# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_20170301a
_database_code_depnum_ccdc_archive 'CCDC 1586063'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F3 I3, C16 H10'
_chemical_formula_sum            'C22 H10 F3 I3'
_chemical_formula_weight         712.00
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.12210(10)
_cell_length_b                   17.6080(2)
_cell_length_c                   22.7903(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2055.46(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3958
_cell_measurement_temperature    285(1)
_cell_measurement_theta_max      73.2590
_cell_measurement_theta_min      5.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    36.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15693
_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    2.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7069
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.507
_diffrn_reflns_theta_min         3.879
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      285(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  31.00   1.00    1.08    --  -41.49  37.00-120.00   89
  2  ω     12.00  81.00   1.00    1.08    --   41.49 -99.00  90.00   69
  3  ω     73.00  98.00   1.00    1.08    --   41.49-125.00   0.00   25
  4  ω     36.00 108.00   1.00    4.33    --  107.52 -94.00 120.00   72
  5  ω     24.00  62.00   1.00    1.08    --   41.49-125.00   0.00   38
  6  ω     37.00 134.00   1.00    4.33    --  107.52 -61.00-120.00   97
  7  ω     91.00 135.00   1.00    4.33    --  107.52 -77.00 -60.00   44
  8  ω     84.00 171.00   1.00    4.33    --  107.52  61.00  30.00   87
  9  ω    112.00 147.00   1.00    4.33    --  107.52 103.00  85.00   35
 10  ω    128.00 177.00   1.00    4.33    --  107.52  77.00-150.00   49
 11  ω     87.00 112.00   1.00    4.33    --  107.52  77.00-150.00   25
 12  ω     30.00  55.00   1.00    1.08    --   41.49-125.00-180.00   25
;
_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      0.1539995000
_diffrn_orient_matrix_UB_12      -0.0693210000
_diffrn_orient_matrix_UB_13      0.0224445000
_diffrn_orient_matrix_UB_21      -0.1027401000
_diffrn_orient_matrix_UB_22      -0.0473916000
_diffrn_orient_matrix_UB_23      -0.0519559000
_diffrn_orient_matrix_UB_31      0.2369673000
_diffrn_orient_matrix_UB_32      0.0245084000
_diffrn_orient_matrix_UB_33      -0.0370090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1862
_reflns_number_total             2051
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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         1.390
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.253
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.072
_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)+(0.0863P)²+5.1285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1425
_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:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5000 0.6743(5) 0.7500 0.0388(19) Uani 1 2 d S T P . .
C2 C 0.6698(12) 0.7155(3) 0.7150(3) 0.0356(12) Uani 1 1 d . . . . .
C3 C 0.6692(11) 0.7936(3) 0.7131(2) 0.0290(11) Uani 1 1 d . . . . .
C4 C 0.5000 0.8320(4) 0.7500 0.0283(15) Uani 1 2 d S T P . .
F1 F 0.5000 0.9073(3) 0.7500 0.0447(12) Uani 1 2 d S T P . .
F2 F 0.8409(10) 0.6779(3) 0.6818(2) 0.0598(12) Uani 1 1 d . . . . .
I1 I 0.5000 0.55668(4) 0.7500 0.0827(4) Uani 1 2 d S T P . .
I2 I 0.91626(8) 0.85240(3) 0.65598(2) 0.0437(2) Uani 1 1 d . . . . .
C5 C 0.1689(14) 0.4099(5) 0.5449(3) 0.0499(17) Uani 1 1 d . . . . .
H5 H 0.0625 0.3689 0.5545 0.060 Uiso 1 1 calc R . . . .
C6 C 0.1391(13) 0.4753(5) 0.5740(3) 0.0502(19) Uani 1 1 d . . . . .
H6 H 0.0151 0.4784 0.6037 0.060 Uiso 1 1 calc R . . . .
C7 C 0.2946(12) 0.5408(4) 0.5603(2) 0.0397(14) Uani 1 1 d . . . . .
C8 C 0.2615(16) 0.6101(5) 0.5882(3) 0.060(2) Uani 1 1 d . . . . .
H8 H 0.1353 0.6149 0.6173 0.072 Uiso 1 1 calc R . . . .
C9 C 0.413(2) 0.6721(6) 0.5735(4) 0.067(3) Uani 1 1 d . . . . .
H9 H 0.3860 0.7180 0.5928 0.080 Uiso 1 1 calc R . . . .
C10 C 0.5996(19) 0.6675(5) 0.5313(4) 0.060(2) Uani 1 1 d . . . . .
H10 H 0.7017 0.7097 0.5225 0.072 Uiso 1 1 calc R . . . .
C11 C 0.6385(13) 0.5990(4) 0.5009(3) 0.0392(13) Uani 1 1 d . . . . .
C12 C 0.4850(11) 0.5352(4) 0.5151(2) 0.0299(11) 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 1.386(8) 3_656 ?
C1 C2 1.386(8) . ?
C1 I1 2.071(9) . ?
C2 C3 1.375(8) . ?
C2 F2 1.334(7) . ?
C3 C4 1.384(7) . ?
C3 I2 2.090(5) . ?
C4 C3 1.383(7) 3_656 ?
C4 F1 1.326(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.338(12) . ?
C5 C11 1.446(10) 5_666 ?
C6 H6 0.9300 . ?
C6 C7 1.435(11) . ?
C7 C8 1.387(11) . ?
C7 C12 1.423(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.360(15) . ?
C10 H10 0.9300 . ?
C10 C11 1.405(11) . ?
C11 C5 1.446(10) 5_666 ?
C11 C12 1.409(9) . ?
C12 C12 1.425(12) 5_666 ?

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 116.8(8) 3_656 . ?
C2 C1 I1 121.6(4) . . ?
C2 C1 I1 121.6(4) 3_656 . ?
C3 C2 C1 122.7(6) . . ?
F2 C2 C1 118.6(6) . . ?
F2 C2 C3 118.7(6) . . ?
C2 C3 C4 118.1(5) . . ?
C2 C3 I2 120.8(4) . . ?
C4 C3 I2 121.0(4) . . ?
C3 C4 C3 121.5(7) 3_656 . ?
F1 C4 C3 119.3(4) . . ?
F1 C4 C3 119.3(4) . 3_656 ?
C6 C5 H5 119.0 . . ?
C6 C5 C11 121.9(7) . 5_666 ?
C11 C5 H5 119.0 5_666 . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(6) . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 122.7(6) . . ?
C8 C7 C12 118.5(7) . . ?
C12 C7 C6 118.8(6) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.1(7) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(9) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(9) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C5 123.0(7) . 5_666 ?
C10 C11 C12 119.6(7) . . ?
C12 C11 C5 117.4(6) . 5_666 ?
C7 C12 C12 119.0(7) . 5_666 ?
C11 C12 C7 119.5(6) . . ?
C11 C12 C12 121.5(7) . 5_666 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.268
_oxdiff_exptl_absorpt_empirical_full_min 0.516
####################################################################### 
# 
# 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_20170607b
_database_code_depnum_ccdc_archive 'CCDC 1586064'
_audit_update_record             
;
2018-01-02 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        Pyr-TBrPB
_chemical_formula_moiety         'Br3 C6 F3, C16 H10'
_chemical_formula_sum            'C22 H10 Br3 F3'
_chemical_formula_weight         571.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1Br1
_chemical_oxdiff_usercomment     LB-41
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8395(3)
_cell_length_b                   14.7083(4)
_cell_length_c                   17.2969(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.132(3)
_cell_angle_gamma                90
_cell_volume                     1949.89(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4306
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7270
_cell_measurement_theta_min      5.7490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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 orange'
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.3
_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  0.0222
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7388
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.003
_diffrn_reflns_theta_min         3.983
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  70.00   1.00    1.00    --   41.49-125.00-120.00   40
  2  ω     25.00  56.00   1.00    1.00    --   41.49-125.00 -60.00   31
  3  ω     83.00 109.00   1.00    1.70    --  107.52 -94.00 -60.00   26
  4  ω     40.00 108.00   1.00    1.70    --  107.52 -94.00-120.00   68
  5  ω     35.00 124.00   1.00    1.70    --  107.52 -45.00-150.00   89
  6  ω     82.00 172.00   1.00    1.70    --  107.52  30.00  30.00   90
  7  ω    102.00 131.00   1.00    1.70    --  107.52 125.00 -60.00   29
  8  ω    106.00 146.00   1.00    1.70    --  107.52 125.00 -30.00   40
  9  ω     25.00  99.00   1.00    1.70    --  107.52 -94.00-180.00   74
 10  ω   -122.00  47.00   1.00    1.00    --  -41.49   0.00 120.00  169
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1729247000
_diffrn_orient_matrix_UB_12      -0.0519385000
_diffrn_orient_matrix_UB_13      -0.0059009000
_diffrn_orient_matrix_UB_21      -0.0111449000
_diffrn_orient_matrix_UB_22      0.0338150000
_diffrn_orient_matrix_UB_23      0.0831096000
_diffrn_orient_matrix_UB_31      -0.1017440000
_diffrn_orient_matrix_UB_32      0.0844569000
_diffrn_orient_matrix_UB_33      -0.0368619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3277
_reflns_number_total             3820
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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         1.560
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0824
_refine_ls_restrained_S_all      1.103
_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)+(0.1268P)²+9.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2438
_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(C20) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22),
 C18(H18), C19(H19)
3.b Fitted hexagon refined as free rotating group:
 C7(C8,C9,C10,C11,C12), C15(C16,C17,C20,C21,C22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.00649(15) 0.66684(9) 0.59441(5) 0.0856(5) Uani 1 1 d . . . . .
Br2 Br 0.73872(13) 0.55167(7) 0.28217(6) 0.0759(4) Uani 1 1 d . . . . .
Br3 Br 1.05910(14) 0.89521(7) 0.33620(9) 0.0939(5) Uani 1 1 d . . . . .
F1 F 0.8272(7) 0.5484(3) 0.4595(3) 0.0725(13) Uani 1 1 d . . . . .
F2 F 0.8730(8) 0.7370(4) 0.2473(3) 0.0818(16) Uani 1 1 d . . . . .
F3 F 1.1005(8) 0.8315(4) 0.5074(4) 0.0867(17) Uani 1 1 d . . . . .
C1 C 0.9642(9) 0.6902(5) 0.4852(4) 0.0520(16) Uani 1 1 d . U . . .
C2 C 0.8815(9) 0.6275(5) 0.4328(4) 0.0494(15) Uani 1 1 d . U . . .
C3 C 0.8489(9) 0.6412(5) 0.3522(4) 0.0478(14) Uani 1 1 d . U . . .
C4 C 0.9020(9) 0.7219(5) 0.3252(4) 0.0527(16) Uani 1 1 d . U . . .
C5 C 0.9859(9) 0.7870(5) 0.3756(5) 0.0542(16) Uani 1 1 d . U . . .
C6 C 1.0178(10) 0.7700(5) 0.4569(5) 0.0564(17) Uani 1 1 d . U . . .
C7 C 0.7040(12) 0.4310(4) 0.6179(6) 0.129(5) Uani 1 1 d . U . . .
H7 H 0.7308 0.4799 0.5884 0.155 Uiso 1 1 calc R . . . .
C8 C 0.7559(12) 0.4320(5) 0.6998(6) 0.114(4) Uani 1 1 d G U . . .
H8 H 0.8174 0.4814 0.7252 0.136 Uiso 1 1 calc R . . . .
C9 C 0.7159(12) 0.3590(6) 0.7439(4) 0.128(5) Uani 1 1 d G U . . .
H9 H 0.7506 0.3596 0.7987 0.153 Uiso 1 1 calc R . . . .
C10 C 0.6240(10) 0.2851(5) 0.7060(4) 0.088(3) Uani 1 1 d G U . . .
C11 C 0.5720(7) 0.2841(4) 0.6241(4) 0.0555(17) Uani 1 1 d G U . . .
C12 C 0.6120(10) 0.3571(5) 0.5800(3) 0.088(3) Uani 1 1 d G U . . .
C13 C 0.5513(14) 0.3526(8) 0.4908(6) 0.080(3) Uani 1 1 d . U . . .
H13 H 0.5705 0.4003 0.4584 0.096 Uiso 1 1 calc R . . . .
C14 C 0.471(2) 0.2787(11) 0.4617(10) 0.117(4) Uani 1 1 d . U . . .
H14 H 0.4375 0.2756 0.4069 0.141 Uiso 1 1 calc R . . . .
C15 C 0.4322(11) 0.2098(5) 0.5000(4) 0.095(3) Uani 1 1 d . U . . .
C16 C 0.4800(8) 0.2113(4) 0.5820(4) 0.0563(17) Uani 1 1 d G U . . .
C17 C 0.4387(11) 0.1383(6) 0.6258(4) 0.097(3) Uani 1 1 d G U . . .
C20 C 0.3496(14) 0.0639(5) 0.5874(7) 0.154(7) Uani 1 1 d G U . . .
H20 H 0.3219 0.0151 0.6167 0.185 Uiso 1 1 calc R . . . .
C21 C 0.3017(14) 0.0624(6) 0.5054(7) 0.143(6) Uani 1 1 d G U . . .
H21 H 0.2421 0.0126 0.4797 0.171 Uiso 1 1 calc R . . . .
C22 C 0.3431(13) 0.1354(7) 0.4616(4) 0.119(4) Uani 1 1 d G U . . .
H22 H 0.3111 0.1344 0.4067 0.143 Uiso 1 1 calc R . . . .
C18 C 0.4999(15) 0.1470(8) 0.7172(7) 0.090(3) Uani 1 1 d . U . . .
H18 H 0.4801 0.1003 0.7505 0.108 Uiso 1 1 calc R . . . .
C19 C 0.574(2) 0.2161(12) 0.7439(10) 0.118(4) Uani 1 1 d . U . . .
H19 H 0.5982 0.2208 0.7987 0.142 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 1.880(7) . ?
Br2 C3 1.873(7) . ?
Br3 C5 1.868(7) . ?
F1 C2 1.353(8) . ?
F2 C4 1.337(8) . ?
F3 C6 1.329(9) . ?
C1 C2 1.358(10) . ?
C1 C6 1.372(11) . ?
C2 C3 1.377(10) . ?
C3 C4 1.373(11) . ?
C4 C5 1.367(11) . ?
C5 C6 1.399(11) . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 C19 1.312(18) . ?
C11 C12 1.3900 . ?
C11 C16 1.406(8) . ?
C12 C13 1.519(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.305(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.280(17) . ?
C15 C16 1.3900 . ?
C15 C22 1.3900 . ?
C16 C17 1.3900 . ?
C17 C20 1.3900 . ?
C17 C18 1.559(14) . ?
C20 H20 0.9300 . ?
C20 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C22 1.3900 . ?
C22 H22 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.211(19) . ?
C19 H19 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 120.4(6) . . ?
C2 C1 C6 118.8(7) . . ?
C6 C1 Br1 120.8(6) . . ?
F1 C2 C1 119.7(7) . . ?
F1 C2 C3 117.8(7) . . ?
C1 C2 C3 122.5(7) . . ?
C2 C3 Br2 121.0(5) . . ?
C4 C3 Br2 121.3(5) . . ?
C4 C3 C2 117.8(7) . . ?
F2 C4 C3 119.2(7) . . ?
F2 C4 C5 118.9(7) . . ?
C5 C4 C3 121.9(7) . . ?
C4 C5 Br3 120.5(6) . . ?
C4 C5 C6 118.4(7) . . ?
C6 C5 Br3 121.0(6) . . ?
F3 C6 C1 119.5(7) . . ?
F3 C6 C5 119.9(7) . . ?
C1 C6 C5 120.6(7) . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C12 120.0 . . ?
C12 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C19 C10 C9 123.4(9) . . ?
C19 C10 C11 116.5(9) . . ?
C10 C11 C16 122.9(5) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 C16 117.1(5) . . ?
C7 C12 C13 122.3(6) . . ?
C11 C12 C7 120.0 . . ?
C11 C12 C13 117.7(6) . . ?
C12 C13 H13 121.6 . . ?
C14 C13 C12 116.8(11) . . ?
C14 C13 H13 121.6 . . ?
C13 C14 H14 116.3 . . ?
C15 C14 C13 127.4(14) . . ?
C15 C14 H14 116.3 . . ?
C14 C15 C16 118.3(10) . . ?
C14 C15 C22 121.7(10) . . ?
C16 C15 C22 120.0 . . ?
C15 C16 C11 122.6(6) . . ?
C15 C16 C17 120.0 . . ?
C17 C16 C11 117.4(6) . . ?
C16 C17 C18 115.6(7) . . ?
C20 C17 C16 120.0 . . ?
C20 C17 C18 124.4(7) . . ?
C17 C20 H20 120.0 . . ?
C21 C20 C17 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C15 C22 H22 120.0 . . ?
C21 C22 C15 120.0 . . ?
C21 C22 H22 120.0 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.4(12) . . ?
C19 C18 H18 120.8 . . ?
C10 C19 H19 115.6 . . ?
C18 C19 C10 128.9(15) . . ?
C18 C19 H19 115.6 . . ?

_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 0.689
####################################################################### 
# 
# 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_20170713b
_database_code_depnum_ccdc_archive 'CCDC 1586066'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br3 C6 F3, C14 H10'
_chemical_formula_sum            'C20 H10 Br3 F3'
_chemical_formula_weight         547.01
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.95830(10)
_cell_length_b                   14.36850(10)
_cell_length_c                   11.38620(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.8850(10)
_cell_angle_gamma                90
_cell_volume                     1771.29(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8744
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2690
_cell_measurement_theta_min      4.0820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12059
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.422
_diffrn_reflns_theta_min         4.993
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  24.00   1.00    1.00    --  -41.49  57.00 -60.00   54
  2  ω     36.00 115.00   1.00    1.00    --   41.49  37.00-120.00   79
  3  ω     81.00 111.00   1.00    1.00    --  107.52  61.00-180.00   30
  4  ω    145.00 178.00   1.00    1.00    --  107.52  61.00-180.00   33
  5  ω    139.00 165.00   1.00    1.00    --  107.52  77.00 -30.00   26
  6  ω    144.00 174.00   1.00    1.00    --  107.52 125.00  30.00   30
  7  ω    100.00 178.00   1.00    1.00    --  107.52  45.00 -60.00   78
  8  ω     78.00 113.00   1.00    1.00    --  107.52  77.00 -30.00   35
  9  ω     44.00 178.00   1.00    1.00    --  107.52   0.00  90.00  134
 10  ω     92.00 118.00   1.00    1.00    --  107.52-125.00 -60.00   26
 11  ω     39.00  90.00   1.00    1.00    --   41.49-125.00 -60.00   51
 12  ω     41.00 136.00   1.00    1.00    --  107.52 -61.00 -30.00   95
 13  ω     75.00 118.00   1.00    1.00    --  107.52-125.00 150.00   43
 14  ω     39.00  66.00   1.00    1.00    --  107.52-125.00 150.00   27
 15  ω     31.00 117.00   1.00    1.00    --  107.52 -77.00 120.00   86
 16  ω     25.00 108.00   1.00    1.00    --  107.52 -94.00 -30.00   83
 17  ω     34.00 106.00   1.00    1.00    --  107.52 -45.00-180.00   72
 18  ω    -67.00  32.00   1.00    1.00    --  -41.49  57.00 150.00   99
 19  ω   -107.00 -17.00   1.00    1.00    --  -41.49 -57.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1070949000
_diffrn_orient_matrix_UB_12      0.0683133000
_diffrn_orient_matrix_UB_13      0.0067025000
_diffrn_orient_matrix_UB_21      -0.0560735000
_diffrn_orient_matrix_UB_22      -0.0249476000
_diffrn_orient_matrix_UB_23      -0.1286384000
_diffrn_orient_matrix_UB_31      -0.0748824000
_diffrn_orient_matrix_UB_32      -0.0788307000
_diffrn_orient_matrix_UB_33      0.0466009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3360
_reflns_number_total             3517
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    ?
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.087
_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)+(0.0203P)²+0.9160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0428
_refine_ls_wR_factor_ref         0.0435
_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:
 C19(H19), C10(H10), C18(H18), C16(H16), C7(H7), C9(H9), C8(H8), C13(H13),
 C15(H15), C14(H14)
;
_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
Br3 Br 0.27304(2) 0.28283(2) 0.44304(2) 0.01746(6) Uani 1 1 d . . . . .
Br2 Br 0.39868(2) 0.00241(2) 0.13372(2) 0.01965(6) Uani 1 1 d . . . . .
Br1 Br 0.49889(2) 0.38074(2) 0.04497(2) 0.01869(6) Uani 1 1 d . . . . .
F3 F 0.37622(10) 0.40452(7) 0.26348(10) 0.0190(2) Uani 1 1 d . . . . .
F1 F 0.48919(10) 0.17123(8) 0.01252(9) 0.0187(2) Uani 1 1 d . . . . .
F2 F 0.30621(10) 0.09043(8) 0.34542(10) 0.0192(2) Uani 1 1 d . . . . .
C6 C 0.38357(16) 0.31439(12) 0.23625(16) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.39976(16) 0.75818(13) 0.45541(16) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.43974(16) 0.19626(13) 0.10834(16) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.34754(16) 0.15524(12) 0.27687(15) 0.0135(3) Uani 1 1 d . . . . .
C19 C 0.34191(17) 0.63057(13) 0.58096(17) 0.0172(4) Uani 1 1 d . . . . .
H19 H 0.3357 0.5671 0.5949 0.021 Uiso 1 1 calc R . . . .
C10 C 0.44756(16) 0.78605(13) 0.35224(16) 0.0159(4) Uani 1 1 d . . . . .
H10 H 0.4544 0.8491 0.3360 0.019 Uiso 1 1 calc R . . . .
C17 C 0.31459(16) 0.78997(13) 0.64056(16) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.34058(16) 0.24803(13) 0.30780(16) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.39570(16) 0.12792(12) 0.17695(16) 0.0136(3) Uani 1 1 d . . . . .
C18 C 0.30530(17) 0.69156(14) 0.65824(16) 0.0177(4) Uani 1 1 d . . . . .
H18 H 0.2735 0.6695 0.7241 0.021 Uiso 1 1 calc R . . . .
C20 C 0.39044(16) 0.66142(13) 0.47735(16) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.43441(16) 0.28974(12) 0.13651(16) 0.0133(3) Uani 1 1 d . . . . .
C12 C 0.36039(16) 0.82413(12) 0.53897(16) 0.0131(3) Uani 1 1 d . . . . .
C16 C 0.27912(17) 0.85383(15) 0.72365(17) 0.0198(4) Uani 1 1 d . . . . .
H16 H 0.2503 0.8316 0.7910 0.024 Uiso 1 1 calc R . . . .
C7 C 0.42828(17) 0.59675(13) 0.39721(17) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.4220 0.5334 0.4117 0.021 Uiso 1 1 calc R . . . .
C9 C 0.48401(17) 0.72128(14) 0.27560(16) 0.0190(4) Uani 1 1 d . . . . .
H9 H 0.5153 0.7410 0.2084 0.023 Uiso 1 1 calc R . . . .
C8 C 0.47436(17) 0.62604(14) 0.29784(17) 0.0192(4) Uani 1 1 d . . . . .
H8 H 0.4990 0.5827 0.2456 0.023 Uiso 1 1 calc R . . . .
C13 C 0.36641(17) 0.92147(13) 0.52344(18) 0.0188(4) Uani 1 1 d . . . . .
H13 H 0.3955 0.9451 0.4569 0.023 Uiso 1 1 calc R . . . .
C15 C 0.28664(18) 0.94801(15) 0.70643(19) 0.0238(4) Uani 1 1 d . . . . .
H15 H 0.2631 0.9893 0.7618 0.029 Uiso 1 1 calc R . . . .
C14 C 0.33005(19) 0.98176(14) 0.60498(19) 0.0234(4) Uani 1 1 d . . . . .
H14 H 0.3343 1.0456 0.5928 0.028 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
Br3 C5 1.8765(17) . ?
Br2 C3 1.8709(17) . ?
Br1 C1 1.8769(17) . ?
F3 C6 1.337(2) . ?
F1 C2 1.340(2) . ?
F2 C4 1.338(2) . ?
C6 C5 1.383(3) . ?
C6 C1 1.386(2) . ?
C11 C10 1.416(2) . ?
C11 C20 1.419(3) . ?
C11 C12 1.455(2) . ?
C2 C3 1.387(2) . ?
C2 C1 1.384(2) . ?
C4 C5 1.384(3) . ?
C4 C3 1.383(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.346(3) . ?
C19 C20 1.437(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(3) . ?
C17 C18 1.434(3) . ?
C17 C12 1.418(2) . ?
C17 C16 1.415(3) . ?
C18 H18 0.9300 . ?
C20 C7 1.409(3) . ?
C12 C13 1.412(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.372(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.399(3) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.373(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.402(3) . ?
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
F3 C6 C5 119.53(16) . . ?
F3 C6 C1 118.94(16) . . ?
C5 C6 C1 121.53(16) . . ?
C10 C11 C20 117.98(16) . . ?
C10 C11 C12 122.91(17) . . ?
C20 C11 C12 119.11(16) . . ?
F1 C2 C3 119.22(16) . . ?
F1 C2 C1 119.07(16) . . ?
C1 C2 C3 121.71(16) . . ?
F2 C4 C5 119.02(16) . . ?
F2 C4 C3 119.26(16) . . ?
C3 C4 C5 121.72(16) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.41(17) . . ?
C20 C19 H19 119.3 . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 121.03(17) . . ?
C9 C10 H10 119.5 . . ?
C12 C17 C18 119.84(17) . . ?
C16 C17 C18 120.85(17) . . ?
C16 C17 C12 119.30(17) . . ?
C6 C5 Br3 120.87(14) . . ?
C6 C5 C4 118.49(16) . . ?
C4 C5 Br3 120.64(14) . . ?
C2 C3 Br2 120.83(13) . . ?
C4 C3 Br2 120.96(13) . . ?
C4 C3 C2 118.20(16) . . ?
C19 C18 C17 121.02(17) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C11 C20 C19 119.51(16) . . ?
C7 C20 C11 119.72(17) . . ?
C7 C20 C19 120.76(17) . . ?
C6 C1 Br1 120.69(13) . . ?
C2 C1 Br1 120.95(13) . . ?
C2 C1 C6 118.33(16) . . ?
C17 C12 C11 119.09(16) . . ?
C13 C12 C11 122.60(17) . . ?
C13 C12 C17 118.31(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.03(18) . . ?
C15 C16 H16 119.5 . . ?
C20 C7 H7 119.5 . . ?
C8 C7 C20 120.90(18) . . ?
C8 C7 H7 119.5 . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.61(18) . . ?
C8 C9 H9 119.7 . . ?
C7 C8 C9 119.76(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.06(18) . . ?
C14 C13 H13 119.5 . . ?
C16 C15 H15 120.2 . . ?
C16 C15 C14 119.64(18) . . ?
C14 C15 H15 120.2 . . ?
C13 C14 C15 120.64(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?

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
F3 C6 C5 Br3 -0.4(2) . . . . ?
F3 C6 C5 C4 179.09(15) . . . . ?
F3 C6 C1 Br1 2.9(2) . . . . ?
F3 C6 C1 C2 -179.03(15) . . . . ?
F1 C2 C3 Br2 -2.5(2) . . . . ?
F1 C2 C3 C4 178.60(15) . . . . ?
F1 C2 C1 Br1 -1.6(2) . . . . ?
F1 C2 C1 C6 -179.67(15) . . . . ?
F2 C4 C5 Br3 -0.5(2) . . . . ?
F2 C4 C5 C6 -179.99(15) . . . . ?
F2 C4 C3 Br2 2.1(2) . . . . ?
F2 C4 C3 C2 -179.00(15) . . . . ?
C11 C10 C9 C8 0.1(3) . . . . ?
C11 C20 C7 C8 0.1(3) . . . . ?
C11 C12 C13 C14 -179.08(18) . . . . ?
C19 C20 C7 C8 179.79(17) . . . . ?
C10 C11 C20 C19 -179.76(16) . . . . ?
C10 C11 C20 C7 0.0(3) . . . . ?
C10 C11 C12 C17 -179.48(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C10 C9 C8 C7 -0.1(3) . . . . ?
C17 C12 C13 C14 0.6(3) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
C5 C6 C1 Br1 -177.10(13) . . . . ?
C5 C6 C1 C2 1.0(3) . . . . ?
C5 C4 C3 Br2 -177.66(13) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C3 C2 C1 Br1 178.15(14) . . . . ?
C3 C2 C1 C6 0.1(3) . . . . ?
C3 C4 C5 Br3 179.30(13) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C18 C19 C20 C11 -0.2(3) . . . . ?
C18 C19 C20 C7 -179.94(18) . . . . ?
C18 C17 C12 C11 -1.3(3) . . . . ?
C18 C17 C12 C13 179.00(17) . . . . ?
C18 C17 C16 C15 -179.31(18) . . . . ?
C20 C11 C10 C9 -0.1(3) . . . . ?
C20 C11 C12 C17 0.5(2) . . . . ?
C20 C11 C12 C13 -179.86(17) . . . . ?
C20 C19 C18 C17 -0.6(3) . . . . ?
C20 C7 C8 C9 0.0(3) . . . . ?
C1 C6 C5 Br3 179.59(13) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
C1 C2 C3 Br2 177.72(14) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C12 C11 C10 C9 179.86(17) . . . . ?
C12 C11 C20 C19 0.3(2) . . . . ?
C12 C11 C20 C7 -179.97(16) . . . . ?
C12 C17 C18 C19 1.4(3) . . . . ?
C12 C17 C16 C15 1.0(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C16 C17 C18 C19 -178.29(18) . . . . ?
C16 C17 C12 C11 178.41(16) . . . . ?
C16 C17 C12 C13 -1.3(3) . . . . ?
C16 C15 C14 C13 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.593
_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_20170718c
_database_code_depnum_ccdc_archive 'CCDC 1586065'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F3 I3, 0.5(C14 H10)'
_chemical_formula_sum            'C13 H5 F3 I3'
_chemical_formula_weight         598.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1f1i1
_chemical_oxdiff_usercomment     1
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7866(4)
_cell_length_b                   24.3582(14)
_cell_length_c                   9.1687(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.930(6)
_cell_angle_gamma                90
_cell_volume                     1492.97(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5899
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      29.6280
_cell_measurement_theta_min      3.8360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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_density_diffrn    2.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.345
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(15)
_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 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  34.00   1.00    2.55    --   12.76 -37.00  90.00   54
  2  ω    -20.00  72.00   1.00    2.55    --   12.76  77.00  30.00   92
  3  ω     37.00 101.00   1.00    2.55    --   12.76 178.00 -60.00   64
  4  ω     48.00  74.00   1.00    2.55    --   12.76 178.00  90.00   26
  5  ω    -60.00  34.00   1.00    2.55    --   12.76 -77.00 -90.00   94
  6  ω    -19.00   6.00   1.00    2.55    --  -11.04 -99.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0279915000
_diffrn_orient_matrix_UB_12      -0.0269645000
_diffrn_orient_matrix_UB_13      0.0174356000
_diffrn_orient_matrix_UB_21      -0.0759321000
_diffrn_orient_matrix_UB_22      -0.0000142000
_diffrn_orient_matrix_UB_23      -0.0637042000
_diffrn_orient_matrix_UB_31      0.0684529000
_diffrn_orient_matrix_UB_32      -0.0110243000
_diffrn_orient_matrix_UB_33      -0.0425822000
_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                3351
_reflns_number_total             3851
_reflns_odcompleteness_completeness 99.75
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    ?
_refine_diff_density_max         1.375
_refine_diff_density_min         -1.435
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.058
_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)+(0.0123P)²+2.0149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0477
_refine_ls_wR_factor_ref         0.0508
_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: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: C7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5) C10(0.5) H10(0.5) C11(0.5)
 H11(0.5) C12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C20(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_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 0.6573(5) 0.66469(14) 0.3065(4) 0.0172(7) Uani 1 1 d . U . . .
C2 C 0.7341(5) 0.71523(14) 0.2789(4) 0.0170(7) Uani 1 1 d . U . . .
C3 C 0.6676(5) 0.76400(14) 0.3306(4) 0.0174(7) Uani 1 1 d . U . . .
C4 C 0.5131(5) 0.76065(14) 0.4099(4) 0.0176(7) Uani 1 1 d . U . . .
C5 C 0.4280(5) 0.71156(14) 0.4392(4) 0.0169(7) Uani 1 1 d . U . . .
C6 C 0.5019(5) 0.66433(14) 0.3867(4) 0.0178(7) Uani 1 1 d . U . . .
C7 C 1.0730(17) 0.5178(4) 0.9429(11) 0.0200(19) Uani 0.5 1 d . U P A -1
C8 C 1.2428(15) 0.5467(3) 0.9170(11) 0.0268(18) Uani 0.5 1 d . U P A -1
H8 H 1.3487 0.5514 0.9950 0.032 Uiso 0.5 1 calc R . P A -1
C9 C 1.2587(15) 0.5682(4) 0.7811(11) 0.030(2) Uani 0.5 1 d . U P A -1
H9 H 1.3729 0.5872 0.7675 0.036 Uiso 0.5 1 calc R . P A -1
C10 C 1.0985(16) 0.5608(4) 0.6628(12) 0.0221(19) Uani 0.5 1 d . U P A -1
H10 H 1.1082 0.5748 0.5700 0.026 Uiso 0.5 1 calc R . P A -1
C11 C 0.9297(17) 0.5335(4) 0.6819(11) 0.022(2) Uani 0.5 1 d . U P A -1
H11 H 0.8246 0.5293 0.6030 0.027 Uiso 0.5 1 calc R . P A -1
C12 C 0.9150(16) 0.5114(3) 0.8242(12) 0.0218(17) Uani 0.5 1 d . U P A -1
C13 C 0.7380(12) 0.4826(3) 0.8423(9) 0.0223(17) Uani 0.5 1 d . U P A -1
H13 H 0.6329 0.4790 0.7632 0.027 Uiso 0.5 1 calc R . P A -1
C14 C 0.7241(12) 0.4604(3) 0.9753(9) 0.0252(17) Uani 0.5 1 d . U P A -1
H14 H 0.6093 0.4409 0.9855 0.030 Uiso 0.5 1 calc R . P A -1
C15 C 0.8773(17) 0.4657(4) 1.0986(10) 0.021(2) Uani 0.5 1 d . U P A -1
C16 C 0.8562(17) 0.4425(4) 1.2399(12) 0.030(2) Uani 0.5 1 d . U P A -1
H16 H 0.7404 0.4236 1.2504 0.036 Uiso 0.5 1 calc R . P A -1
C17 C 1.006(2) 0.4484(5) 1.3566(13) 0.031(3) Uani 0.5 1 d . U P A -1
H17 H 0.9912 0.4330 1.4470 0.037 Uiso 0.5 1 calc R . P A -1
C18 C 1.1778(17) 0.4762(4) 1.3467(11) 0.034(2) Uani 0.5 1 d . U P A -1
H18 H 1.2775 0.4802 1.4294 0.041 Uiso 0.5 1 calc R . P A -1
C19 C 1.2018(18) 0.4985(4) 1.2111(11) 0.030(2) Uani 0.5 1 d . U P A -1
H19 H 1.3201 0.5168 1.2035 0.036 Uiso 0.5 1 calc R . P A -1
C20 C 1.0522(17) 0.4942(3) 1.0859(12) 0.0253(18) Uani 0.5 1 d . U P A -1
F1 F 0.8812(3) 0.71726(8) 0.1978(2) 0.0232(5) Uani 1 1 d . . . . .
F2 F 0.4440(3) 0.80738(8) 0.4605(2) 0.0236(5) Uani 1 1 d . . . . .
F3 F 0.4249(3) 0.61560(8) 0.4158(2) 0.0266(5) Uani 1 1 d . . . . .
I1 I 0.77469(4) 0.59337(2) 0.23270(3) 0.03098(8) Uani 1 1 d . . . . .
I2 I 0.79365(4) 0.83869(2) 0.28606(3) 0.02469(7) Uani 1 1 d . . . . .
I3 I 0.19246(3) 0.70843(2) 0.55663(2) 0.02260(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 1.377(5) . ?
C1 C6 1.386(5) . ?
C1 I1 2.073(3) . ?
C2 C3 1.383(5) . ?
C2 F1 1.345(4) . ?
C3 C4 1.378(5) . ?
C3 I2 2.081(3) . ?
C4 C5 1.374(5) . ?
C4 F2 1.344(4) . ?
C5 C6 1.374(5) . ?
C5 I3 2.077(3) . ?
C6 F3 1.342(4) . ?
C7 C8 1.404(12) . ?
C7 C12 1.398(15) . ?
C7 C20 1.462(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(13) . ?
C9 H9 0.9300 . ?
C9 C10 1.409(14) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(13) . ?
C11 H11 0.9300 . ?
C11 C12 1.431(14) . ?
C12 C13 1.426(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.352(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.403(13) . ?
C15 C16 1.443(14) . ?
C15 C20 1.396(14) . ?
C16 H16 0.9300 . ?
C16 C17 1.350(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(14) . ?
C19 H19 0.9300 . ?
C19 C20 1.399(14) . ?

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 116.7(3) . . ?
C2 C1 I1 120.7(2) . . ?
C6 C1 I1 122.6(3) . . ?
C1 C2 C3 123.3(3) . . ?
F1 C2 C1 118.4(3) . . ?
F1 C2 C3 118.3(3) . . ?
C2 C3 I2 121.0(2) . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 I2 122.1(3) . . ?
C5 C4 C3 122.6(3) . . ?
F2 C4 C3 118.3(3) . . ?
F2 C4 C5 119.1(3) . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 I3 121.3(2) . . ?
C6 C5 I3 120.7(2) . . ?
C5 C6 C1 122.5(3) . . ?
F3 C6 C1 117.9(3) . . ?
F3 C6 C5 119.5(3) . . ?
C8 C7 C20 123.9(11) . . ?
C12 C7 C8 117.8(9) . . ?
C12 C7 C20 118.3(13) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.7(10) . . ?
C9 C8 H8 118.7 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(9) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(10) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(10) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 120.2(9) . . ?
C7 C12 C13 120.9(10) . . ?
C13 C12 C11 119.0(11) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(8) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.1(8) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C16 120.8(11) . . ?
C20 C15 C14 120.1(10) . . ?
C20 C15 C16 119.1(9) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.5(10) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.3(11) . . ?
C18 C17 H17 118.9 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.1(11) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.5(12) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C7 119.1(13) . . ?
C15 C20 C19 118.5(10) . . ?
C19 C20 C7 122.5(11) . . ?

_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 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.798
