# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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. 
# 
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data_rs090418_1_2
_database_code_depnum_ccdc_archive 'CCDC 1847505'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_audit_creation_date             2018-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 F5 I O, Br'
_chemical_formula_sum            'C15 H11 Br F5 I O'
_chemical_formula_weight         509.05
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H11BrF5IO
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   38.2117(7)
_cell_length_b                   18.5754(5)
_cell_length_c                   9.3073(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6606.3(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    7235
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      33.6040
_cell_measurement_theta_min      3.0500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.408
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.047
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 -26 0 0.0198
9 26 0 0.0126
54 -2 0 0.0388
-54 2 0 0.0291
17 0 -12 0.1177
-14 1 -13 0.1130
-8 -1 13 0.1128
14 -16 -10 0.0974
35 -20 0 0.0282
-35 20 0 0.0208
15 -25 0 0.0191
-15 25 0 0.0164
-33 -20 -2 0.0339
30 22 -1 0.0235
4 15 -11 0.0971
-44 -4 7 0.0731
-53 -3 -2 0.0314
-49 -11 1 0.0306
-8 -7 12 0.1071
-40 -18 0 0.0231
-16 25 -1 0.0166

_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.032
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.0001 -25.9999 -0.0000 0.9986 -0.1298 0.0023
9.0001 25.9999 0.0000 -0.9986 0.1298 -0.0023
53.9995 -1.9999 0.0000 -0.2109 -0.9197 -0.3461
-53.9995 1.9999 -0.0000 0.2109 0.9197 0.3461
16.9998 0.0001 -12.0000 -0.1325 -0.5959 0.7505
-14.0000 1.0001 -13.0000 -0.0096 -0.0956 1.0204
-7.9998 -1.0001 13.0000 0.1253 0.4616 -0.8811
13.9997 -15.9999 -10.0000 0.4759 -0.6658 0.5928
34.9996 -19.9999 0.0000 0.5476 -0.7972 -0.2637
-34.9996 19.9999 -0.0000 -0.5476 0.7972 0.2637
14.9997 -24.9999 -0.0000 0.8357 -0.5183 -0.1476
-14.9997 24.9999 0.0000 -0.8357 0.5183 0.1476
-32.9999 -19.9999 -2.0000 0.8981 0.2817 0.3099
29.9999 21.9999 -1.0000 -0.9663 -0.2886 -0.0722
4.0000 15.0000 -11.0000 -0.6093 -0.1923 0.7929
-43.9996 -4.0001 7.0000 0.4029 0.8715 -0.2304
-52.9996 -3.0000 -2.0000 0.3814 0.7971 0.4723
-48.9997 -11.0000 1.0000 0.6638 0.7229 0.2156
-7.9999 -7.0001 12.0000 0.3412 0.3709 -0.8223
-39.9998 -18.0000 -0.0000 0.8689 0.4718 0.2154
-15.9997 24.9999 -1.0000 -0.8341 0.5088 0.2254

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18693
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.678
_diffrn_reflns_theta_min         2.924
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  42.00   0.50   20.96    --   11.92 -99.00 120.00  114
  2  ω     -5.00  22.00   0.50   20.96    --  -13.32 -99.00  30.00   54
  3  ω    -20.00  22.00   0.50   20.96    --  -13.32 -99.00 120.00   84
  4  ω    -20.00  12.00   0.50   20.96    --  -13.32 -99.00 150.00   64
  5  ω    -82.00 -12.00   0.50   20.96    --  -13.32 -57.00   0.00  140
  6  ω    -28.00  46.00   0.50   20.96    --  -13.32  19.00   0.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0052602000
_diffrn_orient_matrix_UB_12      -0.0365855000
_diffrn_orient_matrix_UB_13      0.0035868000
_diffrn_orient_matrix_UB_21      -0.0166336000
_diffrn_orient_matrix_UB_22      0.0107517000
_diffrn_orient_matrix_UB_23      0.0260954000
_diffrn_orient_matrix_UB_31      -0.0063319000
_diffrn_orient_matrix_UB_32      0.0021038000
_diffrn_orient_matrix_UB_33      -0.0715148000
_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              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.678
_reflns_number_gt                4730
_reflns_number_total             5672
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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         1.704
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 
;
 Flack x determined using 1696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.022
_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)+(0.0551P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.93 with sigma of 0.02
 C13-H1
 1.897586 with sigma of 0.02
 I1-H1
 3.180853 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.52214(2) 0.62660(2) 0.55220(3) 0.02367(9) Uani 1 1 d D . . . .
F1 F 0.45172(9) 0.6977(2) 0.4365(4) 0.0354(8) Uani 1 1 d . . . . .
F2 F 0.42797(10) 0.8349(2) 0.4345(5) 0.0493(10) Uani 1 1 d . . . . .
F3 F 0.46693(13) 0.9412(2) 0.5565(7) 0.0652(14) Uani 1 1 d . . . . .
F4 F 0.53110(14) 0.9106(3) 0.6701(6) 0.0576(12) Uani 1 1 d . . . . .
F5 F 0.55589(9) 0.7744(2) 0.6584(5) 0.0412(9) Uani 1 1 d . . . . .
O1 O 0.55305(9) 0.5106(2) 0.5127(5) 0.0318(8) Uani 1 1 d D . . . .
H1 H 0.5550(10) 0.4726(17) 0.584(5) 0.048 Uiso 1 1 d DR . . . .
C1 C 0.47166(14) 0.7498(3) 0.4920(6) 0.0270(11) Uani 1 1 d . . . . .
C2 C 0.45918(15) 0.8192(4) 0.4921(8) 0.0360(14) Uani 1 1 d . . . . .
C3 C 0.4791(2) 0.8730(3) 0.5561(16) 0.0362(12) Uani 1 1 d . . . . .
C4 C 0.5117(2) 0.8581(4) 0.6122(8) 0.0384(14) Uani 1 1 d . . . . .
C5 C 0.52360(14) 0.7888(4) 0.6078(7) 0.0308(12) Uani 1 1 d . . . . .
C6 C 0.50409(13) 0.7339(3) 0.5487(6) 0.0260(10) Uani 1 1 d . . . . .
C7 C 0.56572(12) 0.6464(3) 0.4108(6) 0.0240(10) Uani 1 1 d . . . . .
C8 C 0.56803(14) 0.7123(3) 0.3402(6) 0.0284(11) Uani 1 1 d . . . . .
H8 H 0.550397 0.746445 0.350158 0.034 Uiso 1 1 calc R . . . .
C9 C 0.59707(14) 0.7264(3) 0.2547(7) 0.0342(12) Uani 1 1 d . . . . .
H9 H 0.599193 0.770328 0.207687 0.041 Uiso 1 1 calc R . . . .
C10 C 0.62293(15) 0.6741(4) 0.2401(7) 0.0357(13) Uani 1 1 d . . . . .
H10 H 0.642653 0.683322 0.184524 0.043 Uiso 1 1 calc R . . . .
C11 C 0.61918(14) 0.6085(3) 0.3084(7) 0.0322(12) Uani 1 1 d . . . . .
H11 H 0.636241 0.573540 0.293659 0.039 Uiso 1 1 calc R . . . .
C12 C 0.59127(14) 0.5921(3) 0.3980(6) 0.0267(11) Uani 1 1 d . . . . .
C13 C 0.58935(13) 0.5220(3) 0.4791(7) 0.0295(12) Uani 1 1 d D . . . .
C14 C 0.61008(18) 0.5287(4) 0.6200(8) 0.0424(16) Uani 1 1 d . . . . .
H14A H 0.600398 0.566799 0.677139 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.634129 0.539170 0.598706 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.608668 0.484174 0.672163 0.064 Uiso 1 1 calc GR . . . .
C15 C 0.60164(18) 0.4583(4) 0.3912(10) 0.049(2) Uani 1 1 d . . . . .
H15A H 0.595633 0.414464 0.440016 0.073 Uiso 1 1 calc GR . . . .
H15B H 0.626563 0.460767 0.379141 0.073 Uiso 1 1 calc GR . . . .
H15C H 0.590522 0.459188 0.298727 0.073 Uiso 1 1 calc GR . . . .
Br1 Br 0.45847(2) 0.60418(3) 0.76451(8) 0.03147(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
I1 O1 2.485(4) . ?
I1 C6 2.109(5) . ?
I1 C7 2.154(5) . ?
F1 C1 1.336(7) . ?
F2 C2 1.340(7) . ?
F3 C3 1.350(8) . ?
F4 C4 1.338(8) . ?
F5 C5 1.348(7) . ?
O1 H1 0.97(2) . ?
O1 C13 1.438(6) . ?
C1 C2 1.373(9) . ?
C1 C6 1.379(7) . ?
C2 C3 1.389(12) . ?
C3 C4 1.379(13) . ?
C4 C5 1.366(10) . ?
C5 C6 1.378(8) . ?
C7 C8 1.392(8) . ?
C7 C12 1.408(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(8) . ?
C12 C13 1.507(8) . ?
C13 C14 1.537(9) . ?
C13 C15 1.513(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 I1 O1 166.57(17) . . ?
C6 I1 C7 94.7(2) . . ?
C7 I1 O1 71.95(18) . . ?
I1 O1 H1 124(2) . . ?
C13 O1 I1 111.3(3) . . ?
C13 O1 H1 100(2) . . ?
F1 C1 C2 118.8(5) . . ?
F1 C1 C6 120.3(5) . . ?
C2 C1 C6 120.9(6) . . ?
F2 C2 C1 120.9(6) . . ?
F2 C2 C3 120.1(6) . . ?
C1 C2 C3 119.0(6) . . ?
F3 C3 C2 119.3(8) . . ?
F3 C3 C4 119.8(8) . . ?
C4 C3 C2 120.9(6) . . ?
F4 C4 C3 120.6(7) . . ?
F4 C4 C5 120.8(7) . . ?
C5 C4 C3 118.6(6) . . ?
F5 C5 C4 118.9(6) . . ?
F5 C5 C6 119.1(6) . . ?
C4 C5 C6 121.9(6) . . ?
C1 C6 I1 120.2(4) . . ?
C5 C6 I1 121.1(4) . . ?
C5 C6 C1 118.7(5) . . ?
C8 C7 I1 119.2(4) . . ?
C8 C7 C12 123.1(5) . . ?
C12 C7 I1 117.7(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.1(5) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(6) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 118.3 . . ?
C10 C11 C12 123.3(5) . . ?
C12 C11 H11 118.3 . . ?
C7 C12 C13 122.9(5) . . ?
C11 C12 C7 115.3(5) . . ?
C11 C12 C13 121.8(5) . . ?
O1 C13 C12 106.5(4) . . ?
O1 C13 C14 108.9(5) . . ?
O1 C13 C15 107.5(5) . . ?
C12 C13 C14 109.4(5) . . ?
C12 C13 C15 113.0(6) . . ?
C15 C13 C14 111.3(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_date_sample_data_collection 2018-04-09
_olex2_date_sample_submission    2018-04-09
_olex2_submission_original_sample_id rs090418_1_2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.806
####################################################################### 
# 
# 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_rs091117_1_1
_database_code_depnum_ccdc_archive 'CCDC 1847506'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_audit_creation_date             2017-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 Br F4 I O2, Cl'
_chemical_formula_sum            'C17 H15 Br Cl F4 I O2'
_chemical_formula_weight         569.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H15BrClF4IO2
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.35480(10)
_cell_length_b                   8.05860(10)
_cell_length_c                   21.0488(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.6110(10)
_cell_angle_gamma                90
_cell_volume                     1916.82(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    53837
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.1970
_cell_measurement_theta_min      4.2210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.295
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_correction_T_min  0.186
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 -4 0.0180
7 0 4 0.0117
1 5 0 0.0692
4 0 -12 0.0389
-4 0 12 0.0450
0 -5 -2 0.0669
-1 5 -1 0.0694
-2 0 -13 0.0330
2 0 13 0.0399
2 -4 6 0.0720
-6 0 -6 0.0182
-7 0 7 0.0382
-3 -2 12 0.0613

_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0000 -0.0000 -4.0000 0.3249 -0.9727 -0.0196
7.0000 0.0000 4.0000 -0.3249 0.9727 0.0196
1.0000 5.0000 -0.0000 -0.2494 0.0358 0.9322
4.0000 0.0000 -12.0000 -0.9658 -0.1194 -0.1865
-4.0000 -0.0000 12.0000 0.9658 0.1194 0.1865
0.0000 -5.0000 -2.0000 0.0626 -0.0184 -0.9650
-1.0000 5.0000 -1.0000 -0.1488 -0.2354 0.9286
-2.0000 -0.0000 -13.0000 -0.5546 -0.8384 -0.1697
2.0000 0.0000 13.0000 0.5546 0.8384 0.1697
2.0000 -4.0000 6.0000 0.3099 0.5684 -0.6770
-6.0000 -0.0000 -6.0000 0.1381 -0.9553 -0.0524
-7.0000 -0.0000 7.0000 0.9256 -0.4528 0.1326
-3.0000 -2.0000 12.0000 0.9569 0.2618 -0.1935

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68822
_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         79.729
_diffrn_reflns_theta_min         4.221
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_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   -129.00 -40.00   0.50    0.27    --  -62.00 -72.00-177.10  178
  2  ω   -133.00 -44.00   0.50    0.27    --  -66.00 -72.00 -97.61  178
  3  ω   -122.00 -33.00   0.50    0.15    --  -54.00 -70.00 -71.12  178
  4  ω   -137.00 -48.00   0.50    0.27    --  -70.00 -72.00-130.26  178
  5  ω   -138.00 -49.00   0.50    0.27    --  -70.00 -70.00-161.82  178
  6  ω   -121.00 -32.00   0.50    0.15    --  -54.00 -73.00 -14.92  178
  7  ω   -139.00 -51.00   0.50    0.27    --  -70.00 -65.00  30.99  176
  8  ω   -138.00 -50.00   0.50    0.27    --  -70.00 -68.00  58.25  176
  9  ω   -125.00 -36.00   0.50    0.15    --  -58.00 -73.00 117.81  178
 10  ω   -137.00 -49.00   0.50    0.27    --  -70.00 -71.00 155.63  176
 11  ω   -137.00 -48.00   0.50    0.27    --  -70.00 -73.00  87.33  178
 12  ω   -137.00 -49.00   0.50    0.27    --  -70.00 -71.00  92.45  176
 13  ω   -139.00 -51.00   0.50    0.27    --  -70.00 -65.00  17.08  176
 14  ω   -140.00 -52.00   0.50    0.27    --  -70.00 -63.00 -36.88  176
 15  ω   -137.00 -48.00   0.50    0.27    --  -70.00 -72.00 -72.20  178
 16  ω   -139.00 -51.00   0.50    0.27    --  -70.00 -66.00-121.24  176
 17  ω   -139.00 -50.00   0.50    0.27    --  -70.00 -67.00 -59.09  178
 18  ω   -139.00 -51.00   0.50    0.27    --  -70.00 -65.00  -8.52  176
 19  ω   -138.00 -50.00   0.50    0.27    --  -70.00 -68.00 116.51  176
 20  ω     52.00  81.00   0.50    0.27    --  110.00 -57.00-150.00   58
 21  ω     48.00  80.00   0.50    0.27    --  110.00 -57.00   0.00   64
 22  ω     44.00  72.00   0.50    0.27    --  110.00 -77.00 -30.00   56
 23  ω    107.00 133.00   0.50    0.27    --  110.00 -77.00 -30.00   52
 24  ω    -50.00  40.00   0.50    0.15    --  -26.00  79.00 -98.85  180
 25  ω    -73.00  17.00   0.50    0.15    --  -49.37  77.00  90.00  180
 26  ω   -124.00 -36.00   0.50    0.15    --  -49.37 -44.00 141.06  176
 27  ω   -124.00 -36.00   0.50    0.15    --  -49.37 -44.00  75.92  176
 28  ω     52.00 110.00   0.50    0.27    --  110.00 -77.00 120.00  116
 29  ω     13.00  43.00   0.50    0.15    --   38.00  80.00-142.16   60
 30  ω     14.00  44.00   0.50    0.15    --   38.00  79.00 -46.43   60
 31  ω     37.00 125.00   0.50    0.15    --   49.37  38.00-150.00  176
 32  ω     34.00 121.00   0.50    0.15    --   49.37  57.00-120.00  174
 33  ω     21.00 109.00   0.50    0.15    --   42.00  72.00 129.54  176
 34  ω     37.00 125.00   0.50    0.15    --   49.37  38.00 150.00  176
 35  ω     29.00 117.00   0.50    0.15    --   50.00  72.00  63.76  176
 36  ω     12.00  40.00   0.50    0.15    --   38.00  82.00 -30.03   56
 37  ω     86.00 113.00   0.50    0.27    --  110.00  77.00  30.00   54
 38  ω     87.00 177.00   0.50    0.27    --  110.00  77.00   0.00  180
 39  ω     86.00 120.00   0.50    0.27    --  110.00  77.00  90.00   68
 40  ω    129.00 170.00   0.50    0.27    --  110.00  77.00  30.00   82
 41  ω    125.00 168.00   0.50    0.27    --  110.00  77.00  90.00   86
 42  ω    -95.00  -9.00   0.50    0.27    --  -70.00 125.00-150.00  172
 43  ω    134.00 174.00   0.50    0.27    --  110.00  77.00-150.00   80
 44  ω     59.00 120.00   0.50    0.15    --   49.37 178.00-150.00  122
 45  ω    102.00 129.00   0.50    0.27    --  110.00  57.00 -90.00   54
 46  ω     88.00 115.00   0.50    0.27    --  110.00  77.00-150.00   54
 47  ω     67.00 155.00   0.50    0.27    --   86.00  66.00-176.03  176
 48  ω     59.00 148.00   0.50    0.15    --   78.00  65.00  34.57  178
 49  ω     72.00  98.00   0.50    0.27    --   90.00  63.00 162.48   52
 50  ω     57.00 145.00   0.50    0.15    --   78.00  72.00  66.97  176
 51  ω     56.00 145.00   0.50    0.15    --   78.00  73.00   9.97  178
 52  ω    122.00 169.00   0.50    0.27    --   94.00  44.00 -98.83   94
 53  ω     81.00 106.00   0.50    0.27    --   94.00  44.00 -98.83   50
 54  ω     96.00 149.00   0.50    0.27    --  110.00  57.00-150.00  106
 55  ω     87.00 177.00   0.50    0.27    --  110.00  77.00 -60.00  180
 56  ω    120.00 161.00   0.50    0.27    --   94.00  45.00 153.06   82
 57  ω     81.00 117.00   0.50    0.27    --   94.00  45.00 153.06   72
 58  ω     99.00 125.00   0.50    0.27    --  110.00  38.00 120.00   52
 59  ω     86.00 176.00   0.50    0.27    --  110.00  77.00  60.00  180
 60  ω    127.00 174.00   0.50    0.27    --  110.00  77.00 -90.00   94
 61  ω     94.00 120.00   0.50    0.27    --  110.00  57.00 -60.00   52
 62  ω     87.00 113.00   0.50    0.27    --  110.00  77.00 -90.00   52
 63  ω     94.00 137.00   0.50    0.27    --  110.00  57.00 -30.00   86
 64  ω    148.00 174.00   0.50    0.27    --  110.00  57.00 -30.00   52
 65  ω     98.00 131.00   0.50    0.27    --  110.00  38.00  90.00   66
 66  ω     97.00 178.00   0.50    0.27    --  110.00  57.00 120.00  162
 67  ω     99.00 152.00   0.50    0.27    --  110.00  38.00  60.00  106
 68  ω    137.00 177.00   0.50    0.27    --  110.00  77.00-120.00   80
 69  ω     86.00 170.00   0.50    0.27    --  110.00  77.00-180.00  168
 70  ω     90.00 116.00   0.50    0.27    --  110.00  77.00-120.00   52
 71  ω     94.00 144.00   0.50    0.27    --  110.00  57.00-120.00  100
 72  ω    146.00 172.00   0.50    0.27    --  110.00  77.00 -30.00   52
 73  ω     86.00 141.00   0.50    0.27    --  110.00  77.00 -30.00  110
 74  ω     87.00 170.00   0.50    0.27    --  110.00  77.00 150.00  166
 75  ω     42.00 110.00   0.50    0.27    --  110.00 -99.00  30.00  136
 76  ω     44.00 110.00   0.50    0.27    --  110.00 -99.00 120.00  132
 77  ω     69.00 122.00   0.50    0.27    --  110.00-125.00 -30.00  106
 78  ω     41.00  91.00   0.50    0.27    --  110.00 -99.00-120.00  100
 79  ω     49.00  95.00   0.50    0.27    --  110.00 -99.00 -30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0776237000
_diffrn_orient_matrix_UB_12      -0.0343648000
_diffrn_orient_matrix_UB_13      0.0546073000
_diffrn_orient_matrix_UB_21      0.1119529000
_diffrn_orient_matrix_UB_22      -0.0152290000
_diffrn_orient_matrix_UB_23      0.0472671000
_diffrn_orient_matrix_UB_31      -0.0051109000
_diffrn_orient_matrix_UB_32      0.1874604000
_diffrn_orient_matrix_UB_33      0.0138378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4043
_reflns_number_total             4118
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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         0.573
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.090
_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)+(0.0207P)²+2.9419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.93 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.89085(2) 0.31358(2) 0.42330(2) 0.01691(5) Uani 1 1 d . . . . .
Br1 Br 0.27319(2) 1.00215(3) 0.43844(2) 0.02573(7) Uani 1 1 d . . . . .
F1 F 0.66161(14) 0.4850(2) 0.32605(7) 0.0311(3) Uani 1 1 d . . . . .
F4 F 0.68032(13) 0.09815(19) 0.40138(8) 0.0308(3) Uani 1 1 d . . . . .
F3 F 0.74049(13) 0.17786(19) 0.31168(7) 0.0288(3) Uani 1 1 d . . . . .
F2 F 0.52579(13) 0.2990(2) 0.33274(7) 0.0311(3) Uani 1 1 d . . . . .
O2 O 1.07306(16) 0.4286(2) 0.33774(8) 0.0252(4) Uani 1 1 d D . . . .
H1 H 1.117(3) 0.394(4) 0.3735(11) 0.038 Uiso 1 1 d DR . . . .
O1 O 0.60677(15) 0.4205(2) 0.42266(8) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.9459(2) -0.0392(3) 0.40405(11) 0.0216(5) Uani 1 1 d . . . . .
H1A H 0.907703 -0.044914 0.441095 0.026 Uiso 1 1 calc R . . . .
C9 C 0.9686(2) 0.1131(3) 0.37701(11) 0.0182(4) Uani 1 1 d . . . . .
C4 C 0.5262(2) 0.5558(3) 0.42369(11) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.5730(2) 0.7122(3) 0.43379(12) 0.0253(5) Uani 1 1 d . . . . .
H4 H 0.654429 0.728807 0.437820 0.030 Uiso 1 1 calc R . . . .
C14 C 1.0279(2) 0.1333(3) 0.32236(11) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.3755(2) 0.8172(3) 0.43162(11) 0.0218(5) Uani 1 1 d . . . . .
C11 C 0.9812(2) -0.1823(3) 0.37495(12) 0.0248(5) Uani 1 1 d . . . . .
H7 H 0.968000 -0.285751 0.392532 0.030 Uiso 1 1 calc R . . . .
C2 C 0.4960(2) 0.8447(3) 0.43784(11) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.525452 0.951579 0.444709 0.028 Uiso 1 1 calc R . . . .
C13 C 1.0591(2) -0.0155(3) 0.29426(11) 0.0219(5) Uani 1 1 d . . . . .
H9 H 1.096703 -0.010625 0.257008 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4053(2) 0.5255(3) 0.41867(11) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.375952 0.418253 0.412949 0.029 Uiso 1 1 calc R . . . .
C15 C 1.0602(2) 0.2984(3) 0.29170(12) 0.0236(5) Uani 1 1 d . . . . .
C8 C 0.7204(2) 0.2292(3) 0.37049(11) 0.0219(5) Uani 1 1 d . . . . .
C6 C 0.3291(2) 0.6595(3) 0.42239(12) 0.0250(5) Uani 1 1 d . . . . .
H13 H 0.247667 0.643120 0.418701 0.030 Uiso 1 1 calc R . . . .
C12 C 1.0365(2) -0.1698(3) 0.31925(12) 0.0255(5) Uani 1 1 d . . . . .
H14 H 1.058557 -0.265325 0.298642 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6257(2) 0.3642(3) 0.36409(11) 0.0228(5) Uani 1 1 d . . . . .
C17 C 0.9609(3) 0.3558(4) 0.24268(14) 0.0397(7) Uani 1 1 d . . . . .
H16A H 0.890305 0.373687 0.263389 0.060 Uiso 1 1 calc GR . . . .
H16B H 0.946288 0.272461 0.210291 0.060 Uiso 1 1 calc GR . . . .
H16C H 0.983569 0.457532 0.223481 0.060 Uiso 1 1 calc GR . . . .
C16 C 1.1760(3) 0.2860(4) 0.26099(17) 0.0439(8) Uani 1 1 d . . . . .
H17A H 1.197004 0.393524 0.245997 0.066 Uiso 1 1 calc GR . . . .
H17B H 1.166448 0.210147 0.225705 0.066 Uiso 1 1 calc GR . . . .
H17C H 1.237350 0.246687 0.291914 0.066 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.12620(5) 0.35652(7) 0.48150(2) 0.02076(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
I1 C9 2.123(2) . ?
I1 C8 2.241(2) . ?
Br1 C1 1.903(3) . ?
F1 C7 1.349(3) . ?
F4 C8 1.343(3) . ?
F3 C8 1.346(3) . ?
F2 C7 1.361(3) . ?
O2 H1 0.908(18) . ?
O2 C15 1.426(3) . ?
O1 C4 1.425(3) . ?
O1 C7 1.351(3) . ?
C10 H1A 0.9300 . ?
C10 C9 1.387(3) . ?
C10 C11 1.384(4) . ?
C9 C14 1.398(3) . ?
C4 C3 1.377(4) . ?
C4 C5 1.388(3) . ?
C3 H4 0.9300 . ?
C3 C2 1.388(4) . ?
C14 C13 1.398(3) . ?
C14 C15 1.539(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.382(4) . ?
C11 H7 0.9300 . ?
C11 C12 1.387(4) . ?
C2 H8 0.9300 . ?
C13 H9 0.9300 . ?
C13 C12 1.383(4) . ?
C5 H10 0.9300 . ?
C5 C6 1.390(4) . ?
C15 C17 1.524(4) . ?
C15 C16 1.524(4) . ?
C8 C7 1.527(4) . ?
C6 H13 0.9300 . ?
C12 H14 0.9300 . ?
C17 H16A 0.9600 . ?
C17 H16B 0.9600 . ?
C17 H16C 0.9600 . ?
C16 H17A 0.9600 . ?
C16 H17B 0.9600 . ?
C16 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 I1 C8 85.35(9) . . ?
C15 O2 H1 110(2) . . ?
C7 O1 C4 115.53(18) . . ?
C9 C10 H1A 120.6 . . ?
C11 C10 H1A 120.6 . . ?
C11 C10 C9 118.8(2) . . ?
C10 C9 I1 112.49(16) . . ?
C10 C9 C14 124.4(2) . . ?
C14 C9 I1 122.97(18) . . ?
C3 C4 O1 117.7(2) . . ?
C3 C4 C5 122.4(2) . . ?
C5 C4 O1 119.8(2) . . ?
C4 C3 H4 120.7 . . ?
C4 C3 C2 118.6(2) . . ?
C2 C3 H4 120.7 . . ?
C9 C14 C13 114.2(2) . . ?
C9 C14 C15 126.9(2) . . ?
C13 C14 C15 118.9(2) . . ?
C2 C1 Br1 118.27(19) . . ?
C2 C1 C6 121.4(2) . . ?
C6 C1 Br1 120.27(18) . . ?
C10 C11 H7 120.4 . . ?
C10 C11 C12 119.2(2) . . ?
C12 C11 H7 120.4 . . ?
C3 C2 H8 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H8 120.1 . . ?
C14 C13 H9 118.4 . . ?
C12 C13 C14 123.1(2) . . ?
C12 C13 H9 118.4 . . ?
C4 C5 H10 120.8 . . ?
C4 C5 C6 118.4(2) . . ?
C6 C5 H10 120.8 . . ?
O2 C15 C14 111.34(19) . . ?
O2 C15 C17 104.9(2) . . ?
O2 C15 C16 107.5(2) . . ?
C17 C15 C14 110.8(2) . . ?
C17 C15 C16 110.1(2) . . ?
C16 C15 C14 111.9(2) . . ?
F4 C8 I1 108.42(15) . . ?
F4 C8 F3 107.4(2) . . ?
F4 C8 C7 109.49(19) . . ?
F3 C8 I1 109.51(15) . . ?
F3 C8 C7 108.60(19) . . ?
C7 C8 I1 113.21(16) . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H13 120.3 . . ?
C5 C6 H13 120.3 . . ?
C11 C12 H14 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H14 119.9 . . ?
F1 C7 F2 106.07(18) . . ?
F1 C7 O1 112.6(2) . . ?
F1 C7 C8 108.40(19) . . ?
F2 C7 C8 108.3(2) . . ?
O1 C7 F2 111.89(19) . . ?
O1 C7 C8 109.44(19) . . ?
C15 C17 H16A 109.5 . . ?
C15 C17 H16B 109.5 . . ?
C15 C17 H16C 109.5 . . ?
H16A C17 H16B 109.5 . . ?
H16A C17 H16C 109.5 . . ?
H16B C17 H16C 109.5 . . ?
C15 C16 H17A 109.5 . . ?
C15 C16 H17B 109.5 . . ?
C15 C16 H17C 109.5 . . ?
H17A C16 H17B 109.5 . . ?
H17A C16 H17C 109.5 . . ?
H17B C16 H17C 109.5 . . ?

_olex2_date_sample_data_collection 2017-11-09
_olex2_date_sample_submission    2017-11-09
_olex2_submission_original_sample_id rs091117_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_rs300118_1_1
_database_code_depnum_ccdc_archive 'CCDC 1847507'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C15 H9 Br Cl F4 I O3'
_chemical_formula_sum            'C15 H9 Br Cl F4 I O3'
_chemical_formula_weight         555.49
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   7.9867(2)
_cell_length_b                   8.2391(2)
_cell_length_c                   13.6897(2)
_cell_angle_alpha                74.798(2)
_cell_angle_beta                 84.253(2)
_cell_angle_gamma                86.584(2)
_cell_volume                     864.41(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25100
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.1290
_cell_measurement_theta_min      3.3470
_exptl_absorpt_coefficient_mu    19.206
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.270
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.1340
_exptl_crystal_description       plate
_exptl_crystal_F_000             528.7898
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -2 6 0.0081
3 0 -6 0.0251
-1 5 0 0.0487
3 -4 -4 0.0568
-3 -3 -7 0.0367
3 3 7 0.0293
-4 2 -4 0.0447
4 -2 3 0.0592
1 -3 -7 0.0458
0 0 -9 0.0271
-1 4 -4 0.0420
1 -1 -9 0.0297
4 4 2 0.0236
-4 -2 -6 0.0378
1 1 -7 0.0207
4 3 -2 0.0138
5 -1 -3 0.0441

_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.028
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33322
_diffrn_reflns_theta_full        79.8599
_diffrn_reflns_theta_max         79.86
_diffrn_reflns_theta_min         3.36
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.9785
_diffrn_measured_fraction_theta_max 0.9785
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00 110.00   0.50    0.10    --   42.00  71.00  -7.95  178
  2  ω     37.00 125.00   0.50    0.10    --   49.37  38.00 150.00  176
  3  ω     34.00 121.00   0.50    0.10    --   49.37  57.00  90.00  174
  4  ω     20.00 109.00   0.50    0.10    --   42.00  73.00 151.88  178
  5  ω     37.00 125.00   0.50    0.10    --   49.37  38.00 -30.00  176
  6  ω     37.00 125.00   0.50    0.10    --   49.37  38.00  30.00  176
  7  ω     86.00 177.00   0.50    0.14    --  110.00  77.00  60.00  182
  8  ω     86.00 177.00   0.50    0.14    --  110.00  77.00  90.00  182
  9  ω     33.00 121.00   0.50    0.10    --   54.00  72.00  13.49  176
 10  ω     53.00 142.00   0.50    0.10    --   74.00  70.00 -20.82  178
 11  ω     32.00 121.00   0.50    0.10    --   54.00  73.00-165.02  178
 12  ω     86.00 177.00   0.50    0.14    --  110.00  77.00 -60.00  182
 13  ω     86.00 177.00   0.50    0.14    --  110.00  77.00 -30.00  182
 14  ω     86.00 177.00   0.50    0.14    --  110.00  77.00-180.00  182
 15  ω     98.00 178.00   0.50    0.14    --  110.00  38.00-150.00  160
 16  ω     86.00 177.00   0.50    0.14    --  110.00  77.00-150.00  182
 17  ω     94.00 178.00   0.50    0.14    --  110.00  57.00 -90.00  168
 18  ω     94.00 178.00   0.50    0.14    --  110.00  57.00 -30.00  168
 19  ω     94.00 178.00   0.50    0.14    --  110.00  57.00  30.00  168
 20  ω     86.00 177.00   0.50    0.14    --  110.00  77.00 120.00  182
 21  ω     86.00 177.00   0.50    0.14    --  110.00  77.00 150.00  182
 22  ω    -94.00  -3.00   0.50    0.14    --  -70.00  77.00 -60.00  182
 23  ω   -140.00 -51.00   0.50    0.14    --  -70.00 -64.00   3.87  178
 24  ω   -137.00 -48.00   0.50    0.14    --  -70.00 -73.00-112.17  178
 25  ω   -137.00 -48.00   0.50    0.14    --  -70.00 -72.00 -45.80  178
 26  ω   -138.00 -49.00   0.50    0.14    --  -70.00 -69.00  78.26  178
 27  ω   -138.00 -49.00   0.50    0.14    --  -70.00 -70.00  30.82  178
 28  ω   -137.00 -48.00   0.50    0.14    --  -70.00 -72.00 -56.88  178
 29  ω   -138.00 -49.00   0.50    0.14    --  -70.00 -69.00 123.24  178
 30  ω   -137.00 -49.00   0.50    0.14    --  -70.00 -71.00-158.01  176
 31  ω   -125.00 -37.00   0.50    0.10    --  -49.37 -19.00 -60.00  176
 32  ω   -138.00 -49.00   0.50    0.14    --  -70.00 -69.00 137.26  178
 33  ω   -137.00 -48.00   0.50    0.14    --  -70.00 -72.00 106.94  178
 34  ω   -138.00 -49.00   0.50    0.14    --  -70.00 -70.00  57.87  178
 35  ω   -125.00 -36.00   0.50    0.10    --  -58.00 -72.00  45.60  178
 36  ω   -137.00 -48.00   0.50    0.14    --  -70.00 -73.00-102.37  178
 37  ω   -140.00 -52.00   0.50    0.14    --  -70.00 -63.00 -93.12  176
 38  ω    -26.00  49.00   0.50    0.10    --   49.37 -38.00  90.00  150
 39  ω     38.00  84.00   0.50    0.14    --  110.00 -57.00 -90.00   92
 40  ω     94.00 178.00   0.50    0.14    --  110.00  57.00 -60.00  168
 41  ω     94.00 178.00   0.50    0.14    --  110.00  57.00 150.00  168
 42  ω     98.00 178.00   0.50    0.14    --  110.00  38.00  90.00  160
 43  ω     98.00 178.00   0.50    0.14    --  110.00  38.00-120.00  160
 44  ω     86.00 177.00   0.50    0.14    --  110.00  77.00   0.00  182
 45  ω     98.00 178.00   0.50    0.14    --  110.00  38.00 -90.00  160
 46  ω     86.00 177.00   0.50    0.14    --  110.00  77.00-120.00  182
 47  ω     94.00 178.00   0.50    0.14    --  110.00  57.00   0.00  168
 48  ω     86.00 177.00   0.50    0.14    --  110.00  77.00  30.00  182
 49  ω    -95.00  -9.00   0.50    0.14    --  -70.00 125.00  30.00  172
 50  ω    -38.00 -12.00   0.50    0.10    --   14.00 131.00 158.07   52
 51  ω      7.00  36.00   0.50    0.10    --   34.00  85.00  85.51   58
 52  ω      7.00  36.00   0.50    0.10    --   34.00  85.00-127.84   58
 53  ω      7.00  36.00   0.50    0.10    --   34.00  85.00 -21.21   58
 54  ω     59.00 120.00   0.50    0.10    --   49.37 178.00   0.00  122
 55  ω     40.00 110.00   0.50    0.14    --  110.00 -99.00-150.00  140
 56  ω     40.00 110.00   0.50    0.14    --  110.00 -99.00-180.00  140
 57  ω     40.00 110.00   0.50    0.14    --  110.00 -99.00 -90.00  140
 58  ω     39.00 122.00   0.50    0.14    --  110.00-125.00-180.00  166
 59  ω     40.00 110.00   0.50    0.14    --  110.00 -99.00 -60.00  140
 60  ω     40.00 110.00   0.50    0.14    --  110.00 -99.00  30.00  140
 61  ω     40.00 110.00   0.50    0.14    --  110.00 -99.00  90.00  140
 62  ω   -121.00 -33.00   0.50    0.10    --  -54.00 -71.00 130.59  176
 63  ω   -125.00 -36.00   0.50    0.10    --  -58.00 -73.00-131.44  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3576
_reflns_number_total             3694
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.8921
_refine_diff_density_min         -1.3032
_refine_diff_density_rms         0.1262
_refine_ls_d_res_high            0.7832
_refine_ls_d_res_low             13.1597
_refine_ls_goodness_of_fit_ref   1.0775
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.0773
_refine_ls_shift/su_max          0.0013
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+2.2325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0690
_olex2_refinement_description    
;
;
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_refinement_flags_posn
I1 I 0.63809(2) 0.55521(3) 0.634517(14) 0.01801(7) Uani 1.000000 .
Br1 Br -0.05914(6) -0.26210(6) 0.92105(3) 0.04022(13) Uani 1.000000 .
Cl1 Cl 0.69951(10) 0.64491(10) 0.42360(6) 0.02111(17) Uani 1.000000 .
F4 F 0.6056(3) 0.6516(3) 0.83067(16) 0.0279(5) Uani 1.000000 .
F3 F 0.7494(3) 0.4162(3) 0.84125(16) 0.0296(5) Uani 1.000000 .
F2 F 0.3192(3) 0.5137(3) 0.82327(18) 0.0302(5) Uani 1.000000 .
F1 F 0.4470(3) 0.3627(3) 0.94946(15) 0.0329(5) Uani 1.000000 .
O1 O 0.4587(3) 0.2754(3) 0.80695(18) 0.0227(5) Uani 1.000000 .
O2 O 0.6195(3) 1.1375(3) 0.6140(2) 0.0310(6) Uani 1.000000 D
H2 H 0.516(4) 1.189(6) 0.605(4) 0.0465(9) Uiso 1.000000 DR
O3 O 0.4939(3) 0.9004(4) 0.6254(3) 0.0460(9) Uani 1.000000 .
C14 C 0.7927(4) 0.8952(4) 0.6282(2) 0.0177(6) Uani 1.000000 .
C1 C 0.1000(5) -0.0898(5) 0.8911(3) 0.0268(8) Uani 1.000000 .
C11 C 1.1234(4) 0.7589(5) 0.6295(3) 0.0235(7) Uani 1.000000 .
H3 H 1.2332(4) 0.7145(5) 0.6285(3) 0.0282(9) Uiso 1.000000 R
C4 C 0.3302(4) 0.1548(5) 0.8406(3) 0.0222(7) Uani 1.000000 .
C8 C 0.6137(4) 0.5058(5) 0.8033(3) 0.0219(7) Uani 1.000000 .
C10 C 0.9888(4) 0.6567(5) 0.6303(3) 0.0213(7) Uani 1.000000 .
H6 H 1.0079(4) 0.5440(5) 0.6309(3) 0.0256(8) Uiso 1.000000 R
C5 C 0.1636(5) 0.2001(5) 0.8257(3) 0.0258(8) Uani 1.000000 .
H7 H 0.1307(5) 0.3117(5) 0.7983(3) 0.0310(9) Uiso 1.000000 R
C13 C 0.9307(4) 0.9930(5) 0.6286(3) 0.0202(7) Uani 1.000000 .
H8 H 0.9123(4) 1.1058(5) 0.6278(3) 0.0242(8) Uiso 1.000000 R
C7 C 0.4540(5) 0.4085(5) 0.8468(3) 0.0224(7) Uani 1.000000 .
C9 C 0.8275(4) 0.7267(4) 0.6301(2) 0.0184(7) Uani 1.000000 .
C12 C 1.0933(4) 0.9250(5) 0.6301(3) 0.0229(7) Uani 1.000000 .
H11 H 1.1826(4) 0.9917(5) 0.6315(3) 0.0275(9) Uiso 1.000000 R
C3 C 0.3842(5) -0.0078(5) 0.8801(3) 0.0262(8) Uani 1.000000 .
H12 H 0.4974(5) -0.0339(5) 0.8893(3) 0.0314(9) Uiso 1.000000 R
C15 C 0.6192(4) 0.9778(5) 0.6219(3) 0.0233(7) Uani 1.000000 .
C6 C 0.0466(5) 0.0746(5) 0.8528(3) 0.0283(8) Uani 1.000000 .
H14 H -0.0670(5) 0.1012(5) 0.8452(3) 0.0340(10) Uiso 1.000000 R
C2 C 0.2662(5) -0.1339(5) 0.9063(3) 0.0302(8) Uani 1.000000 .
H15 H 0.2992(5) -0.2454(5) 0.9336(3) 0.0362(10) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cl1 2.7865(8) . ?
I1 C8 2.229(3) . ?
I1 C9 2.117(3) . ?
Br1 C1 1.898(3) . ?
F4 C8 1.345(4) . ?
F3 C8 1.344(4) . ?
F2 C7 1.352(5) . ?
F1 C7 1.352(4) . ?
O1 C4 1.428(4) . ?
O1 C7 1.344(4) . ?
O2 H2 0.911(19) . ?
O2 C15 1.292(5) . ?
O3 C15 1.209(4) . ?
C14 C13 1.405(4) . ?
C14 C9 1.393(5) . ?
C14 C15 1.507(5) . ?
C1 C6 1.376(6) . ?
C1 C2 1.376(6) . ?
C11 H3 0.9300 . ?
C11 C10 1.402(5) . ?
C11 C12 1.377(6) . ?
C4 C5 1.381(5) . ?
C4 C3 1.368(6) . ?
C8 C7 1.531(5) . ?
C10 H6 0.9300 . ?
C10 C9 1.380(5) . ?
C5 H7 0.9300 . ?
C5 C6 1.388(5) . ?
C13 H8 0.9300 . ?
C13 C12 1.384(5) . ?
C12 H11 0.9300 . ?
C3 H12 0.9300 . ?
C3 C2 1.396(5) . ?
C6 H14 0.9300 . ?
C2 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 I1 Cl1 172.85(9) . . ?
C9 I1 Cl1 84.68(9) . . ?
C9 I1 C8 88.16(12) . . ?
C7 O1 C4 119.1(3) . . ?
C15 O2 H2 113(3) . . ?
C9 C14 C13 116.8(3) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 C9 124.1(3) . . ?
C6 C1 Br1 119.1(3) . . ?
C2 C1 Br1 118.8(3) . . ?
C2 C1 C6 122.0(3) . . ?
C10 C11 H3 119.9(2) . . ?
C12 C11 H3 119.9(2) . . ?
C12 C11 C10 120.1(3) . . ?
C5 C4 O1 120.9(3) . . ?
C3 C4 O1 116.0(3) . . ?
C3 C4 C5 122.8(3) . . ?
F4 C8 I1 110.3(2) . . ?
F3 C8 I1 109.7(2) . . ?
F3 C8 F4 107.8(3) . . ?
C7 C8 I1 109.4(2) . . ?
C7 C8 F4 109.5(3) . . ?
C7 C8 F3 110.0(3) . . ?
H6 C10 C11 120.7(2) . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 H6 120.7(2) . . ?
H7 C5 C4 120.9(2) . . ?
C6 C5 C4 118.2(4) . . ?
C6 C5 H7 120.9(2) . . ?
H8 C13 C14 119.3(2) . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 H8 119.3(2) . . ?
F1 C7 F2 105.8(3) . . ?
O1 C7 F2 113.2(3) . . ?
O1 C7 F1 112.5(3) . . ?
C8 C7 F2 108.4(3) . . ?
C8 C7 F1 109.9(3) . . ?
C8 C7 O1 107.1(3) . . ?
C14 C9 I1 123.1(2) . . ?
C10 C9 I1 114.1(3) . . ?
C10 C9 C14 122.8(3) . . ?
C13 C12 C11 120.2(3) . . ?
H11 C12 C11 119.9(2) . . ?
H11 C12 C13 119.9(2) . . ?
H12 C3 C4 120.6(2) . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H12 120.6(3) . . ?
O3 C15 O2 124.3(4) . . ?
C14 C15 O2 113.0(3) . . ?
C14 C15 O3 122.8(3) . . ?
C5 C6 C1 119.4(4) . . ?
H14 C6 C1 120.3(2) . . ?
H14 C6 C5 120.3(2) . . ?
C3 C2 C1 118.7(4) . . ?
H15 C2 C1 120.6(2) . . ?
H15 C2 C3 120.6(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
- Detector area scaling
;
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O2 H2 1 0.9300 0.0200 0.0186

