# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_iotfi
_database_code_depnum_ccdc_archive 'CCDC 1825325'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 I2 N2, C H4 O, 2(I)'
_chemical_formula_sum            'C23 H20 I4 N2 O'
_chemical_formula_weight         848.01
_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'
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'

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

_cell_length_a                   7.3405(3)
_cell_length_b                   11.1063(4)
_cell_length_c                   16.7600(7)
_cell_angle_alpha                83.668(2)
_cell_angle_beta                 77.493(2)
_cell_angle_gamma                78.301(2)
_cell_volume                     1303.08(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.339
_cell_measurement_theta_min      2.913
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    4.799
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0989 before and 0.0691 after correction. The Ratio of minimum to maximum transmission is 0.7311. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            48949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         2.892
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5111
_reflns_number_total             6498
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.059
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         6498
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.155
_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)+(0.0332P)²+9.4105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1A
 0.84 with sigma of 0.02
 H1A-C23
 1.85 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17),
 C18(H18), C20(H20)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.79634(6) 0.88949(4) 0.49685(3) 0.01864(11) Uani 1 1 d . . . . .
I2 I 0.70808(7) 0.56299(4) 0.78128(3) 0.02306(12) Uani 1 1 d . . . . .
I3 I 0.64252(6) 0.87641(4) 0.71042(3) 0.02126(12) Uani 1 1 d . . . . .
N1 N 0.8829(7) 1.0613(5) 0.2527(4) 0.0162(12) Uani 1 1 d . . . . .
N2 N 0.6547(8) 0.2449(5) 0.9492(4) 0.0215(13) Uani 1 1 d . . . . .
C1 C 0.8722(9) 1.0333(6) 0.3340(4) 0.0179(14) Uani 1 1 d . . . . .
H1 H 0.8822 1.0943 0.3676 0.021 Uiso 1 1 calc R . . . .
C2 C 0.8470(9) 0.9177(6) 0.3691(4) 0.0194(14) Uani 1 1 d . . . . .
C3 C 0.8361(9) 0.8288(6) 0.3176(4) 0.0183(14) Uani 1 1 d . . . . .
C4 C 0.8524(10) 0.8616(6) 0.2336(5) 0.0221(15) Uani 1 1 d . . . . .
H4 H 0.8498 0.8021 0.1974 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8718(10) 0.9780(6) 0.2036(4) 0.0208(15) Uani 1 1 d . . . . .
H5 H 0.8775 1.0001 0.1468 0.025 Uiso 1 1 calc R . . . .
C6 C 0.8105(9) 0.7067(6) 0.3494(4) 0.0200(14) Uani 1 1 d . . . . .
C7 C 0.7845(9) 0.6076(6) 0.3785(4) 0.0198(14) Uani 1 1 d . . . . .
C8 C 0.7433(9) 0.4916(6) 0.4174(4) 0.0158(13) Uani 1 1 d . . . . .
C9 C 0.6751(9) 0.4138(6) 0.3755(4) 0.0185(14) Uani 1 1 d . . . . .
H9 H 0.6651 0.4349 0.3199 0.022 Uiso 1 1 calc R . . . .
C10 C 0.6218(10) 0.3064(6) 0.4146(5) 0.0218(15) Uani 1 1 d . . . . .
H10 H 0.5746 0.2540 0.3860 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6375(9) 0.2749(6) 0.4958(4) 0.0179(14) Uani 1 1 d . . . . .
H11 H 0.6029 0.2004 0.5222 0.022 Uiso 1 1 calc R . . . .
C12 C 0.7575(9) 0.4606(6) 0.4984(4) 0.0163(13) Uani 1 1 d . . . . .
H12 H 0.8041 0.5135 0.5267 0.020 Uiso 1 1 calc R . . . .
C13 C 0.7044(9) 0.3529(6) 0.5390(4) 0.0165(13) Uani 1 1 d . . . . .
C14 C 0.7053(9) 0.3254(6) 0.6238(4) 0.0176(14) Uani 1 1 d . . . . .
C15 C 0.6974(9) 0.3089(6) 0.6958(4) 0.0177(14) Uani 1 1 d . . . . .
C16 C 0.6862(9) 0.2882(6) 0.7822(4) 0.0205(14) Uani 1 1 d . . . . .
C17 C 0.6597(9) 0.1720(6) 0.8215(5) 0.0205(15) Uani 1 1 d . . . . .
H17 H 0.6518 0.1072 0.7906 0.025 Uiso 1 1 calc R . . . .
C18 C 0.6454(10) 0.1536(6) 0.9040(5) 0.0235(16) Uani 1 1 d . . . . .
H18 H 0.6286 0.0752 0.9304 0.028 Uiso 1 1 calc R . . . .
C19 C 0.6946(10) 0.3815(6) 0.8309(4) 0.0216(15) Uani 1 1 d . . . . .
C20 C 0.6795(10) 0.3570(6) 0.9138(5) 0.0230(15) Uani 1 1 d . . . . .
H20 H 0.6866 0.4197 0.9466 0.028 Uiso 1 1 calc R . . . .
C21 C 0.8919(11) 1.1895(6) 0.2202(5) 0.0225(15) Uani 1 1 d . . . . .
H21A H 0.7629 1.2364 0.2219 0.034 Uiso 1 1 calc GR . . . .
H21B H 0.9627 1.1898 0.1635 0.034 Uiso 1 1 calc GR . . . .
H21C H 0.9561 1.2274 0.2537 0.034 Uiso 1 1 calc GR . . . .
C22 C 0.6260(11) 0.2213(7) 1.0390(4) 0.0280(17) Uani 1 1 d . . . . .
H22A H 0.4899 0.2285 1.0622 0.042 Uiso 1 1 calc GR . . . .
H22B H 0.6770 0.2816 1.0620 0.042 Uiso 1 1 calc GR . . . .
H22C H 0.6918 0.1380 1.0525 0.042 Uiso 1 1 calc GR . . . .
I4 I 0.15657(7) 0.16095(4) 0.99132(3) 0.02362(12) Uani 1 1 d . . . . .
O1 O 0.2596(8) 0.4584(5) 0.9597(4) 0.0328(13) Uani 1 1 d D . . . .
H1A H 0.213(9) 0.398(5) 0.983(3) 0.03(2) Uiso 1 1 d D . . . .
C23 C 0.1747(12) 0.4957(7) 0.8918(5) 0.036(2) Uani 1 1 d D . . . .
H23A H 0.2710 0.4826 0.8415 0.053 Uiso 1 1 calc GR . . . .
H23B H 0.1173 0.5834 0.8934 0.053 Uiso 1 1 calc GR . . . .
H23C H 0.0762 0.4474 0.8930 0.053 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
I1 C2 2.092(7) . ?
I2 C19 2.107(7) . ?
N1 C1 1.353(9) . ?
N1 C5 1.329(9) . ?
N1 C21 1.477(8) . ?
N2 C18 1.351(9) . ?
N2 C20 1.348(9) . ?
N2 C22 1.476(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(9) . ?
C2 C3 1.406(10) . ?
C3 C4 1.400(10) . ?
C3 C6 1.434(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.358(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.189(9) . ?
C7 C8 1.436(9) . ?
C8 C9 1.397(9) . ?
C8 C12 1.385(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(10) . ?
C11 H11 0.9500 . ?
C11 C13 1.407(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(9) . ?
C13 C14 1.422(10) . ?
C14 C15 1.190(10) . ?
C15 C16 1.428(10) . ?
C16 C17 1.413(9) . ?
C16 C19 1.407(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.360(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(10) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1 H1A 0.84(2) . ?
O1 C23 1.398(10) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 N1 C21 118.5(6) . . ?
C5 N1 C1 121.1(6) . . ?
C5 N1 C21 120.2(6) . . ?
C18 N2 C22 118.3(6) . . ?
C20 N2 C18 121.1(6) . . ?
C20 N2 C22 120.5(6) . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.2(6) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 I1 118.6(5) . . ?
C1 C2 C3 118.1(6) . . ?
C3 C2 I1 123.0(5) . . ?
C2 C3 C6 121.3(6) . . ?
C4 C3 C2 118.4(6) . . ?
C4 C3 C6 120.2(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(7) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 120.8(7) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C3 177.4(8) . . ?
C6 C7 C8 176.3(8) . . ?
C9 C8 C7 120.0(6) . . ?
C12 C8 C7 120.2(6) . . ?
C12 C8 C9 119.7(6) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(7) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C13 120.4(6) . . ?
C13 C11 H11 119.8 . . ?
C8 C12 H12 119.5 . . ?
C8 C12 C13 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C13 C14 120.1(6) . . ?
C12 C13 C11 118.7(6) . . ?
C12 C13 C14 121.1(6) . . ?
C15 C14 C13 175.9(7) . . ?
C14 C15 C16 179.3(7) . . ?
C17 C16 C15 119.8(6) . . ?
C19 C16 C15 122.1(6) . . ?
C19 C16 C17 118.0(7) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.5(7) . . ?
C18 C17 H17 120.2 . . ?
N2 C18 C17 121.1(7) . . ?
N2 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C16 C19 I2 121.7(5) . . ?
C20 C19 I2 118.6(5) . . ?
C20 C19 C16 119.6(6) . . ?
N2 C20 C19 120.7(7) . . ?
N2 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O1 H1A 105(3) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_iotfbr
_database_code_depnum_ccdc_archive 'CCDC 1825329'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 I2 N2, C H4 O, 2(Br)'
_chemical_formula_sum            'C23 H20 Br2 I2 N2 O'
_chemical_formula_weight         754.03
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   7.2800(2)
_cell_length_b                   10.9585(4)
_cell_length_c                   16.0936(6)
_cell_angle_alpha                89.7580(10)
_cell_angle_beta                 79.7350(10)
_cell_angle_gamma                78.5410(10)
_cell_volume                     1237.53(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.386
_cell_measurement_theta_min      3.132
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.787
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0796 before and 0.0533 after correction. The Ratio of minimum to maximum transmission is 0.7790. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         2.903
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4458
_reflns_number_total             5654
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+1.4402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0587
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17),
 C18(H18), C20(H20)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.50095(3) 0.55831(2) 0.22315(2) 0.02391(7) Uani 1 1 d . . . . .
I2 I 0.29280(3) 0.89136(2) 0.50552(2) 0.01932(6) Uani 1 1 d . . . . .
N1 N 0.6137(4) 0.2358(3) 0.05653(18) 0.0225(7) Uani 1 1 d . . . . .
N2 N 0.1307(4) 1.0680(3) 0.75309(18) 0.0208(6) Uani 1 1 d . . . . .
C1 C 0.6048(5) 0.3497(3) 0.0905(2) 0.0230(8) Uani 1 1 d . . . . .
H1 H 0.6468 0.4128 0.0558 0.028 Uiso 1 1 calc R . . . .
C2 C 0.5346(5) 0.3748(3) 0.1760(2) 0.0207(7) Uani 1 1 d . . . . .
C3 C 0.4739(5) 0.2806(3) 0.2266(2) 0.0195(7) Uani 1 1 d . . . . .
C4 C 0.4860(5) 0.1633(3) 0.1888(2) 0.0226(8) Uani 1 1 d . . . . .
H4 H 0.4462 0.0980 0.2218 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5559(5) 0.1438(3) 0.1037(2) 0.0242(8) Uani 1 1 d . . . . .
H5 H 0.5636 0.0647 0.0779 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3986(5) 0.3024(3) 0.3145(2) 0.0207(7) Uani 1 1 d . . . . .
C7 C 0.3310(5) 0.3203(3) 0.3877(2) 0.0203(7) Uani 1 1 d . . . . .
C8 C 0.2372(5) 0.3493(3) 0.4728(2) 0.0180(7) Uani 1 1 d . . . . .
C9 C 0.1208(5) 0.2717(3) 0.5148(2) 0.0192(7) Uani 1 1 d . . . . .
H9 H 0.1153 0.1953 0.4885 0.023 Uiso 1 1 calc R . . . .
C10 C 0.0146(5) 0.3061(3) 0.5941(2) 0.0207(7) Uani 1 1 d . . . . .
H10 H -0.0664 0.2545 0.6217 0.025 Uiso 1 1 calc R . . . .
C11 C 0.0259(5) 0.4156(3) 0.6335(2) 0.0203(7) Uani 1 1 d . . . . .
H11 H -0.0462 0.4383 0.6883 0.024 Uiso 1 1 calc R . . . .
C12 C 0.2487(5) 0.4604(3) 0.5125(2) 0.0179(7) Uani 1 1 d . . . . .
H12 H 0.3280 0.5129 0.4847 0.022 Uiso 1 1 calc R . . . .
C13 C 0.1428(5) 0.4932(3) 0.5931(2) 0.0179(7) Uani 1 1 d . . . . .
C14 C 0.1420(5) 0.6113(3) 0.6309(2) 0.0205(7) Uani 1 1 d . . . . .
C15 C 0.1350(5) 0.7134(3) 0.6582(2) 0.0197(7) Uani 1 1 d . . . . .
C16 C 0.1305(5) 0.8353(3) 0.6894(2) 0.0193(7) Uani 1 1 d . . . . .
C17 C 0.0554(5) 0.8696(3) 0.7739(2) 0.0226(8) Uani 1 1 d . . . . .
H17 H 0.0038 0.8119 0.8107 0.027 Uiso 1 1 calc R . . . .
C18 C 0.0558(5) 0.9861(3) 0.8040(2) 0.0234(8) Uani 1 1 d . . . . .
H18 H 0.0026 1.0092 0.8614 0.028 Uiso 1 1 calc R . . . .
C19 C 0.2031(5) 0.9239(3) 0.6365(2) 0.0179(7) Uani 1 1 d . . . . .
C20 C 0.2055(5) 1.0386(3) 0.6711(2) 0.0204(7) Uani 1 1 d . . . . .
H20 H 0.2604 1.0975 0.6367 0.024 Uiso 1 1 calc R . . . .
C21 C 0.6767(6) 0.2135(4) -0.0354(2) 0.0313(9) Uani 1 1 d . . . . .
H21A H 0.5653 0.2278 -0.0632 0.047 Uiso 1 1 calc GR . . . .
H21B H 0.7461 0.1272 -0.0468 0.047 Uiso 1 1 calc GR . . . .
H21C H 0.7605 0.2705 -0.0572 0.047 Uiso 1 1 calc GR . . . .
C22 C 0.1214(6) 1.1946(3) 0.7858(2) 0.0272(9) Uani 1 1 d . . . . .
H22A H 0.2169 1.2325 0.7498 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.1470 1.1907 0.8436 0.041 Uiso 1 1 calc GR . . . .
H22C H -0.0058 1.2451 0.7858 0.041 Uiso 1 1 calc GR . . . .
Br1 Br 0.36768(6) 0.86069(4) 0.29193(2) 0.02931(10) Uani 1 1 d . . . . .
Br2 Br 0.16921(6) 0.15430(4) 0.00901(2) 0.02727(9) Uani 1 1 d . . . . .
O1 O 0.2303(4) 0.4412(3) 0.03478(19) 0.0329(7) Uani 1 1 d . . . . .
H1A H 0.216(7) 0.377(4) 0.019(3) 0.037(14) Uiso 1 1 d . . . . .
C23 C 0.0837(6) 0.4788(4) 0.1057(3) 0.0377(10) Uani 1 1 d . . . . .
H23A H -0.0340 0.4558 0.0956 0.057 Uiso 1 1 calc GR . . . .
H23B H 0.0624 0.5692 0.1148 0.057 Uiso 1 1 calc GR . . . .
H23C H 0.1213 0.4372 0.1559 0.057 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
I1 C2 2.105(3) . ?
I2 C19 2.103(3) . ?
N1 C1 1.350(5) . ?
N1 C5 1.348(5) . ?
N1 C21 1.474(5) . ?
N2 C18 1.344(5) . ?
N2 C20 1.349(4) . ?
N2 C22 1.471(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(5) . ?
C2 C3 1.403(5) . ?
C3 C4 1.405(5) . ?
C3 C6 1.427(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.194(5) . ?
C7 C8 1.423(5) . ?
C8 C9 1.406(5) . ?
C8 C12 1.401(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
C11 H11 0.9500 . ?
C11 C13 1.398(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(5) . ?
C13 C14 1.431(5) . ?
C14 C15 1.191(5) . ?
C15 C16 1.422(5) . ?
C16 C17 1.396(5) . ?
C16 C19 1.408(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1 H1A 0.78(5) . ?
O1 C23 1.417(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 N1 C21 119.3(3) . . ?
C5 N1 C1 121.7(3) . . ?
C5 N1 C21 118.9(3) . . ?
C18 N2 C20 121.2(3) . . ?
C18 N2 C22 119.5(3) . . ?
C20 N2 C22 119.1(3) . . ?
N1 C1 H1 119.9 . . ?
N1 C1 C2 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C1 C2 I1 118.4(3) . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 I1 122.0(3) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 C6 121.5(3) . . ?
C4 C3 C6 119.8(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C3 178.3(4) . . ?
C6 C7 C8 175.0(4) . . ?
C9 C8 C7 120.1(3) . . ?
C12 C8 C7 119.9(3) . . ?
C12 C8 C9 119.8(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C13 120.5(3) . . ?
C13 C11 H11 119.7 . . ?
C8 C12 H12 120.3 . . ?
C13 C12 C8 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C13 C14 120.3(3) . . ?
C12 C13 C11 119.9(3) . . ?
C12 C13 C14 119.5(3) . . ?
C15 C14 C13 175.5(4) . . ?
C14 C15 C16 178.8(4) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 C19 118.3(3) . . ?
C19 C16 C15 121.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
N2 C18 C17 120.5(3) . . ?
N2 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C19 I2 122.2(2) . . ?
C20 C19 I2 118.8(3) . . ?
C20 C19 C16 118.9(3) . . ?
N2 C20 C19 120.7(3) . . ?
N2 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O1 H1A 106(3) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Br2 0.78(5) 2.54(5) 3.300(3) 165(4) .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_g2xbmeotf
_database_code_depnum_ccdc_archive 'CCDC 1825328'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F I2 N3, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H16 F7 I2 N3 O6 S2'
_chemical_formula_weight         893.32
_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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0582(3)
_cell_length_b                   11.0044(4)
_cell_length_c                   17.7067(6)
_cell_angle_alpha                99.618(2)
_cell_angle_beta                 91.239(2)
_cell_angle_gamma                104.624(2)
_cell_volume                     1494.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.026
_cell_measurement_theta_min      2.938
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.561
_exptl_absorpt_coefficient_mu    2.332
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0631 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.8920. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44120
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.087
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_min         2.938
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4480
_reflns_number_total             5299
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     527
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.058
_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)+(0.0426P)²+3.6052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0895
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F5-C24 \\sim F5'-C24
 with sigma of 0.02
 S1-C23 \\sim S1'-C23'
 with sigma of 0.02
 S1-O3 \\sim S1'-O3' \\sim S1-O1 \\sim S1'-O1' \\sim S1-O2 \\sim S1'-O2'
 with sigma of 0.02
 F3-C23 \\sim F3'-C23' \\sim F4-C23 \\sim F4'-C23' \\sim F2-C23 \\sim F2'-C23'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C23')
Uanis(C5) = Uanis(C5')
Uanis(C24') = Uanis(C24)
Uanis(O5) = Uanis(O5')
4. Rigid body (RIGU) restrains
 S1', O1', O2', O3', C23', F2', F3', F4'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2, S1, O1, O3, C23, F2, F3, F4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, S2, O4, C24, F5, F7, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4', S2', O5', O6', C24', F5', F6, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, I1, C1, C5, C2, C4, C6, N3, H2, H4, C3, C7, C5', C21, H3, C8, C1', C0AA,
 H21A, H21B, H21C, C9, I1', C2', C3', H0AA, H9, C10, N2, C13, H2', N3', H3', F1,
  C11, H2A, H2B, C14, C21', H11, C15, H21D, H21E, H21F, C16, C17, C19, H17, C18,
  I2, C20, N1, H18, H20, C22, H22A, H22B, H22C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(I1')=Sof(S2')=Sof(F5')=Sof(O4')=Sof(O5')=Sof(O6')=Sof(C5')=Sof(C1')=
 Sof(C2')=Sof(H2')=Sof(N3')=Sof(C3')=Sof(H3')=Sof(C0AA)=Sof(H0AA)=Sof(C21')=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C24')=Sof(S1')=Sof(F2')=Sof(F3')=Sof(F4')=
 Sof(O1')=Sof(O2')=Sof(O3')=Sof(C23')=1-FVAR(1)
 Sof(I1)=Sof(S2)=Sof(F5)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(C5)=Sof(C4)=Sof(H4)=
 Sof(C3)=Sof(H3)=Sof(N3)=Sof(C2)=Sof(H2)=Sof(C1)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(H21C)=Sof(C24)=Sof(S1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(O1)=Sof(O2)=Sof(O3)=
 Sof(C23)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C9(H9), C11(H11), C17(H17), C18(H18), C20(H20),
 C2'(H2'), C3'(H3'), C0AA(H0AA)
6.b Fitted hexagon refined as free rotating group:
 C5(C4,C3,N3,C2,C1), C5'(C1',C2',N3',C3',C0AA)
6.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C21'(H21D,H21E,H21F)
;
_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 0.98055(8) 0.41741(6) 0.77576(3) 0.0390(2) Uani 0.5109(10) 1 d . U P A 1
I2 I 0.48322(4) 0.17761(3) 0.50134(2) 0.02947(10) Uani 1 1 d . U . . .
S2 S 0.5161(4) 0.1383(2) 0.71847(14) 0.0438(6) Uani 0.5109(10) 1 d . U P A 1
F1 F 1.0859(4) 0.9194(3) 0.45838(17) 0.0454(7) Uani 1 1 d . U . . .
F5 F 0.2780(11) 0.2400(8) 0.7659(6) 0.088(3) Uani 0.5109(10) 1 d D U P A 1
F6 F 0.4401(5) 0.3523(3) 0.68964(19) 0.0651(9) Uani 1 1 d . U . . .
F7 F 0.5053(5) 0.3637(4) 0.80750(18) 0.0734(10) Uani 1 1 d . U . . .
O4 O 0.5261(13) 0.0839(8) 0.7857(4) 0.067(2) Uani 0.5109(10) 1 d . U P A 1
O5 O 0.6650(14) 0.1951(10) 0.6854(6) 0.0600(19) Uani 0.5109(10) 1 d . . P A 1
O6 O 0.3972(14) 0.0633(7) 0.6604(5) 0.081(3) Uani 0.5109(10) 1 d . U P A 1
N1 N 0.2044(5) 0.1157(4) 0.2846(2) 0.0315(8) Uani 1 1 d . U . . .
N2 N 0.8251(5) 0.4953(3) 0.5880(2) 0.0289(8) Uani 1 1 d . U . . .
H2A H 0.7426 0.4321 0.5628 0.035 Uiso 1 1 calc R U . . .
H2B H 0.8650 0.4907 0.6338 0.035 Uiso 1 1 calc R U . . .
C5 C 1.208(2) 0.6881(15) 0.8038(7) 0.0385(17) Uani 0.5109(10) 1 d . U P A 1
C4 C 1.316(2) 0.7985(12) 0.8466(8) 0.052(4) Uani 0.5109(10) 1 d G U P A 1
H4 H 1.3517 0.8730 0.8245 0.063 Uiso 0.5109(10) 1 calc R U P A 1
C3 C 1.3701(16) 0.7999(9) 0.9219(7) 0.056(4) Uani 0.5109(10) 1 d G U P A 1
H3 H 1.4434 0.8754 0.9512 0.067 Uiso 0.5109(10) 1 calc R U P A 1
N3 N 1.3174(15) 0.6909(10) 0.9543(6) 0.045(3) Uani 0.5109(10) 1 d G U P A 1
C2 C 1.2102(17) 0.5805(9) 0.9115(7) 0.037(3) Uani 0.5109(10) 1 d G U P A 1
H2 H 1.1742 0.5060 0.9336 0.044 Uiso 0.5109(10) 1 calc R U P A 1
C1 C 1.156(2) 0.5790(12) 0.8362(7) 0.040(3) Uani 0.5109(10) 1 d G U P A 1
C6 C 1.1459(6) 0.6886(5) 0.7308(3) 0.0381(11) Uani 1 1 d . U . . .
C7 C 1.0900(6) 0.6975(4) 0.6696(3) 0.0344(10) Uani 1 1 d . U . . .
C8 C 1.0219(5) 0.7046(4) 0.5961(2) 0.0288(9) Uani 1 1 d . U . . .
C9 C 1.0849(6) 0.8126(4) 0.5626(3) 0.0344(10) Uani 1 1 d . U . . .
H9 H 1.1709 0.8833 0.5896 0.041 Uiso 1 1 calc R U . . .
C10 C 1.0215(6) 0.8155(4) 0.4908(3) 0.0325(9) Uani 1 1 d . U . . .
C11 C 0.8965(6) 0.7170(4) 0.4499(3) 0.0295(9) Uani 1 1 d . U . . .
H11 H 0.8564 0.7217 0.3999 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8907(5) 0.5997(4) 0.5562(2) 0.0254(8) Uani 1 1 d . U . . .
C13 C 0.8283(5) 0.6089(4) 0.4825(2) 0.0245(8) Uani 1 1 d . U . . .
C14 C 0.6969(5) 0.5065(4) 0.4414(2) 0.0254(8) Uani 1 1 d . U . . .
C15 C 0.5854(5) 0.4183(4) 0.4082(2) 0.0257(8) Uani 1 1 d . U . . .
C16 C 0.4575(5) 0.3148(4) 0.3666(2) 0.0245(8) Uani 1 1 d . U . . .
C17 C 0.3866(6) 0.3227(4) 0.2949(2) 0.0282(9) Uani 1 1 d . U . . .
H17 H 0.4263 0.3977 0.2736 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2608(6) 0.2229(4) 0.2556(2) 0.0328(10) Uani 1 1 d . U . . .
H18 H 0.2128 0.2296 0.2075 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3949(5) 0.2003(4) 0.3950(2) 0.0233(8) Uani 1 1 d . U . . .
C20 C 0.2696(5) 0.1023(4) 0.3523(2) 0.0270(9) Uani 1 1 d . U . . .
H20 H 0.2290 0.0247 0.3709 0.032 Uiso 1 1 calc R U . . .
C21 C 1.355(2) 0.6874(16) 1.0350(8) 0.055(4) Uani 0.5109(10) 1 d . U P A 1
H21A H 1.4192 0.7726 1.0612 0.083 Uiso 0.5109(10) 1 calc GR U P A 1
H21B H 1.4246 0.6268 1.0382 0.083 Uiso 0.5109(10) 1 calc GR U P A 1
H21C H 1.2474 0.6605 1.0595 0.083 Uiso 0.5109(10) 1 calc GR U P A 1
C22 C 0.0651(7) 0.0088(5) 0.2419(3) 0.0528(14) Uani 1 1 d . U . . .
H22A H 0.1118 -0.0638 0.2231 0.079 Uiso 1 1 calc GR U . . .
H22B H 0.0177 0.0367 0.1983 0.079 Uiso 1 1 calc GR U . . .
H22C H -0.0261 -0.0168 0.2762 0.079 Uiso 1 1 calc GR U . . .
C24 C 0.434(2) 0.2856(18) 0.7517(9) 0.0419(18) Uani 0.5109(10) 1 d D U P A 1
I1' I 1.42995(8) 0.93655(6) 0.82480(4) 0.0379(2) Uani 0.4891(10) 1 d . U P A 2
S2' S 0.6741(3) 0.2415(3) 0.72298(17) 0.0352(6) Uani 0.4891(10) 1 d . U P A 2
F5' F 0.3401(11) 0.1960(8) 0.7392(5) 0.066(2) Uani 0.4891(10) 1 d D U P A 2
O4' O 0.8029(11) 0.3605(8) 0.7244(5) 0.061(2) Uani 0.4891(10) 1 d . U P A 2
O5' O 0.6290(14) 0.1596(10) 0.6487(5) 0.0600(19) Uani 0.4891(10) 1 d . U P A 2
O6' O 0.6835(10) 0.1770(7) 0.7857(4) 0.0425(16) Uani 0.4891(10) 1 d . U P A 2
C5' C 1.207(2) 0.6664(15) 0.8058(7) 0.0385(17) Uani 0.4891(10) 1 d . U P A 2
C1' C 1.3151(18) 0.7671(11) 0.8560(7) 0.031(2) Uani 0.4891(10) 1 d G U P A 2
C2' C 1.3558(13) 0.7523(8) 0.9301(6) 0.030(3) Uani 0.4891(10) 1 d G U P A 2
H2' H 1.4300 0.8211 0.9644 0.036 Uiso 0.4891(10) 1 calc R U P A 2
N3' N 1.2879(15) 0.6367(10) 0.9539(6) 0.040(3) Uani 0.4891(10) 1 d G U P A 2
C3' C 1.1793(19) 0.5360(9) 0.9036(8) 0.048(4) Uani 0.4891(10) 1 d G U P A 2
H3' H 1.1328 0.4570 0.9199 0.058 Uiso 0.4891(10) 1 calc R U P A 2
C0AA C 1.139(2) 0.5509(13) 0.8296(8) 0.044(4) Uani 0.4891(10) 1 d G U P A 2
H0AA H 1.0644 0.4820 0.7953 0.052 Uiso 0.4891(10) 1 calc R U P A 2
C21' C 1.325(3) 0.6239(17) 1.0337(10) 0.058(5) Uani 0.4891(10) 1 d . U P A 2
H21D H 1.4403 0.6108 1.0390 0.087 Uiso 0.4891(10) 1 calc GR U P A 2
H21E H 1.2400 0.5507 1.0466 0.087 Uiso 0.4891(10) 1 calc GR U P A 2
H21F H 1.3196 0.7017 1.0686 0.087 Uiso 0.4891(10) 1 calc GR U P A 2
C24' C 0.476(2) 0.2878(18) 0.7383(9) 0.0419(18) Uani 0.4891(10) 1 d . U P A 2
S1 S 0.8581(8) 0.7472(5) 0.9541(4) 0.0478(13) Uani 0.5109(10) 1 d D U P A 1
F2 F 0.9863(17) 0.9422(12) 1.0610(8) 0.100(4) Uani 0.5109(10) 1 d D U P A 1
F3 F 0.750(2) 0.9407(15) 1.0000(8) 0.094(4) Uani 0.5109(10) 1 d D U P A 1
F4 F 0.748(2) 0.8222(15) 1.0877(9) 0.123(5) Uani 0.5109(10) 1 d D U P A 1
O1 O 0.6833(15) 0.6802(17) 0.9258(11) 0.049(3) Uani 0.5109(10) 1 d D U P A 1
O2 O 0.9485(15) 0.6757(12) 0.9934(8) 0.075(4) Uani 0.5109(10) 1 d D U P A 1
O3 O 0.9572(19) 0.8157(11) 0.9013(8) 0.048(3) Uani 0.5109(10) 1 d D U P A 1
C23 C 0.8353(19) 0.8692(14) 1.0317(7) 0.070(3) Uani 0.5109(10) 1 d D U P A 1
S1' S 0.8292(8) 0.6931(5) 0.9497(4) 0.0434(12) Uani 0.4891(10) 1 d D U P A 2
F2' F 1.0006(16) 0.8712(13) 1.0590(8) 0.093(4) Uani 0.4891(10) 1 d D U P A 2
F3' F 0.7614(19) 0.9045(13) 1.0232(7) 0.074(3) Uani 0.4891(10) 1 d D U P A 2
F4' F 0.7635(19) 0.7598(13) 1.0898(7) 0.085(3) Uani 0.4891(10) 1 d D U P A 2
O1' O 0.6494(17) 0.6434(19) 0.9296(13) 0.062(4) Uani 0.4891(10) 1 d D U P A 2
O2' O 0.9090(15) 0.6057(11) 0.9773(7) 0.063(3) Uani 0.4891(10) 1 d D U P A 2
O3' O 0.9302(19) 0.7635(12) 0.8969(7) 0.044(3) Uani 0.4891(10) 1 d D U P A 2
C23' C 0.8395(18) 0.8133(14) 1.0324(7) 0.070(3) Uani 0.4891(10) 1 d D U 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 C1 2.082(10) . ?
I2 C19 2.076(4) . ?
S2 O4 1.428(8) . ?
S2 O5 1.396(11) . ?
S2 O6 1.390(8) . ?
S2 C24 1.912(16) . ?
F1 C10 1.356(5) . ?
F5 C24 1.275(18) . ?
F6 C24 1.415(17) . ?
F6 C24' 1.276(18) . ?
F7 C24 1.221(19) . ?
F7 C24' 1.341(17) . ?
N1 C18 1.342(6) . ?
N1 C20 1.345(6) . ?
N1 C22 1.488(6) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C12 1.355(5) . ?
C5 C4 1.3900 . ?
C5 C1 1.3900 . ?
C5 C6 1.379(10) . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 N3 1.3900 . ?
N3 C2 1.3900 . ?
N3 C21 1.463(15) . ?
C2 H2 0.9500 . ?
C2 C1 1.3900 . ?
C6 C7 1.192(7) . ?
C6 C5' 1.485(11) . ?
C7 C8 1.424(6) . ?
C8 C9 1.402(6) . ?
C8 C12 1.424(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.369(7) . ?
C10 C11 1.367(6) . ?
C11 H11 0.9500 . ?
C11 C13 1.401(6) . ?
C12 C13 1.418(6) . ?
C13 C14 1.418(6) . ?
C14 C15 1.200(6) . ?
C15 C16 1.413(6) . ?
C16 C17 1.406(6) . ?
C16 C19 1.412(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(6) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
I1' C1' 2.033(10) . ?
S2' O4' 1.447(8) . ?
S2' O5' 1.447(9) . ?
S2' O6' 1.426(7) . ?
S2' C24' 1.804(16) . ?
F5' C24' 1.29(2) . ?
C5' C1' 1.3900 . ?
C5' C0AA 1.3900 . ?
C1' C2' 1.3900 . ?
C2' H2' 0.9500 . ?
C2' N3' 1.3900 . ?
N3' C3' 1.3900 . ?
N3' C21' 1.476(15) . ?
C3' H3' 0.9500 . ?
C3' C0AA 1.3900 . ?
C0AA H0AA 0.9500 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
S1 O1 1.449(10) . ?
S1 O2 1.444(9) . ?
S1 O3 1.429(9) . ?
S1 C23 1.801(14) . ?
F2 C23 1.317(12) . ?
F3 C23 1.348(13) . ?
F4 C23 1.327(12) . ?
S1' O1' 1.428(11) . ?
S1' O2' 1.425(9) . ?
S1' O3' 1.446(9) . ?
S1' C23' 1.787(13) . ?
F2' C23' 1.330(12) . ?
F3' C23' 1.342(12) . ?
F4' C23' 1.341(12) . ?

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
O4 S2 C24 105.0(6) . . ?
O5 S2 O4 120.7(6) . . ?
O5 S2 C24 99.5(7) . . ?
O6 S2 O4 115.3(6) . . ?
O6 S2 O5 108.7(7) . . ?
O6 S2 C24 105.2(7) . . ?
C18 N1 C20 121.5(4) . . ?
C18 N1 C22 120.0(4) . . ?
C20 N1 C22 118.5(4) . . ?
H2A N2 H2B 120.0 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
C4 C5 C1 120.0 . . ?
C6 C5 C4 120.1(9) . . ?
C6 C5 C1 119.8(9) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
N3 C3 C4 120.0 . . ?
N3 C3 H3 120.0 . . ?
C3 N3 C2 120.0 . . ?
C3 N3 C21 123.5(9) . . ?
C2 N3 C21 116.2(9) . . ?
N3 C2 H2 120.0 . . ?
N3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C5 C1 I1 120.4(7) . . ?
C2 C1 I1 119.4(7) . . ?
C2 C1 C5 120.0 . . ?
C7 C6 C5 175.3(9) . . ?
C7 C6 C5' 175.2(8) . . ?
C6 C7 C8 178.5(5) . . ?
C7 C8 C12 119.2(4) . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 C12 120.2(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9 120.2 . . ?
F1 C10 C9 118.9(4) . . ?
F1 C10 C11 118.5(4) . . ?
C11 C10 C9 122.5(4) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C13 119.3(4) . . ?
C13 C11 H11 120.3 . . ?
N2 C12 C8 121.4(4) . . ?
N2 C12 C13 120.9(4) . . ?
C13 C12 C8 117.7(4) . . ?
C11 C13 C12 120.6(4) . . ?
C11 C13 C14 120.1(4) . . ?
C12 C13 C14 119.2(4) . . ?
C15 C14 C13 178.4(4) . . ?
C14 C15 C16 177.9(4) . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 C19 117.3(4) . . ?
C19 C16 C15 121.9(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
N1 C18 C17 120.6(4) . . ?
N1 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C19 I2 121.4(3) . . ?
C20 C19 I2 118.9(3) . . ?
C20 C19 C16 119.7(4) . . ?
N1 C20 C19 120.5(4) . . ?
N1 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F5 C24 S2 104.2(12) . . ?
F5 C24 F6 110.2(13) . . ?
F6 C24 S2 107.7(8) . . ?
F7 C24 S2 119.6(11) . . ?
F7 C24 F5 108.4(11) . . ?
F7 C24 F6 106.6(14) . . ?
O4' S2' O5' 115.9(6) . . ?
O4' S2' C24' 104.5(7) . . ?
O5' S2' C24' 99.8(7) . . ?
O6' S2' O4' 116.7(5) . . ?
O6' S2' O5' 115.1(6) . . ?
O6' S2' C24' 101.2(6) . . ?
C1' C5' C6 119.4(9) . . ?
C1' C5' C0AA 120.0 . . ?
C0AA C5' C6 120.2(9) . . ?
C5' C1' I1' 122.8(6) . . ?
C2' C1' I1' 117.1(6) . . ?
C2' C1' C5' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C1' C2' N3' 120.0 . . ?
N3' C2' H2' 120.0 . . ?
C2' N3' C21' 119.6(9) . . ?
C3' N3' C2' 120.0 . . ?
C3' N3' C21' 120.4(8) . . ?
N3' C3' H3' 120.0 . . ?
C0AA C3' N3' 120.0 . . ?
C0AA C3' H3' 120.0 . . ?
C5' C0AA H0AA 120.0 . . ?
C3' C0AA C5' 120.0 . . ?
C3' C0AA H0AA 120.0 . . ?
N3' C21' H21D 109.5 . . ?
N3' C21' H21E 109.5 . . ?
N3' C21' H21F 109.5 . . ?
H21D C21' H21E 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
F6 C24' F7 107.9(13) . . ?
F6 C24' S2' 113.8(10) . . ?
F6 C24' F5' 106.0(13) . . ?
F7 C24' S2' 104.1(11) . . ?
F5' C24' F7 108.7(11) . . ?
F5' C24' S2' 116.0(13) . . ?
O1 S1 C23 104.5(10) . . ?
O2 S1 O1 115.2(9) . . ?
O2 S1 C23 101.3(8) . . ?
O3 S1 O1 114.8(10) . . ?
O3 S1 O2 114.3(9) . . ?
O3 S1 C23 104.5(7) . . ?
F2 C23 S1 111.2(11) . . ?
F2 C23 F3 108.7(13) . . ?
F2 C23 F4 108.6(13) . . ?
F3 C23 S1 105.4(10) . . ?
F4 C23 S1 113.0(11) . . ?
F4 C23 F3 109.8(14) . . ?
O1' S1' O3' 117.0(11) . . ?
O1' S1' C23' 103.8(11) . . ?
O2' S1' O1' 114.2(10) . . ?
O2' S1' O3' 113.3(8) . . ?
O2' S1' C23' 103.4(7) . . ?
O3' S1' C23' 102.8(7) . . ?
F2' C23' S1' 112.0(10) . . ?
F2' C23' F3' 107.4(13) . . ?
F2' C23' F4' 105.7(12) . . ?
F3' C23' S1' 115.6(10) . . ?
F4' C23' S1' 109.8(11) . . ?
F4' C23' F3' 105.7(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O4' 0.88 2.31 3.025(8) 138.9 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_iotfotf
_database_code_depnum_ccdc_archive 'CCDC 1825331'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 I2 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H16 F6 I2 N2 O6 S2'
_chemical_formula_weight         860.31
_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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   22.337(2)
_cell_length_b                   12.7364(13)
_cell_length_c                   10.9081(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3103.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.570
_cell_measurement_theta_min      3.062
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.468
_exptl_absorpt_coefficient_mu    2.237
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0807 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.8418. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            105030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.589
_diffrn_reflns_theta_min         3.061
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3659
_reflns_number_total             4770
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.204
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+5.2883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.33796(2) 0.62070(2) 0.63318(2) 0.02531(7) Uani 1 1 d . . . . .
N1 N 0.28005(12) 0.32830(19) 0.7822(2) 0.0234(5) Uani 1 1 d . . . . .
C1 C 0.28862(14) 0.4307(2) 0.7570(3) 0.0230(6) Uani 1 1 d . . . . .
H1 H 0.2674 0.4824 0.8024 0.028 Uiso 1 1 calc R . . . .
C2 C 0.32790(13) 0.4614(2) 0.6661(3) 0.0207(6) Uani 1 1 d . . . . .
C3 C 0.35870(14) 0.3845(3) 0.5972(3) 0.0248(6) Uani 1 1 d . . . . .
C4 C 0.34852(14) 0.2790(2) 0.6278(3) 0.0255(6) Uani 1 1 d . . . . .
H4 H 0.3689 0.2251 0.5844 0.031 Uiso 1 1 calc R . . . .
C5 C 0.30932(14) 0.2530(2) 0.7202(3) 0.0254(6) Uani 1 1 d . . . . .
H5 H 0.3029 0.1813 0.7402 0.030 Uiso 1 1 calc R . . . .
C6 C 0.39704(14) 0.4152(3) 0.5008(3) 0.0257(6) Uani 1 1 d . . . . .
C7 C 0.42883(14) 0.4519(3) 0.4231(3) 0.0273(7) Uani 1 1 d . . . . .
C8 C 0.46509(13) 0.5053(3) 0.3341(3) 0.0263(6) Uani 1 1 d . . . . .
C9 C 0.5000 0.4501(4) 0.2500 0.0261(9) Uani 1 2 d S T P . .
H9 H 0.5000 0.3755 0.2500 0.031 Uiso 1 2 calc RS T P . .
C10 C 0.46550(15) 0.6153(3) 0.3340(3) 0.0308(7) Uani 1 1 d . . . . .
H10 H 0.4420 0.6528 0.3919 0.037 Uiso 1 1 calc R . . . .
C11 C 0.5000 0.6691(4) 0.2500 0.0343(11) Uani 1 2 d S T P . .
H11 H 0.5000 0.7437 0.2500 0.041 Uiso 1 2 calc RS T P . .
C12 C 0.23364(16) 0.3000(3) 0.8741(3) 0.0303(7) Uani 1 1 d . . . . .
H12A H 0.2322 0.3540 0.9380 0.045 Uiso 1 1 calc GR . . . .
H12B H 0.2436 0.2321 0.9111 0.045 Uiso 1 1 calc GR . . . .
H12C H 0.1946 0.2952 0.8337 0.045 Uiso 1 1 calc GR . . . .
S1 S 0.17108(3) 0.43948(5) 0.53796(7) 0.02388(16) Uani 1 1 d . . . . .
F1 F 0.08490(17) 0.3661(3) 0.4040(4) 0.1016(13) Uani 1 1 d . . . . .
F2 F 0.09133(17) 0.5337(3) 0.4050(4) 0.1083(14) Uani 1 1 d . . . . .
F3 F 0.05622(13) 0.4528(4) 0.5592(5) 0.1146(15) Uani 1 1 d . . . . .
O1 O 0.20890(13) 0.4318(2) 0.4320(2) 0.0445(7) Uani 1 1 d . . . . .
O2 O 0.17816(13) 0.53559(19) 0.6049(3) 0.0398(6) Uani 1 1 d . . . . .
O3 O 0.16903(13) 0.3462(2) 0.6113(3) 0.0447(7) Uani 1 1 d . . . . .
C13 C 0.0965(2) 0.4489(4) 0.4739(5) 0.0611(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.073(3) . ?
N1 C1 1.346(4) . ?
N1 C5 1.344(4) . ?
N1 C12 1.486(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(4) . ?
C2 C3 1.414(4) . ?
C3 C4 1.403(4) . ?
C3 C6 1.412(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.201(5) . ?
C7 C8 1.435(5) . ?
C8 C9 1.394(4) . ?
C8 C10 1.401(5) . ?
C9 C8 1.394(4) 3_655 ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.380(4) . ?
C11 C10 1.380(4) 3_655 ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S1 O1 1.435(3) . ?
S1 O2 1.434(2) . ?
S1 O3 1.433(3) . ?
S1 C13 1.810(4) . ?
F1 C13 1.328(6) . ?
F2 C13 1.320(6) . ?
F3 C13 1.296(7) . ?

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
C1 N1 C12 118.1(3) . . ?
C5 N1 C1 121.3(3) . . ?
C5 N1 C12 120.4(3) . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.7(3) . . ?
C2 C1 H1 119.6 . . ?
C1 C2 I1 118.1(2) . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 I1 122.2(2) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 C6 122.8(3) . . ?
C6 C3 C2 119.9(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 120.4(3) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C3 173.2(3) . . ?
C6 C7 C8 174.6(3) . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 C10 120.0(3) . . ?
C10 C8 C7 118.6(3) . . ?
C8 C9 C8 119.5(4) . 3_655 ?
C8 C9 H9 120.3 . . ?
C8 C9 H9 120.3 3_655 . ?
C8 C10 H10 120.0 . . ?
C11 C10 C8 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C10 120.4(5) . 3_655 ?
C10 C11 H11 119.8 . . ?
C10 C11 H11 119.8 3_655 . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 S1 C13 103.6(2) . . ?
O2 S1 O1 113.78(17) . . ?
O2 S1 C13 104.0(2) . . ?
O3 S1 O1 114.37(17) . . ?
O3 S1 O2 115.23(17) . . ?
O3 S1 C13 104.0(2) . . ?
F1 C13 S1 110.4(4) . . ?
F2 C13 S1 110.8(4) . . ?
F2 C13 F1 107.8(5) . . ?
F3 C13 S1 111.4(4) . . ?
F3 C13 F1 107.8(5) . . ?
F3 C13 F2 108.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_umt_ob20
_database_code_depnum_ccdc_archive 'CCDC 1825330'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F I2 N3, 2(Br)'
_chemical_formula_sum            'C22 H16 Br2 F I2 N3'
_chemical_formula_weight         755.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   10.9739(12)
_cell_length_b                   17.8839(19)
_cell_length_c                   12.1266(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.951(3)
_cell_angle_gamma                90
_cell_volume                     2319.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.816
_cell_measurement_theta_min      2.857
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.524
_exptl_absorpt_coefficient_mu    6.180
_exptl_absorpt_correction_T_max  0.2568
_exptl_absorpt_correction_T_min  0.1847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1004 before and 0.0859 after correction. The Ratio of minimum to maximum transmission is 0.7192. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            58944
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.096
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_min         2.857
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3139
_reflns_number_total             4112
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.085
_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)+(0.0273P)²+10.3701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0821
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2B
 0.87 with sigma of 0.02
 N2-H2A
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C11(H11), C17(H17), C18(H18), C20(H20)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.18534(4) 0.65141(2) 0.44848(4) 0.02428(13) Uani 1 1 d . . . . .
I2 I 0.54084(4) 0.58166(2) 0.18684(4) 0.02250(12) Uani 1 1 d . . . . .
F1 F 0.3983(3) 0.1938(2) 0.5533(3) 0.0281(9) Uani 1 1 d . . . . .
N1 N -0.0213(5) 0.6620(3) 0.7104(5) 0.0248(13) Uani 1 1 d . . . . .
N2 N 0.3627(6) 0.4824(3) 0.3898(5) 0.0263(13) Uani 1 1 d D . . . .
H2A H 0.324(6) 0.517(3) 0.417(6) 0.03(2) Uiso 1 1 d D . . . .
H2B H 0.421(5) 0.494(4) 0.356(6) 0.04(2) Uiso 1 1 d D . . . .
N3 N 0.7515(5) 0.4609(3) -0.0144(5) 0.0216(12) Uani 1 1 d . . . . .
C1 C -0.0171(6) 0.5928(4) 0.7548(6) 0.0273(16) Uani 1 1 d . . . . .
H1 H -0.0568 0.5835 0.8154 0.033 Uiso 1 1 calc R . . . .
C2 C 0.0436(6) 0.5354(4) 0.7139(6) 0.0264(16) Uani 1 1 d . . . . .
H2 H 0.0459 0.4869 0.7461 0.032 Uiso 1 1 calc R . . . .
C3 C 0.0370(6) 0.6769(4) 0.6259(6) 0.0251(16) Uani 1 1 d . . . . .
H3 H 0.0344 0.7263 0.5963 0.030 Uiso 1 1 calc R . . . .
C4 C 0.0996(6) 0.6226(4) 0.5822(6) 0.0241(15) Uani 1 1 d . . . . .
C5 C 0.1021(6) 0.5493(4) 0.6241(6) 0.0221(15) Uani 1 1 d . . . . .
C6 C 0.1657(6) 0.4899(4) 0.5818(6) 0.0252(16) Uani 1 1 d . . . . .
C7 C 0.2230(6) 0.4405(4) 0.5481(5) 0.0236(15) Uani 1 1 d . . . . .
C8 C 0.2978(6) 0.3874(4) 0.5074(6) 0.0242(15) Uani 1 1 d . . . . .
C9 C 0.3072(6) 0.3136(4) 0.5464(6) 0.0246(15) Uani 1 1 d . . . . .
H9 H 0.2579 0.2972 0.5969 0.030 Uiso 1 1 calc R . . . .
C10 C 0.3875(6) 0.2649(4) 0.5116(6) 0.0239(15) Uani 1 1 d . . . . .
C11 C 0.4589(6) 0.2848(4) 0.4360(6) 0.0242(15) Uani 1 1 d . . . . .
H11 H 0.5129 0.2496 0.4127 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3702(6) 0.4117(4) 0.4299(5) 0.0209(14) Uani 1 1 d . . . . .
C13 C 0.4500(6) 0.3583(4) 0.3945(5) 0.0204(14) Uani 1 1 d . . . . .
C14 C 0.5205(6) 0.3812(4) 0.3146(6) 0.0227(15) Uani 1 1 d . . . . .
C15 C 0.5764(6) 0.4022(4) 0.2467(6) 0.0236(15) Uani 1 1 d . . . . .
C16 C 0.6386(6) 0.4231(4) 0.1600(5) 0.0212(15) Uani 1 1 d . . . . .
C17 C 0.7022(6) 0.3695(4) 0.1099(5) 0.0221(15) Uani 1 1 d . . . . .
H17 H 0.7078 0.3194 0.1365 0.026 Uiso 1 1 calc R . . . .
C18 C 0.7564(6) 0.3891(4) 0.0228(5) 0.0205(14) Uani 1 1 d . . . . .
H18 H 0.7978 0.3523 -0.0118 0.025 Uiso 1 1 calc R . . . .
C19 C 0.6385(6) 0.4966(4) 0.1237(6) 0.0211(15) Uani 1 1 d . . . . .
C20 C 0.6944(6) 0.5147(4) 0.0343(5) 0.0236(15) Uani 1 1 d . . . . .
H20 H 0.6923 0.5648 0.0077 0.028 Uiso 1 1 calc R . . . .
C21 C -0.0946(7) 0.7213(4) 0.7509(6) 0.0302(17) Uani 1 1 d . . . . .
H21A H -0.0613 0.7704 0.7369 0.045 Uiso 1 1 calc GR . . . .
H21B H -0.0887 0.7151 0.8322 0.045 Uiso 1 1 calc GR . . . .
H21C H -0.1823 0.7178 0.7104 0.045 Uiso 1 1 calc GR . . . .
C22 C 0.8009(6) 0.4788(4) -0.1148(6) 0.0265(16) Uani 1 1 d . . . . .
H22A H 0.8925 0.4772 -0.0946 0.040 Uiso 1 1 calc GR . . . .
H22B H 0.7734 0.5289 -0.1420 0.040 Uiso 1 1 calc GR . . . .
H22C H 0.7698 0.4421 -0.1745 0.040 Uiso 1 1 calc GR . . . .
Br1 Br 0.33144(7) 0.69351(4) 0.25307(6) 0.02765(18) Uani 1 1 d . . . . .
Br2 Br 0.93164(7) 0.63812(4) 0.03847(6) 0.03191(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.113(7) . ?
I2 C19 2.101(6) . ?
F1 C10 1.364(7) . ?
N1 C1 1.345(9) . ?
N1 C3 1.352(9) . ?
N1 C21 1.481(8) . ?
N2 H2A 0.86(2) . ?
N2 H2B 0.86(2) . ?
N2 C12 1.351(9) . ?
N3 C18 1.358(8) . ?
N3 C20 1.354(8) . ?
N3 C22 1.475(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(10) . ?
C2 H2 0.9500 . ?
C2 C5 1.404(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(9) . ?
C4 C5 1.404(10) . ?
C5 C6 1.428(10) . ?
C6 C7 1.208(9) . ?
C7 C8 1.415(9) . ?
C8 C9 1.397(10) . ?
C8 C12 1.427(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.371(9) . ?
C10 C11 1.380(9) . ?
C11 H11 0.9500 . ?
C11 C13 1.403(9) . ?
C12 C13 1.426(9) . ?
C13 C14 1.430(9) . ?
C14 C15 1.192(9) . ?
C15 C16 1.426(9) . ?
C16 C17 1.402(9) . ?
C16 C19 1.387(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.398(9) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 N1 C3 120.4(6) . . ?
C1 N1 C21 119.9(6) . . ?
C3 N1 C21 119.6(6) . . ?
H2A N2 H2B 119(7) . . ?
C12 N2 H2A 122(5) . . ?
C12 N2 H2B 114(5) . . ?
C18 N3 C22 119.0(5) . . ?
C20 N3 C18 121.0(6) . . ?
C20 N3 C22 119.9(6) . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.2(6) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C5 119.4(7) . . ?
C5 C2 H2 120.3 . . ?
N1 C3 H3 119.4 . . ?
N1 C3 C4 121.2(7) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 I1 118.3(5) . . ?
C3 C4 C5 119.7(6) . . ?
C5 C4 I1 122.0(5) . . ?
C2 C5 C6 119.5(6) . . ?
C4 C5 C2 118.1(6) . . ?
C4 C5 C6 122.4(6) . . ?
C7 C6 C5 177.9(8) . . ?
C6 C7 C8 175.1(7) . . ?
C7 C8 C12 118.5(6) . . ?
C9 C8 C7 121.4(6) . . ?
C9 C8 C12 120.0(6) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 H9 120.0 . . ?
F1 C10 C9 119.1(6) . . ?
F1 C10 C11 118.1(6) . . ?
C9 C10 C11 122.8(6) . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C13 118.3(6) . . ?
C13 C11 H11 120.8 . . ?
N2 C12 C8 121.7(6) . . ?
N2 C12 C13 120.7(6) . . ?
C13 C12 C8 117.7(6) . . ?
C11 C13 C12 121.2(6) . . ?
C11 C13 C14 120.5(6) . . ?
C12 C13 C14 118.3(6) . . ?
C15 C14 C13 177.8(7) . . ?
C14 C15 C16 175.7(7) . . ?
C17 C16 C15 120.6(6) . . ?
C19 C16 C15 121.0(6) . . ?
C19 C16 C17 118.4(6) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(6) . . ?
C18 C17 H17 119.9 . . ?
N3 C18 C17 120.5(6) . . ?
N3 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C19 I2 122.4(5) . . ?
C16 C19 C20 119.7(6) . . ?
C20 C19 I2 117.6(5) . . ?
N3 C20 C19 120.0(6) . . ?
N3 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_umt_ob24a
_database_code_depnum_ccdc_archive 'CCDC 1825326'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H44 F I2 N3, 2(I)'
_chemical_formula_sum            'C36 H44 F I4 N3'
_chemical_formula_weight         1045.34
_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'
N N 0.0061 0.0033 '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                   17.086(3)
_cell_length_b                   18.092(3)
_cell_length_c                   13.3174(18)
_cell_angle_alpha                90
_cell_angle_beta                 111.458(4)
_cell_angle_gamma                90
_cell_volume                     3831.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9280
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.857
_cell_measurement_theta_min      3.261
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.368
_exptl_absorpt_coefficient_mu    3.286
_exptl_absorpt_correction_T_max  0.0912
_exptl_absorpt_correction_T_min  0.0532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1133 before and 0.0959 after correction. The Ratio of minimum to maximum transmission is 0.5833. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            145488
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.133
_diffrn_reflns_theta_max         25.133
_diffrn_reflns_theta_min         3.060
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5271
_reflns_number_total             6814
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.318
_refine_diff_density_min         -1.542
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.143
_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)+(0.0452P)²+28.7820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT434_umt_ob24a           
;
PROBLEM: Short Inter HL..HL Contact I1       ..I3               3.36 Ang.  
RESPONSE: This alert is the result of a strong halogen bond interaction.
;
_vrf_PLAT910_umt_ob24a           
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: The reflections were observed, however their proximity to the 
beamstop inhibited accurate intensity measurement and these reflections 
have been excluded from the data used for refinement. The reflection 100
is the exception and was not observed, hidden by the beamstop.
;
# end Validation Reply Form
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.87 with sigma of 0.02
 C31-C30 \\sim C31B-C30
 with sigma of 0.02
 C32-C31 \\sim C32B-C31B
 with sigma of 0.02
 C33-C32 \\sim C32B-C33B
 with sigma of 0.02
 C33-C34 \\sim C33B-C34
 with sigma of 0.02
 C35-C36 \\sim C35B-C36B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C29, C30, C31, C32, C33, C34, C35, C36, C31B, C32B, C33B, C35B, C36B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C21, C21B, C22B, C22, C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H23C)=Sof(H23D)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22C)=
 Sof(H22D)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H23A)=Sof(H23B)=
 FVAR(1)
 Sof(H30C)=Sof(H30D)=Sof(H34C)=Sof(H34D)=Sof(C31B)=Sof(H31C)=Sof(H31D)=
 Sof(C32B)=Sof(H32C)=Sof(H32D)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C35B)=
 Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C23(H23C,H23D), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B),
 C30(H30A,H30B), C30(H30C,H30D), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
  C34(H34A,H34B), C34(H34C,H34D), C35(H35A,H35B), C21B(H21C,H21D), C22B(H22C,
 H22D), C31B(H31C,H31D), C32B(H32C,H32D), C33B(H33C,H33D), C35B(H35C,H35D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C11(H11), C17(H17), C18(H18), C20(H20)
5.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C36(H36A,H36B,H36C), C36B(H36D,H36E,H36F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.51615(4) 0.58568(3) 0.67533(5) 0.04539(18) Uani 1 1 d . . . . .
I2 I 0.29221(3) 0.66376(3) 0.89606(4) 0.03427(15) Uani 1 1 d . . . . .
F1 F 0.4437(3) 0.2138(2) 1.0256(4) 0.0488(13) Uani 1 1 d . . . . .
N1 N 0.6785(6) 0.4703(5) 0.5438(8) 0.070(3) Uani 1 1 d . U . . .
N2 N 0.4196(5) 0.4977(4) 0.8676(6) 0.0377(16) Uani 1 1 d D . . . .
H2A H 0.445(5) 0.512(5) 0.825(6) 0.045 Uiso 1 1 d DR . . . .
H2B H 0.387(5) 0.531(4) 0.880(7) 0.045 Uiso 1 1 d DR . . . .
N3 N 0.1581(4) 0.6744(3) 1.1121(5) 0.0353(15) Uani 1 1 d . . . . .
C1 C 0.6792(6) 0.3997(5) 0.5756(7) 0.047(2) Uani 1 1 d . . . . .
H1 H 0.7114 0.3642 0.5547 0.056 Uiso 1 1 calc R . . . .
C2 C 0.6353(5) 0.3783(4) 0.6366(6) 0.0352(18) Uani 1 1 d . . . . .
H2 H 0.6356 0.3278 0.6561 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6345(8) 0.5212(6) 0.5748(10) 0.075(4) Uani 1 1 d . . . . .
H3 H 0.6347 0.5710 0.5523 0.090 Uiso 1 1 calc R . . . .
C4 C 0.5894(6) 0.5035(5) 0.6376(7) 0.044(2) Uani 1 1 d . . . . .
C5 C 0.5891(5) 0.4295(4) 0.6715(6) 0.0328(17) Uani 1 1 d . . . . .
C6 C 0.5443(5) 0.4092(4) 0.7396(6) 0.0315(17) Uani 1 1 d . . . . .
C7 C 0.5113(5) 0.3916(4) 0.8019(6) 0.0318(17) Uani 1 1 d . . . . .
C8 C 0.4711(5) 0.3736(4) 0.8737(6) 0.0336(18) Uani 1 1 d . . . . .
C9 C 0.4774(5) 0.3012(4) 0.9166(6) 0.0344(18) Uani 1 1 d . . . . .
H9 H 0.5086 0.2644 0.8967 0.041 Uiso 1 1 calc R . . . .
C10 C 0.4380(6) 0.2847(4) 0.9871(7) 0.040(2) Uani 1 1 d . . . . .
C11 C 0.3931(5) 0.3357(4) 1.0195(6) 0.0367(19) Uani 1 1 d . . . . .
H11 H 0.3668 0.3223 1.0686 0.044 Uiso 1 1 calc R . . . .
C12 C 0.4257(5) 0.4281(4) 0.9066(6) 0.0317(17) Uani 1 1 d . . . . .
C13 C 0.3861(5) 0.4082(4) 0.9794(6) 0.0312(17) Uani 1 1 d . . . . .
C14 C 0.3382(5) 0.4617(4) 1.0106(6) 0.0360(19) Uani 1 1 d . . . . .
C15 C 0.2979(5) 0.5098(4) 1.0332(6) 0.0343(18) Uani 1 1 d . . . . .
C16 C 0.2504(5) 0.5657(4) 1.0595(6) 0.0320(17) Uani 1 1 d . . . . .
C17 C 0.2111(5) 0.5521(4) 1.1332(6) 0.0374(19) Uani 1 1 d . . . . .
H17 H 0.2163 0.5049 1.1664 0.045 Uiso 1 1 calc R . . . .
C18 C 0.1645(5) 0.6072(4) 1.1580(6) 0.0338(18) Uani 1 1 d . . . . .
H18 H 0.1373 0.5976 1.2074 0.041 Uiso 1 1 calc R . . . .
C19 C 0.2411(5) 0.6370(4) 1.0137(6) 0.0309(17) Uani 1 1 d . . . . .
C20 C 0.1946(5) 0.6889(5) 1.0398(6) 0.0345(18) Uani 1 1 d . . . . .
H20 H 0.1876 0.7362 1.0067 0.041 Uiso 1 1 calc R . . . .
C21 C 0.7051(11) 0.4824(8) 0.4457(14) 0.037(4) Uani 0.548(19) 1 d . U P A 1
H21A H 0.7350 0.4386 0.4330 0.044 Uiso 0.548(19) 1 calc R . P A 1
H21B H 0.6557 0.4930 0.3796 0.044 Uiso 0.548(19) 1 calc R . P A 1
C22 C 0.7632(12) 0.5489(9) 0.4790(15) 0.045(5) Uani 0.548(19) 1 d . U P A 1
H22A H 0.8173 0.5362 0.5371 0.054 Uiso 0.548(19) 1 calc R . P A 1
H22B H 0.7366 0.5906 0.5027 0.054 Uiso 0.548(19) 1 calc R . P A 1
C23 C 0.7760(8) 0.5676(5) 0.3637(10) 0.065(3) Uani 1 1 d . U . . .
H23A H 0.7206 0.5684 0.3037 0.077 Uiso 0.548(19) 1 calc R . P A 1
H23B H 0.8023 0.6168 0.3681 0.077 Uiso 0.548(19) 1 calc R . P A 1
H23C H 0.7497 0.5967 0.2968 0.077 Uiso 0.452(19) 1 calc R . P A 2
H23D H 0.8119 0.6017 0.4199 0.077 Uiso 0.452(19) 1 calc R . P A 2
C24 C 0.8316(7) 0.5088(5) 0.3430(8) 0.052(2) Uani 1 1 d . U . . .
H24A H 0.7988 0.4625 0.3207 0.062 Uiso 1 1 calc R . . . .
H24B H 0.8794 0.4987 0.4110 0.062 Uiso 1 1 calc R . . . .
C25 C 0.8656(6) 0.5310(5) 0.2561(7) 0.044(2) Uani 1 1 d . U . . .
H25A H 0.8177 0.5382 0.1872 0.052 Uiso 1 1 calc R . . . .
H25B H 0.8952 0.5789 0.2764 0.052 Uiso 1 1 calc R . . . .
C26 C 0.9248(6) 0.4754(5) 0.2391(7) 0.045(2) Uani 1 1 d . U . . .
H26A H 0.8958 0.4271 0.2215 0.054 Uiso 1 1 calc R . . . .
H26B H 0.9736 0.4695 0.3075 0.054 Uiso 1 1 calc R . . . .
C27 C 0.9566(6) 0.4956(6) 0.1507(7) 0.049(2) Uani 1 1 d . U . . .
H27A H 0.9080 0.5002 0.0819 0.058 Uiso 1 1 calc R . . . .
H27B H 0.9846 0.5444 0.1673 0.058 Uiso 1 1 calc R . . . .
C28 C 1.0173(8) 0.4403(7) 0.1361(11) 0.077(3) Uani 1 1 d . U . . .
H28A H 1.0651 0.4343 0.2044 0.115 Uiso 1 1 calc GR . . . .
H28B H 1.0376 0.4578 0.0804 0.115 Uiso 1 1 calc GR . . . .
H28C H 0.9889 0.3926 0.1142 0.115 Uiso 1 1 calc GR . . . .
C29 C 0.1051(6) 0.7323(4) 1.1375(7) 0.046(2) Uani 1 1 d . U . . .
H29A H 0.1147 0.7305 1.2154 0.055 Uiso 1 1 calc R . . . .
H29B H 0.1221 0.7818 1.1212 0.055 Uiso 1 1 calc R . . . .
C30 C 0.0133(7) 0.7206(6) 1.0733(11) 0.073(3) Uani 1 1 d D U . . .
H30A H -0.0007 0.6676 1.0736 0.087 Uiso 0.649(13) 1 calc R . P B 1
H30B H 0.0005 0.7360 0.9976 0.087 Uiso 0.649(13) 1 calc R . P B 1
H30C H -0.0100 0.6849 1.1113 0.087 Uiso 0.351(13) 1 calc R . P B 2
H30D H 0.0066 0.6994 1.0021 0.087 Uiso 0.351(13) 1 calc R . P B 2
C31 C -0.0412(10) 0.7677(10) 1.1241(13) 0.064(4) Uani 0.649(13) 1 d D U P B 1
H31A H -0.0233 0.7561 1.2020 0.076 Uiso 0.649(13) 1 calc R . P B 1
H31B H -0.0308 0.8210 1.1172 0.076 Uiso 0.649(13) 1 calc R . P B 1
C32 C -0.1349(11) 0.7523(11) 1.0698(15) 0.074(5) Uani 0.649(13) 1 d D U P B 1
H32A H -0.1525 0.7688 0.9938 0.089 Uiso 0.649(13) 1 calc R . P B 1
H32B H -0.1429 0.6980 1.0687 0.089 Uiso 0.649(13) 1 calc R . P B 1
C33 C -0.1929(12) 0.7860(9) 1.1164(14) 0.070(4) Uani 0.649(13) 1 d D U P B 1
H33A H -0.2510 0.7848 1.0623 0.085 Uiso 0.649(13) 1 calc R . P B 1
H33B H -0.1772 0.8383 1.1346 0.085 Uiso 0.649(13) 1 calc R . P B 1
C34 C -0.1902(8) 0.7453(6) 1.2167(10) 0.073(3) Uani 1 1 d D U . . .
H34A H -0.1338 0.7503 1.2738 0.088 Uiso 0.649(13) 1 calc R . P B 1
H34B H -0.2015 0.6920 1.2005 0.088 Uiso 0.649(13) 1 calc R . P B 1
H34C H -0.2350 0.7073 1.1954 0.088 Uiso 0.351(13) 1 calc R . P B 2
H34D H -0.1527 0.7347 1.2919 0.088 Uiso 0.351(13) 1 calc R . P B 2
C35 C -0.2622(12) 0.7807(8) 1.2584(15) 0.065(4) Uani 0.649(13) 1 d D U P B 1
H35A H -0.3144 0.7912 1.1959 0.078 Uiso 0.649(13) 1 calc R . P B 1
H35B H -0.2756 0.7454 1.3065 0.078 Uiso 0.649(13) 1 calc R . P B 1
C36 C -0.2268(16) 0.8520(12) 1.319(2) 0.078(7) Uani 0.649(13) 1 d D U P B 1
H36A H -0.2249 0.8901 1.2676 0.117 Uiso 0.649(13) 1 calc GR . P B 1
H36B H -0.1699 0.8430 1.3711 0.117 Uiso 0.649(13) 1 calc GR . P B 1
H36C H -0.2629 0.8687 1.3573 0.117 Uiso 0.649(13) 1 calc GR . P B 1
C21B C 0.7527(13) 0.5059(11) 0.5126(17) 0.034(5) Uani 0.452(19) 1 d . U P A 2
H21C H 0.7825 0.5454 0.5637 0.041 Uiso 0.452(19) 1 calc R . P A 2
H21D H 0.7936 0.4681 0.5098 0.041 Uiso 0.452(19) 1 calc R . P A 2
C22B C 0.7030(14) 0.5368(11) 0.4014(17) 0.045(5) Uani 0.452(19) 1 d . U P A 2
H22C H 0.6648 0.5769 0.4051 0.055 Uiso 0.452(19) 1 calc R . P A 2
H22D H 0.6699 0.4977 0.3521 0.055 Uiso 0.452(19) 1 calc R . P A 2
C31B C -0.037(2) 0.7960(15) 1.056(3) 0.083(8) Uani 0.351(13) 1 d D U P B 2
H31C H 0.0010 0.8387 1.0673 0.099 Uiso 0.351(13) 1 calc R . P B 2
H31D H -0.0805 0.7986 0.9826 0.099 Uiso 0.351(13) 1 calc R . P B 2
C32B C -0.078(2) 0.7963(18) 1.139(3) 0.083(9) Uani 0.351(13) 1 d D U P B 2
H32C H -0.0324 0.7966 1.2106 0.100 Uiso 0.351(13) 1 calc R . P B 2
H32D H -0.1079 0.8442 1.1316 0.100 Uiso 0.351(13) 1 calc R . P B 2
C33B C -0.139(2) 0.7381(18) 1.143(3) 0.078(8) Uani 0.351(13) 1 d D U P B 2
H33C H -0.1067 0.6913 1.1622 0.094 Uiso 0.351(13) 1 calc R . P B 2
H33D H -0.1797 0.7319 1.0680 0.094 Uiso 0.351(13) 1 calc R . P B 2
C35B C -0.2270(18) 0.8144(14) 1.214(2) 0.051(6) Uani 0.351(13) 1 d D U P B 2
H35C H -0.2772 0.8191 1.1466 0.062 Uiso 0.351(13) 1 calc R . P B 2
H35D H -0.1867 0.8537 1.2138 0.062 Uiso 0.351(13) 1 calc R . P B 2
C36B C -0.252(3) 0.823(2) 1.311(3) 0.077(12) Uani 0.351(13) 1 d D U P B 2
H36D H -0.2891 0.8667 1.3009 0.115 Uiso 0.351(13) 1 calc GR . P B 2
H36E H -0.2020 0.8303 1.3761 0.115 Uiso 0.351(13) 1 calc GR . P B 2
H36F H -0.2826 0.7791 1.3194 0.115 Uiso 0.351(13) 1 calc GR . P B 2
I3 I 0.36765(4) 0.69908(3) 0.69852(5) 0.04092(16) Uani 1 1 d . . . . .
I4 I 0.09027(5) 0.63880(3) 0.39221(5) 0.0543(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.119(8) . ?
I2 C19 2.110(7) . ?
F1 C10 1.371(9) . ?
N1 C1 1.344(11) . ?
N1 C3 1.345(12) . ?
N1 C21 1.549(15) . ?
N1 C21B 1.61(2) . ?
N2 H2A 0.87(2) . ?
N2 H2B 0.87(2) . ?
N2 C12 1.353(10) . ?
N3 C18 1.347(10) . ?
N3 C20 1.351(10) . ?
N3 C29 1.502(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.350(11) . ?
C2 H2 0.9500 . ?
C2 C5 1.402(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(12) . ?
C4 C5 1.413(11) . ?
C5 C6 1.432(11) . ?
C6 C7 1.204(11) . ?
C7 C8 1.405(11) . ?
C8 C9 1.416(11) . ?
C8 C12 1.419(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(11) . ?
C10 C11 1.369(11) . ?
C11 H11 0.9500 . ?
C11 C13 1.404(11) . ?
C12 C13 1.417(10) . ?
C13 C14 1.424(11) . ?
C14 C15 1.214(11) . ?
C15 C16 1.418(11) . ?
C16 C17 1.399(11) . ?
C16 C19 1.411(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.355(11) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.52(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.662(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
C23 C24 1.518(13) . ?
C23 C22B 1.60(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.527(11) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.501(13) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.511(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.504(14) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.500(15) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 H30C 0.9900 . ?
C30 H30D 0.9900 . ?
C30 C31 1.586(17) . ?
C30 C31B 1.59(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.52(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.48(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.511(18) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 H34C 0.9900 . ?
C34 H34D 0.9900 . ?
C34 C35 1.65(2) . ?
C34 C33B 1.55(2) . ?
C34 C35B 1.39(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.524(19) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C21B C22B 1.52(3) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C31B H31C 0.9900 . ?
C31B H31D 0.9900 . ?
C31B C32B 1.50(3) . ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?
C32B C33B 1.49(3) . ?
C33B H33C 0.9900 . ?
C33B H33D 0.9900 . ?
C35B H35C 0.9900 . ?
C35B H35D 0.9900 . ?
C35B C36B 1.52(2) . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 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
C1 N1 C3 119.8(8) . . ?
C1 N1 C21 115.3(9) . . ?
C1 N1 C21B 123.0(9) . . ?
C3 N1 C21 122.1(9) . . ?
C3 N1 C21B 112.8(10) . . ?
H2A N2 H2B 115(8) . . ?
C12 N2 H2A 123(6) . . ?
C12 N2 H2B 122(6) . . ?
C18 N3 C20 121.1(7) . . ?
C18 N3 C29 118.9(6) . . ?
C20 N3 C29 119.9(7) . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.2(8) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C5 121.0(7) . . ?
C5 C2 H2 119.5 . . ?
N1 C3 H3 119.0 . . ?
N1 C3 C4 122.0(9) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 I1 119.7(6) . . ?
C3 C4 C5 119.1(8) . . ?
C5 C4 I1 121.1(6) . . ?
C2 C5 C4 116.8(7) . . ?
C2 C5 C6 122.4(7) . . ?
C4 C5 C6 120.8(7) . . ?
C7 C6 C5 176.0(8) . . ?
C6 C7 C8 177.9(8) . . ?
C7 C8 C9 120.4(7) . . ?
C7 C8 C12 120.4(7) . . ?
C9 C8 C12 119.2(7) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(7) . . ?
C10 C9 H9 120.2 . . ?
F1 C10 C9 118.3(7) . . ?
C11 C10 F1 119.0(7) . . ?
C11 C10 C9 122.7(8) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C13 119.3(7) . . ?
C13 C11 H11 120.4 . . ?
N2 C12 C8 120.2(7) . . ?
N2 C12 C13 120.7(7) . . ?
C13 C12 C8 119.1(7) . . ?
C11 C13 C12 120.2(7) . . ?
C11 C13 C14 120.1(7) . . ?
C12 C13 C14 119.8(7) . . ?
C15 C14 C13 176.6(8) . . ?
C14 C15 C16 179.6(8) . . ?
C17 C16 C15 120.8(7) . . ?
C17 C16 C19 117.2(7) . . ?
C19 C16 C15 121.9(7) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(7) . . ?
C18 C17 H17 119.9 . . ?
N3 C18 C17 119.9(7) . . ?
N3 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C16 C19 I2 121.3(5) . . ?
C20 C19 I2 118.1(6) . . ?
C20 C19 C16 120.5(7) . . ?
N3 C20 C19 121.0(7) . . ?
N3 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
N1 C21 H21A 111.1 . . ?
N1 C21 H21B 111.1 . . ?
H21A C21 H21B 109.1 . . ?
C22 C21 N1 103.2(13) . . ?
C22 C21 H21A 111.1 . . ?
C22 C21 H21B 111.1 . . ?
C21 C22 H22A 111.6 . . ?
C21 C22 H22B 111.6 . . ?
C21 C22 C23 100.6(13) . . ?
H22A C22 H22B 109.4 . . ?
C23 C22 H22A 111.6 . . ?
C23 C22 H22B 111.6 . . ?
C22 C23 H23A 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
H23C C23 H23D 107.5 . . ?
C24 C23 C22 109.1(10) . . ?
C24 C23 H23A 109.9 . . ?
C24 C23 H23B 109.9 . . ?
C24 C23 H23C 108.5 . . ?
C24 C23 H23D 108.5 . . ?
C24 C23 C22B 115.0(10) . . ?
C22B C23 H23C 108.5 . . ?
C22B C23 H23D 108.5 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C23 C24 C25 113.0(8) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C24 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 C24 113.7(8) . . ?
C26 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C25 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C25 C26 C27 114.2(8) . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 C26 113.7(9) . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 H29A 109.4 . . ?
N3 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 N3 111.3(7) . . ?
C30 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
C29 C30 H30A 109.7 . . ?
C29 C30 H30B 109.7 . . ?
C29 C30 H30C 109.4 . . ?
C29 C30 H30D 109.4 . . ?
C29 C30 C31 109.6(10) . . ?
C29 C30 C31B 111.3(18) . . ?
H30A C30 H30B 108.2 . . ?
H30C C30 H30D 108.0 . . ?
C31 C30 H30A 109.7 . . ?
C31 C30 H30B 109.7 . . ?
C31B C30 H30C 109.4 . . ?
C31B C30 H30D 109.4 . . ?
C30 C31 H31A 109.2 . . ?
C30 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 C30 112.2(12) . . ?
C32 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C31 C32 H32A 107.7 . . ?
C31 C32 H32B 107.7 . . ?
H32A C32 H32B 107.1 . . ?
C33 C32 C31 118.3(15) . . ?
C33 C32 H32A 107.7 . . ?
C33 C32 H32B 107.7 . . ?
C32 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C32 C33 C34 111.2(13) . . ?
H33A C33 H33B 108.0 . . ?
C34 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
C33 C34 H34A 109.9 . . ?
C33 C34 H34B 109.9 . . ?
C33 C34 C35 108.8(11) . . ?
H34A C34 H34B 108.3 . . ?
H34C C34 H34D 107.6 . . ?
C35 C34 H34A 109.9 . . ?
C35 C34 H34B 109.9 . . ?
C33B C34 H34C 108.7 . . ?
C33B C34 H34D 108.7 . . ?
C35B C34 H34C 108.7 . . ?
C35B C34 H34D 108.7 . . ?
C35B C34 C33B 114.3(18) . . ?
C34 C35 H35A 110.1 . . ?
C34 C35 H35B 110.1 . . ?
H35A C35 H35B 108.4 . . ?
C36 C35 C34 107.9(14) . . ?
C36 C35 H35A 110.1 . . ?
C36 C35 H35B 110.1 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N1 C21B H21C 111.6 . . ?
N1 C21B H21D 111.6 . . ?
H21C C21B H21D 109.4 . . ?
C22B C21B N1 100.9(16) . . ?
C22B C21B H21C 111.6 . . ?
C22B C21B H21D 111.6 . . ?
C23 C22B H22C 111.3 . . ?
C23 C22B H22D 111.3 . . ?
C21B C22B C23 102.3(16) . . ?
C21B C22B H22C 111.3 . . ?
C21B C22B H22D 111.3 . . ?
H22C C22B H22D 109.2 . . ?
C30 C31B H31C 110.5 . . ?
C30 C31B H31D 110.5 . . ?
H31C C31B H31D 108.7 . . ?
C32B C31B C30 106(2) . . ?
C32B C31B H31C 110.5 . . ?
C32B C31B H31D 110.5 . . ?
C31B C32B H32C 106.7 . . ?
C31B C32B H32D 106.7 . . ?
H32C C32B H32D 106.6 . . ?
C33B C32B C31B 122(3) . . ?
C33B C32B H32C 106.7 . . ?
C33B C32B H32D 106.7 . . ?
C34 C33B H33C 106.9 . . ?
C34 C33B H33D 106.9 . . ?
C32B C33B C34 122(2) . . ?
C32B C33B H33C 106.9 . . ?
C32B C33B H33D 106.9 . . ?
H33C C33B H33D 106.7 . . ?
C34 C35B H35C 109.7 . . ?
C34 C35B H35D 109.7 . . ?
C34 C35B C36B 110(2) . . ?
H35C C35B H35D 108.2 . . ?
C36B C35B H35C 109.7 . . ?
C36B C35B H35D 109.7 . . ?
C35B C36B H36D 109.5 . . ?
C35B C36B H36E 109.5 . . ?
C35B C36B H36F 109.5 . . ?
H36D C36B H36E 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_iotfcl
_database_code_depnum_ccdc_archive 'CCDC 1825327'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-05-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 I2 N2, 2(Cl)'
_chemical_formula_sum            'C22 H16 Cl2 I2 N2'
_chemical_formula_weight         633.07
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   9.1408(3)
_cell_length_b                   18.1854(6)
_cell_length_c                   13.7305(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.8200(10)
_cell_angle_gamma                90
_cell_volume                     2241.83(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9427
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.532
_cell_measurement_theta_min      3.021
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.054
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0594 before and 0.0327 after correction. The Ratio of minimum to maximum transmission is 0.8250. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37851
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_min         3.021
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4270
_reflns_number_total             5125
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.281
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5125
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.063
_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)+(0.0261P)²+5.1722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C4, C3, C2, C1, N1, C5
 with sigma of 0.1
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17),
 C18(H18), C20(H20)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.82892(2) 0.35073(2) 0.58016(2) 0.02011(7) Uani 1 1 d . . . . .
I2 I 0.44471(2) 0.42352(2) 0.82761(2) 0.02023(7) Uani 1 1 d . . . . .
N1 N 1.0460(3) 0.30606(15) 0.3354(2) 0.0201(6) Uani 1 1 d . . . . .
N2 N 0.2118(3) 0.55700(15) 1.0088(2) 0.0198(6) Uani 1 1 d . . . . .
C1 C 0.9874(4) 0.30290(18) 0.4183(2) 0.0208(7) Uani 1 1 d . . . . .
H1 H 0.9946 0.2585 0.4553 0.025 Uiso 1 1 calc R . . . .
C2 C 0.9175(4) 0.36239(18) 0.4502(2) 0.0189(7) Uani 1 1 d . . . . .
C3 C 0.9052(4) 0.42776(18) 0.3949(2) 0.0192(7) Uani 1 1 d . . . . .
C4 C 0.9705(4) 0.42982(19) 0.3100(2) 0.0230(7) Uani 1 1 d . . . . .
H4 H 0.9670 0.4738 0.2723 0.028 Uiso 1 1 calc R . . . .
C5 C 1.0393(4) 0.36865(19) 0.2816(2) 0.0231(7) Uani 1 1 d . . . . .
H5 H 1.0825 0.3702 0.2239 0.028 Uiso 1 1 calc R . . . .
C6 C 0.8281(4) 0.48999(18) 0.4230(2) 0.0210(7) Uani 1 1 d . . . . .
C7 C 0.7601(4) 0.53961(18) 0.4499(2) 0.0209(7) Uani 1 1 d . . . . .
C8 C 0.6797(4) 0.59618(18) 0.4903(2) 0.0198(7) Uani 1 1 d . . . . .
C9 C 0.6660(4) 0.66731(19) 0.4510(3) 0.0225(7) Uani 1 1 d . . . . .
H9 H 0.7082 0.6790 0.3947 0.027 Uiso 1 1 calc R . . . .
C10 C 0.5904(4) 0.72085(19) 0.4943(3) 0.0238(7) Uani 1 1 d . . . . .
H10 H 0.5803 0.7689 0.4668 0.029 Uiso 1 1 calc R . . . .
C11 C 0.5301(4) 0.70513(18) 0.5765(3) 0.0221(7) Uani 1 1 d . . . . .
H11 H 0.4790 0.7422 0.6057 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6180(4) 0.57933(18) 0.5736(3) 0.0205(7) Uani 1 1 d . . . . .
H12 H 0.6262 0.5310 0.6003 0.025 Uiso 1 1 calc R . . . .
C13 C 0.5444(4) 0.63377(18) 0.6171(3) 0.0202(7) Uani 1 1 d . . . . .
C14 C 0.4820(4) 0.61636(17) 0.7026(3) 0.0204(7) Uani 1 1 d . . . . .
C15 C 0.4297(4) 0.60066(18) 0.7732(3) 0.0206(7) Uani 1 1 d . . . . .
C16 C 0.3581(4) 0.58459(17) 0.8542(2) 0.0187(7) Uani 1 1 d . . . . .
C17 C 0.2956(4) 0.64204(18) 0.9017(3) 0.0211(7) Uani 1 1 d . . . . .
H17 H 0.3026 0.6913 0.8802 0.025 Uiso 1 1 calc R . . . .
C18 C 0.2250(4) 0.62712(19) 0.9786(3) 0.0227(7) Uani 1 1 d . . . . .
H18 H 0.1847 0.6662 1.0112 0.027 Uiso 1 1 calc R . . . .
C19 C 0.3454(4) 0.51255(17) 0.8887(2) 0.0187(7) Uani 1 1 d . . . . .
C20 C 0.2714(4) 0.50014(17) 0.9660(2) 0.0188(7) Uani 1 1 d . . . . .
H20 H 0.2623 0.4515 0.9892 0.023 Uiso 1 1 calc R . . . .
C21 C 1.1132(4) 0.23857(19) 0.3012(3) 0.0274(8) Uani 1 1 d . . . . .
H21A H 1.1711 0.2129 0.3584 0.041 Uiso 1 1 calc GR . . . .
H21B H 1.1788 0.2522 0.2553 0.041 Uiso 1 1 calc GR . . . .
H21C H 1.0340 0.2062 0.2673 0.041 Uiso 1 1 calc GR . . . .
C22 C 0.1350(4) 0.5433(2) 1.0929(3) 0.0251(8) Uani 1 1 d . . . . .
H22A H 0.1932 0.5647 1.1535 0.038 Uiso 1 1 calc GR . . . .
H22B H 0.1250 0.4902 1.1019 0.038 Uiso 1 1 calc GR . . . .
H22C H 0.0359 0.5659 1.0790 0.038 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.69846(9) 0.30674(4) 0.76894(6) 0.02058(17) Uani 1 1 d . . . . .
Cl2 Cl 0.85632(10) 0.65556(4) 0.94108(6) 0.02168(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.104(3) . ?
I2 C19 2.106(3) . ?
N1 C1 1.348(4) . ?
N1 C5 1.352(4) . ?
N1 C21 1.487(4) . ?
N2 C18 1.353(4) . ?
N2 C20 1.354(4) . ?
N2 C22 1.481(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.369(5) . ?
C2 C3 1.404(5) . ?
C3 C4 1.406(5) . ?
C3 C6 1.424(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.193(5) . ?
C7 C8 1.435(5) . ?
C8 C9 1.398(5) . ?
C8 C12 1.401(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(5) . ?
C11 H11 0.9500 . ?
C11 C13 1.409(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(5) . ?
C13 C14 1.433(5) . ?
C14 C15 1.194(5) . ?
C15 C16 1.422(5) . ?
C16 C17 1.409(5) . ?
C16 C19 1.405(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.364(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 N1 C5 120.8(3) . . ?
C1 N1 C21 119.0(3) . . ?
C5 N1 C21 120.1(3) . . ?
C18 N2 C20 121.4(3) . . ?
C18 N2 C22 118.7(3) . . ?
C20 N2 C22 119.9(3) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.3(3) . . ?
C2 C1 H1 119.3 . . ?
C1 C2 I1 118.0(2) . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 I1 122.6(2) . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 C6 121.3(3) . . ?
C4 C3 C6 120.8(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.3(3) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C3 176.4(4) . . ?
C6 C7 C8 175.0(4) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 C12 119.8(3) . . ?
C12 C8 C7 118.2(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C13 119.6(3) . . ?
C13 C11 H11 120.2 . . ?
C8 C12 H12 120.1 . . ?
C13 C12 C8 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C13 C14 120.4(3) . . ?
C12 C13 C11 120.1(3) . . ?
C12 C13 C14 119.5(3) . . ?
C15 C14 C13 178.9(4) . . ?
C14 C15 C16 176.0(4) . . ?
C17 C16 C15 119.7(3) . . ?
C19 C16 C15 122.3(3) . . ?
C19 C16 C17 118.0(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
N2 C18 C17 120.5(3) . . ?
N2 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C19 I2 120.9(2) . . ?
C20 C19 I2 119.4(2) . . ?
C20 C19 C16 119.7(3) . . ?
N2 C20 C19 120.3(3) . . ?
N2 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
