# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1960896'
loop_
_audit_author_name
_audit_author_address
'Dong Liu'
;Huaibei Normal University
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 I N5'
_chemical_formula_weight         423.21

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.547(3)
_cell_length_b                   10.078(4)
_cell_length_c                   10.245(4)
_cell_angle_alpha                92.009(7)
_cell_angle_beta                 106.090(6)
_cell_angle_gamma                100.898(6)
_cell_volume                     829.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2725
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    1.940
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_T_max  0.6749
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            4118
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2867
_reflns_number_gt                2588
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2867
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.05855(3) 0.19100(3) 0.43248(3) 0.04578(11) Uani 1 1 d . . .
N3 N 0.8726(4) 0.4284(4) 0.6988(3) 0.0441(8) Uani 1 1 d . . .
C7 C 0.2828(4) 0.1945(4) 0.5840(4) 0.0329(8) Uani 1 1 d . . .
C10 C 0.6927(4) 0.4073(4) 0.6398(4) 0.0322(8) Uani 1 1 d . . .
H10A H 0.6544 0.4868 0.6670 0.039 Uiso 1 1 calc R . .
C13 C 0.6822(5) 0.1637(4) 0.6825(4) 0.0441(10) Uani 1 1 d . . .
C8 C 0.4287(4) 0.2454(3) 0.5649(3) 0.0296(8) Uani 1 1 d . . .
C9 C 0.5940(4) 0.2767(4) 0.6830(3) 0.0316(8) Uani 1 1 d . . .
C12 C 0.4800(5) 0.2929(4) 0.4464(4) 0.0331(8) Uani 1 1 d . . .
C11 C 0.6345(5) 0.3812(4) 0.4872(4) 0.0329(8) Uani 1 1 d . . .
C2 C 0.1643(5) 0.1855(5) 0.7818(4) 0.0485(10) Uani 1 1 d . . .
H2A H 0.1131 0.2570 0.7521 0.058 Uiso 1 1 calc R . .
C1 C 0.2585(4) 0.1350(4) 0.7088(4) 0.0356(8) Uani 1 1 d . . .
C14 C 0.5840(5) 0.3067(4) 0.8215(4) 0.0419(9) Uani 1 1 d . . .
N4 N 0.9304(5) 0.5193(4) 0.7933(4) 0.0540(10) Uani 1 1 d . . .
C15 C 0.4031(5) 0.2572(4) 0.3083(4) 0.0405(9) Uani 1 1 d . . .
H15A H 0.3015 0.1960 0.2786 0.049 Uiso 1 1 calc R . .
C18 C 0.7121(5) 0.4373(4) 0.3944(4) 0.0428(9) Uani 1 1 d . . .
H18A H 0.8154 0.4962 0.4237 0.051 Uiso 1 1 calc R . .
C6 C 0.3275(5) 0.0252(4) 0.7520(4) 0.0454(10) Uani 1 1 d . . .
H6A H 0.3880 -0.0110 0.7023 0.054 Uiso 1 1 calc R . .
C16 C 0.4810(6) 0.3147(4) 0.2152(4) 0.0488(11) Uani 1 1 d . . .
H16A H 0.4297 0.2926 0.1223 0.059 Uiso 1 1 calc R . .
N2 N 0.5904(5) 0.3402(5) 0.9294(4) 0.0698(12) Uani 1 1 d . . .
C17 C 0.6329(6) 0.4038(4) 0.2582(4) 0.0502(11) Uani 1 1 d . . .
H17A H 0.6822 0.4416 0.1940 0.060 Uiso 1 1 calc R . .
C5 C 0.3069(6) -0.0312(5) 0.8686(5) 0.0611(14) Uani 1 1 d . . .
H5A H 0.3537 -0.1051 0.8976 0.073 Uiso 1 1 calc R . .
N5 N 0.9980(7) 0.6010(6) 0.8789(5) 0.0949(17) Uani 1 1 d . . .
C4 C 0.2176(6) 0.0220(6) 0.9410(5) 0.0664(15) Uani 1 1 d . . .
H4A H 0.2047 -0.0151 1.0202 0.080 Uiso 1 1 calc R . .
N1 N 0.7426(5) 0.0752(4) 0.6778(5) 0.0750(13) Uani 1 1 d . . .
C3 C 0.1473(6) 0.1288(6) 0.8981(5) 0.0642(14) Uani 1 1 d . . .
H3A H 0.0867 0.1641 0.9485 0.077 Uiso 1 1 calc R . .


_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 2.099(4) . ?
N3 N4 1.234(5) . ?
N3 C10 1.458(5) . ?
C7 C8 1.325(5) . ?
C7 C1 1.480(5) . ?
C10 C11 1.501(5) . ?
C10 C9 1.570(5) . ?
C10 H10A 0.9800 . ?
C13 N1 1.118(6) . ?
C13 C9 1.481(6) . ?
C8 C12 1.468(5) . ?
C8 C9 1.554(5) . ?
C9 C14 1.469(5) . ?
C12 C15 1.386(5) . ?
C12 C11 1.390(5) . ?
C11 C18 1.381(5) . ?
C2 C3 1.371(6) . ?
C2 C1 1.389(6) . ?
C2 H2A 0.9300 . ?
C1 C6 1.380(6) . ?
C14 N2 1.128(5) . ?
N4 N5 1.127(6) . ?
C15 C16 1.391(6) . ?
C15 H15A 0.9300 . ?
C18 C17 1.370(6) . ?
C18 H18A 0.9300 . ?
C6 C5 1.381(6) . ?
C6 H6A 0.9300 . ?
C16 C17 1.379(6) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C5 C4 1.365(8) . ?
C5 H5A 0.9300 . ?
C4 C3 1.358(8) . ?
C4 H4A 0.9300 . ?
C3 H3A 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
N4 N3 C10 114.0(3) . . ?
C8 C7 C1 125.3(3) . . ?
C8 C7 I1 121.4(3) . . ?
C1 C7 I1 113.3(2) . . ?
N3 C10 C11 114.3(3) . . ?
N3 C10 C9 113.6(3) . . ?
C11 C10 C9 101.3(3) . . ?
N3 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N1 C13 C9 176.9(5) . . ?
C7 C8 C12 133.7(3) . . ?
C7 C8 C9 122.8(3) . . ?
C12 C8 C9 103.4(3) . . ?
C14 C9 C13 109.2(3) . . ?
C14 C9 C8 117.7(3) . . ?
C13 C9 C8 109.2(3) . . ?
C14 C9 C10 108.5(3) . . ?
C13 C9 C10 109.9(3) . . ?
C8 C9 C10 102.1(3) . . ?
C15 C12 C11 119.1(3) . . ?
C15 C12 C8 129.9(3) . . ?
C11 C12 C8 110.9(3) . . ?
C18 C11 C12 122.1(4) . . ?
C18 C11 C10 127.8(3) . . ?
C12 C11 C10 110.0(3) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C6 C1 C2 119.2(4) . . ?
C6 C1 C7 119.5(4) . . ?
C2 C1 C7 121.3(4) . . ?
N2 C14 C9 172.8(4) . . ?
N5 N4 N3 173.3(5) . . ?
C12 C15 C16 118.6(4) . . ?
C12 C15 H15A 120.7 . . ?
C16 C15 H15A 120.7 . . ?
C17 C18 C11 118.3(4) . . ?
C17 C18 H18A 120.9 . . ?
C11 C18 H18A 120.9 . . ?
C1 C6 C5 120.3(5) . . ?
C1 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.081
