# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_L1a
_database_code_depnum_ccdc_archive 'CCDC 1861306'
_audit_update_record             
;
2019-01-07 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13.20 H9.80 I2 N4.60'
_chemical_formula_weight         486.66

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.5338(8)
_cell_length_b                   10.4983(5)
_cell_length_c                   28.7697(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5295.8(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    449
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.442
_exptl_crystal_F_000             3635
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    4.746
_shelx_estimated_absorpt_T_min   0.253
_shelx_estimated_absorpt_T_max   0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3832
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            108372
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9023
_reflns_number_gt                7538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
'Refined as a 2-component inversion twin.,Twin,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+40.2012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9023
_refine_ls_number_parameters     434
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 0.177 936 458 ' '
2 0.750 0.750 0.185 939 458 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 0 2 1.416
2 2 3 5.001
2 2 4 5.342
0 0 8 5.671
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
; 
Structural refinement of Q-peaks from the residual electron density as solvent 
molecules were unsuccessful. The data was then processed with the SQUEEZE procedure: 
Spek, A. L. Acta Cryst. 2015, C71, 9-18. 915 electrons in the solvent-assesible void , which corresponded to 42 acetonitrile molecules, were found in the unit cell and has been removed by SQUEEZE procedure.
;
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 0.41035(6) 0.54798(11) -0.11738(5) 0.0575(3) Uani 1 1 d . . . . .
I2 I -0.16622(6) -0.05179(11) -0.13925(5) 0.0599(3) Uani 1 1 d . . . . .
N1 N 0.1907(6) 0.1879(11) -0.1363(6) 0.046(3) Uani 1 1 d . . . . .
N2 N 0.0485(7) 0.3069(13) -0.1185(5) 0.050(3) Uani 1 1 d . . . . .
C1 C 0.3120(10) 0.4383(15) -0.1183(7) 0.050(4) Uani 1 1 d . . . . .
C2 C 0.2549(11) 0.3861(18) -0.1203(7) 0.063(5) Uani 1 1 d . . . . .
C3 C 0.1859(8) 0.3162(15) -0.1225(7) 0.047(4) Uani 1 1 d . . . . .
C4 C 0.1166(7) 0.3670(16) -0.1135(6) 0.041(4) Uani 1 1 d . . . . .
H4 H 0.115396 0.450754 -0.103039 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1240(10) 0.1315(17) -0.1389(8) 0.062(5) Uani 1 1 d . . . . .
H5 H 0.122908 0.046153 -0.147453 0.075 Uiso 1 1 calc R U . . .
C6 C 0.0569(8) 0.1896(15) -0.1298(5) 0.038(4) Uani 1 1 d . . . . .
C7 C -0.0133(8) 0.1155(17) -0.1344(7) 0.055(4) Uani 1 1 d . . . . .
C8 C -0.0694(10) 0.0473(19) -0.1343(8) 0.064(5) Uani 1 1 d . . . . .
I3 I 0.70881(6) -0.55288(11) 0.00720(4) 0.0559(3) Uani 1 1 d . . . . .
I4 I 0.13593(6) 0.05674(11) -0.01215(4) 0.0565(3) Uani 1 1 d . . . . .
N3 N 0.3510(7) -0.3097(13) 0.0077(5) 0.050(3) Uani 1 1 d . . . . .
N4 N 0.4924(7) -0.2022(14) -0.0132(5) 0.051(4) Uani 1 1 d . . . . .
C9 C 0.6129(12) -0.450(2) 0.0058(8) 0.074(6) Uani 1 1 d . . . . .
C10 C 0.5530(10) -0.3913(18) 0.0041(7) 0.057(5) Uani 1 1 d . . . . .
C11 C 0.4900(9) -0.3130(18) -0.0001(7) 0.056(5) Uani 1 1 d . . . . .
C12 C 0.4139(9) -0.3724(15) 0.0099(6) 0.045(4) Uani 1 1 d . . . . .
H12 H 0.412170 -0.458045 0.018011 0.053 Uiso 1 1 calc R U . . .
C13 C 0.4234(9) -0.1311(15) -0.0157(7) 0.054(4) Uani 1 1 d . . . . .
H13 H 0.424652 -0.045932 -0.024605 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3571(9) -0.1857(17) -0.0054(6) 0.050(4) Uani 1 1 d . . . . .
C15 C 0.2873(8) -0.1149(18) -0.0098(7) 0.055(4) Uani 1 1 d . U . . .
C16 C 0.2322(8) -0.0469(15) -0.0088(7) 0.049(3) Uani 1 1 d . U . . .
I5 I 0.54573(6) 0.05777(12) -0.38572(5) 0.0612(3) Uani 1 1 d . . . . .
I6 I -0.02639(6) -0.55391(12) -0.36867(5) 0.0606(3) Uani 1 1 d . . . . .
N5 N 0.3273(6) -0.3035(13) -0.3675(5) 0.044(3) Uani 1 1 d . . . . .
N6 N 0.1919(6) -0.1965(14) -0.3851(6) 0.054(4) Uani 1 1 d . . . . .
C17 C 0.4534(8) -0.0474(16) -0.3833(7) 0.053(3) Uani 1 1 d . U . . .
C18 C 0.3940(7) -0.1112(16) -0.3792(6) 0.047(3) Uani 1 1 d . U . . .
C19 C 0.3250(7) -0.1882(17) -0.3771(5) 0.040(4) Uani 1 1 d . . . . .
C20 C 0.2572(8) -0.1257(14) -0.3854(6) 0.046(4) Uani 1 1 d . . . . .
H20 H 0.255947 -0.038415 -0.390914 0.055 Uiso 1 1 calc R U . . .
C21 C 0.2654(8) -0.3637(15) -0.3637(6) 0.048(4) Uani 1 1 d . . . . .
H21 H 0.267892 -0.447502 -0.353258 0.058 Uiso 1 1 calc R U . . .
C22 C 0.1949(7) -0.3156(14) -0.3736(6) 0.040(4) Uani 1 1 d . . . . .
C23 C 0.1288(10) -0.383(2) -0.3724(7) 0.060(5) Uani 1 1 d . . . . .
C24 C 0.0712(11) -0.4561(19) -0.3711(9) 0.074(6) Uani 1 1 d . . . . .
I7 I 0.12517(6) -0.56217(11) -0.24462(4) 0.0604(3) Uani 1 1 d . . . . .
I8 I 0.69592(6) 0.05326(11) -0.25981(5) 0.0608(3) Uani 1 1 d . . . . .
N7 N 0.4783(6) -0.3076(12) -0.2456(6) 0.050(3) Uani 1 1 d . . . . .
N8 N 0.3363(7) -0.1896(12) -0.2535(6) 0.051(4) Uani 1 1 d . . . . .
C25 C 0.6008(8) -0.0560(14) -0.2594(6) 0.042(4) Uani 1 1 d . . . . .
C26 C 0.5435(8) -0.1078(14) -0.2571(7) 0.046(4) Uani 1 1 d . . . . .
C27 C 0.4742(7) -0.1822(14) -0.2542(6) 0.039(4) Uani 1 1 d . . . . .
C28 C 0.4032(9) -0.1209(15) -0.2580(7) 0.055(4) Uani 1 1 d . . . . .
H28 H 0.401198 -0.033729 -0.263531 0.066 Uiso 1 1 calc R U . . .
C29 C 0.4182(9) -0.3725(17) -0.2432(6) 0.055(4) Uani 1 1 d . . . . .
H29 H 0.423088 -0.459838 -0.238569 0.067 Uiso 1 1 calc R U . . .
C30 C 0.3424(9) -0.3210(14) -0.2469(6) 0.043(4) Uani 1 1 d . . . . .
C31 C 0.2742(10) -0.3950(15) -0.2461(6) 0.054(4) Uani 1 1 d . . . . .
C32 C 0.2218(9) -0.4601(15) -0.2458(7) 0.056(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.073(17) . ?
I2 C8 1.996(18) . ?
N1 C5 1.31(2) . ?
N1 C3 1.406(17) . ?
N2 C6 1.281(17) . ?
N2 C4 1.357(18) . ?
C1 C2 1.14(2) . ?
C2 C3 1.42(2) . ?
C3 C4 1.352(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.35(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(19) . ?
C7 C8 1.22(2) . ?
I3 C9 2.00(2) . ?
I4 C16 2.010(13) . ?
N3 C12 1.29(2) . ?
N3 C14 1.36(2) . ?
N4 C11 1.22(2) . ?
N4 C13 1.42(2) . ?
C9 C10 1.22(3) . ?
C10 C11 1.38(2) . ?
C11 C12 1.50(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.33(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.44(2) . ?
C15 C16 1.20(2) . ?
I5 C17 1.961(15) . ?
I6 C24 1.997(19) . ?
N5 C19 1.24(2) . ?
N5 C21 1.261(19) . ?
N6 C22 1.29(2) . ?
N6 C20 1.365(18) . ?
C17 C18 1.24(2) . ?
C18 C19 1.456(19) . ?
C19 C20 1.38(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.37(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.36(2) . ?
C23 C24 1.27(3) . ?
I7 C32 2.006(16) . ?
I8 C25 2.024(14) . ?
N7 C29 1.26(2) . ?
N7 C27 1.34(2) . ?
N8 C28 1.382(19) . ?
N8 C30 1.396(19) . ?
C25 C26 1.144(19) . ?
C26 C27 1.447(19) . ?
C27 C28 1.405(19) . ?
C28 H28 0.9300 . ?
C29 C30 1.44(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.43(2) . ?
C31 C32 1.14(2) . ?

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
C5 N1 C3 113.3(14) . . ?
C6 N2 C4 111.9(14) . . ?
C2 C1 I1 174.5(16) . . ?
C1 C2 C3 177(2) . . ?
C4 C3 N1 119.0(14) . . ?
C4 C3 C2 123.7(15) . . ?
N1 C3 C2 117.3(14) . . ?
C3 C4 N2 125.9(15) . . ?
C3 C4 H4 117.0 . . ?
N2 C4 H4 117.0 . . ?
N1 C5 C6 124.1(16) . . ?
N1 C5 H5 117.9 . . ?
C6 C5 H5 117.9 . . ?
N2 C6 C5 125.6(15) . . ?
N2 C6 C7 116.0(15) . . ?
C5 C6 C7 118.4(15) . . ?
C8 C7 C6 173(2) . . ?
C7 C8 I2 173.7(18) . . ?
C12 N3 C14 115.9(14) . . ?
C11 N4 C13 119.1(14) . . ?
C10 C9 I3 178(2) . . ?
C9 C10 C11 173(2) . . ?
N4 C11 C10 124.5(17) . . ?
N4 C11 C12 118.9(15) . . ?
C10 C11 C12 116.5(17) . . ?
N3 C12 C11 122.7(15) . . ?
N3 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C14 C13 N4 120.3(14) . . ?
C14 C13 H13 119.8 . . ?
N4 C13 H13 119.8 . . ?
C13 C14 N3 123.0(14) . . ?
C13 C14 C15 120.1(16) . . ?
N3 C14 C15 116.9(16) . . ?
C16 C15 C14 172(2) . . ?
C15 C16 I4 174.5(17) . . ?
C19 N5 C21 118.7(13) . . ?
C22 N6 C20 119.6(13) . . ?
C18 C17 I5 176.2(17) . . ?
C17 C18 C19 176.7(19) . . ?
N5 C19 C20 122.0(13) . . ?
N5 C19 C18 121.5(13) . . ?
C20 C19 C18 116.4(15) . . ?
N6 C20 C19 117.6(14) . . ?
N6 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
N5 C21 C22 125.1(15) . . ?
N5 C21 H21 117.5 . . ?
C22 C21 H21 117.5 . . ?
N6 C22 C23 118.4(14) . . ?
N6 C22 C21 116.6(13) . . ?
C23 C22 C21 125.0(16) . . ?
C24 C23 C22 174(2) . . ?
C23 C24 I6 173.7(18) . . ?
C29 N7 C27 119.8(14) . . ?
C28 N8 C30 117.6(13) . . ?
C26 C25 I8 173.2(15) . . ?
C25 C26 C27 175.8(16) . . ?
N7 C27 C28 120.7(13) . . ?
N7 C27 C26 119.7(12) . . ?
C28 C27 C26 119.5(13) . . ?
N8 C28 C27 120.3(14) . . ?
N8 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
N7 C29 C30 124.5(15) . . ?
N7 C29 H29 117.8 . . ?
C30 C29 H29 117.8 . . ?
N8 C30 C31 118.5(13) . . ?
N8 C30 C29 116.8(14) . . ?
C31 C30 C29 124.7(14) . . ?
C32 C31 C30 176.3(18) . . ?
C31 C32 I7 175.6(16) . . ?

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
C5 N1 C3 C4 0(2) . . . . ?
C5 N1 C3 C2 -178(2) . . . . ?
N1 C3 C4 N2 -3(3) . . . . ?
C2 C3 C4 N2 174.7(18) . . . . ?
C6 N2 C4 C3 5(3) . . . . ?
C3 N1 C5 C6 1(3) . . . . ?
C4 N2 C6 C5 -4(2) . . . . ?
C4 N2 C6 C7 177.9(16) . . . . ?
N1 C5 C6 N2 1(3) . . . . ?
N1 C5 C6 C7 180(2) . . . . ?
C13 N4 C11 C10 -179.5(18) . . . . ?
C13 N4 C11 C12 4(3) . . . . ?
C14 N3 C12 C11 1(2) . . . . ?
N4 C11 C12 N3 -4(3) . . . . ?
C10 C11 C12 N3 179.3(18) . . . . ?
C11 N4 C13 C14 -2(3) . . . . ?
N4 C13 C14 N3 0(3) . . . . ?
N4 C13 C14 C15 -177.6(17) . . . . ?
C12 N3 C14 C13 0(3) . . . . ?
C12 N3 C14 C15 177.8(16) . . . . ?
C21 N5 C19 C20 -2(3) . . . . ?
C21 N5 C19 C18 176.1(16) . . . . ?
C22 N6 C20 C19 5(2) . . . . ?
N5 C19 C20 N6 -3(2) . . . . ?
C18 C19 C20 N6 178.0(16) . . . . ?
C19 N5 C21 C22 7(3) . . . . ?
C20 N6 C22 C23 178.2(17) . . . . ?
C20 N6 C22 C21 -2(3) . . . . ?
N5 C21 C22 N6 -4(3) . . . . ?
N5 C21 C22 C23 175.5(19) . . . . ?
C29 N7 C27 C28 3(3) . . . . ?
C29 N7 C27 C26 -179.9(16) . . . . ?
C30 N8 C28 C27 -2(3) . . . . ?
N7 C27 C28 N8 -1(3) . . . . ?
C26 C27 C28 N8 -177.4(18) . . . . ?
C27 N7 C29 C30 -3(3) . . . . ?
C28 N8 C30 C31 -174.8(16) . . . . ?
C28 N8 C30 C29 3(2) . . . . ?
N7 C29 C30 N8 0(3) . . . . ?
N7 C29 C30 C31 177.1(19) . . . . ?

_refine_diff_density_max         1.041
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.147



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_L2a
_database_code_depnum_ccdc_archive 'CCDC 1861308'
_audit_update_record             
;
2019-01-07 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H2 I2 N2, 0.6(C2 H3 N)'
_chemical_formula_sum            'C9.20 H3.80 I2 N2.60'
_chemical_formula_weight         404.55

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.3229(14)
_cell_length_b                   13.047(4)
_cell_length_c                   29.586(9)
_cell_angle_alpha                90.190(8)
_cell_angle_beta                 91.770(8)
_cell_angle_gamma                95.024(8)
_cell_volume                     1661.4(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    205
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.426
_exptl_crystal_F_000             1099
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    5.641
_shelx_estimated_absorpt_T_min   0.211
_shelx_estimated_absorpt_T_max   0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4459
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39069
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5978
_reflns_number_gt                4910
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+69.0584P] 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         5978
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.207
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.009 0.180 0.106 54 16 ' '
2 -0.070 0.000 0.500 117 43 ' '
3 -0.080 0.820 0.894 54 16 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 1 0 1.567
1 2 0 5.909
0 -1 1 1.708
0 0 1 0.689
0 1 1 1.715
0 -1 2 2.080
0 0 2 1.377
0 1 2 2.093
0 0 3 2.066
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Structural refinement of Q-peaks from the residual electron density as solvent 
molecules were unsuccessful. The data was then processed with the SQUEEZE procedure: 
Spek, A. L. Acta Cryst. 2015, C71, 9-18. 75 electrons in the solvent-assesible void , which corresponded to 3.4 acetonitrile molecules, were found in the unit cell and has been removed by SQUEEZE procedure.

;
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
I3 I -0.0160(3) 0.69804(10) 0.52654(4) 0.0472(3) Uani 1 1 d . . . . .
C3 C 0.469(4) 0.1075(13) 0.3440(6) 0.038(4) Uani 1 1 d . . . . .
I4 I 0.0886(4) 0.71732(12) 0.18052(5) 0.0606(4) Uani 1 1 d . . . . .
C4 C 0.389(4) 0.1479(13) 0.3864(6) 0.043(4) Uani 1 1 d . . . . .
H4 H 0.461266 0.117894 0.412720 0.051 Uiso 1 1 calc R U . . .
I1 I 0.9781(3) -0.18751(10) 0.34590(6) 0.0661(5) Uani 1 1 d . . . . .
N1 N 0.221(4) 0.2244(12) 0.3900(5) 0.051(4) Uani 1 1 d . . . . .
C1 C 0.786(5) -0.0525(14) 0.3433(8) 0.057(6) Uani 1 1 d . . . . .
I2 I -0.1727(4) 0.39308(15) 0.18524(5) 0.0762(5) Uani 1 1 d . . . . .
N2 N 0.375(3) 0.1502(10) 0.3051(5) 0.035(3) Uani 1 1 d . . . . .
C2 C 0.644(4) 0.0211(13) 0.3418(6) 0.041(4) Uani 1 1 d . . . . .
N3 N 0.656(4) 0.4582(11) 0.3582(5) 0.043(4) Uani 1 1 d . . . . .
N4 N 0.271(3) 0.6182(10) 0.3541(5) 0.037(3) Uani 1 1 d . . . . .
N5 N 0.917(4) 0.8014(14) 0.0914(5) 0.054(4) Uani 1 1 d . . . . .
I5 I 1.4245(4) 0.44928(14) 0.06778(6) 0.0782(5) Uani 1 1 d . . . . .
C5 C 0.129(4) 0.2684(14) 0.3512(6) 0.045(4) Uani 1 1 d . . . . .
H5 H 0.009186 0.324131 0.352534 0.054 Uiso 1 1 calc R U . . .
N6 N 0.753(6) 0.8785(19) 0.0064(6) 0.092(7) Uani 1 1 d . . . . .
I6 I 0.5103(4) 1.05095(12) 0.21765(5) 0.0640(4) Uani 1 1 d . . . . .
C6 C 0.211(3) 0.2317(11) 0.3087(6) 0.033(4) Uani 1 1 d . . . . .
C7 C 0.094(4) 0.2785(14) 0.2694(6) 0.042(4) Uani 1 1 d . . . . .
C8 C 0.002(5) 0.3227(16) 0.2389(7) 0.053(5) Uani 1 1 d . . . . .
C9 C 0.131(5) 0.6443(18) 0.4685(6) 0.055(6) Uani 1 1 d . . . . .
C10 C 0.236(5) 0.6177(16) 0.4332(6) 0.050(5) Uani 1 1 d . . . . .
C11 C 0.361(4) 0.5796(12) 0.3928(6) 0.034(4) Uani 1 1 d . . . . .
C12 C 0.542(4) 0.4977(12) 0.3949(6) 0.038(4) Uani 1 1 d . . . . .
H12 H 0.585474 0.469242 0.422916 0.046 Uiso 1 1 calc R U . . .
C15 C 0.290(4) 0.6183(15) 0.2737(6) 0.046(5) Uani 1 1 d . . . . .
C14 C 0.382(4) 0.5785(13) 0.3164(5) 0.036(4) Uani 1 1 d . . . . .
C13 C 0.576(4) 0.5004(14) 0.3191(6) 0.041(4) Uani 1 1 d . . . . .
H13 H 0.654559 0.476092 0.292567 0.049 Uiso 1 1 calc R U . . .
C16 C 0.227(5) 0.6565(18) 0.2387(6) 0.057(5) Uani 1 1 d . . . . .
C23 C 0.686(6) 0.9412(17) 0.1270(7) 0.066(6) Uani 1 1 d . . . . .
C24 C 0.632(6) 0.9839(18) 0.1597(8) 0.072(7) Uani 1 1 d . . . . .
C22 C 0.771(5) 0.8907(15) 0.0860(6) 0.048(5) Uani 1 1 d . . . . .
C21 C 0.686(7) 0.9246(19) 0.0435(8) 0.081(8) Uani 1 1 d . . . . .
H21 H 0.577199 0.982817 0.041294 0.097 Uiso 1 1 calc R U . . .
C20 C 0.923(5) 0.801(2) 0.0109(8) 0.068(7) Uani 1 1 d . . . . .
H20 H 1.009816 0.774405 -0.014628 0.082 Uiso 1 1 calc R U . . .
C19 C 0.980(5) 0.7555(16) 0.0534(7) 0.057(5) Uani 1 1 d . . . . .
C18 C 1.151(6) 0.666(2) 0.0569(7) 0.066(6) Uani 1 1 d . . . . .
C17 C 1.252(5) 0.5855(18) 0.0602(8) 0.065(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I3 C9 1.996(18) . ?
C3 N2 1.35(2) . ?
C3 C2 1.41(2) . ?
C3 C4 1.42(2) . ?
I4 C16 2.00(2) . ?
C4 N1 1.29(2) . ?
C4 H4 0.9300 . ?
I1 C1 2.01(2) . ?
N1 C5 1.35(2) . ?
C1 C2 1.18(2) . ?
I2 C8 2.00(2) . ?
N2 C6 1.33(2) . ?
N3 C12 1.33(2) . ?
N3 C13 1.33(2) . ?
N4 C11 1.31(2) . ?
N4 C14 1.35(2) . ?
N5 C19 1.32(2) . ?
N5 C22 1.38(3) . ?
I5 C17 2.00(3) . ?
C5 C6 1.41(2) . ?
C5 H5 0.9300 . ?
N6 C21 1.30(3) . ?
N6 C20 1.31(3) . ?
I6 C24 2.03(2) . ?
C6 C7 1.42(3) . ?
C7 C8 1.15(3) . ?
C9 C10 1.21(2) . ?
C10 C11 1.43(2) . ?
C11 C12 1.38(2) . ?
C12 H12 0.9300 . ?
C15 C16 1.18(3) . ?
C15 C14 1.43(2) . ?
C14 C13 1.38(2) . ?
C13 H13 0.9300 . ?
C23 C24 1.16(3) . ?
C23 C22 1.45(3) . ?
C22 C21 1.39(3) . ?
C21 H21 0.9300 . ?
C20 C19 1.41(3) . ?
C20 H20 0.9300 . ?
C19 C18 1.44(3) . ?
C18 C17 1.17(3) . ?

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
N2 C3 C2 118.8(16) . . ?
N2 C3 C4 120.4(14) . . ?
C2 C3 C4 120.8(17) . . ?
N1 C4 C3 122.9(16) . . ?
N1 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 N1 C5 117.0(16) . . ?
C2 C1 I1 173.1(17) . . ?
C6 N2 C3 116.8(14) . . ?
C1 C2 C3 175(2) . . ?
C12 N3 C13 115.7(14) . . ?
C11 N4 C14 116.6(14) . . ?
C19 N5 C22 115.0(17) . . ?
N1 C5 C6 121.3(17) . . ?
N1 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C21 N6 C20 117(2) . . ?
N2 C6 C5 121.5(16) . . ?
N2 C6 C7 120.1(16) . . ?
C5 C6 C7 118.2(16) . . ?
C8 C7 C6 175(2) . . ?
C7 C8 I2 177.2(19) . . ?
C10 C9 I3 175(2) . . ?
C9 C10 C11 176(2) . . ?
N4 C11 C12 122.1(15) . . ?
N4 C11 C10 117.6(15) . . ?
C12 C11 C10 119.9(16) . . ?
N3 C12 C11 122.1(16) . . ?
N3 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C16 C15 C14 176(2) . . ?
N4 C14 C13 120.7(15) . . ?
N4 C14 C15 118.3(15) . . ?
C13 C14 C15 120.9(16) . . ?
N3 C13 C14 122.6(15) . . ?
N3 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C15 C16 I4 175.7(19) . . ?
C24 C23 C22 177(3) . . ?
C23 C24 I6 176(3) . . ?
N5 C22 C21 121.0(18) . . ?
N5 C22 C23 116.8(16) . . ?
C21 C22 C23 122(2) . . ?
N6 C21 C22 123(2) . . ?
N6 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
N6 C20 C19 122(2) . . ?
N6 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
N5 C19 C20 121(2) . . ?
N5 C19 C18 117.3(18) . . ?
C20 C19 C18 121(2) . . ?
C17 C18 C19 171(3) . . ?
C18 C17 I5 178(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C3 C4 N1 1(3) . . . . ?
C2 C3 C4 N1 -177.5(18) . . . . ?
C3 C4 N1 C5 -2(3) . . . . ?
C2 C3 N2 C6 -179.9(14) . . . . ?
C4 C3 N2 C6 1(2) . . . . ?
C4 N1 C5 C6 1(3) . . . . ?
C3 N2 C6 C5 -3(2) . . . . ?
C3 N2 C6 C7 -177.7(15) . . . . ?
N1 C5 C6 N2 2(3) . . . . ?
N1 C5 C6 C7 177.0(17) . . . . ?
C14 N4 C11 C12 -4(2) . . . . ?
C14 N4 C11 C10 -177.5(16) . . . . ?
C13 N3 C12 C11 -2(3) . . . . ?
N4 C11 C12 N3 5(3) . . . . ?
C10 C11 C12 N3 178.3(17) . . . . ?
C11 N4 C14 C13 1(2) . . . . ?
C11 N4 C14 C15 179.9(16) . . . . ?
C12 N3 C13 C14 -1(3) . . . . ?
N4 C14 C13 N3 2(3) . . . . ?
C15 C14 C13 N3 -176.9(17) . . . . ?
C19 N5 C22 C21 3(3) . . . . ?
C19 N5 C22 C23 177(2) . . . . ?
C20 N6 C21 C22 -4(4) . . . . ?
N5 C22 C21 N6 -4(4) . . . . ?
C23 C22 C21 N6 -178(3) . . . . ?
C21 N6 C20 C19 13(4) . . . . ?
C22 N5 C19 C20 5(3) . . . . ?
C22 N5 C19 C18 175.9(19) . . . . ?
N6 C20 C19 N5 -14(4) . . . . ?
N6 C20 C19 C18 176(2) . . . . ?

_refine_diff_density_max         3.766
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.233



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_L2b
_database_code_depnum_ccdc_archive 'CCDC 1861309'
_audit_update_record             
;
2019-01-07 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H2 I2 N2, C7 H8'
_chemical_formula_sum            'C10 H5 I2 N3'
_chemical_formula_weight         420.97

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.2425(6)
_cell_length_b                   23.537(4)
_cell_length_c                   24.567(4)
_cell_angle_alpha                111.725(5)
_cell_angle_beta                 94.131(5)
_cell_angle_gamma                93.861(5)
_cell_volume                     2261.3(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    351
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.149
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            74965
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8134
_reflns_number_gt                6136
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1465P)²+34.9151P] 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         8134
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.1002
_refine_ls_wR_factor_ref         0.2690
_refine_ls_wR_factor_gt          0.2535
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.044 0.000 0.000 123 26 ' '
2 -0.032 0.000 0.500 112 30 ' '
3 -0.039 0.500 1.000 570 209 ' '
4 0.009 0.500 0.500 109 30 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 1 0 0.936
0 2 0 1.872
0 -2 1 1.745
0 -1 1 1.024
0 0 1 0.897
0 1 1 1.521
0 -2 2 2.048
0 -1 2 1.682
0 0 2 1.794
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Structural refinement of Q-peaks from the residual electron density as solvent 
molecules were unsuccessful. The data was then processed with the SQUEEZE procedure: 
Spek, A. L. Acta Cryst. 2015, C71, 9-18. 295 electrons in the solvent-assesible void , which corresponded to 6 toluene molecules, were found in the unit cell and has been removed by SQUEEZE procedure.

;
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 1.4985(3) 0.16121(6) 0.96082(4) 0.0695(4) Uani 1 1 d . . . . .
C1 C 1.274(4) 0.1262(9) 0.8777(9) 0.072(5) Uani 1 1 d . . . . .
I2 I 1.1209(3) -0.18267(5) 0.54906(5) 0.0671(4) Uani 1 1 d . . . . .
C2 C 1.140(4) 0.1055(7) 0.8307(6) 0.057(4) Uani 1 1 d . . . . .
N1 N 0.645(3) 0.0974(5) 0.6990(5) 0.052(3) Uani 1 1 d . . . . .
N2 N 1.048(3) 0.0248(5) 0.7352(5) 0.049(3) Uani 1 1 d . . . . .
C3 C 0.987(3) 0.0821(6) 0.7709(6) 0.045(3) Uani 1 1 d . . . . .
C4 C 0.786(4) 0.1174(7) 0.7547(7) 0.055(4) Uani 1 1 d . . . . .
H4 H 0.746875 0.155244 0.782126 0.066 Uiso 1 1 calc R U . . .
I4 I 0.2398(3) 0.28401(6) 0.32605(5) 0.0687(4) Uani 1 1 d . . . . .
C5 C 0.701(4) 0.0414(7) 0.6617(7) 0.058(4) Uani 1 1 d . . . . .
H5 H 0.604840 0.025823 0.623192 0.070 Uiso 1 1 calc R U . . .
C6 C 0.904(3) 0.0070(7) 0.6808(7) 0.051(3) Uani 1 1 d . . . . .
I6 I 1.6270(3) 0.06426(6) 0.22609(7) 0.0786(4) Uani 1 1 d . . . . .
I3 I 1.3482(3) 0.18345(5) 0.65988(5) 0.0627(3) Uani 1 1 d . . . . .
C7 C 0.973(4) -0.0518(7) 0.6401(7) 0.063(4) Uani 1 1 d . . . . .
N3 N 0.747(3) 0.3013(5) 0.5396(5) 0.047(3) Uani 1 1 d . . . . .
N4 N 0.585(3) 0.4109(6) 0.6208(6) 0.065(4) Uani 1 1 d . . . . .
C9 C 1.148(4) 0.2462(8) 0.6347(8) 0.065(4) Uani 1 1 d . . . . .
C8 C 1.023(4) -0.0993(7) 0.6078(7) 0.061(4) Uani 1 1 d . . . . .
C10 C 1.002(4) 0.2803(7) 0.6163(8) 0.060(4) Uani 1 1 d . . . . .
C11 C 0.847(3) 0.3199(5) 0.5973(6) 0.043(3) Uani 1 1 d . . . . .
C12 C 0.764(4) 0.3745(8) 0.6376(7) 0.064(4) Uani 1 1 d . . . . .
H12 H 0.835172 0.386112 0.677231 0.077 Uiso 1 1 calc R U . . .
C14 C 0.579(4) 0.3398(6) 0.5228(6) 0.048(3) Uani 1 1 d . . . . .
C13 C 0.500(4) 0.3938(7) 0.5649(7) 0.058(4) Uani 1 1 d . . . . .
H13 H 0.379536 0.419073 0.552220 0.070 Uiso 1 1 calc R U . . .
C16 C 0.383(3) 0.3079(7) 0.4118(7) 0.057(4) Uani 1 1 d . . . . .
C15 C 0.480(4) 0.3224(7) 0.4627(7) 0.058(4) Uani 1 1 d . . . . .
I5 I 0.5852(3) 0.47100(5) 0.29954(5) 0.0702(4) Uani 1 1 d . . . . .
N5 N 1.037(3) 0.2485(5) 0.1976(5) 0.049(3) Uani 1 1 d . . . . .
N6 N 0.800(4) 0.2074(7) 0.0793(6) 0.071(4) Uani 1 1 d . . . . .
C17 C 0.719(4) 0.3889(7) 0.2465(9) 0.065(4) Uani 1 1 d . . . . .
C18 C 0.786(4) 0.3407(7) 0.2162(7) 0.061(4) Uani 1 1 d . . . . .
C20 C 0.749(4) 0.2614(8) 0.1171(7) 0.062(4) Uani 1 1 d . . . . .
H20 H 0.638188 0.286913 0.103324 0.075 Uiso 1 1 calc R U . . .
C19 C 0.854(3) 0.2827(7) 0.1776(6) 0.048(3) Uani 1 1 d . . . . .
C23 C 1.275(4) 0.1555(6) 0.1795(7) 0.053(4) Uani 1 1 d . . . . .
C21 C 0.977(5) 0.1736(9) 0.0993(8) 0.069(5) Uani 1 1 d . . . . .
H21 H 1.021632 0.135396 0.073403 0.083 Uiso 1 1 calc R U . . .
C24 C 1.416(4) 0.1239(8) 0.1964(8) 0.062(4) Uani 1 1 d . . . . .
C22 C 1.099(3) 0.1943(6) 0.1591(6) 0.041(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.03(2) . ?
C1 C2 1.16(2) . ?
I2 C8 2.050(16) . ?
C2 C3 1.449(19) . ?
N1 C5 1.346(19) . ?
N1 C4 1.35(2) . ?
N2 C6 1.329(19) . ?
N2 C3 1.363(17) . ?
C3 C4 1.37(2) . ?
C4 H4 0.9300 . ?
I4 C16 2.004(17) . ?
C5 C6 1.39(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.44(2) . ?
I6 C24 2.033(17) . ?
I3 C9 2.012(17) . ?
C7 C8 1.15(2) . ?
N3 C11 1.346(18) . ?
N3 C14 1.351(18) . ?
N4 C13 1.30(2) . ?
N4 C12 1.33(2) . ?
C9 C10 1.24(2) . ?
C10 C11 1.37(2) . ?
C11 C12 1.39(2) . ?
C12 H12 0.9300 . ?
C14 C13 1.39(2) . ?
C14 C15 1.40(2) . ?
C13 H13 0.9300 . ?
C16 C15 1.20(2) . ?
I5 C17 2.036(16) . ?
N5 C22 1.335(18) . ?
N5 C19 1.345(18) . ?
N6 C20 1.31(2) . ?
N6 C21 1.33(2) . ?
C17 C18 1.17(2) . ?
C18 C19 1.41(2) . ?
C20 C19 1.41(2) . ?
C20 H20 0.9300 . ?
C23 C24 1.16(2) . ?
C23 C22 1.42(2) . ?
C21 C22 1.41(2) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 178.3(18) . . ?
C1 C2 C3 176(2) . . ?
C5 N1 C4 117.5(12) . . ?
C6 N2 C3 113.2(12) . . ?
N2 C3 C4 124.7(13) . . ?
N2 C3 C2 116.8(12) . . ?
C4 C3 C2 118.5(13) . . ?
N1 C4 C3 119.9(14) . . ?
N1 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C6 120.1(14) . . ?
N1 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
N2 C6 C5 124.4(14) . . ?
N2 C6 C7 115.8(13) . . ?
C5 C6 C7 119.8(14) . . ?
C8 C7 C6 179(2) . . ?
C11 N3 C14 116.8(12) . . ?
C13 N4 C12 117.1(14) . . ?
C10 C9 I3 173.8(15) . . ?
C7 C8 I2 178.5(17) . . ?
C9 C10 C11 177.9(19) . . ?
N3 C11 C10 118.1(13) . . ?
N3 C11 C12 121.0(13) . . ?
C10 C11 C12 120.5(14) . . ?
N4 C12 C11 121.7(15) . . ?
N4 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
N3 C14 C13 120.0(14) . . ?
N3 C14 C15 118.0(12) . . ?
C13 C14 C15 122.0(13) . . ?
N4 C13 C14 123.4(14) . . ?
N4 C13 H13 118.3 . . ?
C14 C13 H13 118.3 . . ?
C15 C16 I4 177.5(15) . . ?
C16 C15 C14 177.3(18) . . ?
C22 N5 C19 117.9(12) . . ?
C20 N6 C21 117.1(14) . . ?
C18 C17 I5 177.6(17) . . ?
C17 C18 C19 177.1(19) . . ?
N6 C20 C19 123.4(15) . . ?
N6 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
N5 C19 C20 119.1(13) . . ?
N5 C19 C18 120.2(13) . . ?
C20 C19 C18 120.6(14) . . ?
C24 C23 C22 179.2(18) . . ?
N6 C21 C22 121.4(15) . . ?
N6 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C24 I6 175.2(14) . . ?
N5 C22 C21 120.9(13) . . ?
N5 C22 C23 119.3(12) . . ?
C21 C22 C23 119.7(14) . . ?

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
C6 N2 C3 C4 3(2) . . . . ?
C6 N2 C3 C2 -179.0(14) . . . . ?
C5 N1 C4 C3 2(2) . . . . ?
N2 C3 C4 N1 -4(2) . . . . ?
C2 C3 C4 N1 178.8(14) . . . . ?
C4 N1 C5 C6 -1(2) . . . . ?
C3 N2 C6 C5 -2(2) . . . . ?
C3 N2 C6 C7 176.7(14) . . . . ?
N1 C5 C6 N2 1(3) . . . . ?
N1 C5 C6 C7 -177.6(15) . . . . ?
C14 N3 C11 C10 176.2(14) . . . . ?
C14 N3 C11 C12 4(2) . . . . ?
C13 N4 C12 C11 -2(3) . . . . ?
N3 C11 C12 N4 -1(2) . . . . ?
C10 C11 C12 N4 -173.0(16) . . . . ?
C11 N3 C14 C13 -4(2) . . . . ?
C11 N3 C14 C15 178.1(14) . . . . ?
C12 N4 C13 C14 2(3) . . . . ?
N3 C14 C13 N4 2(3) . . . . ?
C15 C14 C13 N4 179.4(17) . . . . ?
C21 N6 C20 C19 -4(3) . . . . ?
C22 N5 C19 C20 -3(2) . . . . ?
C22 N5 C19 C18 -179.0(14) . . . . ?
N6 C20 C19 N5 5(3) . . . . ?
N6 C20 C19 C18 -178.6(17) . . . . ?
C20 N6 C21 C22 1(3) . . . . ?
C19 N5 C22 C21 0(2) . . . . ?
C19 N5 C22 C23 -176.3(13) . . . . ?
N6 C21 C22 N5 1(3) . . . . ?
N6 C21 C22 C23 177.0(16) . . . . ?

_refine_diff_density_max         4.048
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.284



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_L2c
_database_code_depnum_ccdc_archive 'CCDC 1861310'
_audit_update_record             
;
2018-12-24 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H0 I2 N2'
_chemical_formula_weight         377.90

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.9441(6)
_cell_length_b                   35.2209(15)
_cell_length_c                   8.2173(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.3310(10)
_cell_angle_gamma                90
_cell_volume                     4035.6(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    872
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.488
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    6.181
_shelx_estimated_absorpt_T_min   0.259
_shelx_estimated_absorpt_T_max   0.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4264
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            79182
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7304
_reflns_number_gt                6645
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0293P)²+34.3665P] 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         7304
_refine_ls_number_parameters     443
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.002

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 1.20119(3) -0.00578(2) 0.93570(5) 0.03534(12) Uani 1 1 d . . . . .
N1 N 0.0772(4) 0.25292(16) 0.3801(7) 0.0323(12) Uani 1 1 d . . . . .
I6 I 0.63907(3) 0.14269(2) 0.35946(6) 0.03855(12) Uani 1 1 d . . . . .
N6 N 0.4702(4) 0.02370(18) 0.6650(8) 0.0417(15) Uani 1 1 d . . . . .
N5 N 0.6266(4) 0.01497(15) 0.8765(6) 0.0273(11) Uani 1 1 d . . . . .
C38 C 0.7882(4) 0.03171(17) 0.5240(7) 0.0236(12) Uani 1 1 d . . . . .
C39 C 0.7429(5) 0.06559(19) 0.4641(8) 0.0299(14) Uani 1 1 d . . . . .
C40 C 0.7032(5) 0.09338(19) 0.4191(9) 0.0337(15) Uani 1 1 d . . . . .
C42 C 0.7441(5) -0.00324(19) 0.5051(8) 0.0312(14) Uani 1 1 d . . . . .
H42 H 0.683173 -0.004383 0.452955 0.037 Uiso 1 1 calc R U . . .
C43 C 0.9135(4) 0.00291(18) 0.6537(7) 0.0260(13) Uani 1 1 d . . . . .
C63 C 0.8676(5) -0.03189(19) 0.6328(8) 0.0342(15) Uani 1 1 d . . . . .
H63 H 0.897516 -0.054130 0.674367 0.041 Uiso 1 1 calc R U . . .
C64 C 1.0042(5) 0.0039(2) 0.7371(8) 0.0347(15) Uani 1 1 d . . . . .
C65 C 1.0764(5) 0.0001(2) 0.8107(8) 0.0350(15) Uani 1 1 d . . . . .
I3 I 0.30147(3) 0.10749(2) 0.46895(6) 0.03345(11) Uani 1 1 d . . . . .
N3 N 0.4603(4) 0.28874(15) 0.3665(7) 0.0322(12) Uani 1 1 d . . . . .
I7 I 0.88893(3) 0.24797(2) 0.03423(5) 0.03201(11) Uani 1 1 d . . . . .
N7 N 0.7841(4) -0.03519(16) 0.5575(7) 0.0353(13) Uani 1 1 d . . . . .
C1 C 0.7563(5) 0.24819(19) 0.1293(8) 0.0315(14) Uani 1 1 d . . . . .
C2 C 0.6791(5) 0.24774(18) 0.1868(8) 0.0313(14) Uani 1 1 d . . . . .
N2 N 0.2348(4) 0.2483(2) 0.1740(8) 0.0480(17) Uani 1 1 d . . . . .
C76 C 0.0705(8) 0.3516(2) 0.4314(11) 0.060(2) Uani 1 1 d D . . . .
I12 I 0.02664(17) 0.40419(7) 0.5112(3) 0.0558(13) Uani 0.470(13) 1 d D . P A 1
I12A I 0.0639(12) 0.40347(10) 0.4891(8) 0.209(3) Uani 0.530(13) 1 d D . P A 2
C3 C 0.5864(4) 0.24972(18) 0.2638(8) 0.0264(13) Uani 1 1 d . . . . .
C4 C 0.5438(5) 0.28483(19) 0.2878(8) 0.0330(15) Uani 1 1 d . . . . .
H4 H 0.574777 0.306869 0.247120 0.040 Uiso 1 1 calc R U . . .
N4 N 0.5438(3) 0.21753(14) 0.3092(6) 0.0254(11) Uani 1 1 d . . . . .
C6 C 0.4186(4) 0.25664(18) 0.4145(8) 0.0272(13) Uani 1 1 d . . . . .
H6 H 0.359548 0.258025 0.471281 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4585(4) 0.22123(17) 0.3843(8) 0.0261(13) Uani 1 1 d . . . . .
C55 C 0.3668(5) 0.15826(18) 0.4534(8) 0.0303(14) Uani 1 1 d . . . . .
C56 C 0.4089(4) 0.18710(18) 0.4269(8) 0.0305(14) Uani 1 1 d . . . . .
I8 I 0.58496(3) -0.13664(2) 1.03473(6) 0.03723(12) Uani 1 1 d . . . . .
N8 N 0.8742(4) 0.03527(14) 0.5987(6) 0.0258(11) Uani 1 1 d . . . . .
I14 I 0.78400(5) 0.15619(2) 0.90276(8) 0.05930(17) Uani 1 1 d . . . . .
C66 C 0.5872(5) -0.05112(19) 0.9075(8) 0.0334(15) Uani 1 1 d . . . . .
C67 C 0.5908(5) -0.0824(2) 0.9565(8) 0.0377(16) Uani 1 1 d . . . . .
C68 C 0.4914(5) -0.0095(2) 0.7325(9) 0.0378(16) Uani 1 1 d . . . . .
H68 H 0.452225 -0.030842 0.708260 0.045 Uiso 1 1 calc R U . . .
C70 C 0.5268(5) 0.0527(2) 0.7010(8) 0.0335(15) Uani 1 1 d . . . . .
H70 H 0.514354 0.076769 0.653381 0.040 Uiso 1 1 calc R U . . .
C71 C 0.6051(4) 0.04857(18) 0.8085(8) 0.0269(13) Uani 1 1 d . . . . .
C72 C 0.6634(5) 0.08071(19) 0.8466(8) 0.0327(15) Uani 1 1 d . . . . .
C73 C 0.7076(5) 0.1088(2) 0.8684(9) 0.0396(17) Uani 1 1 d . . . . .
C79 C 0.5693(5) -0.01411(18) 0.8378(8) 0.0293(14) Uani 1 1 d . . . . .
I11 I -0.03309(4) 0.10988(2) 0.52000(6) 0.04362(13) Uani 1 1 d . . . . .
C18 C 0.0309(5) 0.1574(2) 0.4381(10) 0.0439(18) Uani 1 1 d . . . . .
C20 C 0.0673(5) 0.1856(2) 0.3894(10) 0.0384(17) Uani 1 1 d . . . . .
C21 C 0.1122(4) 0.21954(19) 0.3326(8) 0.0303(14) Uani 1 1 d . . . . .
C29 C 0.0901(6) 0.3207(2) 0.3833(10) 0.0467(19) Uani 1 1 d . . . . .
C30 C 0.1218(5) 0.2845(2) 0.3270(9) 0.0368(16) Uani 1 1 d . . . . .
C31 C 0.2005(5) 0.2816(2) 0.2226(9) 0.0447(19) Uani 1 1 d . . . . .
H31 H 0.230352 0.304254 0.185401 0.054 Uiso 1 1 calc R U . . .
C32 C 0.1915(5) 0.2175(2) 0.2296(8) 0.0376(16) Uani 1 1 d . . . . .
H32 H 0.215117 0.193263 0.198521 0.045 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 C65 2.027(7) . ?
N1 C21 1.333(9) . ?
N1 C30 1.347(9) . ?
I6 C40 2.012(6) . ?
N6 C70 1.323(9) . ?
N6 C68 1.327(9) . ?
N5 C79 1.336(8) . ?
N5 C71 1.342(8) . ?
C38 N8 1.351(8) . ?
C38 C42 1.384(9) . ?
C38 C39 1.435(9) . ?
C39 C40 1.183(9) . ?
C42 N7 1.327(9) . ?
C42 H42 0.9500 . ?
C43 N8 1.342(8) . ?
C43 C63 1.393(9) . ?
C43 C64 1.435(9) . ?
C63 N7 1.320(9) . ?
C63 H63 0.9500 . ?
C64 C65 1.178(9) . ?
I3 C55 2.011(7) . ?
N3 C6 1.332(8) . ?
N3 C4 1.342(9) . ?
I7 C1 2.012(7) . ?
C1 C2 1.178(9) . ?
C2 C3 1.445(9) . ?
N2 C32 1.324(10) . ?
N2 C31 1.330(11) . ?
C76 C29 1.192(12) . ?
C76 I12A 1.889(9) . ?
C76 I12 2.059(9) . ?
C3 N4 1.334(8) . ?
C3 C4 1.386(9) . ?
C4 H4 0.9500 . ?
N4 C7 1.350(8) . ?
C6 C7 1.389(9) . ?
C6 H6 0.9500 . ?
C7 C56 1.431(9) . ?
C55 C56 1.194(9) . ?
I8 C67 2.019(7) . ?
I14 C73 2.000(7) . ?
C66 C67 1.173(10) . ?
C66 C79 1.445(9) . ?
C68 C79 1.394(9) . ?
C68 H68 0.9500 . ?
C70 C71 1.408(9) . ?
C70 H70 0.9500 . ?
C71 C72 1.427(9) . ?
C72 C73 1.178(10) . ?
I11 C18 2.014(8) . ?
C18 C20 1.187(10) . ?
C20 C21 1.429(10) . ?
C21 C32 1.398(9) . ?
C29 C30 1.428(11) . ?
C30 C31 1.400(10) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N1 C30 117.5(6) . . ?
C70 N6 C68 117.0(6) . . ?
C79 N5 C71 116.4(5) . . ?
N8 C38 C42 121.8(6) . . ?
N8 C38 C39 117.8(5) . . ?
C42 C38 C39 120.5(6) . . ?
C40 C39 C38 177.6(7) . . ?
C39 C40 I6 175.3(6) . . ?
N7 C42 C38 122.2(6) . . ?
N7 C42 H42 118.9 . . ?
C38 C42 H42 118.9 . . ?
N8 C43 C63 121.3(6) . . ?
N8 C43 C64 119.9(6) . . ?
C63 C43 C64 118.8(6) . . ?
N7 C63 C43 122.6(6) . . ?
N7 C63 H63 118.7 . . ?
C43 C63 H63 118.7 . . ?
C65 C64 C43 171.8(8) . . ?
C64 C65 I1 179.2(7) . . ?
C6 N3 C4 115.9(6) . . ?
C63 N7 C42 116.4(6) . . ?
C2 C1 I7 178.7(7) . . ?
C1 C2 C3 175.8(7) . . ?
C32 N2 C31 117.1(6) . . ?
C29 C76 I12A 168.3(11) . . ?
C29 C76 I12 175.9(9) . . ?
N4 C3 C4 121.8(6) . . ?
N4 C3 C2 118.8(6) . . ?
C4 C3 C2 119.4(6) . . ?
N3 C4 C3 122.2(6) . . ?
N3 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C3 N4 C7 116.1(5) . . ?
N3 C6 C7 122.2(6) . . ?
N3 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
N4 C7 C6 121.6(5) . . ?
N4 C7 C56 117.3(6) . . ?
C6 C7 C56 121.1(6) . . ?
C56 C55 I3 172.5(6) . . ?
C55 C56 C7 176.3(8) . . ?
C43 N8 C38 115.8(5) . . ?
C67 C66 C79 171.7(8) . . ?
C66 C67 I8 175.0(7) . . ?
N6 C68 C79 122.2(6) . . ?
N6 C68 H68 118.9 . . ?
C79 C68 H68 118.9 . . ?
N6 C70 C71 121.4(6) . . ?
N6 C70 H70 119.3 . . ?
C71 C70 H70 119.3 . . ?
N5 C71 C70 121.5(6) . . ?
N5 C71 C72 118.9(6) . . ?
C70 C71 C72 119.6(6) . . ?
C73 C72 C71 174.7(8) . . ?
C72 C73 I14 179.2(7) . . ?
N5 C79 C68 121.4(6) . . ?
N5 C79 C66 119.7(6) . . ?
C68 C79 C66 118.9(6) . . ?
C20 C18 I11 178.9(7) . . ?
C18 C20 C21 179.1(9) . . ?
N1 C21 C32 121.0(6) . . ?
N1 C21 C20 118.6(6) . . ?
C32 C21 C20 120.3(6) . . ?
C76 C29 C30 175.2(9) . . ?
N1 C30 C31 120.4(7) . . ?
N1 C30 C29 119.1(6) . . ?
C31 C30 C29 120.5(7) . . ?
N2 C31 C30 122.1(7) . . ?
N2 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
N2 C32 C21 122.0(7) . . ?
N2 C32 H32 119.0 . . ?
C21 C32 H32 119.0 . . ?

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
N8 C38 C42 N7 -0.7(10) . . . . ?
C39 C38 C42 N7 179.4(6) . . . . ?
N8 C43 C63 N7 0.5(10) . . . . ?
C64 C43 C63 N7 -180.0(6) . . . . ?
C43 C63 N7 C42 -1.6(10) . . . . ?
C38 C42 N7 C63 1.7(10) . . . . ?
C6 N3 C4 C3 -2.7(10) . . . . ?
N4 C3 C4 N3 4.1(11) . . . . ?
C2 C3 C4 N3 -176.3(6) . . . . ?
C4 C3 N4 C7 -2.0(9) . . . . ?
C2 C3 N4 C7 178.3(6) . . . . ?
C4 N3 C6 C7 -0.4(10) . . . . ?
C3 N4 C7 C6 -1.1(9) . . . . ?
C3 N4 C7 C56 176.9(6) . . . . ?
N3 C6 C7 N4 2.3(10) . . . . ?
N3 C6 C7 C56 -175.5(6) . . . . ?
C63 C43 N8 C38 0.5(9) . . . . ?
C64 C43 N8 C38 -179.0(6) . . . . ?
C42 C38 N8 C43 -0.4(9) . . . . ?
C39 C38 N8 C43 179.5(6) . . . . ?
C70 N6 C68 C79 0.4(11) . . . . ?
C68 N6 C70 C71 -1.1(10) . . . . ?
C79 N5 C71 C70 -0.6(9) . . . . ?
C79 N5 C71 C72 179.5(6) . . . . ?
N6 C70 C71 N5 1.3(10) . . . . ?
N6 C70 C71 C72 -178.8(6) . . . . ?
C71 N5 C79 C68 -0.1(9) . . . . ?
C71 N5 C79 C66 -179.3(6) . . . . ?
N6 C68 C79 N5 0.2(11) . . . . ?
N6 C68 C79 C66 179.5(7) . . . . ?
C30 N1 C21 C32 -0.9(9) . . . . ?
C30 N1 C21 C20 179.0(6) . . . . ?
C21 N1 C30 C31 1.5(10) . . . . ?
C21 N1 C30 C29 -176.1(6) . . . . ?
C32 N2 C31 C30 -0.5(11) . . . . ?
N1 C30 C31 N2 -0.9(11) . . . . ?
C29 C30 C31 N2 176.7(7) . . . . ?
C31 N2 C32 C21 1.1(10) . . . . ?
N1 C21 C32 N2 -0.5(10) . . . . ?
C20 C21 C32 N2 179.7(7) . . . . ?

_refine_diff_density_max         2.388
_refine_diff_density_min         -1.958
_refine_diff_density_rms         0.146


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_L1b
_database_code_depnum_ccdc_archive 'CCDC 1861307'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H3 Cl3 I2 N2'
_chemical_formula_weight         499.28

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.3380(10)
_cell_length_b                   18.327(4)
_cell_length_c                   18.018(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.705(7)
_cell_angle_gamma                90
_cell_volume                     1431.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    359
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.316
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    4.927
_shelx_estimated_absorpt_T_min   0.243
_shelx_estimated_absorpt_T_max   0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4704
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15630
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2584
_reflns_number_gt                2150
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0391P)²+88.8798P] 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         2584
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.1024
_refine_ls_wR_factor_ref         0.2683
_refine_ls_wR_factor_gt          0.2611
_refine_ls_goodness_of_fit_ref   1.294
_refine_ls_restrained_S_all      1.294
_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 1.0457(4) 0.54696(9) 0.20452(9) 0.0540(5) Uani 1 1 d . . . . .
N1 N 0.318(4) 0.5227(9) 0.0586(11) 0.045(5) Uani 1 1 d . . . . .
C1 C 0.844(5) 0.3018(14) 0.0034(14) 0.051(6) Uani 1 1 d . . . . .
I2 I 1.0215(4) 0.20000(8) 0.00949(10) 0.0524(5) Uani 1 1 d . . . . .
N2 N 0.691(4) 0.5587(9) 0.4925(11) 0.045(5) Uani 1 1 d . . . . .
C2 C 0.760(6) 0.3609(12) 0.0008(14) 0.048(6) Uani 1 1 d . . . . .
Cl1 Cl 0.469(3) 0.2342(8) 0.1820(6) 0.137(5) Uani 1 1 d . . . . .
Cl2 Cl 0.463(3) 0.2453(8) 0.3370(6) 0.127(4) Uani 1 1 d . . . . .
Cl3 Cl 0.735(4) 0.3583(7) 0.2524(12) 0.186(7) Uani 1 1 d . . . . .
C4 C 0.437(6) 0.4563(12) 0.0569(13) 0.050(6) Uani 1 1 d . . . . .
H4 H 0.3966 0.4239 0.0951 0.060 Uiso 1 1 calc R U . . .
C5 C 0.862(5) 0.5397(12) 0.3061(12) 0.039(5) Uani 1 1 d . . . . .
C6 C 0.756(5) 0.5321(12) 0.3667(13) 0.040(5) Uani 1 1 d . . . . .
C7 C 0.633(5) 0.5166(10) 0.4355(12) 0.037(5) Uani 1 1 d . . . . .
C8 C 0.430(5) 0.4559(12) 0.4430(13) 0.046(6) Uani 1 1 d . . . . .
H8 H 0.3836 0.4265 0.4022 0.055 Uiso 1 1 calc R U . . .
C9 C 0.653(11) 0.2664(18) 0.258(2) 0.109(14) Uani 1 1 d . . . . .
H9 H 0.8521 0.2411 0.2612 0.131 Uiso 1 1 calc R U . . .
C3 C 0.621(5) 0.4336(10) 0.0001(13) 0.042(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C5 2.02(2) . ?
N1 C4 1.32(3) . ?
N1 C3 1.36(3) 3_665 ?
C1 C2 1.14(3) . ?
C1 I2 2.02(2) . ?
N2 C7 1.30(3) . ?
N2 C8 1.32(3) 3_666 ?
C2 C3 1.46(3) . ?
Cl1 C9 1.67(4) . ?
Cl2 C9 1.72(4) . ?
Cl3 C9 1.73(4) . ?
C4 C3 1.38(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.21(3) . ?
C6 C7 1.39(3) . ?
C7 C8 1.43(3) . ?
C8 N2 1.32(3) 3_666 ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C3 N1 1.36(3) 3_665 ?

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
C4 N1 C3 115.9(18) . 3_665 ?
C2 C1 I2 176(2) . . ?
C7 N2 C8 120.1(18) . 3_666 ?
C1 C2 C3 174(3) . . ?
N1 C4 C3 122(2) . . ?
N1 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C6 C5 I1 177(2) . . ?
C5 C6 C7 175(2) . . ?
N2 C7 C6 120.6(19) . . ?
N2 C7 C8 120(2) . . ?
C6 C7 C8 120(2) . . ?
N2 C8 C7 120(2) 3_666 . ?
N2 C8 H8 119.8 3_666 . ?
C7 C8 H8 119.8 . . ?
Cl1 C9 Cl2 112(3) . . ?
Cl1 C9 Cl3 113(2) . . ?
Cl2 C9 Cl3 112(2) . . ?
Cl1 C9 H9 106.5 . . ?
Cl2 C9 H9 106.5 . . ?
Cl3 C9 H9 106.5 . . ?
N1 C3 C4 122.0(17) 3_665 . ?
N1 C3 C2 117(2) 3_665 . ?
C4 C3 C2 121(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C4 C3 2(4) 3_665 . . . ?
C8 N2 C7 C6 179(2) 3_666 . . . ?
C8 N2 C7 C8 2(4) 3_666 . . . ?
N2 C7 C8 N2 -2(4) . . . 3_666 ?
C6 C7 C8 N2 -179(2) . . . 3_666 ?
N1 C4 C3 N1 -2(4) . . . 3_665 ?
N1 C4 C3 C2 178(2) . . . . ?

_refine_diff_density_max         2.135
_refine_diff_density_min         -1.876
_refine_diff_density_rms         0.308

_shelxl_version_number           2014/6

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
