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

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1588556'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C8 H3 I N2'
_chemical_formula_sum            'C8 H3 I N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         254.02

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6381(5)
_cell_length_b                   8.0021(5)
_cell_length_c                   8.1572(5)
_cell_angle_alpha                109.201(4)
_cell_angle_beta                 105.966(4)
_cell_angle_gamma                109.054(4)
_cell_volume                     402.13(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2997
_cell_measurement_theta_min      2.9264
_cell_measurement_theta_max      27.3975
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.142
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236

_exptl_absorpt_coefficient_mu    3.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.61

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4550
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             1377
_reflns_number_gt                1296
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0928
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         1377
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.949
_refine_diff_density_min         -1.292
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2363(8) 0.8056(8) 0.6592(7) 0.0258(11) Uani d . . . 1 . .
C C2 0.2415(7) 0.7539(7) 0.4766(7) 0.0203(10) Uani d . . . 1 . .
C C3 0.2559(7) 0.5788(7) 0.3871(6) 0.0213(10) Uani d . . . 1 . .
H H3 0.2583 0.4945 0.4459 0.026 Uiso calc U . R 1 . .
C C4 0.2667(7) 0.5309(7) 0.2113(6) 0.0226(10) Uani d . . . 1 . .
C C5 0.2608(8) 0.6519(8) 0.1228(7) 0.0252(11) Uani d . . . 1 . .
H H5 0.2683 0.6176 0.0027 0.03 Uiso calc U . R 1 . .
C C6 0.2440(7) 0.8217(7) 0.2098(6) 0.0220(10) Uani d . . . 1 . .
H H6 0.2379 0.9029 0.1479 0.026 Uiso calc U . R 1 . .
C C7 0.2360(7) 0.8756(7) 0.3865(6) 0.0197(10) Uani d . . . 1 . .
C C8 0.2230(7) 1.0574(7) 0.4763(6) 0.0225(10) Uani d . . . 1 . .
I I1 0.29089(5) 0.27425(4) 0.07642(4) 0.02887(19) Uani d . . . 1 . .
N N1 0.2364(8) 0.8476(8) 0.8095(6) 0.0363(12) Uani d . . . 1 . .
N N2 0.2141(7) 1.2032(7) 0.5422(6) 0.0326(10) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.159(7) ?
C1 C2 . 1.425(7) ?
C2 C7 . 1.405(7) ?
C2 C3 . 1.407(7) ?
C3 C4 . 1.391(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.389(7) ?
C4 I1 . 2.083(5) ?
C5 C6 . 1.376(7) ?
C5 H5 . 0.95 ?
C6 C7 . 1.387(6) ?
C6 H6 . 0.95 ?
C7 C8 . 1.448(7) ?
C8 N2 . 1.147(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 178.4(5) ?
C7 C2 C3 . . 119.6(4) ?
C7 C2 C1 . . 121.3(4) ?
C3 C2 C1 . . 119.1(4) ?
C4 C3 C2 . . 119.1(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C5 C4 C3 . . 120.9(5) ?
C5 C4 I1 . . 119.1(3) ?
C3 C4 I1 . . 120.0(4) ?
C6 C5 C4 . . 119.8(4) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C7 . . 120.9(5) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C6 C7 C2 . . 119.7(4) ?
C6 C7 C8 . . 119.6(4) ?
C2 C7 C8 . . 120.8(4) ?
N2 C8 C7 . . 177.4(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 0.7(7) ?
C1 C2 C3 C4 . . . . -178.3(4) ?
C2 C3 C4 C5 . . . . -0.8(7) ?
C2 C3 C4 I1 . . . . 179.4(3) ?
C3 C4 C5 C6 . . . . 0.0(7) ?
I1 C4 C5 C6 . . . . 179.8(3) ?
C4 C5 C6 C7 . . . . 1.0(7) ?
C5 C6 C7 C2 . . . . -1.1(7) ?
C5 C6 C7 C8 . . . . 178.6(4) ?
C3 C2 C7 C6 . . . . 0.3(7) ?
C1 C2 C7 C6 . . . . 179.2(4) ?
C3 C2 C7 C8 . . . . -179.5(4) ?
C1 C2 C7 C8 . . . . -0.6(7) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 N2 1_545 0.95 2.65 3.582(7) 168.9 ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1588558'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Phthalonitrile
_chemical_formula_moiety         'C8 H2 I2 N2'
_chemical_formula_sum            'C8 H2 I2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         379.92

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9085(6)
_cell_length_b                   7.7205(5)
_cell_length_c                   9.6719(7)
_cell_angle_alpha                93.192(3)
_cell_angle_beta                 110.609(4)
_cell_angle_gamma                94.050(3)
_cell_volume                     479.86(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      4.3187
_cell_measurement_theta_max      25.9156
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    2.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340

_exptl_absorpt_coefficient_mu    6.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.60

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4147
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             1629
_reflns_number_gt                1490
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.1784
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.152
_refine_ls_number_reflns         1629
_refine_ls_number_parameters     109
_refine_ls_number_restraints     24
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+39.8578P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         3.116
_refine_diff_density_min         -2.003
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.690(4) 0.332(3) 0.106(2) 0.047(5) Uani d U . . 1 . .
C C2 0.593(3) 0.285(2) 0.211(2) 0.024(4) Uani d . . . 1 . .
C C3 0.700(3) 0.334(2) 0.3591(18) 0.019(4) Uani d . . . 1 . .
H H3 0.8348 0.3938 0.39 0.023 Uiso calc U . R 1 . .
C C4 0.610(3) 0.295(2) 0.4645(19) 0.019(3) Uani d . . . 1 . .
C C5 0.411(3) 0.214(2) 0.4194(19) 0.019(3) Uani d . . . 1 . .
C C6 0.300(3) 0.162(2) 0.266(2) 0.025(3) Uani d U . . 1 . .
H H6 0.164 0.1029 0.2342 0.03 Uiso calc U . R 1 . .
C C7 0.393(3) 0.197(2) 0.164(2) 0.024(3) Uani d U . . 1 . .
C C8 0.282(3) 0.136(2) 0.010(2) 0.027(3) Uani d U . . 1 . .
I I1 0.79040(17) 0.35959(15) 0.68769(12) 0.0226(4) Uani d . . . 1 . .
I I2 0.25847(19) 0.16626(15) 0.56705(14) 0.0268(4) Uani d . . . 1 . .
N N1 0.769(3) 0.378(3) 0.026(2) 0.055(5) Uani d U . . 1 . .
N N2 0.198(3) 0.089(2) -0.1147(19) 0.036(4) Uani d U . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.15(3) ?
C1 C2 . 1.46(3) ?
C2 C3 . 1.37(3) ?
C2 C7 . 1.40(2) ?
C3 C4 . 1.40(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.38(2) ?
C4 I1 . 2.087(17) ?
C5 C6 . 1.43(2) ?
C5 I2 . 2.085(17) ?
C6 C7 . 1.38(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.44(2) ?
C8 N2 . 1.17(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 176.(3) ?
C3 C2 C7 . . 120.6(17) ?
C3 C2 C1 . . 118.3(17) ?
C7 C2 C1 . . 121.0(18) ?
C2 C3 C4 . . 120.3(16) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C5 C4 C3 . . 119.9(16) ?
C5 C4 I1 . . 122.2(13) ?
C3 C4 I1 . . 117.8(12) ?
C4 C5 C6 . . 119.9(16) ?
C4 C5 I2 . . 122.6(13) ?
C6 C5 I2 . . 117.5(13) ?
C7 C6 C5 . . 119.2(16) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C2 . . 120.0(16) ?
C6 C7 C8 . . 118.1(16) ?
C2 C7 C8 . . 121.9(18) ?
N2 C8 C7 . . 177.(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 0.(3) ?
C1 C2 C3 C4 . . . . 178.4(19) ?
C2 C3 C4 C5 . . . . -3.(3) ?
C2 C3 C4 I1 . . . . 176.3(13) ?
C3 C4 C5 C6 . . . . 4.(2) ?
I1 C4 C5 C6 . . . . -175.4(12) ?
C3 C4 C5 I2 . . . . -176.0(12) ?
I1 C4 C5 I2 . . . . 5.(2) ?
C4 C5 C6 C7 . . . . -2.(3) ?
I2 C5 C6 C7 . . . . 177.8(13) ?
C5 C6 C7 C2 . . . . -1.(3) ?
C5 C6 C7 C8 . . . . 177.5(16) ?
C3 C2 C7 C6 . . . . 2.(3) ?
C1 C2 C7 C6 . . . . -177.(2) ?
C3 C2 C7 C8 . . . . -176.5(17) ?
C1 C2 C7 C8 . . . . 5.(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 N2 2 0.95 2.66 3.60(2) 170.9 ?

####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1588557'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            phthalonitrile
_chemical_formula_moiety         'C8 H3 I N2'
_chemical_formula_sum            'C8 H3 I N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         254.02

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   7.9954(6)
_cell_length_b                   15.2187(11)
_cell_length_c                   7.5106(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.649(4)
_cell_angle_gamma                90
_cell_volume                     816.81(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    73
_cell_measurement_theta_min      3.3598
_cell_measurement_theta_max      22.0347
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    3.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_T_max  0.77

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5968
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             1438
_reflns_number_gt                1213
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1067
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         1438
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.4192P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.941
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5452(7) 0.3110(3) 0.4846(9) 0.0409(12) Uani d . . . 1 . .
C C2 0.3789(7) 0.2681(3) 0.4677(8) 0.0394(12) Uani d . . . 1 . .
C C3 0.2235(7) 0.3145(4) 0.4478(8) 0.0408(12) Uani d . . . 1 . .
C C4 0.0658(8) 0.2692(4) 0.4323(9) 0.0528(14) Uani d . . . 1 . .
H H4 -0.0388 0.3001 0.4209 0.063 Uiso calc U . R 1 . .
C C5 0.0647(8) 0.1790(4) 0.4336(9) 0.0536(15) Uani d . . . 1 . .
H H5 -0.0418 0.1496 0.4217 0.064 Uiso calc U . R 1 . .
C C6 0.2171(8) 0.1313(4) 0.4523(9) 0.0494(14) Uani d . . . 1 . .
H H6 0.2143 0.0702 0.4539 0.059 Uiso calc U . R 1 . .
C C7 0.3749(8) 0.1748(3) 0.4686(9) 0.0427(12) Uani d . . . 1 . .
C C8 0.5386(9) 0.1277(4) 0.4897(10) 0.0517(14) Uani d . . . 1 . .
I I1 0.22621(6) 0.45148(2) 0.44861(7) 0.0572(2) Uani d . . . 1 . .
N N1 0.6782(8) 0.3430(3) 0.4956(10) 0.0602(14) Uani d . . . 1 . .
N N2 0.6713(8) 0.0933(3) 0.5028(11) 0.0740(17) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.138(7) ?
C1 C2 . 1.435(7) ?
C2 C3 . 1.378(7) ?
C2 C7 . 1.421(7) ?
C3 C4 . 1.395(8) ?
C3 I1 . 2.085(5) ?
C4 C5 . 1.373(8) ?
C4 H4 . 0.93 ?
C5 C6 . 1.370(8) ?
C5 H5 . 0.93 ?
C6 C7 . 1.380(7) ?
C6 H6 . 0.93 ?
C7 C8 . 1.437(8) ?
C8 N2 . 1.148(7) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 178.1(6) ?
C3 C2 C7 . . 119.4(5) ?
C3 C2 C1 . . 122.1(5) ?
C7 C2 C1 . . 118.4(5) ?
C2 C3 C4 . . 119.6(5) ?
C2 C3 I1 . . 120.3(4) ?
C4 C3 I1 . . 120.2(4) ?
C5 C4 C3 . . 120.1(5) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C6 C5 C4 . . 121.5(5) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 119.4(5) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C6 C7 C2 . . 120.0(5) ?
C6 C7 C8 . . 121.5(5) ?
C2 C7 C8 . . 118.5(5) ?
N2 C8 C7 . . 177.0(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 1.1(8) ?
C1 C2 C3 C4 . . . . -179.9(5) ?
C7 C2 C3 I1 . . . . 179.4(4) ?
C1 C2 C3 I1 . . . . -1.6(7) ?
C2 C3 C4 C5 . . . . -1.0(8) ?
I1 C3 C4 C5 . . . . -179.4(4) ?
C3 C4 C5 C6 . . . . 0.7(9) ?
C4 C5 C6 C7 . . . . -0.5(9) ?
C5 C6 C7 C2 . . . . 0.5(9) ?
C5 C6 C7 C8 . . . . 179.6(6) ?
C3 C2 C7 C6 . . . . -0.8(8) ?
C1 C2 C7 C6 . . . . -179.9(5) ?
C3 C2 C7 C8 . . . . -179.9(5) ?
C1 C2 C7 C8 . . . . 1.0(8) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 N1 1_455 0.93 2.65 3.524(8) 157.7 ?

####################################################################### 
# 
# 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_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1588559'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Phthalonitrile
_chemical_formula_moiety         'C8 H2 I2 N2'
_chemical_formula_sum            'C8 H2 I2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         379.92

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   21.305(7)
_cell_length_b                   4.1552(14)
_cell_length_c                   21.526(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.091(9)
_cell_angle_gamma                90
_cell_volume                     1898.1(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    110
_cell_measurement_theta_min      1.9258
_cell_measurement_theta_max      22.1294
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.078
_exptl_crystal_density_diffrn    2.659
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360

_exptl_absorpt_coefficient_mu    6.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_T_max  0.63

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8570
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             3260
_reflns_number_gt                2214
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1788
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.976
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     217
_refine_ls_number_restraints     84
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0873P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.201
_refine_diff_density_min         -3.710
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3730(6) 0.665(4) 0.2077(7) 0.026(4) Uani d . . . 1 . .
C C2 0.4187(5) 0.604(3) 0.2592(6) 0.020(2) Uani d U . . 1 . .
C C3 0.4019(5) 0.459(3) 0.3129(6) 0.018(2) Uani d U . . 1 . .
C C4 0.4468(5) 0.408(3) 0.3623(6) 0.021(2) Uani d U . . 1 . .
C C5 0.5102(5) 0.501(4) 0.3571(6) 0.025(2) Uani d U . . 1 . .
H H5 0.5413 0.4647 0.3907 0.03 Uiso calc U . R 1 . .
C C6 0.5263(6) 0.642(3) 0.3029(6) 0.024(2) Uani d U . . 1 . .
H H6 0.5688 0.7048 0.2996 0.029 Uiso calc U . R 1 . .
C C7 0.4815(6) 0.696(3) 0.2528(6) 0.022(2) Uani d U . . 1 . .
C C8 0.4985(6) 0.862(4) 0.1980(7) 0.030(4) Uani d . . . 1 . .
C C9 0.3198(6) 0.991(3) 0.5798(5) 0.020(3) Uani d . . . 1 . .
C C10 0.2516(5) 1.013(3) 0.5825(6) 0.019(2) Uani d U . . 1 . .
C C11 0.2122(6) 0.881(3) 0.5348(6) 0.018(2) Uani d U . . 1 . .
C C12 0.1458(5) 0.923(3) 0.5389(6) 0.019(2) Uani d U . . 1 . .
C C13 0.1233(6) 1.069(3) 0.5912(6) 0.021(2) Uani d U . . 1 . .
H H13 0.0792 1.0848 0.5944 0.025 Uiso calc U . R 1 . .
C C14 0.1641(6) 1.189(3) 0.6372(6) 0.022(2) Uani d U . . 1 . .
H H14 0.1482 1.2919 0.6719 0.026 Uiso calc U . R 1 . .
C C15 0.2294(6) 1.162(3) 0.6343(6) 0.0214(19) Uani d U . . 1 . .
C C16 0.2733(7) 1.290(4) 0.6812(7) 0.028(2) Uani d U . . 1 . .
I I1 0.30805(4) 0.3214(2) 0.31817(4) 0.0236(3) Uani d . . . 1 . .
I I2 0.42670(4) 0.2033(2) 0.44677(4) 0.0272(3) Uani d . . . 1 . .
I I3 0.24948(4) 0.6735(2) 0.45913(4) 0.0252(3) Uani d . . . 1 . .
I I4 0.08091(4) 0.7374(2) 0.46909(5) 0.0288(3) Uani d . . . 1 . .
N N1 0.5128(5) 0.986(3) 0.1548(6) 0.040(4) Uani d . . . 1 . .
N N2 0.3362(6) 0.724(3) 0.1681(6) 0.034(3) Uani d . . . 1 . .
N N3 0.3724(5) 0.998(3) 0.5801(6) 0.037(3) Uani d . . . 1 . .
N N4 0.3083(6) 1.393(4) 0.7187(6) 0.047(3) Uani d U . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.133(19) ?
C1 C2 . 1.43(2) ?
C2 C3 . 1.379(17) ?
C2 C7 . 1.412(16) ?
C3 C4 . 1.381(17) ?
C3 I1 . 2.092(11) ?
C4 C5 . 1.417(15) ?
C4 I2 . 2.087(13) ?
C5 C6 . 1.376(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.393(19) ?
C6 H6 . 0.95 ?
C7 C8 . 1.440(19) ?
C8 N1 . 1.128(17) ?
C9 N3 . 1.121(15) ?
C9 C10 . 1.462(15) ?
C10 C11 . 1.381(18) ?
C10 C15 . 1.393(17) ?
C11 C12 . 1.434(16) ?
C11 I3 . 2.064(12) ?
C12 C13 . 1.401(17) ?
C12 I4 . 2.097(13) ?
C13 C14 . 1.350(18) ?
C13 H13 . 0.95 ?
C14 C15 . 1.404(17) ?
C14 H14 . 0.95 ?
C15 C16 . 1.42(2) ?
C16 N4 . 1.132(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C2 . . 177.2(16) ?
C3 C2 C7 . . 121.3(12) ?
C3 C2 C1 . . 121.3(11) ?
C7 C2 C1 . . 117.4(12) ?
C2 C3 C4 . . 119.9(11) ?
C2 C3 I1 . . 119.0(9) ?
C4 C3 I1 . . 121.1(9) ?
C3 C4 C5 . . 119.8(12) ?
C3 C4 I2 . . 123.4(8) ?
C5 C4 I2 . . 116.8(9) ?
C6 C5 C4 . . 119.6(12) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C7 . . 121.3(11) ?
C5 C6 H6 . . 119.3 ?
C7 C6 H6 . . 119.3 ?
C6 C7 C2 . . 118.1(12) ?
C6 C7 C8 . . 120.5(11) ?
C2 C7 C8 . . 121.3(13) ?
N1 C8 C7 . . 178.4(16) ?
N3 C9 C10 . . 174.3(17) ?
C11 C10 C15 . . 123.0(11) ?
C11 C10 C9 . . 119.0(11) ?
C15 C10 C9 . . 117.9(12) ?
C10 C11 C12 . . 116.3(11) ?
C10 C11 I3 . . 120.1(8) ?
C12 C11 I3 . . 123.4(10) ?
C13 C12 C11 . . 120.8(12) ?
C13 C12 I4 . . 119.0(9) ?
C11 C12 I4 . . 120.1(9) ?
C14 C13 C12 . . 120.2(11) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 121.0(12) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C10 C15 C14 . . 118.5(12) ?
C10 C15 C16 . . 119.1(11) ?
C14 C15 C16 . . 122.4(12) ?
N4 C16 C15 . . 180.(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 2.(2) ?
C1 C2 C3 C4 . . . . -178.9(13) ?
C7 C2 C3 I1 . . . . -178.8(10) ?
C1 C2 C3 I1 . . . . 0.7(18) ?
C2 C3 C4 C5 . . . . -1.(2) ?
I1 C3 C4 C5 . . . . 179.2(10) ?
C2 C3 C4 I2 . . . . 178.1(10) ?
I1 C3 C4 I2 . . . . -1.5(17) ?
C3 C4 C5 C6 . . . . 0.(2) ?
I2 C4 C5 C6 . . . . -178.8(10) ?
C4 C5 C6 C7 . . . . 0.(2) ?
C5 C6 C7 C2 . . . . 1.(2) ?
C5 C6 C7 C8 . . . . 176.4(13) ?
C3 C2 C7 C6 . . . . -1.(2) ?
C1 C2 C7 C6 . . . . 179.2(13) ?
C3 C2 C7 C8 . . . . -177.0(13) ?
C1 C2 C7 C8 . . . . 3.(2) ?
C15 C10 C11 C12 . . . . 3.9(19) ?
C9 C10 C11 C12 . . . . -177.5(12) ?
C15 C10 C11 I3 . . . . 178.9(10) ?
C9 C10 C11 I3 . . . . -2.6(17) ?
C10 C11 C12 C13 . . . . -4.5(19) ?
I3 C11 C12 C13 . . . . -179.3(9) ?
C10 C11 C12 I4 . . . . 179.5(9) ?
I3 C11 C12 I4 . . . . 4.8(15) ?
C11 C12 C13 C14 . . . . 3.(2) ?
I4 C12 C13 C14 . . . . 179.4(10) ?
C12 C13 C14 C15 . . . . -2.(2) ?
C11 C10 C15 C14 . . . . -2.(2) ?
C9 C10 C15 C14 . . . . 179.3(13) ?
C11 C10 C15 C16 . . . . 179.7(13) ?
C9 C10 C15 C16 . . . . 1.1(19) ?
C13 C14 C15 C10 . . . . 1.(2) ?
C13 C14 C15 C16 . . . . 178.9(13) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5 N3 3_666 0.95 2.69 3.431(18) 134.9 ?
C13 H13 N1 4_586 0.95 2.68 3.376(16) 130.3 ?

