# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_yoshi95m
_audit_block_doi                 10.5517/ccdc.csd.cc24hvtb
_database_code_depnum_ccdc_archive 'CCDC 1981452'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0SC02737E 2020
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_yoshi95m            
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.003 Check
RESPONSE: Checked. It is not caused by an omission or oversight
;
_vrf_PLAT911_yoshi95m            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
RESPONSE: Checked. It is not caused by an omission or oversight
;
_vrf_PLAT934_yoshi95m            
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
RESPONSE: Checked. It is not caused by an omission or oversight
;
# Added during the CSD deposition process: Monday 03 February 2020 02:03 AM
# end Validation Reply Form

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 F6 I N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         517.16

_chemical_melting_point          271-273

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5364(3)
_cell_length_b                   8.1598(3)
_cell_length_c                   14.6308(6)
_cell_angle_alpha                74.8246(15)
_cell_angle_beta                 86.9207(15)
_cell_angle_gamma                83.5890(14)
_cell_volume                     862.64(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7468
_cell_measurement_theta_min      2.5997
_cell_measurement_theta_max      31.4720
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500

_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.83

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            20823
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         33.80
_diffrn_reflns_theta_full        33.80
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_reflns_number_total             6892
_reflns_number_gt                5554
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0791
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         6892
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0148P)²+0.7450P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.770
_refine_diff_density_min         -1.134
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5841(4) 0.3201(3) 0.23384(18) 0.0160(5) Uani d . . . 1 . .
C C2 0.4802(3) 0.4691(3) 0.23941(18) 0.0166(5) Uani d . . . 1 . .
H H2 0.400367 0.470823 0.291741 0.02 Uiso calc U . R 1 . .
C C3 0.4960(4) 0.6151(3) 0.16662(19) 0.0187(5) Uani d . . . 1 . .
H H3 0.427705 0.719134 0.168942 0.022 Uiso calc U . R 1 . .
C C4 0.6119(4) 0.6088(4) 0.09028(19) 0.0203(5) Uani d . . . 1 . .
H H4 0.621256 0.708555 0.040023 0.024 Uiso calc U . R 1 . .
C C5 0.7145(4) 0.4580(4) 0.08663(19) 0.0192(5) Uani d . . . 1 . .
H H5 0.793483 0.455783 0.034026 0.023 Uiso calc U . R 1 . .
C C6 0.7026(4) 0.3097(3) 0.15957(18) 0.0162(5) Uani d . . . 1 . .
C C7 0.8108(4) 0.1369(3) 0.16156(18) 0.0167(5) Uani d . . . 1 . .
C C8 0.7583(4) 0.0735(4) 0.0774(2) 0.0225(6) Uani d . . . 1 . .
C C9 1.0122(4) 0.1589(4) 0.15599(19) 0.0210(6) Uani d . . . 1 . .
C C10 0.3793(4) 0.2079(3) 0.42896(18) 0.0158(5) Uani d . . . 1 . .
C C11 0.1977(3) 0.1838(3) 0.43380(18) 0.0159(5) Uani d . . . 1 . .
H H11 0.146078 0.132579 0.391699 0.019 Uiso calc U . R 1 . .
C C12 0.0989(3) 0.2396(3) 0.50396(18) 0.0144(5) Uani d . . . 1 . .
C C13 0.1734(3) 0.3122(3) 0.56713(17) 0.0124(4) Uani d . . . 1 . .
C C14 0.3519(3) 0.3369(3) 0.56214(18) 0.0155(5) Uani d . . . 1 . .
H H14 0.402095 0.388941 0.604347 0.019 Uiso calc U . R 1 . .
C C15 0.4552(3) 0.2815(3) 0.49175(18) 0.0160(5) Uani d . . . 1 . .
H H15 0.57941 0.29404 0.486446 0.019 Uiso calc U . R 1 . .
C C16 -0.1167(4) 0.2876(3) 0.60748(19) 0.0176(5) Uani d . . . 1 . .
C C17 0.0545(4) 0.3994(4) 0.71469(19) 0.0207(6) Uani d . . . 1 . .
H H17A -0.062233 0.407915 0.746921 0.031 Uiso calc U . R 1 . .
H H17B 0.100914 0.511295 0.697649 0.031 Uiso calc U . R 1 . .
H H17C 0.137589 0.31654 0.756999 0.031 Uiso calc U . R 1 . .
F F1 0.5838(2) 0.0510(2) 0.08540(14) 0.0347(4) Uani d . . . 1 . .
F F2 0.8472(3) -0.0766(2) 0.07548(12) 0.0282(4) Uani d . . . 1 . .
F F3 0.7840(3) 0.1803(2) -0.00754(12) 0.0280(4) Uani d . . . 1 . .
F F4 1.1133(2) 0.0105(2) 0.16745(13) 0.0308(4) Uani d . . . 1 . .
F F5 1.0676(2) 0.2620(2) 0.07499(12) 0.0283(4) Uani d . . . 1 . .
F F6 1.0529(3) 0.2264(3) 0.22571(13) 0.0346(5) Uani d . . . 1 . .
I I1 0.56286(2) 0.09166(2) 0.34153(2) 0.01746(5) Uani d . . . 1 . .
N N1 0.0357(3) 0.3437(3) 0.62921(15) 0.0150(4) Uani d . . . 1 . .
O O1 0.7790(3) 0.0157(3) 0.24262(14) 0.0267(5) Uani d . . . 1 . .
O O2 -0.0795(2) 0.2257(3) 0.52724(13) 0.0186(4) Uani d . . . 1 . .
O O3 -0.2617(3) 0.2882(3) 0.64531(15) 0.0240(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.383(4) ?
C1 C2 . 1.389(4) ?
C1 I1 . 2.118(3) ?
C2 C3 . 1.386(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.389(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.390(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.396(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.542(4) ?
C7 O1 . 1.360(3) ?
C7 C8 . 1.541(4) ?
C7 C9 . 1.543(4) ?
C8 F2 . 1.334(3) ?
C8 F3 . 1.336(3) ?
C8 F1 . 1.343(3) ?
C9 F4 . 1.333(3) ?
C9 F5 . 1.338(3) ?
C9 F6 . 1.343(3) ?
C10 C15 . 1.398(4) ?
C10 C11 . 1.400(4) ?
C10 I1 . 2.145(2) ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.95 ?
C12 O2 . 1.379(3) ?
C12 C13 . 1.392(3) ?
C13 C14 . 1.378(3) ?
C13 N1 . 1.389(3) ?
C14 C15 . 1.396(4) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 O3 . 1.198(3) ?
C16 N1 . 1.364(3) ?
C16 O2 . 1.399(3) ?
C17 N1 . 1.457(3) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
I1 O1 . 2.2633(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 123.5(2) ?
C6 C1 I1 . . 116.38(19) ?
C2 C1 I1 . . 120.12(19) ?
C3 C2 C1 . . 118.3(2) ?
C3 C2 H2 . . 120.9 ?
C1 C2 H2 . . 120.9 ?
C2 C3 C4 . . 119.8(2) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.6(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 117.1(2) ?
C1 C6 C7 . . 118.6(2) ?
C5 C6 C7 . . 124.2(2) ?
O1 C7 C6 . . 112.0(2) ?
O1 C7 C8 . . 108.0(2) ?
C6 C7 C8 . . 109.2(2) ?
O1 C7 C9 . . 107.7(2) ?
C6 C7 C9 . . 109.4(2) ?
C8 C7 C9 . . 110.6(2) ?
F2 C8 F3 . . 106.9(2) ?
F2 C8 F1 . . 107.0(2) ?
F3 C8 F1 . . 106.7(2) ?
F2 C8 C7 . . 112.1(2) ?
F3 C8 C7 . . 114.5(2) ?
F1 C8 C7 . . 109.2(2) ?
F4 C9 F5 . . 106.8(2) ?
F4 C9 F6 . . 106.6(2) ?
F5 C9 F6 . . 106.4(2) ?
F4 C9 C7 . . 112.2(2) ?
F5 C9 C7 . . 114.6(2) ?
F6 C9 C7 . . 109.7(2) ?
C15 C10 C11 . . 122.2(2) ?
C15 C10 I1 . . 116.15(19) ?
C11 C10 I1 . . 120.74(18) ?
C12 C11 C10 . . 115.3(2) ?
C12 C11 H11 . . 122.3 ?
C10 C11 H11 . . 122.3 ?
O2 C12 C11 . . 127.7(2) ?
O2 C12 C13 . . 109.3(2) ?
C11 C12 C13 . . 122.9(2) ?
C14 C13 N1 . . 132.1(2) ?
C14 C13 C12 . . 121.8(2) ?
N1 C13 C12 . . 106.1(2) ?
C13 C14 C15 . . 116.5(2) ?
C13 C14 H14 . . 121.8 ?
C15 C14 H14 . . 121.8 ?
C14 C15 C10 . . 121.3(2) ?
C14 C15 H15 . . 119.4 ?
C10 C15 H15 . . 119.4 ?
O3 C16 N1 . . 129.9(2) ?
O3 C16 O2 . . 122.2(2) ?
N1 C16 O2 . . 107.8(2) ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C1 I1 C10 . . 94.78(10) ?
C1 I1 O1 . . 76.58(8) ?
C10 I1 O1 . . 169.35(9) ?
C16 N1 C13 . . 109.6(2) ?
C16 N1 C17 . . 123.7(2) ?
C13 N1 C17 . . 125.9(2) ?
C7 O1 I1 . . 116.07(15) ?
C12 O2 C16 . . 107.09(19) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and hexane'
####################################################################### 
# 
# 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_ito123m
_database_code_depnum_ccdc_archive 'CCDC 2100970'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C84 H104 F24 I4 N4 O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         2261.31
_chemical_absolute_configuration ?

_chemical_melting_point          430

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9670(9)
_cell_length_b                   16.2018(14)
_cell_length_c                   13.8919(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.218(5)
_cell_angle_gamma                90
_cell_volume                     2243.3(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9046
_cell_measurement_theta_min      2.3991
_cell_measurement_theta_max      28.5276
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128

_exptl_absorpt_coefficient_mu    1.494
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            51158
_diffrn_reflns_av_R_equivalents  0.1105
_diffrn_reflns_av_unetI/netI     0.1603
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         32.11
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             15649
_reflns_number_gt                9720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0888
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.964
_refine_ls_number_reflns         15649
_refine_ls_number_parameters     570
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0152P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.066
_refine_diff_density_min         -1.577
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3316 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.056(15)

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 (Ver 2019.11, Bruker AXS Inc., 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Ver 2019.11, Bruker AXS Inc., 2020)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1913(7) 0.4415(5) 0.9527(5) 0.0156(17) Uani d . . . 1 . .
C C2 0.1270(8) 0.5042(5) 0.9048(6) 0.0164(18) Uani d . . . 1 . .
H H2 0.175554 0.551009 0.882905 0.02 Uiso calc U . R 1 . .
C C3 -0.0105(8) 0.4980(5) 0.8890(6) 0.0205(19) Uani d . . . 1 . .
H H3 -0.056145 0.540181 0.854382 0.025 Uiso calc U . R 1 . .
C C4 -0.0817(9) 0.4303(5) 0.9237(6) 0.0234(19) Uani d . . . 1 . .
H H4 -0.17577 0.426242 0.913516 0.028 Uiso calc U . R 1 . .
C C5 -0.0125(8) 0.3682(5) 0.9738(6) 0.0206(19) Uani d . . . 1 . .
H H5 -0.061079 0.322356 0.99815 0.025 Uiso calc U . R 1 . .
C C6 0.1244(8) 0.3722(5) 0.9885(6) 0.0181(18) Uani d . . . 1 . .
C C7 0.2068(8) 0.3068(5) 1.0435(6) 0.0189(18) Uani d . . . 1 . .
C C8 0.1659(9) 0.2192(5) 1.0074(7) 0.022(2) Uani d . . . 1 . .
C C9 0.1757(9) 0.3151(5) 1.1528(7) 0.025(2) Uani d . . . 1 . .
C C10 0.7343(8) 0.4858(6) 0.6419(6) 0.034(2) Uani d . . . 1 . .
H H10A 0.809465 0.496726 0.685811 0.05 Uiso calc U . R 1 . .
H H10B 0.758119 0.503753 0.576829 0.05 Uiso calc U . R 1 . .
H H10C 0.714588 0.426575 0.641466 0.05 Uiso calc U . R 1 . .
C C11 0.6112(9) 0.5331(5) 0.6756(6) 0.026(2) Uani d . . . 1 . .
H H11A 0.532074 0.514045 0.638534 0.032 Uiso calc U . R 1 . .
H H11B 0.624028 0.592508 0.661729 0.032 Uiso calc U . R 1 . .
C C12 0.5832(8) 0.5225(5) 0.7827(6) 0.0218(19) Uani d . . . 1 . .
H H12A 0.658082 0.546314 0.820594 0.026 Uiso calc U . R 1 . .
H H12B 0.577111 0.462991 0.798254 0.026 Uiso calc U . R 1 . .
C C13 0.4523(8) 0.5652(4) 0.8103(6) 0.0178(18) Uani d . . . 1 . .
H H13A 0.453907 0.622123 0.784545 0.021 Uiso calc U . R 1 . .
H H13B 0.377132 0.535776 0.778607 0.021 Uiso calc U . R 1 . .
C C14 0.4242(8) 0.5694(4) 0.9179(6) 0.0135(17) Uani d . . . 1 . .
C C15 0.4197(8) 0.6386(4) 0.9706(6) 0.0144(17) Uani d . . . 1 . .
C C16 0.3893(9) 0.6501(5) 1.0797(6) 0.0179(18) Uani d . . . 1 . .
C C17 0.2516(8) 0.6159(5) 1.1041(6) 0.024(2) Uani d . . . 1 . .
H H17A 0.252684 0.555636 1.097644 0.036 Uiso calc U . R 1 . .
H H17B 0.184615 0.639151 1.060058 0.036 Uiso calc U . R 1 . .
H H17C 0.228856 0.6307 1.170479 0.036 Uiso calc U . R 1 . .
C C18 0.4993(9) 0.6096(6) 1.1417(7) 0.030(2) Uani d . . . 1 . .
H H18A 0.478273 0.617239 1.209988 0.046 Uiso calc U . R 1 . .
H H18B 0.586062 0.635313 1.127542 0.046 Uiso calc U . R 1 . .
H H18C 0.503752 0.550504 1.127118 0.046 Uiso calc U . R 1 . .
C C19 0.3906(9) 0.7425(5) 1.1057(6) 0.025(2) Uani d . . . 1 . .
H H19A 0.319427 0.771044 1.069995 0.037 Uiso calc U . R 1 . .
H H19B 0.477762 0.766381 1.088769 0.037 Uiso calc U . R 1 . .
H H19C 0.375533 0.749005 1.174981 0.037 Uiso calc U . R 1 . .
C C20 0.3442(9) 0.7483(5) 0.8638(6) 0.0206(19) Uani d . . . 1 . .
C C21 0.3819(10) 0.8305(5) 0.8197(7) 0.034(2) Uani d . . . 1 . .
H H21A 0.36728 0.828406 0.749912 0.052 Uiso calc U . R 1 . .
H H21B 0.476691 0.842153 0.832987 0.052 Uiso calc U . R 1 . .
H H21C 0.326243 0.874184 0.847542 0.052 Uiso calc U . R 1 . .
C C22 0.3006(7) 0.4507(5) 0.4748(5) 0.0161(15) Uani d . . . 1 . .
C C23 0.3587(8) 0.5121(5) 0.4214(6) 0.0166(18) Uani d . . . 1 . .
H H23 0.30867 0.559171 0.402101 0.02 Uiso calc U . R 1 . .
C C24 0.4931(8) 0.5035(5) 0.3963(6) 0.022(2) Uani d . . . 1 . .
H H24 0.536364 0.545287 0.359835 0.026 Uiso calc U . R 1 . .
C C25 0.5625(8) 0.4349(5) 0.4244(6) 0.0188(18) Uani d . . . 1 . .
H H25 0.653644 0.428887 0.405886 0.023 Uiso calc U . R 1 . .
C C26 0.5027(8) 0.3739(5) 0.4792(6) 0.0194(18) Uani d . . . 1 . .
H H26 0.553641 0.327252 0.498857 0.023 Uiso calc U . R 1 . .
C C27 0.3683(7) 0.3802(4) 0.5060(6) 0.0150(18) Uani d . . . 1 . .
C C28 0.2945(8) 0.3156(5) 0.5672(6) 0.0184(18) Uani d . . . 1 . .
C C29 0.3493(9) 0.3186(6) 0.6705(7) 0.028(2) Uani d . . . 1 . .
C C30 0.3195(10) 0.2289(5) 0.5236(8) 0.032(2) Uani d . . . 1 . .
C C31 -0.1197(9) 0.5118(5) 0.1525(6) 0.030(2) Uani d . . . 1 . .
H H31A -0.037269 0.544351 0.147099 0.044 Uiso calc U . R 1 . .
H H31B -0.17864 0.523858 0.097602 0.044 Uiso calc U . R 1 . .
H H31C -0.097322 0.452879 0.152727 0.044 Uiso calc U . R 1 . .
C C32 -0.1906(8) 0.5337(5) 0.2448(6) 0.0201(18) Uani d . . . 1 . .
H H32A -0.27806 0.504749 0.246447 0.024 Uiso calc U . R 1 . .
H H32B -0.208862 0.593754 0.245242 0.024 Uiso calc U . R 1 . .
C C33 -0.1114(8) 0.5114(5) 0.3354(6) 0.0196(18) Uani d . . . 1 . .
H H33A -0.092174 0.451473 0.335307 0.024 Uiso calc U . R 1 . .
H H33B -0.166172 0.523928 0.392834 0.024 Uiso calc U . R 1 . .
C C34 0.0232(8) 0.5602(5) 0.3412(6) 0.0184(18) Uani d . . . 1 . .
H H34A 0.094279 0.52809 0.308628 0.022 Uiso calc U . R 1 . .
H H34B 0.012902 0.613192 0.306418 0.022 Uiso calc U . R 1 . .
C C35 0.0668(7) 0.5778(4) 0.4442(6) 0.0132(17) Uani d . . . 1 . .
C C36 0.0772(7) 0.6524(4) 0.4836(6) 0.0137(16) Uani d . . . 1 . .
C C37 0.1174(9) 0.6767(5) 0.5873(6) 0.0179(18) Uani d . . . 1 . .
C C38 0.1039(9) 0.7715(5) 0.6022(6) 0.024(2) Uani d . . . 1 . .
H H38A 0.011 0.788334 0.589751 0.037 Uiso calc U . R 1 . .
H H38B 0.163791 0.800324 0.557637 0.037 Uiso calc U . R 1 . .
H H38C 0.12841 0.785591 0.668586 0.037 Uiso calc U . R 1 . .
C C39 0.2631(8) 0.6546(5) 0.6046(7) 0.025(2) Uani d . . . 1 . .
H H39A 0.292416 0.677354 0.66657 0.038 Uiso calc U . R 1 . .
H H39B 0.318149 0.67778 0.552932 0.038 Uiso calc U . R 1 . .
H H39C 0.27293 0.594451 0.60547 0.038 Uiso calc U . R 1 . .
C C40 0.0277(9) 0.6374(5) 0.6637(6) 0.026(2) Uani d . . . 1 . .
H H40A 0.043382 0.577671 0.665226 0.039 Uiso calc U . R 1 . .
H H40B -0.066588 0.64814 0.647864 0.039 Uiso calc U . R 1 . .
H H40C 0.048836 0.66108 0.726825 0.039 Uiso calc U . R 1 . .
C C41 0.1452(8) 0.7348(5) 0.3457(6) 0.0179(18) Uani d . . . 1 . .
C C42 0.0963(9) 0.7982(5) 0.2734(6) 0.025(2) Uani d . . . 1 . .
H H42A 0.172858 0.829737 0.248984 0.037 Uiso calc U . R 1 . .
H H42B 0.033013 0.835824 0.304759 0.037 Uiso calc U . R 1 . .
H H42C 0.051311 0.770128 0.219792 0.037 Uiso calc U . R 1 . .
F F1 0.1712(5) 0.2155(3) 0.9110(4) 0.0308(13) Uani d . . . 1 . .
F F2 0.2506(5) 0.1614(3) 1.0418(4) 0.0288(13) Uani d . . . 1 . .
F F3 0.0433(5) 0.1951(3) 1.0347(4) 0.0326(14) Uani d . . . 1 . .
F F4 0.0462(5) 0.3088(3) 1.1751(4) 0.0358(14) Uani d . . . 1 . .
F F5 0.2410(5) 0.2573(3) 1.2049(4) 0.0349(14) Uani d . . . 1 . .
F F6 0.2189(5) 0.3887(3) 1.1841(4) 0.0347(14) Uani d . . . 1 . .
F F7 0.3169(6) 0.3929(3) 0.7094(4) 0.0390(14) Uani d . . . 1 . .
F F8 0.2942(6) 0.2616(3) 0.7269(4) 0.0393(15) Uani d . . . 1 . .
F F9 0.4822(5) 0.3119(4) 0.6787(4) 0.0422(15) Uani d . . . 1 . .
F F10 0.4449(5) 0.2005(3) 0.5344(5) 0.0368(15) Uani d . . . 1 . .
F F11 0.2391(5) 0.1719(3) 0.5640(4) 0.0309(13) Uani d . . . 1 . .
F F12 0.2910(6) 0.2299(3) 0.4290(4) 0.0396(15) Uani d . . . 1 . .
I I1 0.40086(6) 0.44859(2) 0.97835(4) 0.01656(17) Uani d . . . 1 . .
I I2 0.09720(6) 0.46309(2) 0.51904(4) 0.01526(16) Uani d . . . 1 . .
N N1 0.4424(6) 0.7137(4) 0.9186(5) 0.0154(15) Uani d . . . 1 . .
H H1 0.521437 0.737741 0.922179 0.018 Uiso calc U . R 1 . .
N N2 0.0585(7) 0.7196(4) 0.4184(5) 0.0150(15) Uani d . . . 1 . .
H H2A -0.011346 0.752193 0.425755 0.018 Uiso calc U . R 1 . .
O O1 0.3401(5) 0.3159(3) 1.0304(4) 0.0180(12) Uani d . . . 1 . .
O O2 0.2342(6) 0.7161(4) 0.8518(5) 0.0267(15) Uani d . . . 1 . .
O O3 0.1601(5) 0.3292(3) 0.5683(4) 0.0165(12) Uani d . . . 1 . .
O O4 0.2515(6) 0.6985(4) 0.3362(4) 0.0231(14) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.371(10) ?
C1 C6 . 1.398(10) ?
C1 I1 . 2.121(7) ?
C2 C3 . 1.391(11) ?
C3 C4 . 1.393(11) ?
C4 C5 . 1.403(11) ?
C5 C6 . 1.381(11) ?
C6 C7 . 1.542(11) ?
C7 O1 . 1.350(9) ?
C7 C9 . 1.556(12) ?
C7 C8 . 1.559(11) ?
C8 F3 . 1.339(9) ?
C8 F1 . 1.342(10) ?
C8 F2 . 1.347(10) ?
C9 F4 . 1.333(9) ?
C9 F6 . 1.339(9) ?
C9 F5 . 1.350(10) ?
C10 C11 . 1.522(11) ?
C11 C12 . 1.524(11) ?
C12 C13 . 1.526(11) ?
C13 C14 . 1.524(11) ?
C14 C15 . 1.340(10) ?
C14 I1 . 2.143(7) ?
C15 N1 . 1.433(9) ?
C15 C16 . 1.557(11) ?
C16 C17 . 1.520(11) ?
C16 C18 . 1.540(11) ?
C16 C19 . 1.540(11) ?
C20 O2 . 1.226(10) ?
C20 N1 . 1.359(10) ?
C20 C21 . 1.514(11) ?
C22 C23 . 1.370(10) ?
C22 C27 . 1.394(11) ?
C22 I2 . 2.130(7) ?
C23 C24 . 1.392(10) ?
C24 C25 . 1.365(10) ?
C25 C26 . 1.384(11) ?
C26 C27 . 1.395(11) ?
C27 C28 . 1.538(11) ?
C28 O3 . 1.357(9) ?
C28 C29 . 1.534(12) ?
C28 C30 . 1.550(12) ?
C29 F8 . 1.331(10) ?
C29 F9 . 1.333(10) ?
C29 F7 . 1.358(10) ?
C30 F10 . 1.341(10) ?
C30 F12 . 1.343(12) ?
C30 F11 . 1.346(10) ?
C31 C32 . 1.510(11) ?
C32 C33 . 1.525(10) ?
C33 C34 . 1.559(10) ?
C34 C35 . 1.521(11) ?
C35 C36 . 1.331(10) ?
C35 I2 . 2.150(7) ?
C36 N2 . 1.427(9) ?
C36 C37 . 1.546(11) ?
C37 C39 . 1.513(11) ?
C37 C40 . 1.529(11) ?
C37 C38 . 1.556(10) ?
C41 O4 . 1.218(9) ?
C41 N2 . 1.355(10) ?
C41 C42 . 1.516(11) ?
I1 O1 . 2.347(5) ?
I2 O3 . 2.359(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 123.0(7) ?
C2 C1 I1 . . 120.0(6) ?
C6 C1 I1 . . 117.0(6) ?
C1 C2 C3 . . 118.8(7) ?
C2 C3 C4 . . 120.3(8) ?
C3 C4 C5 . . 119.1(8) ?
C6 C5 C4 . . 121.6(8) ?
C5 C6 C1 . . 117.2(7) ?
C5 C6 C7 . . 124.4(7) ?
C1 C6 C7 . . 118.4(7) ?
O1 C7 C6 . . 112.3(7) ?
O1 C7 C9 . . 108.8(7) ?
C6 C7 C9 . . 108.5(7) ?
O1 C7 C8 . . 108.2(6) ?
C6 C7 C8 . . 109.2(7) ?
C9 C7 C8 . . 109.9(7) ?
F3 C8 F1 . . 108.0(7) ?
F3 C8 F2 . . 105.6(7) ?
F1 C8 F2 . . 107.2(7) ?
F3 C8 C7 . . 114.3(7) ?
F1 C8 C7 . . 110.5(7) ?
F2 C8 C7 . . 110.9(7) ?
F4 C9 F6 . . 107.6(7) ?
F4 C9 F5 . . 106.7(7) ?
F6 C9 F5 . . 106.9(7) ?
F4 C9 C7 . . 114.6(8) ?
F6 C9 C7 . . 109.2(7) ?
F5 C9 C7 . . 111.5(7) ?
C10 C11 C12 . . 113.2(7) ?
C11 C12 C13 . . 110.7(7) ?
C14 C13 C12 . . 115.3(7) ?
C15 C14 C13 . . 125.5(7) ?
C15 C14 I1 . . 123.1(6) ?
C13 C14 I1 . . 111.3(5) ?
C14 C15 N1 . . 115.4(7) ?
C14 C15 C16 . . 129.7(7) ?
N1 C15 C16 . . 114.9(6) ?
C17 C16 C18 . . 111.1(7) ?
C17 C16 C19 . . 108.0(7) ?
C18 C16 C19 . . 106.1(7) ?
C17 C16 C15 . . 110.7(7) ?
C18 C16 C15 . . 110.6(7) ?
C19 C16 C15 . . 110.1(6) ?
O2 C20 N1 . . 122.8(8) ?
O2 C20 C21 . . 122.9(8) ?
N1 C20 C21 . . 114.3(8) ?
C23 C22 C27 . . 123.9(7) ?
C23 C22 I2 . . 119.5(6) ?
C27 C22 I2 . . 116.6(5) ?
C22 C23 C24 . . 118.2(7) ?
C25 C24 C23 . . 119.7(8) ?
C24 C25 C26 . . 121.3(8) ?
C25 C26 C27 . . 120.7(8) ?
C22 C27 C26 . . 116.2(7) ?
C22 C27 C28 . . 119.8(7) ?
C26 C27 C28 . . 124.0(7) ?
O3 C28 C29 . . 109.5(7) ?
O3 C28 C27 . . 111.7(7) ?
C29 C28 C27 . . 109.0(7) ?
O3 C28 C30 . . 108.1(7) ?
C29 C28 C30 . . 109.7(7) ?
C27 C28 C30 . . 108.8(7) ?
F8 C29 F9 . . 107.8(8) ?
F8 C29 F7 . . 106.4(8) ?
F9 C29 F7 . . 106.0(7) ?
F8 C29 C28 . . 112.4(7) ?
F9 C29 C28 . . 115.3(8) ?
F7 C29 C28 . . 108.4(7) ?
F10 C30 F12 . . 107.9(8) ?
F10 C30 F11 . . 105.9(7) ?
F12 C30 F11 . . 107.0(8) ?
F10 C30 C28 . . 114.7(8) ?
F12 C30 C28 . . 109.7(7) ?
F11 C30 C28 . . 111.2(8) ?
C31 C32 C33 . . 113.7(7) ?
C32 C33 C34 . . 111.5(7) ?
C35 C34 C33 . . 112.8(7) ?
C36 C35 C34 . . 125.3(7) ?
C36 C35 I2 . . 125.2(6) ?
C34 C35 I2 . . 109.4(5) ?
C35 C36 N2 . . 115.0(7) ?
C35 C36 C37 . . 129.3(7) ?
N2 C36 C37 . . 115.5(6) ?
C39 C37 C40 . . 110.8(7) ?
C39 C37 C36 . . 109.4(7) ?
C40 C37 C36 . . 113.0(7) ?
C39 C37 C38 . . 107.2(7) ?
C40 C37 C38 . . 105.6(7) ?
C36 C37 C38 . . 110.7(7) ?
O4 C41 N2 . . 123.4(8) ?
O4 C41 C42 . . 122.2(8) ?
N2 C41 C42 . . 114.3(7) ?
C1 I1 C14 . . 95.3(3) ?
C1 I1 O1 . . 75.4(2) ?
C14 I1 O1 . . 170.2(3) ?
C22 I2 C35 . . 94.3(3) ?
C22 I2 O3 . . 75.2(3) ?
C35 I2 O3 . . 166.4(2) ?
C20 N1 C15 . . 121.2(7) ?
C41 N2 C36 . . 121.9(6) ?
C7 O1 I1 . . 113.5(5) ?
C28 O3 I2 . . 114.1(4) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_ito117m
_database_code_depnum_ccdc_archive 'CCDC 2093231'
loop_
_audit_author_name
_audit_author_address
'Jinkui Chai'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 F6 I N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         537.27

_chemical_melting_point          ?

_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                   10.9318(5)
_cell_length_b                   28.7192(12)
_cell_length_c                   13.4936(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.8262(19)
_cell_angle_gamma                90
_cell_volume                     4231.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      2.3433
_cell_measurement_theta_max      28.5182
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2128

_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            40809
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_unetI/netI     0.1069
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             10915
_reflns_number_gt                7437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1466
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.015
_refine_ls_number_reflns         10915
_refine_ls_number_parameters     881
_refine_ls_number_restraints     2145
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+15.6109P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.814
_refine_diff_density_min         -1.904
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 (Ver 2019.11, Bruker AXS Inc., 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Ver 2019.11, Bruker AXS Inc., 2020)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9261(7) -0.3674(3) 0.2211(5) 0.0326(15) Uani d U P D 0.902(2) A 1
C C2 0.8069(8) -0.4184(3) 0.0993(6) 0.0386(16) Uani d U P D 0.902(2) A 1
C C3 0.8104(6) -0.3707(2) 0.1515(5) 0.0233(12) Uani d U P D 0.902(2) A 1
C C4 0.8122(4) -0.33179(14) 0.0705(3) 0.0185(12) Uani d U P DG 0.902(2) A 1
C C5 0.9085(3) -0.32769(18) 0.0075(4) 0.0203(12) Uani d U P DG 0.902(2) A 1
H H5 0.977614 -0.347628 0.015711 0.024 Uiso calc U P R 0.902(2) A 1
C C6 0.9037(4) -0.2944(2) -0.0673(4) 0.0213(14) Uani d U P DG 0.902(2) A 1
H H6 0.969535 -0.291612 -0.110372 0.026 Uiso calc U P R 0.902(2) A 1
C C7 0.8026(4) -0.2652(2) -0.0793(4) 0.0229(14) Uani d U P DG 0.902(2) A 1
H H7 0.799321 -0.2425 -0.130482 0.027 Uiso calc U P R 0.902(2) A 1
C C8 0.7063(4) -0.26934(17) -0.0163(4) 0.0263(13) Uani d U P DG 0.902(2) A 1
H H8 0.637185 -0.249405 -0.02451 0.032 Uiso calc U P R 0.902(2) A 1
C C9 0.7111(3) -0.30262(15) 0.0586(3) 0.0226(13) Uani d U P DG 0.902(2) A 1
C C10 0.2632(9) -0.3778(3) -0.0521(7) 0.046(2) Uani d U P D 0.902(2) A 1
H H10A 0.261759 -0.373165 -0.124132 0.069 Uiso calc U P R 0.902(2) A 1
H H10B 0.185988 -0.392056 -0.033937 0.069 Uiso calc U P R 0.902(2) A 1
H H10C 0.331577 -0.398262 -0.031783 0.069 Uiso calc U P R 0.902(2) A 1
C C11 0.2788(7) -0.3313(3) -0.0005(6) 0.0352(16) Uani d U P D 0.902(2) A 1
H H11A 0.290365 -0.33642 0.071925 0.042 Uiso calc U P R 0.902(2) A 1
H H11B 0.203547 -0.312562 -0.012571 0.042 Uiso calc U P R 0.902(2) A 1
C C12 0.3886(7) -0.3043(2) -0.0370(5) 0.0266(14) Uani d U P D 0.902(2) A 1
H H12A 0.377205 -0.299322 -0.109519 0.032 Uiso calc U P R 0.902(2) A 1
H H12B 0.463861 -0.32297 -0.024682 0.032 Uiso calc U P R 0.902(2) A 1
C C13 0.4048(6) -0.2567(2) 0.0150(5) 0.0219(12) Uani d U P D 0.902(2) A 1
C C14 0.4694(6) -0.2477(2) 0.0943(5) 0.0228(12) Uani d U P D 0.902(2) A 1
C C15 0.4779(6) -0.2031(2) 0.1499(5) 0.0213(13) Uani d U P D 0.902(2) A 1
H H15A 0.413818 -0.203238 0.199251 0.026 Uiso calc U P R 0.902(2) A 1
H H15B 0.457737 -0.177523 0.102592 0.026 Uiso calc U P R 0.902(2) A 1
C C16 0.5999(7) -0.1912(3) 0.2045(7) 0.0388(17) Uani d U P D 0.902(2) A 1
H H16A 0.614356 -0.213085 0.260504 0.047 Uiso calc U P R 0.902(2) A 1
H H16B 0.667052 -0.19526 0.158626 0.047 Uiso calc U P R 0.902(2) A 1
C C17 0.6026(8) -0.1417(3) 0.2439(7) 0.042(2) Uani d U P D 0.902(2) A 1
H H17A 0.598085 -0.119767 0.188195 0.063 Uiso calc U P R 0.902(2) A 1
H H17B 0.678844 -0.136578 0.283701 0.063 Uiso calc U P R 0.902(2) A 1
H H17C 0.532564 -0.136749 0.285321 0.063 Uiso calc U P R 0.902(2) A 1
C C18 0.3402(6) -0.2072(3) -0.1251(5) 0.0247(14) Uani d U P D 0.902(2) A 1
C C19 0.2571(8) -0.1687(3) -0.1598(5) 0.032(2) Uani d U P D 0.902(2) A 1
H H19A 0.301176 -0.147616 -0.20259 0.048 Uiso calc U P R 0.902(2) A 1
H H19B 0.229368 -0.151493 -0.102397 0.048 Uiso calc U P R 0.902(2) A 1
H H19C 0.186069 -0.181798 -0.197283 0.048 Uiso calc U P R 0.902(2) A 1
F F1 0.9292(6) -0.32610(19) 0.2659(4) 0.0597(16) Uani d U P D 0.902(2) A 1
F F2 0.9284(6) -0.3998(2) 0.2918(4) 0.0473(16) Uani d U P D 0.902(2) A 1
F F3 1.0333(4) -0.3715(2) 0.1770(4) 0.0563(15) Uani d U P D 0.902(2) A 1
F F4 0.7898(6) -0.45294(15) 0.1635(4) 0.0501(15) Uani d U P D 0.902(2) A 1
F F5 0.9080(8) -0.4291(2) 0.0520(5) 0.0670(18) Uani d U P D 0.902(2) A 1
F F6 0.7138(8) -0.4195(2) 0.0332(5) 0.077(2) Uani d U P D 0.902(2) A 1
I I1 0.57230(4) -0.30593(3) 0.16197(3) 0.02294(18) Uani d U P D 0.902(2) A 1
N N1 0.3313(5) -0.21985(18) -0.0284(4) 0.0202(12) Uani d U P D 0.902(2) A 1
H H1 0.27937 -0.205114 0.008326 0.024 Uiso calc U P R 0.902(2) A 1
O O1 0.7120(5) -0.36751(17) 0.2082(4) 0.0316(12) Uani d U P D 0.902(2) A 1
O O2 0.4149(5) -0.2254(2) -0.1797(4) 0.0293(14) Uani d U P D 0.902(2) A 1
C C1A 0.936(2) -0.3845(11) 0.208(2) 0.035(3) Uani d U P D 0.098(2) A 2
C C2A 0.817(3) -0.4284(10) 0.075(2) 0.039(3) Uani d U P D 0.098(2) A 2
C C3A 0.8209(16) -0.3834(9) 0.1391(19) 0.029(2) Uani d U P D 0.098(2) A 2
C C4A 0.8231(14) -0.3413(10) 0.066(2) 0.022(2) Uani d U P DG 0.098(2) A 2
C C5A 0.924(2) -0.3309(15) 0.012(3) 0.021(3) Uani d U P DG 0.098(2) A 2
H H5A 0.995964 -0.349477 0.018964 0.025 Uiso calc U P R 0.098(2) A 2
C C6A 0.920(3) -0.2931(18) -0.053(4) 0.021(3) Uani d U P DG 0.098(2) A 2
H H6A 0.9896 -0.285992 -0.089868 0.026 Uiso calc U P R 0.098(2) A 2
C C7A 0.815(3) -0.2659(17) -0.063(4) 0.024(3) Uani d U P DG 0.098(2) A 2
H H7A 0.812907 -0.240133 -0.107168 0.028 Uiso calc U P R 0.098(2) A 2
C C8A 0.714(2) -0.2764(13) -0.009(3) 0.024(3) Uani d U P DG 0.098(2) A 2
H H8A 0.642577 -0.257759 -0.015637 0.029 Uiso calc U P R 0.098(2) A 2
C C9A 0.7181(14) -0.3141(9) 0.0560(19) 0.022(3) Uani d U P DG 0.098(2) A 2
C C10A 0.226(7) -0.392(2) -0.038(6) 0.040(6) Uani d U P D 0.098(2) A 2
H H10D 0.172594 -0.376414 -0.088532 0.059 Uiso calc U P R 0.098(2) A 2
H H10E 0.175542 -0.410192 0.005881 0.059 Uiso calc U P R 0.098(2) A 2
H H10F 0.281977 -0.413001 -0.071187 0.059 Uiso calc U P R 0.098(2) A 2
C C11A 0.299(6) -0.3561(16) 0.021(4) 0.033(3) Uani d U P D 0.098(2) A 2
H H11C 0.365379 -0.371762 0.061024 0.04 Uiso calc U P R 0.098(2) A 2
H H11D 0.244732 -0.340467 0.067846 0.04 Uiso calc U P R 0.098(2) A 2
C C12A 0.354(5) -0.3198(12) -0.047(3) 0.031(3) Uani d U P D 0.098(2) A 2
H H12C 0.292919 -0.312546 -0.101561 0.038 Uiso calc U P R 0.098(2) A 2
H H12D 0.426677 -0.33326 -0.076435 0.038 Uiso calc U P R 0.098(2) A 2
C C13A 0.390(4) -0.2745(9) 0.007(3) 0.025(2) Uani d U P D 0.098(2) A 2
C C14A 0.462(2) -0.2699(7) 0.085(2) 0.025(3) Uani d U P D 0.098(2) A 2
C C15A 0.462(3) -0.2271(7) 0.148(3) 0.029(3) Uani d U P D 0.098(2) A 2
H H15C 0.474826 -0.236987 0.217749 0.034 Uiso calc U P R 0.098(2) A 2
H H15D 0.37942 -0.213101 0.140557 0.034 Uiso calc U P R 0.098(2) A 2
C C16A 0.555(6) -0.1888(14) 0.128(4) 0.029(3) Uani d U P D 0.098(2) A 2
H H16C 0.63342 -0.203383 0.110711 0.035 Uiso calc U P R 0.098(2) A 2
H H16D 0.524825 -0.169785 0.071338 0.035 Uiso calc U P R 0.098(2) A 2
C C17A 0.579(7) -0.157(2) 0.218(5) 0.034(6) Uani d U P D 0.098(2) A 2
H H17D 0.501108 -0.146576 0.241889 0.051 Uiso calc U P R 0.098(2) A 2
H H17E 0.627937 -0.130458 0.198406 0.051 Uiso calc U P R 0.098(2) A 2
H H17F 0.624282 -0.174676 0.270372 0.051 Uiso calc U P R 0.098(2) A 2
C C18A 0.364(5) -0.2130(18) -0.113(3) 0.024(3) Uani d U P D 0.098(2) A 2
C C19A 0.269(6) -0.185(3) -0.168(4) 0.026(5) Uani d U P D 0.098(2) A 2
H H19D 0.206486 -0.175161 -0.122616 0.04 Uiso calc U P R 0.098(2) A 2
H H19E 0.306324 -0.1576 -0.197003 0.04 Uiso calc U P R 0.098(2) A 2
H H19F 0.229992 -0.204121 -0.2212 0.04 Uiso calc U P R 0.098(2) A 2
F F1A 0.967(3) -0.3420(12) 0.239(3) 0.046(5) Uani d U P D 0.098(2) A 2
F F2A 0.925(4) -0.4118(17) 0.287(3) 0.038(5) Uani d U P D 0.098(2) A 2
F F3A 1.034(2) -0.4006(15) 0.161(3) 0.043(5) Uani d U P D 0.098(2) A 2
F F4A 0.799(6) -0.4649(10) 0.134(3) 0.051(5) Uani d U P D 0.098(2) A 2
F F5A 0.725(5) -0.4283(17) 0.007(3) 0.046(6) Uani d U P D 0.098(2) A 2
F F6A 0.921(4) -0.4344(18) 0.033(4) 0.051(5) Uani d U P D 0.098(2) A 2
I I1A 0.5609(5) -0.3338(3) 0.1305(6) 0.049(2) Uani d U P D 0.098(2) A 2
N N1A 0.326(4) -0.2332(13) -0.027(3) 0.023(3) Uani d U P D 0.098(2) A 2
H H1A 0.26562 -0.221462 0.004901 0.028 Uiso calc U P R 0.098(2) A 2
O O1A 0.7200(17) -0.3860(8) 0.1925(19) 0.031(3) Uani d U P D 0.098(2) A 2
O O2A 0.454(4) -0.230(2) -0.153(3) 0.023(6) Uani d U P D 0.098(2) A 2
C C20 0.0842(6) -0.2114(2) 0.1790(4) 0.0241(13) Uani d U . . 1.0 . .
C C21 0.0016(6) -0.1639(2) 0.0322(5) 0.0253(13) Uani d U . . 1.0 . .
C C22 0.0916(5) -0.16447(19) 0.1231(4) 0.0180(10) Uani d U . . 1.0 . .
C C23 0.0586(5) -0.12368(19) 0.1903(4) 0.0177(11) Uani d U . . 1.0 . .
C C24 -0.0431(5) -0.1234(2) 0.2490(4) 0.0206(12) Uani d U . . 1.0 . .
H H24 -0.09682 -0.149385 0.247367 0.025 Uiso calc U . R 1.0 . .
C C25 -0.0674(6) -0.0858(2) 0.3096(4) 0.0250(13) Uani d U . . 1.0 . .
H H25 -0.135506 -0.086749 0.350672 0.03 Uiso calc U . R 1.0 . .
C C26 0.0069(6) -0.0474(2) 0.3104(4) 0.0263(13) Uani d U . . 1.0 . .
H H26 -0.009938 -0.021463 0.351265 0.032 Uiso calc U . R 1.0 . .
C C27 0.1070(6) -0.0466(2) 0.2508(4) 0.0250(13) Uani d U . . 1.0 . .
H H27 0.159148 -0.02013 0.251126 0.03 Uiso calc U . R 1.0 . .
C C28 0.1303(5) -0.08410(19) 0.1916(4) 0.0191(11) Uani d U . . 1.0 . .
C C29 0.6032(15) -0.0051(6) 0.3646(12) 0.051(4) Uani d U P D 0.660(7) B 1
H H29A 0.618672 -0.03793 0.350374 0.076 Uiso calc U P R 0.660(7) B 1
H H29B 0.595392 -0.000932 0.436105 0.076 Uiso calc U P R 0.660(7) B 1
H H29C 0.671441 0.013856 0.342766 0.076 Uiso calc U P R 0.660(7) B 1
C C30 0.4876(12) 0.0099(5) 0.3107(9) 0.053(2) Uani d U P D 0.660(7) B 1
H H30A 0.417232 -0.003915 0.343538 0.064 Uiso calc U P R 0.660(7) B 1
H H30B 0.480405 0.044209 0.315339 0.064 Uiso calc U P R 0.660(7) B 1
C C31 0.4811(15) -0.0038(7) 0.2044(14) 0.034(2) Uani d U P D 0.660(7) B 1
H H31A 0.476867 -0.038145 0.19971 0.041 Uiso calc U P R 0.660(7) B 1
H H31B 0.556912 0.006436 0.173581 0.041 Uiso calc U P R 0.660(7) B 1
C C32 0.3701(8) 0.0173(3) 0.1464(6) 0.0205(15) Uani d U P D 0.660(7) B 1
C C33 0.2806(8) -0.0064(3) 0.1003(6) 0.0203(16) Uani d U P D 0.660(7) B 1
C C34 0.1715(14) 0.0160(7) 0.0444(13) 0.0235(18) Uani d U P D 0.660(7) B 1
H H34A 0.155014 0.046514 0.075058 0.028 Uiso calc U P R 0.660(7) B 1
H H34B 0.098576 -0.003901 0.052045 0.028 Uiso calc U P R 0.660(7) B 1
C C35 0.1895(15) 0.0233(5) -0.0671(10) 0.027(2) Uani d U P D 0.660(7) B 1
H H35A 0.122525 0.043424 -0.094489 0.032 Uiso calc U P R 0.660(7) B 1
H H35B 0.267436 0.040165 -0.074495 0.032 Uiso calc U P R 0.660(7) B 1
C C36 0.1919(12) -0.0213(5) -0.1294(11) 0.029(3) Uani d U P D 0.660(7) B 1
H H36A 0.263798 -0.039885 -0.108598 0.043 Uiso calc U P R 0.660(7) B 1
H H36B 0.195971 -0.013116 -0.199669 0.043 Uiso calc U P R 0.660(7) B 1
H H36C 0.117381 -0.039384 -0.119764 0.043 Uiso calc U P R 0.660(7) B 1
C C37 0.4176(16) 0.0920(3) 0.0681(14) 0.024(2) Uani d U P D 0.660(7) B 1
C C38 0.3863(10) 0.1427(3) 0.0668(7) 0.024(2) Uani d U P D 0.660(7) B 1
H H38A 0.461296 0.161064 0.077878 0.036 Uiso calc U P R 0.660(7) B 1
H H38B 0.330111 0.149392 0.119338 0.036 Uiso calc U P R 0.660(7) B 1
H H38C 0.34706 0.15086 0.002252 0.036 Uiso calc U P R 0.660(7) B 1
N N2 0.3666(8) 0.0672(2) 0.1426(6) 0.0208(17) Uani d U P D 0.660(7) B 1
H H2 0.33045 0.08249 0.189573 0.025 Uiso calc U P R 0.660(7) B 1
O O4 0.4864(15) 0.0738(4) 0.0107(13) 0.029(2) Uani d U P D 0.660(7) B 1
C C29A 0.218(3) -0.0065(8) -0.126(2) 0.029(5) Uani d U P D 0.340(7) B 2
H H29D 0.293694 -0.018643 -0.09355 0.044 Uiso calc U P R 0.340(7) B 2
H H29E 0.236045 0.005901 -0.191565 0.044 Uiso calc U P R 0.340(7) B 2
H H29F 0.158007 -0.031723 -0.134134 0.044 Uiso calc U P R 0.340(7) B 2
C C30A 0.168(3) 0.0312(10) -0.0645(17) 0.025(3) Uani d U P D 0.340(7) B 2
H H30C 0.220529 0.059073 -0.06884 0.03 Uiso calc U P R 0.340(7) B 2
H H30D 0.085123 0.039575 -0.092046 0.03 Uiso calc U P R 0.340(7) B 2
C C31A 0.159(2) 0.0182(13) 0.041(2) 0.024(2) Uani d U P D 0.340(7) B 2
H H31C 0.127898 -0.014058 0.045352 0.028 Uiso calc U P R 0.340(7) B 2
H H31D 0.099992 0.039009 0.072233 0.028 Uiso calc U P R 0.340(7) B 2
C C32A 0.2824(12) 0.0212(5) 0.1005(11) 0.021(2) Uani d U P D 0.340(7) B 2
C C33A 0.3486(13) -0.0132(4) 0.1390(11) 0.025(2) Uani d U P D 0.340(7) B 2
C C34A 0.468(3) -0.0082(14) 0.200(2) 0.034(3) Uani d U P D 0.340(7) B 2
H H34C 0.490392 0.025162 0.205131 0.041 Uiso calc U P R 0.340(7) B 2
H H34D 0.534055 -0.024465 0.166055 0.041 Uiso calc U P R 0.340(7) B 2
C C35A 0.4600(17) -0.0285(9) 0.3057(12) 0.040(3) Uani d U P D 0.340(7) B 2
H H35C 0.391751 -0.012912 0.338105 0.048 Uiso calc U P R 0.340(7) B 2
H H35D 0.439483 -0.061972 0.299892 0.048 Uiso calc U P R 0.340(7) B 2
C C36A 0.576(2) -0.0234(11) 0.373(2) 0.051(5) Uani d U P D 0.340(7) B 2
H H36D 0.641149 -0.042889 0.347205 0.076 Uiso calc U P R 0.340(7) B 2
H H36E 0.559301 -0.033288 0.440175 0.076 Uiso calc U P R 0.340(7) B 2
H H36F 0.602453 0.009225 0.373638 0.076 Uiso calc U P R 0.340(7) B 2
C C37A 0.429(3) 0.0837(6) 0.069(3) 0.025(3) Uani d U P D 0.340(7) B 2
C C38A 0.452(3) 0.1344(6) 0.0866(19) 0.046(5) Uani d U P D 0.340(7) B 2
H H38D 0.513359 0.138204 0.141695 0.069 Uiso calc U P R 0.340(7) B 2
H H38E 0.375921 0.149718 0.103073 0.069 Uiso calc U P R 0.340(7) B 2
H H38F 0.483099 0.148429 0.026501 0.069 Uiso calc U P R 0.340(7) B 2
N N2A 0.3297(14) 0.0675(4) 0.1170(12) 0.023(2) Uani d U P D 0.340(7) B 2
H H2A 0.293975 0.085847 0.158943 0.028 Uiso calc U P R 0.340(7) B 2
O O4A 0.478(3) 0.0607(7) 0.006(2) 0.031(4) Uani d U P D 0.340(7) B 2
F F7 0.1477(4) -0.20944(12) 0.2661(3) 0.0318(9) Uani d U . . 1.0 . .
F F8 0.1327(4) -0.24603(12) 0.1272(3) 0.0356(10) Uani d U . . 1.0 . .
F F9 -0.0309(3) -0.22499(12) 0.1972(3) 0.0346(9) Uani d U . . 1.0 . .
F F10 0.0247(4) -0.19802(13) -0.0324(3) 0.0340(9) Uani d U . . 1.0 . .
F F11 -0.1172(3) -0.16773(15) 0.0533(3) 0.0403(10) Uani d U . . 1.0 . .
F F12 0.0120(4) -0.12362(13) -0.0170(3) 0.0346(9) Uani d U . . 1.0 . .
I I2 0.28345(4) -0.08190(2) 0.10062(3) 0.02190(11) Uani d . . D 1.0 . .
O O3 0.2083(3) -0.16004(13) 0.0919(3) 0.0186(8) Uani d U . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 F2 . 1.330(8) ?
C1 F1 . 1.332(9) ?
C1 F3 . 1.346(8) ?
C1 C3 . 1.540(10) ?
C2 F6 . 1.320(11) ?
C2 F4 . 1.336(8) ?
C2 F5 . 1.339(10) ?
C2 C3 . 1.539(10) ?
C3 O1 . 1.354(7) ?
C3 C4 . 1.564(7) ?
C4 C5 . 1.39 ?
C4 C9 . 1.39 ?
C5 C6 . 1.39 ?
C6 C7 . 1.39 ?
C7 C8 . 1.39 ?
C8 C9 . 1.39 ?
C9 I1 . 2.114(3) ?
C10 C11 . 1.512(10) ?
C11 C12 . 1.531(10) ?
C12 C13 . 1.543(9) ?
C13 C14 . 1.280(9) ?
C13 N1 . 1.435(8) ?
C14 C15 . 1.485(9) ?
C14 I1 . 2.190(7) ?
C15 C16 . 1.530(10) ?
C16 C17 . 1.517(11) ?
C18 O2 . 1.241(8) ?
C18 N1 . 1.363(8) ?
C18 C19 . 1.491(10) ?
I1 O1 . 2.399(5) ?
C1A F2A . 1.326(12) ?
C1A F1A . 1.328(13) ?
C1A F3A . 1.349(13) ?
C1A C3A . 1.534(13) ?
C2A F6A . 1.311(14) ?
C2A F5A . 1.336(14) ?
C2A F4A . 1.336(12) ?
C2A C3A . 1.551(13) ?
C3A O1A . 1.349(11) ?
C3A C4A . 1.559(10) ?
C4A C5A . 1.39 ?
C4A C9A . 1.39 ?
C5A C6A . 1.39 ?
C6A C7A . 1.39 ?
C7A C8A . 1.39 ?
C8A C9A . 1.39 ?
C9A I1A . 2.110(8) ?
C10A C11A . 1.513(14) ?
C11A C12A . 1.533(14) ?
C12A C13A . 1.534(13) ?
C13A C14A . 1.285(13) ?
C13A N1A . 1.442(12) ?
C14A C15A . 1.492(13) ?
C14A I1A . 2.204(11) ?
C15A C16A . 1.531(14) ?
C16A C17A . 1.518(15) ?
C18A O2A . 1.245(12) ?
C18A N1A . 1.372(13) ?
C18A C19A . 1.490(14) ?
I1A O1A . 2.414(10) ?
C20 F7 . 1.336(7) ?
C20 F8 . 1.339(6) ?
C20 F9 . 1.351(7) ?
C20 C22 . 1.549(8) ?
C21 F12 . 1.341(7) ?
C21 F10 . 1.344(7) ?
C21 F11 . 1.348(7) ?
C21 C22 . 1.534(9) ?
C22 O3 . 1.369(6) ?
C22 C23 . 1.535(7) ?
C23 C28 . 1.381(8) ?
C23 C24 . 1.397(7) ?
C24 C25 . 1.387(8) ?
C25 C26 . 1.370(9) ?
C26 C27 . 1.389(8) ?
C27 C28 . 1.373(8) ?
C28 I2 . 2.125(5) ?
C29 C30 . 1.490(18) ?
C30 C31 . 1.49(2) ?
C31 C32 . 1.535(19) ?
C32 C33 . 1.321(10) ?
C32 N2 . 1.437(10) ?
C33 C34 . 1.521(18) ?
C33 I2 . 2.169(8) ?
C34 C35 . 1.542(18) ?
C35 C36 . 1.532(16) ?
C37 O4 . 1.224(9) ?
C37 N2 . 1.372(11) ?
C37 C38 . 1.495(12) ?
C29A C30A . 1.49(2) ?
C30A C31A . 1.49(2) ?
C31A C32A . 1.53(2) ?
C32A C33A . 1.316(12) ?
C32A N2A . 1.439(12) ?
C33A C34A . 1.52(2) ?
C33A I2 . 2.153(11) ?
C34A C35A . 1.54(2) ?
C35A C36A . 1.529(18) ?
C37A O4A . 1.222(11) ?
C37A N2A . 1.372(13) ?
C37A C38A . 1.495(13) ?
I2 O3 . 2.391(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 C1 F1 . . 107.3(6) ?
F2 C1 F3 . . 105.7(6) ?
F1 C1 F3 . . 105.9(7) ?
F2 C1 C3 . . 112.4(6) ?
F1 C1 C3 . . 109.5(6) ?
F3 C1 C3 . . 115.6(6) ?
F6 C2 F4 . . 107.0(7) ?
F6 C2 F5 . . 107.4(7) ?
F4 C2 F5 . . 106.5(6) ?
F6 C2 C3 . . 109.4(7) ?
F4 C2 C3 . . 111.4(6) ?
F5 C2 C3 . . 114.8(7) ?
O1 C3 C2 . . 108.4(6) ?
O1 C3 C1 . . 107.6(5) ?
C2 C3 C1 . . 109.5(6) ?
O1 C3 C4 . . 112.6(5) ?
C2 C3 C4 . . 108.5(5) ?
C1 C3 C4 . . 110.1(5) ?
C5 C4 C9 . . 120.0 ?
C5 C4 C3 . . 121.6(3) ?
C9 C4 C3 . . 118.3(3) ?
C4 C5 C6 . . 120.0 ?
C7 C6 C5 . . 120.0 ?
C6 C7 C8 . . 120.0 ?
C9 C8 C7 . . 120.0 ?
C8 C9 C4 . . 120.0 ?
C8 C9 I1 . . 120.6(2) ?
C4 C9 I1 . . 119.3(2) ?
C10 C11 C12 . . 111.8(6) ?
C11 C12 C13 . . 112.2(5) ?
C14 C13 N1 . . 117.8(6) ?
C14 C13 C12 . . 127.3(6) ?
N1 C13 C12 . . 114.7(6) ?
C13 C14 C15 . . 128.0(6) ?
C13 C14 I1 . . 116.4(5) ?
C15 C14 I1 . . 115.5(5) ?
C14 C15 C16 . . 117.8(6) ?
C17 C16 C15 . . 112.3(6) ?
O2 C18 N1 . . 122.4(6) ?
O2 C18 C19 . . 122.3(6) ?
N1 C18 C19 . . 115.3(6) ?
C9 I1 C14 . . 93.50(19) ?
C9 I1 O1 . . 74.72(14) ?
C14 I1 O1 . . 168.19(19) ?
C18 N1 C13 . . 121.4(5) ?
C3 O1 I1 . . 114.6(4) ?
F2A C1A F1A . . 108.9(16) ?
F2A C1A F3A . . 106.3(15) ?
F1A C1A F3A . . 105.7(16) ?
F2A C1A C3A . . 113.1(15) ?
F1A C1A C3A . . 111.1(15) ?
F3A C1A C3A . . 111.3(14) ?
F6A C2A F5A . . 109.7(16) ?
F6A C2A F4A . . 108.3(17) ?
F5A C2A F4A . . 106.8(16) ?
F6A C2A C3A . . 110.5(15) ?
F5A C2A C3A . . 112.4(15) ?
F4A C2A C3A . . 108.9(14) ?
O1A C3A C1A . . 110.1(13) ?
O1A C3A C2A . . 104.5(12) ?
C1A C3A C2A . . 108.6(12) ?
O1A C3A C4A . . 114.6(10) ?
C1A C3A C4A . . 111.2(11) ?
C2A C3A C4A . . 107.3(11) ?
C5A C4A C9A . . 120.0 ?
C5A C4A C3A . . 122.5(8) ?
C9A C4A C3A . . 117.5(8) ?
C4A C5A C6A . . 120.0 ?
C7A C6A C5A . . 120.0 ?
C6A C7A C8A . . 120.0 ?
C9A C8A C7A . . 120.0 ?
C8A C9A C4A . . 120.0 ?
C8A C9A I1A . . 120.5(6) ?
C4A C9A I1A . . 119.3(6) ?
C10A C11A C12A . . 110.9(17) ?
C11A C12A C13A . . 113.1(16) ?
C14A C13A N1A . . 116.4(15) ?
C14A C13A C12A . . 127.6(15) ?
N1A C13A C12A . . 115.7(15) ?
C13A C14A C15A . . 122.2(13) ?
C13A C14A I1A . . 114.4(12) ?
C15A C14A I1A . . 122.6(10) ?
C14A C15A C16A . . 118.5(17) ?
C17A C16A C15A . . 112.6(17) ?
O2A C18A N1A . . 118.9(18) ?
O2A C18A C19A . . 122.(2) ?
N1A C18A C19A . . 114.5(18) ?
C9A I1A C14A . . 92.5(8) ?
C9A I1A O1A . . 75.0(5) ?
C14A I1A O1A . . 161.7(9) ?
C18A N1A C13A . . 117.3(17) ?
C3A O1A I1A . . 112.1(8) ?
F7 C20 F8 . . 106.8(5) ?
F7 C20 F9 . . 107.5(5) ?
F8 C20 F9 . . 106.1(5) ?
F7 C20 C22 . . 110.7(5) ?
F8 C20 C22 . . 111.1(4) ?
F9 C20 C22 . . 114.3(5) ?
F12 C21 F10 . . 106.5(5) ?
F12 C21 F11 . . 106.3(5) ?
F10 C21 F11 . . 106.9(5) ?
F12 C21 C22 . . 109.8(5) ?
F10 C21 C22 . . 112.2(5) ?
F11 C21 C22 . . 114.6(5) ?
O3 C22 C21 . . 108.9(4) ?
O3 C22 C23 . . 111.1(4) ?
C21 C22 C23 . . 107.7(5) ?
O3 C22 C20 . . 107.6(5) ?
C21 C22 C20 . . 110.6(5) ?
C23 C22 C20 . . 111.0(4) ?
C28 C23 C24 . . 117.0(5) ?
C28 C23 C22 . . 119.1(5) ?
C24 C23 C22 . . 123.8(5) ?
C25 C24 C23 . . 121.4(5) ?
C26 C25 C24 . . 120.0(5) ?
C25 C26 C27 . . 119.5(5) ?
C28 C27 C26 . . 119.9(6) ?
C27 C28 C23 . . 122.1(5) ?
C27 C28 I2 . . 119.2(4) ?
C23 C28 I2 . . 118.7(4) ?
C31 C30 C29 . . 113.2(12) ?
C30 C31 C32 . . 112.8(15) ?
C33 C32 N2 . . 118.6(8) ?
C33 C32 C31 . . 125.9(10) ?
N2 C32 C31 . . 115.5(10) ?
C32 C33 C34 . . 124.1(10) ?
C32 C33 I2 . . 120.2(6) ?
C34 C33 I2 . . 115.7(8) ?
C33 C34 C35 . . 114.0(11) ?
C36 C35 C34 . . 115.4(11) ?
O4 C37 N2 . . 121.8(10) ?
O4 C37 C38 . . 123.8(9) ?
N2 C37 C38 . . 114.4(7) ?
C37 N2 C32 . . 122.3(7) ?
C31A C30A C29A . . 113.4(16) ?
C30A C31A C32A . . 113.1(19) ?
C33A C32A N2A . . 116.4(11) ?
C33A C32A C31A . . 127.9(15) ?
N2A C32A C31A . . 115.7(15) ?
C32A C33A C34A . . 125.9(16) ?
C32A C33A I2 . . 115.1(8) ?
C34A C33A I2 . . 118.9(16) ?
C33A C34A C35A . . 112.2(16) ?
C36A C35A C34A . . 115.1(14) ?
O4A C37A N2A . . 121.8(16) ?
O4A C37A C38A . . 124.0(12) ?
N2A C37A C38A . . 112.9(11) ?
C37A N2A C32A . . 121.8(11) ?
C28 I2 C33A . . 98.6(5) ?
C28 I2 C33 . . 91.1(3) ?
C28 I2 O3 . . 73.84(17) ?
C33A I2 O3 . . 168.9(4) ?
C33 I2 O3 . . 159.0(2) ?
C22 O3 I2 . . 113.3(3) ?

