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

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

data_SRI1
# Added during the CSD deposition process: Sunday 06 May 2018 03:24 PM
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 1525753'
_audit_update_record             
;
2018-05-06 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_SRI1                
;
PROBLEM: Check Calcd Resid. Dens.  0.67A   From C27             6.08 eA-3
RESPONSE: This carbon atom (C27) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;
_vrf_PLAT097_SRI1                
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       6.25 eA-3
RESPONSE: This alert appeared due to missing hydrogen atom on the O1 atom.
;
_vrf_PLAT201_SRI1                
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          1 Report
RESPONSE: C27 is isotropic and can't be solved as anisotropic after multiple trials.
;
_vrf_PLAT306_SRI1                
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O1 Check
RESPONSE: O1 represents an isolated water molecule and thus hydrogen atoms are not assigned.
;
_vrf_PLAT971_SRI1_2              
;
PROBLEM: Check Calcd Resid. Dens.  0.43A   From C27             2.49 eA-3
RESPONSE: This carbon atom (C27) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;
_vrf_PLAT971_SRI1_3              
;
PROBLEM: Check Calcd Resid. Dens.  0.65A   From Br1             1.83 eA-3
RESPONSE: This carbon atom (C27) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;
_vrf_PLAT971_SRI1_4              
;
PROBLEM: Check Calcd Resid. Dens.  0.59A   From Br1             1.77 eA-3
RESPONSE: This carbon atom (C27) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;
_vrf_PLAT971_SRI1_5              
;
PROBLEM: Check Calcd Resid. Dens.  0.42A   From Br1             1.69 eA-3
RESPONSE: This carbon atom (C27) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H38 Br4 I4 N8 O2'
_chemical_formula_weight         1369.91

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'
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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9875(18)
_cell_length_b                   9.862(2)
_cell_length_c                   14.041(3)
_cell_angle_alpha                88.713(5)
_cell_angle_beta                 75.026(4)
_cell_angle_gamma                73.585(5)
_cell_volume                     1023.4(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5128
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      30.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.220
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    6.987
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4572
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9391
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.503
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3601
_reflns_number_gt                3214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+16.6690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3601
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.20409(7) 0.85001(6) 0.73306(4) 0.01819(16) Uani 1 1 d . . . . .
I2 I 0.28310(7) 0.59154(6) 0.22904(4) 0.01955(17) Uani 1 1 d . . . . .
Br1 Br 0.28476(10) 0.31261(8) 0.13183(6) 0.0163(2) Uani 1 1 d . . . . .
Br2 Br 0.21429(12) 0.14099(9) 0.64421(6) 0.0217(2) Uani 1 1 d . . . . .
C3 C 0.1953(11) 0.6559(9) 0.7910(6) 0.0166(17) Uani 1 1 d . . . . .
N1 N 0.2128(9) 0.6162(8) 0.8813(5) 0.0162(14) Uani 1 1 d . . . . .
N2 N 0.1749(9) 0.5459(7) 0.7456(5) 0.0151(14) Uani 1 1 d . . . . .
C1 C 0.1780(11) 0.4366(9) 0.8080(6) 0.0177(17) Uani 1 1 d . . . . .
H1 H 0.166455 0.348530 0.794039 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2006(11) 0.4788(9) 0.8925(6) 0.0186(18) Uani 1 1 d . . . . .
H2 H 0.206949 0.426323 0.947954 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2284(12) 0.7054(10) 0.9581(6) 0.0231(19) Uani 1 1 d . . . . .
H4A H 0.303595 0.764944 0.928034 0.028 Uiso 1 1 calc R U . . .
H4B H 0.287340 0.645847 1.002860 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0467(12) 0.7975(10) 1.0158(7) 0.0241(19) Uani 1 1 d . . . . .
H5A H -0.003599 0.866889 0.974044 0.036 Uiso 1 1 calc R U . . .
H5B H 0.060704 0.844379 1.071186 0.036 Uiso 1 1 calc R U . . .
H5C H -0.032988 0.739929 1.038951 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1522(11) 0.5423(9) 0.6447(6) 0.0147(16) Uani 1 1 d . . . . .
H6A H 0.065519 0.629452 0.635379 0.018 Uiso 1 1 calc R U . . .
H6B H 0.105053 0.464247 0.636219 0.018 Uiso 1 1 calc R U . . .
C7 C 0.3314(10) 0.5249(8) 0.5678(6) 0.0127(16) Uani 1 1 d . . . . .
C11 C 0.3511(11) 0.6070(9) 0.4868(6) 0.0142(16) Uani 1 1 d . . . . .
C8 C 0.4815(11) 0.4182(9) 0.5787(6) 0.0144(16) Uani 1 1 d . . . . .
H8 H 0.467638 0.361826 0.632527 0.017 Uiso 1 1 calc R U . . .
C13 C 0.1855(11) 0.7193(9) 0.4710(6) 0.0188(18) Uani 1 1 d . . . . .
H13A H 0.104124 0.672435 0.454579 0.023 Uiso 1 1 calc R U . . .
H13B H 0.122010 0.775460 0.532291 0.023 Uiso 1 1 calc R U . . .
N5 N 0.2317(9) 0.8149(7) 0.3917(5) 0.0180(15) Uani 1 1 d . . . . .
C19 C 0.2815(13) 1.0028(10) 0.3187(7) 0.027(2) Uani 1 1 d . . . . .
H19 H 0.289689 1.093192 0.303054 0.032 Uiso 1 1 calc R U . . .
N7 N 0.3071(10) 0.8965(8) 0.2492(5) 0.0202(16) Uani 1 1 d . . . . .
C16 C 0.2741(11) 0.7843(9) 0.2951(6) 0.0185(18) Uani 1 1 d . . . . .
C21 C 0.5597(12) 0.9238(11) 0.1155(7) 0.027(2) Uani 1 1 d . . . . .
H21A H 0.557893 1.013709 0.141272 0.041 Uiso 1 1 calc R U . . .
H21B H 0.605157 0.917807 0.044962 0.041 Uiso 1 1 calc R U . . .
H21C H 0.636449 0.849187 0.143046 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3701(13) 0.9092(11) 0.1427(7) 0.026(2) Uani 1 1 d . . . . .
H20A H 0.289134 0.991356 0.122727 0.031 Uiso 1 1 calc R U . . .
H20B H 0.368312 0.826061 0.107818 0.031 Uiso 1 1 calc R U . . .
O1 O 0.7755(11) 0.6923(9) 0.5710(6) 0.0447(19) Uani 1 1 d . . . . .
C27 C 0.2411(13) 0.9581(10) 0.4168(7) 0.026(2) Uiso 1 1 d . . . . .
H27 H 0.225659 1.003502 0.477176 0.032 Uiso 1 1 calc R U . . .


_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 C3 2.075(8) . ?
I2 C16 2.109(8) . ?
C3 N2 1.340(11) . ?
C3 N1 1.349(11) . ?
N1 C2 1.388(11) . ?
N1 C4 1.458(11) . ?
N2 C1 1.373(11) . ?
N2 C6 1.475(10) . ?
C1 C2 1.337(12) . ?
C4 C5 1.506(12) . ?
C6 C7 1.522(11) . ?
C7 C11 1.383(11) . ?
C7 C8 1.394(11) . ?
C11 C8 1.372(11) 2_666 ?
C11 C13 1.529(11) . ?
C13 N5 1.484(10) . ?
N5 C16 1.331(11) . ?
N5 C27 1.490(12) . ?
C19 N7 1.384(12) . ?
C19 C27 1.421(13) . ?
N7 C16 1.324(11) . ?
N7 C20 1.463(11) . ?
C21 C20 1.511(13) . ?

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
N2 C3 N1 107.2(7) . . ?
N2 C3 I1 126.7(6) . . ?
N1 C3 I1 126.1(6) . . ?
C3 N1 C2 108.9(7) . . ?
C3 N1 C4 126.0(7) . . ?
C2 N1 C4 124.9(7) . . ?
C3 N2 C1 109.0(7) . . ?
C3 N2 C6 125.7(7) . . ?
C1 N2 C6 125.3(7) . . ?
C2 C1 N2 108.2(8) . . ?
C1 C2 N1 106.7(7) . . ?
N1 C4 C5 112.0(7) . . ?
N2 C6 C7 111.0(6) . . ?
C11 C7 C8 118.7(7) . . ?
C11 C7 C6 123.3(7) . . ?
C8 C7 C6 117.9(7) . . ?
C8 C11 C7 118.7(7) 2_666 . ?
C8 C11 C13 122.0(7) 2_666 . ?
C7 C11 C13 119.3(7) . . ?
C11 C8 C7 122.6(8) 2_666 . ?
N5 C13 C11 113.1(7) . . ?
C16 N5 C13 126.1(7) . . ?
C16 N5 C27 113.5(7) . . ?
C13 N5 C27 120.4(7) . . ?
N7 C19 C27 112.4(8) . . ?
C16 N7 C19 109.1(7) . . ?
C16 N7 C20 127.4(8) . . ?
C19 N7 C20 123.4(7) . . ?
N7 C16 N5 107.7(7) . . ?
N7 C16 I2 126.9(6) . . ?
N5 C16 I2 125.4(6) . . ?
N7 C20 C21 110.8(7) . . ?
C19 C27 N5 97.1(8) . . ?

_refine_diff_density_max         6.249
_refine_diff_density_min         -1.566
_refine_diff_density_rms         0.219

####################################################################### 
# 
# 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_SRI1_CCDC1
# Added during the CSD deposition process: Sunday 06 May 2018 03:24 PM
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 1526216'
_audit_update_record             
;
2018-05-06 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_SRI1                
;
PROBLEM: Check Calcd Resid. Dens.  0.73A   From C17             5.49 eA-3
RESPONSE: This carbon atom (C17) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;
_vrf_PLAT097_SRI1                
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       5.44 eA-3
RESPONSE: This alert appeared due to missing hydrogen atom on the O1 atom.
;
_vrf_PLAT201_SRI1                
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          1 Report
RESPONSE: C17 is isotropic and can't be solved as anisotropic after multiple attempts.
;
_vrf_PLAT306_SRI1                
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O1 Check
RESPONSE: O1 represents isolated water molecule and thus hydrogen atoms are not assigned.
;
_vrf_PLAT971_SRI1_2              
;
PROBLEM: Check Calcd Resid. Dens.  0.41A   From C17             1.67 eA-3
RESPONSE: This carbon atom (C17) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;
_vrf_PLAT971_SRI1_3              
;
PROBLEM: Check Calcd Resid. Dens.  0.60A   From Br3             1.52 eA-3
RESPONSE: This carbon atom (C17) is isotropic and thus residual density is present. We diffracted crystals from multiple batches but still it was not resolved. 
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H38 Br4 I4 N8 O2'
_chemical_formula_weight         1369.91

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'
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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9866(9)
_cell_length_b                   9.8465(12)
_cell_length_c                   14.0544(16)
_cell_angle_alpha                88.752(3)
_cell_angle_beta                 75.052(2)
_cell_angle_gamma                73.554(3)
_cell_volume                     1022.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7584
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      32.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.221
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    6.993
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5295
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12093
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.502
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3595
_reflns_number_gt                3338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+8.4988P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3595
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.28276(6) 0.59160(5) 0.22915(3) 0.02004(15) Uani 1 1 d . . . . .
I2 I 0.20469(6) 0.85027(4) 0.73280(3) 0.01949(15) Uani 1 1 d . . . . .
Br3 Br 0.28420(8) 0.31296(7) 0.13189(5) 0.01942(18) Uani 1 1 d . . . . .
Br1 Br 0.21475(10) 0.14094(7) 0.64380(5) 0.02396(19) Uani 1 1 d . . . . .
N2 N 0.1756(7) 0.5462(6) 0.7453(4) 0.0149(11) Uani 1 1 d . . . . .
C2 C 0.1960(8) 0.6557(7) 0.7913(5) 0.0162(13) Uani 1 1 d . . . . .
C6 C 0.1534(8) 0.5423(7) 0.6449(4) 0.0148(13) Uani 1 1 d . . . . .
H6A H 0.066587 0.629539 0.635533 0.018 Uiso 1 1 calc R U . . .
H6B H 0.106351 0.464069 0.636421 0.018 Uiso 1 1 calc R U . . .
C1 C 0.1788(9) 0.4350(7) 0.8073(5) 0.0182(14) Uani 1 1 d . . . . .
H1 H 0.167557 0.346722 0.793065 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2012(9) 0.4787(7) 0.8922(5) 0.0199(14) Uani 1 1 d . . . . .
H3 H 0.207622 0.426396 0.947653 0.024 Uiso 1 1 calc R U . . .
C5 C 0.0459(10) 0.7969(8) 1.0155(6) 0.0261(16) Uani 1 1 d . . . . .
H5A H -0.001380 0.869955 0.975082 0.039 Uiso 1 1 calc R U . . .
H5B H 0.058140 0.839504 1.073215 0.039 Uiso 1 1 calc R U . . .
H5C H -0.035255 0.739687 1.034908 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2292(9) 0.7050(8) 0.9577(5) 0.0239(15) Uani 1 1 d . . . . .
H4A H 0.303995 0.764962 0.927813 0.029 Uiso 1 1 calc R U . . .
H4B H 0.288399 0.645173 1.002234 0.029 Uiso 1 1 calc R U . . .
N1 N 0.2128(7) 0.6166(6) 0.8812(4) 0.0169(11) Uani 1 1 d . . . . .
C7 C 0.3324(8) 0.5249(7) 0.5681(5) 0.0135(12) Uani 1 1 d . . . . .
C8 C 0.3502(9) 0.6077(7) 0.4868(5) 0.0152(13) Uani 1 1 d . . . . .
C9 C 0.1844(9) 0.7199(7) 0.4705(5) 0.0194(14) Uani 1 1 d . . . . .
H9A H 0.103994 0.672804 0.453164 0.023 Uiso 1 1 calc R U . . .
H9B H 0.119647 0.776064 0.531611 0.023 Uiso 1 1 calc R U . . .
N3 N 0.2317(7) 0.8152(6) 0.3922(4) 0.0180(12) Uani 1 1 d . . . . .
N4 N 0.3057(8) 0.8967(6) 0.2491(4) 0.0188(12) Uani 1 1 d . . . . .
C11 C 0.2739(9) 0.7834(7) 0.2954(5) 0.0189(14) Uani 1 1 d . . . . .
C12 C 0.3700(10) 0.9087(8) 0.1421(5) 0.0261(16) Uani 1 1 d . . . . .
H12A H 0.289133 0.990557 0.121637 0.031 Uiso 1 1 calc R U . . .
H12B H 0.369089 0.824946 0.107350 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2815(10) 1.0026(8) 0.3183(5) 0.0259(16) Uani 1 1 d . . . . .
H13 H 0.291297 1.092972 0.303275 0.031 Uiso 1 1 calc R U . . .
C14 C 0.5586(10) 0.9237(9) 0.1157(5) 0.0284(17) Uani 1 1 d . . . . .
H14A H 0.555785 1.014545 0.140590 0.043 Uiso 1 1 calc R U . . .
H14B H 0.605563 0.915964 0.045291 0.043 Uiso 1 1 calc R U . . .
H14C H 0.634722 0.850107 0.144403 0.043 Uiso 1 1 calc R U . . .
O1 O 0.7755(9) 0.6926(7) 0.5706(5) 0.0449(15) Uani 1 1 d . . . . .
C15 C 0.4816(8) 0.4182(7) 0.5786(4) 0.0145(13) Uani 1 1 d . . . . .
H15 H 0.467402 0.361706 0.632299 0.017 Uiso 1 1 calc R U . . .
C17 C 0.2405(10) 0.9560(8) 0.4138(6) 0.0270(16) Uiso 1 1 d . . . . .
H17 H 0.223558 1.002128 0.474069 0.032 Uiso 1 1 calc R U . . .


_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 C11 2.099(7) . ?
I2 C2 2.080(6) . ?
N2 C2 1.339(9) . ?
N2 C1 1.383(8) . ?
N2 C6 1.468(8) . ?
C2 N1 1.342(9) . ?
C6 C7 1.520(8) . ?
C1 C3 1.348(10) . ?
C3 N1 1.389(9) . ?
C5 C4 1.514(10) . ?
C4 N1 1.452(9) . ?
C7 C15 1.386(9) . ?
C7 C8 1.390(9) . ?
C8 C15 1.377(9) 2_666 ?
C8 C9 1.531(9) . ?
C9 N3 1.474(8) . ?
N3 C11 1.335(9) . ?
N3 C17 1.451(10) . ?
N4 C11 1.332(9) . ?
N4 C13 1.380(9) . ?
N4 C12 1.472(9) . ?
C12 C14 1.504(10) . ?
C13 C17 1.397(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C1 109.2(5) . . ?
C2 N2 C6 126.2(5) . . ?
C1 N2 C6 124.6(6) . . ?
N2 C2 N1 107.7(6) . . ?
N2 C2 I2 126.1(5) . . ?
N1 C2 I2 126.2(5) . . ?
N2 C6 C7 111.1(5) . . ?
C3 C1 N2 107.1(6) . . ?
C1 C3 N1 107.2(6) . . ?
N1 C4 C5 111.4(6) . . ?
C2 N1 C3 108.7(6) . . ?
C2 N1 C4 126.4(6) . . ?
C3 N1 C4 124.8(6) . . ?
C15 C7 C8 119.2(6) . . ?
C15 C7 C6 117.9(6) . . ?
C8 C7 C6 122.8(6) . . ?
C15 C8 C7 117.8(6) 2_666 . ?
C15 C8 C9 122.1(6) 2_666 . ?
C7 C8 C9 120.0(6) . . ?
N3 C9 C8 112.9(5) . . ?
C11 N3 C17 112.4(6) . . ?
C11 N3 C9 125.3(6) . . ?
C17 N3 C9 122.3(6) . . ?
C11 N4 C13 109.0(6) . . ?
C11 N4 C12 127.3(6) . . ?
C13 N4 C12 123.5(6) . . ?
N4 C11 N3 107.4(6) . . ?
N4 C11 I1 126.5(5) . . ?
N3 C11 I1 126.1(5) . . ?
N4 C12 C14 110.7(6) . . ?
N4 C13 C17 111.0(6) . . ?
C8 C15 C7 122.9(6) 2_666 . ?
C13 C17 N3 100.0(6) . . ?

_refine_diff_density_max         5.437
_refine_diff_density_min         -1.427
_refine_diff_density_rms         0.185

