# 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 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_2_solvate
_database_code_depnum_ccdc_archive 'CCDC 1818620'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 I N2, C2 H3 N'
_chemical_formula_sum            'C8 H8 I N3'
_chemical_formula_weight         273.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.835(3)
_cell_length_b                   6.6734(11)
_cell_length_c                   12.462(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     984.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4538
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      31.84

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.205
_shelx_estimated_absorpt_T_min   0.333
_shelx_estimated_absorpt_T_max   0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_T_max  0.7462

_exptl_special_details           
;
 Bruker KRYOFLEX low temperature device.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6457
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.796
_diffrn_reflns_theta_max         31.715
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1756
_reflns_number_gt                1677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0209P)²+0.9507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1756
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0480
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.68560(2) 0.2500 0.80928(2) 0.01563(5) Uani 1 2 d S T P . .
N1 N 0.32959(16) 0.2500 0.51759(16) 0.0181(4) Uani 1 2 d S T P . .
N2 N 0.48079(15) 0.2500 0.41074(15) 0.0152(3) Uani 1 2 d S T P . .
C1 C 0.44309(18) 0.2500 0.51440(17) 0.0156(4) Uani 1 2 d S T P . .
C2 C 0.29503(19) 0.2500 0.41225(19) 0.0188(4) Uani 1 2 d S T P . .
H2 H 0.2185 0.2500 0.3892 0.023 Uiso 1 2 calc R U P . .
C3 C 0.38680(19) 0.2500 0.34541(17) 0.0176(4) Uani 1 2 d S T P . .
H3 H 0.3859 0.2500 0.2692 0.021 Uiso 1 2 calc R U P . .
C4 C 0.5982(2) 0.2500 0.3755(2) 0.0221(4) Uani 1 2 d S T P . .
H4A H 0.6029 0.1954 0.3027 0.033 Uiso 0.5 1 calc R U P . .
H4B H 0.6434 0.1671 0.4243 0.033 Uiso 0.5 1 calc R U P . .
H4C H 0.6273 0.3875 0.3760 0.033 Uiso 0.5 1 calc R U P . .
C5 C 0.51632(19) 0.2500 0.60504(18) 0.0178(4) Uani 1 2 d S T P . .
C6 C 0.5791(2) 0.2500 0.68092(19) 0.0198(4) Uani 1 2 d S T P . .
N3 N 1.0051(2) 0.2500 0.40327(19) 0.0330(5) Uani 1 2 d S T P . .
C7 C 0.8723(2) 0.2500 0.5695(2) 0.0321(6) Uani 1 2 d S T P . .
H7A H 0.8498 0.3878 0.5862 0.048 Uiso 0.5 1 calc R U P . .
H7B H 0.9123 0.1924 0.6310 0.048 Uiso 0.5 1 calc R U P . .
H7C H 0.8049 0.1697 0.5540 0.048 Uiso 0.5 1 calc R U P . .
C8 C 0.9469(2) 0.2500 0.4757(2) 0.0255(5) Uani 1 2 d S T P . .


_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 C6 2.037(2) . ?
N1 C1 1.344(3) . ?
N1 C2 1.375(3) . ?
N2 C1 1.367(3) . ?
N2 C3 1.378(3) . ?
N2 C4 1.457(3) . ?
C1 C5 1.424(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.203(3) . ?
N3 C8 1.136(4) . ?
C7 C8 1.464(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C1 N1 C2 105.60(19) . . ?
C1 N2 C3 107.15(18) . . ?
C1 N2 C4 126.57(18) . . ?
C3 N2 C4 126.28(19) . . ?
N1 C1 N2 110.75(18) . . ?
N1 C1 C5 125.8(2) . . ?
N2 C1 C5 123.5(2) . . ?
C3 C2 N1 110.19(19) . . ?
C3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
C2 C3 N2 106.30(19) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 179.3(2) . . ?
C5 C6 I1 179.9(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C7 179.8(3) . . ?

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
C2 N1 C1 N2 0.000(0) . . . . ?
C2 N1 C1 C5 180.000(0) . . . . ?
C3 N2 C1 N1 0.000(0) . . . . ?
C4 N2 C1 N1 180.000(0) . . . . ?
C3 N2 C1 C5 180.000(0) . . . . ?
C4 N2 C1 C5 0.000(0) . . . . ?
C1 N1 C2 C3 0.000(0) . . . . ?
N1 C2 C3 N2 0.000(0) . . . . ?
C1 N2 C3 C2 0.000(0) . . . . ?
C4 N2 C3 C2 180.000(0) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1818621'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 I N2'
_chemical_formula_sum            'C11 H15 I N2'
_chemical_formula_weight         302.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   19.387(3)
_cell_length_b                   30.384(5)
_cell_length_c                   8.6076(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5070.4(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3341
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      27.23

_exptl_crystal_description       'thin irregular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             2368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6110
_exptl_absorpt_correction_T_max  0.7466

_exptl_special_details           
; 
The crystal was recovered and cleaned from a black sticky gummy wax. 
The crystal was quickly freezed using a Bruker KRYOFLEX 
low temperature device.
;


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24873
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         30.640
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3854
_reflns_number_gt                3257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.995

_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 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL

_refine_special_details          
;
Crystal diffracted poorly even at 100 K.
The crystal was twinned - 2 components.
Rotation matrix 179.9 obtained by cell_now.
The integration was carried out over the 
2 components.
the hexyl chain is very mobily and we used 
SIMU as restraint to describe it.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+13.8334P] 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 
;
 Flack x determined using 1351 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3854
_refine_ls_number_parameters     128
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.30629(2) 0.35128(2) 0.21092(10) 0.03163(12) Uani 1 1 d . . . . .
C1 C 0.2559(4) 0.4072(2) 0.2643(9) 0.0350(14) Uani 1 1 d . . . . .
C2 C 0.2244(4) 0.4396(2) 0.3016(8) 0.0334(14) Uani 1 1 d . . . . .
C3 C 0.1862(4) 0.4771(2) 0.3496(8) 0.0297(13) Uani 1 1 d . . . . .
N1 N 0.1250(3) 0.4771(2) 0.4160(7) 0.0354(13) Uani 1 1 d . . . . .
N2 N 0.2102(3) 0.5189(2) 0.3357(7) 0.0334(12) Uani 1 1 d . . . . .
C4 C 0.1600(5) 0.5457(3) 0.3984(9) 0.0406(16) Uani 1 1 d . . . . .
H4 H 0.161410 0.576862 0.405469 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1089(4) 0.5194(2) 0.4477(11) 0.0385(15) Uani 1 1 d . . . . .
H5 H 0.067743 0.528995 0.497071 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2780(5) 0.5314(3) 0.2722(12) 0.057(2) Uani 1 1 d . U . . .
H6A H 0.273820 0.559659 0.215702 0.068 Uiso 1 1 calc R U . . .
H6B H 0.293503 0.508720 0.197311 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3354(6) 0.5364(4) 0.4101(13) 0.074(3) Uani 1 1 d . U . . .
H7A H 0.318130 0.557813 0.487668 0.089 Uiso 1 1 calc R U . . .
H7B H 0.340597 0.507693 0.463030 0.089 Uiso 1 1 calc R U . . .
C8 C 0.4023(7) 0.5507(5) 0.3568(14) 0.075(3) Uani 1 1 d . U . . .
H8A H 0.396231 0.577654 0.293469 0.090 Uiso 1 1 calc R U . . .
H8B H 0.421662 0.527689 0.288228 0.090 Uiso 1 1 calc R U . . .
C9 C 0.4543(6) 0.5604(5) 0.4845(15) 0.079(3) Uani 1 1 d . U . . .
H9A H 0.434102 0.582132 0.557288 0.095 Uiso 1 1 calc R U . . .
H9B H 0.463292 0.533053 0.543447 0.095 Uiso 1 1 calc R U . . .
C10 C 0.5218(6) 0.5782(5) 0.4235(12) 0.073(3) Uani 1 1 d . U . . .
H10A H 0.536633 0.560566 0.332685 0.088 Uiso 1 1 calc R U . . .
H10B H 0.515458 0.608986 0.389141 0.088 Uiso 1 1 calc R U . . .
C11 C 0.5750(8) 0.5763(8) 0.5442(18) 0.108(5) Uani 1 1 d . U . . .
H11A H 0.558640 0.591770 0.637147 0.161 Uiso 1 1 calc R U . . .
H11B H 0.617137 0.590471 0.506047 0.161 Uiso 1 1 calc R U . . .
H11C H 0.584738 0.545554 0.570093 0.161 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.014(7) . ?
C1 C2 1.201(10) . ?
C2 C3 1.421(10) . ?
C3 N1 1.316(9) . ?
C3 N2 1.357(9) . ?
N1 C5 1.348(9) . ?
N2 C4 1.378(10) . ?
N2 C6 1.474(10) . ?
C4 C5 1.343(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.634(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.442(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.509(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.46(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C2 C1 I1 177.1(7) . . ?
C1 C2 C3 178.1(8) . . ?
N1 C3 N2 110.3(6) . . ?
N1 C3 C2 126.6(7) . . ?
N2 C3 C2 123.1(7) . . ?
C3 N1 C5 107.3(6) . . ?
C3 N2 C4 106.0(6) . . ?
C3 N2 C6 125.4(7) . . ?
C4 N2 C6 128.5(7) . . ?
C5 C4 N2 107.1(7) . . ?
C5 C4 H4 126.5 . . ?
N2 C4 H4 126.5 . . ?
C4 C5 N1 109.3(7) . . ?
C4 C5 H5 125.3 . . ?
N1 C5 H5 125.3 . . ?
N2 C6 C7 111.2(7) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 114.1(10) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 115.1(10) . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C8 113.1(10) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 110.5(10) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N2 C3 N1 C5 -0.6(8) . . . . ?
C2 C3 N1 C5 177.7(7) . . . . ?
N1 C3 N2 C4 0.1(8) . . . . ?
C2 C3 N2 C4 -178.2(7) . . . . ?
N1 C3 N2 C6 177.6(8) . . . . ?
C2 C3 N2 C6 -0.7(11) . . . . ?
C3 N2 C4 C5 0.4(9) . . . . ?
C6 N2 C4 C5 -177.0(8) . . . . ?
N2 C4 C5 N1 -0.8(10) . . . . ?
C3 N1 C5 C4 0.9(9) . . . . ?
C3 N2 C6 C7 -93.6(10) . . . . ?
C4 N2 C6 C7 83.4(11) . . . . ?
N2 C6 C7 C8 -177.1(11) . . . . ?
C6 C7 C8 C9 173.7(12) . . . . ?
C7 C8 C9 C10 -176.2(13) . . . . ?
C8 C9 C10 C11 -165.7(16) . . . . ?

_refine_diff_density_max         1.396
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1818622'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 I N2'
_chemical_formula_sum            'C36 H30 I6 N12'
_chemical_formula_weight         1392.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.295(4)
_cell_length_b                   13.619(2)
_cell_length_c                   14.688(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.934(8)
_cell_angle_gamma                90
_cell_volume                     4559.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9823
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      33.43

_exptl_crystal_description       'small table'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    4.128

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6110
_exptl_absorpt_correction_T_max  0.7466

_exptl_special_details           
; 
The crystals were usually very small and fragile.
The crystal used for data collection 
was quickly freezed using a Bruker KRYOFLEX low temperature device.
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73564
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.417
_diffrn_reflns_theta_max         33.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             16562
_reflns_number_gt                11943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    0.955

_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_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL

_refine_special_details          
;
The imidazole unit is disordered. We tried to model this disorder but
the structure quality did not improve much. The difference between the
two populations is highly unbalence toward one conformer 
(approximately 98:2). Based on this difference we decided to neglect
the disorder. For this reason we omitted several reflections.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)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 
;
 Flack x determined using 4061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         16562
_refine_ls_number_parameters     493
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001

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 0.27680(2) -0.05489(3) 0.08799(3) 0.01695(10) Uani 1 1 d . . . . .
N1 N 0.1716(2) 0.2899(4) 0.1764(4) 0.0170(12) Uani 1 1 d . . . . .
N2 N 0.1042(2) 0.1751(4) 0.1791(4) 0.0177(12) Uani 1 1 d . . . . .
C1 C 0.2273(3) 0.0564(5) 0.1214(5) 0.0203(15) Uani 1 1 d . . . . .
C2 C 0.1976(3) 0.1205(5) 0.1441(5) 0.0176(14) Uani 1 1 d . . . . .
C3 C 0.1582(3) 0.1921(5) 0.1664(4) 0.0166(14) Uani 1 1 d . . . . .
C4 C 0.0829(3) 0.2643(5) 0.1984(5) 0.0213(15) Uani 1 1 d . . . . .
H4 H 0.044874 0.274875 0.210444 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1236(3) 0.3362(5) 0.1982(5) 0.0219(16) Uani 1 1 d . . . . .
H5 H 0.119662 0.404070 0.210421 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2271(3) 0.3352(6) 0.1696(5) 0.0245(17) Uani 1 1 d . . . . .
H6A H 0.241293 0.306523 0.117140 0.037 Uiso 1 1 calc R U . . .
H6B H 0.256021 0.323662 0.227309 0.037 Uiso 1 1 calc R U . . .
H6C H 0.221471 0.406038 0.159738 0.037 Uiso 1 1 calc R U . . .
I2 I 0.55943(2) 0.48866(3) 0.14968(3) 0.01818(11) Uani 1 1 d . . . . .
N3 N 0.4424(2) 0.1335(4) 0.1313(4) 0.0186(13) Uani 1 1 d . . . . .
N4 N 0.5331(2) 0.0873(4) 0.1240(4) 0.0210(13) Uani 1 1 d . . . . .
C7 C 0.5294(3) 0.3489(5) 0.1319(5) 0.0220(16) Uani 1 1 d . . . . .
C8 C 0.5140(3) 0.2642(6) 0.1295(5) 0.0196(15) Uani 1 1 d . . . . .
C9 C 0.4978(3) 0.1641(5) 0.1275(5) 0.0181(14) Uani 1 1 d . . . . .
C10 C 0.4988(3) 0.0064(5) 0.1237(5) 0.0196(15) Uani 1 1 d . . . . .
H10 H 0.511807 -0.059346 0.120128 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4429(3) 0.0334(5) 0.1291(5) 0.0207(15) Uani 1 1 d . . . . .
H11 H 0.410856 -0.009185 0.131061 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3933(3) 0.1967(6) 0.1376(6) 0.0282(18) Uani 1 1 d . . . . .
H12A H 0.383148 0.236821 0.081156 0.042 Uiso 1 1 calc R U . . .
H12B H 0.404064 0.239554 0.191993 0.042 Uiso 1 1 calc R U . . .
H12C H 0.359486 0.156318 0.143761 0.042 Uiso 1 1 calc R U . . .
I3 I 0.22245(2) 0.51589(3) 0.39890(3) 0.01731(10) Uani 1 1 d . . . . .
N5 N 0.3283(2) 0.8644(4) 0.3327(4) 0.0184(12) Uani 1 1 d . . . . .
N6 N 0.3961(2) 0.7551(4) 0.3208(4) 0.0204(13) Uani 1 1 d . . . . .
C13 C 0.2722(3) 0.6261(6) 0.3682(5) 0.0203(15) Uani 1 1 d . . . . .
C14 C 0.3040(3) 0.6923(6) 0.3518(5) 0.0220(16) Uani 1 1 d . . . . .
C15 C 0.3429(3) 0.7686(5) 0.3354(4) 0.0146(13) Uani 1 1 d . . . . .
C16 C 0.4166(3) 0.8468(5) 0.3072(5) 0.0227(16) Uani 1 1 d . . . . .
H16 H 0.454040 0.860643 0.294048 0.027 Uiso 1 1 calc R U . . .
C17 C 0.3754(3) 0.9154(6) 0.3152(5) 0.0232(16) Uani 1 1 d . . . . .
H17 H 0.378680 0.984554 0.309739 0.028 Uiso 1 1 calc R U . . .
C18 C 0.2723(3) 0.9071(6) 0.3447(5) 0.0258(17) Uani 1 1 d . . . . .
H18A H 0.265572 0.890104 0.406454 0.039 Uiso 1 1 calc R U . . .
H18B H 0.240286 0.880920 0.296874 0.039 Uiso 1 1 calc R U . . .
H18C H 0.273850 0.978637 0.338690 0.039 Uiso 1 1 calc R U . . .
I4 I 0.44416(2) 0.57167(3) 0.34512(3) 0.01945(11) Uani 1 1 d . . . . .
N7 N 0.5607(2) 0.2124(5) 0.3605(4) 0.0190(13) Uani 1 1 d . . . . .
N8 N 0.4700(2) 0.1732(5) 0.3746(4) 0.0224(13) Uani 1 1 d . . . . .
C19 C 0.4759(3) 0.4334(5) 0.3604(5) 0.0212(16) Uani 1 1 d . . . . .
C20 C 0.4918(3) 0.3483(6) 0.3641(5) 0.0221(16) Uani 1 1 d . . . . .
C21 C 0.5063(3) 0.2477(5) 0.3676(5) 0.0185(15) Uani 1 1 d . . . . .
C22 C 0.5022(3) 0.0902(6) 0.3727(5) 0.0213(16) Uani 1 1 d . . . . .
H22 H 0.487710 0.025559 0.377105 0.026 Uiso 1 1 calc R U . . .
C23 C 0.5578(3) 0.1114(6) 0.3636(5) 0.0264(17) Uani 1 1 d . . . . .
H23 H 0.588272 0.066114 0.360093 0.032 Uiso 1 1 calc R U . . .
C24 C 0.6113(3) 0.2706(6) 0.3508(5) 0.0224(16) Uani 1 1 d . . . . .
H24A H 0.642733 0.261415 0.405761 0.034 Uiso 1 1 calc R U . . .
H24B H 0.600296 0.340098 0.344809 0.034 Uiso 1 1 calc R U . . .
H24C H 0.624983 0.249458 0.295109 0.034 Uiso 1 1 calc R U . . .
I5 I 0.14745(2) 0.62043(3) 0.11694(3) 0.01837(11) Uani 1 1 d . . . . .
N9 N 0.3797(2) 0.6352(4) 0.0800(4) 0.0184(13) Uani 1 1 d . . . . .
N10 N 0.3499(2) 0.7912(4) 0.0596(4) 0.0193(13) Uani 1 1 d . . . . .
C25 C 0.2310(3) 0.6516(5) 0.1069(5) 0.0197(15) Uani 1 1 d . . . . .
C26 C 0.2784(3) 0.6722(5) 0.0950(5) 0.0200(15) Uani 1 1 d . . . . .
C27 C 0.3348(3) 0.7010(5) 0.0790(5) 0.0191(15) Uani 1 1 d . . . . .
C28 C 0.4071(3) 0.7831(6) 0.0498(5) 0.0225(16) Uani 1 1 d . . . . .
H28 H 0.430442 0.836036 0.036083 0.027 Uiso 1 1 calc R U . . .
C29 C 0.4254(3) 0.6879(5) 0.0629(5) 0.0205(15) Uani 1 1 d . . . . .
H29 H 0.463257 0.663368 0.060337 0.025 Uiso 1 1 calc R U . . .
C30 C 0.3760(3) 0.5290(5) 0.0914(5) 0.0199(15) Uani 1 1 d . . . . .
H30A H 0.413138 0.504590 0.128531 0.030 Uiso 1 1 calc R U . . .
H30B H 0.368421 0.497374 0.030128 0.030 Uiso 1 1 calc R U . . .
H30C H 0.344027 0.513737 0.123163 0.030 Uiso 1 1 calc R U . . .
I6 I 0.14321(2) 0.70075(3) 0.60951(3) 0.01926(11) Uani 1 1 d . . . . .
N11 N 0.3777(2) 0.7062(4) 0.5761(4) 0.0165(12) Uani 1 1 d . . . . .
N12 N 0.3494(2) 0.8634(4) 0.5656(4) 0.0209(13) Uani 1 1 d . . . . .
C31 C 0.2279(3) 0.7236(5) 0.5966(5) 0.0192(15) Uani 1 1 d . . . . .
C32 C 0.2765(3) 0.7452(5) 0.5886(5) 0.0195(15) Uani 1 1 d . . . . .
C33 C 0.3328(3) 0.7711(5) 0.5763(5) 0.0183(14) Uani 1 1 d . . . . .
C34 C 0.4070(3) 0.8565(5) 0.5562(5) 0.0201(15) Uani 1 1 d . . . . .
H34 H 0.431146 0.910257 0.546870 0.024 Uiso 1 1 calc R U . . .
C35 C 0.4237(3) 0.7610(5) 0.5623(5) 0.0186(15) Uani 1 1 d . . . . .
H35 H 0.461231 0.736705 0.557693 0.022 Uiso 1 1 calc R U . . .
C36 C 0.3755(3) 0.6003(5) 0.5866(5) 0.0211(16) Uani 1 1 d . . . . .
H36A H 0.385942 0.568417 0.532508 0.032 Uiso 1 1 calc R U . . .
H36B H 0.335683 0.580719 0.591253 0.032 Uiso 1 1 calc R U . . .
H36C H 0.403224 0.580361 0.643196 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.025(7) . ?
N1 C3 1.369(8) . ?
N1 C5 1.378(9) . ?
N1 C6 1.455(8) . ?
N2 C3 1.329(8) . ?
N2 C4 1.365(9) . ?
C1 C2 1.202(9) . ?
C2 C3 1.425(10) . ?
C4 C5 1.363(10) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
I2 C7 2.027(7) . ?
N3 C11 1.364(9) . ?
N3 C9 1.368(8) . ?
N3 C12 1.450(9) . ?
N4 C9 1.338(9) . ?
N4 C10 1.359(9) . ?
C7 C8 1.207(10) . ?
C8 C9 1.412(10) . ?
C10 C11 1.373(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
I3 C13 2.004(7) . ?
N5 C15 1.347(9) . ?
N5 C17 1.367(9) . ?
N5 C18 1.470(9) . ?
N6 C15 1.313(8) . ?
N6 C16 1.367(9) . ?
C13 C14 1.221(10) . ?
C14 C15 1.432(10) . ?
C16 C17 1.362(10) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
I4 C19 2.019(8) . ?
N7 C21 1.378(8) . ?
N7 C23 1.378(9) . ?
N7 C24 1.452(9) . ?
N8 C21 1.338(9) . ?
N8 C22 1.361(9) . ?
C19 C20 1.214(10) . ?
C20 C21 1.410(10) . ?
C22 C23 1.360(10) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
I5 C25 2.028(7) . ?
N9 C29 1.350(8) . ?
N9 C27 1.376(8) . ?
N9 C30 1.461(9) . ?
N10 C27 1.324(9) . ?
N10 C28 1.372(8) . ?
C25 C26 1.186(9) . ?
C26 C27 1.436(9) . ?
C28 C29 1.367(10) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
I6 C31 2.044(7) . ?
N11 C35 1.355(8) . ?
N11 C33 1.369(8) . ?
N11 C36 1.453(9) . ?
N12 C33 1.334(9) . ?
N12 C34 1.380(8) . ?
C31 C32 1.199(9) . ?
C32 C33 1.406(9) . ?
C34 C35 1.355(10) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C3 N1 C5 107.0(6) . . ?
C3 N1 C6 126.3(6) . . ?
C5 N1 C6 126.7(6) . . ?
C3 N2 C4 105.6(6) . . ?
C2 C1 I1 177.6(7) . . ?
C1 C2 C3 175.1(7) . . ?
N2 C3 N1 110.9(6) . . ?
N2 C3 C2 125.9(6) . . ?
N1 C3 C2 123.2(6) . . ?
C5 C4 N2 110.9(6) . . ?
C5 C4 H4 124.6 . . ?
N2 C4 H4 124.6 . . ?
C4 C5 N1 105.7(6) . . ?
C4 C5 H5 127.2 . . ?
N1 C5 H5 127.2 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 N3 C9 107.0(6) . . ?
C11 N3 C12 127.2(6) . . ?
C9 N3 C12 125.8(6) . . ?
C9 N4 C10 105.7(5) . . ?
C8 C7 I2 174.2(7) . . ?
C7 C8 C9 178.2(8) . . ?
N4 C9 N3 110.8(6) . . ?
N4 C9 C8 126.3(6) . . ?
N3 C9 C8 122.9(6) . . ?
N4 C10 C11 110.2(6) . . ?
N4 C10 H10 124.9 . . ?
C11 C10 H10 124.9 . . ?
N3 C11 C10 106.3(6) . . ?
N3 C11 H11 126.8 . . ?
C10 C11 H11 126.8 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 N5 C17 106.8(6) . . ?
C15 N5 C18 127.2(6) . . ?
C17 N5 C18 125.9(6) . . ?
C15 N6 C16 105.4(6) . . ?
C14 C13 I3 177.9(6) . . ?
C13 C14 C15 177.8(8) . . ?
N6 C15 N5 111.9(6) . . ?
N6 C15 C14 125.3(7) . . ?
N5 C15 C14 122.8(6) . . ?
C17 C16 N6 109.9(7) . . ?
C17 C16 H16 125.1 . . ?
N6 C16 H16 125.1 . . ?
C16 C17 N5 106.0(7) . . ?
C16 C17 H17 127.0 . . ?
N5 C17 H17 127.0 . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 N7 C23 107.1(6) . . ?
C21 N7 C24 126.5(6) . . ?
C23 N7 C24 126.4(6) . . ?
C21 N8 C22 105.5(5) . . ?
C20 C19 I4 175.3(7) . . ?
C19 C20 C21 176.1(8) . . ?
N8 C21 N7 110.3(6) . . ?
N8 C21 C20 126.1(6) . . ?
N7 C21 C20 123.5(7) . . ?
C23 C22 N8 111.5(7) . . ?
C23 C22 H22 124.3 . . ?
N8 C22 H22 124.3 . . ?
C22 C23 N7 105.6(6) . . ?
C22 C23 H23 127.2 . . ?
N7 C23 H23 127.2 . . ?
N7 C24 H24A 109.5 . . ?
N7 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N7 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C29 N9 C27 106.2(6) . . ?
C29 N9 C30 128.0(6) . . ?
C27 N9 C30 125.7(6) . . ?
C27 N10 C28 104.8(6) . . ?
C26 C25 I5 175.5(6) . . ?
C25 C26 C27 177.6(8) . . ?
N10 C27 N9 111.8(6) . . ?
N10 C27 C26 125.6(6) . . ?
N9 C27 C26 122.6(7) . . ?
C29 C28 N10 110.1(6) . . ?
C29 C28 H28 124.9 . . ?
N10 C28 H28 124.9 . . ?
N9 C29 C28 107.1(6) . . ?
N9 C29 H29 126.4 . . ?
C28 C29 H29 126.4 . . ?
N9 C30 H30A 109.5 . . ?
N9 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N9 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C35 N11 C33 105.8(6) . . ?
C35 N11 C36 127.6(6) . . ?
C33 N11 C36 126.6(6) . . ?
C33 N12 C34 105.0(6) . . ?
C32 C31 I6 174.5(6) . . ?
C31 C32 C33 178.2(8) . . ?
N12 C33 N11 111.6(6) . . ?
N12 C33 C32 123.5(6) . . ?
N11 C33 C32 124.9(7) . . ?
C35 C34 N12 109.3(6) . . ?
C35 C34 H34 125.4 . . ?
N12 C34 H34 125.4 . . ?
C34 C35 N11 108.3(6) . . ?
C34 C35 H35 125.9 . . ?
N11 C35 H35 125.9 . . ?
N11 C36 H36A 109.5 . . ?
N11 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N11 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C4 N2 C3 N1 -0.5(7) . . . . ?
C4 N2 C3 C2 -179.7(7) . . . . ?
C5 N1 C3 N2 1.0(7) . . . . ?
C6 N1 C3 N2 178.5(6) . . . . ?
C5 N1 C3 C2 -179.7(6) . . . . ?
C6 N1 C3 C2 -2.3(10) . . . . ?
C3 N2 C4 C5 -0.3(8) . . . . ?
N2 C4 C5 N1 0.9(8) . . . . ?
C3 N1 C5 C4 -1.2(7) . . . . ?
C6 N1 C5 C4 -178.6(6) . . . . ?
C10 N4 C9 N3 1.2(7) . . . . ?
C10 N4 C9 C8 179.8(7) . . . . ?
C11 N3 C9 N4 -0.6(8) . . . . ?
C12 N3 C9 N4 178.7(6) . . . . ?
C11 N3 C9 C8 -179.2(7) . . . . ?
C12 N3 C9 C8 0.1(11) . . . . ?
C9 N4 C10 C11 -1.4(8) . . . . ?
C9 N3 C11 C10 -0.2(8) . . . . ?
C12 N3 C11 C10 -179.6(7) . . . . ?
N4 C10 C11 N3 1.0(8) . . . . ?
C16 N6 C15 N5 -0.6(8) . . . . ?
C16 N6 C15 C14 179.0(6) . . . . ?
C17 N5 C15 N6 0.0(8) . . . . ?
C18 N5 C15 N6 179.1(6) . . . . ?
C17 N5 C15 C14 -179.6(6) . . . . ?
C18 N5 C15 C14 -0.5(10) . . . . ?
C15 N6 C16 C17 0.9(8) . . . . ?
N6 C16 C17 N5 -0.9(8) . . . . ?
C15 N5 C17 C16 0.6(8) . . . . ?
C18 N5 C17 C16 -178.6(6) . . . . ?
C22 N8 C21 N7 0.5(8) . . . . ?
C22 N8 C21 C20 178.2(7) . . . . ?
C23 N7 C21 N8 -0.2(8) . . . . ?
C24 N7 C21 N8 179.3(6) . . . . ?
C23 N7 C21 C20 -178.0(7) . . . . ?
C24 N7 C21 C20 1.5(11) . . . . ?
C21 N8 C22 C23 -0.6(8) . . . . ?
N8 C22 C23 N7 0.5(9) . . . . ?
C21 N7 C23 C22 -0.2(8) . . . . ?
C24 N7 C23 C22 -179.7(7) . . . . ?
C28 N10 C27 N9 -1.4(8) . . . . ?
C28 N10 C27 C26 -179.8(7) . . . . ?
C29 N9 C27 N10 1.8(8) . . . . ?
C30 N9 C27 N10 -174.6(6) . . . . ?
C29 N9 C27 C26 -179.8(6) . . . . ?
C30 N9 C27 C26 3.8(11) . . . . ?
C27 N10 C28 C29 0.5(8) . . . . ?
C27 N9 C29 C28 -1.4(8) . . . . ?
C30 N9 C29 C28 174.9(6) . . . . ?
N10 C28 C29 N9 0.6(8) . . . . ?
C34 N12 C33 N11 1.3(8) . . . . ?
C34 N12 C33 C32 179.8(6) . . . . ?
C35 N11 C33 N12 -1.5(8) . . . . ?
C36 N11 C33 N12 179.7(6) . . . . ?
C35 N11 C33 C32 180.0(6) . . . . ?
C36 N11 C33 C32 1.2(11) . . . . ?
C33 N12 C34 C35 -0.6(8) . . . . ?
N12 C34 C35 N11 -0.4(8) . . . . ?
C33 N11 C35 C34 1.1(8) . . . . ?
C36 N11 C35 C34 179.9(6) . . . . ?

_refine_diff_density_max         1.144
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.202

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1818705'
_audit_update_record             
;
2018-01-22 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        2-iodoethynylpyridine
_chemical_name_common            ?
_chemical_melting_point          399
_chemical_formula_moiety         '3(C7 H4 I1 N1)'
_chemical_formula_sum            'C21 H12 I3 N3'
_chemical_formula_weight         687.04

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.0353(7)
_cell_length_b                   14.2760(9)
_cell_length_c                   14.2688(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2247.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.65
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.377
_exptl_crystal_size_min          0.188
_exptl_absorpt_coefficient_mu    4.181
_shelx_estimated_absorpt_T_min   0.261
_shelx_estimated_absorpt_T_max   0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            26238
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         29.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2968
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+92.2532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     172
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.1183
_refine_ls_wR_factor_ref         0.2970
_refine_ls_wR_factor_gt          0.2951
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.4536(3) 0.87021(18) 0.80471(14) 0.0522(6) Uani 0.5 1 d D . P A -1
N1 N 0.693(3) 0.7971(16) 0.4880(16) 0.048(4) Uani 0.5 1 d D . P A -1
C1 C 0.761(2) 0.7946(15) 0.4073(15) 0.042(4) Uani 0.5 1 d D . P A -1
H1 H 0.796620 0.738071 0.385892 0.050 Uiso 0.5 1 calc R U P A -1
C2 C 0.774(2) 0.8776(14) 0.3579(15) 0.046(4) Uani 0.5 1 d D . P A -1
H2 H 0.817724 0.877056 0.300317 0.055 Uiso 0.5 1 calc R U P A -1
C3 C 0.727(3) 0.9605(14) 0.3900(16) 0.052(5) Uani 0.5 1 d D . P A -1
H3 H 0.741010 1.016587 0.355884 0.062 Uiso 0.5 1 calc R U P A -1
C4 C 0.659(3) 0.9633(16) 0.4713(17) 0.048(4) Uani 0.5 1 d D . P A -1
H4 H 0.624842 1.020036 0.493463 0.058 Uiso 0.5 1 calc R U P A -1
C5 C 0.644(3) 0.8796(15) 0.5192(18) 0.054(4) Uani 0.5 1 d D . P A -1
C6 C 0.586(3) 0.8812(18) 0.6019(15) 0.050(6) Uani 0.5 1 d D . P A -1
C7 C 0.539(4) 0.881(4) 0.668(2) 0.0522(6) Uani 0.5 1 d D . P A -1
I2 I 0.4104(4) 0.5037(2) 0.8700(3) 0.0479(5) Uani 0.5 1 d D . P B -1
N2 N 0.356(3) 0.8587(13) 0.9927(19) 0.054(4) Uani 0.5 1 d D . P B -1
C8 C 0.329(3) 0.9386(15) 1.0417(17) 0.048(4) Uani 0.5 1 d D . P B -1
H8 H 0.359928 0.997683 1.022575 0.058 Uiso 0.5 1 calc R U P B -1
C9 C 0.255(2) 0.9311(15) 1.1192(15) 0.052(5) Uani 0.5 1 d D . P B -1
H9 H 0.233724 0.986261 1.152517 0.062 Uiso 0.5 1 calc R U P B -1
C10 C 0.211(2) 0.8461(13) 1.1498(16) 0.046(4) Uani 0.5 1 d D . P B -1
H10 H 0.155488 0.843782 1.200534 0.055 Uiso 0.5 1 calc R U P B -1
C11 C 0.249(2) 0.7638(14) 1.1066(16) 0.042(4) Uani 0.5 1 d D . P B -1
H11 H 0.229337 0.703990 1.131719 0.050 Uiso 0.5 1 calc R U P B -1
C12 C 0.316(3) 0.7734(14) 1.0246(18) 0.048(4) Uani 0.5 1 d D . P B -1
C13 C 0.348(3) 0.6955(17) 0.9771(19) 0.059(8) Uani 0.5 1 d D . P B -1
C14 C 0.379(5) 0.642(3) 0.928(4) 0.0499(6) Uani 0.5 1 d D . P B -1
I3 I 0.6308(3) 0.62395(16) 0.5738(2) 0.0499(6) Uani 0.5 1 d D . P C -1
N3 N 0.472(4) 0.3335(16) 0.780(3) 0.056(5) Uani 0.5 1 d D . P C -1
C15 C 0.441(4) 0.2484(15) 0.818(3) 0.059(6) Uani 0.5 1 d D . P C -1
H15 H 0.391632 0.246325 0.873009 0.071 Uiso 0.5 1 calc R U P C -1
C16 C 0.479(5) 0.1657(15) 0.778(3) 0.054(6) Uani 0.5 1 d D . P C -1
H16 H 0.458739 0.107106 0.804976 0.065 Uiso 0.5 1 calc R U P C -1
C17 C 0.548(5) 0.1692(14) 0.697(3) 0.054(6) Uani 0.5 1 d D . P C -1
H17 H 0.572841 0.112796 0.667335 0.065 Uiso 0.5 1 calc R U P C -1
C18 C 0.580(5) 0.2550(14) 0.659(3) 0.059(6) Uani 0.5 1 d D . P C -1
H18 H 0.631677 0.257897 0.605587 0.071 Uiso 0.5 1 calc R U P C -1
C19 C 0.536(5) 0.3365(14) 0.699(3) 0.056(5) Uani 0.5 1 d D . P C -1
C20 C 0.569(3) 0.4198(16) 0.661(2) 0.057(7) Uani 0.5 1 d D . P C -1
C21 C 0.583(7) 0.489(4) 0.631(6) 0.0479(5) Uani 0.5 1 d D . P C -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.16(4) . ?
N1 C1 1.370(16) . ?
N1 C5 1.370(16) . ?
C1 C2 1.386(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.34(3) . ?
C6 C7 1.08(4) . ?
I2 C14 2.17(4) . ?
N2 C8 1.372(16) . ?
N2 C12 1.374(16) . ?
C8 C9 1.378(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.35(3) . ?
C13 C14 1.09(4) . ?
I3 C21 2.17(4) . ?
N3 C19 1.363(16) . ?
N3 C15 1.373(16) . ?
C15 C16 1.383(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.35(3) . ?
C20 C21 1.08(4) . ?

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
C1 N1 C5 121(2) . . ?
N1 C1 C2 117.7(18) . . ?
N1 C1 H1 121.2 . . ?
C2 C1 H1 121.2 . . ?
C3 C2 C1 121.7(17) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.8(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 117.0(16) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 N1 119.3(19) . . ?
C6 C5 C4 118.4(17) . . ?
N1 C5 C4 122.2(18) . . ?
C7 C6 C5 179(4) . . ?
C6 C7 I1 175(4) . . ?
C8 N2 C12 120(2) . . ?
N2 C8 C9 118.3(18) . . ?
N2 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 122.1(17) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 119.9(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 116.6(15) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
C13 C12 N2 118.6(18) . . ?
C13 C12 C11 118.6(17) . . ?
N2 C12 C11 122.7(18) . . ?
C14 C13 C12 169(4) . . ?
C13 C14 I2 158(5) . . ?
C19 N3 C15 120(2) . . ?
N3 C15 C16 120.9(19) . . ?
N3 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.2(18) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.0(16) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.3(17) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 N3 120(2) . . ?
C20 C19 C18 118.7(18) . . ?
N3 C19 C18 120.6(19) . . ?
C21 C20 C19 173(6) . . ?
C20 C21 I3 174(6) . . ?

_refine_diff_density_max         1.716
_refine_diff_density_min         -2.507
_refine_diff_density_rms         0.283


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
