# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_monoiodo_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2d45zq
_database_code_depnum_ccdc_archive 'CCDC 2208563'
loop_
_audit_author_name
_audit_author_address
'Gurudutt Dubey'
;IIT Gandhinagar
India
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_monoiodo_0m_a       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         68 Report
RESPONSE: These reflections were probably affected by unexpected deviations in their intensities for symmetry equivalent measurements and omitted during initial data reduction.
;
# Added during the CSD deposition process: Wednesday 21 September 2022 10:59 AM
# end Validation Reply Form

_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        Monoiodo_diarylcyanostilbene
_chemical_formula_moiety         'C17 H15 I N2'
_chemical_formula_sum            'C17 H15 I N2'
_chemical_formula_weight         374.21
_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'

_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                   11.3563(4)
_cell_length_b                   6.0912(2)
_cell_length_c                   22.4406(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.1290(10)
_cell_angle_gamma                90
_cell_volume                     1536.70(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      56.509
_cell_measurement_theta_min      4.777
_shelx_estimated_absorpt_T_max   0.790
_shelx_estimated_absorpt_T_min   0.545
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2- Bruker AXS area detector scaling and absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.119
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27580
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_min         1.811
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3242
_reflns_number_total             3737
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.8310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0957
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C9(H9), C12(H12), C3(H3), C15(H15), C2(H2), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), 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 0.17545(2) 0.56079(4) 0.51237(2) 0.07726(12) Uani 1 1 d . . . . .
N2 N 0.9575(2) 0.4081(3) 0.15076(10) 0.0572(5) Uani 1 1 d . . . . .
C13 C 0.8737(2) 0.4147(4) 0.18850(10) 0.0465(5) Uani 1 1 d . . . . .
C10 C 0.6986(2) 0.4238(4) 0.26853(10) 0.0469(5) Uani 1 1 d . . . . .
C7 C 0.57522(18) 0.3196(4) 0.35098(10) 0.0459(4) Uani 1 1 d . . . . .
C4 C 0.48325(18) 0.3787(4) 0.38911(10) 0.0448(4) Uani 1 1 d . . . . .
C11 C 0.7792(2) 0.2504(4) 0.26836(12) 0.0546(5) Uani 1 1 d . . . . .
H11 H 0.775388 0.134460 0.294989 0.065 Uiso 1 1 calc R U . . .
C14 C 0.7929(2) 0.5899(4) 0.18834(12) 0.0540(5) Uani 1 1 d . . . . .
H14 H 0.796115 0.705563 0.161568 0.065 Uiso 1 1 calc R U . . .
C1 C 0.3097(2) 0.4840(4) 0.46059(11) 0.0515(5) Uani 1 1 d . . . . .
C9 C 0.6087(2) 0.4490(4) 0.30800(11) 0.0496(5) Uani 1 1 d . . . . .
H9 H 0.566211 0.579685 0.302431 0.059 Uiso 1 1 calc R U . . .
C12 C 0.8638(2) 0.2452(4) 0.23015(11) 0.0535(5) Uani 1 1 d . . . . .
H12 H 0.915874 0.126778 0.231901 0.064 Uiso 1 1 calc R U . . .
C3 C 0.4579(2) 0.2406(4) 0.43466(13) 0.0601(6) Uani 1 1 d . . . . .
H3 H 0.499941 0.109814 0.441409 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7094(2) 0.5930(4) 0.22705(11) 0.0530(5) Uani 1 1 d . . . . .
H15 H 0.657770 0.712079 0.225763 0.064 Uiso 1 1 calc R U . . .
C2 C 0.3716(2) 0.2918(5) 0.47057(12) 0.0636(6) Uani 1 1 d . . . . .
H2 H 0.356137 0.196774 0.500955 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4183(2) 0.5727(4) 0.38049(13) 0.0577(6) Uani 1 1 d . . . . .
H5 H 0.432937 0.668507 0.350113 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3329(2) 0.6259(5) 0.41593(12) 0.0591(6) Uani 1 1 d . . . . .
H6 H 0.291079 0.757095 0.409718 0.071 Uiso 1 1 calc R U . . .
C16 C 1.0402(3) 0.2283(5) 0.15181(14) 0.0695(7) Uani 1 1 d . . . . .
H16A H 1.078700 0.205710 0.192252 0.104 Uiso 1 1 calc R U . . .
H16B H 1.098752 0.261833 0.126253 0.104 Uiso 1 1 calc R U . . .
H16C H 0.998098 0.097408 0.137642 0.104 Uiso 1 1 calc R U . . .
C8 C 0.6295(3) 0.1085(4) 0.36409(15) 0.0629(7) Uani 1 1 d . . . . .
C17 C 0.9639(3) 0.5741(5) 0.10568(16) 0.0717(8) Uani 1 1 d . . . . .
H17A H 0.887027 0.591920 0.082188 0.108 Uiso 1 1 calc R U . . .
H17B H 1.020353 0.530378 0.079903 0.108 Uiso 1 1 calc R U . . .
H17C H 0.988552 0.710564 0.124896 0.108 Uiso 1 1 calc R U . . .
N1 N 0.6699(4) -0.0606(4) 0.3759(2) 0.0986(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.096(2) . ?
N2 C13 1.361(3) . ?
N2 C16 1.441(4) . ?
N2 C17 1.439(3) . ?
C13 C14 1.407(3) . ?
C13 C12 1.408(3) . ?
C10 C11 1.397(3) . ?
C10 C9 1.452(3) . ?
C10 C15 1.406(3) . ?
C7 C4 1.485(3) . ?
C7 C9 1.342(3) . ?
C7 C8 1.438(3) . ?
C4 C3 1.385(3) . ?
C4 C5 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(4) . ?
C1 C2 1.367(4) . ?
C1 C6 1.377(4) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.390(4) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 N1 1.143(4) . ?
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
C13 N2 C16 121.6(2) . . ?
C13 N2 C17 121.7(2) . . ?
C17 N2 C16 116.6(2) . . ?
N2 C13 C14 122.3(2) . . ?
N2 C13 C12 121.3(2) . . ?
C14 C13 C12 116.4(2) . . ?
C11 C10 C9 126.8(2) . . ?
C11 C10 C15 115.8(2) . . ?
C15 C10 C9 117.4(2) . . ?
C9 C7 C4 124.4(2) . . ?
C9 C7 C8 121.0(2) . . ?
C8 C7 C4 114.5(2) . . ?
C3 C4 C7 120.9(2) . . ?
C3 C4 C5 117.2(2) . . ?
C5 C4 C7 121.9(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 H11 118.9 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C2 C1 I1 119.84(19) . . ?
C2 C1 C6 120.6(2) . . ?
C6 C1 I1 119.51(19) . . ?
C10 C9 H9 113.9 . . ?
C7 C9 C10 132.2(2) . . ?
C7 C9 H9 113.9 . . ?
C13 C12 H12 119.2 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C4 C3 H3 119.0 . . ?
C4 C3 C2 121.9(2) . . ?
C2 C3 H3 119.0 . . ?
C10 C15 H15 118.6 . . ?
C14 C15 C10 122.7(2) . . ?
C14 C15 H15 118.6 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C8 C7 177.6(3) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 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 C1 C2 C3 178.2(2) . . . . ?
I1 C1 C6 C5 -177.9(2) . . . . ?
N2 C13 C14 C15 -179.8(2) . . . . ?
N2 C13 C12 C11 -179.8(3) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C7 C4 C3 C2 -179.5(2) . . . . ?
C7 C4 C5 C6 179.8(2) . . . . ?
C4 C7 C9 C10 177.2(2) . . . . ?
C4 C3 C2 C1 0.1(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C11 C10 C9 C7 -3.0(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C14 C13 C12 C11 0.4(4) . . . . ?
C9 C10 C11 C12 -177.9(3) . . . . ?
C9 C10 C15 C14 178.5(2) . . . . ?
C9 C7 C4 C3 -176.7(2) . . . . ?
C9 C7 C4 C5 3.9(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C15 C10 C11 C12 0.1(4) . . . . ?
C15 C10 C9 C7 179.0(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C16 N2 C13 C14 179.5(3) . . . . ?
C16 N2 C13 C12 -0.2(4) . . . . ?
C8 C7 C4 C3 2.4(3) . . . . ?
C8 C7 C4 C5 -177.0(2) . . . . ?
C8 C7 C9 C10 -1.9(4) . . . . ?
C17 N2 C13 C14 -3.9(4) . . . . ?
C17 N2 C13 C12 176.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SKG_PALJ_N_I_2020_0m_b
_database_code_depnum_ccdc_archive 'CCDC 2023509'
loop_
_audit_author_name
_audit_author_address
'Althaf Shaik'
;Indian Institute of Technology Gandhinagar
India
;
_audit_update_record             
;
2020-08-16 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 I N2,C16 H15 N3,C2 H4 Cl2'
_chemical_formula_sum            'C35 H34 Cl2 I N5'
_chemical_formula_weight         722.47

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'
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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   11.820(3)
_cell_length_b                   6.1320(14)
_cell_length_c                   22.010(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.353(4)
_cell_angle_gamma                90
_cell_volume                     1545.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.99

_exptl_crystal_description       rods
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            16255
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.915
_diffrn_reflns_theta_max         28.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7699
_reflns_number_gt                7607
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.992

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] 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_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7699
_refine_ls_number_parameters     392
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.2175
_refine_ls_wR_factor_gt          0.2167
_refine_ls_goodness_of_fit_ref   1.731
_refine_ls_restrained_S_all      1.731
_refine_ls_shift/su_max          0.004
_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
C015 C 0.3035(7) 0.1379(18) 0.4321(3) 0.0196(17) Uani 1 1 d . . . . .
N1A N 0.6969(7) 0.3759(16) 0.5686(4) 0.0227(16) Uani 1 1 d . . . . .
C1A C 0.7444(8) 0.5682(18) 0.5650(4) 0.0233(17) Uani 1 1 d . . . . .
H1A H 0.699053 0.673039 0.537662 0.028 Uiso 1 1 calc R U . . .
N2A N 1.0948(6) 0.9285(14) 0.6524(4) 0.0245(15) Uani 1 1 d . . . . .
C1S C 0.9418(12) 1.2630(19) 0.4813(7) 0.030(3) Uani 1 1 d . . . . .
H1SA H 0.941790 1.325567 0.439798 0.036 Uiso 1 1 calc R U . . .
H1SB H 0.896627 1.361526 0.502053 0.036 Uiso 1 1 calc R U . . .
Cl1S Cl 0.8756(2) 0.9994(5) 0.47138(12) 0.0335(6) Uani 1 1 d . . . . .
I1B I 0.46556(5) 0.22612(8) 0.48698(4) 0.0235(2) Uani 1 1 d . . . . .
C1B C 0.2587(7) -0.0683(16) 0.4375(4) 0.0181(15) Uani 1 1 d . . . . .
H1B H 0.303910 -0.172164 0.465245 0.022 Uiso 1 1 calc R U . . .
N1B N -0.0949(6) -0.4245(14) 0.3476(4) 0.0240(15) Uani 1 1 d . . . . .
C2A C 0.8529(8) 0.6276(17) 0.5971(4) 0.0208(16) Uani 1 1 d . . . . .
H2A H 0.882693 0.767897 0.591320 0.025 Uiso 1 1 calc R U . . .
N3A N 1.5757(6) 0.4595(13) 0.8529(3) 0.0172(13) Uani 1 1 d . . . . .
C3A C 0.9199(6) 0.4803(13) 0.6388(3) 0.0124(13) Uani 1 1 d . . . . .
C2S C 1.0619(14) 1.2444(18) 0.5195(7) 0.029(3) Uani 1 1 d . . . . .
H2SA H 1.107340 1.146359 0.498768 0.035 Uiso 1 1 calc R U . . .
H2SB H 1.062136 1.182155 0.561066 0.035 Uiso 1 1 calc R U . . .
Cl2S Cl 1.1246(2) 1.5024(5) 0.52860(12) 0.0327(5) Uani 1 1 d . . . . .
N2B N -0.5727(6) 0.0411(14) 0.1484(3) 0.0194(14) Uani 1 1 d . . . . .
C2B C 0.1494(7) -0.1220(14) 0.4030(4) 0.0169(14) Uani 1 1 d . . . . .
H2B H 0.119844 -0.263612 0.407399 0.020 Uiso 1 1 calc R U . . .
C4A C 0.8719(10) 0.2820(15) 0.6440(6) 0.022(2) Uani 1 1 d . . . . .
H4A H 0.915451 0.175741 0.671569 0.026 Uiso 1 1 calc R U . . .
C3B C 0.0814(7) 0.0214(14) 0.3622(4) 0.0155(14) Uani 1 1 d . . . . .
C5A C 0.7609(15) 0.2340(18) 0.6097(8) 0.027(3) Uani 1 1 d . . . . .
H5A H 0.728349 0.095879 0.615096 0.032 Uiso 1 1 calc R U . . .
C4B C 0.1320(13) 0.2262(16) 0.3571(7) 0.020(3) Uani 1 1 d . . . . .
H4B H 0.089791 0.327886 0.327483 0.025 Uiso 1 1 calc R U . . .
C6A C 1.0376(7) 0.5403(14) 0.6745(4) 0.0144(14) Uani 1 1 d . . . . .
C5B C 0.2400(9) 0.2850(16) 0.3933(5) 0.0188(19) Uani 1 1 d . . . . .
H5B H 0.269082 0.428314 0.390866 0.023 Uiso 1 1 calc R U . . .
C7A C 1.1120(7) 0.4050(15) 0.7150(3) 0.0166(14) Uani 1 1 d . . . . .
H7A H 1.079934 0.267015 0.721034 0.020 Uiso 1 1 calc R U . . .
C6B C -0.0350(7) -0.0409(14) 0.3263(4) 0.0142(14) Uani 1 1 d . . . . .
C8A C 1.2292(7) 0.4366(14) 0.7496(3) 0.0158(14) Uani 1 1 d . . . . .
C7B C -0.1082(7) 0.0934(14) 0.2866(4) 0.0158(14) Uani 1 1 d . . . . .
H7B H -0.075592 0.231589 0.281304 0.019 Uiso 1 1 calc R U . . .
C9A C 1.2963(7) 0.6189(15) 0.7498(4) 0.0181(15) Uani 1 1 d . . . . .
H9A H 1.262886 0.741512 0.725507 0.022 Uiso 1 1 calc R U . . .
C8B C -0.2249(7) 0.0656(13) 0.2515(3) 0.0142(14) Uani 1 1 d . . . . .
C10A C 1.4090(7) 0.6298(15) 0.7835(4) 0.0189(15) Uani 1 1 d . . . . .
H10A H 1.452553 0.759284 0.782323 0.023 Uiso 1 1 calc R U . . .
C9B C -0.2790(11) 0.2399(14) 0.2157(5) 0.0179(19) Uani 1 1 d . . . . .
H9B H -0.234912 0.369144 0.215377 0.021 Uiso 1 1 calc R U . . .
C11A C 1.4621(6) 0.4543(14) 0.8199(3) 0.0136(14) Uani 1 1 d . . . . .
C10B C -0.3903(13) 0.2366(15) 0.1816(6) 0.018(2) Uani 1 1 d . . . . .
H10B H -0.422122 0.361312 0.157854 0.022 Uiso 1 1 calc R U . . .
C12A C 1.3957(11) 0.2675(14) 0.8211(5) 0.019(2) Uani 1 1 d . . . . .
H12A H 1.429223 0.145254 0.845550 0.023 Uiso 1 1 calc R U . . .
C11B C -0.4604(7) 0.0490(15) 0.1807(4) 0.0155(14) Uani 1 1 d . . . . .
C13A C 1.2815(12) 0.2608(15) 0.7869(6) 0.018(2) Uani 1 1 d . . . . .
H13A H 1.236640 0.133341 0.788524 0.021 Uiso 1 1 calc R U . . .
C12B C -0.4081(6) -0.1282(14) 0.2172(3) 0.0151(14) Uani 1 1 d . . . . .
H12B H -0.452406 -0.256525 0.218540 0.018 Uiso 1 1 calc R U . . .
C14A C 1.0736(11) 0.7568(14) 0.6627(6) 0.020(2) Uani 1 1 d . . . . .
C13B C -0.2951(7) -0.1194(14) 0.2507(4) 0.0160(14) Uani 1 1 d . . . . .
H13B H -0.262255 -0.243219 0.274615 0.019 Uiso 1 1 calc R U . . .
C15A C 1.6421(7) 0.6592(17) 0.8586(4) 0.0210(16) Uani 1 1 d . . . . .
H15A H 1.627343 0.731264 0.817670 0.032 Uiso 1 1 calc R U . . .
H15B H 1.725551 0.625896 0.873338 0.032 Uiso 1 1 calc R U . . .
H15C H 1.618623 0.755949 0.888750 0.032 Uiso 1 1 calc R U . . .
C14B C -0.0690(10) -0.2533(14) 0.3381(6) 0.0185(19) Uani 1 1 d . . . . .
C16A C 1.6241(11) 0.2857(16) 0.8936(5) 0.025(2) Uani 1 1 d . . . . .
H16A H 1.616808 0.149470 0.869625 0.037 Uiso 1 1 calc R U . . .
H16B H 1.582201 0.272110 0.926621 0.037 Uiso 1 1 calc R U . . .
H16C H 1.706786 0.315412 0.912552 0.037 Uiso 1 1 calc R U . . .
C16B C -0.6389(8) -0.1588(17) 0.1417(4) 0.0220(16) Uani 1 1 d . . . . .
H16D H -0.720375 -0.128785 0.120092 0.033 Uiso 1 1 calc R U . . .
H16E H -0.635469 -0.219956 0.183261 0.033 Uiso 1 1 calc R U . . .
H16F H -0.605884 -0.263521 0.117183 0.033 Uiso 1 1 calc R U . . .
C15B C -0.6233(12) 0.2169(16) 0.1080(6) 0.026(2) Uani 1 1 d . . . . .
H15D H -0.576353 0.244894 0.077846 0.039 Uiso 1 1 calc R U . . .
H15E H -0.625237 0.348286 0.133064 0.039 Uiso 1 1 calc R U . . .
H15F H -0.703020 0.177847 0.085370 0.039 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
C015 C5B 1.337(13) . ?
C015 C1B 1.387(14) . ?
C015 I1B 2.068(9) . ?
N1A C1A 1.317(14) . ?
N1A C5A 1.344(17) . ?
C1A C2A 1.352(13) . ?
C1A H1A 0.9500 . ?
N2A C14A 1.119(13) . ?
C1S C2S 1.46(2) . ?
C1S Cl1S 1.786(11) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1B C2B 1.366(10) . ?
C1B H1B 0.9500 . ?
N1B C14B 1.128(13) . ?
C2A C3A 1.387(11) . ?
C2A H2A 0.9500 . ?
N3A C11A 1.359(9) . ?
N3A C16A 1.418(12) . ?
N3A C15A 1.443(12) . ?
C3A C4A 1.359(12) . ?
C3A C6A 1.466(10) . ?
C2S Cl2S 1.737(11) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
N2B C11B 1.341(10) . ?
N2B C15B 1.431(13) . ?
N2B C16B 1.442(12) . ?
C2B C3B 1.366(11) . ?
C2B H2B 0.9500 . ?
C4A C5A 1.374(19) . ?
C4A H4A 0.9500 . ?
C3B C4B 1.407(13) . ?
C3B C6B 1.458(11) . ?
C5A H5A 0.9500 . ?
C4B C5B 1.375(17) . ?
C4B H4B 0.9500 . ?
C6A C7A 1.367(11) . ?
C6A C14A 1.437(13) . ?
C5B H5B 0.9500 . ?
C7A C8A 1.418(10) . ?
C7A H7A 0.9500 . ?
C6B C7B 1.347(11) . ?
C6B C14B 1.406(12) . ?
C8A C9A 1.370(12) . ?
C8A C13A 1.402(14) . ?
C7B C8B 1.414(11) . ?
C7B H7B 0.9500 . ?
C9A C10A 1.357(11) . ?
C9A H9A 0.9500 . ?
C8B C9B 1.386(12) . ?
C8B C13B 1.403(11) . ?
C10A C11A 1.394(12) . ?
C10A H10A 0.9500 . ?
C9B C10B 1.343(18) . ?
C9B H9B 0.9500 . ?
C11A C12A 1.393(13) . ?
C10B C11B 1.415(14) . ?
C10B H10B 0.9500 . ?
C12A C13A 1.374(17) . ?
C12A H12A 0.9500 . ?
C11B C12B 1.401(11) . ?
C13A H13A 0.9500 . ?
C12B C13B 1.358(10) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 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
C5B C015 C1B 120.3(8) . . ?
C5B C015 I1B 119.2(8) . . ?
C1B C015 I1B 120.4(6) . . ?
C1A N1A C5A 116.3(9) . . ?
N1A C1A C2A 125.0(9) . . ?
N1A C1A H1A 117.5 . . ?
C2A C1A H1A 117.5 . . ?
C2S C1S Cl1S 109.4(9) . . ?
C2S C1S H1SA 109.8 . . ?
Cl1S C1S H1SA 109.8 . . ?
C2S C1S H1SB 109.8 . . ?
Cl1S C1S H1SB 109.8 . . ?
H1SA C1S H1SB 108.2 . . ?
C2B C1B C015 120.0(8) . . ?
C2B C1B H1B 120.0 . . ?
C015 C1B H1B 120.0 . . ?
C1A C2A C3A 118.8(9) . . ?
C1A C2A H2A 120.6 . . ?
C3A C2A H2A 120.6 . . ?
C11A N3A C16A 120.7(8) . . ?
C11A N3A C15A 120.7(8) . . ?
C16A N3A C15A 117.2(8) . . ?
C4A C3A C2A 117.2(8) . . ?
C4A C3A C6A 122.7(8) . . ?
C2A C3A C6A 120.1(8) . . ?
C1S C2S Cl2S 108.6(9) . . ?
C1S C2S H2SA 110.0 . . ?
Cl2S C2S H2SA 110.0 . . ?
C1S C2S H2SB 110.0 . . ?
Cl2S C2S H2SB 110.0 . . ?
H2SA C2S H2SB 108.3 . . ?
C11B N2B C15B 120.5(9) . . ?
C11B N2B C16B 121.7(8) . . ?
C15B N2B C16B 116.3(8) . . ?
C3B C2B C1B 122.1(8) . . ?
C3B C2B H2B 119.0 . . ?
C1B C2B H2B 119.0 . . ?
C3A C4A C5A 120.5(10) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C2B C3B C4B 115.7(9) . . ?
C2B C3B C6B 120.7(8) . . ?
C4B C3B C6B 123.6(9) . . ?
N1A C5A C4A 122.2(11) . . ?
N1A C5A H5A 118.9 . . ?
C4A C5A H5A 118.9 . . ?
C5B C4B C3B 122.7(11) . . ?
C5B C4B H4B 118.7 . . ?
C3B C4B H4B 118.7 . . ?
C7A C6A C14A 120.5(8) . . ?
C7A C6A C3A 124.7(8) . . ?
C14A C6A C3A 114.8(8) . . ?
C015 C5B C4B 119.1(9) . . ?
C015 C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C6A C7A C8A 130.7(8) . . ?
C6A C7A H7A 114.7 . . ?
C8A C7A H7A 114.7 . . ?
C7B C6B C14B 121.3(8) . . ?
C7B C6B C3B 124.0(8) . . ?
C14B C6B C3B 114.6(8) . . ?
C9A C8A C13A 117.0(8) . . ?
C9A C8A C7A 126.9(8) . . ?
C13A C8A C7A 116.1(9) . . ?
C6B C7B C8B 131.5(8) . . ?
C6B C7B H7B 114.2 . . ?
C8B C7B H7B 114.2 . . ?
C10A C9A C8A 122.1(8) . . ?
C10A C9A H9A 119.0 . . ?
C8A C9A H9A 119.0 . . ?
C9B C8B C13B 115.3(8) . . ?
C9B C8B C7B 117.9(8) . . ?
C13B C8B C7B 126.7(8) . . ?
C9A C10A C11A 121.2(8) . . ?
C9A C10A H10A 119.4 . . ?
C11A C10A H10A 119.4 . . ?
C10B C9B C8B 123.8(9) . . ?
C10B C9B H9B 118.1 . . ?
C8B C9B H9B 118.1 . . ?
N3A C11A C12A 119.7(8) . . ?
N3A C11A C10A 122.2(8) . . ?
C12A C11A C10A 118.0(8) . . ?
C9B C10B C11B 120.6(9) . . ?
C9B C10B H10B 119.7 . . ?
C11B C10B H10B 119.7 . . ?
C13A C12A C11A 119.7(9) . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
N2B C11B C12B 120.9(8) . . ?
N2B C11B C10B 122.5(9) . . ?
C12B C11B C10B 116.6(8) . . ?
C12A C13A C8A 121.9(9) . . ?
C12A C13A H13A 119.0 . . ?
C8A C13A H13A 119.0 . . ?
C13B C12B C11B 121.1(8) . . ?
C13B C12B H12B 119.5 . . ?
C11B C12B H12B 119.5 . . ?
N2A C14A C6A 175.9(13) . . ?
C12B C13B C8B 122.5(8) . . ?
C12B C13B H13B 118.7 . . ?
C8B C13B H13B 118.7 . . ?
N3A C15A H15A 109.5 . . ?
N3A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
N3A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
N1B C14B C6B 179.2(12) . . ?
N3A C16A H16A 109.5 . . ?
N3A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
N3A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N2B C16B H16D 109.5 . . ?
N2B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
N2B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N2B C15B H15D 109.5 . . ?
N2B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
N2B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 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
C5A N1A C1A C2A 2.8(15) . . . . ?
C5B C015 C1B C2B 0.3(13) . . . . ?
I1B C015 C1B C2B 177.2(6) . . . . ?
N1A C1A C2A C3A -1.9(14) . . . . ?
C1A C2A C3A C4A 0.8(13) . . . . ?
C1A C2A C3A C6A -179.8(7) . . . . ?
Cl1S C1S C2S Cl2S -180.0(7) . . . . ?
C015 C1B C2B C3B 0.4(13) . . . . ?
C2A C3A C4A C5A -0.9(17) . . . . ?
C6A C3A C4A C5A 179.7(11) . . . . ?
C1B C2B C3B C4B 1.3(13) . . . . ?
C1B C2B C3B C6B -179.7(7) . . . . ?
C1A N1A C5A C4A -3(2) . . . . ?
C3A C4A C5A N1A 2(2) . . . . ?
C2B C3B C4B C5B -3.9(17) . . . . ?
C6B C3B C4B C5B 177.2(11) . . . . ?
C4A C3A C6A C7A 1.7(13) . . . . ?
C2A C3A C6A C7A -177.7(7) . . . . ?
C4A C3A C6A C14A 179.8(10) . . . . ?
C2A C3A C6A C14A 0.4(11) . . . . ?
C1B C015 C5B C4B -2.7(16) . . . . ?
I1B C015 C5B C4B -179.7(9) . . . . ?
C3B C4B C5B C015 5(2) . . . . ?
C14A C6A C7A C8A -2.0(14) . . . . ?
C3A C6A C7A C8A 176.0(8) . . . . ?
C2B C3B C6B C7B 178.1(7) . . . . ?
C4B C3B C6B C7B -3.0(13) . . . . ?
C2B C3B C6B C14B 0.8(11) . . . . ?
C4B C3B C6B C14B 179.7(10) . . . . ?
C6A C7A C8A C9A 0.0(14) . . . . ?
C6A C7A C8A C13A -179.3(9) . . . . ?
C14B C6B C7B C8B 1.6(14) . . . . ?
C3B C6B C7B C8B -175.5(8) . . . . ?
C13A C8A C9A C10A 1.1(13) . . . . ?
C7A C8A C9A C10A -178.3(8) . . . . ?
C6B C7B C8B C9B 177.9(9) . . . . ?
C6B C7B C8B C13B 0.8(14) . . . . ?
C8A C9A C10A C11A 0.0(12) . . . . ?
C13B C8B C9B C10B -0.8(15) . . . . ?
C7B C8B C9B C10B -178.2(10) . . . . ?
C16A N3A C11A C12A -6.4(12) . . . . ?
C15A N3A C11A C12A -172.4(8) . . . . ?
C16A N3A C11A C10A 174.6(9) . . . . ?
C15A N3A C11A C10A 8.7(11) . . . . ?
C9A C10A C11A N3A 178.4(7) . . . . ?
C9A C10A C11A C12A -0.6(12) . . . . ?
C8B C9B C10B C11B 0.4(19) . . . . ?
N3A C11A C12A C13A -178.8(10) . . . . ?
C10A C11A C12A C13A 0.2(15) . . . . ?
C15B N2B C11B C12B -175.9(8) . . . . ?
C16B N2B C11B C12B -10.0(12) . . . . ?
C15B N2B C11B C10B 6.5(13) . . . . ?
C16B N2B C11B C10B 172.3(9) . . . . ?
C9B C10B C11B N2B 178.3(10) . . . . ?
C9B C10B C11B C12B 0.6(16) . . . . ?
C11A C12A C13A C8A 0.9(18) . . . . ?
C9A C8A C13A C12A -1.5(16) . . . . ?
C7A C8A C13A C12A 177.9(10) . . . . ?
N2B C11B C12B C13B -178.9(8) . . . . ?
C10B C11B C12B C13B -1.1(13) . . . . ?
C11B C12B C13B C8B 0.7(12) . . . . ?
C9B C8B C13B C12B 0.3(12) . . . . ?
C7B C8B C13B C12B 177.4(8) . . . . ?

_refine_diff_density_max         11.663
_refine_diff_density_min         -1.489
_refine_diff_density_rms         0.295



####################################################################### 
# 
# 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_diiodo_0m
_database_code_depnum_ccdc_archive 'CCDC 2213397'
loop_
_audit_author_name
_audit_author_address
'Gurudutt Dubey'
;IIT Gandhinagar
India
;
_audit_update_record             
;
2022-12-12 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2022-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        'Diiodo cyanostilbene'
_chemical_formula_moiety         'C15 H9 I2 N'
_chemical_formula_sum            'C15 H9 I2 N'
_chemical_formula_weight         457.03
_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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   26.328(2)
_cell_length_b                   26.825(3)
_cell_length_c                   8.2403(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.478(2)
_cell_angle_gamma                90
_cell_volume                     5808.9(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9157
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.735
_shelx_estimated_absorpt_T_min   0.164
_exptl_absorpt_coefficient_mu    4.313
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1032 before and 0.0872 after correction.
The Ratio of minimum to maximum transmission is 0.7354.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'clear dark colourless'
_exptl_crystal_F_000             3392
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            149562
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         1.726
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                78996
_reflns_number_total             149562
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.273
_refine_diff_density_min         -1.782
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.00062(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         149562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.0869
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+47.6883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2379
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.904(2)
 0.096(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Others
 Fixed Sof: C53(0.65) C52(0.65) H52(0.65) C61(0.35) C62(0.35) H62(0.35)
4.a Aromatic/amide H refined with riding coordinates:
 C42(H42), C47(H47), C20(H20), C41(H41), C36(H36), C21(H21), C57(H57),
 C14(H14), C44(H44), C35(H35), C6(H6), C56(H56), C45(H45), C39(H39), C24(H24),
 C18(H18), C17(H17), C2(H2), C33(H33), C5(H5), C29(H29), C15(H15), C59(H59),
 C32(H32), C27(H27), C60(H60), C48(H48), C50(H50), C30(H30), C12(H12), C51(H51),
  C26(H26), C11(H11), C7(H7), C3(H3), C52(H52), C62(H62)
;
_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
I6 I 0.73478(4) 0.66693(4) -0.22213(12) 0.0726(3) Uani 1 1 d . . . . .
I7 I 0.76390(4) 0.66941(4) 0.28607(12) 0.0750(3) Uani 1 1 d . . . . .
I3 I 0.81110(4) 0.36854(4) 0.22425(13) 0.0838(4) Uani 1 1 d . . . . .
I2 I 0.68600(4) 0.36657(5) -0.11569(13) 0.0911(4) Uani 1 1 d . . . . .
I5 I 0.31134(4) 0.67786(5) 0.60431(14) 0.1009(5) Uani 1 1 d . . . . .
I8 I 1.19100(4) 0.68839(5) 1.27813(14) 0.0996(4) Uani 1 1 d . . . . .
I4 I 1.22849(5) 0.49180(5) 1.17966(15) 0.0998(4) Uani 1 1 d . . . . .
I1 I 0.26935(5) 0.48866(5) 0.67830(16) 0.1030(4) Uani 1 1 d . . . . .
C43 C 0.6774(5) 0.6716(5) -0.0567(14) 0.051(3) Uani 1 1 d . . . . .
C46 C 0.8222(5) 0.6766(5) 0.4674(15) 0.057(3) Uani 1 1 d . . . . .
C28 C 1.1648(5) 0.4752(5) 1.0283(16) 0.061(3) Uani 1 1 d . . . . .
N3 N 0.5448(4) 0.8055(4) 0.2530(16) 0.071(3) Uani 1 1 d . . . . .
C34 C 0.4748(5) 0.7024(5) 0.3755(14) 0.051(3) Uani 1 1 d . . . . .
N2 N 0.9712(5) 0.5464(4) 0.7991(16) 0.081(4) Uani 1 1 d . . . . .
C42 C 0.6645(5) 0.7179(5) 0.0014(17) 0.059(3) Uani 1 1 d . . . . .
H42 H 0.681518 0.746411 -0.029349 0.071 Uiso 1 1 calc R U . . .
C54 C 0.9635(5) 0.7664(5) 0.8300(16) 0.056(3) Uani 1 1 d . . . . .
C16 C 0.8699(5) 0.3963(5) 0.3776(16) 0.062(4) Uani 1 1 d . . . . .
N4 N 0.9588(5) 0.8079(4) 0.8214(16) 0.078(4) Uani 1 1 d . . . . .
C19 C 0.9496(5) 0.4378(5) 0.5731(16) 0.059(3) Uani 1 1 d . . . . .
C47 C 0.8365(5) 0.7219(6) 0.5232(17) 0.067(4) Uani 1 1 d . . . . .
H47 H 0.819089 0.749926 0.483762 0.080 Uiso 1 1 calc R U . . .
C20 C 0.9573(5) 0.3958(5) 0.4778(16) 0.060(3) Uani 1 1 d . . . . .
H20 H 0.989232 0.380894 0.480720 0.072 Uiso 1 1 calc R U . . .
C31 C 0.3820(5) 0.6902(6) 0.5081(16) 0.061(4) Uani 1 1 d . . . . .
C23 C 0.9813(5) 0.5090(5) 0.7488(16) 0.060(3) Uani 1 1 d . . . . .
C13 C 0.6217(5) 0.3967(5) -0.0141(15) 0.064(4) Uani 1 1 d . . . . .
C38 C 0.5384(5) 0.7643(4) 0.2650(15) 0.050(3) Uani 1 1 d . . . . .
C41 C 0.6260(5) 0.7206(5) 0.1056(16) 0.060(3) Uani 1 1 d . . . . .
H41 H 0.618089 0.751356 0.150084 0.072 Uiso 1 1 calc R U . . .
C37 C 0.5250(6) 0.7119(5) 0.2923(16) 0.066(4) Uani 1 1 d . . . . .
C36 C 0.4184(6) 0.6525(5) 0.5209(16) 0.065(4) Uani 1 1 d . . . . .
H36 H 0.411736 0.622994 0.574955 0.078 Uiso 1 1 calc R U . . .
C21 C 0.9178(5) 0.3759(4) 0.3788(16) 0.057(3) Uani 1 1 d . . . . .
H21 H 0.923849 0.348644 0.312938 0.068 Uiso 1 1 calc R U . . .
C22 C 0.9919(6) 0.4597(5) 0.6819(16) 0.063(4) Uani 1 1 d . . . . .
C57 C 1.1063(5) 0.7368(5) 1.0722(18) 0.067(4) Uani 1 1 d . . . . .
H57 H 1.127902 0.764209 1.079562 0.080 Uiso 1 1 calc R U . . .
C14 C 0.5776(5) 0.3700(5) -0.0137(15) 0.061(3) Uani 1 1 d . . . . .
H14 H 0.575366 0.338833 -0.062808 0.073 Uiso 1 1 calc R U . . .
C58 C 1.1210(5) 0.6933(5) 1.1452(15) 0.057(3) Uani 1 1 d . . . . .
C49 C 0.9034(5) 0.6850(8) 0.6949(17) 0.084(5) Uani 1 1 d . . . . .
C44 C 0.6532(5) 0.6294(5) -0.0127(17) 0.066(4) Uani 1 1 d . . . . .
H44 H 0.663026 0.598396 -0.050606 0.079 Uiso 1 1 calc R U . . .
C40 C 0.5980(5) 0.6783(6) 0.1472(15) 0.062(4) Uani 1 1 d . . . . .
C1 C 0.3293(5) 0.4741(6) 0.5306(18) 0.070(4) Uani 1 1 d . . . . .
C35 C 0.4640(5) 0.6591(5) 0.4535(16) 0.063(4) Uani 1 1 d . . . . .
H35 H 0.488091 0.633760 0.460901 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3468(6) 0.4259(6) 0.5143(18) 0.073(4) Uani 1 1 d . . . . .
H6 H 0.331058 0.399646 0.564868 0.088 Uiso 1 1 calc R U . . .
C56 C 1.0600(5) 0.7408(5) 0.9880(18) 0.066(4) Uani 1 1 d . . . . .
H56 H 1.049685 0.771460 0.944928 0.079 Uiso 1 1 calc R U . . .
N1 N 0.5127(5) 0.5536(4) 0.2915(16) 0.081(4) Uani 1 1 d . . . . .
C25 C 1.0795(5) 0.4528(5) 0.8235(16) 0.063(4) Uani 1 1 d . . . . .
C55 C 1.0285(5) 0.7002(6) 0.9662(15) 0.065(4) Uani 1 1 d . . . . .
C45 C 0.6139(6) 0.6334(5) 0.0890(17) 0.069(4) Uani 1 1 d . . . . .
H45 H 0.597447 0.604490 0.119623 0.082 Uiso 1 1 calc R U . . .
C39 C 0.5523(6) 0.6769(6) 0.2446(18) 0.074(4) Uani 1 1 d . . . . .
H39 H 0.542325 0.645194 0.275149 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5393(6) 0.4363(6) 0.1335(16) 0.067(4) Uani 1 1 d . . . . .
C24 C 1.0342(6) 0.4362(5) 0.7198(17) 0.067(4) Uani 1 1 d . . . . .
H24 H 1.036595 0.404444 0.675815 0.081 Uiso 1 1 calc R U . . .
C18 C 0.9013(6) 0.4577(5) 0.5687(18) 0.073(4) Uani 1 1 d . . . . .
H18 H 0.895371 0.485771 0.630933 0.088 Uiso 1 1 calc R U . . .
C17 C 0.8618(6) 0.4375(6) 0.4756(19) 0.079(4) Uani 1 1 d . . . . .
H17 H 0.829392 0.451203 0.477828 0.095 Uiso 1 1 calc R U . . .
C2 C 0.3542(7) 0.5137(6) 0.455(2) 0.085(5) Uani 1 1 d . . . . .
H2 H 0.342975 0.546363 0.464658 0.102 Uiso 1 1 calc R U . . .
C33 C 0.4387(5) 0.7390(5) 0.3654(17) 0.063(4) Uani 1 1 d . . . . .
H33 H 0.445693 0.768675 0.312982 0.076 Uiso 1 1 calc R U . . .
C5 C 0.3871(6) 0.4175(6) 0.424(2) 0.081(4) Uani 1 1 d . . . . .
H5 H 0.398101 0.384750 0.412849 0.097 Uiso 1 1 calc R U . . .
C29 C 1.1543(6) 0.4274(6) 0.9818(19) 0.079(4) Uani 1 1 d . . . . .
H29 H 1.176019 0.401786 1.017796 0.094 Uiso 1 1 calc R U . . .
C15 C 0.5366(5) 0.3896(6) 0.0596(17) 0.070(4) Uani 1 1 d . . . . .
H15 H 0.506567 0.371314 0.059889 0.084 Uiso 1 1 calc R U . . .
C59 C 1.0897(7) 0.6517(6) 1.1297(18) 0.077(4) Uani 1 1 d . . . . .
H59 H 1.099321 0.621577 1.177928 0.093 Uiso 1 1 calc R U . . .
C32 C 0.3924(5) 0.7330(5) 0.4306(17) 0.062(4) Uani 1 1 d . . . . .
H32 H 0.368290 0.758312 0.421589 0.075 Uiso 1 1 calc R U . . .
C27 C 1.1324(7) 0.5116(6) 0.966(2) 0.080(4) Uani 1 1 d . . . . .
H27 H 1.139833 0.544609 0.992839 0.096 Uiso 1 1 calc R U . . .
C9 C 0.5025(6) 0.5139(5) 0.2653(16) 0.069(4) Uani 1 1 d . . . . .
C60 C 1.0436(7) 0.6565(7) 1.040(2) 0.084(5) Uani 1 1 d . . . . .
H60 H 1.022131 0.629013 1.030475 0.101 Uiso 1 1 calc R U . . .
C4 C 0.4124(6) 0.4540(7) 0.3487(18) 0.074(4) Uani 1 1 d . . . . .
C48 C 0.8766(6) 0.7276(7) 0.6378(18) 0.080(5) Uani 1 1 d . . . . .
H48 H 0.885728 0.759070 0.676679 0.096 Uiso 1 1 calc R U . . .
C50 C 0.8873(7) 0.6391(8) 0.638(2) 0.091(5) Uani 1 1 d . . . . .
H50 H 0.903921 0.610779 0.678876 0.109 Uiso 1 1 calc R U . . .
C30 C 1.1118(6) 0.4166(5) 0.8816(19) 0.075(4) Uani 1 1 d . . . . .
H30 H 1.105037 0.383648 0.853195 0.090 Uiso 1 1 calc R U . . .
C8 C 0.4965(8) 0.4604(6) 0.219(2) 0.091(6) Uani 1 1 d . . . . .
C12 C 0.6250(6) 0.4427(6) 0.054(2) 0.089(5) Uani 1 1 d . . . . .
H12 H 0.655129 0.460749 0.052620 0.107 Uiso 1 1 calc R U . . .
C51 C 0.8474(6) 0.6336(6) 0.524(2) 0.081(4) Uani 1 1 d . . . . .
H51 H 0.837507 0.602220 0.486239 0.097 Uiso 1 1 calc R U . . .
C26 C 1.0906(6) 0.5020(6) 0.870(2) 0.079(4) Uani 1 1 d . . . . .
H26 H 1.069150 0.527888 0.834131 0.095 Uiso 1 1 calc R U . . .
C11 C 0.5847(7) 0.4622(6) 0.123(2) 0.090(5) Uani 1 1 d . . . . .
H11 H 0.587236 0.494213 0.166434 0.108 Uiso 1 1 calc R U . . .
C7 C 0.4587(7) 0.4352(6) 0.2565(19) 0.082(5) Uani 1 1 d . . . . .
H7 H 0.458279 0.401824 0.225983 0.098 Uiso 1 1 calc R U . . .
C3 C 0.3964(7) 0.5025(7) 0.364(2) 0.090(5) Uani 1 1 d . . . . .
H3 H 0.413523 0.528090 0.313711 0.108 Uiso 1 1 calc R U . . .
C53 C 0.9790(12) 0.7141(11) 0.867(3) 0.053(6) Uani 0.65 1 d . . P A 1
C52 C 0.9491(10) 0.6768(9) 0.802(3) 0.052(5) Uani 0.65 1 d . . P A 1
H52 H 0.958244 0.644093 0.828032 0.062 Uiso 0.65 1 calc R U P A 1
C61 C 0.9484(18) 0.7141(16) 0.800(5) 0.039(8) Uani 0.35 1 d . . P A 2
C62 C 0.9826(17) 0.682(2) 0.873(5) 0.045(9) Uani 0.35 1 d . . P A 2
H62 H 0.976940 0.647696 0.864793 0.054 Uiso 0.35 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I6 C43 2.098(12) . ?
I7 C46 2.085(13) . ?
I3 C16 2.076(14) . ?
I2 C13 2.097(14) . ?
I5 C31 2.092(12) . ?
I8 C58 2.089(14) . ?
I4 C28 2.076(14) . ?
I1 C1 2.088(15) . ?
C43 C42 1.380(17) . ?
C43 C44 1.360(17) . ?
C46 C47 1.344(18) . ?
C46 C51 1.398(18) . ?
C28 C29 1.361(18) . ?
C28 C27 1.37(2) . ?
N3 C38 1.123(14) . ?
C34 C37 1.547(19) . ?
C34 C35 1.364(18) . ?
C34 C33 1.366(17) . ?
N2 C23 1.124(15) . ?
C42 H42 0.9300 . ?
C42 C41 1.371(18) . ?
C54 N4 1.121(15) . ?
C54 C53 1.49(4) . ?
C54 C61 1.48(5) . ?
C16 C21 1.374(18) . ?
C16 C17 1.393(19) . ?
C19 C20 1.396(18) . ?
C19 C22 1.505(19) . ?
C19 C18 1.379(18) . ?
C47 H47 0.9300 . ?
C47 C48 1.38(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(18) . ?
C31 C36 1.394(19) . ?
C31 C32 1.350(18) . ?
C23 C22 1.466(19) . ?
C13 C14 1.363(18) . ?
C13 C12 1.356(19) . ?
C38 C37 1.469(19) . ?
C41 H41 0.9300 . ?
C41 C40 1.407(18) . ?
C37 C39 1.260(19) . ?
C36 H36 0.9300 . ?
C36 C35 1.363(18) . ?
C21 H21 0.9300 . ?
C22 C24 1.302(19) . ?
C57 H57 0.9300 . ?
C57 C58 1.358(18) . ?
C57 C56 1.370(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(18) . ?
C58 C59 1.39(2) . ?
C49 C48 1.41(2) . ?
C49 C50 1.37(2) . ?
C49 C52 1.47(3) . ?
C49 C61 1.63(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.375(18) . ?
C40 C45 1.372(19) . ?
C40 C39 1.49(2) . ?
C1 C6 1.381(19) . ?
C1 C2 1.41(2) . ?
C35 H35 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.35(2) . ?
C56 H56 0.9300 . ?
C56 C55 1.375(19) . ?
N1 C9 1.115(15) . ?
C25 C24 1.49(2) . ?
C25 C30 1.358(19) . ?
C25 C26 1.401(19) . ?
C55 C60 1.37(2) . ?
C55 C53 1.54(4) . ?
C55 C62 1.47(5) . ?
C45 H45 0.9300 . ?
C39 H39 0.9300 . ?
C10 C15 1.393(19) . ?
C10 C8 1.51(2) . ?
C10 C11 1.39(2) . ?
C24 H24 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.37(2) . ?
C17 H17 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.41(2) . ?
C33 H33 0.9300 . ?
C33 C32 1.371(18) . ?
C5 H5 0.9300 . ?
C5 C4 1.36(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.38(2) . ?
C15 H15 0.9300 . ?
C59 H59 0.9300 . ?
C59 C60 1.39(2) . ?
C32 H32 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.34(2) . ?
C9 C8 1.49(2) . ?
C60 H60 0.9300 . ?
C4 C7 1.56(2) . ?
C4 C3 1.38(2) . ?
C48 H48 0.9300 . ?
C50 H50 0.9300 . ?
C50 C51 1.37(2) . ?
C30 H30 0.9300 . ?
C8 C7 1.26(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.34(2) . ?
C51 H51 0.9300 . ?
C26 H26 0.9300 . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C53 C52 1.36(3) . ?
C52 H52 0.9300 . ?
C61 C62 1.36(6) . ?
C62 H62 0.9300 . ?

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
C42 C43 I6 118.8(9) . . ?
C44 C43 I6 119.4(10) . . ?
C44 C43 C42 121.8(12) . . ?
C47 C46 I7 120.5(10) . . ?
C47 C46 C51 120.9(14) . . ?
C51 C46 I7 118.5(11) . . ?
C29 C28 I4 120.9(11) . . ?
C29 C28 C27 117.0(14) . . ?
C27 C28 I4 122.1(11) . . ?
C35 C34 C37 123.9(12) . . ?
C35 C34 C33 118.4(12) . . ?
C33 C34 C37 117.6(12) . . ?
C43 C42 H42 120.9 . . ?
C41 C42 C43 118.3(12) . . ?
C41 C42 H42 120.9 . . ?
N4 C54 C53 167.8(19) . . ?
N4 C54 C61 155(2) . . ?
C21 C16 I3 120.8(10) . . ?
C21 C16 C17 119.0(13) . . ?
C17 C16 I3 120.1(11) . . ?
C20 C19 C22 121.6(13) . . ?
C18 C19 C20 117.5(13) . . ?
C18 C19 C22 120.8(13) . . ?
C46 C47 H47 119.3 . . ?
C46 C47 C48 121.4(15) . . ?
C48 C47 H47 119.3 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(12) . . ?
C21 C20 H20 119.6 . . ?
C36 C31 I5 118.7(11) . . ?
C32 C31 I5 121.6(11) . . ?
C32 C31 C36 119.6(12) . . ?
N2 C23 C22 177.2(16) . . ?
C14 C13 I2 120.4(10) . . ?
C12 C13 I2 118.9(12) . . ?
C12 C13 C14 120.7(14) . . ?
N3 C38 C37 173.2(15) . . ?
C42 C41 H41 119.1 . . ?
C42 C41 C40 121.8(12) . . ?
C40 C41 H41 119.1 . . ?
C38 C37 C34 116.5(12) . . ?
C39 C37 C34 122.3(14) . . ?
C39 C37 C38 121.2(15) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 C31 119.5(13) . . ?
C35 C36 H36 120.2 . . ?
C16 C21 C20 120.4(12) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C19 115.2(12) . . ?
C24 C22 C19 123.0(13) . . ?
C24 C22 C23 121.7(15) . . ?
C58 C57 H57 119.6 . . ?
C58 C57 C56 120.9(14) . . ?
C56 C57 H57 119.6 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(13) . . ?
C15 C14 H14 120.3 . . ?
C57 C58 I8 120.4(11) . . ?
C57 C58 C59 119.8(14) . . ?
C59 C58 I8 119.9(11) . . ?
C48 C49 C52 134(2) . . ?
C48 C49 C61 97(2) . . ?
C50 C49 C48 118.3(15) . . ?
C50 C49 C52 107.3(18) . . ?
C50 C49 C61 144(2) . . ?
C43 C44 H44 120.7 . . ?
C43 C44 C45 118.7(13) . . ?
C45 C44 H44 120.7 . . ?
C41 C40 C39 127.2(14) . . ?
C45 C40 C41 116.7(12) . . ?
C45 C40 C39 116.2(13) . . ?
C6 C1 I1 120.0(12) . . ?
C6 C1 C2 119.6(15) . . ?
C2 C1 I1 120.3(12) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.1(13) . . ?
C36 C35 H35 119.4 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.3(15) . . ?
C5 C6 H6 120.4 . . ?
C57 C56 H56 119.5 . . ?
C57 C56 C55 121.0(13) . . ?
C55 C56 H56 119.5 . . ?
C30 C25 C24 116.8(13) . . ?
C30 C25 C26 117.5(14) . . ?
C26 C25 C24 125.7(14) . . ?
C56 C55 C53 111.2(17) . . ?
C56 C55 C62 143(3) . . ?
C60 C55 C56 117.6(14) . . ?
C60 C55 C53 131.1(17) . . ?
C60 C55 C62 99(2) . . ?
C44 C45 H45 118.7 . . ?
C40 C45 C44 122.6(13) . . ?
C40 C45 H45 118.7 . . ?
C37 C39 C40 130.2(15) . . ?
C37 C39 H39 114.9 . . ?
C40 C39 H39 114.9 . . ?
C15 C10 C8 124.8(15) . . ?
C11 C10 C15 116.4(14) . . ?
C11 C10 C8 118.8(14) . . ?
C22 C24 C25 129.5(14) . . ?
C22 C24 H24 115.2 . . ?
C25 C24 H24 115.2 . . ?
C19 C18 H18 118.9 . . ?
C17 C18 C19 122.1(14) . . ?
C17 C18 H18 118.9 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(14) . . ?
C18 C17 H17 120.0 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.5(15) . . ?
C3 C2 H2 120.7 . . ?
C34 C33 H33 119.2 . . ?
C34 C33 C32 121.6(13) . . ?
C32 C33 H33 119.2 . . ?
C6 C5 H5 118.2 . . ?
C6 C5 C4 123.6(16) . . ?
C4 C5 H5 118.2 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.5(15) . . ?
C30 C29 H29 119.7 . . ?
C14 C15 C10 121.0(14) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C58 C59 H59 121.0 . . ?
C60 C59 C58 118.1(14) . . ?
C60 C59 H59 121.0 . . ?
C31 C32 C33 119.8(13) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C27 H27 118.2 . . ?
C26 C27 C28 123.5(15) . . ?
C26 C27 H27 118.2 . . ?
N1 C9 C8 171.2(19) . . ?
C55 C60 C59 122.5(15) . . ?
C55 C60 H60 118.7 . . ?
C59 C60 H60 118.7 . . ?
C5 C4 C7 114.2(15) . . ?
C5 C4 C3 118.8(15) . . ?
C3 C4 C7 127.0(16) . . ?
C47 C48 C49 119.0(16) . . ?
C47 C48 H48 120.5 . . ?
C49 C48 H48 120.5 . . ?
C49 C50 H50 118.8 . . ?
C49 C50 C51 122.5(16) . . ?
C51 C50 H50 118.8 . . ?
C25 C30 C29 122.0(14) . . ?
C25 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
C9 C8 C10 117.5(16) . . ?
C7 C8 C10 120.5(16) . . ?
C7 C8 C9 121.8(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.9(15) . . ?
C11 C12 H12 120.1 . . ?
C46 C51 H51 121.1 . . ?
C50 C51 C46 117.9(16) . . ?
C50 C51 H51 121.1 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.4(15) . . ?
C27 C26 H26 120.3 . . ?
C10 C11 H11 118.8 . . ?
C12 C11 C10 122.4(14) . . ?
C12 C11 H11 118.8 . . ?
C4 C7 H7 116.6 . . ?
C8 C7 C4 126.9(16) . . ?
C8 C7 H7 116.6 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(16) . . ?
C4 C3 H3 119.9 . . ?
C54 C53 C55 123(2) . . ?
C52 C53 C54 118(3) . . ?
C52 C53 C55 119(3) . . ?
C49 C52 H52 118.0 . . ?
C53 C52 C49 124(3) . . ?
C53 C52 H52 118.0 . . ?
C54 C61 C49 137(3) . . ?
C62 C61 C54 111(5) . . ?
C62 C61 C49 112(5) . . ?
C55 C62 H62 119.5 . . ?
C61 C62 C55 121(6) . . ?
C61 C62 H62 119.5 . . ?

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
I6 C43 C42 C41 178.1(10) . . . . ?
I6 C43 C44 C45 -176.6(10) . . . . ?
I7 C46 C47 C48 -177.0(10) . . . . ?
I7 C46 C51 C50 177.1(11) . . . . ?
I3 C16 C21 C20 177.9(9) . . . . ?
I3 C16 C17 C18 -175.8(12) . . . . ?
I2 C13 C14 C15 177.2(10) . . . . ?
I2 C13 C12 C11 -178.3(14) . . . . ?
I5 C31 C36 C35 177.6(10) . . . . ?
I5 C31 C32 C33 -178.2(10) . . . . ?
I8 C58 C59 C60 -179.9(10) . . . . ?
I4 C28 C29 C30 179.7(11) . . . . ?
I4 C28 C27 C26 -179.2(12) . . . . ?
I1 C1 C6 C5 -177.1(11) . . . . ?
I1 C1 C2 C3 176.4(11) . . . . ?
C43 C42 C41 C40 -3(2) . . . . ?
C43 C44 C45 C40 0(2) . . . . ?
C46 C47 C48 C49 1(2) . . . . ?
C28 C29 C30 C25 1(2) . . . . ?
C28 C27 C26 C25 -2(2) . . . . ?
C34 C37 C39 C40 172.3(13) . . . . ?
C34 C33 C32 C31 0(2) . . . . ?
C42 C43 C44 C45 2(2) . . . . ?
C42 C41 C40 C45 5(2) . . . . ?
C42 C41 C40 C39 -173.4(13) . . . . ?
C54 C53 C52 C49 2(3) . . . . ?
C54 C61 C62 C55 -1(4) . . . . ?
N4 C54 C53 C55 -10(8) . . . . ?
N4 C54 C53 C52 174(6) . . . . ?
N4 C54 C61 C49 7(7) . . . . ?
N4 C54 C61 C62 -177(3) . . . . ?
C19 C20 C21 C16 -2(2) . . . . ?
C19 C22 C24 C25 179.3(12) . . . . ?
C19 C18 C17 C16 -2(2) . . . . ?
C47 C46 C51 C50 0(2) . . . . ?
C20 C19 C22 C23 168.2(12) . . . . ?
C20 C19 C22 C24 -14(2) . . . . ?
C20 C19 C18 C17 0(2) . . . . ?
C31 C36 C35 C34 1(2) . . . . ?
C23 C22 C24 C25 -3(2) . . . . ?
C13 C14 C15 C10 0(2) . . . . ?
C13 C12 C11 C10 2(3) . . . . ?
C38 C37 C39 C40 -5(2) . . . . ?
C41 C40 C45 C44 -4(2) . . . . ?
C41 C40 C39 C37 10(2) . . . . ?
C37 C34 C35 C36 -178.3(12) . . . . ?
C37 C34 C33 C32 177.7(12) . . . . ?
C36 C31 C32 C33 0(2) . . . . ?
C21 C16 C17 C18 1(2) . . . . ?
C22 C19 C20 C21 179.7(12) . . . . ?
C22 C19 C18 C17 -177.5(13) . . . . ?
C57 C58 C59 C60 -1(2) . . . . ?
C57 C56 C55 C60 4(2) . . . . ?
C57 C56 C55 C53 -179.5(14) . . . . ?
C57 C56 C55 C62 -167(3) . . . . ?
C14 C13 C12 C11 0(2) . . . . ?
C58 C57 C56 C55 -4(2) . . . . ?
C58 C59 C60 C55 1(2) . . . . ?
C49 C50 C51 C46 -1(2) . . . . ?
C49 C61 C62 C55 176(2) . . . . ?
C44 C43 C42 C41 0(2) . . . . ?
C1 C6 C5 C4 1(2) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C35 C34 C37 C38 -159.4(12) . . . . ?
C35 C34 C37 C39 23(2) . . . . ?
C35 C34 C33 C32 0(2) . . . . ?
C6 C1 C2 C3 0(2) . . . . ?
C6 C5 C4 C7 178.0(14) . . . . ?
C6 C5 C4 C3 0(2) . . . . ?
C56 C57 C58 I8 -178.4(11) . . . . ?
C56 C57 C58 C59 2(2) . . . . ?
C56 C55 C60 C59 -2(2) . . . . ?
C56 C55 C53 C54 -12(2) . . . . ?
C56 C55 C53 C52 165.1(16) . . . . ?
C56 C55 C62 C61 -20(5) . . . . ?
C55 C53 C52 C49 -175.0(15) . . . . ?
C45 C40 C39 C37 -168.3(15) . . . . ?
C39 C40 C45 C44 175.1(13) . . . . ?
C10 C8 C7 C4 178.2(13) . . . . ?
C24 C25 C30 C29 -178.5(14) . . . . ?
C24 C25 C26 C27 178.8(14) . . . . ?
C18 C19 C20 C21 1.9(19) . . . . ?
C18 C19 C22 C23 -14.1(18) . . . . ?
C18 C19 C22 C24 163.5(14) . . . . ?
C17 C16 C21 C20 1(2) . . . . ?
C2 C1 C6 C5 -1(2) . . . . ?
C33 C34 C37 C38 22.7(16) . . . . ?
C33 C34 C37 C39 -154.7(14) . . . . ?
C33 C34 C35 C36 -0.4(19) . . . . ?
C5 C4 C7 C8 -157.3(17) . . . . ?
C5 C4 C3 C2 -1(2) . . . . ?
C29 C28 C27 C26 3(2) . . . . ?
C15 C10 C8 C9 -169.3(13) . . . . ?
C15 C10 C8 C7 14(2) . . . . ?
C15 C10 C11 C12 -3(2) . . . . ?
C32 C31 C36 C35 -1(2) . . . . ?
C27 C28 C29 C30 -2(2) . . . . ?
C9 C8 C7 C4 2(2) . . . . ?
C60 C55 C53 C54 164.1(15) . . . . ?
C60 C55 C53 C52 -19(3) . . . . ?
C60 C55 C62 C61 168(3) . . . . ?
C48 C49 C50 C51 3(2) . . . . ?
C48 C49 C52 C53 -4(3) . . . . ?
C48 C49 C61 C54 -4(4) . . . . ?
C48 C49 C61 C62 -180(3) . . . . ?
C50 C49 C48 C47 -2(2) . . . . ?
C50 C49 C52 C53 172.4(18) . . . . ?
C50 C49 C61 C54 169(2) . . . . ?
C50 C49 C61 C62 -7(5) . . . . ?
C30 C25 C24 C22 161.3(15) . . . . ?
C30 C25 C26 C27 1(2) . . . . ?
C8 C10 C15 C14 -179.1(13) . . . . ?
C8 C10 C11 C12 177.9(16) . . . . ?
C12 C13 C14 C15 -1(2) . . . . ?
C51 C46 C47 C48 0(2) . . . . ?
C26 C25 C24 C22 -17(2) . . . . ?
C26 C25 C30 C29 -1(2) . . . . ?
C11 C10 C15 C14 2(2) . . . . ?
C11 C10 C8 C9 9(2) . . . . ?
C11 C10 C8 C7 -167.1(16) . . . . ?
C7 C4 C3 C2 -178.6(14) . . . . ?
C3 C4 C7 C8 21(3) . . . . ?
C53 C55 C60 C59 -178.0(16) . . . . ?
C52 C49 C48 C47 174.1(16) . . . . ?
C52 C49 C50 C51 -174.8(15) . . . . ?
C61 C49 C48 C47 172.5(17) . . . . ?
C61 C49 C50 C51 -169(3) . . . . ?
C62 C55 C60 C59 172.1(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.904(2)
2 0.096(2)

# start Validation Reply Form
_vrf_PLAT234_diiodo_0m           
;
PROBLEM: Large Hirshfeld Difference C4       --C7       .       0.26 Ang.  
RESPONSE: The alert is generated due to the presence of twinning in the crystal and a large amount of disorder in the crystal structure
;
_vrf_PLAT342_diiodo_0m           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02068 Ang.  
RESPONSE: The alert is generated due to the presence of twinning in the crystal and a large amount of disorder in the crystal structure
;
