0186(10) Uani 1 d . . .
H14 H 1.0277 0.6276 1.0030 0.022 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I8 C4 2.083(4) . ?
I7 C1 2.083(4) . ?
F9 C3 1.338(4) . ?
F12 C5 1.348(5) . ?
F10 C2 1.344(5) . ?
F11 C6 1.345(4) . ?
C4 C5 1.380(5) . ?
C4 C3 1.380(6) . ?
C26 H26 0.9300 . ?
C26 C25 1.391(6) . ?
C26 C27 1.392(6) . ?
C24 C27 1.367(6) . ?
C24 C23 1.426(6) . ?
C24 C13 1.493(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.422(6) . ?
C18 C19 1.379(5) . ?
C25 H25 0.9300 . ?
C25 C28 1.396(6) . ?
C5 C6 1.392(6) . ?
C28 H28 0.9300 . ?
C28 C23 1.386(5) . ?
C27 H27 0.9300 . ?
C2 C1 1.382(6) . ?
C2 C3 1.381(6) . ?
C17 C22 1.393(6) . ?
C17 C16 1.410(5) . ?
C22 C21 1.422(5) . ?
C22 C13 1.404(6) . ?
C23 C21 1.475(6) . ?
C1 C6 1.369(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.369(6) . ?
C21 C20 1.367(6) . ?
C13 C14 1.363(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.417(6) . ?
C19 H19 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.423(6) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 I8 121.3(3) . . ?
C3 C4 I8 120.6(3) . . ?
C3 C4 C5 118.2(4) . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.7(4) . . ?
C27 C26 H26 119.7 . . ?
C27 C24 C23 120.9(4) . . ?
C27 C24 C13 131.7(4) . . ?
C23 C24 C13 107.3(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C17 120.1(4) . . ?
C26 C25 H25 119.5 . . ?
C26 C25 C28 121.0(4) . . ?
C28 C25 H25 119.5 . . ?
F12 C5 C4 120.8(4) . . ?
F12 C5 C6 118.7(3) . . ?
C4 C5 C6 120.5(4) . . ?
C25 C28 H28 120.7 . . ?
C23 C28 C25 118.6(4) . . ?
C23 C28 H28 120.7 . . ?
C26 C27 H27 120.5 . . ?
C24 C27 C26 119.0(4) . . ?
C24 C27 H27 120.5 . . ?
F10 C2 C1 120.4(4) . . ?
F10 C2 C3 118.3(4) . . ?
C3 C2 C1 121.3(4) . . ?
C22 C17 C18 116.1(4) . . ?
C22 C17 C16 115.8(4) . . ?
C16 C17 C18 128.1(4) . . ?
C17 C22 C21 124.0(4) . . ?
C17 C22 C13 124.1(4) . . ?
C13 C22 C21 111.8(4) . . ?
C24 C23 C21 108.5(3) . . ?
C28 C23 C24 119.8(4) . . ?
C28 C23 C21 131.6(4) . . ?
C2 C1 I7 121.5(3) . . ?
C6 C1 I7 120.8(3) . . ?
C6 C1 C2 117.7(4) . . ?
F9 C3 C4 120.8(4) . . ?
F9 C3 C2 118.4(4) . . ?
C4 C3 C2 120.8(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C22 C21 C23 106.0(4) . . ?
C20 C21 C22 118.5(4) . . ?
C20 C21 C23 135.4(4) . . ?
F11 C6 C5 117.5(4) . . ?
F11 C6 C1 121.0(4) . . ?
C1 C6 C5 121.5(4) . . ?
C22 C13 C24 106.3(3) . . ?
C14 C13 C24 134.6(4) . . ?
C14 C13 C22 119.0(4) . . ?
C21 C20 H20 120.6 . . ?
C21 C20 C19 118.7(4) . . ?
C19 C20 H20 120.6 . . ?
C18 C19 C20 122.5(4) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C16 C15 H15 118.8 . . ?
C16 C15 C14 122.3(4) . . ?
C14 C15 H15 118.8 . . ?
C13 C14 C15 118.1(4) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?

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
I8 C4 C5 F12 0.6(5) . . . . ?
I8 C4 C5 C6 -178.2(3) . . . . ?
I8 C4 C3 F9 -1.8(5) . . . . ?
I8 C4 C3 C2 177.2(3) . . . . ?
I7 C1 C6 F11 -0.5(6) . . . . ?
I7 C1 C6 C5 -179.9(3) . . . . ?
F12 C5 C6 F11 0.6(6) . . . . ?
F12 C5 C6 C1 -180.0(4) . . . . ?
F10 C2 C1 I7 0.0(5) . . . . ?
F10 C2 C1 C6 178.6(4) . . . . ?
F10 C2 C3 F9 1.1(6) . . . . ?
F10 C2 C3 C4 -177.9(4) . . . . ?
C4 C5 C6 F11 179.5(4) . . . . ?
C4 C5 C6 C1 -1.1(7) . . . . ?
C26 C25 C28 C23 1.3(6) . . . . ?
C24 C23 C21 C22 -0.2(5) . . . . ?
C24 C23 C21 C20 -176.0(5) . . . . ?
C24 C13 C14 C15 -178.0(4) . . . . ?
C18 C17 C22 C21 2.1(6) . . . . ?
C18 C17 C22 C13 -178.7(4) . . . . ?
C18 C17 C16 C15 179.1(4) . . . . ?
C25 C26 C27 C24 0.1(6) . . . . ?
C25 C28 C23 C24 -0.1(6) . . . . ?
C25 C28 C23 C21 -176.8(4) . . . . ?
C5 C4 C3 F9 178.3(4) . . . . ?
C5 C4 C3 C2 -2.6(6) . . . . ?
C28 C23 C21 C22 176.9(4) . . . . ?
C28 C23 C21 C20 1.1(8) . . . . ?
C27 C26 C25 C28 -1.4(6) . . . . ?
C27 C24 C23 C28 -1.2(6) . . . . ?
C27 C24 C23 C21 176.3(4) . . . . ?
C27 C24 C13 C22 -175.0(4) . . . . ?
C27 C24 C13 C14 3.4(8) . . . . ?
C2 C1 C6 F11 -179.1(4) . . . . ?
C2 C1 C6 C5 1.5(6) . . . . ?
C17 C18 C19 C20 -1.4(6) . . . . ?
C17 C22 C21 C23 -179.3(4) . . . . ?
C17 C22 C21 C20 -2.6(6) . . . . ?
C17 C22 C13 C24 178.6(4) . . . . ?
C17 C22 C13 C14 -0.1(6) . . . . ?
C17 C16 C15 C14 -1.2(6) . . . . ?
C22 C17 C16 C15 1.3(6) . . . . ?
C22 C21 C20 C19 1.0(6) . . . . ?
C22 C13 C14 C15 0.2(6) . . . . ?
C23 C24 C27 C26 1.2(6) . . . . ?
C23 C24 C13 C22 2.0(4) . . . . ?
C23 C24 C13 C14 -179.7(4) . . . . ?
C23 C21 C20 C19 176.4(4) . . . . ?
C1 C2 C3 F9 -177.8(4) . . . . ?
C1 C2 C3 C4 3.2(6) . . . . ?
C3 C4 C5 F12 -179.5(4) . . . . ?
C3 C4 C5 C6 1.6(6) . . . . ?
C3 C2 C1 I7 178.9(3) . . . . ?
C3 C2 C1 C6 -2.5(6) . . . . ?
C16 C17 C22 C21 -179.8(4) . . . . ?
C16 C17 C22 C13 -0.7(6) . . . . ?
C16 C15 C14 C13 0.4(6) . . . . ?
C21 C22 C13 C24 -2.1(5) . . . . ?
C21 C22 C13 C14 179.2(4) . . . . ?
C21 C20 C19 C18 0.9(6) . . . . ?
C13 C24 C27 C26 177.8(4) . . . . ?
C13 C24 C23 C28 -178.6(4) . . . . ?
C13 C24 C23 C21 -1.1(4) . . . . ?
C13 C22 C21 C23 1.5(5) . . . . ?
C13 C22 C21 C20 178.1(4) . . . . ?
C19 C18 C17 C22 -0.1(6) . . . . ?
C19 C18 C17 C16 -177.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_20161202a
_database_code_depnum_ccdc_archive 'CCDC 1547633'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br2 C6 F4), 2(C16 H10)'
_chemical_formula_sum            'C44 H20 Br4 F8'
_chemical_formula_weight         1020.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1Br1
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4059(8)
_cell_length_b                   8.0966(9)
_cell_length_c                   29.6317(13)
_cell_angle_alpha                88.510(6)
_cell_angle_beta                 88.482(6)
_cell_angle_gamma                88.186(9)
_cell_volume                     1774.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6386
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1840
_cell_measurement_theta_min      3.9320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1098
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8538
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.851
_diffrn_reflns_theta_min         3.296
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  57.00   1.00   10.00    --   12.76  37.00 120.00   47
  2  ω    -16.00  85.00   1.00   10.00    --   12.76  77.00 150.00  101
  3  ω    -20.00  54.00   1.00   10.00    --   12.76 -99.00   0.00   74
  4  ω     15.00  54.00   1.00   10.00    --   12.76 -99.00 -90.00   39
  5  ω    -54.00  32.00   1.00   10.00    --   12.76 -37.00-120.00   86
  6  ω    -59.00 -28.00   1.00   10.00    --   12.76 -37.00-150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0778604000
_diffrn_orient_matrix_UB_12      -0.0516587000
_diffrn_orient_matrix_UB_13      -0.0037537000
_diffrn_orient_matrix_UB_21      -0.0328330000
_diffrn_orient_matrix_UB_22      -0.0576915000
_diffrn_orient_matrix_UB_23      0.0164023000
_diffrn_orient_matrix_UB_31      -0.0452921000
_diffrn_orient_matrix_UB_32      -0.0410590000
_diffrn_orient_matrix_UB_33      -0.0170473000
_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                6311
_reflns_number_total             8538
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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         2.973
_refine_diff_density_min         -2.507
_refine_diff_density_rms         0.382
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         8538
_refine_ls_number_restraints     312
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.1096
_refine_ls_restrained_S_all      1.084
_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)+(0.0516P)²+81.3779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3018
_refine_ls_wR_factor_ref         0.3162
_refine_special_details          
;
 Refined as a 4-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.61(14) 0.13(8) 0.13(8) 0.13(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq,
Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim
Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F5) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22),
 C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C36(H36),
  C37(H37), C38(H38), C42(H42), C43(H43), C44(H44)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.14511(19) 0.3472(2) 0.72234(4) 0.0212(3) Uani 1 1 d . . . . .
Br2 Br 0.00153(19) -0.01147(18) 0.67459(5) 0.0217(3) Uani 1 1 d . . . . .
C1 C -0.0637(17) 0.3368(17) 0.6621(4) 0.014(3) Uani 1 1 d . U . . .
C2 C 0.0059(18) 0.1928(17) 0.6434(4) 0.013(2) Uani 1 1 d . U . . .
C3 C 0.0779(18) 0.1959(18) 0.5996(5) 0.017(3) Uani 1 1 d . U . . .
C4 C 0.0747(18) 0.343(2) 0.5742(5) 0.019(3) Uani 1 1 d . U . . .
C5 C 0.000(2) 0.4864(19) 0.5924(5) 0.020(3) Uani 1 1 d . U . . .
C6 C -0.0648(19) 0.4827(18) 0.6367(5) 0.017(3) Uani 1 1 d . U . . .
F1 F 0.1456(12) 0.0598(12) 0.5809(3) 0.027(2) Uani 1 1 d . U . . .
F2 F 0.1423(12) 0.3443(13) 0.5324(3) 0.029(2) Uani 1 1 d . U . . .
F3 F -0.0041(13) 0.6261(13) 0.5678(3) 0.032(2) Uani 1 1 d . U . . .
F4 F -0.1330(12) 0.6247(11) 0.6539(3) 0.027(2) Uani 1 1 d . U . . .
Br3 Br 0.00804(19) 1.10510(18) 0.93882(4) 0.0181(3) Uani 1 1 d . . . . .
Br4 Br 0.13818(18) 1.15824(18) 0.82912(5) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.0030(17) 0.9340(16) 0.8976(4) 0.012(2) Uani 1 1 d . U . . .
C8 C 0.0624(18) 0.9532(17) 0.8523(4) 0.014(3) Uani 1 1 d . U . . .
C9 C 0.0597(17) 0.8205(18) 0.8248(4) 0.016(3) Uani 1 1 d . U . . .
C10 C 0.0000(18) 0.6686(18) 0.8392(5) 0.017(3) Uani 1 1 d . U . . .
C11 C -0.0659(19) 0.6523(19) 0.8838(5) 0.021(3) Uani 1 1 d . U . . .
C12 C -0.0606(17) 0.7824(17) 0.9122(4) 0.015(3) Uani 1 1 d . U . . .
F5 F 0.1219(12) 0.8371(12) 0.7813(3) 0.0234(19) Uani 1 1 d . U . . .
F6 F 0.0023(14) 0.5430(12) 0.8131(3) 0.032(2) Uani 1 1 d . U . . .
F7 F -0.1250(13) 0.5070(11) 0.8985(3) 0.031(2) Uani 1 1 d . U . . .
F8 F -0.1240(11) 0.7623(12) 0.9549(3) 0.0233(19) Uani 1 1 d . U . . .
C13 C 0.5981(19) 0.1604(18) 0.5961(5) 0.018(3) Uani 1 1 d . U . . .
C14 C 0.6722(18) 0.0147(18) 0.5789(4) 0.016(3) Uani 1 1 d . U . . .
H14 H 0.6750 -0.0831 0.5961 0.019 Uiso 1 1 calc R . . . .
C15 C 0.744(2) 0.0211(19) 0.5338(5) 0.022(3) Uani 1 1 d . U . . .
H15 H 0.7959 -0.0738 0.5213 0.026 Uiso 1 1 calc R . . . .
C16 C 0.7366(19) 0.1694(19) 0.5081(4) 0.018(3) Uani 1 1 d . U . . .
H16 H 0.7798 0.1694 0.4783 0.021 Uiso 1 1 calc R . . . .
C17 C 0.6678(19) 0.3147(18) 0.5256(4) 0.016(3) Uani 1 1 d . U . . .
H17 H 0.6700 0.4133 0.5088 0.019 Uiso 1 1 calc R . . . .
C18 C 0.5944(18) 0.3090(17) 0.5696(4) 0.014(3) Uani 1 1 d . U . . .
C19 C 0.5083(17) 0.4423(17) 0.5982(4) 0.013(2) Uani 1 1 d . U . . .
C20 C 0.4703(18) 0.6075(18) 0.5916(5) 0.017(3) Uani 1 1 d . U . . .
H20 H 0.4998 0.6613 0.5644 0.020 Uiso 1 1 calc R . . . .
C21 C 0.3830(18) 0.6945(19) 0.6281(5) 0.019(3) Uani 1 1 d . U . . .
H21 H 0.3527 0.8061 0.6240 0.023 Uiso 1 1 calc R . . . .
C22 C 0.3427(17) 0.6192(18) 0.6689(4) 0.015(3) Uani 1 1 d . U . . .
H22 H 0.2895 0.6804 0.6921 0.018 Uiso 1 1 calc R . . . .
C23 C 0.3818(18) 0.4492(17) 0.6758(4) 0.014(3) Uani 1 1 d . U . . .
C24 C 0.4662(17) 0.3657(17) 0.6400(4) 0.013(2) Uani 1 1 d . U . . .
C25 C 0.5154(17) 0.1950(17) 0.6412(4) 0.013(2) Uani 1 1 d . U . . .
C26 C 0.4796(18) 0.1020(18) 0.6789(4) 0.016(3) Uani 1 1 d . U . . .
H26 H 0.5102 -0.0103 0.6805 0.019 Uiso 1 1 calc R . . . .
C27 C 0.3920(18) 0.1853(18) 0.7164(5) 0.017(3) Uani 1 1 d . U . . .
H27 H 0.3643 0.1235 0.7424 0.020 Uiso 1 1 calc R . . . .
C28 C 0.3483(17) 0.3476(17) 0.7156(4) 0.013(2) Uani 1 1 d . U . . .
H28 H 0.2956 0.3952 0.7412 0.016 Uiso 1 1 calc R . . . .
C29 C 0.4174(18) 0.7861(17) 0.9250(4) 0.013(2) Uani 1 1 d . U . . .
C30 C 0.3581(17) 0.7784(18) 0.9706(4) 0.013(2) Uani 1 1 d . U . . .
H30 H 0.3658 0.8700 0.9887 0.016 Uiso 1 1 calc R . . . .
C31 C 0.289(2) 0.6337(19) 0.9882(5) 0.021(3) Uani 1 1 d . U . . .
H31 H 0.2486 0.6283 1.0182 0.025 Uiso 1 1 calc R . . . .
C32 C 0.2773(19) 0.4947(18) 0.9614(4) 0.017(3) Uani 1 1 d . U . . .
H32 H 0.2307 0.3977 0.9738 0.021 Uiso 1 1 calc R . . . .
C33 C 0.3367(19) 0.5009(19) 0.9155(5) 0.020(3) Uani 1 1 d . U . . .
H33 H 0.3277 0.4103 0.8971 0.024 Uiso 1 1 calc R . . . .
C34 C 0.4072(17) 0.6443(17) 0.8993(4) 0.013(2) Uani 1 1 d . U . . .
C35 C 0.4842(17) 0.6896(17) 0.8535(4) 0.012(2) Uani 1 1 d . U . . .
C36 C 0.5113(18) 0.6090(19) 0.8136(5) 0.019(3) Uani 1 1 d . U . . .
H36 H 0.4799 0.4993 0.8111 0.022 Uiso 1 1 calc R . . . .
C37 C 0.5886(19) 0.6977(19) 0.7762(5) 0.020(3) Uani 1 1 d . U . . .
H37 H 0.6081 0.6434 0.7491 0.023 Uiso 1 1 calc R . . . .
C38 C 0.6353(18) 0.8591(19) 0.7782(4) 0.017(3) Uani 1 1 d . U . . .
H38 H 0.6851 0.9122 0.7528 0.020 Uiso 1 1 calc R . . . .
C39 C 0.6081(18) 0.9466(18) 0.8192(5) 0.017(3) Uani 1 1 d . U . . .
C40 C 0.5305(16) 0.8555(16) 0.8551(4) 0.011(2) Uani 1 1 d . U . . .
C41 C 0.4966(17) 0.9214(17) 0.8987(4) 0.013(2) Uani 1 1 d . U . . .
C42 C 0.5355(18) 1.0827(17) 0.9057(4) 0.014(3) Uani 1 1 d . U . . .
H42 H 0.5118 1.1296 0.9336 0.017 Uiso 1 1 calc R . . . .
C43 C 0.6130(18) 1.1773(18) 0.8694(5) 0.018(3) Uani 1 1 d . U . . .
H43 H 0.6409 1.2866 0.8741 0.021 Uiso 1 1 calc R . . . .
C44 C 0.6474(19) 1.1129(19) 0.8281(5) 0.019(3) Uani 1 1 d . U . . .
H44 H 0.6976 1.1790 0.8052 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.873(13) . ?
Br2 C2 1.874(13) . ?
C1 C2 1.383(19) . ?
C1 C6 1.384(19) . ?
C2 C3 1.391(18) . ?
C3 C4 1.39(2) . ?
C3 F1 1.325(16) . ?
C4 C5 1.38(2) . ?
C4 F2 1.323(15) . ?
C5 C6 1.386(19) . ?
C5 F3 1.329(17) . ?
C6 F4 1.349(17) . ?
Br3 C7 1.873(13) . ?
Br4 C8 1.877(14) . ?
C7 C8 1.407(17) . ?
C7 C12 1.384(19) . ?
C8 C9 1.37(2) . ?
C9 C10 1.37(2) . ?
C9 F5 1.362(15) . ?
C10 C11 1.40(2) . ?
C10 F6 1.292(17) . ?
C11 C12 1.37(2) . ?
C11 F7 1.327(17) . ?
C12 F8 1.345(15) . ?
C13 C14 1.39(2) . ?
C13 C18 1.419(19) . ?
C13 C25 1.483(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.424(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.41(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.38(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.399(17) . ?
C18 C19 1.505(19) . ?
C19 C20 1.37(2) . ?
C19 C24 1.402(17) . ?
C20 H20 0.9300 . ?
C20 C21 1.44(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(19) . ?
C22 H22 0.9300 . ?
C22 C23 1.41(2) . ?
C23 C24 1.396(18) . ?
C23 C28 1.439(17) . ?
C24 C25 1.418(19) . ?
C25 C26 1.356(18) . ?
C26 H26 0.9300 . ?
C26 C27 1.443(19) . ?
C27 H27 0.9300 . ?
C27 C28 1.34(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.412(17) . ?
C29 C34 1.398(19) . ?
C29 C41 1.456(19) . ?
C30 H30 0.9300 . ?
C30 C31 1.38(2) . ?
C31 H31 0.9300 . ?
C31 C32 1.40(2) . ?
C32 H32 0.9300 . ?
C32 C33 1.420(19) . ?
C33 H33 0.9300 . ?
C33 C34 1.36(2) . ?
C34 C35 1.500(17) . ?
C35 C36 1.373(19) . ?
C35 C40 1.399(19) . ?
C36 H36 0.9300 . ?
C36 C37 1.42(2) . ?
C37 H37 0.9300 . ?
C37 C38 1.37(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.427(19) . ?
C39 C40 1.401(18) . ?
C39 C44 1.42(2) . ?
C40 C41 1.424(17) . ?
C41 C42 1.368(19) . ?
C42 H42 0.9300 . ?
C42 C43 1.424(19) . ?
C43 H43 0.9300 . ?
C43 C44 1.36(2) . ?
C44 H44 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 122.6(10) . . ?
C2 C1 C6 119.8(12) . . ?
C6 C1 Br1 117.5(11) . . ?
C1 C2 Br2 122.3(10) . . ?
C1 C2 C3 119.9(12) . . ?
C3 C2 Br2 117.8(10) . . ?
C2 C3 C4 119.8(13) . . ?
F1 C3 C2 121.2(12) . . ?
F1 C3 C4 119.0(12) . . ?
C5 C4 C3 120.4(13) . . ?
F2 C4 C3 119.1(14) . . ?
F2 C4 C5 120.5(14) . . ?
C4 C5 C6 119.1(13) . . ?
F3 C5 C4 120.0(13) . . ?
F3 C5 C6 120.9(14) . . ?
C1 C6 C5 121.0(13) . . ?
F4 C6 C1 121.0(12) . . ?
F4 C6 C5 118.0(13) . . ?
C8 C7 Br3 122.5(10) . . ?
C12 C7 Br3 118.8(10) . . ?
C12 C7 C8 118.6(12) . . ?
C7 C8 Br4 121.1(10) . . ?
C9 C8 Br4 120.0(10) . . ?
C9 C8 C7 118.9(13) . . ?
C8 C9 C10 123.0(13) . . ?
F5 C9 C8 119.1(13) . . ?
F5 C9 C10 117.9(13) . . ?
C9 C10 C11 117.7(13) . . ?
F6 C10 C9 122.4(13) . . ?
F6 C10 C11 119.9(14) . . ?
C12 C11 C10 120.1(14) . . ?
F7 C11 C10 118.9(14) . . ?
F7 C11 C12 120.9(13) . . ?
C11 C12 C7 121.6(13) . . ?
F8 C12 C7 119.8(12) . . ?
F8 C12 C11 118.6(13) . . ?
C14 C13 C18 120.9(13) . . ?
C14 C13 C25 130.5(13) . . ?
C18 C13 C25 108.6(12) . . ?
C13 C14 H14 121.4 . . ?
C13 C14 C15 117.3(13) . . ?
C15 C14 H14 121.4 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(14) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(12) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 121.2 . . ?
C16 C17 C18 117.7(13) . . ?
C18 C17 H17 121.2 . . ?
C13 C18 C19 107.5(11) . . ?
C17 C18 C13 121.4(13) . . ?
C17 C18 C19 131.1(12) . . ?
C20 C19 C18 134.3(12) . . ?
C20 C19 C24 119.8(12) . . ?
C24 C19 C18 105.8(11) . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.5(12) . . ?
C21 C20 H20 121.3 . . ?
C20 C21 H21 118.8 . . ?
C22 C21 C20 122.4(13) . . ?
C22 C21 H21 118.8 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(13) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C28 128.6(13) . . ?
C24 C23 C22 116.9(12) . . ?
C24 C23 C28 114.5(12) . . ?
C19 C24 C25 112.4(12) . . ?
C23 C24 C19 123.2(13) . . ?
C23 C24 C25 124.4(12) . . ?
C24 C25 C13 105.7(11) . . ?
C26 C25 C13 134.5(13) . . ?
C26 C25 C24 119.8(12) . . ?
C25 C26 H26 121.6 . . ?
C25 C26 C27 116.9(13) . . ?
C27 C26 H26 121.6 . . ?
C26 C27 H27 118.3 . . ?
C28 C27 C26 123.4(13) . . ?
C28 C27 H27 118.3 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.1(12) . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C41 130.1(12) . . ?
C34 C29 C30 118.4(12) . . ?
C34 C29 C41 111.4(11) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 C29 119.3(13) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.9(13) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.3(13) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 121.2 . . ?
C34 C33 C32 117.5(14) . . ?
C34 C33 H33 121.2 . . ?
C29 C34 C35 105.8(12) . . ?
C33 C34 C29 123.5(12) . . ?
C33 C34 C35 130.7(13) . . ?
C36 C35 C34 135.1(13) . . ?
C36 C35 C40 118.5(12) . . ?
C40 C35 C34 106.4(11) . . ?
C35 C36 H36 120.9 . . ?
C35 C36 C37 118.2(14) . . ?
C37 C36 H36 120.9 . . ?
C36 C37 H37 118.6 . . ?
C38 C37 C36 122.9(13) . . ?
C38 C37 H37 118.6 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.3(13) . . ?
C39 C38 H38 119.9 . . ?
C40 C39 C38 115.2(13) . . ?
C40 C39 C44 116.1(13) . . ?
C44 C39 C38 128.7(13) . . ?
C35 C40 C39 125.0(12) . . ?
C35 C40 C41 112.0(11) . . ?
C39 C40 C41 123.0(13) . . ?
C40 C41 C29 104.4(12) . . ?
C42 C41 C29 136.7(12) . . ?
C42 C41 C40 118.9(12) . . ?
C41 C42 H42 120.6 . . ?
C41 C42 C43 118.7(12) . . ?
C43 C42 H42 120.6 . . ?
C42 C43 H43 119.0 . . ?
C44 C43 C42 122.0(14) . . ?
C44 C43 H43 119.0 . . ?
C39 C44 H44 119.4 . . ?
C43 C44 C39 121.2(13) . . ?
C43 C44 H44 119.4 . . ?

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 Br2 7.1(16) . . . . ?
Br1 C1 C2 C3 -174.7(10) . . . . ?
Br1 C1 C6 C5 177.3(11) . . . . ?
Br1 C1 C6 F4 -4.2(17) . . . . ?
Br2 C2 C3 C4 176.4(10) . . . . ?
Br2 C2 C3 F1 -1.8(18) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
C1 C2 C3 F1 179.9(12) . . . . ?
C2 C1 C6 C5 1(2) . . . . ?
C2 C1 C6 F4 179.5(12) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C2 C3 C4 F2 -179.4(12) . . . . ?
C3 C4 C5 C6 2(2) . . . . ?
C3 C4 C5 F3 -179.2(12) . . . . ?
C4 C5 C6 C1 -3(2) . . . . ?
C4 C5 C6 F4 178.5(12) . . . . ?
C6 C1 C2 Br2 -176.8(10) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
F1 C3 C4 C5 178.2(12) . . . . ?
F1 C3 C4 F2 -1(2) . . . . ?
F2 C4 C5 C6 -178.2(12) . . . . ?
F2 C4 C5 F3 0(2) . . . . ?
F3 C5 C6 C1 178.7(12) . . . . ?
F3 C5 C6 F4 0(2) . . . . ?
Br3 C7 C8 Br4 -3.9(16) . . . . ?
Br3 C7 C8 C9 177.9(10) . . . . ?
Br3 C7 C12 C11 -179.3(10) . . . . ?
Br3 C7 C12 F8 2.7(17) . . . . ?
Br4 C8 C9 C10 -177.7(10) . . . . ?
Br4 C8 C9 F5 3.7(16) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C7 C8 C9 F5 -178.2(11) . . . . ?
C8 C7 C12 C11 0(2) . . . . ?
C8 C7 C12 F8 -177.8(11) . . . . ?
C8 C9 C10 C11 2.0(19) . . . . ?
C8 C9 C10 F6 -178.2(12) . . . . ?
C9 C10 C11 C12 -3(2) . . . . ?
C9 C10 C11 F7 179.7(12) . . . . ?
C10 C11 C12 C7 2(2) . . . . ?
C10 C11 C12 F8 -179.6(12) . . . . ?
C12 C7 C8 Br4 176.5(10) . . . . ?
C12 C7 C8 C9 -1.7(19) . . . . ?
F5 C9 C10 C11 -179.3(11) . . . . ?
F5 C9 C10 F6 0.4(19) . . . . ?
F6 C10 C11 C12 176.9(12) . . . . ?
F6 C10 C11 F7 0(2) . . . . ?
F7 C11 C12 C7 179.1(12) . . . . ?
F7 C11 C12 F8 -3(2) . . . . ?
C13 C14 C15 C16 -1(2) . . . . ?
C13 C18 C19 C20 179.2(15) . . . . ?
C13 C18 C19 C24 0.1(15) . . . . ?
C13 C25 C26 C27 -178.8(14) . . . . ?
C14 C13 C18 C17 -1(2) . . . . ?
C14 C13 C18 C19 -179.3(12) . . . . ?
C14 C13 C25 C24 179.0(14) . . . . ?
C14 C13 C25 C26 -2(3) . . . . ?
C14 C15 C16 C17 3(2) . . . . ?
C15 C16 C17 C18 -4(2) . . . . ?
C16 C17 C18 C13 3(2) . . . . ?
C16 C17 C18 C19 -179.5(13) . . . . ?
C17 C18 C19 C20 1(3) . . . . ?
C17 C18 C19 C24 -177.8(14) . . . . ?
C18 C13 C14 C15 0(2) . . . . ?
C18 C13 C25 C24 -0.5(15) . . . . ?
C18 C13 C25 C26 178.2(15) . . . . ?
C18 C19 C20 C21 179.4(14) . . . . ?
C18 C19 C24 C23 -179.2(12) . . . . ?
C18 C19 C24 C25 -0.5(15) . . . . ?
C19 C20 C21 C22 2(2) . . . . ?
C19 C24 C25 C13 0.6(15) . . . . ?
C19 C24 C25 C26 -178.4(12) . . . . ?
C20 C19 C24 C23 2(2) . . . . ?
C20 C19 C24 C25 -179.7(12) . . . . ?
C20 C21 C22 C23 -2(2) . . . . ?
C21 C22 C23 C24 1.7(19) . . . . ?
C21 C22 C23 C28 -179.1(13) . . . . ?
C22 C23 C24 C19 -1.5(19) . . . . ?
C22 C23 C24 C25 179.9(12) . . . . ?
C22 C23 C28 C27 179.0(14) . . . . ?
C23 C24 C25 C13 179.3(12) . . . . ?
C23 C24 C25 C26 0(2) . . . . ?
C24 C19 C20 C21 -1.6(19) . . . . ?
C24 C23 C28 C27 -1.8(19) . . . . ?
C24 C25 C26 C27 -0.2(19) . . . . ?
C25 C13 C14 C15 -179.4(14) . . . . ?
C25 C13 C18 C17 178.4(12) . . . . ?
C25 C13 C18 C19 0.2(15) . . . . ?
C25 C26 C27 C28 -1(2) . . . . ?
C26 C27 C28 C23 2(2) . . . . ?
C28 C23 C24 C19 179.2(12) . . . . ?
C28 C23 C24 C25 0.6(19) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C29 C34 C35 C36 -179.3(15) . . . . ?
C29 C34 C35 C40 -1.3(13) . . . . ?
C29 C41 C42 C43 -178.8(14) . . . . ?
C30 C29 C34 C33 3(2) . . . . ?
C30 C29 C34 C35 -178.3(11) . . . . ?
C30 C29 C41 C40 179.3(13) . . . . ?
C30 C29 C41 C42 -3(3) . . . . ?
C30 C31 C32 C33 0(2) . . . . ?
C31 C32 C33 C34 1(2) . . . . ?
C32 C33 C34 C29 -3(2) . . . . ?
C32 C33 C34 C35 178.6(12) . . . . ?
C33 C34 C35 C36 0(2) . . . . ?
C33 C34 C35 C40 177.7(13) . . . . ?
C34 C29 C30 C31 -1.4(19) . . . . ?
C34 C29 C41 C40 1.4(14) . . . . ?
C34 C29 C41 C42 178.7(14) . . . . ?
C34 C35 C36 C37 179.1(13) . . . . ?
C34 C35 C40 C39 179.7(12) . . . . ?
C34 C35 C40 C41 2.2(14) . . . . ?
C35 C36 C37 C38 -1(2) . . . . ?
C35 C40 C41 C29 -2.2(14) . . . . ?
C35 C40 C41 C42 179.8(11) . . . . ?
C36 C35 C40 C39 -1.9(19) . . . . ?
C36 C35 C40 C41 -179.3(11) . . . . ?
C36 C37 C38 C39 0(2) . . . . ?
C37 C38 C39 C40 -0.7(19) . . . . ?
C37 C38 C39 C44 180.0(14) . . . . ?
C38 C39 C40 C35 1.6(19) . . . . ?
C38 C39 C40 C41 178.7(12) . . . . ?
C38 C39 C44 C43 -179.9(14) . . . . ?
C39 C40 C41 C29 -179.7(12) . . . . ?
C39 C40 C41 C42 2.4(19) . . . . ?
C40 C35 C36 C37 1.3(19) . . . . ?
C40 C39 C44 C43 0.8(19) . . . . ?
C40 C41 C42 C43 -1.7(18) . . . . ?
C41 C29 C30 C31 -179.3(13) . . . . ?
C41 C29 C34 C33 -179.1(12) . . . . ?
C41 C29 C34 C35 -0.1(14) . . . . ?
C41 C42 C43 C44 1(2) . . . . ?
C42 C43 C44 C39 0(2) . . . . ?
C44 C39 C40 C35 -179.0(12) . . . . ?
C44 C39 C40 C41 -1.9(19) . . . . ?

_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 2.452
_oxdiff_exptl_absorpt_empirical_full_min 0.555
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.61(14)
2 0.13(8)
3 0.13(8)
4 0.13(8)

####################################################################### 
# 
# 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_20161228b
_database_code_depnum_ccdc_archive 'CCDC 1547629'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 I2, C16 H10'
_chemical_formula_sum            'C22 H10 F4 I2'
_chemical_formula_weight         604.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1i1
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                   15.2963(3)
_cell_length_b                   18.1009(4)
_cell_length_c                   30.4800(5)
_cell_angle_alpha                99.2518(16)
_cell_angle_beta                 90.4052(15)
_cell_angle_gamma                114.420(2)
_cell_volume                     7558.8(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    66605
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.6660
_cell_measurement_theta_min      3.5980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4544
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            75567
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.937
_diffrn_reflns_theta_min         3.163
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  25.00   1.00   10.00    --   12.76 -57.00 -30.00   52
  2  ω    -11.00  53.00   1.00   10.00    --   12.76 -99.00  60.00   64
  3  ω    -11.00  29.00   1.00   10.00    --  -11.04 -99.00  90.00   40
  4  ω    -15.00  13.00   1.00   10.00    --   12.76 -37.00  60.00   28
  5  ω    -12.00  71.00   1.00   10.00    --   12.76  37.00 -60.00   83
  6  ω    -21.00  88.00   1.00   10.00    --   12.76  19.00-150.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0256758000
_diffrn_orient_matrix_UB_12      -0.0228290000
_diffrn_orient_matrix_UB_13      -0.0207482000
_diffrn_orient_matrix_UB_21      -0.0240828000
_diffrn_orient_matrix_UB_22      0.0262020000
_diffrn_orient_matrix_UB_23      0.0005532000
_diffrn_orient_matrix_UB_31      0.0370341000
_diffrn_orient_matrix_UB_32      0.0265768000
_diffrn_orient_matrix_UB_33      -0.0113520000
_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                28572
_reflns_number_total             36197
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.457
_refine_diff_density_min         -3.125
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2017
_refine_ls_number_reflns         36197
_refine_ls_number_restraints     1056
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0144P)²+7.1132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq,
Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50)
\\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq,
Uanis(C54) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C57)
\\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq,
Uanis(C61) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64)
\\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C67) \\sim Ueq,
Uanis(C68) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C71)
\\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C74) \\sim Ueq,
Uanis(C75) \\sim Ueq, Uanis(C76) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C78)
\\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C81) \\sim Ueq,
Uanis(C82) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C84) \\sim Ueq, Uanis(C85)
\\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87) \\sim Ueq, Uanis(C88) \\sim Ueq,
Uanis(C89) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C92)
\\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C94) \\sim Ueq, Uanis(C95) \\sim Ueq,
Uanis(C96) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C99)
\\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C102) \\sim Ueq,
Uanis(C103) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C105) \\sim Ueq,
Uanis(C106) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C108) \\sim Ueq,
Uanis(C109) \\sim Ueq, Uanis(C110) \\sim Ueq, Uanis(C111) \\sim Ueq,
Uanis(C112) \\sim Ueq, Uanis(C113) \\sim Ueq, Uanis(C114) \\sim Ueq,
Uanis(C115) \\sim Ueq, Uanis(C116) \\sim Ueq, Uanis(C117) \\sim Ueq,
Uanis(C118) \\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C120) \\sim Ueq,
Uanis(C121) \\sim Ueq, Uanis(C122) \\sim Ueq, Uanis(C123) \\sim Ueq,
Uanis(C124) \\sim Ueq, Uanis(C125) \\sim Ueq, Uanis(C126) \\sim Ueq,
Uanis(C127) \\sim Ueq, Uanis(C128) \\sim Ueq, Uanis(C129) \\sim Ueq,
Uanis(C130) \\sim Ueq, Uanis(C131) \\sim Ueq, Uanis(C132) \\sim Ueq,
Uanis(C133) \\sim Ueq, Uanis(C134) \\sim Ueq, Uanis(C135) \\sim Ueq,
Uanis(C136) \\sim Ueq, Uanis(C137) \\sim Ueq, Uanis(C138) \\sim Ueq,
Uanis(C139) \\sim Ueq, Uanis(C140) \\sim Ueq, Uanis(C141) \\sim Ueq,
Uanis(C142) \\sim Ueq, Uanis(C143) \\sim Ueq, Uanis(C144) \\sim Ueq,
Uanis(C145) \\sim Ueq, Uanis(C146) \\sim Ueq, Uanis(C147) \\sim Ueq,
Uanis(C148) \\sim Ueq, Uanis(C149) \\sim Ueq, Uanis(C150) \\sim Ueq,
Uanis(C151) \\sim Ueq, Uanis(C152) \\sim Ueq, Uanis(C153) \\sim Ueq,
Uanis(C154) \\sim Ueq, Uanis(C155) \\sim Ueq, Uanis(C156) \\sim Ueq,
Uanis(C157) \\sim Ueq, Uanis(C158) \\sim Ueq, Uanis(C159) \\sim Ueq,
Uanis(C160) \\sim Ueq, Uanis(C161) \\sim Ueq, Uanis(C162) \\sim Ueq,
Uanis(C163) \\sim Ueq, Uanis(C164) \\sim Ueq, Uanis(C165) \\sim Ueq,
Uanis(C166) \\sim Ueq, Uanis(C167) \\sim Ueq, Uanis(C168) \\sim Ueq,
Uanis(C169) \\sim Ueq, Uanis(C170) \\sim Ueq, Uanis(C171) \\sim Ueq,
Uanis(C172) \\sim Ueq, Uanis(C173) \\sim Ueq, Uanis(C174) \\sim Ueq,
Uanis(C175) \\sim Ueq, Uanis(C176) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C50(H50), C51(H51), C52(H52), C53(H53), C56(H56), C57(H57), C58(H58),
 C60(H60), C61(H61), C62(H62), C66(H66), C67(H67), C68(H68), C69(H69), C72(H72),
  C73(H73), C74(H74), C76(H76), C77(H77), C78(H78), C82(H82), C83(H83),
 C84(H84), C85(H85), C88(H88), C89(H89), C90(H90), C92(H92), C93(H93), C94(H94),
  C98(H98), C99(H99), C100(H100), C101(H101), C104(H104), C105(H105),
 C106(H106), C108(H108), C109(H109), C110(H110), C114(H114), C115(H115),
 C116(H116), C117(H117), C120(H120), C121(H121), C122(H122), C124(H124),
 C125(H125), C126(H126), C130(H130), C131(H131), C132(H132), C133(H133),
 C136(H136), C137(H137), C138(H138), C140(H140), C141(H141), C142(H142),
 C146(H146), C147(H147), C148(H148), C149(H149), C152(H152), C153(H153),
 C154(H154), C156(H156), C157(H157), C158(H158), C162(H162), C163(H163),
 C164(H164), C165(H165), C168(H168), C169(H169), C170(H170), C172(H172),
 C173(H173), C174(H174)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.7099(3) 1.0382(3) 0.38716(14) 0.0190(10) Uani 1 1 d . U . . .
C2 C 0.7876(3) 1.0245(3) 0.36927(14) 0.0188(10) Uani 1 1 d . U . . .
C3 C 0.7705(3) 0.9481(3) 0.34499(14) 0.0196(10) Uani 1 1 d . U . . .
C4 C 0.6805(4) 0.8845(3) 0.33848(14) 0.0212(10) Uani 1 1 d . U . . .
C5 C 0.6041(3) 0.8975(3) 0.35610(15) 0.0241(11) Uani 1 1 d . U . . .
C6 C 0.6198(3) 0.9740(3) 0.38024(14) 0.0207(10) Uani 1 1 d . U . . .
C7 C 0.2631(3) 0.0662(3) 0.38571(13) 0.0183(10) Uani 1 1 d . U . . .
C8 C 0.3616(3) 0.1076(3) 0.38123(15) 0.0231(10) Uani 1 1 d . U . . .
C9 C 0.4087(3) 0.0648(3) 0.35787(15) 0.0252(11) Uani 1 1 d . U . . .
C10 C 0.3618(4) -0.0172(3) 0.33972(15) 0.0277(12) Uani 1 1 d . U . . .
C11 C 0.2653(4) -0.0584(3) 0.34433(15) 0.0287(12) Uani 1 1 d . U . . .
C12 C 0.2161(4) -0.0166(3) 0.36667(15) 0.0261(11) Uani 1 1 d . U . . .
C13 C 0.2535(3) 0.4328(3) 0.12552(14) 0.0207(10) Uani 1 1 d . U . . .
C14 C 0.1622(3) 0.4070(3) 0.10379(14) 0.0206(10) Uani 1 1 d . U . . .
C15 C 0.1224(3) 0.4632(3) 0.10487(14) 0.0214(10) Uani 1 1 d . U . . .
C16 C 0.1693(4) 0.5431(3) 0.12797(15) 0.0242(11) Uani 1 1 d . U . . .
C17 C 0.2591(4) 0.5685(3) 0.14865(15) 0.0250(11) Uani 1 1 d . U . . .
C18 C 0.3003(3) 0.5134(3) 0.14734(14) 0.0216(10) Uani 1 1 d . U . . .
C19 C 0.2522(3) 0.4608(3) 0.37683(13) 0.0200(10) Uani 1 1 d . U . . .
C20 C 0.1579(3) 0.4402(3) 0.36073(14) 0.0218(10) Uani 1 1 d . U . . .
C21 C 0.1305(3) 0.5022(3) 0.35684(14) 0.0227(11) Uani 1 1 d . U . . .
C22 C 0.1937(4) 0.5839(3) 0.36835(14) 0.0214(10) Uani 1 1 d . U . . .
C23 C 0.2867(4) 0.6044(3) 0.38305(14) 0.0220(11) Uani 1 1 d . U . . .
C24 C 0.3159(3) 0.5426(3) 0.38712(14) 0.0201(10) Uani 1 1 d . U . . .
C25 C 0.8109(3) 0.4450(3) 0.13341(14) 0.0195(10) Uani 1 1 d . U . . .
C26 C 0.7406(4) 0.4722(3) 0.12382(15) 0.0276(12) Uani 1 1 d . U . . .
C27 C 0.7574(5) 0.5535(4) 0.13981(18) 0.0384(15) Uani 1 1 d . U . . .
C28 C 0.8417(5) 0.6075(3) 0.16425(17) 0.0374(15) Uani 1 1 d . U . . .
C29 C 0.9106(4) 0.5813(3) 0.17333(15) 0.0294(12) Uani 1 1 d . U . . .
C30 C 0.8957(4) 0.5012(3) 0.15821(14) 0.0217(10) Uani 1 1 d . U . . .
C31 C 0.7873(4) 0.4713(3) 0.38734(14) 0.0201(10) Uani 1 1 d . U . . .
C32 C 0.7303(3) 0.5102(3) 0.37721(14) 0.0197(10) Uani 1 1 d . U . . .
C33 C 0.7694(4) 0.5951(3) 0.38380(14) 0.0214(10) Uani 1 1 d . U . . .
C34 C 0.8633(4) 0.6418(3) 0.40007(14) 0.0209(10) Uani 1 1 d . U . . .
C35 C 0.9213(4) 0.6040(3) 0.41004(15) 0.0252(11) Uani 1 1 d . U . . .
C36 C 0.8819(4) 0.5190(3) 0.40390(14) 0.0239(11) Uani 1 1 d . U . . .
C37 C 0.7017(3) 1.0053(3) 0.12975(14) 0.0192(10) Uani 1 1 d . U . . .
C38 C 0.7776(3) 0.9866(3) 0.11293(14) 0.0203(10) Uani 1 1 d . U . . .
C39 C 0.7613(3) 0.9054(3) 0.09942(14) 0.0221(10) Uani 1 1 d . U . . .
C40 C 0.6723(4) 0.8418(3) 0.10187(15) 0.0227(10) Uani 1 1 d . U . . .
C41 C 0.5986(3) 0.8605(3) 0.11779(14) 0.0236(11) Uani 1 1 d . U . . .
C42 C 0.6139(3) 0.9407(3) 0.13168(14) 0.0225(11) Uani 1 1 d . U . . .
C43 C 0.2640(3) 1.0431(3) 0.13021(14) 0.0207(10) Uani 1 1 d . U . . .
C44 C 0.3579(4) 1.0671(3) 0.11797(14) 0.0221(10) Uani 1 1 d . U . . .
C45 C 0.3869(4) 1.0054(3) 0.10051(14) 0.0214(10) Uani 1 1 d . U . . .
C46 C 0.3284(4) 0.9239(3) 0.09684(14) 0.0232(11) Uani 1 1 d . U . . .
C47 C 0.2352(4) 0.9010(3) 0.10864(14) 0.0222(10) Uani 1 1 d . U . . .
C48 C 0.2043(3) 0.9605(3) 0.12537(14) 0.0232(11) Uani 1 1 d . U . . .
C49 C 0.6874(4) 1.0135(3) 0.51809(15) 0.0249(11) Uani 1 1 d . U . . .
C50 C 0.6400(4) 1.0530(4) 0.54424(17) 0.0357(14) Uani 1 1 d . U . . .
H50 H 0.5735 1.0277 0.5451 0.043 Uiso 1 1 calc R . . . .
C51 C 0.6933(5) 1.1309(4) 0.56897(18) 0.0422(15) Uani 1 1 d . U . . .
H51 H 0.6618 1.1578 0.5864 0.051 Uiso 1 1 calc R . . . .
C52 C 0.7910(5) 1.1691(3) 0.56826(17) 0.0421(15) Uani 1 1 d . U . . .
H52 H 0.8248 1.2215 0.5851 0.050 Uiso 1 1 calc R . . . .
C53 C 0.8411(4) 1.1305(3) 0.54252(16) 0.0331(13) Uani 1 1 d . U . . .
H53 H 0.9079 1.1562 0.5427 0.040 Uiso 1 1 calc R . . . .
C54 C 0.7893(4) 1.0532(3) 0.51679(15) 0.0254(11) Uani 1 1 d . U . . .
C55 C 0.8191(3) 0.9981(3) 0.48614(15) 0.0232(11) Uani 1 1 d . U . . .
C56 C 0.9039(4) 1.0012(3) 0.47033(16) 0.0303(12) Uani 1 1 d . U . . .
H56 H 0.9614 1.0475 0.4795 0.036 Uiso 1 1 calc R . . . .
C57 C 0.9028(4) 0.9329(4) 0.43989(17) 0.0358(14) Uani 1 1 d . U . . .
H57 H 0.9607 0.9350 0.4296 0.043 Uiso 1 1 calc R . . . .
C58 C 0.8201(4) 0.8642(3) 0.42501(17) 0.0334(13) Uani 1 1 d . U . . .
H58 H 0.8227 0.8210 0.4048 0.040 Uiso 1 1 calc R . . . .
C59 C 0.7300(4) 0.8580(3) 0.44014(16) 0.0289(12) Uani 1 1 d . U . . .
C60 C 0.6378(4) 0.7914(3) 0.42919(17) 0.0373(14) Uani 1 1 d . U . . .
H60 H 0.6310 0.7442 0.4094 0.045 Uiso 1 1 calc R . . . .
C61 C 0.5591(4) 0.7966(3) 0.44759(17) 0.0376(14) Uani 1 1 d . U . . .
H61 H 0.4995 0.7519 0.4401 0.045 Uiso 1 1 calc R . . . .
C62 C 0.5641(4) 0.8668(3) 0.47751(18) 0.0356(13) Uani 1 1 d . U . . .
H62 H 0.5088 0.8687 0.4891 0.043 Uiso 1 1 calc R . . . .
C63 C 0.6523(4) 0.9322(3) 0.48912(16) 0.0257(11) Uani 1 1 d . U . . .
C64 C 0.7336(3) 0.9262(3) 0.47036(15) 0.0222(10) Uani 1 1 d . U . . .
C65 C 0.8118(3) 0.4719(3) 0.51330(13) 0.0179(10) Uani 1 1 d . U . . .
C66 C 0.8501(4) 0.4177(3) 0.52048(13) 0.0212(10) Uani 1 1 d . U . . .
H66 H 0.9156 0.4365 0.5281 0.025 Uiso 1 1 calc R . . . .
C67 C 0.7890(4) 0.3346(3) 0.51607(15) 0.0288(12) Uani 1 1 d . U . . .
H67 H 0.8140 0.2973 0.5205 0.035 Uiso 1 1 calc R . . . .
C68 C 0.6919(4) 0.3068(3) 0.50525(15) 0.0259(11) Uani 1 1 d . U . . .
H68 H 0.6520 0.2510 0.5030 0.031 Uiso 1 1 calc R . . . .
C69 C 0.6524(4) 0.3606(3) 0.49761(14) 0.0235(11) Uani 1 1 d . U . . .
H69 H 0.5866 0.3414 0.4905 0.028 Uiso 1 1 calc R . . . .
C70 C 0.7130(3) 0.4435(3) 0.50075(13) 0.0176(10) Uani 1 1 d . U . . .
C71 C 0.6938(3) 0.5149(3) 0.49412(13) 0.0176(10) Uani 1 1 d . U . . .
C72 C 0.6146(4) 0.5259(3) 0.48066(14) 0.0247(11) Uani 1 1 d . U . . .
H72 H 0.5548 0.4814 0.4734 0.030 Uiso 1 1 calc R . . . .
C73 C 0.6267(4) 0.6073(3) 0.47821(15) 0.0310(12) Uani 1 1 d . U . . .
H73 H 0.5735 0.6153 0.4693 0.037 Uiso 1 1 calc R . . . .
C74 C 0.7134(4) 0.6742(3) 0.48840(15) 0.0282(12) Uani 1 1 d . U . . .
H74 H 0.7177 0.7264 0.4868 0.034 Uiso 1 1 calc R . . . .
C75 C 0.7968(4) 0.6649(3) 0.50131(14) 0.0232(11) Uani 1 1 d . U . . .
C76 C 0.8925(4) 0.7260(3) 0.51154(15) 0.0295(12) Uani 1 1 d . U . . .
H76 H 0.9062 0.7805 0.5098 0.035 Uiso 1 1 calc R . . . .
C77 C 0.9652(4) 0.7058(3) 0.52394(15) 0.0281(12) Uani 1 1 d . U . . .
H77 H 1.0271 0.7474 0.5308 0.034 Uiso 1 1 calc R . . . .
C78 C 0.9492(3) 0.6234(3) 0.52676(14) 0.0216(10) Uani 1 1 d . U . . .
H78 H 0.9992 0.6110 0.5356 0.026 Uiso 1 1 calc R . . . .
C79 C 0.8573(3) 0.5629(3) 0.51590(13) 0.0171(10) Uani 1 1 d . U . . .
C80 C 0.7833(3) 0.5844(3) 0.50349(13) 0.0177(10) Uani 1 1 d . U . . .
C81 C 0.6803(3) 1.0072(3) 0.25745(13) 0.0177(10) Uani 1 1 d . U . . .
C82 C 0.6353(4) 1.0549(3) 0.27722(14) 0.0230(10) Uani 1 1 d . U . . .
H82 H 0.5698 1.0307 0.2811 0.028 Uiso 1 1 calc R . . . .
C83 C 0.6882(4) 1.1387(3) 0.29123(16) 0.0324(12) Uani 1 1 d . U . . .
H83 H 0.6580 1.1710 0.3044 0.039 Uiso 1 1 calc R . . . .
C84 C 0.7852(4) 1.1747(3) 0.28589(16) 0.0341(13) Uani 1 1 d . U . . .
H84 H 0.8200 1.2310 0.2960 0.041 Uiso 1 1 calc R . . . .
C85 C 0.8323(4) 1.1286(3) 0.26567(16) 0.0344(13) Uani 1 1 d . U . . .
H85 H 0.8978 1.1538 0.2620 0.041 Uiso 1 1 calc R . . . .
C86 C 0.7804(4) 1.0449(3) 0.25113(14) 0.0231(11) Uani 1 1 d . U . . .
C87 C 0.8088(4) 0.9809(4) 0.22901(15) 0.0353(13) Uani 1 1 d . U . . .
C88 C 0.8923(5) 0.9801(5) 0.21304(18) 0.0566(19) Uani 1 1 d . U . . .
H88 H 0.9485 1.0284 0.2159 0.068 Uiso 1 1 calc R . . . .
C89 C 0.8904(7) 0.9045(6) 0.1923(2) 0.077(2) Uani 1 1 d . U . . .
H89 H 0.9469 0.9038 0.1818 0.093 Uiso 1 1 calc R . . . .
C90 C 0.8118(7) 0.8338(5) 0.1870(2) 0.073(2) Uani 1 1 d . U . . .
H90 H 0.8154 0.7858 0.1727 0.088 Uiso 1 1 calc R . . . .
C91 C 0.7205(6) 0.8291(4) 0.20279(19) 0.0547(18) Uani 1 1 d . U . . .
C92 C 0.6300(7) 0.7630(4) 0.2001(2) 0.065(2) Uani 1 1 d . U . . .
H92 H 0.6230 0.7107 0.1869 0.079 Uiso 1 1 calc R . . . .
C93 C 0.5513(6) 0.7725(4) 0.21613(19) 0.060(2) Uani 1 1 d . U . . .
H93 H 0.4927 0.7265 0.2137 0.072 Uiso 1 1 calc R . . . .
C94 C 0.5570(4) 0.8516(3) 0.23654(16) 0.0387(14) Uani 1 1 d . U . . .
H94 H 0.5030 0.8575 0.2472 0.046 Uiso 1 1 calc R . . . .
C95 C 0.6443(4) 0.9184(3) 0.23984(14) 0.0235(11) Uani 1 1 d . U . . .
C96 C 0.7246(4) 0.9065(3) 0.22322(15) 0.0321(13) Uani 1 1 d . U . . .
C97 C 0.8153(4) 0.6267(3) 0.27523(15) 0.0304(13) Uani 1 1 d . U . . .
C98 C 0.8474(5) 0.7119(4) 0.28718(17) 0.0435(15) Uani 1 1 d . U . . .
H98 H 0.8078 0.7374 0.2816 0.052 Uiso 1 1 calc R . . . .
C99 C 0.9397(5) 0.7577(4) 0.30762(19) 0.0522(18) Uani 1 1 d . U . . .
H99 H 0.9624 0.8147 0.3158 0.063 Uiso 1 1 calc R . . . .
C100 C 0.9982(5) 0.7195(4) 0.31592(19) 0.0554(19) Uani 1 1 d . U . . .
H100 H 1.0597 0.7516 0.3298 0.067 Uiso 1 1 calc R . . . .
C101 C 0.9682(4) 0.6351(4) 0.30430(17) 0.0413(15) Uani 1 1 d . U . . .
H101 H 1.0087 0.6105 0.3102 0.050 Uiso 1 1 calc R . . . .
C102 C 0.8759(4) 0.5878(3) 0.28356(15) 0.0301(12) Uani 1 1 d . U . . .
C103 C 0.8240(4) 0.4998(3) 0.26701(15) 0.0262(11) Uani 1 1 d . U . . .
C104 C 0.8452(4) 0.4309(4) 0.26456(16) 0.0344(13) Uani 1 1 d . U . . .
H104 H 0.9045 0.4361 0.2759 0.041 Uiso 1 1 calc R . . . .
C105 C 0.7739(4) 0.3540(3) 0.24433(16) 0.0356(13) Uani 1 1 d . U . . .
H105 H 0.7870 0.3079 0.2430 0.043 Uiso 1 1 calc R . . . .
C106 C 0.6859(4) 0.3429(3) 0.22640(16) 0.0359(14) Uani 1 1 d . U . . .
H106 H 0.6419 0.2905 0.2129 0.043 Uiso 1 1 calc R . . . .
C107 C 0.6617(4) 0.4109(3) 0.22835(15) 0.0310(12) Uani 1 1 d . U . . .
C108 C 0.5755(4) 0.4116(3) 0.21134(15) 0.0303(12) Uani 1 1 d . U . . .
H108 H 0.5249 0.3626 0.1979 0.036 Uiso 1 1 calc R . . . .
C109 C 0.5671(4) 0.4852(4) 0.21485(16) 0.0351(13) Uani 1 1 d . U . . .
H109 H 0.5106 0.4848 0.2031 0.042 Uiso 1 1 calc R . . . .
C110 C 0.6409(4) 0.5613(4) 0.23565(16) 0.0334(13) Uani 1 1 d . U . . .
H110 H 0.6330 0.6100 0.2377 0.040 Uiso 1 1 calc R . . . .
C111 C 0.7244(4) 0.5620(3) 0.25276(15) 0.0262(11) Uani 1 1 d . U . . .
C112 C 0.7340(4) 0.4865(3) 0.24856(14) 0.0226(11) Uani 1 1 d . U . . .
C113 C 0.3219(3) -0.0278(3) 0.22750(14) 0.0223(10) Uani 1 1 d . U . . .
C114 C 0.3712(4) -0.0726(3) 0.20817(14) 0.0266(11) Uani 1 1 d . U . . .
H114 H 0.4366 -0.0462 0.2045 0.032 Uiso 1 1 calc R . . . .
C115 C 0.3220(4) -0.1569(3) 0.19438(15) 0.0318(12) Uani 1 1 d . U . . .
H115 H 0.3550 -0.1873 0.1821 0.038 Uiso 1 1 calc R . . . .
C116 C 0.2236(4) -0.1969(3) 0.19866(16) 0.0331(13) Uani 1 1 d . U . . .
H116 H 0.1912 -0.2534 0.1883 0.040 Uiso 1 1 calc R . . . .
C117 C 0.1733(4) -0.1531(3) 0.21831(15) 0.0289(12) Uani 1 1 d . U . . .
H117 H 0.1078 -0.1802 0.2216 0.035 Uiso 1 1 calc R . . . .
C118 C 0.2223(4) -0.0683(3) 0.23299(14) 0.0226(11) Uani 1 1 d . U . . .
C119 C 0.1897(4) -0.0062(3) 0.25393(14) 0.0243(11) Uani 1 1 d . U . . .
C120 C 0.1044(4) -0.0076(3) 0.26803(15) 0.0295(12) Uani 1 1 d . U . . .
H120 H 0.0493 -0.0569 0.2646 0.035 Uiso 1 1 calc R . . . .
C121 C 0.1015(4) 0.0681(4) 0.28801(16) 0.0349(13) Uani 1 1 d . U . . .
H121 H 0.0433 0.0674 0.2971 0.042 Uiso 1 1 calc R . . . .
C122 C 0.1812(4) 0.1416(3) 0.29430(15) 0.0326(13) Uani 1 1 d . U . . .
H122 H 0.1763 0.1896 0.3076 0.039 Uiso 1 1 calc R . . . .
C123 C 0.2722(4) 0.1457(3) 0.28059(14) 0.0262(11) Uani 1 1 d . U . . .
C124 C 0.3615(4) 0.2156(3) 0.28422(15) 0.0295(12) Uani 1 1 d . U . . .
H124 H 0.3658 0.2673 0.2970 0.035 Uiso 1 1 calc R . . . .
C125 C 0.4413(4) 0.2074(3) 0.26909(16) 0.0335(13) Uani 1 1 d . U . . .
H125 H 0.4995 0.2541 0.2722 0.040 Uiso 1 1 calc R . . . .
C126 C 0.4385(4) 0.1296(3) 0.24859(15) 0.0274(11) Uani 1 1 d . U . . .
H126 H 0.4935 0.1259 0.2378 0.033 Uiso 1 1 calc R . . . .
C127 C 0.3541(4) 0.0612(3) 0.24521(14) 0.0219(10) Uani 1 1 d . U . . .
C128 C 0.2718(3) 0.0704(3) 0.26114(14) 0.0207(10) Uani 1 1 d . U . . .
C129 C 0.7934(5) 0.5982(3) 0.02783(19) 0.0437(17) Uani 1 1 d . U . . .
C130 C 0.8174(6) 0.6774(4) 0.0524(2) 0.059(2) Uani 1 1 d . U . . .
H130 H 0.7765 0.7032 0.0504 0.071 Uiso 1 1 calc R . . . .
C131 C 0.9010(7) 0.7164(4) 0.0793(2) 0.067(2) Uani 1 1 d . U . . .
H131 H 0.9161 0.7689 0.0954 0.081 Uiso 1 1 calc R . . . .
C132 C 0.9645(6) 0.6805(4) 0.0833(2) 0.064(2) Uani 1 1 d . U . . .
H132 H 1.0210 0.7088 0.1019 0.077 Uiso 1 1 calc R . . . .
C133 C 0.9431(5) 0.6010(4) 0.05915(19) 0.0476(17) Uani 1 1 d . U . . .
H133 H 0.9850 0.5763 0.0615 0.057 Uiso 1 1 calc R . . . .
C134 C 0.8597(4) 0.5612(3) 0.03220(17) 0.0344(14) Uani 1 1 d . U . . .
C135 C 0.8165(4) 0.4794(3) 0.00247(16) 0.0254(12) Uani 1 1 d . U . . .
C136 C 0.8424(4) 0.4150(3) -0.00811(16) 0.0255(11) Uani 1 1 d . U . . .
H136 H 0.8993 0.4180 0.0049 0.031 Uiso 1 1 calc R . . . .
C137 C 0.7826(4) 0.3447(3) -0.03861(16) 0.0291(12) Uani 1 1 d . U . . .
H137 H 0.8014 0.3018 -0.0459 0.035 Uiso 1 1 calc R . . . .
C138 C 0.6968(4) 0.3369(3) -0.05819(17) 0.0294(12) Uani 1 1 d . U . . .
H138 H 0.6591 0.2895 -0.0784 0.035 Uiso 1 1 calc R . . . .
C139 C 0.6663(4) 0.4014(3) -0.04736(17) 0.0303(13) Uani 1 1 d . U . . .
C140 C 0.5800(4) 0.4042(4) -0.0635(2) 0.0438(16) Uani 1 1 d . U . . .
H140 H 0.5353 0.3599 -0.0835 0.053 Uiso 1 1 calc R . . . .
C141 C 0.5638(5) 0.4731(5) -0.0491(2) 0.055(2) Uani 1 1 d . U . . .
H141 H 0.5073 0.4739 -0.0599 0.067 Uiso 1 1 calc R . . . .
C142 C 0.6272(5) 0.5418(4) -0.0192(2) 0.0517(19) Uani 1 1 d . U . . .
H142 H 0.6127 0.5868 -0.0103 0.062 Uiso 1 1 calc R . . . .
C143 C 0.7123(5) 0.5419(4) -0.00293(19) 0.0406(16) Uani 1 1 d . U . . .
C144 C 0.7288(4) 0.4710(3) -0.01753(17) 0.0300(13) Uani 1 1 d . U . . .
C145 C 0.7043(3) 0.8901(3) 0.98925(13) 0.0191(10) Uani 1 1 d . U . . .
C146 C 0.6816(4) 0.8068(3) 0.98307(14) 0.0240(11) Uani 1 1 d . U . . .
H146 H 0.7265 0.7866 0.9736 0.029 Uiso 1 1 calc R . . . .
C147 C 0.5898(4) 0.7541(3) 0.99146(16) 0.0309(12) Uani 1 1 d . U . . .
H147 H 0.5734 0.6978 0.9875 0.037 Uiso 1 1 calc R . . . .
C148 C 0.5218(4) 0.7830(3) 1.00565(15) 0.0270(11) Uani 1 1 d . U . . .
H148 H 0.4606 0.7461 1.0107 0.032 Uiso 1 1 calc R . . . .
C149 C 0.5451(3) 0.8673(3) 1.01241(14) 0.0237(11) Uani 1 1 d . U . . .
H149 H 0.5002 0.8872 1.0223 0.028 Uiso 1 1 calc R . . . .
C150 C 0.6357(3) 0.9205(3) 1.00418(13) 0.0179(10) Uani 1 1 d . U . . .
C151 C 0.6813(3) 1.0117(3) 1.00833(13) 0.0165(9) Uani 1 1 d . U . . .
C152 C 0.6513(4) 1.0731(3) 1.01959(14) 0.0226(10) Uani 1 1 d . U . . .
H152 H 0.5891 1.0613 1.0278 0.027 Uiso 1 1 calc R . . . .
C153 C 0.7173(4) 1.1555(3) 1.01838(15) 0.0264(11) Uani 1 1 d . U . . .
H153 H 0.6974 1.1976 1.0262 0.032 Uiso 1 1 calc R . . . .
C154 C 0.8088(4) 1.1750(3) 1.00621(14) 0.0284(12) Uani 1 1 d . U . . .
H154 H 0.8500 1.2298 1.0062 0.034 Uiso 1 1 calc R . . . .
C155 C 0.8420(4) 1.1121(3) 0.99350(14) 0.0236(11) Uani 1 1 d . U . . .
C156 C 0.9330(4) 1.1203(3) 0.97808(14) 0.0279(12) Uani 1 1 d . U . . .
H156 H 0.9803 1.1721 0.9760 0.033 Uiso 1 1 calc R . . . .
C157 C 0.9500(4) 1.0520(3) 0.96647(15) 0.0270(11) Uani 1 1 d . U . . .
H157 H 1.0098 1.0589 0.9566 0.032 Uiso 1 1 calc R . . . .
C158 C 0.8818(3) 0.9710(3) 0.96850(14) 0.0235(11) Uani 1 1 d . U . . .
H158 H 0.8964 0.9259 0.9601 0.028 Uiso 1 1 calc R . . . .
C159 C 0.7937(3) 0.9608(3) 0.98323(13) 0.0188(10) Uani 1 1 d . U . . .
C160 C 0.7756(3) 1.0317(3) 0.99513(13) 0.0176(9) Uani 1 1 d . U . . .
C161 C 0.2097(3) 0.3953(3) 0.24416(14) 0.0202(10) Uani 1 1 d . U . . .
C162 C 0.1887(4) 0.3116(3) 0.23499(15) 0.0256(11) Uani 1 1 d . U . . .
H162 H 0.2350 0.2930 0.2411 0.031 Uiso 1 1 calc R . . . .
C163 C 0.0963(4) 0.2560(3) 0.21646(15) 0.0276(12) Uani 1 1 d . U . . .
H163 H 0.0814 0.1999 0.2105 0.033 Uiso 1 1 calc R . . . .
C164 C 0.0267(4) 0.2825(3) 0.20680(15) 0.0298(12) Uani 1 1 d . U . . .
H164 H -0.0339 0.2444 0.1942 0.036 Uiso 1 1 calc R . . . .
C165 C 0.0473(4) 0.3662(3) 0.21595(14) 0.0241(11) Uani 1 1 d . U . . .
H165 H 0.0008 0.3843 0.2095 0.029 Uiso 1 1 calc R . . . .
C166 C 0.1381(4) 0.4223(3) 0.23483(14) 0.0224(11) Uani 1 1 d . U . . .
C167 C 0.1808(4) 0.5132(3) 0.24841(14) 0.0233(11) Uani 1 1 d . U . . .
C168 C 0.1482(4) 0.5742(3) 0.24911(14) 0.0250(11) Uani 1 1 d . U . . .
H168 H 0.0854 0.5614 0.2387 0.030 Uiso 1 1 calc R . . . .
C169 C 0.2130(4) 0.6562(3) 0.26603(15) 0.0260(11) Uani 1 1 d . U . . .
H169 H 0.1911 0.6973 0.2667 0.031 Uiso 1 1 calc R . . . .
C170 C 0.3063(4) 0.6789(3) 0.28149(15) 0.0272(12) Uani 1 1 d . U . . .
H170 H 0.3463 0.7342 0.2920 0.033 Uiso 1 1 calc R . . . .
C171 C 0.3420(4) 0.6178(3) 0.28136(14) 0.0244(11) Uani 1 1 d . U . . .
C172 C 0.4345(4) 0.6286(3) 0.29750(15) 0.0263(11) Uani 1 1 d . U . . .
H172 H 0.4811 0.6813 0.3089 0.032 Uiso 1 1 calc R . . . .
C173 C 0.4554(4) 0.5610(3) 0.29631(15) 0.0269(11) Uani 1 1 d . U . . .
H173 H 0.5163 0.5696 0.3073 0.032 Uiso 1 1 calc R . . . .
C174 C 0.3885(4) 0.4796(3) 0.27912(15) 0.0256(11) Uani 1 1 d . U . . .
H174 H 0.4049 0.4354 0.2786 0.031 Uiso 1 1 calc R . . . .
C175 C 0.2991(4) 0.4676(3) 0.26336(14) 0.0211(10) Uani 1 1 d . U . . .
C176 C 0.2772(3) 0.5362(3) 0.26482(14) 0.0196(10) Uani 1 1 d . U . . .
F1 F 0.8439(2) 0.93314(18) 0.32756(9) 0.0320(7) Uani 1 1 d . . . . .
F2 F 0.6664(2) 0.80981(16) 0.31686(9) 0.0327(7) Uani 1 1 d . . . . .
F3 F 0.5152(2) 0.83652(16) 0.34980(9) 0.0314(7) Uani 1 1 d . . . . .
F4 F 0.54319(19) 0.98344(17) 0.39716(9) 0.0290(7) Uani 1 1 d . . . . .
F5 F 0.5035(2) 0.10338(19) 0.35233(9) 0.0377(8) Uani 1 1 d . . . . .
F6 F 0.4101(2) -0.05730(19) 0.31841(9) 0.0411(8) Uani 1 1 d . . . . .
F7 F 0.2196(2) -0.13819(18) 0.32655(9) 0.0435(8) Uani 1 1 d . . . . .
F8 F 0.1216(2) -0.05885(18) 0.36989(9) 0.0371(8) Uani 1 1 d . . . . .
F9 F 0.0355(2) 0.44186(18) 0.08328(9) 0.0342(7) Uani 1 1 d . . . . .
F10 F 0.1284(2) 0.59602(17) 0.12883(9) 0.0344(7) Uani 1 1 d . . . . .
F11 F 0.3066(2) 0.64705(16) 0.16965(9) 0.0337(7) Uani 1 1 d . . . . .
F12 F 0.3891(2) 0.54205(17) 0.16834(8) 0.0298(7) Uani 1 1 d . . . . .
F13 F 0.0410(2) 0.48562(18) 0.34094(8) 0.0316(7) Uani 1 1 d . . . . .
F14 F 0.1646(2) 0.64374(17) 0.36505(9) 0.0304(7) Uani 1 1 d . . . . .
F15 F 0.3500(2) 0.68367(16) 0.39272(8) 0.0301(7) Uani 1 1 d . . . . .
F16 F 0.40763(19) 0.56531(16) 0.40255(8) 0.0261(6) Uani 1 1 d . . . . .
F17 F 0.6908(3) 0.5809(2) 0.13124(11) 0.0656(13) Uani 1 1 d . . . . .
F18 F 0.8567(3) 0.6851(2) 0.17921(11) 0.0702(14) Uani 1 1 d . . . . .
F19 F 0.9939(2) 0.63444(18) 0.19632(9) 0.0487(9) Uani 1 1 d . . . . .
F20 F 0.9648(2) 0.47819(18) 0.16861(9) 0.0312(7) Uani 1 1 d . . . . .
F21 F 0.7160(2) 0.63502(17) 0.37452(9) 0.0296(7) Uani 1 1 d . . . . .
F22 F 0.9005(2) 0.72468(16) 0.40665(9) 0.0310(7) Uani 1 1 d . . . . .
F23 F 1.0133(2) 0.64950(18) 0.42527(9) 0.0320(7) Uani 1 1 d . . . . .
F24 F 0.9406(2) 0.48516(17) 0.41577(9) 0.0304(7) Uani 1 1 d . . . . .
F25 F 0.5392(2) 0.95511(19) 0.14726(9) 0.0343(7) Uani 1 1 d . . . . .
F26 F 0.5115(2) 0.79912(18) 0.11941(9) 0.0344(7) Uani 1 1 d . . . . .
F27 F 0.6599(2) 0.76363(16) 0.08996(9) 0.0306(7) Uani 1 1 d . . . . .
F28 F 0.8320(2) 0.88540(17) 0.08355(8) 0.0288(7) Uani 1 1 d . . . . .
F29 F 0.4772(2) 1.02634(18) 0.08723(9) 0.0319(7) Uani 1 1 d . . . . .
F30 F 0.3599(2) 0.86674(17) 0.08141(8) 0.0306(7) Uani 1 1 d . . . . .
F31 F 0.1753(2) 0.82083(16) 0.10313(9) 0.0315(7) Uani 1 1 d . . . . .
F32 F 0.1124(2) 0.93479(17) 0.13656(8) 0.0306(7) Uani 1 1 d . . . . .
I1 I 0.72420(3) 1.15012(2) 0.42473(2) 0.02859(8) Uani 1 1 d . . . . .
I2 I 0.92798(2) 1.11538(2) 0.37768(2) 0.02981(8) Uani 1 1 d . . . . .
I3 I 0.18401(3) 0.12310(2) 0.42006(2) 0.03448(9) Uani 1 1 d . . . . .
I4 I 0.44185(3) 0.23213(2) 0.40683(2) 0.03719(9) Uani 1 1 d . . . . .
I5 I 0.32406(3) 0.35594(2) 0.12562(2) 0.02868(8) Uani 1 1 d . . . . .
I6 I 0.08212(3) 0.28776(2) 0.06892(2) 0.03161(8) Uani 1 1 d . . . . .
I7 I 0.30352(2) 0.37233(2) 0.38471(2) 0.02655(8) Uani 1 1 d . . . . .
I8 I 0.05246(2) 0.31922(2) 0.34484(2) 0.03080(8) Uani 1 1 d . . . . .
I9 I 0.79836(3) 0.32619(2) 0.11189(2) 0.03552(9) Uani 1 1 d . . . . .
I10 I 0.61233(3) 0.39516(3) 0.08531(2) 0.05390(13) Uani 1 1 d . . . . .
I11 I 0.74154(3) 0.34398(2) 0.37940(2) 0.03320(9) Uani 1 1 d . . . . .
I12 I 0.58524(3) 0.44574(2) 0.35474(2) 0.03431(9) Uani 1 1 d . . . . .
I13 I 0.71471(3) 1.12475(2) 0.15081(2) 0.03235(8) Uani 1 1 d . . . . .
I14 I 0.91506(2) 1.07771(2) 0.10904(2) 0.03080(8) Uani 1 1 d . . . . .
I15 I 0.20794(3) 1.12751(2) 0.15504(2) 0.03133(8) Uani 1 1 d . . . . .
I16 I 0.45803(3) 1.18916(2) 0.12252(2) 0.03086(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.406(6) . ?
C1 C6 1.374(6) . ?
C1 I1 2.086(4) . ?
C2 C3 1.379(6) . ?
C2 I2 2.078(4) . ?
C3 C4 1.367(6) . ?
C3 F1 1.352(5) . ?
C4 C5 1.381(6) . ?
C4 F2 1.334(5) . ?
C5 C6 1.384(7) . ?
C5 F3 1.338(5) . ?
C6 F4 1.346(5) . ?
C7 C8 1.398(6) . ?
C7 C12 1.387(6) . ?
C7 I3 2.079(4) . ?
C8 C9 1.383(7) . ?
C8 I4 2.081(5) . ?
C9 C10 1.368(7) . ?
C9 F5 1.351(5) . ?
C10 C11 1.372(7) . ?
C10 F6 1.340(5) . ?
C11 C12 1.383(7) . ?
C11 F7 1.333(6) . ?
C12 F8 1.340(5) . ?
C13 C14 1.398(7) . ?
C13 C18 1.378(6) . ?
C13 I5 2.085(5) . ?
C14 C15 1.382(6) . ?
C14 I6 2.084(5) . ?
C15 C16 1.381(7) . ?
C15 F9 1.352(6) . ?
C16 C17 1.366(7) . ?
C16 F10 1.341(5) . ?
C17 C18 1.379(7) . ?
C17 F11 1.344(5) . ?
C18 F12 1.351(5) . ?
C19 C20 1.395(7) . ?
C19 C24 1.377(6) . ?
C19 I7 2.097(5) . ?
C20 C21 1.371(7) . ?
C20 I8 2.088(5) . ?
C21 C22 1.376(7) . ?
C21 F13 1.343(5) . ?
C22 C23 1.366(7) . ?
C22 F14 1.346(5) . ?
C23 C24 1.385(6) . ?
C23 F15 1.339(5) . ?
C24 F16 1.346(5) . ?
C25 C26 1.400(6) . ?
C25 C30 1.392(7) . ?
C25 I9 2.073(4) . ?
C26 C27 1.387(7) . ?
C26 I10 2.086(6) . ?
C27 C28 1.372(9) . ?
C27 F17 1.346(6) . ?
C28 C29 1.365(8) . ?
C28 F18 1.325(6) . ?
C29 C30 1.370(6) . ?
C29 F19 1.341(6) . ?
C30 F20 1.340(5) . ?
C31 C32 1.387(6) . ?
C31 C36 1.383(7) . ?
C31 I11 2.084(4) . ?
C32 C33 1.377(6) . ?
C32 I12 2.083(5) . ?
C33 C34 1.369(7) . ?
C33 F21 1.349(5) . ?
C34 C35 1.383(7) . ?
C34 F22 1.345(5) . ?
C35 C36 1.380(7) . ?
C35 F23 1.336(6) . ?
C36 F24 1.353(5) . ?
C37 C38 1.415(6) . ?
C37 C42 1.378(6) . ?
C37 I13 2.078(4) . ?
C38 C39 1.376(6) . ?
C38 I14 2.087(4) . ?
C39 C40 1.385(6) . ?
C39 F28 1.345(5) . ?
C40 C41 1.375(6) . ?
C40 F27 1.335(5) . ?
C41 C42 1.366(7) . ?
C41 F26 1.344(5) . ?
C42 F25 1.345(5) . ?
C43 C44 1.392(6) . ?
C43 C48 1.374(6) . ?
C43 I15 2.088(4) . ?
C44 C45 1.396(6) . ?
C44 I16 2.085(5) . ?
C45 C46 1.358(6) . ?
C45 F29 1.356(5) . ?
C46 C47 1.377(6) . ?
C46 F30 1.335(5) . ?
C47 C48 1.377(6) . ?
C47 F31 1.339(5) . ?
C48 F32 1.351(5) . ?
C49 C50 1.389(7) . ?
C49 C54 1.424(7) . ?
C49 C63 1.468(7) . ?
C50 H50 0.9300 . ?
C50 C51 1.385(8) . ?
C51 H51 0.9300 . ?
C51 C52 1.365(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.403(7) . ?
C53 H53 0.9300 . ?
C53 C54 1.386(7) . ?
C54 C55 1.469(7) . ?
C55 C56 1.370(6) . ?
C55 C64 1.421(7) . ?
C56 H56 0.9300 . ?
C56 C57 1.415(7) . ?
C57 H57 0.9300 . ?
C57 C58 1.365(8) . ?
C58 H58 0.9300 . ?
C58 C59 1.422(7) . ?
C59 C60 1.418(7) . ?
C59 C64 1.397(7) . ?
C60 H60 0.9300 . ?
C60 C61 1.363(8) . ?
C61 H61 0.9300 . ?
C61 C62 1.414(8) . ?
C62 H62 0.9300 . ?
C62 C63 1.372(7) . ?
C63 C64 1.409(6) . ?
C65 C66 1.377(6) . ?
C65 C70 1.406(6) . ?
C65 C79 1.487(6) . ?
C66 H66 0.9300 . ?
C66 C67 1.387(7) . ?
C67 H67 0.9300 . ?
C67 C68 1.375(7) . ?
C68 H68 0.9300 . ?
C68 C69 1.386(7) . ?
C69 H69 0.9300 . ?
C69 C70 1.387(6) . ?
C70 C71 1.480(6) . ?
C71 C72 1.378(6) . ?
C71 C80 1.411(6) . ?
C72 H72 0.9300 . ?
C72 C73 1.420(7) . ?
C73 H73 0.9300 . ?
C73 C74 1.366(7) . ?
C74 H74 0.9300 . ?
C74 C75 1.415(7) . ?
C75 C76 1.416(7) . ?
C75 C80 1.397(6) . ?
C76 H76 0.9300 . ?
C76 C77 1.375(7) . ?
C77 H77 0.9300 . ?
C77 C78 1.425(6) . ?
C78 H78 0.9300 . ?
C78 C79 1.374(6) . ?
C79 C80 1.407(6) . ?
C81 C82 1.384(6) . ?
C81 C86 1.424(6) . ?
C81 C95 1.470(6) . ?
C82 H82 0.9300 . ?
C82 C83 1.382(7) . ?
C83 H83 0.9300 . ?
C83 C84 1.375(7) . ?
C84 H84 0.9300 . ?
C84 C85 1.390(7) . ?
C85 H85 0.9300 . ?
C85 C86 1.381(7) . ?
C86 C87 1.467(7) . ?
C87 C88 1.375(7) . ?
C87 C96 1.411(8) . ?
C88 H88 0.9300 . ?
C88 C89 1.399(10) . ?
C89 H89 0.9300 . ?
C89 C90 1.330(11) . ?
C90 H90 0.9300 . ?
C90 C91 1.455(10) . ?
C91 C92 1.396(10) . ?
C91 C96 1.415(8) . ?
C92 H92 0.9300 . ?
C92 C93 1.367(10) . ?
C93 H93 0.9300 . ?
C93 C94 1.434(8) . ?
C94 H94 0.9300 . ?
C94 C95 1.371(7) . ?
C95 C96 1.416(7) . ?
C97 C98 1.394(7) . ?
C97 C102 1.418(7) . ?
C97 C111 1.468(7) . ?
C98 H98 0.9300 . ?
C98 C99 1.387(9) . ?
C99 H99 0.9300 . ?
C99 C100 1.381(9) . ?
C100 H100 0.9300 . ?
C100 C101 1.385(8) . ?
C101 H101 0.9300 . ?
C101 C102 1.393(8) . ?
C102 C103 1.454(7) . ?
C103 C104 1.403(7) . ?
C103 C112 1.394(7) . ?
C104 H104 0.9300 . ?
C104 C105 1.403(8) . ?
C105 H105 0.9300 . ?
C105 C106 1.372(8) . ?
C106 H106 0.9300 . ?
C106 C107 1.416(7) . ?
C107 C108 1.419(7) . ?
C107 C112 1.394(7) . ?
C108 H108 0.9300 . ?
C108 C109 1.379(7) . ?
C109 H109 0.9300 . ?
C109 C110 1.413(8) . ?
C110 H110 0.9300 . ?
C110 C111 1.371(7) . ?
C111 C112 1.420(7) . ?
C113 C114 1.389(6) . ?
C113 C118 1.417(7) . ?
C113 C127 1.480(7) . ?
C114 H114 0.9300 . ?
C114 C115 1.382(7) . ?
C115 H115 0.9300 . ?
C115 C116 1.392(7) . ?
C116 H116 0.9300 . ?
C116 C117 1.392(7) . ?
C117 H117 0.9300 . ?
C117 C118 1.393(7) . ?
C118 C119 1.469(6) . ?
C119 C120 1.369(6) . ?
C119 C128 1.416(7) . ?
C120 H120 0.9300 . ?
C120 C121 1.425(7) . ?
C121 H121 0.9300 . ?
C121 C122 1.367(7) . ?
C122 H122 0.9300 . ?
C122 C123 1.432(7) . ?
C123 C124 1.415(7) . ?
C123 C128 1.394(6) . ?
C124 H124 0.9300 . ?
C124 C125 1.363(7) . ?
C125 H125 0.9300 . ?
C125 C126 1.429(7) . ?
C126 H126 0.9300 . ?
C126 C127 1.360(7) . ?
C127 C128 1.416(6) . ?
C129 C130 1.402(8) . ?
C129 C134 1.443(8) . ?
C129 C143 1.444(9) . ?
C130 H130 0.9300 . ?
C130 C131 1.363(11) . ?
C131 H131 0.9300 . ?
C131 C132 1.388(10) . ?
C132 H132 0.9300 . ?
C132 C133 1.409(8) . ?
C133 H133 0.9300 . ?
C133 C134 1.363(8) . ?
C134 C135 1.484(7) . ?
C135 C136 1.372(6) . ?
C135 C144 1.408(8) . ?
C136 H136 0.9300 . ?
C136 C137 1.402(7) . ?
C137 H137 0.9300 . ?
C137 C138 1.381(7) . ?
C138 H138 0.9300 . ?
C138 C139 1.421(7) . ?
C139 C140 1.427(8) . ?
C139 C144 1.397(8) . ?
C140 H140 0.9300 . ?
C140 C141 1.376(8) . ?
C141 H141 0.9300 . ?
C141 C142 1.394(9) . ?
C142 H142 0.9300 . ?
C142 C143 1.388(9) . ?
C143 C144 1.413(7) . ?
C145 C146 1.380(6) . ?
C145 C150 1.418(6) . ?
C145 C159 1.474(6) . ?
C146 H146 0.9300 . ?
C146 C147 1.387(7) . ?
C147 H147 0.9300 . ?
C147 C148 1.388(7) . ?
C148 H148 0.9300 . ?
C148 C149 1.395(7) . ?
C149 H149 0.9300 . ?
C149 C150 1.374(6) . ?
C150 C151 1.487(6) . ?
C151 C152 1.366(6) . ?
C151 C160 1.413(6) . ?
C152 H152 0.9300 . ?
C152 C153 1.420(6) . ?
C153 H153 0.9300 . ?
C153 C154 1.365(7) . ?
C154 H154 0.9300 . ?
C154 C155 1.428(7) . ?
C155 C156 1.429(7) . ?
C155 C160 1.398(6) . ?
C156 H156 0.9300 . ?
C156 C157 1.359(7) . ?
C157 H157 0.9300 . ?
C157 C158 1.417(7) . ?
C158 H158 0.9300 . ?
C158 C159 1.372(6) . ?
C159 C160 1.415(6) . ?
C161 C162 1.393(6) . ?
C161 C166 1.415(7) . ?
C161 C175 1.479(7) . ?
C162 H162 0.9300 . ?
C162 C163 1.399(7) . ?
C163 H163 0.9300 . ?
C163 C164 1.384(7) . ?
C164 H164 0.9300 . ?
C164 C165 1.393(7) . ?
C165 H165 0.9300 . ?
C165 C166 1.387(7) . ?
C166 C167 1.481(6) . ?
C167 C168 1.385(6) . ?
C167 C176 1.418(7) . ?
C168 H168 0.9300 . ?
C168 C169 1.408(7) . ?
C169 H169 0.9300 . ?
C169 C170 1.368(7) . ?
C170 H170 0.9300 . ?
C170 C171 1.421(7) . ?
C171 C172 1.419(7) . ?
C171 C176 1.400(6) . ?
C172 H172 0.9300 . ?
C172 C173 1.382(7) . ?
C173 H173 0.9300 . ?
C173 C174 1.411(7) . ?
C174 H174 0.9300 . ?
C174 C175 1.364(7) . ?
C175 C176 1.408(6) . ?

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 123.6(3) . . ?
C6 C1 C2 118.5(4) . . ?
C6 C1 I1 117.9(3) . . ?
C1 C2 I2 122.7(3) . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 I2 118.2(3) . . ?
C4 C3 C2 122.0(4) . . ?
F1 C3 C2 120.3(4) . . ?
F1 C3 C4 117.7(4) . . ?
C3 C4 C5 119.2(4) . . ?
F2 C4 C3 121.0(4) . . ?
F2 C4 C5 119.7(4) . . ?
C4 C5 C6 119.6(4) . . ?
F3 C5 C4 120.3(4) . . ?
F3 C5 C6 120.1(4) . . ?
C1 C6 C5 121.7(4) . . ?
F4 C6 C1 120.9(4) . . ?
F4 C6 C5 117.4(4) . . ?
C8 C7 I3 122.9(3) . . ?
C12 C7 C8 118.6(4) . . ?
C12 C7 I3 118.5(3) . . ?
C7 C8 I4 123.2(4) . . ?
C9 C8 C7 119.0(5) . . ?
C9 C8 I4 117.7(4) . . ?
C10 C9 C8 121.9(5) . . ?
F5 C9 C8 120.4(5) . . ?
F5 C9 C10 117.7(4) . . ?
C9 C10 C11 119.4(4) . . ?
F6 C10 C9 120.3(5) . . ?
F6 C10 C11 120.2(5) . . ?
C10 C11 C12 119.9(5) . . ?
F7 C11 C10 119.4(5) . . ?
F7 C11 C12 120.7(5) . . ?
C11 C12 C7 121.2(5) . . ?
F8 C12 C7 120.8(4) . . ?
F8 C12 C11 118.0(5) . . ?
C14 C13 I5 123.2(3) . . ?
C18 C13 C14 118.8(4) . . ?
C18 C13 I5 118.0(4) . . ?
C13 C14 I6 123.6(3) . . ?
C15 C14 C13 118.8(4) . . ?
C15 C14 I6 117.6(4) . . ?
C16 C15 C14 121.6(5) . . ?
F9 C15 C14 121.0(4) . . ?
F9 C15 C16 117.5(4) . . ?
C17 C16 C15 119.5(4) . . ?
F10 C16 C15 120.2(5) . . ?
F10 C16 C17 120.3(5) . . ?
C16 C17 C18 119.6(5) . . ?
F11 C17 C16 119.7(4) . . ?
F11 C17 C18 120.8(5) . . ?
C17 C18 C13 121.8(5) . . ?
F12 C18 C13 121.3(4) . . ?
F12 C18 C17 116.9(4) . . ?
C20 C19 I7 123.0(3) . . ?
C24 C19 C20 119.1(4) . . ?
C24 C19 I7 117.8(4) . . ?
C19 C20 I8 123.6(3) . . ?
C21 C20 C19 119.0(4) . . ?
C21 C20 I8 117.3(4) . . ?
C20 C21 C22 121.7(5) . . ?
F13 C21 C20 121.3(4) . . ?
F13 C21 C22 117.0(4) . . ?
C23 C22 C21 119.6(4) . . ?
F14 C22 C21 120.6(4) . . ?
F14 C22 C23 119.9(4) . . ?
C22 C23 C24 119.6(4) . . ?
F15 C23 C22 120.3(4) . . ?
F15 C23 C24 120.1(4) . . ?
C19 C24 C23 121.0(5) . . ?
F16 C24 C19 121.1(4) . . ?
F16 C24 C23 117.9(4) . . ?
C26 C25 I9 124.2(4) . . ?
C30 C25 C26 118.5(4) . . ?
C30 C25 I9 117.3(3) . . ?
C25 C26 I10 122.3(4) . . ?
C27 C26 C25 119.0(5) . . ?
C27 C26 I10 118.7(4) . . ?
C28 C27 C26 121.2(5) . . ?
F17 C27 C26 120.1(6) . . ?
F17 C27 C28 118.7(5) . . ?
C29 C28 C27 119.8(5) . . ?
F18 C28 C27 120.5(6) . . ?
F18 C28 C29 119.6(6) . . ?
C28 C29 C30 120.2(5) . . ?
F19 C29 C28 120.0(5) . . ?
F19 C29 C30 119.8(5) . . ?
C29 C30 C25 121.2(5) . . ?
F20 C30 C25 120.9(4) . . ?
F20 C30 C29 117.9(5) . . ?
C32 C31 I11 124.9(4) . . ?
C36 C31 C32 118.9(4) . . ?
C36 C31 I11 116.1(3) . . ?
C31 C32 I12 122.7(3) . . ?
C33 C32 C31 119.3(5) . . ?
C33 C32 I12 118.0(4) . . ?
C34 C33 C32 121.4(4) . . ?
F21 C33 C32 120.9(5) . . ?
F21 C33 C34 117.7(4) . . ?
C33 C34 C35 120.0(4) . . ?
F22 C34 C33 120.9(4) . . ?
F22 C34 C35 119.0(4) . . ?
C36 C35 C34 118.6(5) . . ?
F23 C35 C34 120.1(4) . . ?
F23 C35 C36 121.3(5) . . ?
C35 C36 C31 121.7(5) . . ?
F24 C36 C31 122.0(4) . . ?
F24 C36 C35 116.3(5) . . ?
C38 C37 I13 123.7(3) . . ?
C42 C37 C38 118.1(4) . . ?
C42 C37 I13 118.2(3) . . ?
C37 C38 I14 122.5(3) . . ?
C39 C38 C37 119.2(4) . . ?
C39 C38 I14 118.3(3) . . ?
C38 C39 C40 121.4(4) . . ?
F28 C39 C38 120.8(4) . . ?
F28 C39 C40 117.9(4) . . ?
C41 C40 C39 119.1(4) . . ?
F27 C40 C39 119.8(4) . . ?
F27 C40 C41 121.0(4) . . ?
C42 C41 C40 120.2(4) . . ?
F26 C41 C40 119.5(4) . . ?
F26 C41 C42 120.3(4) . . ?
C41 C42 C37 122.0(4) . . ?
F25 C42 C37 120.5(4) . . ?
F25 C42 C41 117.5(4) . . ?
C44 C43 I15 122.8(3) . . ?
C48 C43 C44 119.3(4) . . ?
C48 C43 I15 117.9(3) . . ?
C43 C44 C45 118.0(4) . . ?
C43 C44 I16 124.6(3) . . ?
C45 C44 I16 117.5(3) . . ?
C46 C45 C44 122.5(4) . . ?
F29 C45 C44 119.7(4) . . ?
F29 C45 C46 117.8(4) . . ?
C45 C46 C47 118.9(4) . . ?
F30 C46 C45 120.7(4) . . ?
F30 C46 C47 120.4(4) . . ?
C46 C47 C48 119.8(4) . . ?
F31 C47 C46 119.5(4) . . ?
F31 C47 C48 120.7(4) . . ?
C43 C48 C47 121.5(4) . . ?
F32 C48 C43 121.0(4) . . ?
F32 C48 C47 117.5(4) . . ?
C50 C49 C54 120.0(5) . . ?
C50 C49 C63 131.9(5) . . ?
C54 C49 C63 108.1(4) . . ?
C49 C50 H50 120.5 . . ?
C51 C50 C49 119.0(5) . . ?
C51 C50 H50 120.5 . . ?
C50 C51 H51 119.3 . . ?
C52 C51 C50 121.4(5) . . ?
C52 C51 H51 119.3 . . ?
C51 C52 H52 119.5 . . ?
C51 C52 C53 121.0(6) . . ?
C53 C52 H52 119.5 . . ?
C52 C53 H53 120.7 . . ?
C54 C53 C52 118.7(5) . . ?
C54 C53 H53 120.7 . . ?
C49 C54 C55 108.1(4) . . ?
C53 C54 C49 119.9(5) . . ?
C53 C54 C55 132.0(5) . . ?
C56 C55 C54 136.2(5) . . ?
C56 C55 C64 117.7(5) . . ?
C64 C55 C54 106.1(4) . . ?
C55 C56 H56 120.5 . . ?
C55 C56 C57 119.0(5) . . ?
C57 C56 H56 120.5 . . ?
C56 C57 H57 118.7 . . ?
C58 C57 C56 122.7(5) . . ?
C58 C57 H57 118.7 . . ?
C57 C58 H58 119.7 . . ?
C57 C58 C59 120.6(5) . . ?
C59 C58 H58 119.7 . . ?
C60 C59 C58 128.6(5) . . ?
C64 C59 C58 115.3(5) . . ?
C64 C59 C60 116.1(5) . . ?
C59 C60 H60 119.9 . . ?
C61 C60 C59 120.1(5) . . ?
C61 C60 H60 119.9 . . ?
C60 C61 H61 118.6 . . ?
C60 C61 C62 122.9(5) . . ?
C62 C61 H61 118.6 . . ?
C61 C62 H62 120.7 . . ?
C63 C62 C61 118.6(5) . . ?
C63 C62 H62 120.7 . . ?
C62 C63 C49 135.3(5) . . ?
C62 C63 C64 118.3(5) . . ?
C64 C63 C49 106.4(4) . . ?
C59 C64 C55 124.6(4) . . ?
C59 C64 C63 124.1(5) . . ?
C63 C64 C55 111.3(4) . . ?
C66 C65 C70 120.7(4) . . ?
C66 C65 C79 131.3(5) . . ?
C70 C65 C79 107.9(4) . . ?
C65 C66 H66 120.6 . . ?
C65 C66 C67 118.7(5) . . ?
C67 C66 H66 120.6 . . ?
C66 C67 H67 119.6 . . ?
C68 C67 C66 120.8(5) . . ?
C68 C67 H67 119.6 . . ?
C67 C68 H68 119.5 . . ?
C67 C68 C69 121.1(5) . . ?
C69 C68 H68 119.5 . . ?
C68 C69 H69 120.6 . . ?
C68 C69 C70 118.7(5) . . ?
C70 C69 H69 120.6 . . ?
C65 C70 C71 108.5(4) . . ?
C69 C70 C65 119.8(4) . . ?
C69 C70 C71 131.7(4) . . ?
C72 C71 C70 135.6(4) . . ?
C72 C71 C80 118.5(4) . . ?
C80 C71 C70 105.9(4) . . ?
C71 C72 H72 120.9 . . ?
C71 C72 C73 118.1(5) . . ?
C73 C72 H72 120.9 . . ?
C72 C73 H73 118.7 . . ?
C74 C73 C72 122.7(5) . . ?
C74 C73 H73 118.7 . . ?
C73 C74 H74 119.6 . . ?
C73 C74 C75 120.7(5) . . ?
C75 C74 H74 119.6 . . ?
C76 C75 C74 128.6(5) . . ?
C80 C75 C74 115.6(5) . . ?
C80 C75 C76 115.7(5) . . ?
C75 C76 H76 119.6 . . ?
C77 C76 C75 120.8(4) . . ?
C77 C76 H76 119.6 . . ?
C76 C77 H77 118.8 . . ?
C76 C77 C78 122.5(5) . . ?
C78 C77 H77 118.8 . . ?
C77 C78 H78 121.2 . . ?
C79 C78 C77 117.6(5) . . ?
C79 C78 H78 121.2 . . ?
C78 C79 C65 134.5(4) . . ?
C78 C79 C80 119.5(4) . . ?
C80 C79 C65 106.0(4) . . ?
C75 C80 C71 124.3(5) . . ?
C75 C80 C79 123.9(4) . . ?
C79 C80 C71 111.7(4) . . ?
C82 C81 C86 119.9(4) . . ?
C82 C81 C95 132.1(4) . . ?
C86 C81 C95 108.1(4) . . ?
C81 C82 H82 120.2 . . ?
C83 C82 C81 119.6(5) . . ?
C83 C82 H82 120.2 . . ?
C82 C83 H83 119.8 . . ?
C84 C83 C82 120.5(5) . . ?
C84 C83 H83 119.8 . . ?
C83 C84 H84 119.4 . . ?
C83 C84 C85 121.3(5) . . ?
C85 C84 H84 119.4 . . ?
C84 C85 H85 120.5 . . ?
C86 C85 C84 119.1(5) . . ?
C86 C85 H85 120.5 . . ?
C81 C86 C87 108.5(5) . . ?
C85 C86 C81 119.7(4) . . ?
C85 C86 C87 131.8(5) . . ?
C88 C87 C86 135.2(6) . . ?
C88 C87 C96 119.1(6) . . ?
C96 C87 C86 105.7(4) . . ?
C87 C88 H88 120.9 . . ?
C87 C88 C89 118.2(7) . . ?
C89 C88 H88 120.9 . . ?
C88 C89 H89 118.3 . . ?
C90 C89 C88 123.4(7) . . ?
C90 C89 H89 118.3 . . ?
C89 C90 H90 119.0 . . ?
C89 C90 C91 122.0(7) . . ?
C91 C90 H90 119.0 . . ?
C92 C91 C90 131.7(7) . . ?
C92 C91 C96 115.1(6) . . ?
C96 C91 C90 113.2(7) . . ?
C91 C92 H92 118.8 . . ?
C93 C92 C91 122.4(6) . . ?
C93 C92 H92 118.8 . . ?
C92 C93 H93 119.2 . . ?
C92 C93 C94 121.6(6) . . ?
C94 C93 H93 119.2 . . ?
C93 C94 H94 121.0 . . ?
C95 C94 C93 118.1(6) . . ?
C95 C94 H94 121.0 . . ?
C94 C95 C81 135.4(5) . . ?
C94 C95 C96 119.0(5) . . ?
C96 C95 C81 105.6(4) . . ?
C87 C96 C91 124.1(6) . . ?
C87 C96 C95 112.1(4) . . ?
C91 C96 C95 123.8(6) . . ?
C98 C97 C102 120.7(6) . . ?
C98 C97 C111 132.0(6) . . ?
C102 C97 C111 107.3(4) . . ?
C97 C98 H98 120.7 . . ?
C99 C98 C97 118.5(6) . . ?
C99 C98 H98 120.7 . . ?
C98 C99 H99 119.7 . . ?
C100 C99 C98 120.5(6) . . ?
C100 C99 H99 119.7 . . ?
C99 C100 H100 118.9 . . ?
C99 C100 C101 122.2(6) . . ?
C101 C100 H100 118.9 . . ?
C100 C101 H101 120.9 . . ?
C100 C101 C102 118.3(6) . . ?
C102 C101 H101 120.9 . . ?
C97 C102 C103 108.4(5) . . ?
C101 C102 C97 119.8(5) . . ?
C101 C102 C103 131.8(5) . . ?
C104 C103 C102 135.4(5) . . ?
C112 C103 C102 107.3(4) . . ?
C112 C103 C104 117.3(5) . . ?
C103 C104 H104 121.2 . . ?
C103 C104 C105 117.6(5) . . ?
C105 C104 H104 121.2 . . ?
C104 C105 H105 118.1 . . ?
C106 C105 C104 123.7(5) . . ?
C106 C105 H105 118.1 . . ?
C105 C106 H106 119.8 . . ?
C105 C106 C107 120.3(6) . . ?
C107 C106 H106 119.8 . . ?
C106 C107 C108 128.3(6) . . ?
C112 C107 C106 114.7(5) . . ?
C112 C107 C108 117.0(5) . . ?
C107 C108 H108 120.1 . . ?
C109 C108 C107 119.7(5) . . ?
C109 C108 H108 120.1 . . ?
C108 C109 H109 118.7 . . ?
C108 C109 C110 122.6(5) . . ?
C110 C109 H109 118.7 . . ?
C109 C110 H110 120.7 . . ?
C111 C110 C109 118.7(5) . . ?
C111 C110 H110 120.7 . . ?
C110 C111 C97 134.6(5) . . ?
C110 C111 C112 118.9(5) . . ?
C112 C111 C97 106.5(5) . . ?
C103 C112 C107 126.3(5) . . ?
C103 C112 C111 110.6(5) . . ?
C107 C112 C111 123.1(5) . . ?
C114 C113 C118 120.2(5) . . ?
C114 C113 C127 131.7(5) . . ?
C118 C113 C127 108.1(4) . . ?
C113 C114 H114 120.3 . . ?
C115 C114 C113 119.3(5) . . ?
C115 C114 H114 120.3 . . ?
C114 C115 H115 119.6 . . ?
C114 C115 C116 120.9(5) . . ?
C116 C115 H115 119.6 . . ?
C115 C116 H116 119.7 . . ?
C117 C116 C115 120.6(5) . . ?
C117 C116 H116 119.7 . . ?
C116 C117 H117 120.4 . . ?
C116 C117 C118 119.1(5) . . ?
C118 C117 H117 120.4 . . ?
C113 C118 C119 108.3(4) . . ?
C117 C118 C113 119.9(4) . . ?
C117 C118 C119 131.9(5) . . ?
C120 C119 C118 135.4(5) . . ?
C120 C119 C128 118.1(4) . . ?
C128 C119 C118 106.4(4) . . ?
C119 C120 H120 120.6 . . ?
C119 C120 C121 118.8(5) . . ?
C121 C120 H120 120.6 . . ?
C120 C121 H121 118.8 . . ?
C122 C121 C120 122.3(5) . . ?
C122 C121 H121 118.8 . . ?
C121 C122 H122 119.6 . . ?
C121 C122 C123 120.8(5) . . ?
C123 C122 H122 119.6 . . ?
C124 C123 C122 128.7(5) . . ?
C128 C123 C122 115.1(5) . . ?
C128 C123 C124 116.3(4) . . ?
C123 C124 H124 119.8 . . ?
C125 C124 C123 120.4(5) . . ?
C125 C124 H124 119.8 . . ?
C124 C125 H125 118.9 . . ?
C124 C125 C126 122.2(5) . . ?
C126 C125 H125 118.9 . . ?
C125 C126 H126 120.6 . . ?
C127 C126 C125 118.8(5) . . ?
C127 C126 H126 120.6 . . ?
C126 C127 C113 135.5(4) . . ?
C126 C127 C128 118.4(4) . . ?
C128 C127 C113 106.1(4) . . ?
C119 C128 C127 111.2(4) . . ?
C123 C128 C119 125.0(4) . . ?
C123 C128 C127 123.9(4) . . ?
C130 C129 C134 117.7(7) . . ?
C130 C129 C143 133.0(7) . . ?
C134 C129 C143 109.3(5) . . ?
C129 C130 H130 120.1 . . ?
C131 C130 C129 119.8(7) . . ?
C131 C130 H130 120.1 . . ?
C130 C131 H131 118.9 . . ?
C130 C131 C132 122.2(7) . . ?
C132 C131 H131 118.9 . . ?
C131 C132 H132 120.1 . . ?
C131 C132 C133 119.9(8) . . ?
C133 C132 H132 120.1 . . ?
C132 C133 H133 120.7 . . ?
C134 C133 C132 118.6(7) . . ?
C134 C133 H133 120.7 . . ?
C129 C134 C135 105.7(5) . . ?
C133 C134 C129 121.9(6) . . ?
C133 C134 C135 132.4(6) . . ?
C136 C135 C134 134.8(5) . . ?
C136 C135 C144 117.8(5) . . ?
C144 C135 C134 107.4(4) . . ?
C135 C136 H136 120.2 . . ?
C135 C136 C137 119.6(5) . . ?
C137 C136 H136 120.2 . . ?
C136 C137 H137 118.9 . . ?
C138 C137 C136 122.3(5) . . ?
C138 C137 H137 118.9 . . ?
C137 C138 H138 120.0 . . ?
C137 C138 C139 119.9(5) . . ?
C139 C138 H138 120.0 . . ?
C138 C139 C140 128.1(6) . . ?
C144 C139 C138 116.0(5) . . ?
C144 C139 C140 116.0(5) . . ?
C139 C140 H140 120.4 . . ?
C141 C140 C139 119.2(7) . . ?
C141 C140 H140 120.4 . . ?
C140 C141 H141 118.1 . . ?
C140 C141 C142 123.8(6) . . ?
C142 C141 H141 118.1 . . ?
C141 C142 H142 120.6 . . ?
C143 C142 C141 118.9(5) . . ?
C143 C142 H142 120.6 . . ?
C142 C143 C129 135.8(6) . . ?
C142 C143 C144 117.4(6) . . ?
C144 C143 C129 106.8(5) . . ?
C135 C144 C143 110.8(6) . . ?
C139 C144 C135 124.4(5) . . ?
C139 C144 C143 124.8(6) . . ?
C146 C145 C150 120.7(4) . . ?
C146 C145 C159 131.1(4) . . ?
C150 C145 C159 108.2(4) . . ?
C145 C146 H146 121.0 . . ?
C145 C146 C147 118.0(5) . . ?
C147 C146 H146 121.0 . . ?
C146 C147 H147 119.1 . . ?
C146 C147 C148 121.9(5) . . ?
C148 C147 H147 119.1 . . ?
C147 C148 H148 119.9 . . ?
C147 C148 C149 120.2(4) . . ?
C149 C148 H148 119.9 . . ?
C148 C149 H149 120.6 . . ?
C150 C149 C148 118.8(4) . . ?
C150 C149 H149 120.6 . . ?
C145 C150 C151 108.2(4) . . ?
C149 C150 C145 120.6(4) . . ?
C149 C150 C151 131.2(4) . . ?
C152 C151 C150 135.1(4) . . ?
C152 C151 C160 119.3(4) . . ?
C160 C151 C150 105.5(4) . . ?
C151 C152 H152 120.8 . . ?
C151 C152 C153 118.3(4) . . ?
C153 C152 H152 120.8 . . ?
C152 C153 H153 118.8 . . ?
C154 C153 C152 122.4(4) . . ?
C154 C153 H153 118.8 . . ?
C153 C154 H154 119.6 . . ?
C153 C154 C155 120.7(5) . . ?
C155 C154 H154 119.6 . . ?
C156 C155 C154 128.6(5) . . ?
C160 C155 C154 115.6(4) . . ?
C160 C155 C156 115.8(4) . . ?
C155 C156 H156 120.2 . . ?
C157 C156 C155 119.6(4) . . ?
C157 C156 H156 120.2 . . ?
C156 C157 H157 118.1 . . ?
C156 C157 C158 123.8(4) . . ?
C158 C157 H157 118.1 . . ?
C157 C158 H158 120.9 . . ?
C159 C158 C157 118.2(4) . . ?
C159 C158 H158 120.9 . . ?
C158 C159 C145 135.8(4) . . ?
C158 C159 C160 118.2(4) . . ?
C160 C159 C145 106.0(4) . . ?
C151 C160 C159 112.0(4) . . ?
C155 C160 C151 123.6(4) . . ?
C155 C160 C159 124.4(4) . . ?
C162 C161 C166 119.8(5) . . ?
C162 C161 C175 130.9(5) . . ?
C166 C161 C175 109.2(4) . . ?
C161 C162 H162 120.7 . . ?
C161 C162 C163 118.5(5) . . ?
C163 C162 H162 120.7 . . ?
C162 C163 H163 119.2 . . ?
C164 C163 C162 121.6(5) . . ?
C164 C163 H163 119.2 . . ?
C163 C164 H164 119.9 . . ?
C163 C164 C165 120.1(5) . . ?
C165 C164 H164 119.9 . . ?
C164 C165 H165 120.4 . . ?
C166 C165 C164 119.3(5) . . ?
C166 C165 H165 120.4 . . ?
C161 C166 C167 107.5(4) . . ?
C165 C166 C161 120.7(4) . . ?
C165 C166 C167 131.9(5) . . ?
C168 C167 C166 135.5(5) . . ?
C168 C167 C176 118.6(5) . . ?
C176 C167 C166 105.9(4) . . ?
C167 C168 H168 121.0 . . ?
C167 C168 C169 118.0(5) . . ?
C169 C168 H168 121.0 . . ?
C168 C169 H169 118.2 . . ?
C170 C169 C168 123.7(5) . . ?
C170 C169 H169 118.2 . . ?
C169 C170 H170 120.1 . . ?
C169 C170 C171 119.7(5) . . ?
C171 C170 H170 120.1 . . ?
C172 C171 C170 128.0(5) . . ?
C176 C171 C170 116.5(5) . . ?
C176 C171 C172 115.5(4) . . ?
C171 C172 H172 120.0 . . ?
C173 C172 C171 120.0(5) . . ?
C173 C172 H172 120.0 . . ?
C172 C173 H173 118.5 . . ?
C172 C173 C174 123.0(5) . . ?
C174 C173 H173 118.5 . . ?
C173 C174 H174 121.0 . . ?
C175 C174 C173 118.1(4) . . ?
C175 C174 H174 121.0 . . ?
C174 C175 C161 135.6(4) . . ?
C174 C175 C176 119.2(5) . . ?
C176 C175 C161 105.2(4) . . ?
C171 C176 C167 123.5(4) . . ?
C171 C176 C175 124.3(5) . . ?
C175 C176 C167 112.2(4) . . ?

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 -1.3(6) . . . . ?
C1 C2 C3 F1 -179.7(4) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
C2 C1 C6 F4 179.1(4) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C2 C3 C4 F2 -176.5(4) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C3 C4 C5 F3 179.3(4) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C4 C5 C6 F4 -179.3(4) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C6 C1 C2 I2 -179.3(3) . . . . ?
C7 C8 C9 C10 -1.2(7) . . . . ?
C7 C8 C9 F5 178.9(4) . . . . ?
C8 C7 C12 C11 1.1(7) . . . . ?
C8 C7 C12 F8 -179.7(4) . . . . ?
C8 C9 C10 C11 0.6(7) . . . . ?
C8 C9 C10 F6 -178.0(4) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C9 C10 C11 F7 179.8(4) . . . . ?
C10 C11 C12 C7 -1.7(7) . . . . ?
C10 C11 C12 F8 179.1(4) . . . . ?
C12 C7 C8 C9 0.3(6) . . . . ?
C12 C7 C8 I4 178.8(3) . . . . ?
C13 C14 C15 C16 -2.0(6) . . . . ?
C13 C14 C15 F9 178.1(3) . . . . ?
C14 C13 C18 C17 0.7(6) . . . . ?
C14 C13 C18 F12 -179.0(3) . . . . ?
C14 C15 C16 C17 2.9(6) . . . . ?
C14 C15 C16 F10 -179.2(4) . . . . ?
C15 C16 C17 C18 -2.0(6) . . . . ?
C15 C16 C17 F11 177.4(3) . . . . ?
C16 C17 C18 C13 0.2(6) . . . . ?
C16 C17 C18 F12 179.9(4) . . . . ?
C18 C13 C14 C15 0.2(6) . . . . ?
C18 C13 C14 I6 179.6(3) . . . . ?
C19 C20 C21 C22 0.1(6) . . . . ?
C19 C20 C21 F13 179.1(3) . . . . ?
C20 C19 C24 C23 2.1(6) . . . . ?
C20 C19 C24 F16 -179.7(3) . . . . ?
C20 C21 C22 C23 1.6(6) . . . . ?
C20 C21 C22 F14 -178.7(4) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C21 C22 C23 F15 177.4(4) . . . . ?
C22 C23 C24 C19 -0.4(6) . . . . ?
C22 C23 C24 F16 -178.7(3) . . . . ?
C24 C19 C20 C21 -1.9(6) . . . . ?
C24 C19 C20 I8 -178.8(3) . . . . ?
C25 C26 C27 C28 0.8(6) . . . . ?
C25 C26 C27 F17 -179.6(4) . . . . ?
C26 C25 C30 C29 0.4(6) . . . . ?
C26 C25 C30 F20 179.5(3) . . . . ?
C26 C27 C28 C29 -0.2(7) . . . . ?
C26 C27 C28 F18 179.8(4) . . . . ?
C27 C28 C29 C30 -0.2(7) . . . . ?
C27 C28 C29 F19 178.5(4) . . . . ?
C28 C29 C30 C25 0.1(6) . . . . ?
C28 C29 C30 F20 -179.0(4) . . . . ?
C30 C25 C26 C27 -0.8(6) . . . . ?
C30 C25 C26 I10 178.0(3) . . . . ?
C31 C32 C33 C34 0.1(6) . . . . ?
C31 C32 C33 F21 -179.7(3) . . . . ?
C32 C31 C36 C35 -0.8(6) . . . . ?
C32 C31 C36 F24 177.9(3) . . . . ?
C32 C33 C34 C35 0.4(6) . . . . ?
C32 C33 C34 F22 -179.6(4) . . . . ?
C33 C34 C35 C36 -1.1(6) . . . . ?
C33 C34 C35 F23 179.0(4) . . . . ?
C34 C35 C36 C31 1.3(6) . . . . ?
C34 C35 C36 F24 -177.5(3) . . . . ?
C36 C31 C32 C33 0.1(6) . . . . ?
C36 C31 C32 I12 -177.2(3) . . . . ?
C37 C38 C39 C40 0.1(7) . . . . ?
C37 C38 C39 F28 -179.5(4) . . . . ?
C38 C37 C42 C41 -0.2(7) . . . . ?
C38 C37 C42 F25 -179.8(4) . . . . ?
C38 C39 C40 C41 0.6(7) . . . . ?
C38 C39 C40 F27 -177.7(4) . . . . ?
C39 C40 C41 C42 -1.1(7) . . . . ?
C39 C40 C41 F26 178.6(4) . . . . ?
C40 C41 C42 C37 1.0(7) . . . . ?
C40 C41 C42 F25 -179.5(4) . . . . ?
C42 C37 C38 C39 -0.3(6) . . . . ?
C42 C37 C38 I14 -178.9(3) . . . . ?
C43 C44 C45 C46 -2.7(7) . . . . ?
C43 C44 C45 F29 178.5(4) . . . . ?
C44 C43 C48 C47 -0.1(7) . . . . ?
C44 C43 C48 F32 -179.5(4) . . . . ?
C44 C45 C46 C47 3.4(7) . . . . ?
C44 C45 C46 F30 -177.7(4) . . . . ?
C45 C46 C47 C48 -2.4(7) . . . . ?
C45 C46 C47 F31 176.8(4) . . . . ?
C46 C47 C48 C43 0.8(7) . . . . ?
C46 C47 C48 F32 -179.8(4) . . . . ?
C48 C43 C44 C45 1.0(6) . . . . ?
C48 C43 C44 I16 179.5(3) . . . . ?
C49 C50 C51 C52 -0.3(7) . . . . ?
C49 C54 C55 C56 178.3(5) . . . . ?
C49 C54 C55 C64 -0.7(5) . . . . ?
C49 C63 C64 C55 1.0(5) . . . . ?
C49 C63 C64 C59 -179.0(4) . . . . ?
C50 C49 C54 C53 1.6(6) . . . . ?
C50 C49 C54 C55 -179.0(4) . . . . ?
C50 C49 C63 C62 -0.7(9) . . . . ?
C50 C49 C63 C64 178.9(5) . . . . ?
C50 C51 C52 C53 -0.3(8) . . . . ?
C51 C52 C53 C54 1.5(7) . . . . ?
C52 C53 C54 C49 -2.1(6) . . . . ?
C52 C53 C54 C55 178.7(4) . . . . ?
C53 C54 C55 C56 -2.5(9) . . . . ?
C53 C54 C55 C64 178.6(5) . . . . ?
C54 C49 C50 C51 -0.4(7) . . . . ?
C54 C49 C63 C62 178.9(5) . . . . ?
C54 C49 C63 C64 -1.5(5) . . . . ?
C54 C55 C56 C57 -179.8(5) . . . . ?
C54 C55 C64 C59 179.8(4) . . . . ?
C54 C55 C64 C63 -0.2(5) . . . . ?
C55 C56 C57 C58 1.0(7) . . . . ?
C56 C55 C64 C59 0.6(7) . . . . ?
C56 C55 C64 C63 -179.4(4) . . . . ?
C56 C57 C58 C59 -0.6(7) . . . . ?
C57 C58 C59 C60 -178.7(5) . . . . ?
C57 C58 C59 C64 0.2(6) . . . . ?
C58 C59 C60 C61 179.3(5) . . . . ?
C58 C59 C64 C55 -0.2(6) . . . . ?
C58 C59 C64 C63 179.8(4) . . . . ?
C59 C60 C61 C62 0.7(7) . . . . ?
C60 C59 C64 C55 178.8(4) . . . . ?
C60 C59 C64 C63 -1.2(6) . . . . ?
C60 C61 C62 C63 -1.1(7) . . . . ?
C61 C62 C63 C49 -180.0(5) . . . . ?
C61 C62 C63 C64 0.4(7) . . . . ?
C62 C63 C64 C55 -179.2(4) . . . . ?
C62 C63 C64 C59 0.7(7) . . . . ?
C63 C49 C50 C51 179.2(5) . . . . ?
C63 C49 C54 C53 -178.0(4) . . . . ?
C63 C49 C54 C55 1.3(5) . . . . ?
C64 C55 C56 C57 -0.9(6) . . . . ?
C64 C59 C60 C61 0.5(7) . . . . ?
C65 C66 C67 C68 -0.7(6) . . . . ?
C65 C70 C71 C72 177.3(4) . . . . ?
C65 C70 C71 C80 -0.5(4) . . . . ?
C65 C79 C80 C71 1.3(4) . . . . ?
C65 C79 C80 C75 -179.5(4) . . . . ?
C66 C65 C70 C69 3.1(6) . . . . ?
C66 C65 C70 C71 -178.2(4) . . . . ?
C66 C65 C79 C78 -1.6(8) . . . . ?
C66 C65 C79 C80 177.9(4) . . . . ?
C66 C67 C68 C69 1.2(7) . . . . ?
C67 C68 C69 C70 0.5(6) . . . . ?
C68 C69 C70 C65 -2.6(6) . . . . ?
C68 C69 C70 C71 179.1(4) . . . . ?
C69 C70 C71 C72 -4.3(8) . . . . ?
C69 C70 C71 C80 177.9(4) . . . . ?
C70 C65 C66 C67 -1.4(6) . . . . ?
C70 C65 C79 C78 179.0(4) . . . . ?
C70 C65 C79 C80 -1.5(4) . . . . ?
C70 C71 C72 C73 -179.4(4) . . . . ?
C70 C71 C80 C75 -179.8(4) . . . . ?
C70 C71 C80 C79 -0.5(4) . . . . ?
C71 C72 C73 C74 0.4(7) . . . . ?
C72 C71 C80 C75 2.0(6) . . . . ?
C72 C71 C80 C79 -178.8(4) . . . . ?
C72 C73 C74 C75 1.2(7) . . . . ?
C73 C74 C75 C76 177.7(4) . . . . ?
C73 C74 C75 C80 -1.1(6) . . . . ?
C74 C75 C76 C77 179.5(4) . . . . ?
C74 C75 C80 C71 -0.5(6) . . . . ?
C74 C75 C80 C79 -179.6(4) . . . . ?
C75 C76 C77 C78 0.7(7) . . . . ?
C76 C75 C80 C71 -179.4(4) . . . . ?
C76 C75 C80 C79 1.4(6) . . . . ?
C76 C77 C78 C79 0.9(6) . . . . ?
C77 C78 C79 C65 178.1(4) . . . . ?
C77 C78 C79 C80 -1.3(6) . . . . ?
C78 C79 C80 C71 -179.2(4) . . . . ?
C78 C79 C80 C75 0.1(6) . . . . ?
C79 C65 C66 C67 179.2(4) . . . . ?
C79 C65 C70 C69 -177.4(3) . . . . ?
C79 C65 C70 C71 1.2(4) . . . . ?
C80 C71 C72 C73 -1.8(6) . . . . ?
C80 C75 C76 C77 -1.8(6) . . . . ?
C81 C82 C83 C84 -0.4(7) . . . . ?
C81 C86 C87 C88 176.8(5) . . . . ?
C81 C86 C87 C96 -0.7(5) . . . . ?
C81 C95 C96 C87 0.1(5) . . . . ?
C81 C95 C96 C91 -179.3(4) . . . . ?
C82 C81 C86 C85 1.4(6) . . . . ?
C82 C81 C86 C87 -179.1(4) . . . . ?
C82 C81 C95 C94 -0.5(9) . . . . ?
C82 C81 C95 C96 179.2(5) . . . . ?
C82 C83 C84 C85 1.2(7) . . . . ?
C83 C84 C85 C86 -0.6(7) . . . . ?
C84 C85 C86 C81 -0.6(7) . . . . ?
C84 C85 C86 C87 179.9(5) . . . . ?
C85 C86 C87 C88 -3.7(9) . . . . ?
C85 C86 C87 C96 178.8(5) . . . . ?
C86 C81 C82 C83 -0.9(6) . . . . ?
C86 C81 C95 C94 179.7(5) . . . . ?
C86 C81 C95 C96 -0.5(5) . . . . ?
C86 C87 C88 C89 -178.4(5) . . . . ?
C86 C87 C96 C91 179.7(4) . . . . ?
C86 C87 C96 C95 0.3(5) . . . . ?
C87 C88 C89 C90 0.6(10) . . . . ?
C88 C87 C96 C91 1.8(8) . . . . ?
C88 C87 C96 C95 -177.6(4) . . . . ?
C88 C89 C90 C91 -0.6(11) . . . . ?
C89 C90 C91 C92 178.6(7) . . . . ?
C89 C90 C91 C96 1.0(9) . . . . ?
C90 C91 C92 C93 -177.7(6) . . . . ?
C90 C91 C96 C87 -1.6(7) . . . . ?
C90 C91 C96 C95 177.7(5) . . . . ?
C91 C92 C93 C94 0.5(9) . . . . ?
C92 C91 C96 C87 -179.6(5) . . . . ?
C92 C91 C96 C95 -0.3(8) . . . . ?
C92 C93 C94 C95 -0.3(8) . . . . ?
C93 C94 C95 C81 179.5(5) . . . . ?
C93 C94 C95 C96 -0.2(7) . . . . ?
C94 C95 C96 C87 179.9(4) . . . . ?
C94 C95 C96 C91 0.5(7) . . . . ?
C95 C81 C82 C83 179.4(4) . . . . ?
C95 C81 C86 C85 -178.8(4) . . . . ?
C95 C81 C86 C87 0.7(5) . . . . ?
C96 C87 C88 C89 -1.2(8) . . . . ?
C96 C91 C92 C93 -0.2(8) . . . . ?
C97 C98 C99 C100 -0.1(8) . . . . ?
C97 C102 C103 C104 178.2(5) . . . . ?
C97 C102 C103 C112 0.7(5) . . . . ?
C97 C111 C112 C103 0.3(5) . . . . ?
C97 C111 C112 C107 -179.4(4) . . . . ?
C98 C97 C102 C101 0.6(6) . . . . ?
C98 C97 C102 C103 -179.1(4) . . . . ?
C98 C97 C111 C110 0.4(8) . . . . ?
C98 C97 C111 C112 178.5(5) . . . . ?
C98 C99 C100 C101 0.2(8) . . . . ?
C99 C100 C101 C102 0.1(8) . . . . ?
C100 C101 C102 C97 -0.5(7) . . . . ?
C100 C101 C102 C103 179.2(5) . . . . ?
C101 C102 C103 C104 -1.5(9) . . . . ?
C101 C102 C103 C112 -179.0(4) . . . . ?
C102 C97 C98 C99 -0.4(7) . . . . ?
C102 C97 C111 C110 -177.9(5) . . . . ?
C102 C97 C111 C112 0.1(4) . . . . ?
C102 C103 C104 C105 -178.2(5) . . . . ?
C102 C103 C112 C107 179.1(4) . . . . ?
C102 C103 C112 C111 -0.6(5) . . . . ?
C103 C104 C105 C106 1.0(7) . . . . ?
C104 C103 C112 C107 1.1(6) . . . . ?
C104 C103 C112 C111 -178.7(4) . . . . ?
C104 C105 C106 C107 -1.2(7) . . . . ?
C105 C106 C107 C108 179.2(4) . . . . ?
C105 C106 C107 C112 1.2(6) . . . . ?
C106 C107 C108 C109 -177.2(4) . . . . ?
C106 C107 C112 C103 -1.2(6) . . . . ?
C106 C107 C112 C111 178.5(4) . . . . ?
C107 C108 C109 C110 -1.1(7) . . . . ?
C108 C107 C112 C103 -179.4(4) . . . . ?
C108 C107 C112 C111 0.3(6) . . . . ?
C108 C109 C110 C111 0.4(7) . . . . ?
C109 C110 C111 C97 178.5(4) . . . . ?
C109 C110 C111 C112 0.7(6) . . . . ?
C110 C111 C112 C103 178.7(4) . . . . ?
C110 C111 C112 C107 -1.0(6) . . . . ?
C111 C97 C98 C99 -178.5(4) . . . . ?
C111 C97 C102 C101 179.2(4) . . . . ?
C111 C97 C102 C103 -0.5(5) . . . . ?
C112 C103 C104 C105 -0.9(6) . . . . ?
C112 C107 C108 C109 0.8(6) . . . . ?
C113 C114 C115 C116 1.5(7) . . . . ?
C113 C118 C119 C120 -178.4(5) . . . . ?
C113 C118 C119 C128 -0.9(5) . . . . ?
C113 C127 C128 C119 -1.1(5) . . . . ?
C113 C127 C128 C123 179.9(4) . . . . ?
C114 C113 C118 C117 -1.0(6) . . . . ?
C114 C113 C118 C119 -179.8(4) . . . . ?
C114 C113 C127 C126 1.3(9) . . . . ?
C114 C113 C127 C128 -179.4(5) . . . . ?
C114 C115 C116 C117 -2.1(7) . . . . ?
C115 C116 C117 C118 1.1(7) . . . . ?
C116 C117 C118 C113 0.4(7) . . . . ?
C116 C117 C118 C119 178.9(4) . . . . ?
C117 C118 C119 C120 3.0(9) . . . . ?
C117 C118 C119 C128 -179.5(5) . . . . ?
C118 C113 C114 C115 0.0(7) . . . . ?
C118 C113 C127 C126 -178.8(5) . . . . ?
C118 C113 C127 C128 0.5(5) . . . . ?
C118 C119 C120 C121 179.1(5) . . . . ?
C118 C119 C128 C123 -179.8(4) . . . . ?
C118 C119 C128 C127 1.3(5) . . . . ?
C119 C120 C121 C122 -1.2(7) . . . . ?
C120 C119 C128 C123 -1.8(7) . . . . ?
C120 C119 C128 C127 179.3(4) . . . . ?
C120 C121 C122 C123 0.4(8) . . . . ?
C121 C122 C123 C124 179.8(5) . . . . ?
C121 C122 C123 C128 -0.3(7) . . . . ?
C122 C123 C124 C125 -179.9(5) . . . . ?
C122 C123 C128 C119 1.0(7) . . . . ?
C122 C123 C128 C127 179.7(4) . . . . ?
C123 C124 C125 C126 0.9(7) . . . . ?
C124 C123 C128 C119 -179.1(4) . . . . ?
C124 C123 C128 C127 -0.3(7) . . . . ?
C124 C125 C126 C127 -1.8(7) . . . . ?
C125 C126 C127 C113 -179.1(5) . . . . ?
C125 C126 C127 C128 1.6(7) . . . . ?
C126 C127 C128 C119 178.3(4) . . . . ?
C126 C127 C128 C123 -0.6(7) . . . . ?
C127 C113 C114 C115 180.0(4) . . . . ?
C127 C113 C118 C117 179.0(4) . . . . ?
C127 C113 C118 C119 0.2(5) . . . . ?
C128 C119 C120 C121 1.8(7) . . . . ?
C128 C123 C124 C125 0.2(7) . . . . ?
C129 C130 C131 C132 0.1(8) . . . . ?
C129 C134 C135 C136 -179.4(4) . . . . ?
C129 C134 C135 C144 -0.4(4) . . . . ?
C129 C143 C144 C135 0.0(5) . . . . ?
C129 C143 C144 C139 179.3(4) . . . . ?
C130 C129 C134 C133 0.0(6) . . . . ?
C130 C129 C134 C135 -179.4(4) . . . . ?
C130 C129 C143 C142 -2.3(9) . . . . ?
C130 C129 C143 C144 179.5(5) . . . . ?
C130 C131 C132 C133 -0.1(8) . . . . ?
C131 C132 C133 C134 0.0(7) . . . . ?
C132 C133 C134 C129 0.0(7) . . . . ?
C132 C133 C134 C135 179.2(4) . . . . ?
C133 C134 C135 C136 1.3(8) . . . . ?
C133 C134 C135 C144 -179.7(5) . . . . ?
C134 C129 C130 C131 -0.1(7) . . . . ?
C134 C129 C143 C142 178.0(5) . . . . ?
C134 C129 C143 C144 -0.2(5) . . . . ?
C134 C135 C136 C137 -179.9(4) . . . . ?
C134 C135 C144 C139 -179.1(4) . . . . ?
C134 C135 C144 C143 0.2(5) . . . . ?
C135 C136 C137 C138 -1.0(6) . . . . ?
C136 C135 C144 C139 0.1(6) . . . . ?
C136 C135 C144 C143 179.5(4) . . . . ?
C136 C137 C138 C139 -0.4(6) . . . . ?
C137 C138 C139 C140 -179.0(4) . . . . ?
C137 C138 C139 C144 1.6(6) . . . . ?
C138 C139 C140 C141 -179.5(4) . . . . ?
C138 C139 C144 C135 -1.5(6) . . . . ?
C138 C139 C144 C143 179.3(4) . . . . ?
C139 C140 C141 C142 -0.1(7) . . . . ?
C140 C139 C144 C135 179.0(4) . . . . ?
C140 C139 C144 C143 -0.2(6) . . . . ?
C140 C141 C142 C143 0.5(7) . . . . ?
C141 C142 C143 C129 -178.9(5) . . . . ?
C141 C142 C143 C144 -0.8(7) . . . . ?
C142 C143 C144 C135 -178.7(4) . . . . ?
C142 C143 C144 C139 0.7(6) . . . . ?
C143 C129 C130 C131 -179.8(5) . . . . ?
C143 C129 C134 C133 179.8(4) . . . . ?
C143 C129 C134 C135 0.4(5) . . . . ?
C144 C135 C136 C137 1.1(6) . . . . ?
C144 C139 C140 C141 -0.1(6) . . . . ?
C145 C146 C147 C148 0.0(7) . . . . ?
C145 C150 C151 C152 177.7(5) . . . . ?
C145 C150 C151 C160 0.6(5) . . . . ?
C145 C159 C160 C151 0.0(5) . . . . ?
C145 C159 C160 C155 -179.1(4) . . . . ?
C146 C145 C150 C149 -0.5(7) . . . . ?
C146 C145 C150 C151 179.1(4) . . . . ?
C146 C145 C159 C158 3.1(9) . . . . ?
C146 C145 C159 C160 -179.2(5) . . . . ?
C146 C147 C148 C149 -0.8(7) . . . . ?
C147 C148 C149 C150 0.9(7) . . . . ?
C148 C149 C150 C145 -0.2(7) . . . . ?
C148 C149 C150 C151 -179.7(4) . . . . ?
C149 C150 C151 C152 -2.7(9) . . . . ?
C149 C150 C151 C160 -179.9(5) . . . . ?
C150 C145 C146 C147 0.6(7) . . . . ?
C150 C145 C159 C158 -177.4(5) . . . . ?
C150 C145 C159 C160 0.4(5) . . . . ?
C150 C151 C152 C153 -178.0(4) . . . . ?
C150 C151 C160 C155 178.7(4) . . . . ?
C150 C151 C160 C159 -0.3(5) . . . . ?
C151 C152 C153 C154 0.3(7) . . . . ?
C152 C151 C160 C155 1.1(6) . . . . ?
C152 C151 C160 C159 -178.0(4) . . . . ?
C152 C153 C154 C155 0.8(7) . . . . ?
C153 C154 C155 C156 177.0(5) . . . . ?
C153 C154 C155 C160 -0.9(6) . . . . ?
C154 C155 C156 C157 -178.3(5) . . . . ?
C154 C155 C160 C151 0.0(6) . . . . ?
C154 C155 C160 C159 179.0(4) . . . . ?
C155 C156 C157 C158 0.2(7) . . . . ?
C156 C155 C160 C151 -178.2(4) . . . . ?
C156 C155 C160 C159 0.8(6) . . . . ?
C156 C157 C158 C159 -0.3(7) . . . . ?
C157 C158 C159 C145 178.1(5) . . . . ?
C157 C158 C159 C160 0.6(6) . . . . ?
C158 C159 C160 C151 178.2(4) . . . . ?
C158 C159 C160 C155 -0.9(7) . . . . ?
C159 C145 C146 C147 -179.8(4) . . . . ?
C159 C145 C150 C149 179.8(4) . . . . ?
C159 C145 C150 C151 -0.6(5) . . . . ?
C160 C151 C152 C153 -1.2(6) . . . . ?
C160 C155 C156 C157 -0.4(6) . . . . ?
C161 C162 C163 C164 0.6(6) . . . . ?
C161 C166 C167 C168 -177.8(4) . . . . ?
C161 C166 C167 C176 0.7(4) . . . . ?
C161 C175 C176 C167 0.5(4) . . . . ?
C161 C175 C176 C171 179.2(4) . . . . ?
C162 C161 C166 C165 -1.0(6) . . . . ?
C162 C161 C166 C167 179.4(4) . . . . ?
C162 C161 C175 C174 -1.3(8) . . . . ?
C162 C161 C175 C176 -179.8(4) . . . . ?
C162 C163 C164 C165 -0.7(7) . . . . ?
C163 C164 C165 C166 -0.1(6) . . . . ?
C164 C165 C166 C161 0.9(6) . . . . ?
C164 C165 C166 C167 -179.6(4) . . . . ?
C165 C166 C167 C168 2.7(8) . . . . ?
C165 C166 C167 C176 -178.8(4) . . . . ?
C166 C161 C162 C163 0.2(6) . . . . ?
C166 C161 C175 C174 178.5(5) . . . . ?
C166 C161 C175 C176 0.0(4) . . . . ?
C166 C167 C168 C169 178.5(4) . . . . ?
C166 C167 C176 C171 -179.5(4) . . . . ?
C166 C167 C176 C175 -0.7(5) . . . . ?
C167 C168 C169 C170 0.5(6) . . . . ?
C168 C167 C176 C171 -0.7(6) . . . . ?
C168 C167 C176 C175 178.0(4) . . . . ?
C168 C169 C170 C171 -0.7(7) . . . . ?
C169 C170 C171 C172 -177.3(4) . . . . ?
C169 C170 C171 C176 0.2(6) . . . . ?
C170 C171 C172 C173 177.3(4) . . . . ?
C170 C171 C176 C167 0.5(6) . . . . ?
C170 C171 C176 C175 -178.1(4) . . . . ?
C171 C172 C173 C174 0.6(6) . . . . ?
C172 C171 C176 C167 178.3(4) . . . . ?
C172 C171 C176 C175 -0.3(6) . . . . ?
C172 C173 C174 C175 -0.5(6) . . . . ?
C173 C174 C175 C161 -178.3(4) . . . . ?
C173 C174 C175 C176 0.0(6) . . . . ?
C174 C175 C176 C167 -178.3(4) . . . . ?
C174 C175 C176 C171 0.4(6) . . . . ?
C175 C161 C162 C163 -180.0(4) . . . . ?
C175 C161 C166 C165 179.1(4) . . . . ?
C175 C161 C166 C167 -0.4(4) . . . . ?
C176 C167 C168 C169 0.2(6) . . . . ?
C176 C171 C172 C173 -0.2(6) . . . . ?
F1 C3 C4 C5 179.5(4) . . . . ?
F1 C3 C4 F2 2.0(6) . . . . ?
F2 C4 C5 C6 177.1(4) . . . . ?
F2 C4 C5 F3 -3.1(6) . . . . ?
F3 C5 C6 C1 -179.6(4) . . . . ?
F3 C5 C6 F4 0.9(6) . . . . ?
F5 C9 C10 C11 -179.5(4) . . . . ?
F5 C9 C10 F6 1.8(6) . . . . ?
F6 C10 C11 C12 179.5(4) . . . . ?
F6 C10 C11 F7 -1.5(7) . . . . ?
F7 C11 C12 C7 179.3(4) . . . . ?
F7 C11 C12 F8 0.1(6) . . . . ?
F9 C15 C16 C17 -177.1(4) . . . . ?
F9 C15 C16 F10 0.7(6) . . . . ?
F10 C16 C17 C18 -179.8(4) . . . . ?
F10 C16 C17 F11 -0.5(6) . . . . ?
F11 C17 C18 C13 -179.1(4) . . . . ?
F11 C17 C18 F12 0.6(6) . . . . ?
F13 C21 C22 C23 -177.4(3) . . . . ?
F13 C21 C22 F14 2.3(6) . . . . ?
F14 C22 C23 C24 178.9(3) . . . . ?
F14 C22 C23 F15 -2.3(6) . . . . ?
F15 C23 C24 C19 -179.2(3) . . . . ?
F15 C23 C24 F16 2.5(6) . . . . ?
F17 C27 C28 C29 -179.8(4) . . . . ?
F17 C27 C28 F18 0.2(6) . . . . ?
F18 C28 C29 C30 179.7(4) . . . . ?
F18 C28 C29 F19 -1.6(6) . . . . ?
F19 C29 C30 C25 -178.6(4) . . . . ?
F19 C29 C30 F20 2.4(6) . . . . ?
F21 C33 C34 C35 -179.8(4) . . . . ?
F21 C33 C34 F22 0.2(6) . . . . ?
F22 C34 C35 C36 178.9(4) . . . . ?
F22 C34 C35 F23 -1.1(6) . . . . ?
F23 C35 C36 C31 -178.7(4) . . . . ?
F23 C35 C36 F24 2.4(6) . . . . ?
F26 C41 C42 C37 -178.8(4) . . . . ?
F26 C41 C42 F25 0.8(6) . . . . ?
F27 C40 C41 C42 177.1(4) . . . . ?
F27 C40 C41 F26 -3.2(6) . . . . ?
F28 C39 C40 C41 -179.7(4) . . . . ?
F28 C39 C40 F27 2.0(6) . . . . ?
F29 C45 C46 C47 -177.7(4) . . . . ?
F29 C45 C46 F30 1.2(6) . . . . ?
F30 C46 C47 C48 178.7(4) . . . . ?
F30 C46 C47 F31 -2.2(6) . . . . ?
F31 C47 C48 C43 -178.3(4) . . . . ?
F31 C47 C48 F32 1.1(6) . . . . ?
I1 C1 C2 C3 179.8(3) . . . . ?
I1 C1 C2 I2 -0.4(5) . . . . ?
I1 C1 C6 C5 -179.3(3) . . . . ?
I1 C1 C6 F4 0.1(5) . . . . ?
I2 C2 C3 C4 178.9(3) . . . . ?
I2 C2 C3 F1 0.5(5) . . . . ?
I3 C7 C8 C9 179.9(3) . . . . ?
I3 C7 C8 I4 -1.6(5) . . . . ?
I3 C7 C12 C11 -178.4(3) . . . . ?
I3 C7 C12 F8 0.7(6) . . . . ?
I4 C8 C9 C10 -179.8(3) . . . . ?
I4 C8 C9 F5 0.3(6) . . . . ?
I5 C13 C14 C15 -178.6(3) . . . . ?
I5 C13 C14 I6 0.7(5) . . . . ?
I5 C13 C18 C17 179.5(3) . . . . ?
I5 C13 C18 F12 -0.2(5) . . . . ?
I6 C14 C15 C16 178.6(3) . . . . ?
I6 C14 C15 F9 -1.3(5) . . . . ?
I7 C19 C20 C21 179.8(3) . . . . ?
I7 C19 C20 I8 2.9(5) . . . . ?
I7 C19 C24 C23 -179.5(3) . . . . ?
I7 C19 C24 F16 -1.2(5) . . . . ?
I8 C20 C21 C22 177.2(3) . . . . ?
I8 C20 C21 F13 -3.8(5) . . . . ?
I9 C25 C26 C27 -179.5(3) . . . . ?
I9 C25 C26 I10 -0.6(5) . . . . ?
I9 C25 C30 C29 179.2(3) . . . . ?
I9 C25 C30 F20 -1.8(5) . . . . ?
I10 C26 C27 C28 -178.2(3) . . . . ?
I10 C26 C27 F17 1.4(5) . . . . ?
I11 C31 C32 C33 -179.7(3) . . . . ?
I11 C31 C32 I12 2.9(5) . . . . ?
I11 C31 C36 C35 179.0(3) . . . . ?
I11 C31 C36 F24 -2.2(5) . . . . ?
I12 C32 C33 C34 177.6(3) . . . . ?
I12 C32 C33 F21 -2.2(5) . . . . ?
I13 C37 C38 C39 -179.4(3) . . . . ?
I13 C37 C38 I14 2.0(5) . . . . ?
I13 C37 C42 C41 178.9(3) . . . . ?
I13 C37 C42 F25 -0.7(6) . . . . ?
I14 C38 C39 C40 178.8(3) . . . . ?
I14 C38 C39 F28 -0.9(6) . . . . ?
I15 C43 C44 C45 -178.1(3) . . . . ?
I15 C43 C44 I16 0.5(5) . . . . ?
I15 C43 C48 C47 179.1(3) . . . . ?
I15 C43 C48 F32 -0.3(6) . . . . ?
I16 C44 C45 C46 178.6(3) . . . . ?
I16 C44 C45 F29 -0.2(5) . . . . ?

_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.752
####################################################################### 
# 
# 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_20161116c
_database_code_depnum_ccdc_archive 'CCDC 1547632'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        14DBrPB-FA
_chemical_formula_moiety         'Br2 C6 F4, C16 H10'
_chemical_formula_sum            'C22 H10 Br2 F4'
_chemical_formula_weight         510.12
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2059(5)
_cell_length_b                   8.3166(5)
_cell_length_c                   14.8296(12)
_cell_angle_alpha                90.772(6)
_cell_angle_beta                 92.296(6)
_cell_angle_gamma                91.587(5)
_cell_volume                     887.57(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.5500
_cell_measurement_theta_min      3.6880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7250
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.906
_diffrn_reflns_theta_min         3.657
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  43.00   1.00    1.00    --   12.76 -77.00 -90.00  106
  2  ω     -7.00  28.00   1.00    1.00    --  -11.04 -99.00  30.00   35
  3  ω    -12.00  54.00   1.00    1.00    --   12.76 -99.00  30.00   66
  4  ω    -57.00  40.00   1.00    1.00    --   12.76 -57.00 150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0186885000
_diffrn_orient_matrix_UB_12      0.0151971000
_diffrn_orient_matrix_UB_13      0.0467078000
_diffrn_orient_matrix_UB_21      -0.0772831000
_diffrn_orient_matrix_UB_22      -0.0501430000
_diffrn_orient_matrix_UB_23      0.0103132000
_diffrn_orient_matrix_UB_31      0.0582279000
_diffrn_orient_matrix_UB_32      -0.0673479000
_diffrn_orient_matrix_UB_33      0.0019749000
_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                2946
_reflns_number_total             4178
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      0.985
_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0980
_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:
 C15(H15), C11(H11), C14(H14), C16(H16), C20(H20), C8(H8), C22(H22), C10(H10),
 C21(H21), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.98650(6) 1.03117(5) 0.13282(3) 0.02861(14) Uani 1 1 d . . . . .
Br2 Br 0.97255(6) 0.36886(5) 0.36304(3) 0.02881(14) Uani 1 1 d . . . . .
F2 F 1.1264(3) 0.7009(3) 0.41930(15) 0.0276(6) Uani 1 1 d . . . . .
F3 F 0.8572(3) 0.4203(3) 0.16531(17) 0.0268(6) Uani 1 1 d . . . . .
F4 F 0.8645(3) 0.6914(3) 0.07110(16) 0.0269(6) Uani 1 1 d . . . . .
F1 F 1.1313(3) 0.9734(3) 0.32501(17) 0.0277(6) Uani 1 1 d . . . . .
C1 C 0.9952(5) 0.8389(4) 0.1965(3) 0.0173(9) Uani 1 1 d . . . . .
C3 C 1.0609(5) 0.6973(5) 0.3335(3) 0.0173(9) Uani 1 1 d . . . . .
C5 C 0.9253(5) 0.5557(4) 0.2063(3) 0.0168(9) Uani 1 1 d . . . . .
C4 C 0.9883(5) 0.5554(4) 0.2953(3) 0.0167(9) Uani 1 1 d . . . . .
C6 C 0.9290(5) 0.6953(5) 0.1571(3) 0.0174(9) Uani 1 1 d . . . . .
C13 C 0.4963(5) 0.5672(4) 0.2926(3) 0.0149(8) Uani 1 1 d . . . . .
C12 C 0.5728(5) 0.6992(4) 0.3520(3) 0.0160(9) Uani 1 1 d . . . . .
C15 C 0.3814(5) 0.3180(5) 0.2275(3) 0.0215(10) Uani 1 1 d . . . . .
H15 H 0.3560 0.2086 0.2341 0.026 Uiso 1 1 calc R . . . .
C2 C 1.0628(5) 0.8360(4) 0.2847(3) 0.0191(9) Uani 1 1 d . . . . .
C11 C 0.6379(5) 0.7008(5) 0.4417(3) 0.0203(9) Uani 1 1 d . . . . .
H11 H 0.6374 0.6072 0.4753 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5770(5) 0.8424(4) 0.3011(3) 0.0150(8) Uani 1 1 d . . . . .
C19 C 0.5022(5) 0.8044(4) 0.2095(3) 0.0158(9) Uani 1 1 d . . . . .
C14 C 0.4582(5) 0.4068(4) 0.3026(3) 0.0188(9) Uani 1 1 d . . . . .
H14 H 0.4823 0.3572 0.3575 0.023 Uiso 1 1 calc R . . . .
C16 C 0.3429(5) 0.3853(5) 0.1454(3) 0.0208(9) Uani 1 1 d . . . . .
H16 H 0.2915 0.3222 0.0980 0.025 Uiso 1 1 calc R . . . .
C20 C 0.4696(5) 0.8883(5) 0.1320(3) 0.0205(9) Uani 1 1 d . . . . .
H20 H 0.4971 0.9981 0.1301 0.025 Uiso 1 1 calc R . . . .
C18 C 0.4564(5) 0.6361(4) 0.2080(3) 0.0163(9) Uani 1 1 d . . . . .
C8 C 0.6464(5) 0.9856(4) 0.3403(3) 0.0177(9) Uani 1 1 d . . . . .
H8 H 0.6514 1.0794 0.3070 0.021 Uiso 1 1 calc R . . . .
C17 C 0.3815(5) 0.5526(5) 0.1324(3) 0.0175(9) Uani 1 1 d . . . . .
C22 C 0.3508(5) 0.6435(5) 0.0532(3) 0.0210(9) Uani 1 1 d . . . . .
H22 H 0.3021 0.5935 0.0006 0.025 Uiso 1 1 calc R . . . .
C10 C 0.7040(6) 0.8467(5) 0.4798(3) 0.0242(10) Uani 1 1 d . . . . .
H10 H 0.7461 0.8500 0.5399 0.029 Uiso 1 1 calc R . . . .
C21 C 0.3930(6) 0.8047(5) 0.0545(3) 0.0246(10) Uani 1 1 d . . . . .
H21 H 0.3704 0.8625 0.0021 0.030 Uiso 1 1 calc R . . . .
C9 C 0.7083(6) 0.9861(5) 0.4305(3) 0.0244(10) Uani 1 1 d . . . . .
H9 H 0.7530 1.0816 0.4578 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.869(4) . ?
Br2 C4 1.863(4) . ?
F2 C3 1.339(4) . ?
F3 C5 1.343(4) . ?
F4 C6 1.339(4) . ?
F1 C2 1.354(4) . ?
C1 C6 1.386(5) . ?
C1 C2 1.378(5) . ?
C3 C4 1.383(5) . ?
C3 C2 1.370(5) . ?
C5 C4 1.378(5) . ?
C5 C6 1.380(5) . ?
C13 C12 1.478(5) . ?
C13 C14 1.366(5) . ?
C13 C18 1.409(5) . ?
C12 C11 1.394(5) . ?
C12 C7 1.418(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.414(6) . ?
C15 C16 1.369(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.394(5) . ?
C7 C19 1.468(5) . ?
C7 C8 1.391(5) . ?
C19 C20 1.368(5) . ?
C19 C18 1.429(5) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.428(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.419(6) . ?
C18 C17 1.393(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(6) . ?
C17 C22 1.418(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.367(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.380(6) . ?
C21 H21 0.9300 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 Br1 120.9(3) . . ?
C2 C1 Br1 121.1(3) . . ?
C2 C1 C6 117.9(4) . . ?
F2 C3 C4 120.1(4) . . ?
F2 C3 C2 119.5(4) . . ?
C2 C3 C4 120.4(4) . . ?
F3 C5 C4 120.9(3) . . ?
F3 C5 C6 118.1(4) . . ?
C4 C5 C6 120.9(4) . . ?
C3 C4 Br2 120.8(3) . . ?
C5 C4 Br2 120.7(3) . . ?
C5 C4 C3 118.5(4) . . ?
F4 C6 C1 120.2(4) . . ?
F4 C6 C5 119.3(3) . . ?
C5 C6 C1 120.5(4) . . ?
C14 C13 C12 135.4(4) . . ?
C14 C13 C18 118.4(4) . . ?
C18 C13 C12 106.3(3) . . ?
C11 C12 C13 131.5(4) . . ?
C11 C12 C7 120.3(4) . . ?
C7 C12 C13 108.2(3) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C16 C15 C14 123.1(4) . . ?
F1 C2 C1 119.7(3) . . ?
F1 C2 C3 118.7(4) . . ?
C3 C2 C1 121.6(4) . . ?
C12 C11 H11 120.9 . . ?
C12 C11 C10 118.2(4) . . ?
C10 C11 H11 120.9 . . ?
C12 C7 C19 108.3(3) . . ?
C8 C7 C12 120.3(4) . . ?
C8 C7 C19 131.4(4) . . ?
C20 C19 C7 136.1(4) . . ?
C20 C19 C18 117.9(4) . . ?
C18 C19 C7 106.1(3) . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(4) . . ?
C17 C16 H16 120.0 . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.8(4) . . ?
C21 C20 H20 120.6 . . ?
C13 C18 C19 111.2(3) . . ?
C17 C18 C13 124.9(4) . . ?
C17 C18 C19 123.9(4) . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C18 C17 C16 115.2(4) . . ?
C18 C17 C22 116.6(4) . . ?
C22 C17 C16 128.2(4) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.7(4) . . ?
C21 C22 H22 120.1 . . ?
C11 C10 H10 119.2 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H10 119.2 . . ?
C20 C21 H21 118.4 . . ?
C22 C21 C20 123.1(4) . . ?
C22 C21 H21 118.4 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?

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 C6 F4 2.7(5) . . . . ?
Br1 C1 C6 C5 -176.0(3) . . . . ?
Br1 C1 C2 F1 -2.8(5) . . . . ?
Br1 C1 C2 C3 176.6(3) . . . . ?
F2 C3 C4 Br2 2.1(5) . . . . ?
F2 C3 C4 C5 -178.9(3) . . . . ?
F2 C3 C2 F1 0.0(5) . . . . ?
F2 C3 C2 C1 -179.3(3) . . . . ?
F3 C5 C4 Br2 -2.4(5) . . . . ?
F3 C5 C4 C3 178.5(3) . . . . ?
F3 C5 C6 F4 0.3(5) . . . . ?
F3 C5 C6 C1 179.0(3) . . . . ?
C4 C3 C2 F1 178.6(3) . . . . ?
C4 C3 C2 C1 -0.8(6) . . . . ?
C4 C5 C6 F4 -179.2(3) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C6 C1 C2 F1 179.0(3) . . . . ?
C6 C1 C2 C3 -1.7(6) . . . . ?
C6 C5 C4 Br2 177.0(3) . . . . ?
C6 C5 C4 C3 -2.0(6) . . . . ?
C13 C12 C11 C10 179.6(4) . . . . ?
C13 C12 C7 C19 0.5(4) . . . . ?
C13 C12 C7 C8 -178.9(3) . . . . ?
C13 C18 C17 C16 0.7(6) . . . . ?
C13 C18 C17 C22 179.8(4) . . . . ?
C12 C13 C14 C15 179.5(4) . . . . ?
C12 C13 C18 C19 -0.2(4) . . . . ?
C12 C13 C18 C17 -179.9(4) . . . . ?
C12 C11 C10 C9 -1.0(6) . . . . ?
C12 C7 C19 C20 179.3(4) . . . . ?
C12 C7 C19 C18 -0.6(4) . . . . ?
C12 C7 C8 C9 -1.1(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C15 C16 C17 C22 -179.7(4) . . . . ?
C2 C1 C6 F4 -179.0(3) . . . . ?
C2 C1 C6 C5 2.3(6) . . . . ?
C2 C3 C4 Br2 -176.4(3) . . . . ?
C2 C3 C4 C5 2.6(6) . . . . ?
C11 C12 C7 C19 179.4(3) . . . . ?
C11 C12 C7 C8 0.1(6) . . . . ?
C11 C10 C9 C8 -0.1(6) . . . . ?
C7 C12 C11 C10 1.0(6) . . . . ?
C7 C19 C20 C21 179.9(4) . . . . ?
C7 C19 C18 C13 0.5(4) . . . . ?
C7 C19 C18 C17 -179.8(4) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C19 C7 C8 C9 179.7(4) . . . . ?
C19 C20 C21 C22 -0.4(6) . . . . ?
C19 C18 C17 C16 -179.1(3) . . . . ?
C19 C18 C17 C22 0.1(6) . . . . ?
C14 C13 C12 C11 1.7(7) . . . . ?
C14 C13 C12 C7 -179.5(4) . . . . ?
C14 C13 C18 C19 179.3(3) . . . . ?
C14 C13 C18 C17 -0.5(6) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C16 C15 C14 C13 -0.2(6) . . . . ?
C16 C17 C22 C21 178.4(4) . . . . ?
C20 C19 C18 C13 -179.4(3) . . . . ?
C20 C19 C18 C17 0.3(6) . . . . ?
C18 C13 C12 C11 -179.0(4) . . . . ?
C18 C13 C12 C7 -0.2(4) . . . . ?
C18 C13 C14 C15 0.2(5) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C18 C17 C22 C21 -0.6(6) . . . . ?
C8 C7 C19 C20 -1.4(8) . . . . ?
C8 C7 C19 C18 178.7(4) . . . . ?
C17 C22 C21 C20 0.8(6) . . . . ?

_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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_20161213b
_database_code_depnum_ccdc_archive 'CCDC 1547631'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        13DBrPB
_chemical_formula_moiety         'Br2 C6 F4, C16 H10'
_chemical_formula_sum            'C22 H10 Br2 F4'
_chemical_formula_weight         510.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1Br1
_chemical_oxdiff_usercomment     Eu
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'
Br Br -0.2901 2.4595 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.8502(7)
_cell_length_b                   8.0650(7)
_cell_length_c                   17.0969(16)
_cell_angle_alpha                97.180(8)
_cell_angle_beta                 100.583(8)
_cell_angle_gamma                100.330(8)
_cell_volume                     901.17(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      25.9480
_cell_measurement_theta_min      3.4930
_exptl_absorpt_coefficient_mu    4.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0878
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6885
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.27
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.8270
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  81.00   1.00    2.00    --   12.76  37.00 -60.00   90
  2  ω    -16.00  30.00   1.00    2.00    --  -11.04 -99.00 120.00   46
  3  ω    -32.00  49.00   1.00    2.00    --   12.76 -88.00  82.00   81
  4  ω     67.00  95.00   1.00    2.00    --   12.76-178.00  90.00   28
  5  ω    -49.00  50.00   1.00    2.00    --   12.76   0.00  90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0538840000
_diffrn_orient_matrix_UB_12      -0.0701078000
_diffrn_orient_matrix_UB_13      -0.0300761000
_diffrn_orient_matrix_UB_21      -0.0717163000
_diffrn_orient_matrix_UB_22      -0.0201785000
_diffrn_orient_matrix_UB_23      0.0242706000
_diffrn_orient_matrix_UB_31      -0.0595633000
_diffrn_orient_matrix_UB_32      0.0537447000
_diffrn_orient_matrix_UB_33      -0.0183419000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2448
_reflns_number_total             3299
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0406P)²+0.2056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C19(H19), C27(H27), C22(H22), C20(H20), C28(H28), C14(H14),
 C24(H24), C25(H25), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br7 Br 0.38192(9) 0.98183(9) 0.89749(3) 0.0354(2) Uani 1 d . . .
Br8 Br 0.28471(10) 0.93638(10) 0.55950(4) 0.0449(2) Uani 1 d . . .
F12 F 0.3738(5) 1.0970(4) 0.73532(19) 0.0327(8) Uani 1 d . . .
F11 F 0.1841(5) 0.5580(5) 0.57056(18) 0.0399(9) Uani 1 d . . .
F9 F 0.2586(5) 0.5950(5) 0.84889(19) 0.0382(9) Uani 1 d . . .
F10 F 0.1771(5) 0.4061(4) 0.7012(2) 0.0415(9) Uani 1 d . . .
C2 C 0.3257(7) 0.9265(7) 0.7272(3) 0.0218(13) Uani 1 d . . .
C1 C 0.3192(8) 0.8481(7) 0.7940(3) 0.0217(12) Uani 1 d . . .
C16 C 0.2256(8) 0.2575(7) 0.2615(3) 0.0233(13) Uani 1 d . . .
C26 C 0.1261(8) -0.0188(7) 0.1799(3) 0.0247(13) Uani 1 d . . .
H26 H 0.0939 -0.0904 0.1303 0.030 Uiso 1 calc . . R
C4 C 0.2317(8) 0.6563(8) 0.6433(3) 0.0258(13) Uani 1 d . . .
C23 C 0.1820(8) 0.1553(7) 0.1849(3) 0.0242(13) Uani 1 d . . .
C15 C 0.2167(8) 0.1945(7) 0.3333(3) 0.0233(13) Uani 1 d . . .
C19 C 0.3069(8) 0.5767(7) 0.1284(3) 0.0237(13) Uani 1 d . . .
H19 H 0.3485 0.6881 0.1562 0.028 Uiso 1 calc . . R
C13 C 0.2078(7) 0.2740(7) 0.1270(3) 0.0216(13) Uani 1 d . . .
C27 C 0.1187(8) -0.0871(8) 0.2524(3) 0.0291(14) Uani 1 d . . .
H27 H 0.0834 -0.2049 0.2495 0.035 Uiso 1 calc . . R
C17 C 0.2788(8) 0.4329(7) 0.2558(3) 0.0232(13) Uani 1 d . . .
C18 C 0.2693(8) 0.4422(7) 0.1696(3) 0.0208(12) Uani 1 d . . .
C6 C 0.2684(8) 0.6733(7) 0.7846(3) 0.0221(13) Uani 1 d . . .
C22 C 0.1847(7) 0.2434(7) 0.0435(3) 0.0216(12) Uani 1 d . . .
H22 H 0.1444 0.1325 0.0152 0.026 Uiso 1 calc . . R
C20 C 0.2822(9) 0.5445(8) 0.0452(3) 0.0308(14) Uani 1 d . . .
H20 H 0.3062 0.6354 0.0173 0.037 Uiso 1 calc . . R
C28 C 0.1615(8) 0.0146(7) 0.3260(3) 0.0274(13) Uani 1 d . . .
H28 H 0.1543 -0.0350 0.3719 0.033 Uiso 1 calc . . R
C14 C 0.2678(8) 0.3192(9) 0.4038(3) 0.0303(15) Uani 1 d . . .
H14 H 0.2630 0.2852 0.4536 0.036 Uiso 1 calc . . R
C24 C 0.3310(8) 0.5495(8) 0.3259(3) 0.0284(14) Uani 1 d . . .
H24 H 0.3700 0.6656 0.3247 0.034 Uiso 1 calc . . R
C25 C 0.3242(8) 0.4893(8) 0.3999(3) 0.0308(15) Uani 1 d . . .
H25 H 0.3593 0.5678 0.4474 0.037 Uiso 1 calc . . R
C21 C 0.2225(8) 0.3801(8) 0.0030(3) 0.0276(13) Uani 1 d . . .
H21 H 0.2077 0.3611 -0.0527 0.033 Uiso 1 calc . . R
C3 C 0.2809(8) 0.8313(8) 0.6506(3) 0.0250(13) Uani 1 d . . .
C5 C 0.2241(8) 0.5769(8) 0.7098(3) 0.0281(14) Uani 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
Br7 C1 1.886(5) . ?
Br8 C3 1.866(5) . ?
F12 C2 1.338(6) . ?
F11 C4 1.339(6) . ?
F9 C6 1.340(6) . ?
F10 C5 1.340(7) . ?
C2 C1 1.376(7) . ?
C2 C3 1.384(7) . ?
C1 C6 1.372(8) . ?
C16 C23 1.408(7) . ?
C16 C15 1.393(7) . ?
C16 C17 1.416(8) . ?
C26 H26 0.9300 . ?
C26 C23 1.375(8) . ?
C26 C27 1.422(7) . ?
C4 C3 1.375(8) . ?
C4 C5 1.376(8) . ?
C23 C13 1.472(7) . ?
C15 C28 1.416(8) . ?
C15 C14 1.416(8) . ?
C19 H19 0.9300 . ?
C19 C18 1.377(7) . ?
C19 C20 1.388(7) . ?
C13 C18 1.409(8) . ?
C13 C22 1.393(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(8) . ?
C17 C18 1.475(7) . ?
C17 C24 1.374(7) . ?
C6 C5 1.363(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(8) . ?
C28 H28 0.9300 . ?
C14 H14 0.9300 . ?
C14 C25 1.370(9) . ?
C24 H24 0.9300 . ?
C24 C25 1.416(7) . ?
C25 H25 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F12 C2 C1 120.3(5) . . ?
F12 C2 C3 118.8(5) . . ?
C1 C2 C3 120.9(5) . . ?
C2 C1 Br7 119.7(4) . . ?
C6 C1 Br7 120.6(4) . . ?
C6 C1 C2 119.6(5) . . ?
C23 C16 C17 111.0(5) . . ?
C15 C16 C23 124.5(5) . . ?
C15 C16 C17 124.5(5) . . ?
C23 C26 H26 120.7 . . ?
C23 C26 C27 118.5(5) . . ?
C27 C26 H26 120.7 . . ?
F11 C4 C3 120.6(5) . . ?
F11 C4 C5 118.0(5) . . ?
C3 C4 C5 121.4(5) . . ?
C16 C23 C13 106.1(5) . . ?
C26 C23 C16 118.2(5) . . ?
C26 C23 C13 135.7(5) . . ?
C16 C15 C28 115.7(5) . . ?
C16 C15 C14 115.5(5) . . ?
C14 C15 C28 128.8(5) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(5) . . ?
C20 C19 H19 120.3 . . ?
C18 C13 C23 108.9(5) . . ?
C22 C13 C23 130.9(5) . . ?
C22 C13 C18 120.2(5) . . ?
C26 C27 H27 118.9 . . ?
C28 C27 C26 122.2(6) . . ?
C28 C27 H27 118.9 . . ?
C16 C17 C18 106.6(5) . . ?
C24 C17 C16 118.2(5) . . ?
C24 C17 C18 135.2(6) . . ?
C19 C18 C13 119.8(5) . . ?
C19 C18 C17 132.8(5) . . ?
C13 C18 C17 107.4(5) . . ?
F9 C6 C1 120.4(5) . . ?
F9 C6 C5 119.1(5) . . ?
C5 C6 C1 120.5(5) . . ?
C13 C22 H22 120.4 . . ?
C21 C22 C13 119.2(5) . . ?
C21 C22 H22 120.4 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(5) . . ?
C21 C20 H20 119.4 . . ?
C15 C28 H28 119.6 . . ?
C27 C28 C15 120.9(5) . . ?
C27 C28 H28 119.6 . . ?
C15 C14 H14 119.5 . . ?
C25 C14 C15 121.0(5) . . ?
C25 C14 H14 119.5 . . ?
C17 C24 H24 120.7 . . ?
C17 C24 C25 118.6(6) . . ?
C25 C24 H24 120.7 . . ?
C14 C25 C24 122.3(6) . . ?
C14 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
C2 C3 Br8 121.2(5) . . ?
C4 C3 Br8 120.7(4) . . ?
C4 C3 C2 118.1(5) . . ?
F10 C5 C4 120.4(5) . . ?
F10 C5 C6 120.1(5) . . ?
C6 C5 C4 119.5(6) . . ?

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
Br7 C1 C6 F9 1.4(7) . . . . ?
Br7 C1 C6 C5 -179.7(4) . . . . ?
F12 C2 C1 Br7 -0.8(6) . . . . ?
F12 C2 C1 C6 179.6(4) . . . . ?
F12 C2 C3 Br8 -0.5(6) . . . . ?
F12 C2 C3 C4 -180.0(5) . . . . ?
F11 C4 C3 Br8 -0.5(7) . . . . ?
F11 C4 C3 C2 179.0(4) . . . . ?
F11 C4 C5 F10 2.3(7) . . . . ?
F11 C4 C5 C6 -179.0(4) . . . . ?
F9 C6 C5 F10 -1.9(7) . . . . ?
F9 C6 C5 C4 179.3(4) . . . . ?
C2 C1 C6 F9 -179.0(4) . . . . ?
C2 C1 C6 C5 -0.1(8) . . . . ?
C1 C2 C3 Br8 178.9(4) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C1 C6 C5 F10 179.1(5) . . . . ?
C1 C6 C5 C4 0.4(8) . . . . ?
C16 C23 C13 C18 1.1(5) . . . . ?
C16 C23 C13 C22 179.9(5) . . . . ?
C16 C15 C28 C27 -0.6(7) . . . . ?
C16 C15 C14 C25 -0.8(7) . . . . ?
C16 C17 C18 C19 -179.2(5) . . . . ?
C16 C17 C18 C13 1.1(5) . . . . ?
C16 C17 C24 C25 -1.6(7) . . . . ?
C26 C23 C13 C18 179.9(6) . . . . ?
C26 C23 C13 C22 -1.2(10) . . . . ?
C26 C27 C28 C15 -0.3(8) . . . . ?
C23 C16 C15 C28 0.7(7) . . . . ?
C23 C16 C15 C14 179.6(5) . . . . ?
C23 C16 C17 C18 -0.4(6) . . . . ?
C23 C16 C17 C24 -178.3(4) . . . . ?
C23 C26 C27 C28 1.2(8) . . . . ?
C23 C13 C18 C19 178.9(4) . . . . ?
C23 C13 C18 C17 -1.3(5) . . . . ?
C23 C13 C22 C21 -178.8(5) . . . . ?
C15 C16 C23 C26 0.2(8) . . . . ?
C15 C16 C23 C13 179.2(4) . . . . ?
C15 C16 C17 C18 180.0(5) . . . . ?
C15 C16 C17 C24 2.0(7) . . . . ?
C15 C14 C25 C24 1.2(8) . . . . ?
C19 C20 C21 C22 0.4(8) . . . . ?
C13 C22 C21 C20 -0.1(8) . . . . ?
C27 C26 C23 C16 -1.1(7) . . . . ?
C27 C26 C23 C13 -179.8(5) . . . . ?
C17 C16 C23 C26 -179.5(5) . . . . ?
C17 C16 C23 C13 -0.4(6) . . . . ?
C17 C16 C15 C28 -179.6(5) . . . . ?
C17 C16 C15 C14 -0.8(7) . . . . ?
C17 C24 C25 C14 0.1(8) . . . . ?
C18 C19 C20 C21 -0.6(8) . . . . ?
C18 C13 C22 C21 -0.1(7) . . . . ?
C18 C17 C24 C25 -178.8(5) . . . . ?
C22 C13 C18 C19 -0.1(7) . . . . ?
C22 C13 C18 C17 179.7(4) . . . . ?
C20 C19 C18 C13 0.5(7) . . . . ?
C20 C19 C18 C17 -179.3(5) . . . . ?
C28 C15 C14 C25 177.9(5) . . . . ?
C14 C15 C28 C27 -179.3(5) . . . . ?
C24 C17 C18 C19 -1.7(10) . . . . ?
C24 C17 C18 C13 178.5(5) . . . . ?
C3 C2 C1 Br7 179.8(4) . . . . ?
C3 C2 C1 C6 0.2(7) . . . . ?
C3 C4 C5 F10 -179.5(5) . . . . ?
C3 C4 C5 C6 -0.8(8) . . . . ?
C5 C4 C3 Br8 -178.7(4) . . . . ?
C5 C4 C3 C2 0.9(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.171
_oxdiff_exptl_absorpt_empirical_full_min 0.658
####################################################################### 
# 
# 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_20161213a
_database_code_depnum_ccdc_archive 'CCDC 1547634'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        1BrPB-FA
_chemical_formula_moiety         'Br C6 F5, C16 H10'
_chemical_formula_sum            'C22 H10 Br F5'
_chemical_formula_weight         449.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1Br1
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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5813(6)
_cell_length_b                   7.9328(5)
_cell_length_c                   28.450(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1711.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1324
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      25.4370
_cell_measurement_theta_min      3.9350
_exptl_absorpt_coefficient_mu    2.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5387
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.44
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9937
_diffrn_measured_fraction_theta_max 0.7351
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  78.00   1.00    5.00    --   12.61  19.00  90.00   92
  2  ω    -10.00  39.00   1.00    5.00    --   12.61 -99.00-120.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0658050000
_diffrn_orient_matrix_UB_12      -0.0629663000
_diffrn_orient_matrix_UB_13      -0.0022521000
_diffrn_orient_matrix_UB_21      0.0347189000
_diffrn_orient_matrix_UB_22      -0.0230625000
_diffrn_orient_matrix_UB_23      -0.0222512000
_diffrn_orient_matrix_UB_31      0.0567409000
_diffrn_orient_matrix_UB_32      -0.0591333000
_diffrn_orient_matrix_UB_33      0.0110241000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2378
_reflns_number_total             2877
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C21(H21), C17(H17), C16(H16), C8(H8), C22(H22), C12(H12), C11(H11),
 C7(H7), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.49420(8) 0.29076(7) 0.68589(2) 0.03714(19) Uani 1 d . . .
F5 F 0.3367(4) -0.0427(4) 0.71806(10) 0.0355(9) Uani 1 d . . .
F3 F 0.4442(4) -0.3624(4) 0.58192(11) 0.0316(8) Uani 1 d . . .
F1 F 0.6355(4) 0.1995(4) 0.58919(11) 0.0343(8) Uani 1 d . . .
F4 F 0.3123(4) -0.3364(4) 0.67049(12) 0.0430(9) Uani 1 d . . .
F2 F 0.6065(4) -0.0939(5) 0.54199(10) 0.0363(9) Uani 1 d . . .
C2 C 0.5543(6) 0.0692(7) 0.60952(18) 0.0213(13) Uani 1 d . . .
C1 C 0.4852(8) 0.0851(6) 0.65430(17) 0.0222(11) Uani 1 d . . .
C19 C 0.5124(8) 0.4091(6) 0.35866(15) 0.0187(11) Uani 1 d . . .
C6 C 0.4042(7) -0.0528(7) 0.67438(17) 0.0233(13) Uani 1 d . . .
C20 C 0.5950(6) 0.3690(7) 0.40521(17) 0.0179(12) Uani 1 d . . .
C18 C 0.4837(6) 0.3221(6) 0.31804(16) 0.0236(11) Uani 1 d . . .
H18 H 0.5168 0.2097 0.3151 0.028 Uiso 1 calc . . R
C5 C 0.3917(6) -0.2026(8) 0.65087(19) 0.0249(12) Uani 1 d . . .
C10 C 0.4994(8) 0.6498(6) 0.40643(16) 0.0206(10) Uani 1 d . . .
C15 C 0.4593(6) 0.5786(6) 0.36193(17) 0.0197(12) Uani 1 d . . .
C4 C 0.4596(6) -0.2156(7) 0.60572(19) 0.0265(13) Uani 1 d . . .
C3 C 0.5396(6) -0.0797(7) 0.58589(18) 0.0246(13) Uani 1 d . . .
C21 C 0.6780(6) 0.2238(7) 0.42079(18) 0.0234(12) Uani 1 d . . .
H21 H 0.6835 0.1284 0.4019 0.028 Uiso 1 calc . . R
C9 C 0.5874(7) 0.5159(7) 0.43342(18) 0.0190(12) Uani 1 d . . .
C17 C 0.4009(7) 0.4096(8) 0.2801(2) 0.0296(14) Uani 1 d . . .
H17 H 0.3807 0.3527 0.2520 0.036 Uiso 1 calc . . R
C16 C 0.3506(7) 0.5745(8) 0.28376(19) 0.0290(14) Uani 1 d . . .
H16 H 0.2971 0.6270 0.2582 0.035 Uiso 1 calc . . R
C14 C 0.3782(6) 0.6666(7) 0.32551(18) 0.0241(13) Uani 1 d . . .
C8 C 0.6621(7) 0.5141(8) 0.47795(19) 0.0263(13) Uani 1 d . . .
H8 H 0.6575 0.6087 0.4972 0.032 Uiso 1 calc . . R
C22 C 0.7532(7) 0.2241(8) 0.46553(19) 0.0290(14) Uani 1 d . . .
H22 H 0.8093 0.1280 0.4768 0.035 Uiso 1 calc . . R
C12 C 0.3711(7) 0.9059(7) 0.3781(2) 0.0294(14) Uani 1 d . . .
H12 H 0.3409 1.0177 0.3836 0.035 Uiso 1 calc . . R
C11 C 0.4553(6) 0.8139(7) 0.4143(2) 0.0269(13) Uani 1 d . . .
H11 H 0.4802 0.8646 0.4430 0.032 Uiso 1 calc . . R
C7 C 0.7443(7) 0.3662(8) 0.49301(18) 0.0295(14) Uani 1 d . . .
H7 H 0.7949 0.3638 0.5228 0.035 Uiso 1 calc . . R
C13 C 0.3327(7) 0.8375(8) 0.3356(2) 0.0331(15) Uani 1 d . . .
H13 H 0.2762 0.9023 0.3129 0.040 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.864(5) . ?
F5 C6 1.346(6) . ?
F3 C4 1.352(6) . ?
F1 C2 1.335(6) . ?
F4 C5 1.341(6) . ?
F2 C3 1.353(6) . ?
C2 C1 1.384(7) . ?
C2 C3 1.364(7) . ?
C1 C6 1.379(7) . ?
C19 C20 1.499(7) . ?
C19 C18 1.363(6) . ?
C19 C15 1.407(7) . ?
C6 C5 1.367(8) . ?
C20 C21 1.385(7) . ?
C20 C9 1.416(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.429(7) . ?
C5 C4 1.388(7) . ?
C10 C15 1.420(7) . ?
C10 C9 1.471(7) . ?
C10 C11 1.362(7) . ?
C15 C14 1.393(7) . ?
C4 C3 1.359(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(7) . ?
C9 C8 1.388(7) . ?
C17 H17 0.9300 . ?
C17 C16 1.366(8) . ?
C16 H16 0.9300 . ?
C16 C14 1.410(8) . ?
C14 C13 1.428(8) . ?
C8 H8 0.9300 . ?
C8 C7 1.396(8) . ?
C22 H22 0.9300 . ?
C22 C7 1.374(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.414(8) . ?
C12 C13 1.356(8) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C2 C1 120.2(5) . . ?
F1 C2 C3 119.7(5) . . ?
C3 C2 C1 120.1(5) . . ?
C2 C1 Br1 120.7(4) . . ?
C6 C1 Br1 120.8(4) . . ?
C6 C1 C2 118.6(5) . . ?
C18 C19 C20 135.1(5) . . ?
C18 C19 C15 119.6(5) . . ?
C15 C19 C20 105.3(4) . . ?
F5 C6 C1 120.3(5) . . ?
F5 C6 C5 118.5(5) . . ?
C5 C6 C1 121.2(5) . . ?
C21 C20 C19 130.5(5) . . ?
C21 C20 C9 121.4(5) . . ?
C9 C20 C19 108.0(4) . . ?
C19 C18 H18 121.1 . . ?
C19 C18 C17 117.7(5) . . ?
C17 C18 H18 121.1 . . ?
F4 C5 C6 121.0(5) . . ?
F4 C5 C4 119.5(5) . . ?
C6 C5 C4 119.5(5) . . ?
C15 C10 C9 106.0(4) . . ?
C11 C10 C15 118.3(5) . . ?
C11 C10 C9 135.7(5) . . ?
C19 C15 C10 112.2(4) . . ?
C14 C15 C19 123.8(5) . . ?
C14 C15 C10 124.0(5) . . ?
F3 C4 C5 119.7(5) . . ?
F3 C4 C3 120.9(5) . . ?
C3 C4 C5 119.4(5) . . ?
F2 C3 C2 119.8(5) . . ?
F2 C3 C4 119.0(5) . . ?
C4 C3 C2 121.2(5) . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.4(5) . . ?
C22 C21 H21 120.8 . . ?
C20 C9 C10 108.5(4) . . ?
C8 C9 C20 119.5(5) . . ?
C8 C9 C10 132.0(5) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 C18 122.0(5) . . ?
C16 C17 H17 119.0 . . ?
C17 C16 H16 119.4 . . ?
C17 C16 C14 121.3(5) . . ?
C14 C16 H16 119.4 . . ?
C15 C14 C16 115.6(5) . . ?
C15 C14 C13 115.7(5) . . ?
C16 C14 C13 128.7(5) . . ?
C9 C8 H8 120.9 . . ?
C9 C8 C7 118.1(5) . . ?
C7 C8 H8 120.9 . . ?
C21 C22 H22 120.0 . . ?
C7 C22 C21 120.1(5) . . ?
C7 C22 H22 120.0 . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C13 C12 C11 122.6(5) . . ?
C10 C11 C12 119.0(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C8 C7 H7 118.8 . . ?
C22 C7 C8 122.5(5) . . ?
C22 C7 H7 118.8 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.5(6) . . ?
C12 C13 H13 119.8 . . ?

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 C6 F5 -2.8(7) . . . . ?
Br1 C1 C6 C5 177.8(4) . . . . ?
F5 C6 C5 F4 0.8(7) . . . . ?
F5 C6 C5 C4 179.7(4) . . . . ?
F3 C4 C3 F2 -1.0(7) . . . . ?
F3 C4 C3 C2 179.4(4) . . . . ?
F1 C2 C1 Br1 3.0(7) . . . . ?
F1 C2 C1 C6 -179.2(5) . . . . ?
F1 C2 C3 F2 -0.4(7) . . . . ?
F1 C2 C3 C4 179.2(4) . . . . ?
F4 C5 C4 F3 0.4(7) . . . . ?
F4 C5 C4 C3 179.8(5) . . . . ?
C2 C1 C6 F5 179.4(4) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C1 C2 C3 F2 179.5(4) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C1 C6 C5 F4 -179.8(5) . . . . ?
C1 C6 C5 C4 -0.9(8) . . . . ?
C19 C20 C21 C22 176.3(5) . . . . ?
C19 C20 C9 C10 0.7(6) . . . . ?
C19 C20 C9 C8 -177.4(4) . . . . ?
C19 C18 C17 C16 -0.3(8) . . . . ?
C19 C15 C14 C16 0.1(8) . . . . ?
C19 C15 C14 C13 179.5(5) . . . . ?
C6 C5 C4 F3 -178.6(4) . . . . ?
C6 C5 C4 C3 0.9(7) . . . . ?
C20 C19 C18 C17 -178.7(5) . . . . ?
C20 C19 C15 C10 -0.4(6) . . . . ?
C20 C19 C15 C14 179.0(4) . . . . ?
C20 C21 C22 C7 -0.2(7) . . . . ?
C20 C9 C8 C7 0.7(7) . . . . ?
C18 C19 C20 C21 3.1(10) . . . . ?
C18 C19 C20 C9 179.1(6) . . . . ?
C18 C19 C15 C10 -179.9(4) . . . . ?
C18 C19 C15 C14 -0.4(8) . . . . ?
C18 C17 C16 C14 0.0(8) . . . . ?
C5 C4 C3 F2 179.6(4) . . . . ?
C5 C4 C3 C2 0.0(8) . . . . ?
C10 C15 C14 C16 179.5(5) . . . . ?
C10 C15 C14 C13 -1.1(7) . . . . ?
C10 C9 C8 C7 -177.0(5) . . . . ?
C15 C19 C20 C21 -176.2(5) . . . . ?
C15 C19 C20 C9 -0.2(6) . . . . ?
C15 C19 C18 C17 0.5(7) . . . . ?
C15 C10 C9 C20 -1.0(6) . . . . ?
C15 C10 C9 C8 176.9(5) . . . . ?
C15 C10 C11 C12 0.3(8) . . . . ?
C15 C14 C13 C12 1.2(7) . . . . ?
C3 C2 C1 Br1 -176.9(4) . . . . ?
C3 C2 C1 C6 0.9(7) . . . . ?
C21 C20 C9 C10 177.2(4) . . . . ?
C21 C20 C9 C8 -1.0(7) . . . . ?
C21 C22 C7 C8 -0.1(8) . . . . ?
C9 C20 C21 C22 0.7(7) . . . . ?
C9 C10 C15 C19 0.9(6) . . . . ?
C9 C10 C15 C14 -178.5(5) . . . . ?
C9 C10 C11 C12 178.9(6) . . . . ?
C9 C8 C7 C22 -0.1(8) . . . . ?
C17 C16 C14 C15 0.1(7) . . . . ?
C17 C16 C14 C13 -179.2(5) . . . . ?
C16 C14 C13 C12 -179.5(5) . . . . ?
C11 C10 C15 C19 179.8(5) . . . . ?
C11 C10 C15 C14 0.4(8) . . . . ?
C11 C10 C9 C20 -179.6(6) . . . . ?
C11 C10 C9 C8 -1.8(11) . . . . ?
C11 C12 C13 C14 -0.5(8) . . . . ?
C13 C12 C11 C10 -0.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.750
####################################################################### 
# 
# 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_20161209a
_database_code_depnum_ccdc_archive 'CCDC 1547626'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        1ClPB-FA
_chemical_formula_moiety         'C6 Cl F5, C16 H10'
_chemical_formula_sum            'C22 H10 Cl F5'
_chemical_formula_weight         404.75
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1Cl1
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5282(2)
_cell_length_b                   7.8131(2)
_cell_length_c                   28.2918(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1664.08(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11252
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.9900
_cell_measurement_theta_min      3.7030
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            24501
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9951
_diffrn_measured_fraction_theta_max 0.8859
_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  45.00   1.00    3.00    --   12.76 -77.00  90.00   41
  2  ω    -14.00  81.00   1.00    3.00    --   12.76  77.00-180.00   95
  3  ω      3.00  53.00   1.00    3.00    --   12.45 -99.00 -60.00   50
  4  ω      9.00  39.00   1.00    3.00    --   12.45 -99.00  60.00   30
  5  ω      9.00  37.00   1.00    3.00    --   12.45 -37.00  30.00   28
  6  ω    -36.00   5.00   1.00    3.00    --   12.45 -37.00  30.00   41
  7  ω    -23.00  85.00   1.00    3.00    --   12.45  19.00 150.00  108
  8  ω    -19.00  89.00   1.00    3.00    --   12.45  77.00 -30.00  108
  9  ω     19.00  47.00   1.00    3.00    --   14.00 -77.00  28.48   28
 10  ω    -59.00  -4.00   1.00    3.00    --   14.00 -77.00  28.48   55
 11  ω    -34.00  50.00   1.00    3.00    --   14.00 -87.00-156.41   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0307452000
_diffrn_orient_matrix_UB_12      0.0610167000
_diffrn_orient_matrix_UB_13      0.0166514000
_diffrn_orient_matrix_UB_21      0.0232740000
_diffrn_orient_matrix_UB_22      -0.0671530000
_diffrn_orient_matrix_UB_23      0.0157021000
_diffrn_orient_matrix_UB_31      0.0859837000
_diffrn_orient_matrix_UB_32      -0.0036261000
_diffrn_orient_matrix_UB_33      -0.0102112000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2981
_reflns_number_total             3031
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.4476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0643
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C17(H17), C12(H12), C22(H22), C7(H7), C19(H19), C14(H14),
 C13(H13), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.50869(6) 0.27772(5) 0.313973(16) 0.02470(12) Uani 1 d . . .
F5 F 0.36801(13) 0.20906(12) 0.40906(4) 0.0229(2) Uani 1 d . . .
F4 F 0.39362(13) -0.08706(14) 0.45793(3) 0.0233(2) Uani 1 d . . .
F3 F 0.55533(14) -0.36298(13) 0.41835(4) 0.0264(3) Uani 1 d . . .
F1 F 0.66417(14) -0.04689(14) 0.28018(3) 0.0248(2) Uani 1 d . . .
F2 F 0.68727(14) -0.34300(13) 0.32917(4) 0.0271(3) Uani 1 d . . .
C4 C 0.5417(2) -0.2164(2) 0.39393(6) 0.0180(4) Uani 1 d . . .
C21 C 0.4138(2) 0.5148(2) 0.56699(6) 0.0139(3) Uani 1 d . . .
C2 C 0.5968(2) -0.0549(2) 0.32409(6) 0.0172(4) Uani 1 d . . .
C8 C 0.2451(2) 0.2202(2) 0.53545(6) 0.0199(4) Uani 1 d . . .
H8 H 0.1881 0.1224 0.5244 0.024 Uiso 1 calc . . R
C10 C 0.4049(2) 0.3668(2) 0.59604(6) 0.0140(3) Uani 1 d . . .
C6 C 0.4473(2) 0.0741(2) 0.38910(6) 0.0154(3) Uani 1 d . . .
C5 C 0.4596(2) -0.0768(2) 0.41404(6) 0.0167(4) Uani 1 d . . .
C3 C 0.6099(2) -0.2059(2) 0.34870(6) 0.0179(3) Uani 1 d . . .
C20 C 0.5035(2) 0.65185(19) 0.59395(6) 0.0146(3) Uani 1 d . . .
C15 C 0.6276(2) 0.6709(2) 0.67513(6) 0.0171(4) Uani 1 d . . .
C9 C 0.3205(2) 0.2204(2) 0.58030(6) 0.0165(3) Uani 1 d . . .
H9 H 0.3143 0.1236 0.5994 0.020 Uiso 1 calc . . R
C16 C 0.5442(2) 0.5814(2) 0.63866(6) 0.0146(3) Uani 1 d . . .
C11 C 0.4890(2) 0.4084(2) 0.64192(6) 0.0144(3) Uani 1 d . . .
C17 C 0.6726(2) 0.8443(2) 0.66506(6) 0.0208(4) Uani 1 d . . .
H17 H 0.7278 0.9107 0.6880 0.025 Uiso 1 calc . . R
C12 C 0.5202(2) 0.3218(2) 0.68327(6) 0.0171(3) Uani 1 d . . .
H12 H 0.4868 0.2078 0.6865 0.020 Uiso 1 calc . . R
C22 C 0.3383(2) 0.5134(2) 0.52214(6) 0.0180(4) Uani 1 d . . .
H22 H 0.3440 0.6095 0.5028 0.022 Uiso 1 calc . . R
C7 C 0.2538(2) 0.3645(2) 0.50695(6) 0.0207(4) Uani 1 d . . .
H7 H 0.2023 0.3618 0.4771 0.025 Uiso 1 calc . . R
C19 C 0.5497(2) 0.8193(2) 0.58512(6) 0.0187(4) Uani 1 d . . .
H19 H 0.5258 0.8695 0.5560 0.022 Uiso 1 calc . . R
C1 C 0.5174(2) 0.0874(2) 0.34394(6) 0.0165(3) Uani 1 d . . .
C14 C 0.6573(2) 0.5776(2) 0.71753(6) 0.0203(4) Uani 1 d . . .
H14 H 0.7127 0.6305 0.7430 0.024 Uiso 1 calc . . R
C13 C 0.6047(2) 0.4099(2) 0.72099(6) 0.0200(4) Uani 1 d . . .
H13 H 0.6251 0.3517 0.7491 0.024 Uiso 1 calc . . R
C18 C 0.6350(2) 0.9135(2) 0.62180(7) 0.0220(4) Uani 1 d . . .
H18 H 0.6664 1.0267 0.6161 0.026 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7128(16) . ?
F5 C6 1.3368(19) . ?
F4 C5 1.3397(19) . ?
F3 C4 1.341(2) . ?
F1 C2 1.3433(19) . ?
F2 C3 1.3383(19) . ?
C4 C5 1.377(2) . ?
C4 C3 1.382(2) . ?
C21 C10 1.421(2) . ?
C21 C20 1.478(2) . ?
C21 C22 1.390(2) . ?
C2 C3 1.374(3) . ?
C2 C1 1.381(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(2) . ?
C8 C7 1.388(3) . ?
C10 C9 1.382(2) . ?
C10 C11 1.480(2) . ?
C6 C5 1.377(2) . ?
C6 C1 1.387(2) . ?
C20 C16 1.413(2) . ?
C20 C19 1.376(2) . ?
C15 C16 1.396(2) . ?
C15 C17 1.425(2) . ?
C15 C14 1.421(2) . ?
C9 H9 0.9300 . ?
C16 C11 1.417(2) . ?
C11 C12 1.372(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.420(2) . ?
C22 H22 0.9300 . ?
C22 C7 1.394(3) . ?
C7 H7 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.425(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.373(3) . ?
C13 H13 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3 C4 C5 119.87(15) . . ?
F3 C4 C3 119.96(15) . . ?
C5 C4 C3 120.17(16) . . ?
C10 C21 C20 108.24(14) . . ?
C22 C21 C10 120.16(15) . . ?
C22 C21 C20 131.56(15) . . ?
F1 C2 C3 118.77(15) . . ?
F1 C2 C1 120.13(15) . . ?
C3 C2 C1 121.10(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.69(17) . . ?
C21 C10 C11 107.95(14) . . ?
C9 C10 C21 120.62(15) . . ?
C9 C10 C11 131.36(15) . . ?
F5 C6 C5 119.28(15) . . ?
F5 C6 C1 120.01(15) . . ?
C5 C6 C1 120.72(15) . . ?
F4 C5 C4 120.12(15) . . ?
F4 C5 C6 120.07(15) . . ?
C4 C5 C6 119.80(15) . . ?
F2 C3 C4 119.77(16) . . ?
F2 C3 C2 120.64(15) . . ?
C2 C3 C4 119.58(16) . . ?
C16 C20 C21 106.19(14) . . ?
C19 C20 C21 135.25(16) . . ?
C19 C20 C16 118.56(16) . . ?
C16 C15 C17 115.82(16) . . ?
C16 C15 C14 115.95(16) . . ?
C14 C15 C17 128.23(17) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.83(16) . . ?
C10 C9 H9 120.6 . . ?
C20 C16 C11 111.49(14) . . ?
C15 C16 C20 124.32(16) . . ?
C15 C16 C11 124.19(16) . . ?
C16 C11 C10 106.14(14) . . ?
C12 C11 C10 135.46(15) . . ?
C12 C11 C16 118.40(15) . . ?
C15 C17 H17 119.8 . . ?
C18 C17 C15 120.36(17) . . ?
C18 C17 H17 119.8 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.60(15) . . ?
C13 C12 H12 120.7 . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C7 118.31(16) . . ?
C7 C22 H22 120.8 . . ?
C8 C7 C22 121.38(16) . . ?
C8 C7 H7 119.3 . . ?
C22 C7 H7 119.3 . . ?
C20 C19 H19 120.9 . . ?
C20 C19 C18 118.20(16) . . ?
C18 C19 H19 120.9 . . ?
C2 C1 Cl1 120.93(13) . . ?
C2 C1 C6 118.62(15) . . ?
C6 C1 Cl1 120.45(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.29(16) . . ?
C13 C14 H14 119.9 . . ?
C12 C13 H13 118.7 . . ?
C14 C13 C12 122.58(16) . . ?
C14 C13 H13 118.7 . . ?
C17 C18 C19 122.72(16) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?

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
F5 C6 C5 F4 -0.4(2) . . . . ?
F5 C6 C5 C4 -179.70(14) . . . . ?
F5 C6 C1 Cl1 1.8(2) . . . . ?
F5 C6 C1 C2 -179.30(14) . . . . ?
F3 C4 C5 F4 0.1(2) . . . . ?
F3 C4 C5 C6 179.32(14) . . . . ?
F3 C4 C3 F2 0.9(2) . . . . ?
F3 C4 C3 C2 -179.40(15) . . . . ?
F1 C2 C3 F2 -0.5(2) . . . . ?
F1 C2 C3 C4 179.88(14) . . . . ?
F1 C2 C1 Cl1 -1.9(2) . . . . ?
F1 C2 C1 C6 179.20(14) . . . . ?
C21 C10 C9 C8 0.2(2) . . . . ?
C21 C10 C11 C16 0.43(17) . . . . ?
C21 C10 C11 C12 179.89(18) . . . . ?
C21 C20 C16 C15 -178.97(15) . . . . ?
C21 C20 C16 C11 0.79(18) . . . . ?
C21 C20 C19 C18 178.81(17) . . . . ?
C21 C22 C7 C8 -0.2(2) . . . . ?
C10 C21 C20 C16 -0.50(18) . . . . ?
C10 C21 C20 C19 -179.88(17) . . . . ?
C10 C21 C22 C7 0.4(2) . . . . ?
C10 C11 C12 C13 -178.77(17) . . . . ?
C5 C4 C3 F2 -179.07(14) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C5 C6 C1 Cl1 -177.65(13) . . . . ?
C5 C6 C1 C2 1.3(2) . . . . ?
C3 C4 C5 F4 -179.92(14) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C3 C2 C1 Cl1 177.56(13) . . . . ?
C3 C2 C1 C6 -1.4(2) . . . . ?
C20 C21 C10 C9 177.35(14) . . . . ?
C20 C21 C10 C11 0.04(18) . . . . ?
C20 C21 C22 C7 -176.73(16) . . . . ?
C20 C16 C11 C10 -0.77(18) . . . . ?
C20 C16 C11 C12 179.66(15) . . . . ?
C20 C19 C18 C17 0.1(2) . . . . ?
C15 C16 C11 C10 178.99(15) . . . . ?
C15 C16 C11 C12 -0.6(2) . . . . ?
C15 C17 C18 C19 0.4(3) . . . . ?
C15 C14 C13 C12 0.3(3) . . . . ?
C9 C8 C7 C22 0.1(3) . . . . ?
C9 C10 C11 C16 -176.49(16) . . . . ?
C9 C10 C11 C12 3.0(3) . . . . ?
C16 C20 C19 C18 -0.5(2) . . . . ?
C16 C15 C17 C18 -0.4(2) . . . . ?
C16 C15 C14 C13 -0.2(2) . . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
C11 C10 C9 C8 176.82(16) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C17 C15 C16 C20 -0.1(2) . . . . ?
C17 C15 C16 C11 -179.82(15) . . . . ?
C17 C15 C14 C13 180.00(16) . . . . ?
C22 C21 C10 C9 -0.4(2) . . . . ?
C22 C21 C10 C11 -177.67(14) . . . . ?
C22 C21 C20 C16 176.86(17) . . . . ?
C22 C21 C20 C19 -2.5(3) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C19 C20 C16 C15 0.5(2) . . . . ?
C19 C20 C16 C11 -179.70(14) . . . . ?
C1 C2 C3 F2 -179.90(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C6 C5 F4 178.97(14) . . . . ?
C1 C6 C5 C4 -0.3(2) . . . . ?
C14 C15 C16 C20 -179.95(15) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C14 C15 C17 C18 179.48(16) . . . . ?

_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 5.032
_oxdiff_exptl_absorpt_empirical_full_min 0.672
