# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_antonkinn231228
_database_code_depnum_ccdc_archive 'CCDC 2364396'
loop_
_audit_author_name
_audit_author_address
'Pim Puylaert'
;University of Bremen
Germany
;
_audit_update_record             
;
2024-06-21 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_antonkinn231228     
;
PROBLEM: Hirshfeld Test Diff for    I1       --N2       .        9.0 s.u.
RESPONSE: Due to the ortho substitution pattern, some interaction between I1 and N2 is enforced, leading to a Hirshfeld test, although strictly there is no chemical bond between the two atoms. This is a common alert for such compounds.
;
# Added during the CSD deposition process: Friday 21 June 2024 02:49 PM
# end Validation Reply Form

_audit_creation_date             2024-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 I N2 O2'
_chemical_formula_sum            'C13 H9 I N2 O2'
_chemical_formula_weight         352.12
_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      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                   6.5622(6)
_cell_length_b                   11.6742(8)
_cell_length_c                   15.1234(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.555(3)
_cell_angle_gamma                90
_cell_volume                     1157.43(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      36.368
_cell_measurement_theta_min      2.207
_shelx_estimated_absorpt_T_max   0.770
_shelx_estimated_absorpt_T_min   0.288
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0936 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8632.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33426
_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         36.351
_diffrn_reflns_theta_min         3.107
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus Ims X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5131
_reflns_number_total             5599
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0185
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0116P)²+0.8199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0411
_refine_ls_wR_factor_ref         0.0424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C4(H4), C3(H3), C2(H2), C9(H9), C10(H10), C11(H11), C8(H8)
;
_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 0.25018(2) 0.53497(2) 0.45328(2) 0.00967(2) Uani 1 1 d . . . . .
O1 O 0.11439(14) 0.59242(8) 0.54527(6) 0.01479(16) Uani 1 1 d . . . . .
O2 O 0.48519(14) 0.61525(8) 0.46545(6) 0.01492(16) Uani 1 1 d . . . . .
N2 N 0.41252(16) 0.49883(10) 0.29846(7) 0.01313(17) Uani 1 1 d . . . . .
N1 N 0.34113(16) 0.58235(9) 0.24168(7) 0.01150(16) Uani 1 1 d . . . . .
C5 C 0.05635(19) 0.71097(11) 0.20521(8) 0.0137(2) Uani 1 1 d . . . . .
H5 H 0.097796 0.716499 0.145973 0.016 Uiso 1 1 calc R U . . .
C6 C 0.16818(17) 0.64371(10) 0.26633(7) 0.01067(18) Uani 1 1 d . . . . .
C1 C 0.10218(18) 0.63704(10) 0.35331(7) 0.01103(18) Uani 1 1 d . . . . .
C13 C 0.5752(2) 0.45348(11) 0.26438(9) 0.0145(2) Uani 1 1 d . . . . .
H13 H 0.655395 0.394155 0.291253 0.017 Uiso 1 1 calc R U . . .
C4 C -0.1151(2) 0.76977(11) 0.23072(8) 0.0155(2) Uani 1 1 d . . . . .
H4 H -0.189360 0.815664 0.188617 0.019 Uiso 1 1 calc R U . . .
C3 C -0.18030(19) 0.76273(12) 0.31695(9) 0.0159(2) Uani 1 1 d . . . . .
H3 H -0.297751 0.803501 0.333742 0.019 Uiso 1 1 calc R U . . .
C12 C 0.61436(19) 0.50548(11) 0.18187(8) 0.0136(2) Uani 1 1 d . . . . .
C7 C 0.46239(18) 0.59035(10) 0.16934(8) 0.01154(18) Uani 1 1 d . . . . .
C2 C -0.07084(19) 0.69511(11) 0.37812(8) 0.0137(2) Uani 1 1 d . . . . .
H2 H -0.114565 0.688651 0.436954 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6076(2) 0.64591(12) 0.03504(9) 0.0173(2) Uani 1 1 d . . . . .
H9 H 0.609470 0.694090 -0.015541 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7550(2) 0.55909(13) 0.04519(9) 0.0203(3) Uani 1 1 d . . . . .
H10 H 0.851298 0.548583 0.000841 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7619(2) 0.48884(12) 0.11865(9) 0.0182(2) Uani 1 1 d . . . . .
H11 H 0.863134 0.431085 0.126202 0.022 Uiso 1 1 calc R U . . .
C8 C 0.45998(19) 0.66382(11) 0.09587(8) 0.0145(2) Uani 1 1 d . . . . .
H8 H 0.361499 0.723072 0.088332 0.017 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 O1 1.8138(9) . ?
I1 O2 1.8070(9) . ?
I1 C1 2.1256(11) . ?
N2 N1 1.3680(14) . ?
N2 C13 1.3172(16) . ?
N1 C6 1.4064(15) . ?
N1 C7 1.3843(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3961(17) . ?
C5 C4 1.3872(17) . ?
C6 C1 1.4052(16) . ?
C1 C2 1.3883(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.4213(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.3929(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.3913(18) . ?
C12 C7 1.4126(17) . ?
C12 C11 1.4039(18) . ?
C7 C8 1.4032(17) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.4047(19) . ?
C9 C8 1.3811(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(2) . ?
C11 H11 0.9500 . ?
C8 H8 0.9500 . ?

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
O1 I1 C1 96.53(4) . . ?
O2 I1 O1 100.16(4) . . ?
O2 I1 C1 98.19(4) . . ?
C13 N2 N1 107.56(10) . . ?
N2 N1 C6 117.03(9) . . ?
N2 N1 C7 110.57(9) . . ?
C7 N1 C6 132.39(10) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.20(11) . . ?
C5 C6 N1 121.17(10) . . ?
C5 C6 C1 118.43(11) . . ?
C1 C6 N1 120.40(10) . . ?
C6 C1 I1 123.14(8) . . ?
C2 C1 I1 115.77(8) . . ?
C2 C1 C6 121.06(11) . . ?
N2 C13 H13 124.7 . . ?
N2 C13 C12 110.68(11) . . ?
C12 C13 H13 124.7 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.20(11) . . ?
C3 C4 H4 119.4 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.00(11) . . ?
C2 C3 H3 120.5 . . ?
C7 C12 C13 105.26(10) . . ?
C11 C12 C13 134.09(12) . . ?
C11 C12 C7 120.65(12) . . ?
N1 C7 C12 105.90(10) . . ?
N1 C7 C8 132.88(11) . . ?
C8 C7 C12 121.19(11) . . ?
C1 C2 C3 120.10(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.43(12) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.97(12) . . ?
C11 C10 H10 119.5 . . ?
C12 C11 H11 121.1 . . ?
C10 C11 C12 117.84(12) . . ?
C10 C11 H11 121.1 . . ?
C7 C8 H8 121.6 . . ?
C9 C8 C7 116.84(11) . . ?
C9 C8 H8 121.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 -178.98(10) . . . . ?
N2 N1 C6 C5 -165.06(11) . . . . ?
N2 N1 C6 C1 13.94(16) . . . . ?
N2 N1 C7 C12 1.09(14) . . . . ?
N2 N1 C7 C8 -176.88(13) . . . . ?
N2 C13 C12 C7 1.66(15) . . . . ?
N2 C13 C12 C11 -178.69(15) . . . . ?
N1 N2 C13 C12 -1.01(15) . . . . ?
N1 C6 C1 I1 -0.77(16) . . . . ?
N1 C6 C1 C2 -178.57(11) . . . . ?
N1 C7 C8 C9 -179.69(13) . . . . ?
C5 C6 C1 I1 178.26(9) . . . . ?
C5 C6 C1 C2 0.46(18) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
C6 N1 C7 C12 179.77(12) . . . . ?
C6 N1 C7 C8 1.8(2) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C6 C1 C2 C3 -1.03(19) . . . . ?
C13 N2 N1 C6 -178.97(11) . . . . ?
C13 N2 N1 C7 -0.06(14) . . . . ?
C13 C12 C7 N1 -1.61(14) . . . . ?
C13 C12 C7 C8 176.65(12) . . . . ?
C13 C12 C11 C10 -178.57(15) . . . . ?
C4 C5 C6 N1 179.28(12) . . . . ?
C4 C5 C6 C1 0.26(18) . . . . ?
C4 C3 C2 C1 0.9(2) . . . . ?
C12 C7 C8 C9 2.60(19) . . . . ?
C7 N1 C6 C5 16.3(2) . . . . ?
C7 N1 C6 C1 -164.67(12) . . . . ?
C7 C12 C11 C10 1.0(2) . . . . ?
C9 C10 C11 C12 1.3(2) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C11 C12 C7 N1 178.69(12) . . . . ?
C11 C12 C7 C8 -3.05(19) . . . . ?
C8 C9 C10 C11 -1.7(2) . . . . ?

_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_antonkinn231129
_database_code_depnum_ccdc_archive 'CCDC 2364398'
loop_
_audit_author_name
_audit_author_address
'Pim Puylaert'
;University of Bremen
Germany
;
_audit_update_record             
;
2024-06-21 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 I N3 O2'
_chemical_formula_sum            'C14 H10 I N3 O2'
_chemical_formula_weight         379.15
_chemical_absolute_configuration ?
_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      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   26.9537(8)
_cell_length_b                   26.9537(8)
_cell_length_c                   9.8807(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6216.6(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.6177
_cell_measurement_theta_max      30.0615
_cell_measurement_temperature    100
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    2.322
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.8406.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3312
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            64874
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.562
_diffrn_reflns_theta_min         3.023
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus Ims X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4084
_reflns_number_total             4233
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.723
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0034P)²+45.9474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C5(H5), C3(H3), C6(H6), C10(H10), C14(H14), C11(H11),
 C13(H13), C12(H12)
;
_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 0.02487(2) 0.32431(2) 0.33420(4) 0.01424(6) Uani 1 1 d . . . . .
O1 O 0.00171(15) 0.27118(15) 0.4698(3) 0.0182(7) Uani 1 1 d . . . . .
N1 N 0.15985(17) 0.37324(18) 0.4332(4) 0.0180(8) Uani 1 1 d . . . . .
O2 O -0.02664(15) 0.28159(15) 0.2060(4) 0.0194(7) Uani 1 1 d . . . . .
N2 N 0.11994(18) 0.38539(19) 0.4783(5) 0.0194(8) Uani 1 1 d . . . . .
C4 C 0.1154(2) 0.2569(2) 0.1102(5) 0.0217(10) Uani 1 1 d . . . . .
H4 H 0.105751 0.231043 0.036465 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2098(2) 0.4047(2) 0.5007(5) 0.0196(9) Uani 1 1 d . . . . .
H7 H 0.244743 0.404703 0.488829 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1687(2) 0.2793(2) 0.1722(6) 0.0221(10) Uani 1 1 d . . . . .
H5 H 0.195240 0.268436 0.140760 0.027 Uiso 1 1 calc R U . . .
N3 N 0.14268(18) 0.42396(19) 0.5730(4) 0.0217(9) Uani 1 1 d . . . . .
C2 C 0.0907(2) 0.3099(2) 0.2645(5) 0.0170(9) Uani 1 1 d . . . . .
C3 C 0.0762(2) 0.2724(2) 0.1562(6) 0.0209(10) Uani 1 1 d . . . . .
H3 H 0.039890 0.257371 0.113868 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1981(2) 0.4367(2) 0.5908(5) 0.0196(9) Uani 1 1 d . . . . .
C6 C 0.1836(2) 0.3174(2) 0.2794(5) 0.0214(10) Uani 1 1 d . . . . .
H6 H 0.220153 0.332630 0.321020 0.026 Uiso 1 1 calc R U . . .
C1 C 0.1447(2) 0.3332(2) 0.3257(6) 0.0185(9) Uani 1 1 d . . . . .
C10 C 0.2881(2) 0.4873(2) 0.7276(5) 0.0226(10) Uani 1 1 d . . . . .
H10 H 0.302203 0.465320 0.684573 0.027 Uiso 1 1 calc R U . . .
C14 C 0.2146(2) 0.5121(2) 0.7576(6) 0.0277(11) Uani 1 1 d . . . . .
H14 H 0.178382 0.507476 0.733453 0.033 Uiso 1 1 calc R U . . .
C9 C 0.2345(2) 0.4795(2) 0.6925(5) 0.0213(9) Uani 1 1 d . . . . .
C11 C 0.3207(2) 0.5272(2) 0.8256(6) 0.0285(11) Uani 1 1 d . . . . .
H11 H 0.357344 0.532798 0.848848 0.034 Uiso 1 1 calc R U . . .
C13 C 0.2468(3) 0.5509(3) 0.8562(7) 0.0331(13) Uani 1 1 d . . . . .
H13 H 0.232282 0.572072 0.901343 0.040 Uiso 1 1 calc R U . . .
C12 C 0.3001(2) 0.5592(3) 0.8901(6) 0.0309(12) Uani 1 1 d . . . . .
H12 H 0.322645 0.586537 0.957023 0.037 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 O1 1.828(3) . ?
I1 O2 1.806(3) . ?
I1 C2 2.113(5) . ?
N1 N2 1.347(6) . ?
N1 C7 1.354(6) . ?
N1 C1 1.421(7) . ?
N2 N3 1.302(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(7) . ?
C4 C3 1.391(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(7) . ?
N3 C8 1.365(6) . ?
C2 C3 1.388(7) . ?
C2 C1 1.400(7) . ?
C3 H3 0.9500 . ?
C8 C9 1.473(7) . ?
C6 H6 0.9500 . ?
C6 C1 1.392(7) . ?
C10 H10 0.9500 . ?
C10 C9 1.394(7) . ?
C10 C11 1.386(7) . ?
C14 H14 0.9500 . ?
C14 C9 1.397(7) . ?
C14 C13 1.373(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(8) . ?
C12 H12 0.9500 . ?

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
O1 I1 C2 94.83(17) . . ?
O2 I1 O1 99.34(16) . . ?
O2 I1 C2 95.92(18) . . ?
N2 N1 C7 110.4(4) . . ?
N2 N1 C1 118.1(4) . . ?
C7 N1 C1 131.5(4) . . ?
N3 N2 N1 108.5(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(5) . . ?
N1 C7 H7 128.0 . . ?
N1 C7 C8 104.1(4) . . ?
C8 C7 H7 128.0 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.6 . . ?
N2 N3 C8 108.2(4) . . ?
C3 C2 I1 115.4(4) . . ?
C3 C2 C1 120.7(5) . . ?
C1 C2 I1 123.8(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C7 C8 C9 131.0(5) . . ?
N3 C8 C7 108.7(4) . . ?
N3 C8 C9 120.2(4) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C1 119.6(5) . . ?
C1 C6 H6 120.2 . . ?
C2 C1 N1 120.2(4) . . ?
C6 C1 N1 120.2(4) . . ?
C6 C1 C2 119.6(5) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C11 C10 C9 119.9(5) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C9 120.6(5) . . ?
C10 C9 C8 121.6(5) . . ?
C10 C9 C14 119.0(5) . . ?
C14 C9 C8 119.3(5) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.4(5) . . ?
C12 C13 H13 119.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C2 C3 C4 -175.1(4) . . . . ?
I1 C2 C1 N1 -6.2(7) . . . . ?
I1 C2 C1 C6 174.6(4) . . . . ?
N1 N2 N3 C8 -0.6(5) . . . . ?
N1 C7 C8 N3 -0.7(6) . . . . ?
N1 C7 C8 C9 -179.7(5) . . . . ?
N2 N1 C7 C8 0.4(5) . . . . ?
N2 N1 C1 C2 3.6(7) . . . . ?
N2 N1 C1 C6 -177.3(5) . . . . ?
N2 N3 C8 C7 0.8(6) . . . . ?
N2 N3 C8 C9 179.9(5) . . . . ?
C4 C5 C6 C1 0.2(8) . . . . ?
C7 N1 N2 N3 0.1(6) . . . . ?
C7 N1 C1 C2 -174.2(5) . . . . ?
C7 N1 C1 C6 5.0(8) . . . . ?
C7 C8 C9 C10 -10.9(9) . . . . ?
C7 C8 C9 C14 170.6(6) . . . . ?
C5 C4 C3 C2 -0.4(8) . . . . ?
C5 C6 C1 N1 -178.4(5) . . . . ?
C5 C6 C1 C2 0.7(8) . . . . ?
N3 C8 C9 C10 170.2(5) . . . . ?
N3 C8 C9 C14 -8.3(7) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C3 C2 C1 N1 177.6(5) . . . . ?
C3 C2 C1 C6 -1.5(7) . . . . ?
C1 N1 N2 N3 -178.0(4) . . . . ?
C1 N1 C7 C8 178.2(5) . . . . ?
C1 C2 C3 C4 1.4(8) . . . . ?
C10 C11 C12 C13 0.1(9) . . . . ?
C14 C13 C12 C11 -1.3(10) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C9 C14 C13 C12 1.6(10) . . . . ?
C11 C10 C9 C8 -178.8(5) . . . . ?
C11 C10 C9 C14 -0.3(8) . . . . ?
C13 C14 C9 C8 177.7(5) . . . . ?
C13 C14 C9 C10 -0.8(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_antonkinn231212
_database_code_depnum_ccdc_archive 'CCDC 2364397'
loop_
_audit_author_name
_audit_author_address
'Pim Puylaert'
;University of Bremen
Germany
;
_audit_update_record             
;
2024-06-21 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_antonkinn231212     
;
PROBLEM: Hirshfeld Test Diff for    I1       --N2       .        8.7 s.u.
RESPONSE: Due to the ortho substitution pattern, some interaction between I1 and N2 is enforced, leading to a Hirshfeld test, although strictly there is no chemical bond between the two atoms. This is a common alert for such compounds.
;
# Added during the CSD deposition process: Friday 21 June 2024 02:49 PM
# end Validation Reply Form

_audit_creation_date             2024-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 I N2 O5, C H2 Cl2'
_chemical_formula_sum            'C18 H17 Cl2 I N2 O5'
_chemical_formula_weight         539.14
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.2341(4)
_cell_length_b                   14.6267(4)
_cell_length_c                   17.4417(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3886.44(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9709
_cell_measurement_theta_max      36.303
_cell_measurement_theta_min      2.334
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0655 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.8842.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.113
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            61224
_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         36.344
_diffrn_reflns_theta_min         2.674
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus Ims X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8720
_reflns_number_total             9432
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         9432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0141P)²+2.4030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0469
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C13(H13), C11(H11), C8(H8), C9(H9), C3(H3), C4(H4), C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_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 0.62864(2) 0.61008(2) 0.70359(2) 0.00900(2) Uani 1 1 d . . . . .
Cl1 Cl 0.44140(2) 0.62445(2) 0.85672(2) 0.01952(5) Uani 1 1 d . . . . .
Cl2 Cl 0.48183(2) 0.62430(3) 1.02052(2) 0.02453(6) Uani 1 1 d . . . . .
O1 O 0.74232(5) 0.62045(7) 0.72454(5) 0.01822(16) Uani 1 1 d . . . . .
O3 O 0.62972(6) 0.48806(6) 0.82982(5) 0.02010(17) Uani 1 1 d . . . . .
O2 O 0.63239(6) 0.46447(6) 0.70362(5) 0.01676(15) Uani 1 1 d . . . . .
O4 O 0.61888(6) 0.74883(5) 0.66898(5) 0.01450(14) Uani 1 1 d . . . . .
O5 O 0.60263(7) 0.77179(7) 0.79461(5) 0.02187(18) Uani 1 1 d . . . . .
N2 N 0.47148(6) 0.60167(6) 0.63819(5) 0.01154(14) Uani 1 1 d . . . . .
N1 N 0.48411(6) 0.61521(6) 0.56114(5) 0.01016(14) Uani 1 1 d . . . . .
C2 C 0.72437(7) 0.57339(7) 0.55991(6) 0.01277(17) Uani 1 1 d . . . . .
H2 H 0.770496 0.566093 0.596055 0.015 Uiso 1 1 calc R U . . .
C14 C 0.63169(8) 0.43525(8) 0.77533(7) 0.01563(18) Uani 1 1 d . . . . .
C5 C 0.58751(7) 0.59371(7) 0.45523(6) 0.01196(16) Uani 1 1 d . . . . .
H5 H 0.541462 0.600076 0.418897 0.014 Uiso 1 1 calc R U . . .
C13 C 0.38866(7) 0.61958(7) 0.65312(6) 0.01240(16) Uani 1 1 d . . . . .
H13 H 0.362584 0.615512 0.702477 0.015 Uiso 1 1 calc R U . . .
C12 C 0.34352(7) 0.64582(7) 0.58539(6) 0.01061(15) Uani 1 1 d . . . . .
C11 C 0.25668(7) 0.67244(8) 0.57049(6) 0.01348(17) Uani 1 1 d . . . . .
H11 H 0.214331 0.675431 0.610392 0.016 Uiso 1 1 calc R U . . .
C1 C 0.63981(6) 0.59146(7) 0.58454(6) 0.01005(15) Uani 1 1 d . . . . .
C8 C 0.38440(7) 0.66486(8) 0.45076(6) 0.01361(17) Uani 1 1 d . . . . .
H8 H 0.426418 0.662704 0.410559 0.016 Uiso 1 1 calc R U . . .
C9 C 0.29848(7) 0.69043(8) 0.43753(6) 0.01599(18) Uani 1 1 d . . . . .
H9 H 0.281511 0.706207 0.386816 0.019 Uiso 1 1 calc R U . . .
C6 C 0.56944(6) 0.60080(6) 0.53339(5) 0.00909(14) Uani 1 1 d . . . . .
C16 C 0.60855(8) 0.80221(7) 0.72958(7) 0.01467(17) Uani 1 1 d . . . . .
C15 C 0.63428(10) 0.33348(9) 0.78377(8) 0.0244(3) Uani 1 1 d . . . . .
H15A H 0.693953 0.311499 0.773739 0.037 Uiso 1 1 calc R U . . .
H15B H 0.593601 0.305578 0.747067 0.037 Uiso 1 1 calc R U . . .
H15C H 0.616984 0.316717 0.836029 0.037 Uiso 1 1 calc R U . . .
C18 C 0.52445(8) 0.63599(9) 0.92682(7) 0.01750(19) Uani 1 1 d . . . . .
H18A H 0.570036 0.588854 0.918214 0.021 Uiso 1 1 calc R U . . .
H18B H 0.552483 0.696732 0.921587 0.021 Uiso 1 1 calc R U . . .
C3 C 0.74127(7) 0.56599(8) 0.48193(6) 0.01381(17) Uani 1 1 d . . . . .
H3 H 0.798960 0.553332 0.464187 0.017 Uiso 1 1 calc R U . . .
C7 C 0.40660(6) 0.64224(7) 0.52641(6) 0.00993(15) Uani 1 1 d . . . . .
C4 C 0.67306(7) 0.57729(7) 0.43032(6) 0.01318(17) Uani 1 1 d . . . . .
H4 H 0.684761 0.573791 0.376905 0.016 Uiso 1 1 calc R U . . .
C10 C 0.23502(7) 0.69407(8) 0.49609(7) 0.01546(18) Uani 1 1 d . . . . .
H10 H 0.176574 0.711662 0.484114 0.019 Uiso 1 1 calc R U . . .
C17 C 0.60674(10) 0.90235(8) 0.71083(8) 0.0230(2) Uani 1 1 d . . . . .
H17A H 0.666852 0.924357 0.703092 0.034 Uiso 1 1 calc R U . . .
H17B H 0.579596 0.936002 0.753241 0.034 Uiso 1 1 calc R U . . .
H17C H 0.572593 0.912084 0.663917 0.034 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 O1 1.7765(8) . ?
I1 O2 2.1306(9) . ?
I1 O4 2.1226(8) . ?
I1 C1 2.1011(10) . ?
Cl1 C18 1.7675(12) . ?
Cl2 C18 1.7669(12) . ?
O3 C14 1.2252(15) . ?
O2 C14 1.3217(14) . ?
O4 C16 1.3234(14) . ?
O5 C16 1.2217(14) . ?
N2 N1 1.3720(12) . ?
N2 C13 1.3146(14) . ?
N1 C6 1.4030(13) . ?
N1 C7 1.3848(13) . ?
C2 H2 0.9500 . ?
C2 C1 1.3834(14) . ?
C2 C3 1.3885(15) . ?
C14 C15 1.4963(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3946(14) . ?
C5 C4 1.3946(15) . ?
C13 H13 0.9500 . ?
C13 C12 1.4198(15) . ?
C12 C11 1.4032(14) . ?
C12 C7 1.4087(14) . ?
C11 H11 0.9500 . ?
C11 C10 1.3759(16) . ?
C1 C6 1.4014(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3806(15) . ?
C8 C7 1.4016(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.4075(16) . ?
C16 C17 1.5011(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C4 1.3847(15) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 I1 O2 93.39(4) . . ?
O1 I1 O4 92.59(4) . . ?
O1 I1 C1 97.78(4) . . ?
O4 I1 O2 163.29(3) . . ?
C1 I1 O2 82.44(3) . . ?
C1 I1 O4 81.29(4) . . ?
C14 O2 I1 108.86(7) . . ?
C16 O4 I1 110.20(7) . . ?
C13 N2 N1 107.45(9) . . ?
N2 N1 C6 116.50(8) . . ?
N2 N1 C7 110.49(8) . . ?
C7 N1 C6 133.01(9) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.45(10) . . ?
C3 C2 H2 120.3 . . ?
O3 C14 O2 122.03(11) . . ?
O3 C14 C15 123.47(11) . . ?
O2 C14 C15 114.49(10) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.12(9) . . ?
C4 C5 H5 119.9 . . ?
N2 C13 H13 124.6 . . ?
N2 C13 C12 110.73(9) . . ?
C12 C13 H13 124.6 . . ?
C11 C12 C13 133.29(10) . . ?
C11 C12 C7 121.21(9) . . ?
C7 C12 C13 105.49(9) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 C12 117.69(10) . . ?
C10 C11 H11 121.2 . . ?
C2 C1 I1 114.02(7) . . ?
C2 C1 C6 122.23(9) . . ?
C6 C1 I1 123.68(7) . . ?
C9 C8 H8 121.6 . . ?
C9 C8 C7 116.75(10) . . ?
C7 C8 H8 121.6 . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.69(10) . . ?
C10 C9 H9 118.7 . . ?
C5 C6 N1 122.09(9) . . ?
C5 C6 C1 117.65(9) . . ?
C1 C6 N1 120.25(9) . . ?
O4 C16 C17 113.82(10) . . ?
O5 C16 O4 122.37(10) . . ?
O5 C16 C17 123.80(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Cl1 C18 H18A 109.3 . . ?
Cl1 C18 H18B 109.3 . . ?
Cl2 C18 Cl1 111.56(6) . . ?
Cl2 C18 H18A 109.3 . . ?
Cl2 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.23(10) . . ?
C4 C3 H3 120.4 . . ?
N1 C7 C12 105.83(8) . . ?
N1 C7 C8 133.23(9) . . ?
C8 C7 C12 120.93(9) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.29(10) . . ?
C3 C4 H4 119.4 . . ?
C11 C10 C9 120.73(10) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 O2 C14 O3 -0.42(14) . . . . ?
I1 O2 C14 C15 -179.91(9) . . . . ?
I1 O4 C16 O5 -2.48(14) . . . . ?
I1 O4 C16 C17 176.34(9) . . . . ?
I1 C1 C6 N1 -6.06(13) . . . . ?
I1 C1 C6 C5 174.98(7) . . . . ?
N2 N1 C6 C5 166.55(9) . . . . ?
N2 N1 C6 C1 -12.36(13) . . . . ?
N2 N1 C7 C12 0.30(11) . . . . ?
N2 N1 C7 C8 179.51(11) . . . . ?
N2 C13 C12 C11 -179.05(11) . . . . ?
N2 C13 C12 C7 0.17(12) . . . . ?
N1 N2 C13 C12 0.02(12) . . . . ?
C2 C1 C6 N1 177.24(9) . . . . ?
C2 C1 C6 C5 -1.71(15) . . . . ?
C2 C3 C4 C5 -1.58(17) . . . . ?
C13 N2 N1 C6 179.14(9) . . . . ?
C13 N2 N1 C7 -0.20(12) . . . . ?
C13 C12 C11 C10 179.76(11) . . . . ?
C13 C12 C7 N1 -0.28(11) . . . . ?
C13 C12 C7 C8 -179.60(10) . . . . ?
C12 C11 C10 C9 -0.72(17) . . . . ?
C11 C12 C7 N1 179.05(9) . . . . ?
C11 C12 C7 C8 -0.27(15) . . . . ?
C1 C2 C3 C4 0.28(16) . . . . ?
C8 C9 C10 C11 0.45(18) . . . . ?
C9 C8 C7 N1 -179.13(11) . . . . ?
C9 C8 C7 C12 -0.02(16) . . . . ?
C6 N1 C7 C12 -178.89(10) . . . . ?
C6 N1 C7 C8 0.32(19) . . . . ?
C6 C5 C4 C3 1.23(16) . . . . ?
C3 C2 C1 I1 -175.61(8) . . . . ?
C3 C2 C1 C6 1.38(16) . . . . ?
C7 N1 C6 C5 -14.29(17) . . . . ?
C7 N1 C6 C1 166.80(10) . . . . ?
C7 C12 C11 C10 0.64(16) . . . . ?
C7 C8 C9 C10 -0.06(17) . . . . ?
C4 C5 C6 N1 -178.53(9) . . . . ?
C4 C5 C6 C1 0.40(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
