# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_o-HBDI-I3
_audit_block_doi                 10.5517/ccdc.csd.cc20m3nf
_database_code_depnum_ccdc_archive 'CCDC 1865414'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 I3 N2 O2'
_chemical_formula_sum            'C17 H11 I3 N2 O2'
_chemical_formula_weight         655.98

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.971(3)
_cell_length_b                   6.4819(7)
_cell_length_c                   22.778(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.072(7)
_cell_angle_gamma                90.00
_cell_volume                     3806.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    62931
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.82

_exptl_crystal_description       needle
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2416.0
_exptl_absorpt_coefficient_mu    4.938
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_T_max  0.597
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            62931
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.82
_reflns_number_total             3630
_reflns_number_gt                3135
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0621P)²+25.8716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3659
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.341001(17) 0.40988(8) 0.134618(17) 0.06183(16) Uani 1 1 d . . .
I1 I 0.732132(16) -0.51842(7) 0.59345(2) 0.06153(16) Uani 1 1 d . . .
I3 I 0.31902(2) 1.05060(7) 0.31361(2) 0.06566(16) Uani 1 1 d . . .
O2 O 0.53488(15) 0.2535(7) 0.49790(16) 0.0506(9) Uani 1 1 d . . .
O1 O 0.42652(17) 0.2713(7) 0.24813(18) 0.0635(12) Uani 1 1 d . . .
H1 H 0.4500 0.2246 0.2766 0.095 Uiso 1 1 calc R . .
C6 C 0.6237(2) -0.4030(9) 0.5211(3) 0.0479(13) Uani 1 1 d . . .
H6 H 0.6164 -0.5339 0.5331 0.057 Uiso 1 1 calc R . .
N2 N 0.49810(18) 0.1355(8) 0.33974(19) 0.0484(11) Uani 1 1 d . . .
C2 C 0.6850(2) -0.1344(10) 0.5227(3) 0.0553(15) Uani 1 1 d . . .
H2 H 0.7189 -0.0855 0.5359 0.066 Uiso 1 1 calc R . .
C8 C 0.49151(19) 0.2641(8) 0.3867(2) 0.0389(11) Uani 1 1 d . . .
N1 N 0.55488(17) 0.0342(7) 0.4277(2) 0.0433(10) Uani 1 1 d . . .
C14 C 0.3402(2) 0.7023(9) 0.2360(2) 0.0436(12) Uani 1 1 d . . .
H14 H 0.3129 0.7611 0.2057 0.052 Uiso 1 1 calc R . .
C1 C 0.67319(19) -0.3285(8) 0.5387(2) 0.0394(11) Uani 1 1 d . . .
C3 C 0.6454(2) -0.0123(9) 0.4865(3) 0.0525(14) Uani 1 1 d . . .
H3 H 0.6525 0.1195 0.4750 0.063 Uiso 1 1 calc R . .
C9 C 0.52792(19) 0.1942(8) 0.4455(2) 0.0395(11) Uani 1 1 d . . .
C5 C 0.5845(2) -0.2802(10) 0.4849(3) 0.0504(13) Uani 1 1 d . . .
H5 H 0.5506 -0.3289 0.4722 0.060 Uiso 1 1 calc R . .
C15 C 0.3562(2) 0.7859(8) 0.2945(2) 0.0419(11) Uani 1 1 d . . .
C16 C 0.3952(2) 0.6920(8) 0.3395(2) 0.0416(11) Uani 1 1 d . . .
H16 H 0.4048 0.7473 0.3789 0.050 Uiso 1 1 calc R . .
C13 C 0.36516(19) 0.5323(8) 0.2237(2) 0.0385(11) Uani 1 1 d . . .
C4 C 0.5955(2) -0.0872(8) 0.4677(2) 0.0389(11) Uani 1 1 d . . .
C10 C 0.45927(19) 0.4276(8) 0.3809(2) 0.0412(11) Uani 1 1 d . . .
H10 H 0.4620 0.4964 0.4176 0.049 Uiso 1 1 calc R . .
C11 C 0.42114(19) 0.5152(8) 0.3279(2) 0.0369(10) Uani 1 1 d . . .
C12 C 0.4059(2) 0.4332(8) 0.2673(2) 0.0407(11) Uani 1 1 d . . .
C7 C 0.5351(2) 0.0079(10) 0.3645(2) 0.0482(13) Uani 1 1 d . . .
C17 C 0.5557(3) -0.1505(12) 0.3311(3) 0.071(2) Uani 1 1 d . . .
H17A H 0.5830 -0.2257 0.3596 0.107 Uiso 1 1 calc R . .
H17B H 0.5690 -0.0848 0.3011 0.107 Uiso 1 1 calc R . .
H17C H 0.5283 -0.2438 0.3109 0.107 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
I2 C13 2.097(5) . ?
I1 C1 2.106(5) . ?
I3 C15 2.096(5) . ?
O2 C9 1.215(6) . ?
O1 C12 1.322(7) . ?
O1 H1 0.8200 . ?
C6 C1 1.365(8) . ?
C6 C5 1.385(8) . ?
C6 H6 0.9300 . ?
N2 C7 1.292(7) . ?
N2 C8 1.407(7) . ?
C2 C1 1.373(8) . ?
C2 C3 1.390(8) . ?
C2 H2 0.9300 . ?
C8 C10 1.353(7) . ?
C8 C9 1.481(7) . ?
N1 C7 1.390(7) . ?
N1 C9 1.394(7) . ?
N1 C4 1.437(6) . ?
C14 C13 1.363(8) . ?
C14 C15 1.385(8) . ?
C14 H14 0.9300 . ?
C3 C4 1.374(8) . ?
C3 H3 0.9300 . ?
C5 C4 1.369(8) . ?
C5 H5 0.9300 . ?
C15 C16 1.377(7) . ?
C16 C11 1.408(7) . ?
C16 H16 0.9300 . ?
C13 C12 1.401(7) . ?
C10 C11 1.453(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.421(7) . ?
C7 C17 1.479(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 H1 109.5 . . ?
C1 C6 C5 118.8(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C7 N2 C8 107.5(4) . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C10 C8 N2 127.7(5) . . ?
C10 C8 C9 124.3(5) . . ?
N2 C8 C9 108.0(4) . . ?
C7 N1 C9 108.6(4) . . ?
C7 N1 C4 125.3(4) . . ?
C9 N1 C4 126.1(4) . . ?
C13 C14 C15 118.8(5) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C6 C1 C2 122.0(5) . . ?
C6 C1 I1 118.1(4) . . ?
C2 C1 I1 120.0(4) . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O2 C9 N1 125.3(5) . . ?
O2 C9 C8 131.5(5) . . ?
N1 C9 C8 103.2(4) . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 I3 119.2(4) . . ?
C16 C15 I3 121.0(4) . . ?
C15 C16 C11 122.3(5) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
C14 C13 C12 123.8(5) . . ?
C14 C13 I2 118.2(4) . . ?
C12 C13 I2 118.0(4) . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 N1 119.5(5) . . ?
C3 C4 N1 119.9(5) . . ?
C8 C10 C11 131.6(5) . . ?
C8 C10 H10 114.2 . . ?
C11 C10 H10 114.2 . . ?
C16 C11 C12 117.9(5) . . ?
C16 C11 C10 115.5(4) . . ?
C12 C11 C10 126.4(5) . . ?
O1 C12 C13 116.6(5) . . ?
O1 C12 C11 126.0(5) . . ?
C13 C12 C11 117.4(5) . . ?
N2 C7 N1 112.7(5) . . ?
N2 C7 C17 125.3(5) . . ?
N1 C7 C17 122.0(5) . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.82
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.335
_refine_diff_density_min         -2.074
_refine_diff_density_rms         0.615
####################################################################### 
# 
# 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_o-MBDI-I3
_audit_block_doi                 10.5517/ccdc.csd.cc20m3pg
_database_code_depnum_ccdc_archive 'CCDC 1865415'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_audit_creation_date             2018-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C18 H13 I3 N2 O2), C2 O'
_chemical_formula_sum            'C38 H26 I6 N4 O5'
_chemical_formula_weight         1380.03
_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'
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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   4.2188(2)
_cell_length_b                   32.6154(16)
_cell_length_c                   15.1566(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.303(3)
_cell_angle_gamma                90.00
_cell_volume                     2083.83(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9621
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.50
_exptl_absorpt_coefficient_mu    4.518
_exptl_absorpt_correction_T_max  0.581
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    2.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53472
_diffrn_reflns_theta_full        25.74
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         2.31
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2686
_reflns_number_total             3959
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.083
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.179
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0237P)²+23.0284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1166
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_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:
 C14(H14), C12(H12), C10(H10), C3(H3), C5(H5), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I2 I 1.43685(19) 0.67399(2) 0.42477(5) 0.0383(2) Uani 1 d . . 1 . . .
I3 I 0.8030(2) 0.61043(2) 0.09279(5) 0.0498(3) Uani 1 d . . 1 . . .
I1 I 1.2795(2) 1.06429(2) 0.12236(6) 0.0497(3) Uani 1 d . . 1 . . .
C16 C 0.889(3) 0.7002(3) 0.1409(6) 0.031(3) Uani 1 d . . 1 . . .
C15 C 0.962(3) 0.6607(3) 0.1699(6) 0.031(3) Uani 1 d . . 1 . . .
C11 C 0.982(3) 0.7333(3) 0.1965(6) 0.030(2) Uani 1 d . . 1 . . .
C14 C 1.120(3) 0.6528(3) 0.2493(7) 0.036(3) Uani 1 d . . 1 . . .
H14 H 1.1640 0.6261 0.2675 0.043 Uiso 1 calc . . 1 R . .
N2 N 1.176(2) 0.8179(3) 0.2791(5) 0.041(2) Uani 1 d . . 1 . . .
C12 C 1.148(3) 0.7259(3) 0.2756(6) 0.031(3) Uani 1 d . . 1 . . .
H12 H 1.2164 0.7477 0.3112 0.037 Uiso 1 calc . . 1 R . .
C10 C 0.902(3) 0.7751(3) 0.1656(7) 0.037(3) Uani 1 d . . 1 . . .
H10 H 0.7767 0.7768 0.1139 0.044 Uiso 1 calc . . 1 R . .
C8 C 0.988(3) 0.8109(3) 0.2024(7) 0.040(3) Uani 1 d . . 1 . . .
N1 N 1.049(2) 0.8790(2) 0.2163(5) 0.038(2) Uani 1 d . . 1 . . .
C4 C 1.082(3) 0.9216(3) 0.1954(7) 0.039(3) Uani 1 d . . 1 . . .
C17 C 1.389(3) 0.8776(4) 0.3584(8) 0.054(4) Uani 1 d . . 1 . . .
H17A H 1.2454 0.8901 0.3980 0.081 Uiso 1 calc . . 1 GR . .
H17B H 1.5243 0.8983 0.3351 0.081 Uiso 1 calc . . 1 GR . .
H17C H 1.5158 0.8575 0.3896 0.081 Uiso 1 calc . . 1 GR . .
C7 C 1.205(3) 0.8575(3) 0.2845(7) 0.039(3) Uani 1 d . . 1 . . .
C9 C 0.897(3) 0.8504(3) 0.1604(7) 0.037(3) Uani 1 d . . 1 . . .
O1 O 0.7248(18) 0.7070(2) 0.0627(4) 0.0382(19) Uani 1 d . . 1 . . .
O2 O 0.734(2) 0.8583(2) 0.0963(5) 0.063(3) Uani 1 d . . 1 . . .
C3 C 1.204(3) 0.9322(3) 0.1158(7) 0.048(3) Uani 1 d . . 1 . . .
H3 H 1.2547 0.9119 0.0756 0.058 Uiso 1 calc . . 1 R . .
C5 C 1.008(4) 0.9521(4) 0.2537(8) 0.062(4) Uani 1 d . . 1 . . .
H5 H 0.9237 0.9453 0.3076 0.075 Uiso 1 calc . . 1 R . .
C2 C 1.251(3) 0.9731(3) 0.0956(8) 0.055(4) Uani 1 d . . 1 . . .
H2 H 1.3328 0.9801 0.0415 0.066 Uiso 1 calc . . 1 R . .
C6 C 1.058(4) 0.9928(3) 0.2322(8) 0.061(4) Uani 1 d . . 1 . . .
H6 H 1.0073 1.0135 0.2716 0.073 Uiso 1 calc . . 1 R . .
C13 C 1.212(3) 0.6860(3) 0.3012(7) 0.032(3) Uani 1 d . . 1 . . .
C1 C 1.182(3) 1.0025(3) 0.1528(7) 0.040(3) Uani 1 d . . 1 . . .
C18 C 0.916(3) 0.7133(4) -0.0114(7) 0.059(4) Uani 1 d . . 1 . . .
H18A H 0.7830 0.7207 -0.0618 0.089 Uiso 1 calc . . 1 GR . .
H18B H 1.0284 0.6885 -0.0238 0.089 Uiso 1 calc . . 1 GR . .
H18C H 1.0649 0.7349 0.0014 0.089 Uiso 1 calc . . 1 GR . .
O3 O 1.0000 1.0000 0.5000 0.232(14) Uiso 1 d . . 2 S T P
C19 C 0.649(7) 1.0008(12) 0.490(3) 0.211(14) Uiso 1 d . . 1 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C13 2.102(10) . ?
I3 C15 2.107(9) . ?
I1 C1 2.112(10) . ?
C16 C15 1.392(13) . ?
C16 C11 1.416(14) . ?
C16 O1 1.366(12) . ?
C15 C14 1.376(14) . ?
C11 C12 1.385(14) . ?
C11 C10 1.477(13) . ?
C14 C13 1.384(14) . ?
N2 C8 1.400(14) . ?
N2 C7 1.302(13) . ?
C12 C13 1.382(13) . ?
C10 C8 1.336(14) . ?
C8 C9 1.481(14) . ?
N1 C4 1.433(13) . ?
N1 C7 1.392(14) . ?
N1 C9 1.400(13) . ?
C4 C3 1.376(15) . ?
C4 C5 1.373(15) . ?
C17 C7 1.489(15) . ?
C9 O2 1.195(13) . ?
O1 C18 1.424(13) . ?
C3 C2 1.384(14) . ?
C5 C6 1.387(16) . ?
C2 C1 1.334(14) . ?
C6 C1 1.369(15) . ?
O3 C19 1.48(3) . ?
O3 C19 1.48(3) 3_776 ?
C19 C19 1.30(6) 3_676 ?

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
C15 C16 C11 117.7(9) . . ?
O1 C16 C15 121.5(9) . . ?
O1 C16 C11 120.8(9) . . ?
C16 C15 I3 118.8(7) . . ?
C14 C15 I3 118.2(7) . . ?
C14 C15 C16 122.9(9) . . ?
C16 C11 C10 117.5(9) . . ?
C12 C11 C16 120.1(9) . . ?
C12 C11 C10 122.3(9) . . ?
C15 C14 C13 117.8(9) . . ?
C7 N2 C8 105.2(9) . . ?
C13 C12 C11 119.5(9) . . ?
C8 C10 C11 128.3(10) . . ?
N2 C8 C9 110.1(9) . . ?
C10 C8 N2 128.6(10) . . ?
C10 C8 C9 121.3(10) . . ?
C7 N1 C4 127.2(9) . . ?
C7 N1 C9 107.7(8) . . ?
C9 N1 C4 124.1(9) . . ?
C3 C4 N1 118.7(9) . . ?
C5 C4 N1 122.2(10) . . ?
C5 C4 C3 119.1(10) . . ?
N2 C7 N1 114.4(10) . . ?
N2 C7 C17 122.0(10) . . ?
N1 C7 C17 123.6(10) . . ?
N1 C9 C8 102.5(9) . . ?
O2 C9 C8 131.9(10) . . ?
O2 C9 N1 125.6(10) . . ?
C16 O1 C18 115.2(9) . . ?
C4 C3 C2 119.8(10) . . ?
C4 C5 C6 120.1(11) . . ?
C1 C2 C3 120.8(11) . . ?
C1 C6 C5 119.6(11) . . ?
C14 C13 I2 117.8(7) . . ?
C12 C13 I2 120.1(7) . . ?
C12 C13 C14 122.0(10) . . ?
C2 C1 I1 119.7(8) . . ?
C2 C1 C6 120.5(10) . . ?
C6 C1 I1 119.8(8) . . ?
C19 O3 C19 179.998(3) . 3_776 ?
C19 C19 O3 161(5) 3_676 . ?

_olex2_submission_special_instructions 'No special instructions were received'
