# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_lac250219_1_1
_database_code_depnum_ccdc_archive 'CCDC 1913138'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_audit_creation_date             2019-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(4-Bromo-8-fluoro-5,6,7,8-tetrahydronaphthalen-1-yl)difluoro-λ3-iodane
_chemical_formula_moiety         'C10 H9 Br F3 I'
_chemical_formula_sum            'C10 H9 Br F3 I'
_chemical_formula_weight         392.98
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H9BrF3I
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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.483(2)
_cell_length_b                   8.4119(3)
_cell_length_c                   15.9818(15)
_cell_angle_alpha                90
_cell_angle_beta                 134.610(17)
_cell_angle_gamma                90
_cell_volume                     2247.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7333
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      77.7190
_cell_measurement_theta_min      5.5340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    26.661
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.086
_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    2.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -3 5 0.0516
-5 3 5 0.0549
5 -2 -5 0.0455
1 0 -1 0.0507
1 5 0 0.0556
1 0 0 0.0072
-1 0 0 0.0072
-3 -1 5 0.0536
-1 1 -4 0.0400
2 -2 -5 0.0382

_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.014
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
-6.0003 -3.0000 5.0002 -0.0619 0.2552 0.6865
-4.9996 3.0000 4.9997 0.2913 -0.6500 0.1642
4.9997 -2.0000 -4.9998 -0.2186 0.5058 -0.2507
1.0000 -0.0000 -1.0000 -0.0146 0.0435 -0.0848
1.0005 5.0000 -0.0005 0.2805 -0.7610 -0.4358
1.0000 0.0000 -0.0000 -0.0829 -0.0400 -0.0031
-1.0000 -0.0000 0.0000 0.0829 0.0400 0.0031
-3.0000 -1.0000 5.0000 -0.1653 -0.1532 0.5043
-1.0000 1.0000 -4.0000 0.4288 0.2298 -0.4103
1.9997 -2.0000 -4.9997 0.0302 0.6259 -0.2416

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11254
_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         78.444
_diffrn_reflns_theta_min         5.292
_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 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 170.00   0.50    1.10    --  105.75  77.00  90.00  172
  2  ω     84.00 170.00   0.50    1.10    --  105.75  77.00   0.00  172
  3  ω     92.00 176.00   0.50    1.10    --  105.75  57.00 -30.00  168
  4  ω     98.00 178.00   0.50    1.10    --  105.75  38.00 -60.00  160
  5  ω     98.00 178.00   0.50    1.10    --  105.75  38.00-120.00  160
  6  ω     98.00 178.00   0.50    1.10    --  105.75  38.00-180.00  160
  7  ω    -68.00  20.00   0.50    0.27    --    0.88   0.00-180.00  176
  8  ω    -83.00   1.00   0.50    1.10    --  -70.00  57.00  30.00  168
  9  ω    -22.00  64.00   0.50    0.27    --   -0.88  77.00 120.00  172
 10  ω     38.00 111.00   0.50    1.10    --  105.75 -99.00  60.00  146
 11  ω     41.00 127.00   0.50    1.10    --  105.75 -77.00-120.00  172
 12  ω     35.00 119.00   0.50    1.10    --  105.75 -57.00-120.00  168
 13  ω     35.00 119.00   0.50    1.10    --  105.75 -57.00  90.00  168
 14  ω    -69.00  14.00   0.50    0.27    --    0.88 -57.00   0.00  166
 15  ω    -75.00   8.00   0.50    0.27    --   -0.88 -19.00  30.00  166
 16  ω   -134.00 -48.00   0.50    1.10    --  -70.00 -77.00  90.00  172
 17  ω   -140.00 -66.00   0.50    1.10    --  -70.00-130.00 169.00  148
 18  ω   -134.00 -62.00   0.50    1.10    --  -70.00 -77.00-180.00  144
;
_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      -0.0829433000
_diffrn_orient_matrix_UB_12      0.0726918000
_diffrn_orient_matrix_UB_13      -0.0682971000
_diffrn_orient_matrix_UB_21      -0.0400031000
_diffrn_orient_matrix_UB_22      -0.1442049000
_diffrn_orient_matrix_UB_23      -0.0834916000
_diffrn_orient_matrix_UB_31      -0.0030605000
_diffrn_orient_matrix_UB_32      -0.0865388000
_diffrn_orient_matrix_UB_33      0.0817089000
_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                2271
_reflns_number_total             2383
_reflns_odcompleteness_completeness 99.95
_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         0.981
_refine_diff_density_min         -1.493
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.090
_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)+(0.0453P)²+12.0548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          
'Disorder in the hexy ring and attached fluorine.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C9-C8 \\sim C9A-C8A
 with sigma of 0.02
 C8A-C7 \\sim C8-C7
 with sigma of 0.02
 F3A-C10A \\sim F3-C10
 with sigma of 0.02
 C6-C10 \\sim C6-C10A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F3, F3A, C5, C6, C7, C8, C8A, C9, C9A, C10, C10A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F3A)=Sof(H7BC)=Sof(H7BD)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(F3)=Sof(H7AA)=Sof(H7AB)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(C10)=Sof(H10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C10A(H10A)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C8(H8A,H8B), C8A(H8AA,H8AB), C9(H9A,H9B),
 C9A(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.77157(2) 0.40684(3) 0.61519(3) 0.03196(11) Uani 1 1 d . . . . .
Br1 Br 0.52110(3) 0.64557(6) 0.65890(5) 0.03738(14) Uani 1 1 d . . . . .
F1 F 0.8486(2) 0.5650(5) 0.7416(3) 0.0619(10) Uani 1 1 d . . . . .
F2 F 0.68314(19) 0.2624(4) 0.4880(3) 0.0517(8) Uani 1 1 d . . . . .
F3 F 0.6220(4) 0.6385(7) 0.3950(5) 0.0386(16) Uani 0.513(8) 1 d D U P A 1
F3A F 0.7207(4) 0.7786(8) 0.5464(6) 0.0431(18) Uani 0.487(8) 1 d D U P A 2
C1 C 0.6912(2) 0.4866(5) 0.6238(4) 0.0267(8) Uani 1 1 d . . . . .
C2 C 0.6863(3) 0.3968(5) 0.6905(5) 0.0354(10) Uani 1 1 d . . . . .
H2 H 0.716839 0.305228 0.728367 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6346(3) 0.4465(6) 0.6998(4) 0.0349(10) Uani 1 1 d . . . . .
H3 H 0.629518 0.388573 0.743817 0.042 Uiso 1 1 calc R . . . .
C4 C 0.5910(3) 0.5831(5) 0.6426(4) 0.0289(9) Uani 1 1 d . . . . .
C5 C 0.5948(3) 0.6753(5) 0.5738(4) 0.0272(8) Uani 1 1 d . U . . .
C6 C 0.6469(3) 0.6235(5) 0.5646(4) 0.0249(8) Uani 1 1 d D U . . .
C7 C 0.5447(3) 0.8228(6) 0.5122(5) 0.0381(11) Uani 1 1 d D U . . .
H7AA H 0.569813 0.909630 0.568193 0.046 Uiso 0.513(8) 1 calc R . P A 1
H7AB H 0.492475 0.804664 0.482789 0.046 Uiso 0.513(8) 1 calc R . P A 1
H7BC H 0.548925 0.886777 0.566806 0.046 Uiso 0.487(8) 1 calc R . P A 2
H7BD H 0.489124 0.792712 0.447914 0.046 Uiso 0.487(8) 1 calc R . P A 2
C8 C 0.5345(7) 0.8704(15) 0.4097(10) 0.041(2) Uani 0.513(8) 1 d D U P A 1
H8A H 0.503575 0.790619 0.348235 0.049 Uiso 0.513(8) 1 calc R . P A 1
H8B H 0.506690 0.971322 0.376987 0.049 Uiso 0.513(8) 1 calc R . P A 1
C8A C 0.5714(9) 0.9233(14) 0.4634(14) 0.047(3) Uani 0.487(8) 1 d D U P A 2
H8AA H 0.532276 1.005540 0.411576 0.056 Uiso 0.487(8) 1 calc R . P A 2
H8AB H 0.622402 0.973878 0.527524 0.056 Uiso 0.487(8) 1 calc R . P A 2
C9 C 0.6183(7) 0.8840(12) 0.4583(11) 0.040(2) Uani 0.513(8) 1 d D U P A 1
H9A H 0.614499 0.925049 0.397792 0.048 Uiso 0.513(8) 1 calc R . P A 1
H9B H 0.650090 0.957709 0.523854 0.048 Uiso 0.513(8) 1 calc R . P A 1
C9A C 0.5791(8) 0.8134(17) 0.3963(11) 0.050(3) Uani 0.487(8) 1 d D U P A 2
H9AA H 0.529650 0.754851 0.337797 0.060 Uiso 0.487(8) 1 calc R . P A 2
H9AB H 0.588323 0.876061 0.355748 0.060 Uiso 0.487(8) 1 calc R . P A 2
C10 C 0.6580(10) 0.7247(17) 0.4981(14) 0.028(3) Uani 0.513(8) 1 d D U P A 1
H10 H 0.715210 0.737888 0.545739 0.034 Uiso 0.513(8) 1 calc R . P A 1
C10A C 0.6467(10) 0.699(2) 0.4778(14) 0.033(4) Uani 0.487(8) 1 d D U P A 2
H10A H 0.643349 0.615393 0.431786 0.039 Uiso 0.487(8) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 F1 1.998(3) . ?
I1 F2 1.998(3) . ?
I1 C1 2.097(4) . ?
Br1 C4 1.908(4) . ?
F3 C10 1.414(17) . ?
F3A C10A 1.411(18) . ?
C1 C2 1.375(6) . ?
C1 C6 1.386(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(6) . ?
C4 C5 1.398(6) . ?
C5 C6 1.400(6) . ?
C5 C7 1.505(6) . ?
C6 C10 1.520(11) . ?
C6 C10A 1.523(11) . ?
C7 H7AA 0.9700 . ?
C7 H7AB 0.9700 . ?
C7 H7BC 0.9700 . ?
C7 H7BD 0.9700 . ?
C7 C8 1.531(11) . ?
C7 C8A 1.549(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.531(13) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.520(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.495(13) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.496(14) . ?
C10 H10 0.9800 . ?
C10A H10A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 I1 F2 171.88(12) . . ?
F1 I1 C1 86.46(15) . . ?
F2 I1 C1 85.48(14) . . ?
C2 C1 I1 116.4(3) . . ?
C2 C1 C6 123.7(4) . . ?
C6 C1 I1 120.0(3) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 Br1 116.7(3) . . ?
C3 C4 C5 123.9(4) . . ?
C5 C4 Br1 119.4(3) . . ?
C4 C5 C6 116.9(4) . . ?
C4 C5 C7 121.3(4) . . ?
C6 C5 C7 121.7(4) . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 C10 121.9(6) . . ?
C1 C6 C10A 119.3(7) . . ?
C5 C6 C10 119.4(6) . . ?
C5 C6 C10A 121.5(7) . . ?
C5 C7 H7AA 109.1 . . ?
C5 C7 H7AB 109.1 . . ?
C5 C7 H7BC 109.2 . . ?
C5 C7 H7BD 109.2 . . ?
C5 C7 C8 112.3(5) . . ?
C5 C7 C8A 111.9(5) . . ?
H7AA C7 H7AB 107.9 . . ?
H7BC C7 H7BD 107.9 . . ?
C8 C7 H7AA 109.1 . . ?
C8 C7 H7AB 109.1 . . ?
C8A C7 H7BC 109.2 . . ?
C8A C7 H7BD 109.2 . . ?
C7 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 C7 107.2(8) . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C7 C8A H8AA 110.0 . . ?
C7 C8A H8AB 110.0 . . ?
H8AA C8A H8AB 108.4 . . ?
C9A C8A C7 108.3(9) . . ?
C9A C8A H8AA 110.0 . . ?
C9A C8A H8AB 110.0 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.1(10) . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 108.1 . . ?
C10A C9A C8A 110.8(12) . . ?
C10A C9A H9AA 109.5 . . ?
C10A C9A H9AB 109.5 . . ?
F3 C10 C6 105.8(10) . . ?
F3 C10 C9 106.3(11) . . ?
F3 C10 H10 109.5 . . ?
C6 C10 H10 109.5 . . ?
C9 C10 C6 115.9(10) . . ?
C9 C10 H10 109.5 . . ?
F3A C10A C6 106.0(11) . . ?
F3A C10A C9A 110.2(12) . . ?
F3A C10A H10A 109.3 . . ?
C6 C10A H10A 109.3 . . ?
C9A C10A C6 112.6(10) . . ?
C9A C10A H10A 109.3 . . ?

_olex2_submission_original_sample_id lac250219_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.603
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/n-hexane'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ep_6041
_database_code_depnum_ccdc_archive 'CCDC 1913140'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_audit_creation_date             2019-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1,1,1-Trifluoro-3,3-dimethyl-1,3-dihydro-1λ5-benzo[d][1,2]iodaoxole
_chemical_formula_moiety         'C9 H10 F3 I O'
_chemical_formula_sum            'C9 H10 F3 I O'
_chemical_formula_weight         318.07
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   15.2690(11)
_cell_length_b                   10.8007(9)
_cell_length_c                   13.7770(11)
_cell_angle_alpha                90
_cell_angle_beta                 116.7259(14)
_cell_angle_gamma                90
_cell_volume                     2029.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    3.164
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.025
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33393
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.619
_diffrn_reflns_theta_min         1.493
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4966
_reflns_number_total             6167
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         2.825
_refine_diff_density_min         -2.298
_refine_diff_density_rms         0.258
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         6167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      0.989
_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)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          
'Twinned sample, refined with TWIN + BASF instructions.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5648
 0.4352
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B)
3.b Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,
 H9BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 0.16113(4) 0.24397(10) 0.49560(5) 0.00950(10) Uani 1 1 d . . . . .
F1A F 0.1490(3) 0.3123(4) 0.6218(3) 0.0197(10) Uani 1 1 d . . . . .
F2A F 0.1376(3) 0.0783(4) 0.5397(4) 0.0201(10) Uani 1 1 d . . . . .
F3A F 0.1516(3) 0.1566(4) 0.3668(4) 0.0172(9) Uani 1 1 d . . . . .
O1A O 0.1550(3) 0.4010(4) 0.4267(4) 0.0139(11) Uani 1 1 d . . . . .
C1A C 0.0094(5) 0.2599(6) 0.4169(8) 0.0121(14) Uani 1 1 d . . . . .
C2A C -0.0549(4) 0.1797(6) 0.4318(5) 0.0139(13) Uani 1 1 d . . . . .
H2A H -0.031855 0.108935 0.477216 0.017 Uiso 1 1 calc R . . . .
C3A C -0.1539(5) 0.2075(6) 0.3776(7) 0.0192(15) Uani 1 1 d . . . . .
H3A H -0.200169 0.155034 0.385559 0.023 Uiso 1 1 calc R . . . .
C4A C -0.1856(5) 0.3101(7) 0.3125(6) 0.0174(14) Uani 1 1 d . . . . .
H4A H -0.253779 0.327303 0.275119 0.021 Uiso 1 1 calc R . . . .
C5A C -0.1185(5) 0.3908(6) 0.3000(5) 0.0159(15) Uani 1 1 d . . . . .
H5A H -0.141197 0.461873 0.254859 0.019 Uiso 1 1 calc R . . . .
C6A C -0.0187(5) 0.3647(6) 0.3549(5) 0.0134(14) Uani 1 1 d . . . . .
C7A C 0.0600(4) 0.4441(5) 0.3455(5) 0.0117(13) Uani 1 1 d . . . . .
C8A C 0.0503(5) 0.5811(5) 0.3699(6) 0.0171(14) Uani 1 1 d . . . . .
H8AA H -0.013969 0.612350 0.317551 0.026 Uiso 1 1 calc GR . . . .
H8AB H 0.102039 0.629349 0.364043 0.026 Uiso 1 1 calc GR . . . .
H8AC H 0.056617 0.588697 0.443657 0.026 Uiso 1 1 calc GR . . . .
C9A C 0.0575(5) 0.4293(6) 0.2339(6) 0.0182(15) Uani 1 1 d . . . . .
H9AA H -0.003565 0.464391 0.178011 0.027 Uiso 1 1 calc GR . . . .
H9AB H 0.061104 0.341257 0.218986 0.027 Uiso 1 1 calc GR . . . .
H9AC H 0.113541 0.472930 0.233171 0.027 Uiso 1 1 calc GR . . . .
I1B I 0.33679(4) 0.22757(3) 0.33169(4) 0.01152(11) Uani 1 1 d . . . . .
F1B F 0.3561(3) 0.1501(4) 0.2139(3) 0.0209(10) Uani 1 1 d . . . . .
F2B F 0.3695(3) 0.0615(3) 0.4004(3) 0.0228(10) Uani 1 1 d . . . . .
F3B F 0.3452(3) 0.2916(4) 0.4688(3) 0.0176(8) Uani 1 1 d . . . . .
O1B O 0.3314(3) 0.3879(4) 0.2688(4) 0.0163(11) Uani 1 1 d . . . . .
C1B C 0.4859(5) 0.2612(5) 0.4006(7) 0.0133(15) Uani 1 1 d . . . . .
C2B C 0.5563(5) 0.1839(6) 0.4765(5) 0.0164(14) Uani 1 1 d . . . . .
H2B H 0.538550 0.110276 0.501001 0.020 Uiso 1 1 calc R . . . .
C3B C 0.6543(5) 0.2193(6) 0.5152(6) 0.0183(15) Uani 1 1 d . . . . .
H3B H 0.704867 0.169285 0.567017 0.022 Uiso 1 1 calc R . . . .
C4B C 0.6779(5) 0.3285(6) 0.4775(6) 0.0222(16) Uani 1 1 d . . . . .
H4B H 0.744727 0.351243 0.502931 0.027 Uiso 1 1 calc R . . . .
C5B C 0.6056(5) 0.4034(6) 0.4041(6) 0.0209(16) Uani 1 1 d . . . . .
H5B H 0.622930 0.478422 0.381200 0.025 Uiso 1 1 calc R . . . .
C6B C 0.5068(5) 0.3702(5) 0.3629(5) 0.0117(13) Uani 1 1 d . . . . .
C7B C 0.4230(5) 0.4441(6) 0.2803(6) 0.0162(14) Uani 1 1 d . . . . .
C8B C 0.4246(5) 0.4380(7) 0.1706(6) 0.0226(16) Uani 1 1 d . . . . .
H8BA H 0.415539 0.352061 0.145101 0.034 Uiso 1 1 calc GR . . . .
H8BB H 0.487830 0.468719 0.178278 0.034 Uiso 1 1 calc GR . . . .
H8BC H 0.371649 0.489311 0.117942 0.034 Uiso 1 1 calc GR . . . .
C9B C 0.4243(5) 0.5762(6) 0.3191(6) 0.0219(17) Uani 1 1 d . . . . .
H9BA H 0.368991 0.622245 0.264000 0.033 Uiso 1 1 calc GR . . . .
H9BB H 0.485896 0.616234 0.331157 0.033 Uiso 1 1 calc GR . . . .
H9BC H 0.418722 0.575106 0.387296 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1A F1A 1.972(4) . ?
I1A F2A 1.974(4) . ?
I1A F3A 1.956(4) . ?
I1A O1A 1.925(5) . ?
I1A C1A 2.076(7) . ?
O1A C7A 1.454(7) . ?
C1A C2A 1.393(10) . ?
C1A C6A 1.365(10) . ?
C2A C3A 1.384(9) . ?
C3A C4A 1.369(10) . ?
C4A C5A 1.413(10) . ?
C5A C6A 1.392(9) . ?
C6A C7A 1.528(9) . ?
C7A C8A 1.539(8) . ?
C7A C9A 1.529(9) . ?
I1B F1B 1.963(4) . ?
I1B F2B 1.984(4) . ?
I1B F3B 1.961(4) . ?
I1B O1B 1.922(4) . ?
I1B C1B 2.068(7) . ?
O1B C7B 1.465(8) . ?
C1B C2B 1.391(10) . ?
C1B C6B 1.381(9) . ?
C2B C3B 1.396(10) . ?
C3B C4B 1.400(10) . ?
C4B C5B 1.375(9) . ?
C5B C6B 1.398(9) . ?
C6B C7B 1.504(9) . ?
C7B C8B 1.524(10) . ?
C7B C9B 1.521(9) . ?

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
F1A I1A F2A 88.00(19) . . ?
F1A I1A C1A 84.5(3) . . ?
F2A I1A C1A 85.5(2) . . ?
F3A I1A F1A 168.99(16) . . ?
F3A I1A F2A 83.85(19) . . ?
F3A I1A C1A 87.5(3) . . ?
O1A I1A F1A 95.8(2) . . ?
O1A I1A F2A 167.20(18) . . ?
O1A I1A F3A 90.6(2) . . ?
O1A I1A C1A 82.7(2) . . ?
C7A O1A I1A 118.2(3) . . ?
C2A C1A I1A 124.5(6) . . ?
C6A C1A I1A 111.0(5) . . ?
C6A C1A C2A 124.3(6) . . ?
C3A C2A C1A 117.2(6) . . ?
C4A C3A C2A 120.4(7) . . ?
C3A C4A C5A 121.1(6) . . ?
C6A C5A C4A 119.0(6) . . ?
C1A C6A C5A 117.9(6) . . ?
C1A C6A C7A 118.7(6) . . ?
C5A C6A C7A 123.4(6) . . ?
O1A C7A C6A 107.8(5) . . ?
O1A C7A C8A 107.4(5) . . ?
O1A C7A C9A 107.8(5) . . ?
C6A C7A C8A 111.4(5) . . ?
C6A C7A C9A 111.2(5) . . ?
C9A C7A C8A 111.0(5) . . ?
F1B I1B F2B 84.83(18) . . ?
F1B I1B C1B 84.9(3) . . ?
F2B I1B C1B 87.2(2) . . ?
F3B I1B F1B 167.94(17) . . ?
F3B I1B F2B 88.03(17) . . ?
F3B I1B C1B 85.1(3) . . ?
O1B I1B F1B 90.18(18) . . ?
O1B I1B F2B 168.61(19) . . ?
O1B I1B F3B 95.04(19) . . ?
O1B I1B C1B 82.2(2) . . ?
C7B O1B I1B 118.6(4) . . ?
C2B C1B I1B 124.0(5) . . ?
C6B C1B I1B 111.7(5) . . ?
C6B C1B C2B 124.3(7) . . ?
C1B C2B C3B 117.1(6) . . ?
C2B C3B C4B 120.0(6) . . ?
C5B C4B C3B 120.8(6) . . ?
C4B C5B C6B 120.7(7) . . ?
C1B C6B C5B 117.1(6) . . ?
C1B C6B C7B 118.3(6) . . ?
C5B C6B C7B 124.6(6) . . ?
O1B C7B C6B 108.0(5) . . ?
O1B C7B C8B 108.4(5) . . ?
O1B C7B C9B 106.7(5) . . ?
C6B C7B C8B 109.9(6) . . ?
C6B C7B C9B 111.0(6) . . ?
C9B C7B C8B 112.7(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1A O1A C7A C6A 14.0(6) . . . . ?
I1A O1A C7A C8A 134.2(5) . . . . ?
I1A O1A C7A C9A -106.1(5) . . . . ?
I1A C1A C2A C3A 176.4(6) . . . . ?
I1A C1A C6A C5A -177.7(5) . . . . ?
I1A C1A C6A C7A 4.7(9) . . . . ?
C1A C2A C3A C4A -0.1(12) . . . . ?
C1A C6A C7A O1A -11.8(8) . . . . ?
C1A C6A C7A C8A -129.4(7) . . . . ?
C1A C6A C7A C9A 106.1(7) . . . . ?
C2A C1A C6A C5A -2.3(12) . . . . ?
C2A C1A C6A C7A -179.9(7) . . . . ?
C2A C3A C4A C5A -0.8(12) . . . . ?
C3A C4A C5A C6A 0.2(11) . . . . ?
C4A C5A C6A C1A 1.3(10) . . . . ?
C4A C5A C6A C7A 178.8(6) . . . . ?
C5A C6A C7A O1A 170.8(6) . . . . ?
C5A C6A C7A C8A 53.1(8) . . . . ?
C5A C6A C7A C9A -71.3(8) . . . . ?
C6A C1A C2A C3A 1.6(12) . . . . ?
I1B O1B C7B C6B -12.1(7) . . . . ?
I1B O1B C7B C8B 106.8(5) . . . . ?
I1B O1B C7B C9B -131.6(5) . . . . ?
I1B C1B C2B C3B 179.8(5) . . . . ?
I1B C1B C6B C5B 179.7(5) . . . . ?
I1B C1B C6B C7B -0.9(9) . . . . ?
C1B C2B C3B C4B 0.1(11) . . . . ?
C1B C6B C7B O1B 7.9(8) . . . . ?
C1B C6B C7B C8B -110.1(7) . . . . ?
C1B C6B C7B C9B 124.5(7) . . . . ?
C2B C1B C6B C5B 0.4(12) . . . . ?
C2B C1B C6B C7B 179.7(7) . . . . ?
C2B C3B C4B C5B 1.3(12) . . . . ?
C3B C4B C5B C6B -1.9(12) . . . . ?
C4B C5B C6B C1B 1.1(11) . . . . ?
C4B C5B C6B C7B -178.2(7) . . . . ?
C5B C6B C7B O1B -172.8(6) . . . . ?
C5B C6B C7B C8B 69.2(8) . . . . ?
C5B C6B C7B C9B -56.2(9) . . . . ?
C6B C1B C2B C3B -0.9(12) . . . . ?

_olex2_date_sample_data_collection 2014-09-25
_olex2_date_sample_submission    2014-09-25
_olex2_submission_original_sample_id ep_6041
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5648
2 0.4352

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_lac130219_1_1
_database_code_depnum_ccdc_archive 'CCDC 1913139'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_audit_creation_date             2019-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Tetrafluoro(4-fluorophenyl)-λ5-iodane
_chemical_formula_moiety         'C6 H4 F5 I'
_chemical_formula_sum            'C6 H4 F5 I'
_chemical_formula_weight         297.99
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H4F5I
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      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                   8.90830(10)
_cell_length_b                   6.03640(10)
_cell_length_c                   14.1452(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.6270(10)
_cell_angle_gamma                90
_cell_volume                     760.338(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7251
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.0690
_cell_measurement_theta_min      4.9720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    33.528
_exptl_absorpt_correction_T_max  0.430
_exptl_absorpt_correction_T_min  0.049
_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    2.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -3 -4 0.0585
2 1 -5 0.0716
-2 1 5 0.0524
-5 0 -1 0.0391
4 -3 0 0.0573
-2 -1 -1 0.0612
-4 3 0 0.0790
5 1 2 0.0099
-1 1 -5 0.0782
1 -2 -5 0.0654
1 -2 5 0.0617
0 1 5 0.0375
-2 4 -3 0.0922
1 3 -5 0.0819
-5 1 -4 0.0498
-3 -3 -5 0.0550

_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.061
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
2.0028 -2.9983 -4.0064 0.0845 -0.3454 0.8721
2.0001 1.0012 -4.9983 0.3022 -0.6087 -0.0958
-2.0015 0.9984 5.0024 -0.1843 0.5304 -0.3945
-5.0003 0.0002 -1.0007 -0.8513 -0.0166 -0.2010
4.0025 -2.9994 -0.0057 0.4899 0.0454 0.9066
-1.9993 -0.9995 -1.0024 -0.4103 -0.0315 0.1724
-4.0025 2.9994 0.0057 -0.4899 -0.0454 -0.9066
4.9994 0.9993 2.0029 0.9283 0.0842 -0.0569
-1.0001 1.0011 -4.9986 -0.1978 -0.5547 -0.2241
1.0022 -1.9982 -5.0046 -0.0412 -0.4732 0.5970
1.0008 -2.0009 4.9966 0.1389 0.5938 0.4693
-0.0014 0.9985 5.0026 0.1490 0.4944 -0.3090
-2.0026 4.0000 -2.9923 -0.1517 -0.4407 -1.0279
0.9986 3.0007 -4.9943 0.2533 -0.6690 -0.6289
-5.0006 1.0008 -3.9990 -0.8465 -0.3759 -0.4079
-2.9975 -2.9981 -5.0071 -0.7668 -0.3620 0.6711

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.316
_diffrn_reflns_theta_min         5.796
_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 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 125.00   0.50    0.40    --  105.75   0.00-120.00  178
  2  ω     98.00 178.00   0.50    0.40    --  105.75  38.00 -30.00  160
  3  ω     -7.00  75.00   0.50    0.10    --    0.88  38.00 -30.00  164
  4  ω     97.00 178.00   0.50    0.40    --  105.75  19.00  90.00  162
  5  ω     97.00 178.00   0.50    0.40    --  105.75  19.00  60.00  162
  6  ω     98.00 178.00   0.50    0.40    --  105.75  21.00  49.00  160
  7  ω     36.00 125.00   0.50    0.40    --  105.75   0.00 -30.00  178
  8  ω    -70.00  19.00   0.50    0.10    --   -0.88   0.00 150.00  178
  9  ω    -78.00   4.00   0.50    0.40    --  -70.00  38.00-120.00  164
 10  ω     35.00 119.00   0.50    0.40    --  105.75 -57.00-180.00  168
 11  ω    -63.00  22.00   0.50    0.10    --    0.88 -77.00 120.00  170
 12  ω     35.00 119.00   0.50    0.40    --  105.75 -57.00   0.00  168
 13  ω    -65.00  21.00   0.50    0.10    --   -0.88 -77.00  30.00  172
 14  ω   -134.00 -48.00   0.50    0.40    --  -70.00 -77.00-120.00  172
 15  ω   -134.00 -81.00   0.50    0.40    --  -70.00 -77.00   0.00  106
 16  ω   -138.00 -82.00   0.50    0.40    --  -70.00 -99.00 120.00  112
 17  ω     38.00 111.00   0.50    0.40    --  105.75 -99.00 150.00  146
 18  ω     35.00 121.00   0.50    0.40    --  105.75-125.00  30.00  172
 19  ω     38.00 111.00   0.50    0.40    --  105.75 -99.00-150.00  146
;
_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      0.1666482000
_diffrn_orient_matrix_UB_12      0.0590010000
_diffrn_orient_matrix_UB_13      0.0180524000
_diffrn_orient_matrix_UB_21      -0.0180299000
_diffrn_orient_matrix_UB_22      -0.0394035000
_diffrn_orient_matrix_UB_23      0.1066822000
_diffrn_orient_matrix_UB_31      0.0427579000
_diffrn_orient_matrix_UB_32      -0.2451731000
_diffrn_orient_matrix_UB_33      -0.0128282000
_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                1586
_reflns_number_total             1608
_reflns_odcompleteness_completeness 100.00
_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         0.808
_refine_diff_density_min         -1.573
_refine_diff_density_rms         0.163
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.141
_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)+(0.0532P)²+0.7739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0787
_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:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.64297(2) 0.65872(3) 0.67229(2) 0.01982(12) Uani 1 1 d . . . . .
F1 F 0.5944(2) 0.9496(4) 0.72486(15) 0.0265(4) Uani 1 1 d . . . . .
F2 F 0.5881(2) 0.5206(4) 0.79089(15) 0.0285(5) Uani 1 1 d . . . . .
F3 F 0.6548(3) 0.3670(4) 0.61978(19) 0.0338(5) Uani 1 1 d . . . . .
F4 F 0.6606(2) 0.7881(4) 0.54802(15) 0.0287(5) Uani 1 1 d . . . . .
F5 F -0.0324(3) 0.6325(5) 0.57776(19) 0.0358(6) Uani 1 1 d . . . . .
C1 C 0.4144(4) 0.6457(6) 0.6392(3) 0.0205(7) Uani 1 1 d . . . . .
C2 C 0.3496(4) 0.8291(6) 0.5956(3) 0.0250(8) Uani 1 1 d . . . . .
H2 H 0.406926 0.952718 0.581147 0.030 Uiso 1 1 calc R . . . .
C3 C 0.1959(5) 0.8231(7) 0.5740(3) 0.0284(9) Uani 1 1 d . . . . .
H3 H 0.147823 0.942133 0.544365 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1180(4) 0.6367(7) 0.5978(3) 0.0273(8) Uani 1 1 d . . . . .
C5 C 0.1820(4) 0.4524(7) 0.6401(3) 0.0281(8) Uani 1 1 d . . . . .
H5 H 0.124273 0.328859 0.653937 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3349(4) 0.4564(6) 0.6614(2) 0.0239(7) Uani 1 1 d . . . . .
H6 H 0.382634 0.335537 0.689748 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 F1 1.960(2) . ?
I1 F2 1.948(2) . ?
I1 F3 1.915(2) . ?
I1 F4 1.934(2) . ?
I1 C1 2.078(4) . ?
F5 C4 1.361(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.385(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(6) . ?
C4 C5 1.379(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 I1 C1 83.90(11) . . ?
F2 I1 F1 89.61(9) . . ?
F2 I1 C1 84.82(12) . . ?
F3 I1 F1 170.39(9) . . ?
F3 I1 F2 87.61(11) . . ?
F3 I1 F4 90.69(11) . . ?
F3 I1 C1 86.68(12) . . ?
F4 I1 F1 90.43(10) . . ?
F4 I1 F2 169.86(9) . . ?
F4 I1 C1 85.10(12) . . ?
C2 C1 I1 117.6(3) . . ?
C2 C1 C6 123.4(3) . . ?
C6 C1 I1 119.0(3) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.1(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3 121.0 . . ?
F5 C4 C3 117.8(4) . . ?
F5 C4 C5 117.9(4) . . ?
C3 C4 C5 124.3(3) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(4) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?

_olex2_submission_original_sample_id lac130219_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 1.961
_oxdiff_exptl_absorpt_empirical_full_min 0.597
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
_chemical_properties_physical    Moisture-sensitive
